Literature DB >> 21200895

Isopropyl 2-[2-(2,6-dichloro-anilino)phen-yl]acetate.

Hamid Nawaz, M Khawar Rauf, Masahiro Ebihara, Amin Badshah.   

Abstract

In the title compound, C(17)H(17)Cl(2)NO(2), the NH group exhibits an intra-molecular hydrogen bond to the carbonyl O atom and no inter-molecular hydrogen bonding, in contrast with previous studies. The dihedral angle between the two benzene rings is 58.57 (5)°. The ester group is planar, the greatest deviation from planarity being 0.0135 (11) Å for the ether O atom.

Entities:  

Year:  2007        PMID： 21200895      PMCID： PMC2915375          DOI： 10.1107/S1600536807065154

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For related literature, see: Abo-Ghalia et al. (1999 ▶); Alvarez-Larena et al. (1992 ▶); Corell et al. (1979 ▶); Evens (1979 ▶); Kass (1982 ▶); Lipka (1978 ▶, 1980 ▶); Moser et al. (1990 ▶); Robinson (1977 ▶); Scherrer & Whitehouse (1974 ▶).

Experimental

Crystal data

C17H17Cl2NO2 M = 338.22 Monoclinic, a = 17.548 (6) Å b = 9.443 (3) Å c = 9.719 (3) Å β = 93.959 (4)° V = 1606.7 (9) Å3 Z = 4 Mo Kα radiation μ = 0.41 mm−1 T = 123 (2) K 0.45 × 0.25 × 0.15 mm

Data collection

Rigaku/MSC Mercury CCD diffractometer Absorption correction: none 12744 measured reflections 3670 independent reflections 3428 reflections with I > 2σ(I) R int = 0.061

