Methyl 2-[2-(2,6-dichloro-anilino)-phenyl]-acetate.

In the title compound, C(15)H(13)Cl(2)NO(2), the dihedral angle between the aromatic rings is 63.80 (12)°. The conformation may be stabilized by a weak N-H⋯O hydrogen bond. In the crystal structure, a short C-Cl⋯π interaction occurs, with a Cl⋯π separation of 3.5706 (13) Å.

Related literature

For general background, see: Hashem et al. (2007 ▶); Husain et al. (2005 ▶). For bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C15H13Cl2NO2

M = 310.16

Monoclinic,

a = 4.9319 (4) Å

b = 20.0288 (14) Å

c = 14.5542 (10) Å

β = 97.711 (1)°

V = 1424.66 (18) Å3

Z = 4

Mo Kα radiation

μ = 0.46 mm−1

T = 173 (2) K

0.38 × 0.24 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.850, T max = 1.000 (expected range = 0.776–0.913)

8526 measured reflections

3423 independent reflections

2777 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.171

S = 1.04

3423 reflections

181 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.52 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995 ▶) and PLATON (Spek, 2003 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808038336/pv2122sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808038336/pv2122Isup2.hkl

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

C15H13Cl2NO2	F000 = 640
Mr = 310.16	Dx = 1.446 Mg m−3
Monoclinic, P21/n	Melting point: 331 K
Hall symbol: -P 2yn	Mo Kα radiation λ = 0.71073 Å
a = 4.9319 (4) Å	Cell parameters from 9949 reflections
b = 20.0288 (14) Å	θ = 2.4–28.3º
c = 14.5542 (10) Å	µ = 0.46 mm−1
β = 97.711 (1)º	T = 173 (2) K
V = 1424.66 (18) Å3	Block, pale yellow
Z = 4	0.38 × 0.24 × 0.20 mm

Bruker SMART APEXII CCD diffractometer	3423 independent reflections
Radiation source: fine-focus sealed tube	2777 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.020
T = 173(2) K	θmax = 28.3º
ω and φ scans	θmin = 2.5º
Absorption correction: multi-scan(SADABS; Bruker, 2005)	h = −6→6
Tmin = 0.850, Tmax = 1.000	k = −26→26
8526 measured reflections	l = −19→15

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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.171	w = 1/[σ2(Fo2) + (0.1042P)2 + 0.5254P] where P = (Fo2 + 2Fc2)/3
S = 1.04	(Δ/σ)max < 0.001
3423 reflections	Δρmax = 0.62 e Å−3
181 parameters	Δρmin = −0.52 e Å−3
Primary atom site location: structure-invariant direct methods	Extinction correction: none

