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

Li, Z.-B.; Luo, Y.-H.; Dong, W.-L.; Li, J.; Zuo, H.

doi:10.1107/S1600536808022514

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1610

doi:10.1107/S1600536808022514

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

Zhu-Bo Li,^a ^* Yong-Huang Luo,^a Wen-Liang Dong,^b Jing Li ^a and Hua Zuo ^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 8 July 2008; accepted 18 July 2008; online 26 July 2008)

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.

Experimental

Crystal data

C₁₅H₁₃Cl₂NO₂
M_r = 310.16
Orthorhombic, P b c a
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 ) 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[F² > 2σ(F²)] = 0.044
wR(F²) = 0.131
S = 1.02
3412 reflections
181 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.34 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.86	2.23	2.644 (2)	109
N1—H1A⋯O2ⁱ	0.86	2.31	2.970 (2)	133
Symmetry code: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, z]$ .

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/S1600536808022514/nc2111sup1.cif

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

checkCIF report

Related literature top

Please provide references to some related literature.

Experimental top

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.

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 with labelling and displacement ellipsoids drawn at the 50% probability level.

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

Crystal data top

C₁₅H₁₃Cl₂NO₂	D_x = 1.391 Mg m⁻³
M_r = 310.16	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 2733 reflections
a = 14.8886 (10) Å	θ = 2.2–21.8°
b = 8.6579 (6) Å	µ = 0.44 mm⁻¹
c = 22.9867 (14) Å	T = 298 K
V = 2963.1 (3) Å³	Block, colorless
Z = 8	0.20 × 0.20 × 0.10 mm
F(000) = 1280

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 independent reflections
Radiation source: fine-focus sealed tube	2103 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
ϕ and ω scans	θ_max = 27.5°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −19→18
T_min = 0.918, T_max = 0.958	k = −10→11
16445 measured reflections	l = −20→29

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0631P)² + 0.3666P] where P = (F_o² + 2F_c²)/3
3412 reflections	(Δ/σ)_max = 0.001
181 parameters	Δρ_max = 0.20 e Å⁻³
0 restraints	Δρ_min = −0.34 e Å⁻³

Crystal data top

C₁₅H₁₃Cl₂NO₂	V = 2963.1 (3) Å³
M_r = 310.16	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 14.8886 (10) Å	µ = 0.44 mm⁻¹
b = 8.6579 (6) Å	T = 298 K
c = 22.9867 (14) Å	0.20 × 0.20 × 0.10 mm