Refinement

R[F 2 > 2σ(F 2)] = 0.038 wR(F 2) = 0.093 S = 1.10 3670 reflections 205 parameters H atoms treated by a mixture of independent and constrained refinement Δρmax = 0.31 e Å−3 Δρmin = −0.32 e Å−3 Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2001 ▶); cell refinement: CrystalClear; data reduction: TEXSAN (Molecular Structure Corporation & Rigaku, 2004 ▶); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997 ▶); molecular graphics: ORTEPII (Johnson, 1976 ▶); software used to prepare material for publication: SHELXL97 and TEXSAN. Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536807065154/ez2110sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536807065154/ez2110Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H17Cl2NO2F000 = 704
Mr = 338.22Dx = 1.398 Mg m−3
Monoclinic, P21/cMelting point: 363 K
Hall symbol: -P 2ybcMo Kα radiation λ = 0.71070 Å
a = 17.548 (6) ÅCell parameters from 4977 reflections
b = 9.443 (3) Åθ = 3.0–27.5º
c = 9.719 (3) ŵ = 0.41 mm−1
β = 93.959 (4)ºT = 123 (2) K
V = 1606.7 (9) Å3Block, colorless
Z = 40.45 × 0.25 × 0.15 mm
Rigaku/MSC Mercury CCD diffractometer3670 independent reflections
Radiation source: fine-focus sealed tube3428 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.061
Detector resolution: 14.62 pixels mm-1θmax = 27.5º
T = 123(2) Kθmin = 3.0º
ω scansh = −16→22
Absorption correction: nonek = −12→12
12744 measured reflectionsl = −11→12
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.038H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.093  w = 1/[σ2(Fo2) + (0.0391P)2 + 0.7365P] where P = (Fo2 + 2Fc2)/3
S = 1.10(Δ/σ)max = 0.002
3670 reflectionsΔρmax = 0.31 e Å−3
205 parametersΔρmin = −0.32 e Å−3
Primary atom site location: structure-invariant direct methodsExtinction 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.
xyzUiso*/Ueq
N10.20829 (8)0.00238 (14)0.81278 (14)0.0176 (3)
H10.2551 (14)−0.036 (2)0.822 (2)0.041 (6)*
C10.15347 (8)−0.07425 (15)0.87884 (15)0.0150 (3)
C20.07450 (9)−0.06102 (15)0.84548 (15)0.0152 (3)
C30.02096 (9)−0.13894 (16)0.91175 (16)0.0178 (3)
H3−0.0320−0.12440.88930.021*
C40.04477 (9)−0.23810 (16)1.01071 (16)0.0192 (3)
H40.0083−0.29031.05770.023*
C50.12211 (9)−0.26066 (17)1.04063 (16)0.0188 (3)
H50.1390−0.33131.10530.023*
C60.17464 (8)−0.17985 (16)0.97592 (15)0.0158 (3)
Cl10.04071 (2)0.05250 (4)0.71474 (4)0.01864 (11)
Cl20.27143 (2)−0.21169 (4)1.01691 (4)0.02223 (11)
C70.20896 (8)0.15202 (16)0.80276 (15)0.0163 (3)
C80.16317 (9)0.23666 (17)0.88131 (16)0.0185 (3)
H80.13210.19380.94590.022*
C90.16256 (9)0.38265 (17)0.86589 (17)0.0214 (3)
H90.13060.43900.91890.026*
C100.20854 (10)0.44656 (17)0.77316 (17)0.0233 (3)
H100.20790.54650.76160.028*
C110.25537 (9)0.36304 (17)0.69773 (16)0.0214 (3)
H110.28740.40710.63550.026*
C120.25671 (9)0.21573 (16)0.71063 (15)0.0172 (3)
C130.30776 (9)0.12827 (18)0.62396 (16)0.0201 (3)
H13A0.27790.04920.58060.024*
H13B0.32620.18800.54940.024*
C140.37563 (9)0.06929 (17)0.71054 (17)0.0211 (3)
O10.37023 (7)−0.01740 (15)0.80056 (15)0.0362 (3)
O20.44207 (6)0.12335 (12)0.67675 (11)0.0209 (2)
C150.51089 (9)0.07400 (18)0.75893 (17)0.0225 (3)
H150.5055−0.02870.78140.027*
C160.52004 (11)0.1592 (2)0.89044 (19)0.0337 (4)
H16A0.52870.25880.86810.051*
H16B0.56380.12310.94820.051*
H16C0.47360.15090.94040.051*
C170.57594 (10)0.0941 (3)0.6674 (2)0.0390 (5)
H17A0.56590.03960.58220.059*
H17B0.62360.06110.71550.059*
H17C0.58060.19480.64480.059*
U11U22U33U12U13U23
N10.0136 (6)0.0152 (6)0.0242 (7)0.0011 (5)0.0032 (5)0.0029 (5)
C10.0168 (7)0.0137 (7)0.0148 (7)−0.0001 (5)0.0019 (5)−0.0018 (5)
C20.0168 (7)0.0130 (7)0.0156 (7)0.0017 (5)−0.0004 (5)−0.0017 (5)
C30.0141 (7)0.0179 (7)0.0213 (7)−0.0011 (6)0.0013 (6)−0.0042 (6)
C40.0203 (8)0.0180 (7)0.0195 (7)−0.0039 (6)0.0039 (6)−0.0009 (6)
C50.0234 (8)0.0165 (7)0.0163 (7)0.0000 (6)0.0005 (6)0.0007 (6)
C60.0134 (7)0.0171 (7)0.0165 (7)0.0015 (6)−0.0016 (5)−0.0023 (6)
