Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680705948X/im2046sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680705948X/im2046Isup2.hkl |
CCDC reference: 674680
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.
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.
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).
Fig. 1. Molecular structure of title compound with displacement ellipsoids at the 50% probability level. |
C13H8Cl2N2O3 | F(000) = 632 |
Mr = 311.11 | Dx = 1.538 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 23725 reflections |
a = 11.4761 (8) Å | θ = 3.6–29.7° |
b = 8.8577 (3) Å | µ = 0.49 mm−1 |
c = 13.8105 (8) Å | T = 173 K |
β = 106.893 (5)° | Block, light brown |
V = 1343.3 (1) Å3 | 0.33 × 0.30 × 0.25 mm |
Z = 4 |
STOE IPDS II two-circle- diffractometer | 3758 independent reflections |
Radiation source: fine-focus sealed tube | 3425 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.036 |
ω scans | θmax = 29.6°, θmin = 3.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −15→15 |
Tmin = 0.855, Tmax = 0.887 | k = −12→11 |
23274 measured reflections | l = −19→19 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.034 | H 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 reflections | Δρmax = 0.40 e Å−3 |
186 parameters | Δρmin = −0.45 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0125 (15) |
C13H8Cl2N2O3 | V = 1343.3 (1) Å3 |
Mr = 311.11 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.4761 (8) Å | µ = 0.49 mm−1 |
b = 8.8577 (3) Å | T = 173 K |
c = 13.8105 (8) Å | 0.33 × 0.30 × 0.25 mm |
β = 106.893 (5)° |
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 = 0.887 | Rint = 0.036 |
23274 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.086 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.40 e Å−3 |
3758 reflections | Δρmin = −0.45 e Å−3 |
186 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | 0.49367 (3) | 0.69203 (4) | 0.65360 (2) | 0.03091 (9) | |
Cl2 | 0.25833 (4) | 0.60345 (5) | 0.26026 (2) | 0.04686 (12) | |
N1 | 0.30883 (10) | 0.48700 (12) | 0.69438 (7) | 0.0248 (2) | |
H1 | 0.3364 (17) | 0.565 (2) | 0.7309 (14) | 0.037 (4)* | |
N2 | 0.10801 (12) | 0.56153 (15) | 0.84036 (9) | 0.0367 (3) | |
O1 | 0.20242 (9) | 0.26735 (10) | 0.69472 (6) | 0.0296 (2) | |
O2 | 0.07693 (9) | 0.54611 (13) | 0.74857 (7) | 0.0374 (2) | |
O3 | 0.05376 (16) | 0.6415 (2) | 0.88434 (11) | 0.0858 (6) | |
C1 | 0.25772 (11) | 0.37847 (13) | 0.73830 (8) | 0.0225 (2) | |
C11 | 0.28609 (11) | 0.39697 (13) | 0.85223 (8) | 0.0221 (2) | |
C12 | 0.21713 (12) | 0.48132 (14) | 0.90077 (9) | 0.0264 (2) | |
C13 | 0.24700 (14) | 0.49206 (17) | 1.00569 (10) | 0.0339 (3) | |
H13 | 0.1985 | 0.5508 | 1.0367 | 0.041* | |
C14 | 0.34849 (14) | 0.41581 (17) | 1.06428 (9) | 0.0342 (3) | |
H14 | 0.3701 | 0.4224 | 1.1360 | 0.041* | |
C15 | 0.41841 (13) | 0.32998 (17) | 1.01840 (10) | 0.0337 (3) | |
H15 | 0.4875 | 0.2771 | 1.0588 | 0.040* | |
C16 | 0.38771 (12) | 0.32081 (15) | 0.91294 (9) | 0.0294 (3) | |
H16 | 0.4365 | 0.2621 | 0.8822 | 0.035* | |
C21 | 0.29876 (11) | 0.50223 (13) | 0.59010 (8) | 0.0233 (2) | |
C22 | 0.37878 (10) | 0.60066 (14) | 0.56190 (8) | 0.0233 (2) | |
C23 | 0.36844 (12) | 0.63043 (15) | 0.46057 (9) | 0.0289 (3) | |
H23 | 0.4227 | 0.6984 | 0.4425 | 0.035* | |
C24 | 0.27715 (12) | 0.55842 (16) | 0.38694 (9) | 0.0299 (3) | |
C25 | 0.19979 (13) | 0.45599 (17) | 0.41143 (9) | 0.0346 (3) | |
H25 | 0.1399 | 0.4049 | 0.3597 | 0.041* | |
C26 | 0.21057 (13) | 0.42819 (17) | 0.51313 (9) | 0.0334 (3) | |
H26 | 0.1573 | 0.3580 | 0.5304 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.02629 (15) | 0.03753 (17) | 0.02775 (15) | −0.00647 (11) | 0.00601 (11) | −0.00133 (11) |
Cl2 | 0.0584 (2) | 0.0652 (3) | 0.01816 (15) | 0.01553 (19) | 0.01304 (14) | 0.00884 (14) |
N1 | 0.0323 (5) | 0.0260 (5) | 0.0161 (4) | −0.0068 (4) | 0.0070 (4) | −0.0029 (4) |
N2 | 0.0388 (6) | 0.0402 (6) | 0.0309 (6) | 0.0145 (5) | 0.0097 (5) | 0.0030 (5) |
O1 | 0.0416 (5) | 0.0241 (4) | 0.0213 (4) | −0.0075 (4) | 0.0065 (3) | −0.0017 (3) |
O2 | 0.0344 (5) | 0.0462 (6) | 0.0283 (5) | 0.0070 (4) | 0.0039 (4) | 0.0092 (4) |
O3 | 0.0848 (11) | 0.1187 (14) | 0.0503 (8) | 0.0724 (11) | 0.0140 (7) | −0.0108 (8) |
C1 | 0.0268 (5) | 0.0227 (5) | 0.0177 (5) | 0.0005 (4) | 0.0058 (4) | 0.0002 (4) |
C11 | 0.0270 (5) | 0.0215 (5) | 0.0176 (5) | −0.0025 (4) | 0.0064 (4) | −0.0004 (4) |
C12 | 0.0315 (6) | 0.0267 (5) | 0.0209 (5) | 0.0042 (4) | 0.0077 (4) | 0.0022 (4) |
C13 | 0.0436 (7) | 0.0380 (7) | 0.0225 (6) | 0.0057 (6) | 0.0131 (5) | −0.0021 (5) |
C14 | 0.0439 (7) | 0.0394 (7) | 0.0175 (5) | 0.0000 (6) | 0.0063 (5) | −0.0003 (5) |
C15 | 0.0346 (6) | 0.0385 (7) | 0.0229 (6) | 0.0047 (5) | 0.0003 (5) | 0.0009 (5) |
C16 | 0.0301 (6) | 0.0333 (6) | 0.0232 (5) | 0.0047 (5) | 0.0052 (4) | −0.0029 (5) |
C21 | 0.0281 (5) | 0.0250 (5) | 0.0171 (5) | −0.0002 (4) | 0.0069 (4) | −0.0006 (4) |
C22 | 0.0233 (5) | 0.0269 (5) | 0.0201 (5) | 0.0024 (4) | 0.0066 (4) | 0.0000 (4) |
C23 | 0.0313 (6) | 0.0347 (6) | 0.0242 (5) | 0.0039 (5) | 0.0137 (5) | 0.0045 (5) |
C24 | 0.0353 (6) | 0.0386 (7) | 0.0166 (5) | 0.0106 (5) | 0.0089 (4) | 0.0029 (4) |
C25 | 0.0386 (7) | 0.0424 (7) | 0.0191 (5) | −0.0021 (6) | 0.0027 (5) | −0.0033 (5) |
C26 | 0.0378 (7) | 0.0394 (7) | 0.0208 (5) | −0.0111 (6) | 0.0052 (5) | −0.0017 (5) |
Cl1—C22 | 1.7398 (12) | C14—C15 | 1.385 (2) |
Cl2—C24 | 1.7455 (12) | C14—H14 | 0.9500 |
N1—C1 | 1.3576 (15) | C15—C16 | 1.3977 (17) |
N1—C21 | 1.4174 (14) | C15—H15 | 0.9500 |
N1—H1 | 0.863 (19) | C16—H16 | 0.9500 |
N2—O3 | 1.2155 (17) | C21—C26 | 1.3996 (17) |
N2—O2 | 1.2207 (15) | C21—C22 | 1.4011 (16) |
N2—C12 | 1.4703 (17) | C22—C23 | 1.3947 (16) |
O1—C1 | 1.2295 (14) | C23—C24 | 1.3854 (19) |
C1—C11 | 1.5201 (15) | C23—H23 | 0.9500 |
C11—C12 | 1.3937 (16) | C24—C25 | 1.378 (2) |
C11—C16 | 1.3963 (17) | C25—C26 | 1.3956 (17) |
C12—C13 | 1.3919 (16) | C25—H25 | 0.9500 |
C13—C14 | 1.385 (2) | C26—H26 | 0.9500 |
C13—H13 | 0.9500 | ||
C1—N1—C21 | 127.09 (10) | C16—C15—H15 | 119.9 |
C1—N1—H1 | 116.2 (12) | C11—C16—C15 | 120.75 (12) |
C21—N1—H1 | 115.2 (12) | C11—C16—H16 | 119.6 |
O3—N2—O2 | 123.13 (13) | C15—C16—H16 | 119.6 |
O3—N2—C12 | 118.25 (12) | C26—C21—C22 | 117.91 (11) |
O2—N2—C12 | 118.61 (11) | C26—C21—N1 | 123.68 (11) |
O1—C1—N1 | 125.22 (10) | C22—C21—N1 | 118.37 (10) |
O1—C1—C11 | 121.18 (10) | C23—C22—C21 | 121.67 (11) |
N1—C1—C11 | 113.31 (10) | C23—C22—Cl1 | 117.90 (10) |
C12—C11—C16 | 117.52 (10) | C21—C22—Cl1 | 120.43 (9) |
C12—C11—C1 | 125.09 (10) | C24—C23—C22 | 118.37 (12) |
C16—C11—C1 | 117.37 (10) | C24—C23—H23 | 120.8 |
C13—C12—C11 | 122.34 (11) | C22—C23—H23 | 120.8 |
C13—C12—N2 | 117.98 (11) | C25—C24—C23 | 121.77 (11) |
C11—C12—N2 | 119.68 (10) | C25—C24—Cl2 | 119.70 (10) |
C14—C13—C12 | 119.05 (12) | C23—C24—Cl2 | 118.52 (10) |
C14—C13—H13 | 120.5 | C24—C25—C26 | 119.21 (12) |
C12—C13—H13 | 120.5 | C24—C25—H25 | 120.4 |
C15—C14—C13 | 120.06 (12) | C26—C25—H25 | 120.4 |
C15—C14—H14 | 120.0 | C25—C26—C21 | 120.98 (12) |
C13—C14—H14 | 120.0 | C25—C26—H26 | 119.5 |
C14—C15—C16 | 120.29 (12) | C21—C26—H26 | 119.5 |
C14—C15—H15 | 119.9 | ||
C21—N1—C1—O1 | 6.7 (2) | C12—C11—C16—C15 | −0.16 (19) |
C21—N1—C1—C11 | −179.36 (11) | C1—C11—C16—C15 | −178.82 (12) |
O1—C1—C11—C12 | −96.77 (15) | C14—C15—C16—C11 | −0.3 (2) |
N1—C1—C11—C12 | 89.02 (15) | C1—N1—C21—C26 | 16.0 (2) |
O1—C1—C11—C16 | 81.78 (15) | C1—N1—C21—C22 | −166.17 (12) |
N1—C1—C11—C16 | −92.43 (13) | C26—C21—C22—C23 | 2.93 (19) |
C16—C11—C12—C13 | 0.49 (19) | N1—C21—C22—C23 | −175.00 (11) |
C1—C11—C12—C13 | 179.04 (12) | C26—C21—C22—Cl1 | −178.00 (10) |
C16—C11—C12—N2 | −178.94 (12) | N1—C21—C22—Cl1 | 4.08 (16) |
C1—C11—C12—N2 | −0.40 (19) | C21—C22—C23—C24 | −0.81 (18) |
O3—N2—C12—C13 | 4.9 (2) | Cl1—C22—C23—C24 | −179.91 (10) |
O2—N2—C12—C13 | −175.91 (14) | C22—C23—C24—C25 | −2.0 (2) |
O3—N2—C12—C11 | −175.68 (17) | C22—C23—C24—Cl2 | 176.39 (9) |
O2—N2—C12—C11 | 3.6 (2) | C23—C24—C25—C26 | 2.5 (2) |
C11—C12—C13—C14 | −0.3 (2) | Cl2—C24—C25—C26 | −175.85 (11) |
N2—C12—C13—C14 | 179.13 (13) | C24—C25—C26—C21 | −0.2 (2) |
C12—C13—C14—C15 | −0.2 (2) | C22—C21—C26—C25 | −2.4 (2) |
C13—C14—C15—C16 | 0.5 (2) | N1—C21—C26—C25 | 175.42 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.863 (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 formula | C13H8Cl2N2O3 |
Mr | 311.11 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 11.4761 (8), 8.8577 (3), 13.8105 (8) |
β (°) | 106.893 (5) |
V (Å3) | 1343.3 (1) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.49 |
Crystal size (mm) | 0.33 × 0.30 × 0.25 |
Data collection | |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.855, 0.887 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 23274, 3758, 3425 |
Rint | 0.036 |
(sin θ/λ)max (Å−1) | 0.695 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.086, 1.03 |
No. of reflections | 3758 |
No. of parameters | 186 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.40, −0.45 |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.863 (19) | 2.172 (18) | 2.9401 (14) | 148.1 (16) |
Symmetry code: (i) −x+1/2, y+1/2, −z+3/2. |
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.