Methyl 2-[2-(2,6-dichloro­anilino)phen­yl]acetate

The title compound, C₁₅H₁₃C_l2NO₂, exhibits intra­molecular hydrogen bonding between the amino N and meth­oxy O atoms, and no inter­molecular hydrogen bonding, contrary to previous studies. The dihedral angle between the two benzene rings is 74.99 (7)°.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.040
• wR factor = 0.099
• Data-to-parameter ratio = 17.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT352_ALERT_3_C Short   N-H Bond (0.87A)   N1     -   H1     ...       0.76 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   1 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: CrystalClear (Molecular Structure Corporation, 2001); cell refinement: CrystalClear; data reduction: TEXSAN (Rigaku/MSC, 2004); program(s) used to solve structure: TEXSAN; program(s) used to refine structure: TEXSAN; molecular graphics: TEXSAN; software used to prepare material for publication: TEXSAN.

Methyl 2-[2-(2,6-dichloroanilino)phenyl]acetate

Crystal data

C15H13Cl2NO2	Z = 2
Mr = 310.18	F(000) = 320.00
Triclinic, P1	Dx = 1.480 Mg m^−3
Hall symbol: -P 1	Melting point: 375 K
a = 8.542 (6) Å	Mo Kα radiation, λ = 0.7107 Å
b = 9.376 (7) Å	Cell parameters from 2161 reflections
c = 10.503 (8) Å	θ = 3.5–27.5°
α = 113.452 (5)°	µ = 0.47 mm^−1
β = 103.329 (4)°	T = 123 K
γ = 104.124 (5)°	Block, colourless
V = 695.8 (9) Å^3	0.30 × 0.30 × 0.30 mm

Data collection

Rigaku/MSC Mercury CCD area-detector diffractometer	Rint = 0.028
Detector resolution: 14.62 pixels mm^-1	θmax = 27.5°
ω scans	h = −10→11
5631 measured reflections	k = −12→7
3164 independent reflections	l = −12→13
2698 reflections with F^2 > 2σ(F^2)

Refinement

Refinement on F^2	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.040	w = 1/[σ^2(Fo^2) + {0.05[Max(Fo^2,0) + 2Fc^2]/3}^2]
wR(F^2) = 0.099	(Δ/σ)max = 0.002
S = 1.15	Δρmax = 0.26 e Å^−3
3164 reflections	Δρmin = −0.17 e Å^−3
185 parameters

