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The geometric parameters of the title compound, C13H8Cl2N2O3, are in the usual ranges. The dihedral angle between the two aromatic rings is 78.33 (3)°. The crystal structure is stabilized by an N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705948X/im2046sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680705948X/im2046Isup2.hkl
Contains datablock I

CCDC reference: 674680

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.086
  • Data-to-parameter ratio = 20.2

checkCIF/PLATON results

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Alert level C PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent ..... ? PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 2.90 Ratio
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 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

Comment top

The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structural motif. Benzanilides serve as intermediates towards benzothiadiazin-4-ones (Makino et al., 2003), quinazoline-2,4-diones (Makino et al., 2001) and benzodiazepine-2,5-diones (Ho et al., 2002). 2,3-disubstituted 3H-quinazoline-4-ones act as 110δ kinase inhibitors (Zhichkin et al., 2007). Benzanilides have established their efficacy as central elements of ligands that bind to a wide variety of receptor types. Thus benzanilides containing aminoalkyl groups originally designed as peptidomimetics, have been incorporated in an Arg-Gly-Asp cyclic peptide yielding a high affinity GPIIb/IIIa ligand (Jackson et al., 1994). Imatinib, a 2-phenylaminopyrimidine derivative with an additional benzanilide substituent, is a drug used to treat certain kinds of cancer by inhibiting a number of tyrosine kinase enzymes (Capdeville et al., 2002). Pyridylmethyl containing benzanilides are vascular endothelial growth factor receptor and tyrosine kinase inhibitors (Manley et al., 2002). Furthermore, benzamides have been reported to exhibit activities as acetyl-CoA carboxylase and farnesyl transferase inhibitors (Igawa et al., 1999)

Geometric parameters of the title compound are in the usual ranges. The dihedral angle between the two aromatic rings is 78.33 (3)°. The nitro group is slightly bent out of the plane of the phenyl ring to which it is attached by 4.2 (3)°. The crystal structure is stabilized by an N—H···O hydrogen bond.

Related literature top

For related literature, see: Igawa et al. (1999); Jackson et al. (1994); Makino et al. (2001, 2003); Manley et al. (2002); Zhichkin et al. (2007); Capdeville et al. (2002); Ho et al. (2002).

Experimental top

A mixture of 2,4-dichloroaniline (10.0 g, 61.74 mmol), 2-nitrobenzoyl chloride (10 ml, 86.9 mmol), and pyridine (20 ml) was left at 25 °C for 15 h. Water (100 ml) was then added, and the resulting precipitates were collected. Recrystallization of the precipitates from benzene gave 15.74 g (82%) of title compound as yellow needles.

Refinement top

All H atoms were found in a difference map, but those bonded to C were geometrically positioned and refined with fixed individual displacement parameters [U(H) = 1.2 Ueq(C)] using a riding model with C—H = 0.95 Å. The amino H atom was freely refined.

Computing details top

Data collection: X-AREA (Stoe & Cie, 2001); cell refinement: X-AREA (Stoe & Cie, 2001); data reduction: X-AREA (Stoe & Cie, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top
[Figure 1] Fig. 1. Molecular structure of title compound with displacement ellipsoids at the 50% probability level.
N-(2,4-Dichlorophenyl)-2-nitrobenzamide top
Crystal data top
C13H8Cl2N2O3F(000) = 632
Mr = 311.11Dx = 1.538 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 23725 reflections
a = 11.4761 (8) Åθ = 3.6–29.7°
b = 8.8577 (3) ŵ = 0.49 mm1
c = 13.8105 (8) ÅT = 173 K
β = 106.893 (5)°Block, light brown
V = 1343.3 (1) Å30.33 × 0.30 × 0.25 mm
Z = 4
Data collection top
STOE IPDS II two-circle-
diffractometer
3758 independent reflections
Radiation source: fine-focus sealed tube3425 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.036
ω scansθmax = 29.6°, θmin = 3.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 1515
Tmin = 0.855, Tmax = 0.887k = 1211
23274 measured reflectionsl = 1919
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.086 w = 1/[σ2(Fo2) + (0.0412P)2 + 0.5969P]
where P = (Fo2 + 2Fc2)/3
S = 1.03(Δ/σ)max = 0.001
3758 reflectionsΔρmax = 0.40 e Å3
186 parametersΔρmin = 0.45 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0125 (15)
Crystal data top
C13H8Cl2N2O3V = 1343.3 (1) Å3
Mr = 311.11Z = 4
Monoclinic, P21/nMo Kα radiation
a = 11.4761 (8) ŵ = 0.49 mm1
b = 8.8577 (3) ÅT = 173 K
c = 13.8105 (8) Å0.33 × 0.30 × 0.25 mm
β = 106.893 (5)°
Data collection top
STOE IPDS II two-circle-
diffractometer
3758 independent reflections
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
3425 reflections with I > 2σ(I)
Tmin = 0.855, Tmax = 0.887Rint = 0.036
23274 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0340 restraints
wR(F2) = 0.086H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.40 e Å3
3758 reflectionsΔρmin = 0.45 e Å3
186 parameters
Special details top