Cl10.01741 (19)0.01788 (18)0.02003 (19)0.00138 (13)−0.00299 (13)0.00181 (13)
Cl20.01558 (19)0.0220 (2)0.0285 (2)0.00267 (14)−0.00263 (14)0.00416 (15)
C70.0132 (7)0.0175 (7)0.0174 (7)−0.0012 (6)−0.0041 (5)0.0022 (6)
C80.0158 (7)0.0205 (7)0.0189 (7)−0.0024 (6)−0.0016 (6)−0.0004 (6)
C90.0195 (8)0.0204 (7)0.0235 (8)0.0015 (6)−0.0052 (6)−0.0043 (6)
C100.0270 (9)0.0158 (7)0.0258 (8)−0.0025 (6)−0.0069 (7)0.0021 (6)
C110.0211 (8)0.0218 (8)0.0207 (8)−0.0054 (6)−0.0043 (6)0.0053 (6)
C120.0135 (7)0.0219 (8)0.0157 (7)−0.0011 (6)−0.0034 (5)0.0022 (6)
C130.0151 (7)0.0260 (8)0.0191 (7)−0.0005 (6)0.0013 (6)0.0042 (6)
C140.0158 (7)0.0252 (8)0.0224 (8)−0.0001 (6)0.0022 (6)0.0021 (6)
O10.0168 (6)0.0452 (8)0.0467 (8)0.0018 (6)0.0022 (5)0.0264 (7)
O20.0131 (5)0.0285 (6)0.0207 (6)−0.0007 (4)−0.0005 (4)0.0053 (5)
C150.0133 (8)0.0284 (8)0.0252 (8)0.0000 (6)−0.0037 (6)0.0064 (7)
C160.0332 (10)0.0355 (10)0.0307 (10)−0.0012 (8)−0.0100 (8)0.0013 (8)
C170.0145 (8)0.0663 (14)0.0363 (10)0.0045 (9)0.0022 (7)0.0140 (10)
N1—C11.3952 (19)C10—C111.385 (2)
N1—C71.416 (2)C10—H100.9500
N1—H10.90 (2)C11—C121.397 (2)
C1—C61.405 (2)C11—H110.9500
C1—C21.407 (2)C12—C131.516 (2)
C2—C31.387 (2)C13—C141.516 (2)
C2—Cl11.7354 (15)C13—H13A0.9900
C3—C41.386 (2)C13—H13B0.9900
C3—H30.9500C14—O11.207 (2)
C4—C51.385 (2)C14—O21.3344 (19)
C4—H40.9500O2—C151.4766 (19)
C5—C61.381 (2)C15—C171.507 (2)
C5—H50.9500C15—C161.509 (3)
C6—Cl21.7438 (16)C15—H151.0000
C7—C81.397 (2)C16—H16A0.9800
C7—C121.403 (2)C16—H16B0.9800
C8—C91.387 (2)C16—H16C0.9800
C8—H80.9500C17—H17A0.9800
C9—C101.388 (2)C17—H17B0.9800
C9—H90.9500C17—H17C0.9800
C1—N1—C7123.94 (13)C10—C11—H11119.1
C1—N1—H1113.5 (15)C12—C11—H11119.1
C7—N1—H1113.6 (15)C11—C12—C7118.50 (14)
N1—C1—C6121.23 (14)C11—C12—C13119.98 (14)
N1—C1—C2123.19 (14)C7—C12—C13121.51 (14)
C6—C1—C2115.36 (13)C14—C13—C12111.31 (13)
C3—C2—C1122.29 (14)C14—C13—H13A109.4
C3—C2—Cl1117.36 (12)C12—C13—H13A109.4
C1—C2—Cl1120.33 (11)C14—C13—H13B109.4
C4—C3—C2119.96 (14)C12—C13—H13B109.4
C4—C3—H3120.0H13A—C13—H13B108.0
C2—C3—H3120.0O1—C14—O2123.47 (15)
C5—C4—C3119.59 (14)O1—C14—C13123.62 (15)
C5—C4—H4120.2O2—C14—C13112.90 (13)
C3—C4—H4120.2C14—O2—C15116.23 (12)
C6—C5—C4119.65 (14)O2—C15—C17105.38 (14)
C6—C5—H5120.2O2—C15—C16108.97 (14)
C4—C5—H5120.2C17—C15—C16113.10 (16)
C5—C6—C1122.97 (14)O2—C15—H15109.8
C5—C6—Cl2118.09 (12)C17—C15—H15109.8
C1—C6—Cl2118.94 (12)C16—C15—H15109.8
C8—C7—C12119.65 (14)C15—C16—H16A109.5
C8—C7—N1121.69 (14)C15—C16—H16B109.5
C12—C7—N1118.66 (14)H16A—C16—H16B109.5
C9—C8—C7120.67 (15)C15—C16—H16C109.5
C9—C8—H8119.7H16A—C16—H16C109.5
C7—C8—H8119.7H16B—C16—H16C109.5
C8—C9—C10120.12 (15)C15—C17—H17A109.5
C8—C9—H9119.9C15—C17—H17B109.5
C10—C9—H9119.9H17A—C17—H17B109.5
C11—C10—C9119.25 (15)C15—C17—H17C109.5
C11—C10—H10120.4H17A—C17—H17C109.5
C9—C10—H10120.4H17B—C17—H17C109.5
C10—C11—C12121.78 (15)
C7—N1—C1—C6−130.59 (16)N1—C7—C8—C9−177.48 (14)
C7—N1—C1—C255.1 (2)C7—C8—C9—C10−0.9 (2)
N1—C1—C2—C3179.53 (14)C8—C9—C10—C11−0.7 (2)
C6—C1—C2—C34.9 (2)C9—C10—C11—C121.1 (2)
N1—C1—C2—Cl11.1 (2)C10—C11—C12—C70.1 (2)
C6—C1—C2—Cl1−173.52 (11)C10—C11—C12—C13178.82 (14)
C1—C2—C3—C4−2.7 (2)C8—C7—C12—C11−1.7 (2)
Cl1—C2—C3—C4175.78 (12)N1—C7—C12—C11177.93 (13)
C2—C3—C4—C5−1.3 (2)C8—C7—C12—C13179.61 (13)
C3—C4—C5—C62.8 (2)N1—C7—C12—C13−0.8 (2)
C4—C5—C6—C1−0.3 (2)C11—C12—C13—C14107.44 (16)
C4—C5—C6—Cl2179.91 (12)C7—C12—C13—C14−73.86 (18)
N1—C1—C6—C5−178.14 (14)C12—C13—C14—O166.2 (2)
C2—C1—C6—C5−3.4 (2)C12—C13—C14—O2−113.82 (15)
N1—C1—C6—Cl21.62 (19)O1—C14—O2—C15−1.5 (2)
C2—C1—C6—Cl2176.35 (11)C13—C14—O2—C15178.45 (13)
C1—N1—C7—C812.6 (2)C14—O2—C15—C17155.43 (15)
C1—N1—C7—C12−166.97 (14)C14—O2—C15—C16−82.92 (17)
C12—C7—C8—C92.1 (2)
D—H···AD—HH···AD···AD—H···A
N1—H1···O10.90 (2)2.05 (2)2.859 (2)149 (2)
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
N1—H1⋯O10.90 (2)2.05 (2)2.859 (2)149 (2)
  5 in total