Special details

Refinement. Refinement was carried out using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F². R-factor (gt) are based on F. The threshold expression of F² > 2.0 σ(F²) is used only for calculating R-factor (gt).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.86420 (6)	0.06539 (6)	0.84871 (6)	0.0267 (1)
Cl2	0.73133 (6)	0.62955 (5)	1.09344 (5)	0.0246 (1)
O1	0.2941 (2)	0.3669 (2)	0.4990 (2)	0.0366 (4)
O2	0.5292 (2)	0.4939 (2)	0.7092 (1)	0.0229 (3)
N1	0.6849 (2)	0.3017 (2)	0.8409 (2)	0.0159 (4)
C1	0.4941 (3)	0.6464 (2)	0.7553 (2)	0.0275 (5)
C2	0.4174 (2)	0.3627 (2)	0.5780 (2)	0.0199 (4)
C3	0.4664 (2)	0.2112 (2)	0.5457 (2)	0.0190 (4)
C4	0.4107 (2)	0.1249 (2)	0.6321 (2)	0.0155 (4)
C5	0.2453 (2)	−0.0001 (2)	0.5699 (2)	0.0202 (4)
C6	0.1900 (2)	−0.0835 (2)	0.6442 (2)	0.0226 (4)
C7	0.3031 (2)	−0.0437 (2)	0.7823 (2)	0.0198 (4)
C8	0.4671 (2)	0.0810 (2)	0.8472 (2)	0.0166 (4)
C9	0.5218 (2)	0.1692 (2)	0.7746 (2)	0.0143 (4)
C10	0.8038 (2)	0.3491 (2)	0.9815 (2)	0.0153 (4)
C11	0.8968 (2)	0.2512 (2)	1.0017 (2)	0.0188 (4)
C12	1.0156 (2)	0.2975 (2)	1.1399 (2)	0.0237 (5)
C13	1.0460 (2)	0.4460 (3)	1.2621 (2)	0.0262 (5)
C14	0.9604 (2)	0.5489 (2)	1.2467 (2)	0.0243 (5)
C15	0.8402 (2)	0.4998 (2)	1.1080 (2)	0.0186 (4)
H1	0.677 (3)	0.375 (3)	0.830 (2)	0.024 (6)*
H1A	0.4948	0.6832	0.6821	0.0328*
H1B	0.5820	0.7317	0.8499	0.0328*
H1C	0.3826	0.6251	0.7642	0.0328*
H3A	0.5900	0.2462	0.5733	0.0223*
H3B	0.4108	0.1332	0.4407	0.0223*
H5	0.1728	−0.0266	0.4798	0.0239*
H6	0.0823	−0.1623	0.6035	0.0263*
H7	0.2696	−0.0994	0.8302	0.0233*
H8	0.5389	0.1056	0.9369	0.0196*
H12	1.0723	0.2308	1.1498	0.0280*
H13	1.1219	0.4759	1.3519	0.0310*
H14	0.9823	0.6472	1.3260	0.0286*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.0278 (3)	0.0187 (2)	0.0315 (3)	0.0118 (2)	0.0088 (2)	0.0097 (2)
Cl2	0.0226 (2)	0.0198 (2)	0.0278 (3)	0.0103 (2)	0.0094 (2)	0.0067 (2)
O1	0.0380 (9)	0.0390 (9)	0.0321 (8)	0.0213 (7)	0.0020 (7)	0.0185 (7)
O2	0.0271 (7)	0.0171 (6)	0.0262 (7)	0.0109 (6)	0.0096 (6)	0.0107 (6)
N1	0.0174 (7)	0.0143 (7)	0.0169 (7)	0.0047 (6)	0.0043 (6)	0.0100 (6)
C1	0.038 (1)	0.0208 (9)	0.034 (1)	0.0158 (9)	0.0201 (9)	0.0156 (9)
C2	0.0251 (9)	0.0231 (9)	0.0186 (9)	0.0108 (8)	0.0111 (8)	0.0138 (8)
C3	0.0252 (9)	0.0193 (9)	0.0134 (8)	0.0098 (7)	0.0071 (7)	0.0079 (7)
C4	0.0196 (8)	0.0144 (8)	0.0136 (8)	0.0085 (7)	0.0071 (7)	0.0061 (7)
C5	0.0213 (9)	0.0175 (8)	0.0139 (8)	0.0066 (7)	0.0009 (7)	0.0038 (7)
C6	0.0166 (8)	0.0180 (9)	0.0238 (10)	0.0006 (7)	0.0041 (7)	0.0066 (7)
C7	0.0210 (9)	0.0189 (9)	0.0216 (9)	0.0057 (7)	0.0088 (7)	0.0121 (7)
C8	0.0182 (8)	0.0166 (8)	0.0143 (8)	0.0063 (7)	0.0040 (7)	0.0079 (7)
C9	0.0149 (8)	0.0119 (8)	0.0150 (8)	0.0060 (6)	0.0060 (7)	0.0045 (6)
C10	0.0125 (8)	0.0162 (8)	0.0168 (8)	0.0021 (6)	0.0053 (7)	0.0095 (7)
C11	0.0154 (8)	0.0177 (8)	0.0215 (9)	0.0028 (7)	0.0054 (7)	0.0105 (7)
C12	0.0154 (8)	0.0268 (10)	0.032 (1)	0.0059 (7)	0.0055 (8)	0.0200 (9)
C13	0.0161 (9)	0.035 (1)	0.0214 (10)	0.0007 (8)	0.0000 (7)	0.0165 (9)
C14	0.0183 (9)	0.0251 (10)	0.0188 (9)	0.0005 (7)	0.0044 (7)	0.0068 (8)
C15	0.0139 (8)	0.0197 (9)	0.0220 (9)	0.0048 (7)	0.0076 (7)	0.0103 (7)

