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Acta Crystallogr Sect E Struct Rep Online. 2008 August 1; 64(Pt 8): o1625.
Published online 2008 July 31. doi:  10.1107/S1600536808023234
PMCID: PMC2962079

N-(4-Chloro­phen­yl)-3,4,5-trimethoxy­benzamide

Abstract

In the title compound, C16H16ClNO4, the dihedral angle between the two aromatic rings is 67.33 (8)°. The crystal packing shows strong inter­molecular N—H(...)O hydrogen bonds that link the mol­ecules to form chains along [An external file that holds a picture, illustration, etc.
Object name is e-64-o1625-efi1.jpg01].

Related literature

For related literature, see: Capdeville et al. (2002 [triangle]); Ho et al. (2002 [triangle]); Igawa et al. (1999 [triangle]); Jackson et al. (1994 [triangle]); Makino et al. (2003 [triangle]); Zhichkin et al. (2007 [triangle]).

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Object name is e-64-o1625-scheme1.jpg

Experimental

Crystal data

  • C16H16ClNO4
  • M r = 321.75
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-64-o1625-efi2.jpg
  • a = 9.487 (2) Å
  • b = 25.666 (6) Å
  • c = 6.9781 (15) Å
  • β = 112.340 (5)°
  • V = 1571.5 (6) Å3
  • Z = 4
  • Mo Kα radiation
  • μ = 0.26 mm−1
  • T = 120 (2) K
  • 0.41 × 0.10 × 0.10 mm

Data collection

  • Bruker SMART APEX diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 2004 [triangle]) T min = 0.901, T max = 0.975
  • 6765 measured reflections
  • 3581 independent reflections
  • 3104 reflections with I > 2σ(I)
  • R int = 0.040

Refinement

  • R[F 2 > 2σ(F 2)] = 0.045
  • wR(F 2) = 0.106
  • S = 1.02
  • 3581 reflections
  • 202 parameters
  • 2 restraints
  • H-atom parameters constrained
  • Δρmax = 0.33 e Å−3
  • Δρmin = −0.24 e Å−3
  • Absolute structure: Flack (1983 [triangle]), with 1780 Friedel pairs
  • Flack parameter: 0.06 (6)

Data collection: SMART (Bruker, 2002 [triangle]); cell refinement: SAINT (Bruker, 2002 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 [triangle]); molecular graphics: SHELXTL (Sheldrick, 2008 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536808023234/bt2747sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808023234/bt2747Isup2.hkl

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

Acknowledgments

AS gratefully acknowledges a research grant from Quaid-I-Azam University, Islamabad.

supplementary crystallographic information

Comment

The benzanilide core is present in compounds with a wide range of biological activities that it has been called a privileged structure. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), benzodiazepine-2,5-diones (Ho et al., 20022), and 2,3-disubstituted 3H-quinazoline-4-ones (Zhichkin et al., 2007). Benzanilides have established their efficacy as centroid elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as a peptidomimetic, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib is an ATP-site binding kinase inhibitor and platelet-derived growth factor receptor kinases (Capdeville et al., 2002). Benzamides have activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound, C16H16ClNO4, are in the usual ranges. The dihedral angle between the two aromatic rings is 67.33 (8)° and the torsion angles N1—C1—C2—C3 and C1—N1—C11—C12 are -31.1 (3)° and -39.2 (4)°, respectively. Of the three methoxy groups two of them lie nearly in plane with the aromatic ring, the O(3) group is almost perpendicular with C9—O3—C5—C4 of 92.2 (3)°. The crystal packing shows strong intermolecular N—H···O bonds that link molecules to endless chains along [-101]. Details are given in Table 1.

Experimental

Trimethoxybenzoyl chloride (5.4 mmol) in CHCl3 was treated with 4-chloroaniline (21.6 mmol) under a nitrogen atmosphere at reflux for 4 h. Upon cooling, the reaction mixture was diluted with CHCl3 and washed consecutively with aq 1 M HCl and saturated aq NaHCO3. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. Crystallization of the residue in CHCl3 afforded the title compound (84%) as white needles: IR (KBr) 3226, 1665, 1616, 1520, 1352 cm-1; 1H NMR (CDCl3, 400 MHz) δ 8.13 (d, J = 8 Hz, 1H), 7.81 (d, J = 8 Hz, 1H), 7.51 (dd, J = 8 Hz, 1H), 7.66 (dd, J = 8 Hz, 1H), 7.43 (d, J = 8 Hz, 2H), 7.36 (br s, 1H), 7.25 (d, J = 8 Hz, 1H), 3.89 (9H, s, OMex3). Anal. Calcd. For C16H16ClNO4, C, 59.73; H, 5.01; 11.02; N, 4.35; found C, 59.69; H, 5.04; 11.02; N, 4.42

Refinement

Hydrogen atoms were located in difference syntheses, refined at idealized positions riding on the carbon or nitrogen atoms with isotropic displacement parameters Uiso(H) = 1.2Ueq(C or N) and 1.5U for methyl-C.

