Crystal structure of ethyl 2-(4-chloro-anilino)acetate.

The title compound, C10H12ClNO2, is close to planar (r.m.s. deviation for the 14 non-H atoms = 0.053 Å). In the crystal, inversion dimers linked by pairs of N-H⋯Oc (c = carbox-yl) hydrogen bonds generate R 2 (2)(10) loops.

Related literature

For the biological activity of sydnone derivatives, see: Satheesha Rai et al. (2008 ▶); Patel & Patel (2012 ▶). For an overview of sydnone derivatives, see: Asundaria et al. (2010 ▶); Ding et al. (2013 ▶); Fadda & Elattar (2012 ▶). For a related structure, see: Zhang et al. (2010 ▶).

Experimental

Crystal data

C10H12ClNO2

M = 213.66

Triclinic,

a = 5.373 (5) Å

b = 7.575 (7) Å

c = 14.127 (12) Å

α = 75.83 (4)°

β = 87.73 (3)°

γ = 72.99 (3)°

V = 532.7 (9) Å3

Z = 2

Mo Kα radiation

μ = 0.33 mm−1

T = 296 K

0.40 × 0.36 × 0.29 mm

Data collection

Bruker X8 APEX CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009) ▶ T min = 0.693, T max = 0.747

3672 measured reflections

2361 independent reflections

1718 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.136

S = 1.03

2361 reflections

127 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.25 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814018297/hb7269sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814018297/hb7269Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814018297/hb7269Isup3.cml

Click here for additional data file.

. DOI: 10.1107/S1600536814018297/hb7269fig1.tif

Mol­ecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Click here for additional data file.

. DOI: 10.1107/S1600536814018297/hb7269fig2.tif

Part of the crystal structure of the title compound, showing hydrogen-bonded (dashed lines) dimers.

CCDC reference: 1018685

Additional supporting information: crystallographic information; 3D view; checkCIF report

C10H12ClNO2	Z = 2
Mr = 213.66	F(000) = 224
Triclinic, P1	Dx = 1.332 Mg m−3
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.373 (5) Å	Cell parameters from 2361 reflections
b = 7.575 (7) Å	θ = 2.9–27.5°
c = 14.127 (12) Å	µ = 0.33 mm−1
α = 75.83 (4)°	T = 296 K
β = 87.73 (3)°	Block, yellow
γ = 72.99 (3)°	0.40 × 0.36 × 0.29 mm
V = 532.7 (9) Å3

Bruker X8 APEX CCD diffractometer	2361 independent reflections
Radiation source: fine-focus sealed tube	1718 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
φ and ω scans	θmax = 27.5°, θmin = 2.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −6→6
Tmin = 0.693, Tmax = 0.747	k = −9→7
3672 measured reflections	l = −18→10

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.136	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0633P)2 + 0.1405P] where P = (Fo2 + 2Fc2)/3
2361 reflections	(Δ/σ)max < 0.001
127 parameters	Δρmax = 0.23 e Å−3
0 restraints	Δρmin = −0.25 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	0.2530 (4)	0.5821 (3)	0.17905 (14)	0.0493 (5)
C2	0.1089 (4)	0.5877 (3)	0.26135 (14)	0.0493 (5)
H2	−0.0633	0.6634	0.2564	0.059*
C3	0.2208 (3)	0.4803 (3)	0.35168 (14)	0.0460 (4)
H3	0.1234	0.4845	0.4074	0.055*
C4	0.4789 (3)	0.3659 (2)	0.35964 (13)	0.0408 (4)
C5	0.6209 (3)	0.3653 (3)	0.27463 (14)	0.0466 (4)
H5	0.7939	0.2912	0.2788	0.056*
C6	0.5104 (4)	0.4718 (3)	0.18512 (14)	0.0511 (5)
H6	0.6073	0.4700	0.1292	0.061*
C7	0.4644 (3)	0.2344 (3)	0.53739 (13)	0.0434 (4)
H7A	0.3204	0.1854	0.5300	0.052*
H7B	0.3945	0.3563	0.5536	0.052*
C8	0.6487 (3)	0.0983 (2)	0.61773 (13)	0.0421 (4)
C9	0.6934 (4)	−0.0457 (3)	0.78700 (13)	0.0494 (5)
H9A	0.8456	−0.0068	0.7962	0.059*
H9B	0.7510	−0.1735	0.7770	0.059*
C10	0.5267 (5)	−0.0410 (4)	0.87449 (15)	0.0683 (6)
H10A	0.6254	−0.1259	0.9314	0.102*
H10B	0.3772	−0.0802	0.8646	0.102*
H10C	0.4708	0.0861	0.8836	0.102*
N1	0.5998 (3)	0.2584 (3)	0.44760 (12)	0.0593 (5)
H1	0.7422	0.1814	0.4453	0.071*
O1	0.5353 (2)	0.08512 (18)	0.70336 (9)	0.0470 (3)
O2	0.8685 (3)	0.0108 (2)	0.60581 (10)	0.0620 (4)
Cl1	0.11032 (12)	0.71314 (11)	0.06510 (4)	0.0837 (3)

	U11	U22	U33	U12	U13	U23
C1	0.0484 (10)	0.0478 (10)	0.0434 (10)	−0.0104 (8)	−0.0067 (8)	0.0011 (8)
C2	0.0367 (9)	0.0459 (10)	0.0546 (11)	−0.0012 (8)	−0.0042 (8)	−0.0048 (8)
C3	0.0408 (9)	0.0471 (10)	0.0415 (10)	−0.0031 (8)	0.0042 (7)	−0.0071 (8)
C4	0.0377 (9)	0.0375 (9)	0.0417 (9)	−0.0052 (7)	−0.0013 (7)	−0.0062 (7)
C5	0.0359 (9)	0.0472 (10)	0.0480 (10)	−0.0025 (8)	0.0044 (7)	−0.0079 (8)
C6	0.0487 (10)	0.0553 (11)	0.0429 (10)	−0.0120 (9)	0.0060 (8)	−0.0048 (8)
C7	0.0422 (9)	0.0403 (9)	0.0413 (9)	−0.0030 (7)	0.0006 (7)	−0.0093 (7)
C8	0.0443 (10)	0.0376 (9)	0.0398 (9)	−0.0044 (8)	0.0018 (7)	−0.0101 (7)
C9	0.0471 (10)	0.0517 (11)	0.0402 (10)	−0.0044 (8)	−0.0025 (8)	−0.0058 (8)
C10	0.0728 (15)	0.0781 (15)	0.0406 (11)	−0.0065 (12)	0.0067 (10)	−0.0096 (10)
N1	0.0437 (9)	0.0669 (11)	0.0412 (9)	0.0132 (8)	0.0029 (7)	−0.0013 (8)
O1	0.0440 (7)	0.0480 (7)	0.0375 (7)	0.0006 (5)	0.0023 (5)	−0.0068 (5)
O2	0.0479 (8)	0.0668 (9)	0.0468 (8)	0.0120 (7)	0.0062 (6)	−0.0042 (7)
Cl1	0.0720 (4)	0.1006 (5)	0.0500 (4)	−0.0037 (3)	−0.0123 (3)	0.0101 (3)

C1—C2	1.373 (3)	C7—C8	1.500 (3)
C1—C6	1.384 (3)	C7—H7A	0.9700
C1—Cl1	1.742 (2)	C7—H7B	0.9700
C2—C3	1.385 (3)	C8—O2	1.202 (2)
C2—H2	0.9300	C8—O1	1.328 (2)
C3—C4	1.396 (3)	C9—O1	1.453 (2)
C3—H3	0.9300	C9—C10	1.499 (3)
C4—N1	1.374 (2)	C9—H9A	0.9700
C4—C5	1.397 (3)	C9—H9B	0.9700
C5—C6	1.372 (3)	C10—H10A	0.9600
C5—H5	0.9300	C10—H10B	0.9600
C6—H6	0.9300	C10—H10C	0.9600
C7—N1	1.436 (3)	N1—H1	0.8201
C2—C1—C6	120.88 (18)	C8—C7—H7B	109.8
C2—C1—Cl1	119.85 (16)	H7A—C7—H7B	108.2
C6—C1—Cl1	119.27 (16)	O2—C8—O1	124.56 (17)
C1—C2—C3	119.83 (18)	O2—C8—C7	124.41 (17)
C1—C2—H2	120.1	O1—C8—C7	111.03 (16)
C3—C2—H2	120.1	O1—C9—C10	107.18 (17)
C2—C3—C4	120.43 (17)	O1—C9—H9A	110.3
C2—C3—H3	119.8	C10—C9—H9A	110.3
C4—C3—H3	119.8	O1—C9—H9B	110.3
N1—C4—C3	122.69 (17)	C10—C9—H9B	110.3
N1—C4—C5	119.02 (17)	H9A—C9—H9B	108.5
C3—C4—C5	118.27 (16)	C9—C10—H10A	109.5
C6—C5—C4	121.34 (17)	C9—C10—H10B	109.5
C6—C5—H5	119.3	H10A—C10—H10B	109.5
C4—C5—H5	119.3	C9—C10—H10C	109.5
C5—C6—C1	119.24 (18)	H10A—C10—H10C	109.5
C5—C6—H6	120.4	H10B—C10—H10C	109.5
C1—C6—H6	120.4	C4—N1—C7	123.16 (16)
N1—C7—C8	109.52 (16)	C4—N1—H1	116.6
N1—C7—H7A	109.8	C7—N1—H1	117.7
C8—C7—H7A	109.8	C8—O1—C9	116.23 (15)
N1—C7—H7B	109.8

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.82	2.37	3.172 (3)	165

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.82	2.37	3.172 (3)	165

Symmetry code: (i) .