Geometric parameters (Å, º)

Cl1—C11	1.739 (2)	C5—C6	1.386 (3)
Cl2—C15	1.733 (2)	C5—H5	0.899
O1—C2	1.201 (2)	C6—C7	1.387 (3)
O2—C1	1.447 (2)	C6—H6	0.900
O2—C2	1.340 (2)	C7—C8	1.385 (3)
N1—C9	1.411 (2)	C7—H7	0.900
N1—C10	1.405 (2)	C8—C9	1.401 (2)
N1—H1	0.75 (2)	C8—H8	0.899
C1—H1A	0.960	C10—C11	1.397 (2)
C1—H1B	0.960	C10—C15	1.400 (2)
C1—H1C	0.959	C11—C12	1.390 (3)
C2—C3	1.510 (3)	C12—C13	1.379 (3)
C3—C4	1.517 (2)	C12—H12	0.901
C3—H3A	0.959	C13—C14	1.380 (3)
C3—H3B	0.961	C13—H13	0.898
C4—C5	1.398 (3)	C14—C15	1.391 (3)
C4—C9	1.404 (2)	C14—H14	0.900
Cl2···C9^i	3.383 (2)	O2···C12^ii	3.526 (3)
Cl2···C8^i	3.466 (2)	N1···C14^ii	3.496 (3)
Cl2···C4^i	3.574 (2)	N1···C13^ii	3.546 (3)
Cl2···C11^ii	3.599 (3)	C3···C4^v	3.515 (3)
O1···C13^iii	3.322 (3)	C10···C15^ii	3.523 (3)
O1···O2^iv	3.405 (2)	C11···C15^ii	3.549 (3)
O1···C1^iv	3.534 (3)	C12···H1^ii	3.37 (2)
O1···C2^iv	3.557 (3)	C13···H1^ii	3.13 (2)
O2···C13^ii	3.455 (3)	C14···H1^ii	3.36 (2)
C1—O2—C2	116.4 (2)	C6—C7—C8	120.6 (2)
C9—N1—C10	121.8 (1)	C6—C7—H7	119.6
C9—N1—H1	110 (1)	C8—C7—H7	119.7
C10—N1—H1	113 (1)	C7—C8—C9	120.6 (2)
O2—C1—H1A	109.3	C7—C8—H8	119.6
O2—C1—H1B	109.4	C9—C8—H8	119.7
O2—C1—H1C	109.4	N1—C9—C4	119.1 (1)
H1A—C1—H1B	109.5	N1—C9—C8	121.9 (1)
H1A—C1—H1C	109.6	C4—C9—C8	119.0 (2)
H1B—C1—H1C	109.6	N1—C10—C11	121.8 (2)
O1—C2—O2	123.7 (2)	N1—C10—C15	121.9 (2)
O1—C2—C3	125.4 (2)	C11—C10—C15	116.2 (2)
O2—C2—C3	110.9 (1)	Cl1—C11—C10	119.1 (1)
C2—C3—C4	111.4 (1)	Cl1—C11—C12	118.6 (1)
C2—C3—H3A	109.0	C10—C11—C12	122.3 (2)
C2—C3—H3B	109.0	C11—C12—C13	119.5 (2)
C4—C3—H3A	109.0	C11—C12—H12	120.3
C4—C3—H3B	109.0	C13—C12—H12	120.2
H3A—C3—H3B	109.5	C12—C13—C14	120.2 (2)
C3—C4—C5	119.7 (2)	C12—C13—H13	119.8
C3—C4—C9	121.2 (2)	C14—C13—H13	120.0
C5—C4—C9	119.1 (2)	C13—C14—C15	119.6 (2)
C4—C5—C6	121.6 (2)	C13—C14—H14	120.2
C4—C5—H5	119.2	C15—C14—H14	120.2
C6—C5—H5	119.2	Cl2—C15—C10	119.5 (1)
C5—C6—C7	118.9 (2)	Cl2—C15—C14	118.4 (1)
C5—C6—H6	120.5	C10—C15—C14	122.1 (2)
C7—C6—H6	120.5
Cl1—C11—C10—N1	−0.2 (2)	C5—C4—C3—H3B	−31.3
Cl1—C11—C10—C15	−178.0 (1)	C5—C4—C9—C8	3.2 (2)
Cl1—C11—C12—C13	178.7 (1)	C5—C6—C7—C8	1.9 (3)
Cl1—C11—C12—H12	−1.4	C5—C6—C7—H7	−178.1
Cl2—C15—C10—N1	2.1 (2)	C6—C5—C4—C9	−1.4 (3)
Cl2—C15—C10—C11	179.9 (1)	C6—C7—C8—C9	0.0 (3)
Cl2—C15—C14—C13	178.5 (1)	C6—C7—C8—H8	179.8
Cl2—C15—C14—H14	−1.5	C7—C6—C5—H5	179.2
O1—C2—O2—C1	0.8 (3)	C8—C7—C6—H6	−178.1
O1—C2—C3—C4	−100.6 (2)	C8—C9—N1—C10	2.0 (2)
O1—C2—C3—H3A	139.1	C8—C9—N1—H1	−136 (1)
O1—C2—C3—H3B	19.7	C9—N1—C10—C11	73.3 (2)
O2—C2—C3—C4	78.6 (2)	C9—N1—C10—C15	−109.0 (2)
O2—C2—C3—H3A	−41.7	C9—C4—C3—H3A	29.8
O2—C2—C3—H3B	−161.1	C9—C4—C3—H3B	149.2
N1—C9—C4—C3	3.0 (2)	C9—C4—C5—H5	178.3
N1—C9—C4—C5	−176.5 (2)	C9—C8—C7—H7	−180.0
N1—C9—C8—C7	177.1 (2)	C10—C11—C12—C13	−1.0 (3)
N1—C9—C8—H8	−2.7	C10—C11—C12—H12	178.9
N1—C10—C11—C12	179.5 (2)	C10—C15—C14—C13	−0.8 (3)
N1—C10—C15—C14	−178.6 (2)	C10—C15—C14—H14	179.2
C1—O2—C2—C3	−178.5 (1)	C11—C10—N1—H1	−149 (1)
C2—O2—C1—H1A	−59.8	C11—C10—C15—C14	−0.8 (2)
C2—O2—C1—H1B	−179.7	C11—C12—C13—C14	−0.8 (3)
C2—O2—C1—H1C	60.2	C11—C12—C13—H13	179.4
C2—C3—C4—C5	88.9 (2)	C12—C11—C10—C15	1.7 (2)
C2—C3—C4—C9	−90.6 (2)	C12—C13—C14—C15	1.6 (3)
C3—C4—C5—C6	179.2 (2)	C12—C13—C14—H14	−178.4
C3—C4—C5—H5	−1.2	C14—C13—C12—H12	179.4
C3—C4—C9—C8	−177.3 (2)	C15—C10—N1—H1	28 (1)
C4—C5—C6—C7	−1.2 (3)	C15—C14—C13—H13	−178.5
C4—C5—C6—H6	178.8	H5—C5—C6—H6	−0.8
C4—C9—N1—C10	−178.3 (2)	H6—C6—C7—H7	1.9
C4—C9—N1—H1	43 (1)	H7—C7—C8—H8	−0.1
C4—C9—C8—C7	−2.6 (2)	H12—C12—C13—H13	−0.4
C4—C9—C8—H8	177.6	H13—C13—C14—H14	1.4
C5—C4—C3—H3A	−150.7	H13—C13—C14—H14	1.4

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+2; (iii) x−1, y, z−1; (iv) −x+1, −y+1, −z+1; (v) −x+1, −y, −z+1.

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.75 (2)	2.35 (2)	3.038 (2)	152 (1)