Figures

Fig. 1.
Molecular structure of title compound. Displacement ellipsoids are drawn at the 50% probability level.
Fig. 2.
Crystal packing viewed along [001] with intermolecular hydrogen bonding pattern indicated as dashed lines. H-atoms not involved in hydrogen bonding are omitted.

Crystal data

C16H16ClNO4F000 = 672
Mr = 321.75Dx = 1.360 Mg m3
Monoclinic, CcMo Kα radiation λ = 0.71073 Å
Hall symbol: C -2ycCell parameters from 879 reflections
a = 9.487 (2) Åθ = 2.5–26.6º
b = 25.666 (6) ŵ = 0.26 mm1
c = 6.9781 (15) ÅT = 120 (2) K
β = 112.340 (5)ºPrism, colourless
V = 1571.5 (6) Å30.41 × 0.10 × 0.10 mm
Z = 4

Data collection

Bruker SMART APEX diffractometer3581 independent reflections
Radiation source: sealed tube3104 reflections with I > 2σ(I)
Monochromator: graphiteRint = 0.040
T = 120(2) Kθmax = 27.9º
[var phi] and ω scansθmin = 1.6º
Absorption correction: multi-scan(SADABS; Sheldrick, 2004)h = −12→12
Tmin = 0.901, Tmax = 0.975k = −33→29
6765 measured reflectionsl = −9→9

Refinement

Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.045  w = 1/[σ2(Fo2) + (0.0463P)2 + 0.1374P] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.106(Δ/σ)max < 0.001
S = 1.02Δρmax = 0.33 e Å3
3581 reflectionsΔρmin = −0.24 e Å3
202 parametersExtinction correction: none
2 restraintsAbsolute structure: Flack (1983), with 1780 Friedel pairs
Primary atom site location: structure-invariant direct methodsFlack parameter: 0.06 (6)
Secondary atom site location: difference Fourier map

Special details

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2)

xyzUiso*/Ueq
Cl10.24506 (8)0.52096 (2)−0.45259 (9)0.03098 (17)
O10.0700 (2)0.75731 (7)−0.2052 (3)0.0251 (4)
O20.3495 (2)0.83040 (7)0.6718 (3)0.0293 (4)
O30.2739 (2)0.92522 (7)0.5093 (3)0.0287 (4)
O40.1760 (2)0.94204 (7)0.1029 (3)0.0293 (4)
N10.2656 (2)0.71265 (7)0.0305 (3)0.0206 (4)
H10.33660.71360.15620.025*
C10.1742 (3)0.75494 (10)−0.0350 (4)0.0201 (5)
C20.2087 (3)0.79915 (9)0.1153 (4)0.0190 (5)
C30.2689 (3)0.79115 (10)0.3293 (4)0.0207 (5)
H3A0.29260.75700.38460.025*
C40.2938 (3)0.83381 (10)0.4601 (4)0.0217 (5)
C50.2589 (3)0.88383 (10)0.3797 (4)0.0217 (5)
C60.2015 (3)0.89163 (10)0.1650 (4)0.0226 (6)
C70.1739 (3)0.84890 (9)0.0330 (4)0.0209 (5)
H7A0.13140.8538−0.11290.025*
C80.4275 (4)0.78426 (12)0.7598 (5)0.0380 (7)
H8A0.35600.75490.72230.057*
H8B0.47270.78780.91090.057*
H8C0.50830.77790.70730.057*
C90.4195 (4)0.94971 (13)0.5730 (6)0.0457 (8)
H9A0.49860.92510.65410.069*
H9B0.42130.98030.65820.069*
H9C0.43870.96060.45060.069*
C100.1094 (4)0.95144 (11)−0.1151 (5)0.0375 (7)
H10A0.17640.9377−0.18070.056*
H10B0.09600.9890−0.14050.056*
H10C0.01000.9341−0.17360.056*
C110.2554 (3)0.66682 (9)−0.0888 (4)0.0194 (5)
C120.1169 (3)0.64558 (10)−0.2157 (4)0.0238 (5)
H12A0.02440.6618−0.22580.029*
C130.1133 (3)0.60093 (10)−0.3273 (4)0.0269 (6)
H13A0.01840.5868−0.41580.032*
C140.2479 (3)0.57674 (10)−0.3103 (4)0.0218 (5)
C150.3862 (3)0.59685 (10)−0.1809 (4)0.0259 (6)
H15A0.47840.5798−0.16750.031*
C160.3897 (3)0.64200 (10)−0.0706 (4)0.0250 (6)
H16A0.48470.65610.01820.030*

