Methyl 3-[(3,5-dichloro-anilino)carbon-yl]propionate.

In the title compound, C(11)H(11)Cl(2)NO(3), the amide O atom and the carbonyl O atom of the ester segment are anti to each other and anti to the H atoms of the adjacent -CH(2) groups. In the crystal structure, mol-ecules are packed into centrosymmetric dimers through inter-molecular N-H⋯O hydrogen bonds. The dimers are linked into a layer structure extending parallel to (02) by C-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009 ▶).

Experimental

Crystal data

C11H11Cl2NO3

M = 276.11

Monoclinic,

a = 12.865 (2) Å

b = 14.753 (3) Å

c = 14.114 (2) Å

β = 109.59 (2)°

V = 2523.7 (7) Å3

Z = 8

Mo Kα radiation

μ = 0.51 mm−1

T = 299 K

0.50 × 0.16 × 0.12 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.785, T max = 0.941

4503 measured reflections

2259 independent reflections

1453 reflections with I > 2σ(I)

R int = 0.035

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.166

S = 1.09

2259 reflections

157 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.21 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810001455/ci5017sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810001455/ci5017Isup2.hkl

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

C11H11Cl2NO3	F(000) = 1136
Mr = 276.11	Dx = 1.453 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 1000 reflections
a = 12.865 (2) Å	θ = 3.0–28.1°
b = 14.753 (3) Å	µ = 0.51 mm−1
c = 14.114 (2) Å	T = 299 K
β = 109.59 (2)°	Needle, colourless
V = 2523.7 (7) Å3	0.50 × 0.16 × 0.12 mm
Z = 8

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	2259 independent reflections
Radiation source: fine-focus sealed tube	1453 reflections with I > 2σ(I)
graphite	Rint = 0.035
Rotation method data acquisition using ω and φ scans.	θmax = 25.4°, θmin = 3.0°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −11→15
Tmin = 0.785, Tmax = 0.941	k = −17→10
4503 measured reflections	l = −17→16

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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166	H atoms treated by a mixture of independent and constrained refinement
S = 1.09	w = 1/[σ2(Fo2) + (0.0595P)2 + 4.6291P] where P = (Fo2 + 2Fc2)/3
2259 reflections	(Δ/σ)max = 0.002
157 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.21 e Å−3

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.

	x	y	z	Uiso*/Ueq
C1	0.0757 (3)	0.6059 (3)	0.6618 (3)	0.0532 (9)
C2	0.0482 (3)	0.5146 (3)	0.6460 (3)	0.0591 (10)
H2	−0.0243	0.4975	0.6116	0.071*
C3	0.1280 (3)	0.4501 (3)	0.6814 (3)	0.0616 (11)
C4	0.2370 (3)	0.4721 (3)	0.7337 (3)	0.0627 (11)
H4	0.2906	0.4276	0.7580	0.075*
C5	0.2620 (3)	0.5621 (3)	0.7481 (3)	0.0583 (10)
C6	0.1848 (3)	0.6306 (3)	0.7149 (3)	0.0565 (10)
H6	0.2048	0.6911	0.7275	0.068*
C7	−0.0024 (3)	0.7610 (3)	0.6273 (3)	0.0560 (10)
C8	−0.1087 (3)	0.8104 (3)	0.5736 (3)	0.0603 (11)
H8A	−0.1369	0.7910	0.5040	0.072*
H8B	−0.1632	0.7953	0.6047	0.072*
C9	−0.0911 (3)	0.9108 (3)	0.5778 (3)	0.0624 (11)
H9A	−0.0324	0.9245	0.5512	0.075*
H9B	−0.0665	0.9298	0.6477	0.075*
C10	−0.1908 (3)	0.9652 (3)	0.5209 (3)	0.0551 (10)
C11	−0.2543 (4)	1.1146 (3)	0.4756 (4)	0.0849 (15)
H11A	−0.3094	1.1103	0.5074	0.102*
H11B	−0.2866	1.0998	0.4056	0.102*
H11C	−0.2258	1.1753	0.4824	0.102*
N1	−0.0090 (2)	0.6699 (2)	0.6230 (3)	0.0569 (9)
H1N	−0.072 (2)	0.645 (3)	0.595 (3)	0.068*
O1	0.0828 (2)	0.8016 (2)	0.6710 (3)	0.0875 (11)
O2	−0.2818 (2)	0.93505 (18)	0.4784 (2)	0.0668 (8)
O3	−0.1659 (2)	1.05231 (19)	0.5228 (2)	0.0754 (9)
Cl1	0.09280 (11)	0.33629 (8)	0.66222 (11)	0.0926 (5)
Cl2	0.39797 (8)	0.59326 (9)	0.81343 (10)	0.0845 (5)