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	0.8063 (4)	0.18670 (11)	0.42183 (15)	0.0459 (5)
C2	0.9559 (6)	0.23352 (14)	0.47685 (18)	0.0592 (7)
H2A	0.9401	0.2361	0.5411	0.071*
C3	1.1298 (6)	0.27691 (13)	0.4384 (2)	0.0646 (7)
H3A	1.2365	0.3084	0.4764	0.077*
C4	1.1462 (6)	0.27396 (11)	0.3451 (2)	0.0572 (6)
H4A	1.2586	0.3046	0.3178	0.069*
C5	0.9985 (5)	0.22618 (10)	0.29100 (16)	0.0454 (5)
C6	0.8295 (4)	0.17922 (9)	0.32730 (13)	0.0386 (4)
C7	0.6955 (4)	0.06202 (9)	0.29122 (13)	0.0360 (4)
C8	0.8988 (5)	0.03457 (12)	0.35515 (15)	0.0468 (5)
H8A	1.0348	0.0624	0.3879	0.056*
C9	0.9027 (6)	−0.03407 (14)	0.37114 (18)	0.0614 (7)
H9A	1.0410	−0.0529	0.4153	0.074*
C10	0.7088 (7)	−0.07451 (13)	0.3237 (2)	0.0676 (8)
H10A	0.7142	−0.1213	0.3347	0.081*
C11	0.5040 (5)	−0.04753 (12)	0.25957 (19)	0.0549 (6)
H11A	0.3696	−0.0759	0.2271	0.066*
C12	0.4948 (4)	0.02126 (10)	0.24258 (14)	0.0388 (4)
C13	0.2660 (4)	0.04998 (12)	0.17557 (15)	0.0434 (5)
H13A	0.1975	0.0907	0.2033	0.052*
H13B	0.1140	0.0173	0.1670	0.052*
C14	0.3438 (4)	0.06753 (10)	0.08154 (14)	0.0374 (4)
C15	0.1597 (4)	0.09199 (12)	−0.07671 (14)	0.0433 (5)
H15A	−0.0226	0.0958	−0.1125	0.065*
H15B	0.2626	0.0566	−0.1032	0.065*
H15C	0.2570	0.1345	−0.0789	0.065*
Cl1	0.57692 (13)	0.13766 (4)	0.47192 (4)	0.0602 (2)
Cl2	1.01835 (17)	0.22543 (3)	0.17271 (4)	0.0654 (2)
N1	0.6851 (4)	0.13126 (8)	0.27114 (12)	0.0425 (4)
H1A	0.5820	0.1447	0.2205	0.051*
O1	0.5844 (3)	0.07442 (10)	0.06748 (12)	0.0591 (5)
O2	0.1341 (3)	0.07623 (9)	0.01586 (12)	0.0550 (4)

	U11	U22	U33	U12	U13	U23
C1	0.0417 (11)	0.0525 (12)	0.0422 (11)	0.0138 (9)	0.0005 (8)	−0.0030 (9)
C2	0.0595 (15)	0.0663 (15)	0.0479 (12)	0.0187 (12)	−0.0069 (10)	−0.0198 (11)
C3	0.0656 (16)	0.0500 (13)	0.0718 (17)	0.0071 (11)	−0.0138 (13)	−0.0208 (12)
C4	0.0564 (14)	0.0363 (10)	0.0754 (17)	−0.0006 (9)	−0.0040 (12)	−0.0007 (10)
C5	0.0512 (12)	0.0358 (9)	0.0473 (11)	0.0055 (8)	−0.0006 (9)	0.0021 (8)
C6	0.0373 (10)	0.0373 (9)	0.0385 (10)	0.0064 (7)	−0.0048 (7)	−0.0008 (7)
C7	0.0370 (9)	0.0388 (9)	0.0331 (9)	0.0030 (7)	0.0075 (7)	0.0035 (7)
C8	0.0460 (11)	0.0554 (12)	0.0386 (10)	0.0100 (9)	0.0045 (8)	0.0072 (9)
C9	0.0735 (17)	0.0627 (15)	0.0506 (13)	0.0289 (13)	0.0176 (12)	0.0193 (11)
C10	0.097 (2)	0.0419 (12)	0.0690 (17)	0.0124 (13)	0.0313 (16)	0.0124 (11)
C11	0.0661 (15)	0.0420 (11)	0.0606 (14)	−0.0056 (10)	0.0230 (12)	0.0000 (10)
C12	0.0384 (10)	0.0412 (10)	0.0385 (10)	−0.0019 (7)	0.0111 (8)	0.0003 (7)
C13	0.0311 (9)	0.0565 (12)	0.0430 (11)	−0.0068 (8)	0.0073 (8)	−0.0036 (9)
C14	0.0286 (9)	0.0407 (9)	0.0436 (10)	−0.0040 (7)	0.0075 (7)	−0.0060 (8)
C15	0.0329 (10)	0.0601 (12)	0.0359 (10)	−0.0045 (8)	0.0005 (7)	0.0023 (8)
Cl1	0.0537 (4)	0.0771 (4)	0.0521 (4)	0.0141 (3)	0.0159 (3)	0.0074 (3)
Cl2	0.0911 (5)	0.0551 (4)	0.0509 (4)	−0.0072 (3)	0.0123 (3)	0.0118 (2)
N1	0.0489 (10)	0.0383 (8)	0.0363 (8)	−0.0016 (7)	−0.0084 (7)	0.0037 (6)
O1	0.0273 (7)	0.1015 (14)	0.0486 (9)	−0.0057 (7)	0.0057 (6)	0.0102 (9)
O2	0.0413 (8)	0.0703 (11)	0.0532 (10)	−0.0023 (7)	0.0060 (7)	−0.0026 (8)

C1—C2	1.381 (3)	C9—C10	1.367 (5)
C1—C6	1.404 (3)	C9—H9A	0.9500
C1—Cl1	1.731 (3)	C10—C11	1.390 (4)
C2—C3	1.390 (4)	C10—H10A	0.9500
C2—H2A	0.9500	C11—C12	1.399 (3)
C3—C4	1.371 (4)	C11—H11A	0.9500
C3—H3A	0.9500	C12—C13	1.503 (3)
C4—C5	1.383 (3)	C13—C14	1.511 (3)
C4—H4A	0.9500	C13—H13A	0.9900
C5—C6	1.406 (3)	C13—H13B	0.9900
C5—Cl2	1.738 (2)	C14—O1	1.239 (2)
C6—N1	1.393 (3)	C14—O2	1.322 (3)
C7—C8	1.387 (3)	C15—O2	1.406 (3)
C7—C12	1.400 (3)	C15—H15A	0.9800
C7—N1	1.417 (2)	C15—H15B	0.9800
C8—C9	1.394 (4)	C15—H15C	0.9800
C8—H8A	0.9500	N1—H1A	0.8800
C2—C1—C6	122.2 (2)	C9—C10—H10A	119.8
C2—C1—Cl1	118.01 (19)	C11—C10—H10A	119.8
C6—C1—Cl1	119.72 (17)	C10—C11—C12	120.3 (2)
C1—C2—C3	120.1 (2)	C10—C11—H11A	119.8
C1—C2—H2A	120.0	C12—C11—H11A	119.8
C3—C2—H2A	120.0	C11—C12—C7	118.7 (2)
C4—C3—C2	119.5 (2)	C11—C12—C13	119.7 (2)
C4—C3—H3A	120.2	C7—C12—C13	121.54 (18)
C2—C3—H3A	120.2	C12—C13—C14	114.64 (16)
C3—C4—C5	119.8 (3)	C12—C13—H13A	108.6
C3—C4—H4A	120.1	C14—C13—H13A	108.6
C5—C4—H4A	120.1	C12—C13—H13B	108.6
C4—C5—C6	122.8 (2)	C14—C13—H13B	108.6
C4—C5—Cl2	118.4 (2)	H13A—C13—H13B	107.6
C6—C5—Cl2	118.79 (16)	O1—C14—O2	122.7 (2)
N1—C6—C1	123.1 (2)	O1—C14—C13	122.73 (18)
N1—C6—C5	121.52 (19)	O2—C14—C13	114.61 (16)
C1—C6—C5	115.29 (19)	O2—C15—H15A	109.5
C8—C7—C12	120.44 (19)	O2—C15—H15B	109.5
C8—C7—N1	121.95 (19)	H15A—C15—H15B	109.5
C12—C7—N1	117.59 (17)	O2—C15—H15C	109.5
C7—C8—C9	119.7 (2)	H15A—C15—H15C	109.5
C7—C8—H8A	120.1	H15B—C15—H15C	109.5
C9—C8—H8A	120.1	C6—N1—C7	123.53 (16)
C10—C9—C8	120.5 (2)	C6—N1—H1A	118.2
C10—C9—H9A	119.8	C7—N1—H1A	118.2
C8—C9—H9A	119.8	C14—O2—C15	124.07 (17)
C9—C10—C11	120.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O1	0.88	2.64	3.152 (2)	118

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O1	0.88	2.64	3.152 (2)	118