Review 1.  Synthesis and anti-phlogistic potency of some new non-proteinogenic amino acid conjugates of "Diclofenac".

Authors:  M H Abo-Ghalia; A M Shalaby; W I el-Eraqi; H M Awad
Journal:  Amino Acids       Date:  1999       Impact factor: 3.520

2.  Synthesis and quantitative structure-activity relationships of diclofenac analogues.

Authors:  P Moser; A Sallmann; I Wiesenberg
Journal:  J Med Chem       Date:  1990-09       Impact factor: 7.446

3.  SHELXL: high-resolution refinement.

Authors:  G M Sheldrick; T R Schneider
Journal:  Methods Enzymol       Date:  1997       Impact factor: 1.600

Review 4.  Drug therapy reviews: antirheumatic agents.

Authors:  R P Evens
Journal:  Am J Hosp Pharm       Date:  1979-05

5.  A new anti-inflammatory derivative of imidazole which is less ulcerogenic than indomethacin in rats.

Authors:  T Corell; K M Jensen; J Splawinski
Journal:  Acta Pharmacol Toxicol (Copenh)       Date:  1979-09
  5 in total
  1 in total

1.  Methyl 2-[2-(2,6-dichloro-4-nitro-anilino)-3,5-dinitro-phen-yl]acetate.

Authors:  Muhammad Ilyas Tariq; Muhammad Jameel; M Nawaz Tahir; Toqir Ali; Muhammad Rizwan
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-03-05
  1 in total

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