	U11	U22	U33	U12	U13	U23
C1	0.0445 (19)	0.062 (2)	0.051 (2)	0.0079 (18)	0.0133 (17)	0.0045 (19)
C2	0.057 (2)	0.059 (3)	0.058 (2)	−0.0010 (19)	0.0150 (18)	−0.001 (2)
C3	0.067 (2)	0.056 (3)	0.064 (3)	0.010 (2)	0.024 (2)	0.004 (2)
C4	0.061 (2)	0.067 (3)	0.061 (3)	0.019 (2)	0.021 (2)	0.008 (2)
C5	0.048 (2)	0.070 (3)	0.056 (2)	0.0104 (19)	0.0149 (18)	0.002 (2)
C6	0.048 (2)	0.061 (2)	0.056 (2)	0.0050 (19)	0.0113 (18)	0.0050 (19)
C7	0.044 (2)	0.053 (2)	0.061 (3)	−0.0037 (18)	0.0048 (17)	0.0035 (19)
C8	0.045 (2)	0.057 (2)	0.066 (3)	−0.0019 (18)	0.0017 (18)	0.004 (2)
C9	0.045 (2)	0.058 (3)	0.072 (3)	−0.0013 (18)	0.0032 (19)	0.005 (2)
C10	0.052 (2)	0.054 (2)	0.055 (2)	−0.0041 (18)	0.0130 (18)	−0.0002 (19)
C11	0.096 (4)	0.058 (3)	0.101 (4)	0.018 (3)	0.033 (3)	0.010 (3)
N1	0.0402 (16)	0.055 (2)	0.065 (2)	−0.0013 (15)	0.0040 (15)	0.0031 (16)
O1	0.0455 (16)	0.0632 (19)	0.125 (3)	−0.0082 (14)	−0.0102 (16)	0.0064 (18)
O2	0.0458 (15)	0.0670 (18)	0.075 (2)	−0.0014 (13)	0.0035 (13)	0.0041 (15)
O3	0.0653 (18)	0.0543 (18)	0.095 (2)	0.0024 (14)	0.0120 (16)	0.0036 (16)
Cl1	0.0935 (9)	0.0592 (7)	0.1195 (12)	0.0048 (6)	0.0283 (8)	−0.0022 (7)
Cl2	0.0464 (6)	0.0885 (9)	0.1033 (10)	0.0137 (5)	0.0047 (6)	−0.0017 (7)

C1—C2	1.391 (5)	C7—C8	1.510 (5)
C1—C6	1.401 (5)	C8—C9	1.496 (5)
C1—N1	1.407 (5)	C8—H8A	0.97
C2—C3	1.366 (5)	C8—H8B	0.97
C2—H2	0.93	C9—C10	1.499 (5)
C3—C4	1.387 (6)	C9—H9A	0.97
C3—Cl1	1.736 (4)	C9—H9B	0.97
C4—C5	1.365 (6)	C10—O2	1.207 (4)
C4—H4	0.93	C10—O3	1.322 (4)
C5—C6	1.384 (5)	C11—O3	1.440 (5)
C5—Cl2	1.743 (4)	C11—H11A	0.96
C6—H6	0.93	C11—H11B	0.96
C7—O1	1.219 (4)	C11—H11C	0.96
C7—N1	1.347 (5)	N1—H1N	0.850 (19)
C2—C1—C6	119.5 (4)	C7—C8—H8A	109.4
C2—C1—N1	117.8 (3)	C9—C8—H8B	109.4
C6—C1—N1	122.7 (4)	C7—C8—H8B	109.4
C3—C2—C1	119.8 (4)	H8A—C8—H8B	108.0
C3—C2—H2	120.1	C8—C9—C10	114.7 (3)
C1—C2—H2	120.1	C8—C9—H9A	108.6
C2—C3—C4	122.2 (4)	C10—C9—H9A	108.6
C2—C3—Cl1	119.4 (3)	C8—C9—H9B	108.6
C4—C3—Cl1	118.3 (3)	C10—C9—H9B	108.6
C5—C4—C3	116.9 (4)	H9A—C9—H9B	107.6
C5—C4—H4	121.5	O2—C10—O3	123.8 (4)
C3—C4—H4	121.5	O2—C10—C9	125.6 (4)
C4—C5—C6	123.6 (4)	O3—C10—C9	110.6 (3)
C4—C5—Cl2	118.7 (3)	O3—C11—H11A	109.5
C6—C5—Cl2	117.7 (3)	O3—C11—H11B	109.5
C5—C6—C1	117.9 (4)	H11A—C11—H11B	109.5
C5—C6—H6	121.1	O3—C11—H11C	109.5
C1—C6—H6	121.1	H11A—C11—H11C	109.5
O1—C7—N1	123.0 (4)	H11B—C11—H11C	109.5
O1—C7—C8	121.8 (4)	C7—N1—C1	128.6 (3)
N1—C7—C8	115.2 (3)	C7—N1—H1N	119 (3)
C9—C8—C7	111.0 (3)	C1—N1—H1N	113 (3)
C9—C8—H8A	109.4	C10—O3—C11	117.5 (3)
C6—C1—C2—C3	−0.8 (6)	O1—C7—C8—C9	3.2 (6)
N1—C1—C2—C3	179.3 (4)	N1—C7—C8—C9	−176.8 (4)
C1—C2—C3—C4	0.4 (6)	C7—C8—C9—C10	176.4 (4)
C1—C2—C3—Cl1	179.5 (3)	C8—C9—C10—O2	4.0 (6)
C2—C3—C4—C5	−0.6 (6)	C8—C9—C10—O3	−175.6 (4)
Cl1—C3—C4—C5	−179.6 (3)	O1—C7—N1—C1	−2.7 (7)
C3—C4—C5—C6	1.1 (6)	C8—C7—N1—C1	177.3 (4)
C3—C4—C5—Cl2	−180.0 (3)	C2—C1—N1—C7	−178.9 (4)
C4—C5—C6—C1	−1.5 (6)	C6—C1—N1—C7	1.2 (6)
Cl2—C5—C6—C1	179.6 (3)	O2—C10—O3—C11	3.3 (6)
C2—C1—C6—C5	1.3 (6)	C9—C10—O3—C11	−177.0 (4)
N1—C1—C6—C5	−178.8 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O2i	0.85 (2)	2.17 (2)	3.017 (4)	172 (4)
C4—H4···O1ii	0.93	2.45	3.379 (5)	174

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O2i	0.85 (2)	2.17 (2)	3.017 (4)	172 (4)
C4—H4⋯O1ii	0.93	2.45	3.379 (5)	174

Symmetry codes: (i) ; (ii) .