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

Chen, M.-J.; Fu, Y.-W.; Dong, W.-L.; Li, Z.-B.; Zuo, H.

doi:10.1107/S1600536808029371

organic compounds

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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Page o1968

doi:10.1107/S1600536808029371

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

Ming-Jun Chen,^a Yang-Wu Fu,^a Wen-Liang Dong,^b Zhu-Bo Li ^c ^* and Hua Zuo ^c

^aCollege of Chemical and Environmental Engineering, Chongqing Three Gorges University, Chongqing, 404000, People's Republic of China, ^bShandong University of Traditional Chinese Medicine, Jinan, 250355, People's Republic of China, and ^cCollege of Pharmaceutical Sciences, Southwest University, Chongqing, 400716, People's Republic of China
^*Correspondence e-mail: lizhubo2007@163.com

(Received 17 July 2008; accepted 13 September 2008; online 20 September 2008)

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 ,b ).

Experimental

Crystal data

C₁₅H₁₃Cl₂NO₂
M_r = 310.16
Monoclinic, P 2₁ /c
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 )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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.103
S = 1.03
3254 reflections
185 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2ⁱ	0.83 (2)	2.06 (2)	2.883 (2)	169 (2)
Symmetry code: (i) x-1, y, z.

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; 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, New_Global_Publ_Block. DOI: 10.1107/S1600536808029371/cs2090sup1.cif

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

checkCIF report

Comment top

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.

Related literature top

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

Experimental top

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.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: APEX2 (Bruker, 2005); data reduction: APEX2 (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 the title compound showing displacement ellipsoids drawn at 50% probability level.

N-benzyl-2-(2,4-dichlorophenoxy)acetamide top

Crystal data top

C₁₅H₁₃Cl₂NO₂	F(000) = 640
M_r = 310.16	D_x = 1.421 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2023 reflections
a = 4.7447 (6) Å	θ = 2.4–24.3°
b = 26.821 (3) Å	µ = 0.45 mm⁻¹
c = 11.3962 (15) Å	T = 298 K
β = 90.402 (2)°	Prism, colourless
V = 1450.2 (3) Å³	0.30 × 0.10 × 0.05 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	3254 independent reflections
Radiation source: fine-focus sealed tube	2233 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
phi and ω scans	θ_max = 27.5°, θ_min = 1.5°
Absorption correction: multi-scan (PROGRAM? REFERENCE?)	h = −6→6
T_min = 0.878, T_max = 0.978	k = −26→34
8418 measured reflections	l = −14→14

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0422P)² + 0.2337P] where P = (F_o² + 2F_c²)/3
3254 reflections	(Δ/σ)_max = 0.001
185 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₅H₁₃Cl₂NO₂	V = 1450.2 (3) Å³
M_r = 310.16	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 4.7447 (6) Å	µ = 0.45 mm⁻¹
b = 26.821 (3) Å	T = 298 K
c = 11.3962 (15) Å	0.30 × 0.10 × 0.05 mm
β = 90.402 (2)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3254 independent reflections
Absorption correction: multi-scan (PROGRAM? REFERENCE?)	2233 reflections with I > 2σ(I)
T_min = 0.878, T_max = 0.978	R_int = 0.027
8418 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.103	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.19 e Å⁻³
3254 reflections	Δρ_min = −0.24 e Å⁻³
185 parameters

