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

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.

Key indicators

• Single-crystal X-ray study
• T = 298 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.045
• wR factor = 0.132
• Data-to-parameter ratio = 18.9

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S1. Experimental

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.

S2. Refinement

All 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.

Computing details

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

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

Crystal data

C15H13Cl2NO2	Dx = 1.391 Mg m^−3
Mr = 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) Å^3	Block, colorless
Z = 8	0.20 × 0.20 × 0.10 mm
F(000) = 1280

Data collection

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

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.131	H-atom parameters constrained
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0631P)^2 + 0.3666P] where P = (Fo^2 + 2Fc^2)/3
3412 reflections	(Δ/σ)max = 0.001
181 parameters	Δρmax = 0.20 e Å^−3
0 restraints	Δρmin = −0.34 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
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)

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)

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···O2^i	0.86	2.31	2.970 (2)	133

Symmetry code: (i) −x+3/2, y+1/2, z.