Experimental. ;

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) top
xyzUiso*/Ueq
Cl10.49367 (3)0.69203 (4)0.65360 (2)0.03091 (9)
Cl20.25833 (4)0.60345 (5)0.26026 (2)0.04686 (12)
N10.30883 (10)0.48700 (12)0.69438 (7)0.0248 (2)
H10.3364 (17)0.565 (2)0.7309 (14)0.037 (4)*
N20.10801 (12)0.56153 (15)0.84036 (9)0.0367 (3)
O10.20242 (9)0.26735 (10)0.69472 (6)0.0296 (2)
O20.07693 (9)0.54611 (13)0.74857 (7)0.0374 (2)
O30.05376 (16)0.6415 (2)0.88434 (11)0.0858 (6)
C10.25772 (11)0.37847 (13)0.73830 (8)0.0225 (2)
C110.28609 (11)0.39697 (13)0.85223 (8)0.0221 (2)
C120.21713 (12)0.48132 (14)0.90077 (9)0.0264 (2)
C130.24700 (14)0.49206 (17)1.00569 (10)0.0339 (3)
H130.19850.55081.03670.041*
C140.34849 (14)0.41581 (17)1.06428 (9)0.0342 (3)
H140.37010.42241.13600.041*
C150.41841 (13)0.32998 (17)1.01840 (10)0.0337 (3)
H150.48750.27711.05880.040*
C160.38771 (12)0.32081 (15)0.91294 (9)0.0294 (3)
H160.43650.26210.88220.035*
C210.29876 (11)0.50223 (13)0.59010 (8)0.0233 (2)
C220.37878 (10)0.60066 (14)0.56190 (8)0.0233 (2)
C230.36844 (12)0.63043 (15)0.46057 (9)0.0289 (3)
H230.42270.69840.44250.035*
C240.27715 (12)0.55842 (16)0.38694 (9)0.0299 (3)
C250.19979 (13)0.45599 (17)0.41143 (9)0.0346 (3)
H250.13990.40490.35970.041*
C260.21057 (13)0.42819 (17)0.51313 (9)0.0334 (3)
H260.15730.35800.53040.040*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.02629 (15)0.03753 (17)0.02775 (15)0.00647 (11)0.00601 (11)0.00133 (11)
Cl20.0584 (2)0.0652 (3)0.01816 (15)0.01553 (19)0.01304 (14)0.00884 (14)
N10.0323 (5)0.0260 (5)0.0161 (4)0.0068 (4)0.0070 (4)0.0029 (4)
N20.0388 (6)0.0402 (6)0.0309 (6)0.0145 (5)0.0097 (5)0.0030 (5)
O10.0416 (5)0.0241 (4)0.0213 (4)0.0075 (4)0.0065 (3)0.0017 (3)
O20.0344 (5)0.0462 (6)0.0283 (5)0.0070 (4)0.0039 (4)0.0092 (4)
O30.0848 (11)0.1187 (14)0.0503 (8)0.0724 (11)0.0140 (7)0.0108 (8)
C10.0268 (5)0.0227 (5)0.0177 (5)0.0005 (4)0.0058 (4)0.0002 (4)
C110.0270 (5)0.0215 (5)0.0176 (5)0.0025 (4)0.0064 (4)0.0004 (4)
C120.0315 (6)0.0267 (5)0.0209 (5)0.0042 (4)0.0077 (4)0.0022 (4)
C130.0436 (7)0.0380 (7)0.0225 (6)0.0057 (6)0.0131 (5)0.0021 (5)
C140.0439 (7)0.0394 (7)0.0175 (5)0.0000 (6)0.0063 (5)0.0003 (5)
C150.0346 (6)0.0385 (7)0.0229 (6)0.0047 (5)0.0003 (5)0.0009 (5)
C160.0301 (6)0.0333 (6)0.0232 (5)0.0047 (5)0.0052 (4)0.0029 (5)
C210.0281 (5)0.0250 (5)0.0171 (5)0.0002 (4)0.0069 (4)0.0006 (4)
C220.0233 (5)0.0269 (5)0.0201 (5)0.0024 (4)0.0066 (4)0.0000 (4)
C230.0313 (6)0.0347 (6)0.0242 (5)0.0039 (5)0.0137 (5)0.0045 (5)
C240.0353 (6)0.0386 (7)0.0166 (5)0.0106 (5)0.0089 (4)0.0029 (4)
C250.0386 (7)0.0424 (7)0.0191 (5)0.0021 (6)0.0027 (5)0.0033 (5)
C260.0378 (7)0.0394 (7)0.0208 (5)0.0111 (6)0.0052 (5)0.0017 (5)
Geometric parameters (Å, º) top
Cl1—C221.7398 (12)C14—C151.385 (2)
Cl2—C241.7455 (12)C14—H140.9500
N1—C11.3576 (15)C15—C161.3977 (17)
N1—C211.4174 (14)C15—H150.9500
N1—H10.863 (19)C16—H160.9500
N2—O31.2155 (17)C21—C261.3996 (17)
N2—O21.2207 (15)C21—C221.4011 (16)
N2—C121.4703 (17)C22—C231.3947 (16)
O1—C11.2295 (14)C23—C241.3854 (19)