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

	x	y	z	U_iso*/U_eq
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)
Cl2	0.22803 (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)
C2	0.0880 (4)	0.35291 (7)	1.16733 (16)	0.0470 (5)
H2A	0.2087	0.3767	1.1991	0.056*
C3	0.0511 (4)	0.34928 (7)	1.04765 (16)	0.0462 (5)
C4	−0.1215 (4)	0.31367 (7)	0.99970 (17)	0.0496 (5)
H4A	−0.1415	0.3112	0.9187	0.059*
C5	−0.2659 (4)	0.28142 (7)	1.07243 (16)	0.0468 (5)
H5A	−0.3834	0.2573	1.0398	0.056*
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	−0.6842	0.2334	1.1707	0.056*
H7B	−0.6816	0.2075	1.2941	0.056*
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	−0.2910	0.0966	1.0615	0.061*
H9B	−0.5912	0.0880	1.0071	0.061*
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	−0.8146	0.0140	1.0574	0.087*
C12	−0.7554 (7)	−0.02898 (10)	1.2005 (3)	0.0908 (9)
H12A	−0.8836	−0.0536	1.1788	0.109*
C13	−0.6107 (7)	−0.03343 (10)	1.3027 (3)	0.0872 (9)
H13A	−0.6395	−0.0608	1.3514	0.105*
C14	−0.4209 (6)	0.00298 (11)	1.3337 (2)	0.0822 (8)
H14A	−0.3190	0.0001	1.4034	0.099*
C15	−0.3801 (5)	0.04402 (9)	1.2619 (2)	0.0640 (6)
H15A	−0.2512	0.0685	1.2838	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0327 (9)	0.0426 (9)	0.0543 (10)	0.0032 (7)	0.0025 (7)	−0.0059 (7)
Cl1	0.1088 (5)	0.0673 (4)	0.0393 (3)	−0.0261 (3)	−0.0006 (3)	−0.0106 (2)
Cl2	0.0869 (5)	0.0663 (4)	0.0604 (3)	−0.0168 (3)	0.0117 (3)	0.0131 (3)
O1	0.0517 (8)	0.0405 (7)	0.0479 (7)	−0.0087 (6)	0.0045 (6)	−0.0019 (6)
O2	0.0307 (7)	0.0527 (8)	0.0764 (10)	0.0030 (6)	0.0010 (6)	−0.0051 (7)
C1	0.0511 (11)	0.0370 (10)	0.0376 (9)	−0.0001 (8)	0.0002 (8)	−0.0071 (8)
C2	0.0539 (12)	0.0377 (10)	0.0492 (11)	−0.0072 (9)	0.0011 (9)	−0.0065 (8)
C3	0.0506 (11)	0.0407 (10)	0.0475 (11)	0.0004 (9)	0.0053 (9)	0.0029 (9)
C4	0.0584 (13)	0.0515 (12)	0.0388 (10)	0.0030 (10)	−0.0048 (9)	0.0002 (9)
C5	0.0488 (11)	0.0439 (11)	0.0478 (11)	−0.0042 (9)	−0.0083 (9)	−0.0046 (9)
C6	0.0394 (10)	0.0320 (9)	0.0445 (10)	0.0029 (8)	0.0014 (8)	−0.0020 (8)
C7	0.0377 (10)	0.0403 (10)	0.0626 (12)	−0.0041 (8)	0.0075 (9)	−0.0021 (9)
C8	0.0329 (10)	0.0354 (9)	0.0428 (10)	0.0010 (7)	0.0025 (7)	0.0057 (7)
C9	0.0542 (13)	0.0478 (12)	0.0501 (11)	0.0018 (9)	0.0049 (9)	−0.0093 (9)
C10	0.0456 (11)	0.0404 (10)	0.0519 (11)	0.0043 (9)	0.0101 (9)	−0.0087 (9)
C11	0.0747 (17)	0.0613 (15)	0.0816 (17)	−0.0152 (13)	−0.0013 (13)	−0.0055 (13)
C12	0.098 (2)	0.0560 (16)	0.119 (3)	−0.0247 (15)	0.020 (2)	−0.0025 (16)
C13	0.103 (2)	0.0540 (16)	0.105 (2)	0.0148 (16)	0.0368 (19)	0.0151 (15)
C14	0.096 (2)	0.0809 (19)	0.0693 (17)	0.0239 (17)	0.0031 (14)	0.0134 (15)
C15	0.0697 (15)	0.0590 (14)	0.0632 (14)	0.0012 (11)	−0.0021 (12)	−0.0024 (11)

Geometric parameters (Å, º) top

N—C8	1.329 (2)	C7—C8	1.517 (2)
N—C9	1.451 (2)	C7—H7A	0.9700
N—H0A	0.83 (2)	C7—H7B	0.9700
Cl1—C1	1.7318 (18)	C9—C10	1.507 (3)
Cl2—C3	1.7448 (19)	C9—H9A	0.9700
O1—C6	1.363 (2)	C9—H9B	0.9700
O1—C7	1.420 (2)	C10—C11	1.372 (3)
O2—C8	1.225 (2)	C10—C15	1.377 (3)
C1—C2	1.376 (3)	C11—C12	1.385 (4)
C1—C6	1.394 (2)	C11—H11A	0.9300
C2—C3	1.377 (3)	C12—C13	1.353 (4)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.369 (3)	C13—C14	1.373 (4)
C4—C5	1.383 (3)	C13—H13A	0.9300
C4—H4A	0.9300	C14—C15	1.386 (3)
C5—C6	1.383 (2)	C14—H14A	0.9300
C5—H5A	0.9300	C15—H15A	0.9300

