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Acta Crystallographica Section E: Structure Reports Online logoLink to Acta Crystallographica Section E: Structure Reports Online
. 2008 Jul 26;64(Pt 8):o1609. doi: 10.1107/S1600536808022526

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

Zhu-Bo Li a,*, Hua Zuo a, Wen-Liang Dong b, Xiao-Yan He a, Zhang-Bao Chen a
PMCID: PMC2962221  PMID: 21203302

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.graphic file with name e-64-o1609-scheme1.jpg

Experimental

Crystal data

  • C16H16ClNO2

  • M r = 289.75

  • Orthorhombic, Inline graphic

  • 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); cell refinement: APEX2; data reduction: APEX2; 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).

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022526/nc2110sup1.cif

e-64-o1609-sup1.cif (18KB, cif)

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

e-64-o1609-Isup2.hkl (161.3KB, hkl)

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

Table 1. Hydrogen-bond geometry (Å, °).

D—H⋯A D—H H⋯A DA D—H⋯A
N—H⋯O2i 0.80 (2) 2.09 (3) 2.885 (2) 169 (2)

Symmetry code: (i) Inline graphic.

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.

Fig. 1.

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

Crystal data

C16H16ClNO2 Dx = 1.335 Mg m3
Mr = 289.75 Mo Kα radiation λ = 0.71073 Å
Orthorhombic, Pbca Cell parameters from 2043 reflections
a = 11.9900 (18) Å θ = 2.9–22.9º
b = 9.2986 (14) Å µ = 0.27 mm1
c = 25.868 (4) Å T = 273 (2) K
V = 2884.1 (7) Å3 Block, colorless
Z = 8 0.15 × 0.10 × 0.10 mm
F000 = 1216

Data collection

Bruker SMART CCD area-detector diffractometer 1964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube Rint = 0.051
Monochromator: graphite θmax = 27.5º
T = 273(2) K θmin = 1.6º
φ and ω scans h = −15→15
Absorption correction: none k = −12→11
15831 measured reflections l = −25→33
3286 independent reflections

Refinement

Refinement on F2 Secondary atom site location: difference Fourier map
Least-squares matrix: full Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.046 H 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 reflections Δρmax = 0.21 e Å3
185 parameters Δρmin = −0.22 e Å3
Primary atom site location: structure-invariant direct methods Extinction 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)

x y z Uiso*/Ueq
N 0.25818 (17) 0.4733 (2) 0.38688 (7) 0.0475 (5)
H 0.2699 (18) 0.557 (3) 0.3929 (9) 0.049 (7)*
Cl1 0.03007 (5) 0.17559 (7) 0.57574 (3) 0.0657 (2)
O1 0.12962 (13) 0.38711 (16) 0.50994 (6) 0.0518 (4)
O2 0.19800 (14) 0.26379 (16) 0.42037 (6) 0.0557 (4)
C1 0.17217 (18) 0.2116 (2) 0.57204 (8) 0.0449 (5)
C2 0.24535 (19) 0.1359 (2) 0.60276 (8) 0.0479 (5)
H2 0.2178 0.0675 0.6257 0.057*
C3 0.35942 (19) 0.1599 (2) 0.60016 (9) 0.0484 (5)
C4 0.4390 (2) 0.0750 (3) 0.63326 (10) 0.0669 (7)
H4A 0.5140 0.1053 0.6263 0.100*
H4B 0.4315 −0.0255 0.6255 0.100*
H4C 0.4221 0.0911 0.6691 0.100*
C5 0.3965 (2) 0.2623 (3) 0.56529 (9) 0.0518 (6)
H5 0.4726 0.2803 0.5626 0.062*
C6 0.32366 (19) 0.3384 (2) 0.53445 (9) 0.0498 (6)
H6 0.3514 0.4062 0.5113 0.060*
C7 0.20977 (18) 0.3153 (2) 0.53747 (8) 0.0431 (5)
C8 0.1658 (2) 0.4792 (2) 0.46959 (8) 0.0510 (6)
H8A 0.2239 0.5422 0.4825 0.061*
H8B 0.1038 0.5387 0.4584 0.061*
C9 0.21020 (18) 0.3948 (2) 0.42362 (8) 0.0428 (5)
C10 0.2954 (2) 0.4080 (2) 0.33864 (8) 0.0510 (6)
H10A 0.2365 0.3473 0.3250 0.061*
H10B 0.3597 0.3477 0.3454 0.061*
C11 0.32561 (18) 0.5196 (2) 0.29900 (8) 0.0441 (5)
C12 0.2495 (2) 0.5609 (2) 0.26193 (9) 0.0547 (6)
H12 0.1787 0.5201 0.2619 0.066*
C13 0.2765 (2) 0.6617 (3) 0.22488 (10) 0.0653 (7)
H13 0.2241 0.6880 0.2001 0.078*
C14 0.3801 (2) 0.7230 (3) 0.22441 (10) 0.0655 (7)
H14 0.3985 0.7901 0.1991 0.079*
C15 0.4562 (2) 0.6855 (3) 0.26101 (12) 0.0686 (7)
H15 0.5263 0.7282 0.2611 0.082*
C16 0.4294 (2) 0.5832 (3) 0.29846 (10) 0.0608 (7)
H16 0.4820 0.5577 0.3232 0.073*

Atomic displacement parameters (Å2)

U11 U22 U33 U12 U13 U23
N 0.0699 (13) 0.0305 (10) 0.0421 (10) −0.0025 (9) 0.0022 (9) −0.0059 (8)
Cl1 0.0507 (4) 0.0739 (5) 0.0724 (5) −0.0075 (3) 0.0088 (3) 0.0085 (3)
O1 0.0589 (10) 0.0498 (9) 0.0468 (9) 0.0051 (8) 0.0059 (7) 0.0039 (7)
O2 0.0827 (12) 0.0299 (8) 0.0546 (10) 0.0008 (8) 0.0042 (8) −0.0021 (7)
C1 0.0479 (12) 0.0466 (12) 0.0403 (12) −0.0045 (10) 0.0084 (10) −0.0056 (10)
C2 0.0601 (14) 0.0441 (12) 0.0393 (11) −0.0043 (11) 0.0071 (11) −0.0013 (10)
C3 0.0573 (14) 0.0465 (13) 0.0413 (12) 0.0001 (11) 0.0005 (10) −0.0075 (10)
C4 0.0665 (16) 0.0714 (17) 0.0627 (16) 0.0036 (14) −0.0056 (13) 0.0011 (14)
C5 0.0480 (13) 0.0502 (14) 0.0572 (14) −0.0033 (11) 0.0017 (11) −0.0088 (11)
C6 0.0588 (14) 0.0441 (12) 0.0465 (13) −0.0063 (11) 0.0104 (11) −0.0021 (10)
C7 0.0525 (13) 0.0409 (11) 0.0360 (11) −0.0006 (10) 0.0058 (9) −0.0072 (9)
C8 0.0690 (15) 0.0373 (11) 0.0468 (13) 0.0048 (11) 0.0035 (11) 0.0006 (10)
C9 0.0546 (13) 0.0341 (11) 0.0397 (12) 0.0046 (9) −0.0050 (10) 0.0012 (9)
C10 0.0690 (15) 0.0424 (12) 0.0414 (12) 0.0060 (11) −0.0006 (11) −0.0038 (10)
C11 0.0501 (13) 0.0410 (11) 0.0410 (12) 0.0054 (10) 0.0032 (10) −0.0050 (9)
C12 0.0540 (14) 0.0569 (14) 0.0531 (14) −0.0011 (12) −0.0045 (11) 0.0017 (11)
C13 0.0795 (19) 0.0671 (16) 0.0494 (14) 0.0046 (14) −0.0054 (13) 0.0077 (13)
C14 0.084 (2) 0.0584 (16) 0.0541 (16) 0.0035 (14) 0.0201 (15) 0.0046 (12)
C15 0.0574 (16) 0.0654 (17) 0.083 (2) −0.0106 (13) 0.0191 (14) −0.0030 (15)
C16 0.0523 (14) 0.0636 (16) 0.0665 (17) 0.0048 (12) −0.0075 (12) −0.0037 (13)

Geometric parameters (Å, °)