C1—C111.5201 (15)C23—H230.9500
C11—C121.3937 (16)C24—C251.378 (2)
C11—C161.3963 (17)C25—C261.3956 (17)
C12—C131.3919 (16)C25—H250.9500
C13—C141.385 (2)C26—H260.9500
C13—H130.9500
C1—N1—C21127.09 (10)C16—C15—H15119.9
C1—N1—H1116.2 (12)C11—C16—C15120.75 (12)
C21—N1—H1115.2 (12)C11—C16—H16119.6
O3—N2—O2123.13 (13)C15—C16—H16119.6
O3—N2—C12118.25 (12)C26—C21—C22117.91 (11)
O2—N2—C12118.61 (11)C26—C21—N1123.68 (11)
O1—C1—N1125.22 (10)C22—C21—N1118.37 (10)
O1—C1—C11121.18 (10)C23—C22—C21121.67 (11)
N1—C1—C11113.31 (10)C23—C22—Cl1117.90 (10)
C12—C11—C16117.52 (10)C21—C22—Cl1120.43 (9)
C12—C11—C1125.09 (10)C24—C23—C22118.37 (12)
C16—C11—C1117.37 (10)C24—C23—H23120.8
C13—C12—C11122.34 (11)C22—C23—H23120.8
C13—C12—N2117.98 (11)C25—C24—C23121.77 (11)
C11—C12—N2119.68 (10)C25—C24—Cl2119.70 (10)
C14—C13—C12119.05 (12)C23—C24—Cl2118.52 (10)
C14—C13—H13120.5C24—C25—C26119.21 (12)
C12—C13—H13120.5C24—C25—H25120.4
C15—C14—C13120.06 (12)C26—C25—H25120.4
C15—C14—H14120.0C25—C26—C21120.98 (12)
C13—C14—H14120.0C25—C26—H26119.5
C14—C15—C16120.29 (12)C21—C26—H26119.5
C14—C15—H15119.9
C21—N1—C1—O16.7 (2)C12—C11—C16—C150.16 (19)
C21—N1—C1—C11179.36 (11)C1—C11—C16—C15178.82 (12)
O1—C1—C11—C1296.77 (15)C14—C15—C16—C110.3 (2)
N1—C1—C11—C1289.02 (15)C1—N1—C21—C2616.0 (2)
O1—C1—C11—C1681.78 (15)C1—N1—C21—C22166.17 (12)
N1—C1—C11—C1692.43 (13)C26—C21—C22—C232.93 (19)
C16—C11—C12—C130.49 (19)N1—C21—C22—C23175.00 (11)
C1—C11—C12—C13179.04 (12)C26—C21—C22—Cl1178.00 (10)
C16—C11—C12—N2178.94 (12)N1—C21—C22—Cl14.08 (16)
C1—C11—C12—N20.40 (19)C21—C22—C23—C240.81 (18)
O3—N2—C12—C134.9 (2)Cl1—C22—C23—C24179.91 (10)
O2—N2—C12—C13175.91 (14)C22—C23—C24—C252.0 (2)
O3—N2—C12—C11175.68 (17)C22—C23—C24—Cl2176.39 (9)
O2—N2—C12—C113.6 (2)C23—C24—C25—C262.5 (2)
C11—C12—C13—C140.3 (2)Cl2—C24—C25—C26175.85 (11)
N2—C12—C13—C14179.13 (13)C24—C25—C26—C210.2 (2)
C12—C13—C14—C150.2 (2)C22—C21—C26—C252.4 (2)
C13—C14—C15—C160.5 (2)N1—C21—C26—C25175.42 (13)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.863 (19)2.172 (18)2.9401 (14)148.1 (16)
Symmetry code: (i) x+1/2, y+1/2, z+3/2.

Experimental details

Crystal data
Chemical formulaC13H8Cl2N2O3
Mr311.11
Crystal system, space groupMonoclinic, P21/n
Temperature (K)173
a, b, c (Å)11.4761 (8), 8.8577 (3), 13.8105 (8)
β (°) 106.893 (5)
V3)1343.3 (1)
Z4
Radiation typeMo Kα
µ (mm1)0.49
Crystal size (mm)0.33 × 0.30 × 0.25
Data collection
DiffractometerSTOE IPDS II two-circle-
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.855, 0.887
No. of measured, independent and
observed [I > 2σ(I)] reflections
23274, 3758, 3425
Rint0.036
(sin θ/λ)max1)0.695
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.086, 1.03
No. of reflections3758
No. of parameters186
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.40, 0.45

Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.863 (19)2.172 (18)2.9401 (14)148.1 (16)
Symmetry code: (i) x+1/2, y+1/2, z+3/2.
 

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