Methyl N-(2,3-dichloro-phen-yl)succinamate.

The asymmetric unit of the title compound, C(11)H(11)Cl(2)NO(3), contains two independent mol-ecules. In both the molecules, the H atoms of the adjacent -CH(2) groups of the acid segments orient themselves away from the amide O and the carbonyl O atoms. The C=O and O-CH(3) bonds of the ester group are in syn positions with respect to each other. In the crystal, the mol-ecules are linked into infinite chains through inter-molecular N-H⋯O hydrogen bonds.

Related literature

For related structures, see: Gowda et al. (2009 ▶); Saraswathi et al. (2010 ▶).

Experimental

Crystal data

C11H11Cl2NO3

M = 276.11

Triclinic,

a = 4.7356 (5) Å

b = 15.868 (1) Å

c = 17.158 (2) Å

α = 80.748 (8)°

β = 88.869 (8)°

γ = 82.350 (8)°

V = 1261.2 (2) Å3

Z = 4

Mo Kα radiation

μ = 0.51 mm−1

T = 299 K

0.30 × 0.12 × 0.06 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.862, T max = 0.970

8311 measured reflections

4564 independent reflections

3398 reflections with I > 2σ(I)

R int = 0.019

Refinement

R[F 2 > 2σ(F 2)] = 0.054

wR(F 2) = 0.101

S = 1.16

4564 reflections

313 parameters

14 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.26 e Å−3

Δρmin = −0.25 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/S1600536810014844/ng2762sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810014844/ng2762Isup2.hkl

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

C11H11Cl2NO3	Z = 4
Mr = 276.11	F(000) = 568
Triclinic, P1	Dx = 1.454 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 4.7356 (5) Å	Cell parameters from 3119 reflections
b = 15.868 (1) Å	θ = 2.5–27.9°
c = 17.158 (2) Å	µ = 0.51 mm−1
α = 80.748 (8)°	T = 299 K
β = 88.869 (8)°	Needle, colourless
γ = 82.350 (8)°	0.30 × 0.12 × 0.06 mm
V = 1261.2 (2) Å3

Oxford Diffraction Xcalibur diffractometer with a Sapphire CCD detector	4564 independent reflections
Radiation source: fine-focus sealed tube	3398 reflections with I > 2σ(I)
graphite	Rint = 0.019
Rotation method data acquisition using ω and φ scans	θmax = 25.3°, θmin = 2.6°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	h = −5→4
Tmin = 0.862, Tmax = 0.970	k = −18→19
8311 measured reflections	l = −20→20

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.16	w = 1/[σ2(Fo2) + (0.0142P)2 + 1.3931P] where P = (Fo2 + 2Fc2)/3
4564 reflections	(Δ/σ)max < 0.001
313 parameters	Δρmax = 0.26 e Å−3
14 restraints	Δρmin = −0.25 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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
Cl1	−0.00812 (19)	−0.02952 (6)	0.23112 (5)	0.0573 (3)
Cl2	0.1692 (2)	−0.01708 (6)	0.40431 (5)	0.0666 (3)
O1	0.6129 (5)	0.1051 (2)	0.04979 (15)	0.0817 (9)
O2	0.3278 (7)	0.2834 (2)	−0.0451 (2)	0.0989 (11)
O3	0.6122 (6)	0.27365 (19)	−0.14800 (15)	0.0789 (9)
N1	0.1836 (5)	0.10541 (19)	0.10772 (16)	0.0474 (7)
H1N	0.008 (3)	0.101 (2)	0.1013 (19)	0.057*
C1	0.2772 (6)	0.1062 (2)	0.18535 (19)	0.0406 (7)
C2	0.1959 (6)	0.04796 (19)	0.24829 (18)	0.0375 (7)
C3	0.2808 (7)	0.0521 (2)	0.32437 (18)	0.0433 (8)
C4	0.4535 (7)	0.1112 (2)	0.3378 (2)	0.0543 (9)
H4	0.5130	0.1129	0.3888	0.065*
C5	0.5375 (7)	0.1676 (2)	0.2755 (2)	0.0580 (10)
H5	0.6564	0.2072	0.2845	0.070*
C6	0.4491 (7)	0.1667 (2)	0.1997 (2)	0.0501 (9)
H6	0.5040	0.2065	0.1582	0.060*
C7	0.3556 (7)	0.1087 (2)	0.04437 (19)	0.0503 (9)
C8	0.2087 (7)	0.1151 (3)	−0.03415 (19)	0.0586 (10)
H8A	0.0246	0.1500	−0.0333	0.070*
H8B	0.1766	0.0580	−0.0423	0.070*
C9	0.3833 (7)	0.1545 (2)	−0.10209 (19)	0.0546 (9)
H9A	0.5653	0.1187	−0.1038	0.065*
H9B	0.2846	0.1559	−0.1514	0.065*
C10	0.4338 (8)	0.2446 (3)	−0.0942 (2)	0.0581 (10)
C11	0.6685 (11)	0.3620 (3)	−0.1463 (3)	0.0965 (16)
H11A	0.4931	0.4004	−0.1536	0.116*
H11B	0.7986	0.3784	−0.1879	0.116*
H11C	0.7506	0.3651	−0.0963	0.116*
Cl3	1.3412 (2)	0.60860 (6)	0.49659 (5)	0.0574 (3)
Cl4	1.0827 (3)	0.78824 (7)	0.53909 (6)	0.0770 (3)
O4	0.7056 (4)	0.51729 (14)	0.32203 (15)	0.0534 (6)
O5	1.0323 (8)	0.4666 (2)	0.15611 (19)	0.1093 (12)
O6	0.7887 (8)	0.3579 (2)	0.15546 (19)	0.1027 (11)
N2	1.1105 (5)	0.56608 (16)	0.35184 (15)	0.0382 (6)
H2N	1.293 (2)	0.5544 (19)	0.3550 (18)	0.046*
C12	0.9873 (6)	0.64607 (18)	0.37103 (17)	0.0344 (7)
C13	1.0824 (6)	0.67383 (19)	0.43758 (17)	0.0362 (7)
C14	0.9662 (7)	0.7527 (2)	0.45638 (19)	0.0459 (8)
C15	0.7541 (8)	0.8036 (2)	0.4107 (2)	0.0570 (10)
H15	0.6754	0.8563	0.4239	0.068*
C16	0.6598 (8)	0.7758 (2)	0.3453 (2)	0.0591 (10)
H16	0.5158	0.8100	0.3143	0.071*
C17	0.7756 (7)	0.6981 (2)	0.3251 (2)	0.0482 (8)
H17	0.7111	0.6804	0.2802	0.058*
C18	0.9643 (6)	0.5063 (2)	0.33015 (17)	0.0368 (7)
C19	1.1431 (6)	0.4234 (2)	0.3189 (2)	0.0484 (9)
H19A	1.2006	0.3910	0.3703	0.058*
H19B	1.3143	0.4366	0.2902	0.058*
C20	0.9884 (7)	0.3681 (2)	0.2746 (2)	0.0492 (9)
H20A	1.0970	0.3112	0.2790	0.059*
H20B	0.8045	0.3618	0.2992	0.059*
C21	0.9442 (8)	0.4044 (3)	0.1895 (2)	0.0625 (10)
C22	0.7374 (15)	0.3858 (4)	0.0715 (3)	0.146 (2)
H22A	0.9162	0.3861	0.0441	0.175*
H22B	0.6340	0.4428	0.0630	0.175*
H22C	0.6281	0.3470	0.0517	0.175*

	U11	U22	U33	U12	U13	U23
Cl1	0.0583 (6)	0.0585 (6)	0.0607 (6)	−0.0252 (4)	0.0038 (4)	−0.0126 (4)
Cl2	0.0767 (7)	0.0689 (6)	0.0473 (5)	0.0011 (5)	0.0032 (5)	0.0024 (5)
O1	0.0267 (13)	0.167 (3)	0.0525 (16)	−0.0225 (16)	−0.0005 (11)	−0.0115 (17)
O2	0.101 (3)	0.107 (3)	0.103 (3)	−0.030 (2)	0.024 (2)	−0.047 (2)
O3	0.096 (2)	0.095 (2)	0.0502 (16)	−0.0474 (18)	0.0005 (15)	0.0019 (15)
N1	0.0255 (13)	0.072 (2)	0.0448 (16)	−0.0129 (14)	−0.0023 (12)	−0.0027 (14)
C1	0.0277 (16)	0.0483 (19)	0.0453 (19)	−0.0021 (14)	−0.0011 (14)	−0.0085 (15)
C2	0.0284 (16)	0.0369 (17)	0.0474 (19)	−0.0032 (13)	0.0020 (13)	−0.0086 (14)
C3	0.0401 (18)	0.0447 (19)	0.0422 (19)	0.0062 (15)	0.0024 (15)	−0.0086 (15)
C4	0.049 (2)	0.062 (2)	0.055 (2)	0.0006 (19)	−0.0076 (17)	−0.0232 (19)
C5	0.049 (2)	0.056 (2)	0.077 (3)	−0.0143 (18)	−0.0050 (19)	−0.028 (2)
C6	0.0427 (19)	0.046 (2)	0.062 (2)	−0.0095 (16)	0.0030 (17)	−0.0072 (17)
C7	0.0324 (18)	0.072 (2)	0.045 (2)	−0.0121 (17)	−0.0002 (15)	−0.0004 (17)
C8	0.0413 (19)	0.092 (3)	0.045 (2)	−0.0263 (19)	−0.0026 (16)	−0.0054 (19)
C9	0.051 (2)	0.081 (3)	0.0369 (19)	−0.0241 (19)	−0.0002 (16)	−0.0105 (18)
C10	0.048 (2)	0.086 (3)	0.041 (2)	−0.017 (2)	−0.0091 (17)	−0.006 (2)
C11	0.125 (4)	0.085 (3)	0.081 (3)	−0.052 (3)	−0.017 (3)	0.014 (3)
Cl3	0.0618 (6)	0.0576 (6)	0.0508 (5)	0.0042 (4)	−0.0204 (4)	−0.0103 (4)
Cl4	0.1133 (9)	0.0655 (6)	0.0601 (6)	−0.0138 (6)	0.0011 (6)	−0.0318 (5)
O4	0.0243 (12)	0.0540 (14)	0.0864 (18)	−0.0042 (10)	−0.0049 (11)	−0.0247 (13)
O5	0.153 (3)	0.105 (3)	0.079 (2)	−0.066 (3)	0.000 (2)	−0.002 (2)
O6	0.138 (3)	0.112 (3)	0.074 (2)	−0.059 (2)	−0.026 (2)	−0.0258 (19)
N2	0.0224 (12)	0.0433 (15)	0.0523 (16)	−0.0037 (12)	−0.0030 (12)	−0.0179 (13)
C12	0.0268 (15)	0.0348 (17)	0.0418 (17)	−0.0034 (13)	0.0033 (13)	−0.0076 (14)
C13	0.0317 (16)	0.0394 (17)	0.0375 (17)	−0.0066 (13)	0.0009 (13)	−0.0042 (14)
C14	0.055 (2)	0.0405 (19)	0.0450 (19)	−0.0094 (16)	0.0069 (16)	−0.0126 (15)
C15	0.057 (2)	0.0374 (19)	0.074 (3)	0.0035 (17)	0.010 (2)	−0.0105 (18)
C16	0.048 (2)	0.046 (2)	0.077 (3)	0.0041 (17)	−0.0098 (19)	0.0033 (19)
C17	0.0425 (19)	0.049 (2)	0.052 (2)	−0.0017 (16)	−0.0097 (16)	−0.0066 (16)
C18	0.0260 (16)	0.0455 (18)	0.0408 (17)	−0.0058 (14)	−0.0014 (13)	−0.0110 (14)
C19	0.0317 (17)	0.047 (2)	0.070 (2)	−0.0002 (15)	−0.0084 (16)	−0.0231 (17)
C20	0.0411 (19)	0.0398 (19)	0.071 (2)	−0.0047 (15)	−0.0029 (17)	−0.0211 (17)
C21	0.065 (3)	0.062 (3)	0.067 (3)	−0.015 (2)	0.001 (2)	−0.024 (2)
C22	0.186 (6)	0.181 (6)	0.086 (4)	−0.056 (5)	−0.026 (4)	−0.036 (4)

Cl1—C2	1.725 (3)	Cl3—C13	1.724 (3)
Cl2—C3	1.734 (3)	Cl4—C14	1.734 (3)
O1—C7	1.217 (4)	O4—C18	1.222 (3)
O2—C10	1.187 (4)	O5—C21	1.181 (5)
O3—C10	1.309 (4)	O6—C21	1.315 (4)
O3—C11	1.467 (5)	O6—C22	1.454 (6)
N1—C7	1.344 (4)	N2—C18	1.348 (4)
N1—C1	1.414 (4)	N2—C12	1.411 (4)
N1—H1N	0.852 (10)	N2—H2N	0.859 (10)
C1—C2	1.387 (4)	C12—C17	1.382 (4)
C1—C6	1.393 (4)	C12—C13	1.391 (4)
C2—C3	1.388 (4)	C13—C14	1.382 (4)
C3—C4	1.372 (5)	C14—C15	1.374 (5)
C4—C5	1.368 (5)	C15—C16	1.372 (5)
C4—H4	0.9300	C15—H15	0.9300
C5—C6	1.377 (5)	C16—C17	1.376 (5)
C5—H5	0.9300	C16—H16	0.9300
C6—H6	0.9300	C17—H17	0.9300
C7—C8	1.511 (4)	C18—C19	1.504 (4)
C8—C9	1.516 (4)	C19—C20	1.514 (4)
C8—H8A	0.9700	C19—H19A	0.9700
C8—H8B	0.9700	C19—H19B	0.9700
C9—C10	1.508 (5)	C20—C21	1.490 (5)
C9—H9A	0.9700	C20—H20A	0.9700
C9—H9B	0.9700	C20—H20B	0.9700
C11—H11A	0.9600	C22—H22A	0.9600
C11—H11B	0.9600	C22—H22B	0.9600
C11—H11C	0.9600	C22—H22C	0.9600
C10—O3—C11	114.9 (4)	C21—O6—C22	115.6 (4)
C7—N1—C1	123.9 (3)	C18—N2—C12	125.1 (2)
C7—N1—H1N	118 (2)	C18—N2—H2N	118 (2)
C1—N1—H1N	118 (2)	C12—N2—H2N	117 (2)
C2—C1—C6	119.1 (3)	C17—C12—C13	119.0 (3)
C2—C1—N1	120.8 (3)	C17—C12—N2	121.7 (3)
C6—C1—N1	120.1 (3)	C13—C12—N2	119.3 (3)
C1—C2—C3	119.8 (3)	C14—C13—C12	119.9 (3)
C1—C2—Cl1	119.6 (2)	C14—C13—Cl3	120.7 (2)
C3—C2—Cl1	120.6 (2)	C12—C13—Cl3	119.5 (2)
C4—C3—C2	120.6 (3)	C15—C14—C13	120.7 (3)
C4—C3—Cl2	118.8 (3)	C15—C14—Cl4	118.9 (3)
C2—C3—Cl2	120.6 (3)	C13—C14—Cl4	120.4 (3)
C5—C4—C3	119.4 (3)	C16—C15—C14	119.3 (3)
C5—C4—H4	120.3	C16—C15—H15	120.4
C3—C4—H4	120.3	C14—C15—H15	120.4
C4—C5—C6	121.1 (3)	C15—C16—C17	120.8 (3)
C4—C5—H5	119.4	C15—C16—H16	119.6
C6—C5—H5	119.4	C17—C16—H16	119.6
C5—C6—C1	119.8 (3)	C16—C17—C12	120.3 (3)
C5—C6—H6	120.1	C16—C17—H17	119.8
C1—C6—H6	120.1	C12—C17—H17	119.8
O1—C7—N1	122.4 (3)	O4—C18—N2	122.9 (3)
O1—C7—C8	122.1 (3)	O4—C18—C19	122.2 (3)
N1—C7—C8	115.5 (3)	N2—C18—C19	114.8 (2)
C7—C8—C9	111.8 (3)	C18—C19—C20	112.9 (3)
C7—C8—H8A	109.3	C18—C19—H19A	109.0
C9—C8—H8A	109.3	C20—C19—H19A	109.0
C7—C8—H8B	109.3	C18—C19—H19B	109.0
C9—C8—H8B	109.3	C20—C19—H19B	109.0
H8A—C8—H8B	107.9	H19A—C19—H19B	107.8
C10—C9—C8	111.9 (3)	C21—C20—C19	113.2 (3)
C10—C9—H9A	109.2	C21—C20—H20A	108.9
C8—C9—H9A	109.2	C19—C20—H20A	108.9
C10—C9—H9B	109.2	C21—C20—H20B	108.9
C8—C9—H9B	109.2	C19—C20—H20B	108.9
H9A—C9—H9B	107.9	H20A—C20—H20B	107.8
O2—C10—O3	124.7 (4)	O5—C21—O6	123.7 (4)
O2—C10—C9	124.3 (4)	O5—C21—C20	125.7 (4)
O3—C10—C9	111.0 (3)	O6—C21—C20	110.6 (3)
O3—C11—H11A	109.5	O6—C22—H22A	109.5
O3—C11—H11B	109.5	O6—C22—H22B	109.5
H11A—C11—H11B	109.5	H22A—C22—H22B	109.5
O3—C11—H11C	109.5	O6—C22—H22C	109.5
H11A—C11—H11C	109.5	H22A—C22—H22C	109.5
H11B—C11—H11C	109.5	H22B—C22—H22C	109.5
C7—N1—C1—C2	−133.2 (3)	C18—N2—C12—C17	−45.6 (4)
C7—N1—C1—C6	47.9 (5)	C18—N2—C12—C13	134.9 (3)
C6—C1—C2—C3	1.5 (4)	C17—C12—C13—C14	−0.4 (4)
N1—C1—C2—C3	−177.4 (3)	N2—C12—C13—C14	179.1 (3)
C6—C1—C2—Cl1	−178.1 (2)	C17—C12—C13—Cl3	178.7 (2)
N1—C1—C2—Cl1	3.1 (4)	N2—C12—C13—Cl3	−1.8 (4)
C1—C2—C3—C4	−2.5 (5)	C12—C13—C14—C15	1.0 (5)
Cl1—C2—C3—C4	177.1 (2)	Cl3—C13—C14—C15	−178.1 (3)
C1—C2—C3—Cl2	177.3 (2)	C12—C13—C14—Cl4	−179.9 (2)
Cl1—C2—C3—Cl2	−3.2 (4)	Cl3—C13—C14—Cl4	1.0 (4)
C2—C3—C4—C5	1.4 (5)	C13—C14—C15—C16	−0.7 (5)
Cl2—C3—C4—C5	−178.4 (3)	Cl4—C14—C15—C16	−179.7 (3)
C3—C4—C5—C6	0.7 (5)	C14—C15—C16—C17	−0.2 (6)
C4—C5—C6—C1	−1.7 (5)	C15—C16—C17—C12	0.8 (5)
C2—C1—C6—C5	0.6 (5)	C13—C12—C17—C16	−0.4 (5)
N1—C1—C6—C5	179.4 (3)	N2—C12—C17—C16	−179.9 (3)
C1—N1—C7—O1	6.6 (6)	C12—N2—C18—O4	2.8 (5)
C1—N1—C7—C8	−174.9 (3)	C12—N2—C18—C19	−175.4 (3)
O1—C7—C8—C9	−25.0 (5)	O4—C18—C19—C20	16.9 (5)
N1—C7—C8—C9	156.5 (3)	N2—C18—C19—C20	−164.9 (3)
C7—C8—C9—C10	−60.6 (4)	C18—C19—C20—C21	70.7 (4)
C11—O3—C10—O2	−2.4 (6)	C22—O6—C21—O5	2.2 (7)
C11—O3—C10—C9	178.4 (3)	C22—O6—C21—C20	−178.4 (4)
C8—C9—C10—O2	−6.7 (5)	C19—C20—C21—O5	4.6 (6)
C8—C9—C10—O3	172.5 (3)	C19—C20—C21—O6	−174.7 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.85 (1)	2.08 (1)	2.899 (3)	162 (3)
N2—H2N···O4ii	0.86 (1)	2.06 (2)	2.880 (3)	159 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.85 (1)	2.08 (1)	2.899 (3)	162 (3)
N2—H2N⋯O4ii	0.86 (1)	2.06 (2)	2.880 (3)	159 (3)

Symmetry codes: (i) ; (ii) .