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
Cl10.0333 (3)0.0268 (3)0.0286 (3)0.0033 (3)0.0071 (3)−0.0101 (3)
O10.0181 (9)0.0240 (10)0.0225 (9)0.0011 (7)−0.0043 (7)−0.0031 (7)
O20.0373 (11)0.0277 (10)0.0193 (9)0.0051 (8)0.0066 (8)0.0008 (8)
O30.0346 (11)0.0236 (9)0.0262 (10)−0.0009 (8)0.0097 (8)−0.0075 (8)
O40.0406 (12)0.0171 (9)0.0248 (10)0.0013 (8)0.0062 (9)0.0014 (8)
N10.0170 (10)0.0186 (10)0.0186 (10)0.0016 (8)−0.0019 (8)−0.0021 (9)
C10.0157 (11)0.0203 (12)0.0207 (13)−0.0004 (9)0.0026 (11)−0.0003 (10)
C20.0154 (12)0.0179 (12)0.0214 (13)−0.0006 (9)0.0046 (10)−0.0017 (10)
C30.0172 (11)0.0188 (12)0.0221 (13)−0.0002 (9)0.0027 (10)0.0033 (10)
C40.0218 (13)0.0241 (14)0.0184 (13)−0.0003 (10)0.0068 (11)−0.0015 (10)
C50.0218 (12)0.0203 (13)0.0230 (13)−0.0009 (10)0.0085 (11)−0.0056 (10)
C60.0227 (13)0.0181 (13)0.0248 (14)0.0016 (10)0.0065 (11)0.0010 (10)
C70.0192 (11)0.0211 (13)0.0187 (12)0.0010 (9)0.0029 (10)0.0005 (10)
C80.052 (2)0.0397 (17)0.0211 (14)0.0166 (15)0.0126 (14)0.0076 (13)
C90.0401 (18)0.0386 (18)0.050 (2)−0.0104 (14)0.0079 (16)−0.0163 (15)
C100.058 (2)0.0190 (14)0.0282 (15)0.0046 (13)0.0084 (14)0.0044 (12)
C110.0225 (12)0.0159 (12)0.0161 (11)−0.0007 (9)0.0031 (10)0.0018 (9)
C120.0176 (12)0.0218 (13)0.0294 (14)0.0030 (10)0.0059 (11)−0.0023 (11)
C130.0200 (13)0.0283 (15)0.0255 (14)−0.0029 (10)0.0011 (11)−0.0080 (11)
C140.0286 (13)0.0161 (12)0.0209 (13)0.0003 (10)0.0095 (11)−0.0039 (10)
C150.0208 (13)0.0263 (14)0.0285 (14)0.0057 (10)0.0069 (11)0.0015 (11)
C160.0191 (13)0.0233 (14)0.0255 (14)−0.0013 (10)0.0005 (11)−0.0014 (11)

Geometric parameters (Å, °)

Cl1—C141.737 (2)C8—H8A0.9800
O1—C11.225 (3)C8—H8B0.9800
O2—C41.369 (3)C8—H8C0.9800
O2—C81.408 (3)C9—H9A0.9800
O3—C51.367 (3)C9—H9B0.9800
O3—C91.426 (4)C9—H9C0.9800
O4—C61.357 (3)C10—H10A0.9800
O4—C101.429 (4)C10—H10B0.9800
N1—C11.356 (3)C10—H10C0.9800
N1—C111.423 (3)C11—C161.386 (4)
N1—H10.8800C11—C121.386 (4)
C1—C21.494 (3)C12—C131.378 (4)
C2—C71.387 (3)C12—H12A0.9500
C2—C31.397 (4)C13—C141.384 (4)
C3—C41.387 (3)C13—H13A0.9500
C3—H3A0.9500C14—C151.380 (4)
C4—C51.390 (4)C15—C161.385 (4)
C5—C61.400 (3)C15—H15A0.9500
C6—C71.392 (4)C16—H16A0.9500
C7—H7A0.9500
C4—O2—C8116.6 (2)H8B—C8—H8C109.5
C5—O3—C9113.2 (2)O3—C9—H9A109.5
C6—O4—C10117.0 (2)O3—C9—H9B109.5
C1—N1—C11124.9 (2)H9A—C9—H9B109.5
C1—N1—H1117.5O3—C9—H9C109.5
C11—N1—H1117.5H9A—C9—H9C109.5
O1—C1—N1123.0 (2)H9B—C9—H9C109.5
O1—C1—C2121.6 (2)O4—C10—H10A109.5
N1—C1—C2115.5 (2)O4—C10—H10B109.5
C7—C2—C3120.9 (2)H10A—C10—H10B109.5
C7—C2—C1117.0 (2)O4—C10—H10C109.5
C3—C2—C1122.0 (2)H10A—C10—H10C109.5
C4—C3—C2119.1 (2)H10B—C10—H10C109.5
C4—C3—H3A120.5C16—C11—C12119.5 (2)
C2—C3—H3A120.5C16—C11—N1118.1 (2)
O2—C4—C3124.0 (2)C12—C11—N1122.4 (2)
O2—C4—C5115.4 (2)C13—C12—C11120.1 (2)
C3—C4—C5120.6 (2)C13—C12—H12A119.9
O3—C5—C4120.1 (2)C11—C12—H12A119.9
O3—C5—C6119.8 (2)C12—C13—C14120.0 (2)
C4—C5—C6120.0 (2)C12—C13—H13A120.0
O4—C6—C7125.0 (2)C14—C13—H13A120.0
O4—C6—C5115.3 (2)C15—C14—C13120.3 (2)
C7—C6—C5119.6 (2)C15—C14—Cl1119.1 (2)
C2—C7—C6119.7 (2)C13—C14—Cl1120.5 (2)
C2—C7—H7A120.1C14—C15—C16119.5 (2)
C6—C7—H7A120.1C14—C15—H15A120.2
O2—C8—H8A109.5C16—C15—H15A120.2
O2—C8—H8B109.5C15—C16—C11120.5 (2)
H8A—C8—H8B109.5C15—C16—H16A119.8
O2—C8—H8C109.5C11—C16—H16A119.8
H8A—C8—H8C109.5
C11—N1—C1—O11.5 (4)O3—C5—C6—O45.1 (3)
C11—N1—C1—C2−178.5 (2)C4—C5—C6—O4−177.9 (2)
O1—C1—C2—C7−29.2 (3)O3—C5—C6—C7−174.4 (2)
N1—C1—C2—C7150.8 (2)C4—C5—C6—C72.6 (4)
O1—C1—C2—C3148.9 (2)C3—C2—C7—C61.1 (4)
N1—C1—C2—C3−31.1 (3)C1—C2—C7—C6179.2 (2)
C7—C2—C3—C40.0 (4)O4—C6—C7—C2178.2 (2)
C1—C2—C3—C4−178.0 (2)C5—C6—C7—C2−2.4 (4)
C8—O2—C4—C319.9 (4)C1—N1—C11—C16143.0 (3)
C8—O2—C4—C5−161.6 (3)C1—N1—C11—C12−39.2 (4)
C2—C3—C4—O2178.7 (2)C16—C11—C12—C13−1.8 (4)
C2—C3—C4—C50.2 (4)N1—C11—C12—C13−179.6 (2)
C9—O3—C5—C492.2 (3)C11—C12—C13—C141.0 (4)
C9—O3—C5—C6−90.8 (3)C12—C13—C14—C150.5 (4)
O2—C4—C5—O3−3.1 (3)C12—C13—C14—Cl1−179.1 (2)
C3—C4—C5—O3175.5 (2)C13—C14—C15—C16−1.1 (4)
O2—C4—C5—C6179.8 (2)Cl1—C14—C15—C16178.5 (2)
C3—C4—C5—C6−1.6 (4)C14—C15—C16—C110.3 (4)
C10—O4—C6—C72.9 (4)C12—C11—C16—C151.2 (4)
C10—O4—C6—C5−176.6 (3)N1—C11—C16—C15179.1 (2)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.882.182.878 (3)136

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BT2747).

References

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  • Igawa, H., Nishimura, M., Okada, K. & Nakamura, T. (1999). Jpn. Patent Kokai Tokkyo Koho JP 11171848.
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  • Zhichkin, P., Kesicki, E., Treiberg, J., Bourdon, L., Ronsheim, M., Ooi, H. C., White, S., Judkins, A. & Fairfax, D. (2007). Org. Lett.9, 1415–1418. [PubMed]

Articles from Acta Crystallographica Section E: Structure Reports Online are provided here courtesy of International Union of Crystallography