C8—N—C9	123.59 (16)	O2—C8—N	124.41 (16)
C8—N—H0A	115.6 (14)	O2—C8—C7	121.43 (16)
C9—N—H0A	120.7 (14)	N—C8—C7	114.16 (15)
C6—O1—C7	118.32 (14)	N—C9—C10	113.22 (16)
C2—C1—C6	121.47 (17)	N—C9—H9A	108.9
C2—C1—Cl1	119.52 (14)	C10—C9—H9A	108.9
C6—C1—Cl1	119.00 (14)	N—C9—H9B	108.9
C1—C2—C3	118.88 (17)	C10—C9—H9B	108.9
C1—C2—H2A	120.6	H9A—C9—H9B	107.7
C3—C2—H2A	120.6	C11—C10—C15	118.4 (2)
C4—C3—C2	121.07 (18)	C11—C10—C9	120.5 (2)
C4—C3—Cl2	119.33 (15)	C15—C10—C9	121.05 (19)
C2—C3—Cl2	119.60 (15)	C10—C11—C12	120.7 (3)
C3—C4—C5	119.63 (18)	C10—C11—H11A	119.7
C3—C4—H4A	120.2	C12—C11—H11A	119.7
C5—C4—H4A	120.2	C13—C12—C11	120.9 (3)
C6—C5—C4	120.84 (18)	C13—C12—H12A	119.6
C6—C5—H5A	119.6	C11—C12—H12A	119.6
C4—C5—H5A	119.6	C12—C13—C14	119.1 (3)
O1—C6—C5	125.67 (16)	C12—C13—H13A	120.5
O1—C6—C1	116.25 (15)	C14—C13—H13A	120.5
C5—C6—C1	118.09 (17)	C13—C14—C15	120.5 (3)
O1—C7—C8	112.50 (14)	C13—C14—H14A	119.8
O1—C7—H7A	109.1	C15—C14—H14A	119.8
C8—C7—H7A	109.1	C10—C15—C14	120.4 (2)
O1—C7—H7B	109.1	C10—C15—H15A	119.8
C8—C7—H7B	109.1	C14—C15—H15A	119.8
H7A—C7—H7B	107.8

C6—C1—C2—C3	0.3 (3)	C9—N—C8—O2	0.7 (3)
Cl1—C1—C2—C3	179.74 (15)	C9—N—C8—C7	−178.70 (16)
C1—C2—C3—C4	−1.4 (3)	O1—C7—C8—O2	3.5 (3)
C1—C2—C3—Cl2	178.90 (14)	O1—C7—C8—N	−177.05 (15)
C2—C3—C4—C5	1.3 (3)	C8—N—C9—C10	103.3 (2)
Cl2—C3—C4—C5	−178.97 (15)	N—C9—C10—C11	113.8 (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—C12	1.4 (3)
C7—O1—C6—C1	178.78 (15)	C9—C10—C11—C12	−179.0 (2)
C4—C5—C6—O1	179.23 (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—C15	0.7 (4)
Cl1—C1—C6—O1	1.3 (2)	C11—C10—C15—C14	−0.9 (3)
C2—C1—C6—C5	0.9 (3)	C9—C10—C15—C14	179.4 (2)
Cl1—C1—C6—C5	−178.57 (14)	C13—C14—C15—C10	−0.1 (4)
C6—O1—C7—C8	75.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.83 (2)	2.06 (2)	2.883 (2)	169 (2)

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃Cl₂NO₂
M_r	310.16
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	4.7447 (6), 26.821 (3), 11.3962 (15)
β (°)	90.402 (2)
V (Å³)	1450.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.45
Crystal size (mm)	0.30 × 0.10 × 0.05

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (PROGRAM? REFERENCE?)
T_min, T_max	0.878, 0.978
No. of measured, independent and observed [I > 2σ(I)] reflections	8418, 3254, 2233
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.103, 1.03
No. of reflections	3254
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)	0.19, −0.24

Computer programs: APEX2 (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—H0A···O2ⁱ	0.83 (2)	2.06 (2)	2.883 (2)	169 (2)

Symmetry code: (i) x−1, y, z.

Acknowledgements

This study was supported by the Science and Technology Key Project of Chongqing Science and Technology Commission, 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). SADABS and 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
Li, Z.-B., Luo, Y.-H., Dong, W.-L., Li, J. & Zuo, H. (2008a). Acta Cryst. E64, o1610. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, Z.-B., Zuo, H., Dong, W.-L., He, X.-Y. & Chen, Z.-B. (2008b). Acta Cryst. E64, o1609. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar