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

Li, Z.-B.; Zuo, H.; Dong, W.-L.; He, X.-Y.; Chen, Z.-B.

doi:10.1107/S1600536808022526

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1609

doi:10.1107/S1600536808022526

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

Zhu-Bo Li,^a ^* Hua Zuo,^a Wen-Liang Dong,^b Xiao-Yan He ^a and Zhang-Bao Chen ^a

^aCollege of Pharmaceutical Sciences, Southwest University, Chongqing 400716, People's Republic of China, and ^bShandong University of Traditional Chinese Medicine, Jinan 250355, People's Republic of China
^*Correspondence e-mail: lizhubo2007@163.com

(Received 3 July 2008; accepted 18 July 2008; online 26 July 2008)

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.

Experimental

Crystal data

C₁₆H₁₆ClNO₂
M_r = 289.75
Orthorhombic, P b c a
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[F² > 2σ(F²)] = 0.045
wR(F²) = 0.133
S = 0.96
3286 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.21 e Å⁻³
Δρ_min = −0.22 e Å⁻³

Table 1
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 code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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 ).

Supporting information

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

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

checkCIF report

Related literature top

Please provide related literature.

Experimental top

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.

Computing details top

Data collection: APEX2 [or SMART?] (Bruker, 2005); cell refinement: APEX2 [or SMART?] (Bruker, 2005); data reduction: APEX2 [or SMART?] (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

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

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

Crystal data top

C₁₆H₁₆ClNO₂	D_x = 1.335 Mg m⁻³
M_r = 289.75	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2043 reflections
a = 11.9900 (18) Å	θ = 2.9–22.9°
b = 9.2986 (14) Å	µ = 0.27 mm⁻¹
c = 25.868 (4) Å	T = 273 K
V = 2884.1 (7) Å³	Block, colorless
Z = 8	0.15 × 0.10 × 0.10 mm
F(000) = 1216

Data collection top

Bruker SMART CCD area-detector diffractometer	1964 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.051
Graphite monochromator	θ_max = 27.5°, θ_min = 1.6°
ϕ and ω scans	h = −15→15
15831 measured reflections	k = −12→11
3286 independent reflections	l = −25→33

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	w = 1/[σ²(F_o²) + (0.06P)² + 0.774P] where P = (F_o² + 2F_c²)/3
3286 reflections	(Δ/σ)_max < 0.001
185 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.22 e Å⁻³

Crystal data top

C₁₆H₁₆ClNO₂	V = 2884.1 (7) Å³
M_r = 289.75	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 11.9900 (18) Å	µ = 0.27 mm⁻¹
b = 9.2986 (14) Å	T = 273 K
c = 25.868 (4) Å	0.15 × 0.10 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	1964 reflections with I > 2σ(I)
15831 measured reflections	R_int = 0.051
3286 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.133	H atoms treated by a mixture of independent and constrained refinement
S = 0.96	Δρ_max = 0.21 e Å⁻³
3286 reflections	Δρ_min = −0.22 e Å⁻³
185 parameters

Special details top

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) top

	x	y	z	U_iso*/U_eq
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) top

	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, º) top

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, º) top

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 code: (i) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆ClNO₂
M_r	289.75
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	273
a, b, c (Å)	11.9900 (18), 9.2986 (14), 25.868 (4)
V (Å³)	2884.1 (7)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.27
Crystal size (mm)	0.15 × 0.10 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	15831, 3286, 1964
R_int	0.051
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.133, 0.96
No. of reflections	3286
No. of parameters	185
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.22

Computer programs: APEX2 [or SMART?] (Bruker, 2005), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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 code: (i) −x+1/2, y+1/2, z.

Acknowledgements

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

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. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bruker (2005). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar