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The title compound, C15H13Cl2NO2, 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)°.
Supporting information
CCDC reference: 640353
Key indicators
- Single-crystal X-ray study
- T = 123 K
- Mean (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
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
top
Crystal data top
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) Å3 | 0.30 × 0.30 × 0.30 mm |
Data collection top
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 F2 > 2σ(F2) | |
Refinement top
Refinement on F2 | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.040 | w = 1/[σ2(Fo2) + {0.05[Max(Fo2,0) + 2Fc2]/3}2] |
wR(F2) = 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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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···C9i | 3.383 (2) | O2···C12ii | 3.526 (3) |
Cl2···C8i | 3.466 (2) | N1···C14ii | 3.496 (3) |
Cl2···C4i | 3.574 (2) | N1···C13ii | 3.546 (3) |
Cl2···C11ii | 3.599 (3) | C3···C4v | 3.515 (3) |
O1···C13iii | 3.322 (3) | C10···C15ii | 3.523 (3) |
O1···O2iv | 3.405 (2) | C11···C15ii | 3.549 (3) |
O1···C1iv | 3.534 (3) | C12···H1ii | 3.37 (2) |
O1···C2iv | 3.557 (3) | C13···H1ii | 3.13 (2) |
O2···C13ii | 3.455 (3) | C14···H1ii | 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) top
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) |
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