Data collection top

Bruker SMART CCD area-detector diffractometer	3412 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2103 reflections with I > 2σ(I)
T_min = 0.918, T_max = 0.958	R_int = 0.040
16445 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.131	H-atom parameters constrained
S = 1.02	Δρ_max = 0.20 e Å⁻³
3412 reflections	Δρ_min = −0.34 e Å⁻³
181 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
N1	0.74097 (11)	0.0194 (2)	0.64026 (7)	0.0521 (4)
H1A	0.7004	0.0734	0.6230	0.063*
Cl1	0.74730 (5)	0.13003 (7)	0.41952 (3)	0.0787 (2)
Cl2	0.55214 (5)	−0.24316 (9)	0.55609 (4)	0.0985 (3)
O1	0.68835 (9)	−0.00499 (15)	0.53078 (6)	0.0526 (4)
O2	0.84330 (10)	−0.17088 (18)	0.62980 (6)	0.0591 (4)
C1	0.65927 (14)	0.0023 (2)	0.42821 (9)	0.0515 (5)
C2	0.60907 (17)	−0.0417 (3)	0.38036 (11)	0.0679 (7)
H2A	0.6217	−0.0014	0.3438	0.081*
C3	0.54023 (18)	−0.1457 (3)	0.38759 (14)	0.0802 (8)
H3A	0.5057	−0.1746	0.3557	0.096*
C4	0.52178 (17)	−0.2071 (3)	0.44101 (13)	0.0761 (8)
H4A	0.4755	−0.2783	0.4454	0.091*
C5	0.57263 (15)	−0.1625 (3)	0.48853 (11)	0.0603 (6)
C6	0.64111 (13)	−0.0555 (2)	0.48288 (9)	0.0466 (5)
C7	0.76294 (14)	−0.1008 (3)	0.54620 (9)	0.0522 (5)
H7A	0.8148	−0.0717	0.5231	0.063*
H7B	0.7487	−0.2076	0.5375	0.063*
C8	0.78542 (13)	−0.0856 (2)	0.60971 (9)	0.0433 (5)
C9	0.75781 (14)	0.0471 (3)	0.70161 (9)	0.0597 (6)
H9A	0.7848	0.1484	0.7060	0.072*
H9B	0.8007	−0.0286	0.7155	0.072*
C10	0.67475 (13)	0.0393 (2)	0.73885 (8)	0.0471 (5)
C11	0.67143 (16)	0.1244 (3)	0.78942 (9)	0.0586 (6)
H11A	0.7190	0.1894	0.7988	0.070*
C12	0.59859 (17)	0.1148 (3)	0.82645 (10)	0.0696 (7)
H12A	0.5979	0.1718	0.8607	0.084*
C13	0.52742 (17)	0.0216 (3)	0.81283 (11)	0.0693 (7)
H13A	0.4780	0.0165	0.8375	0.083*
C14	0.52928 (16)	−0.0638 (3)	0.76294 (11)	0.0697 (7)
H14A	0.4814	−0.1283	0.7538	0.084*
C15	0.60248 (15)	−0.0545 (3)	0.72586 (10)	0.0609 (6)
H15A	0.6029	−0.1123	0.6918	0.073*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0540 (10)	0.0620 (11)	0.0404 (9)	0.0117 (8)	0.0022 (8)	−0.0039 (8)
Cl1	0.0982 (5)	0.0733 (4)	0.0644 (4)	−0.0303 (4)	−0.0038 (3)	0.0045 (3)
Cl2	0.0904 (5)	0.1033 (6)	0.1019 (6)	−0.0081 (4)	0.0394 (4)	0.0184 (4)
O1	0.0594 (9)	0.0521 (8)	0.0463 (8)	0.0140 (7)	−0.0084 (7)	−0.0094 (6)
O2	0.0484 (8)	0.0657 (9)	0.0633 (10)	0.0121 (7)	−0.0112 (7)	−0.0085 (7)
C1	0.0582 (12)	0.0460 (12)	0.0503 (12)	0.0008 (10)	−0.0087 (10)	−0.0080 (9)
C2	0.0867 (18)	0.0606 (14)	0.0565 (14)	0.0067 (13)	−0.0203 (12)	−0.0093 (11)
C3	0.0734 (18)	0.0740 (18)	0.093 (2)	0.0044 (14)	−0.0355 (16)	−0.0234 (15)
C4	0.0485 (13)	0.0675 (17)	0.112 (2)	−0.0034 (12)	−0.0089 (14)	−0.0132 (15)
C5	0.0466 (12)	0.0599 (13)	0.0745 (16)	0.0051 (11)	0.0084 (11)	−0.0035 (11)
C6	0.0443 (11)	0.0458 (11)	0.0497 (12)	0.0084 (9)	−0.0027 (9)	−0.0087 (9)
C7	0.0507 (12)	0.0603 (13)	0.0456 (12)	0.0127 (10)	0.0006 (9)	−0.0098 (9)
C8	0.0362 (10)	0.0448 (11)	0.0488 (12)	−0.0023 (9)	0.0028 (9)	−0.0019 (9)
C9	0.0522 (12)	0.0828 (17)	0.0441 (12)	−0.0021 (11)	0.0004 (10)	−0.0138 (11)
C10	0.0481 (11)	0.0523 (12)	0.0409 (11)	0.0042 (9)	−0.0021 (9)	0.0014 (9)
C11	0.0599 (13)	0.0665 (15)	0.0495 (12)	−0.0068 (11)	0.0043 (11)	−0.0085 (10)
C12	0.0749 (16)	0.0836 (17)	0.0503 (13)	−0.0039 (14)	0.0138 (12)	−0.0113 (12)
C13	0.0610 (14)	0.0832 (18)	0.0636 (16)	−0.0015 (13)	0.0164 (12)	0.0084 (13)
C14	0.0580 (14)	0.0770 (16)	0.0740 (17)	−0.0139 (13)	0.0017 (12)	0.0038 (13)
C15	0.0621 (14)	0.0654 (14)	0.0552 (14)	−0.0045 (12)	−0.0020 (11)	−0.0112 (11)

Geometric parameters (Å, º) top

N1—C8	1.326 (2)	C7—C8	1.504 (3)
N1—C9	1.452 (3)	C7—H7A	0.9700
N1—H1A	0.8600	C7—H7B	0.9700
Cl1—C1	1.726 (2)	C9—C10	1.506 (3)
Cl2—C5	1.730 (3)	C9—H9A	0.9700
O1—C6	1.378 (2)	C9—H9B	0.9700
O1—C7	1.431 (2)	C10—C11	1.378 (3)
O2—C8	1.225 (2)	C10—C15	1.381 (3)
C1—C6	1.379 (3)	C11—C12	1.381 (3)
C1—C2	1.383 (3)	C11—H11A	0.9300
C2—C3	1.374 (4)	C12—C13	1.368 (3)
C2—H2A	0.9300	C12—H12A	0.9300
C3—C4	1.366 (4)	C13—C14	1.365 (3)
C3—H3A	0.9300	C13—H13A	0.9300
C4—C5	1.384 (3)	C14—C15	1.386 (3)
C4—H4A	0.9300	C14—H14A	0.9300
C5—C6	1.384 (3)	C15—H15A	0.9300