N—C9 1.329 (3) C6—H6 0.9300
N—C10 1.458 (3) C8—C9 1.521 (3)
N—H 0.80 (2) C8—H8A 0.9700
Cl1—C1 1.739 (2) C8—H8B 0.9700
O1—C7 1.370 (3) C10—C11 1.503 (3)
O1—C8 1.418 (3) C10—H10A 0.9700
O2—C9 1.230 (2) C10—H10B 0.9700
C1—C2 1.377 (3) C11—C16 1.378 (3)
C1—C7 1.390 (3) C11—C12 1.378 (3)
C2—C3 1.387 (3) C12—C13 1.380 (3)
C2—H2 0.9300 C12—H12 0.9300
C3—C5 1.385 (3) C13—C14 1.366 (4)
C3—C4 1.505 (3) C13—H13 0.9300
C4—H4A 0.9600 C14—C15 1.361 (4)
C4—H4B 0.9600 C14—H14 0.9300
C4—H4C 0.9600 C15—C16 1.395 (4)
C5—C6 1.378 (3) C15—H15 0.9300
C5—H5 0.9300 C16—H16 0.9300
C6—C7 1.385 (3)
C9—N—C10 121.07 (19) O1—C8—H8B 109.3
C9—N—H 117.9 (16) C9—C8—H8B 109.3
C10—N—H 120.9 (16) H8A—C8—H8B 107.9
C7—O1—C8 117.56 (17) O2—C9—N 123.1 (2)
C2—C1—C7 121.3 (2) O2—C9—C8 121.51 (19)
C2—C1—Cl1 119.61 (17) N—C9—C8 115.30 (18)
C7—C1—Cl1 119.12 (17) N—C10—C11 111.74 (17)
C1—C2—C3 121.2 (2) N—C10—H10A 109.3
C1—C2—H2 119.4 C11—C10—H10A 109.3
C3—C2—H2 119.4 N—C10—H10B 109.3
C2—C3—C5 117.3 (2) C11—C10—H10B 109.3
C2—C3—C4 120.9 (2) H10A—C10—H10B 107.9
C5—C3—C4 121.8 (2) C16—C11—C12 118.1 (2)
C3—C4—H4A 109.5 C16—C11—C10 121.4 (2)
C3—C4—H4B 109.5 C12—C11—C10 120.5 (2)
H4A—C4—H4B 109.5 C11—C12—C13 121.1 (2)
C3—C4—H4C 109.5 C11—C12—H12 119.4
H4A—C4—H4C 109.5 C13—C12—H12 119.4
H4B—C4—H4C 109.5 C14—C13—C12 120.2 (3)
C6—C5—C3 121.8 (2) C14—C13—H13 119.9
C6—C5—H5 119.1 C12—C13—H13 119.9
C3—C5—H5 119.1 C15—C14—C13 119.8 (2)
C5—C6—C7 120.8 (2) C15—C14—H14 120.1
C5—C6—H6 119.6 C13—C14—H14 120.1
C7—C6—H6 119.6 C14—C15—C16 120.2 (2)
O1—C7—C6 125.9 (2) C14—C15—H15 119.9
O1—C7—C1 116.42 (19) C16—C15—H15 119.9
C6—C7—C1 117.6 (2) C11—C16—C15 120.5 (2)
O1—C8—C9 111.79 (17) C11—C16—H16 119.8
O1—C8—H8A 109.3 C15—C16—H16 119.8
C9—C8—H8A 109.3
C7—C1—C2—C3 −0.3 (3) C10—N—C9—O2 2.8 (3)
Cl1—C1—C2—C3 178.82 (16) C10—N—C9—C8 −174.4 (2)
C1—C2—C3—C5 −0.3 (3) O1—C8—C9—O2 10.6 (3)
C1—C2—C3—C4 −179.0 (2) O1—C8—C9—N −172.11 (19)
C2—C3—C5—C6 0.3 (3) C9—N—C10—C11 168.6 (2)
C4—C3—C5—C6 179.0 (2) N—C10—C11—C16 83.7 (3)
C3—C5—C6—C7 0.3 (3) N—C10—C11—C12 −96.4 (2)
C8—O1—C7—C6 9.4 (3) C16—C11—C12—C13 0.8 (3)
C8—O1—C7—C1 −171.68 (17) C10—C11—C12—C13 −179.1 (2)
C5—C6—C7—O1 178.02 (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—C16 1.0 (4)
Cl1—C1—C7—O1 2.7 (2) C12—C11—C16—C15 −0.5 (3)
C2—C1—C7—C6 0.9 (3) C10—C11—C16—C15 179.4 (2)
Cl1—C1—C7—C6 −178.22 (16) C14—C15—C16—C11 −0.4 (4)
C7—O1—C8—C9 71.4 (2)

Hydrogen-bond geometry (Å, °)

D—H···A D—H H···A D···A D—H···A
N—H···O2i 0.80 (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

  1. 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.
  2. Bruker (2005). APEX2 Bruker AXS Inc., Madison, Wisconsin, USA.
  3. Farrugia, L. J. (1999). J. Appl. Cryst.32, 837–838.
  4. Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [DOI] [PubMed]

Associated Data

This section collects any data citations, data availability statements, or supplementary materials included in this article.

Supplementary Materials

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808022526/nc2110sup1.cif

e-64-o1609-sup1.cif (18KB, cif)

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

e-64-o1609-Isup2.hkl (161.3KB, hkl)

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


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