Methyl N-(4-chlorophenyl)succinamate.

In the structure of the title compound {systematic name: methyl 3-[(4-chloro-phen-yl)amino-carbon-yl]propionate}, C(11)H(12)ClNO(3), the conformations of the N-H and C=O bonds in the amide fragment are trans to each other and the conformations of the amide O atom and the carbonyl O atom of the ester fragment are also trans to the H atoms attached to the adjacent C atoms. Mol-ecules are linked into a centrosymmetric R(2) (2)(14) dimer by simple N-H⋯O inter-actions. Furthermore, a short intra-molecular C-H⋯O contact may stabilize the conformation adopted by the mol-ecule in the crystal.

Related literature

For background, see: Gowda et al. (2007 ▶); Gowda, Foro & Fuess (2008 ▶); Gowda, Foro, Sowmya et al. (2008 ▶); Jones et al. (1990 ▶); Wan et al. (2006 ▶). For related literature, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C11H12ClNO3

M = 241.67

Orthorhombic,

a = 14.190 (1) Å

b = 5.6370 (5) Å

c = 28.139 (3) Å

V = 2250.8 (4) Å3

Z = 8

Mo Kα radiation

μ = 0.33 mm−1

T = 299 (2) K

0.50 × 0.48 × 0.44 mm

Data collection

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007 ▶) T min = 0.852, T max = 0.868

10377 measured reflections

2272 independent reflections

1649 reflections with I > 2σ(I)

R int = 0.043

Refinement

R[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.154

S = 1.19

2272 reflections

173 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.28 e Å−3

Δρmin = −0.27 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2004 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2007 ▶); 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, 2003 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809002724/bx2194sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809002724/bx2194Isup2.hkl

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

C11H12ClNO3	F(000) = 1008
Mr = 241.67	Dx = 1.426 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 3422 reflections
a = 14.190 (1) Å	θ = 2.6–28.0°
b = 5.6370 (5) Å	µ = 0.33 mm−1
c = 28.139 (3) Å	T = 299 K
V = 2250.8 (4) Å3	Prism, colourless
Z = 8	0.50 × 0.48 × 0.44 mm

Oxford Diffraction Xcalibur diffractometer with Sapphire CCD detector	2272 independent reflections
Radiation source: fine-focus sealed tube	1649 reflections with I > 2σ(I)
graphite	Rint = 0.043
Rotation method data acquisition using ω and φ scans	θmax = 26.4°, θmin = 2.9°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2007)	h = −17→17
Tmin = 0.852, Tmax = 0.868	k = −7→7
10377 measured reflections	l = −33→35

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.050	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.154	w = 1/[σ2(Fo2) + (0.0501P)2 + 2.2683P] where P = (Fo2 + 2Fc2)/3
S = 1.19	(Δ/σ)max < 0.001
2272 reflections	Δρmax = 0.28 e Å−3
173 parameters	Δρmin = −0.27 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0109 (13)

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
Cl1	0.63844 (7)	1.51417 (17)	0.23361 (3)	0.0671 (3)
O1	0.67752 (18)	1.1013 (4)	0.00684 (8)	0.0659 (7)
O2	0.56516 (16)	0.4234 (4)	−0.09121 (8)	0.0591 (6)
O3	0.66393 (16)	0.6160 (5)	−0.13895 (8)	0.0635 (7)
N1	0.58842 (17)	0.9188 (5)	0.06256 (8)	0.0436 (6)
H1N	0.554 (2)	0.804 (6)	0.0675 (12)	0.052*
C1	0.60124 (18)	1.0708 (5)	0.10151 (9)	0.0384 (6)
C2	0.5627 (2)	1.0015 (6)	0.14469 (11)	0.0485 (7)
H2	0.525 (2)	0.866 (6)	0.1470 (11)	0.058*
C3	0.5731 (2)	1.1346 (6)	0.18498 (11)	0.0526 (8)
H3	0.546 (2)	1.083 (6)	0.2168 (12)	0.063*
C4	0.6234 (2)	1.3447 (5)	0.18267 (10)	0.0444 (7)
C5	0.6611 (2)	1.4180 (5)	0.14030 (11)	0.0439 (7)
H5	0.693 (2)	1.555 (6)	0.1384 (11)	0.053*
C6	0.65037 (19)	1.2848 (5)	0.09955 (11)	0.0423 (6)
H6	0.677 (2)	1.336 (6)	0.0706 (11)	0.051*
C7	0.62722 (19)	0.9364 (5)	0.01857 (10)	0.0399 (6)
C8	0.6017 (2)	0.7370 (5)	−0.01474 (10)	0.0418 (7)
H8A	0.532 (2)	0.724 (5)	−0.0177 (10)	0.050*
H8B	0.621 (2)	0.584 (6)	−0.0004 (11)	0.050*
C9	0.6451 (2)	0.7706 (6)	−0.06280 (10)	0.0448 (7)
H9A	0.712 (2)	0.773 (6)	−0.0601 (11)	0.054*
H9B	0.628 (2)	0.926 (6)	−0.0768 (11)	0.054*
C10	0.61912 (19)	0.5841 (5)	−0.09780 (10)	0.0417 (6)
C11	0.6445 (3)	0.4460 (7)	−0.17585 (12)	0.0674 (10)
H11A	0.6541	0.2885	−0.1638	0.081*
H11B	0.6861	0.4731	−0.2022	0.081*
H11C	0.5804	0.4629	−0.1862	0.081*

	U11	U22	U33	U12	U13	U23
Cl1	0.0874 (7)	0.0637 (6)	0.0502 (5)	−0.0054 (5)	0.0006 (4)	−0.0139 (4)
O1	0.0876 (17)	0.0558 (13)	0.0542 (13)	−0.0273 (13)	0.0239 (12)	−0.0081 (11)
O2	0.0642 (14)	0.0613 (14)	0.0520 (13)	−0.0215 (12)	0.0051 (10)	−0.0043 (11)
O3	0.0656 (14)	0.0797 (16)	0.0453 (12)	−0.0206 (13)	0.0149 (10)	−0.0109 (12)
N1	0.0475 (13)	0.0430 (14)	0.0403 (13)	−0.0096 (11)	0.0041 (10)	0.0028 (11)
C1	0.0374 (13)	0.0383 (14)	0.0396 (14)	0.0019 (11)	−0.0017 (11)	0.0051 (11)
C2	0.0546 (17)	0.0442 (16)	0.0467 (16)	−0.0106 (14)	0.0081 (13)	0.0033 (14)
C3	0.0629 (19)	0.0551 (19)	0.0398 (15)	−0.0065 (15)	0.0114 (14)	0.0034 (14)
C4	0.0473 (15)	0.0424 (16)	0.0436 (15)	0.0063 (13)	−0.0007 (12)	−0.0023 (12)
C5	0.0423 (15)	0.0366 (15)	0.0527 (17)	−0.0003 (12)	0.0028 (13)	−0.0003 (13)
C6	0.0444 (14)	0.0382 (15)	0.0442 (15)	−0.0025 (12)	0.0031 (12)	0.0071 (12)
C7	0.0392 (14)	0.0404 (15)	0.0401 (14)	0.0030 (12)	0.0031 (11)	0.0032 (12)
C8	0.0409 (14)	0.0426 (16)	0.0419 (15)	−0.0018 (13)	−0.0015 (12)	0.0014 (12)
C9	0.0440 (15)	0.0489 (17)	0.0415 (15)	−0.0067 (13)	0.0010 (12)	−0.0011 (13)
C10	0.0386 (14)	0.0468 (16)	0.0396 (14)	0.0019 (13)	−0.0003 (11)	0.0000 (12)
C11	0.068 (2)	0.085 (3)	0.0490 (18)	−0.007 (2)	0.0084 (16)	−0.0178 (18)

Cl1—C4	1.736 (3)	C4—C5	1.371 (4)
O1—C7	1.217 (3)	C5—C6	1.379 (4)
O2—C10	1.200 (3)	C5—H5	0.90 (3)
O3—C10	1.333 (3)	C6—H6	0.94 (3)
O3—C11	1.440 (4)	C7—C8	1.507 (4)
N1—C7	1.358 (4)	C8—C9	1.498 (4)
N1—C1	1.403 (4)	C8—H8A	1.00 (3)
N1—H1N	0.82 (3)	C8—H8B	0.99 (3)
C1—C2	1.388 (4)	C9—C10	1.487 (4)
C1—C6	1.395 (4)	C9—H9A	0.95 (3)
C2—C3	1.367 (4)	C9—H9B	0.99 (3)
C2—H2	0.94 (3)	C11—H11A	0.9600
C3—C4	1.384 (4)	C11—H11B	0.9600
C3—H3	1.01 (3)	C11—H11C	0.9600
C10—O3—C11	116.4 (3)	O1—C7—C8	122.8 (3)
C7—N1—C1	127.9 (2)	N1—C7—C8	114.5 (2)
C7—N1—H1N	117 (2)	C9—C8—C7	111.6 (2)
C1—N1—H1N	115 (2)	C9—C8—H8A	110.0 (17)
C2—C1—C6	118.3 (3)	C7—C8—H8A	110.2 (17)
C2—C1—N1	117.4 (3)	C9—C8—H8B	111.4 (18)
C6—C1—N1	124.2 (2)	C7—C8—H8B	109.3 (18)
C3—C2—C1	121.9 (3)	H8A—C8—H8B	104 (2)
C3—C2—H2	117 (2)	C10—C9—C8	114.0 (2)
C1—C2—H2	121 (2)	C10—C9—H9A	108.0 (19)
C2—C3—C4	119.1 (3)	C8—C9—H9A	109.9 (19)
C2—C3—H3	122.3 (19)	C10—C9—H9B	107.4 (19)
C4—C3—H3	118.6 (19)	C8—C9—H9B	111.6 (19)
C5—C4—C3	120.0 (3)	H9A—C9—H9B	106 (3)
C5—C4—Cl1	120.3 (2)	O2—C10—O3	122.7 (3)
C3—C4—Cl1	119.7 (2)	O2—C10—C9	126.1 (3)
C4—C5—C6	121.0 (3)	O3—C10—C9	111.2 (2)
C4—C5—H5	121 (2)	O3—C11—H11A	109.5
C6—C5—H5	118 (2)	O3—C11—H11B	109.5
C5—C6—C1	119.6 (3)	H11A—C11—H11B	109.5
C5—C6—H6	120.5 (19)	O3—C11—H11C	109.5
C1—C6—H6	119.9 (19)	H11A—C11—H11C	109.5
O1—C7—N1	122.7 (3)	H11B—C11—H11C	109.5
C7—N1—C1—C2	−172.7 (3)	N1—C1—C6—C5	−178.2 (3)
C7—N1—C1—C6	6.9 (4)	C1—N1—C7—O1	−3.2 (5)
C6—C1—C2—C3	−1.1 (5)	C1—N1—C7—C8	177.7 (3)
N1—C1—C2—C3	178.6 (3)	O1—C7—C8—C9	−0.4 (4)
C1—C2—C3—C4	0.0 (5)	N1—C7—C8—C9	178.7 (3)
C2—C3—C4—C5	0.7 (5)	C7—C8—C9—C10	−177.6 (2)
C2—C3—C4—Cl1	−179.2 (3)	C11—O3—C10—O2	−0.1 (4)
C3—C4—C5—C6	−0.4 (4)	C11—O3—C10—C9	−180.0 (3)
Cl1—C4—C5—C6	179.6 (2)	C8—C9—C10—O2	3.6 (4)
C4—C5—C6—C1	−0.7 (4)	C8—C9—C10—O3	−176.5 (3)
C2—C1—C6—C5	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1	0.94 (3)	2.22 (3)	2.833 (4)	121 (3)
N1—H1N···O2i	0.82 (3)	2.22 (3)	3.020 (3)	163 (3)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1	0.94 (3)	2.22 (3)	2.833 (4)	121 (3)
N1—H1N⋯O2i	0.82 (3)	2.22 (3)	3.020 (3)	163 (3)

Symmetry code: (i) .