C8—N1—C9	122.78 (18)	O2—C8—N1	124.39 (19)
C8—N1—H1A	118.6	O2—C8—C7	118.03 (18)
C9—N1—H1A	118.6	N1—C8—C7	117.58 (17)
C6—O1—C7	114.23 (14)	N1—C9—C10	113.75 (17)
C6—C1—C2	121.2 (2)	N1—C9—H9A	108.8
C6—C1—Cl1	119.12 (15)	C10—C9—H9A	108.8
C2—C1—Cl1	119.65 (18)	N1—C9—H9B	108.8
C3—C2—C1	119.2 (2)	C10—C9—H9B	108.8
C3—C2—H2A	120.4	H9A—C9—H9B	107.7
C1—C2—H2A	120.4	C11—C10—C15	118.0 (2)
C4—C3—C2	120.9 (2)	C11—C10—C9	119.02 (19)
C4—C3—H3A	119.5	C15—C10—C9	122.96 (19)
C2—C3—H3A	119.5	C10—C11—C12	121.1 (2)
C3—C4—C5	119.4 (2)	C10—C11—H11A	119.5
C3—C4—H4A	120.3	C12—C11—H11A	119.5
C5—C4—H4A	120.3	C13—C12—C11	120.2 (2)
C6—C5—C4	121.0 (2)	C13—C12—H12A	119.9
C6—C5—Cl2	118.98 (18)	C11—C12—H12A	119.9
C4—C5—Cl2	120.0 (2)	C14—C13—C12	119.7 (2)
O1—C6—C1	120.84 (19)	C14—C13—H13A	120.1
O1—C6—C5	120.90 (19)	C12—C13—H13A	120.1
C1—C6—C5	118.23 (19)	C13—C14—C15	120.1 (2)
O1—C7—C8	111.28 (15)	C13—C14—H14A	120.0
O1—C7—H7A	109.4	C15—C14—H14A	120.0
C8—C7—H7A	109.4	C10—C15—C14	120.9 (2)
O1—C7—H7B	109.4	C10—C15—H15A	119.5
C8—C7—H7B	109.4	C14—C15—H15A	119.5
H7A—C7—H7B	108.0

C6—C1—C2—C3	−0.4 (3)	C6—O1—C7—C8	−154.72 (17)
Cl1—C1—C2—C3	178.76 (18)	C9—N1—C8—O2	1.3 (3)
C1—C2—C3—C4	−0.9 (4)	C9—N1—C8—C7	−178.76 (19)
C2—C3—C4—C5	0.7 (4)	O1—C7—C8—O2	174.13 (18)
C3—C4—C5—C6	0.7 (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—C5	86.3 (2)	N1—C9—C10—C15	30.6 (3)
C2—C1—C6—O1	−176.57 (18)	C15—C10—C11—C12	0.9 (3)
Cl1—C1—C6—O1	4.3 (3)	C9—C10—C11—C12	−176.7 (2)
C2—C1—C6—C5	1.7 (3)	C10—C11—C12—C13	−1.1 (4)
Cl1—C1—C6—C5	−177.41 (15)	C11—C12—C13—C14	1.1 (4)
C4—C5—C6—O1	176.40 (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—C14	176.8 (2)
Cl2—C5—C6—C1	177.05 (16)	C13—C14—C15—C10	0.7 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.86	2.23	2.644 (2)	109
N1—H1A···O2ⁱ	0.86	2.31	2.970 (2)	133

Symmetry code: (i) −x+3/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃Cl₂NO₂
M_r	310.16
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	298
a, b, c (Å)	14.8886 (10), 8.6579 (6), 22.9867 (14)
V (Å³)	2963.1 (3)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.44
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.918, 0.958
No. of measured, independent and observed [I > 2σ(I)] reflections	16445, 3412, 2103
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.131, 1.02
No. of reflections	3412
No. of parameters	181
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.34

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
N1—H1A···O1	0.86	2.23	2.644 (2)	109
N1—H1A···O2ⁱ	0.86	2.31	2.970 (2)	133

Symmetry code: (i) −x+3/2, y+1/2, z.

Acknowledgements

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

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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar