Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055742/hb2615sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055742/hb2615Isup2.hkl |
CCDC reference: 674080
A mixture of 4-chloroaniline (10.0 g, 65.7 mmol), 2-nitrobenzoyl chloride (10 ml, 86.9 mmol) and pyridine (20 ml) was left at 298 K for 15 h. Water (100 ml) was then added, and the resulting precipitate was collected. Recrystallization from benzene gave 12.6 g (75%) of (I) as yellow needles: mp 368–369 K, 1H NMR (CDCl3) δ 7.23–8.30 (m, 8H, Ar—Hs), 11.36 (br s, 1H, NH).
All H atoms were located in a difference map. Those bonded to C were relocated in idealized positions (C—H = 0.95 Å) and refined as riding with Uiso(H) = 1.2 Ueq(C). The H atom bonded to N 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, 1997); 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. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms at the 50% probability level. |
C13H9ClN2O3 | F(000) = 2272 |
Mr = 276.67 | Dx = 1.483 Mg m−3 |
Orthorhombic, Fdd2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: F 2 -2d | Cell parameters from 9190 reflections |
a = 23.8527 (15) Å | θ = 2.8–25.2° |
b = 40.936 (3) Å | µ = 0.31 mm−1 |
c = 5.0780 (4) Å | T = 173 K |
V = 4958.3 (6) Å3 | Needle, colourless |
Z = 16 | 0.33 × 0.12 × 0.11 mm |
STOE IPDS II two-circle- diffractometer | 2181 independent reflections |
Radiation source: fine-focus sealed tube | 2083 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.071 |
ω scans | θmax = 25.0°, θmin = 2.6° |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | h = −26→28 |
Tmin = 0.904, Tmax = 0.956 | k = −40→48 |
10236 measured reflections | l = −6→6 |
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) = 0.090 | w = 1/[σ2(Fo2) + (0.0698P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2181 reflections | Δρmax = 0.16 e Å−3 |
176 parameters | Δρmin = −0.23 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 955 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.00 (6) |
C13H9ClN2O3 | V = 4958.3 (6) Å3 |
Mr = 276.67 | Z = 16 |
Orthorhombic, Fdd2 | Mo Kα radiation |
a = 23.8527 (15) Å | µ = 0.31 mm−1 |
b = 40.936 (3) Å | T = 173 K |
c = 5.0780 (4) Å | 0.33 × 0.12 × 0.11 mm |
STOE IPDS II two-circle- diffractometer | 2181 independent reflections |
Absorption correction: multi-scan (MULABS; Spek, 2003; Blessing, 1995) | 2083 reflections with I > 2σ(I) |
Tmin = 0.904, Tmax = 0.956 | Rint = 0.071 |
10236 measured reflections |
R[F2 > 2σ(F2)] = 0.034 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.090 | Δρmax = 0.16 e Å−3 |
S = 1.04 | Δρmin = −0.23 e Å−3 |
2181 reflections | Absolute structure: Flack (1983), 955 Friedel pairs |
176 parameters | Absolute structure parameter: 0.00 (6) |
1 restraint |
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 | 0.67478 (2) | 0.239794 (13) | 0.39083 (13) | 0.03892 (17) | |
C1 | 0.41096 (8) | 0.18013 (4) | 0.1564 (4) | 0.0221 (4) | |
O1 | 0.42715 (6) | 0.18287 (4) | −0.0713 (3) | 0.0355 (4) | |
N1 | 0.44331 (7) | 0.18661 (4) | 0.3687 (3) | 0.0215 (3) | |
H1 | 0.4295 (10) | 0.1826 (6) | 0.526 (6) | 0.026 (6)* | |
N2 | 0.35978 (7) | 0.12292 (4) | −0.0872 (4) | 0.0269 (4) | |
O2 | 0.40437 (7) | 0.11395 (4) | 0.0044 (4) | 0.0413 (4) | |
O3 | 0.34094 (7) | 0.11341 (5) | −0.2990 (4) | 0.0481 (5) | |
C11 | 0.35158 (8) | 0.17038 (5) | 0.2139 (3) | 0.0222 (4) | |
C12 | 0.32552 (8) | 0.14551 (5) | 0.0699 (4) | 0.0220 (4) | |
C13 | 0.26869 (9) | 0.13956 (5) | 0.0811 (4) | 0.0296 (5) | |
H13 | 0.2520 | 0.1232 | −0.0258 | 0.036* | |
C14 | 0.23644 (9) | 0.15811 (6) | 0.2528 (5) | 0.0360 (5) | |
H14 | 0.1973 | 0.1542 | 0.2658 | 0.043* | |
C15 | 0.26085 (9) | 0.18207 (6) | 0.4040 (6) | 0.0401 (5) | |
H15 | 0.2385 | 0.1944 | 0.5228 | 0.048* | |
C16 | 0.31833 (9) | 0.18851 (5) | 0.3848 (5) | 0.0320 (5) | |
H16 | 0.3347 | 0.2053 | 0.4886 | 0.038* | |
C21 | 0.49942 (7) | 0.19862 (4) | 0.3606 (4) | 0.0197 (4) | |
C22 | 0.53631 (8) | 0.18872 (5) | 0.5573 (4) | 0.0240 (4) | |
H22 | 0.5244 | 0.1735 | 0.6867 | 0.029* | |
C23 | 0.59041 (9) | 0.20106 (5) | 0.5651 (4) | 0.0267 (4) | |
H23 | 0.6157 | 0.1943 | 0.6990 | 0.032* | |
C24 | 0.60706 (8) | 0.22331 (4) | 0.3755 (4) | 0.0251 (4) | |
C25 | 0.57105 (8) | 0.23332 (5) | 0.1771 (4) | 0.0260 (4) | |
H25 | 0.5833 | 0.2485 | 0.0476 | 0.031* | |
C26 | 0.51674 (8) | 0.22091 (4) | 0.1699 (4) | 0.0230 (4) | |
H26 | 0.4916 | 0.2276 | 0.0354 | 0.028* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0231 (3) | 0.0424 (3) | 0.0512 (3) | −0.0075 (2) | −0.0017 (2) | 0.0032 (3) |
C1 | 0.0232 (9) | 0.0261 (9) | 0.0170 (9) | −0.0025 (7) | 0.0021 (8) | −0.0016 (8) |
O1 | 0.0297 (8) | 0.0608 (10) | 0.0161 (8) | −0.0190 (7) | 0.0022 (6) | −0.0030 (7) |
N1 | 0.0236 (8) | 0.0275 (8) | 0.0134 (8) | −0.0042 (6) | 0.0022 (7) | 0.0016 (7) |
N2 | 0.0248 (8) | 0.0264 (8) | 0.0296 (9) | −0.0019 (7) | −0.0011 (8) | −0.0049 (7) |
O2 | 0.0273 (9) | 0.0520 (10) | 0.0445 (10) | 0.0115 (7) | −0.0022 (7) | −0.0088 (8) |
O3 | 0.0438 (10) | 0.0580 (10) | 0.0424 (10) | −0.0010 (8) | −0.0110 (8) | −0.0273 (8) |
C11 | 0.0236 (10) | 0.0245 (9) | 0.0185 (10) | −0.0012 (7) | 0.0005 (7) | 0.0015 (7) |
C12 | 0.0230 (10) | 0.0232 (8) | 0.0198 (9) | 0.0006 (7) | 0.0011 (8) | 0.0013 (7) |
C13 | 0.0220 (10) | 0.0316 (10) | 0.0352 (12) | −0.0020 (7) | −0.0041 (9) | 0.0046 (9) |
C14 | 0.0201 (10) | 0.0446 (12) | 0.0432 (13) | 0.0004 (9) | 0.0032 (9) | 0.0062 (10) |
C15 | 0.0303 (11) | 0.0447 (12) | 0.0453 (14) | 0.0078 (10) | 0.0136 (11) | −0.0048 (11) |
C16 | 0.0320 (11) | 0.0348 (10) | 0.0294 (11) | −0.0002 (8) | 0.0055 (9) | −0.0071 (10) |
C21 | 0.0223 (9) | 0.0194 (8) | 0.0173 (8) | −0.0013 (7) | −0.0001 (7) | −0.0028 (7) |
C22 | 0.0270 (10) | 0.0256 (8) | 0.0196 (9) | 0.0012 (8) | 0.0014 (7) | 0.0030 (7) |
C23 | 0.0240 (10) | 0.0310 (10) | 0.0252 (10) | 0.0043 (8) | −0.0037 (8) | 0.0010 (8) |
C24 | 0.0205 (9) | 0.0251 (9) | 0.0298 (11) | −0.0016 (7) | 0.0029 (8) | −0.0055 (8) |
C25 | 0.0295 (10) | 0.0233 (8) | 0.0252 (11) | −0.0040 (7) | 0.0036 (8) | 0.0009 (8) |
C26 | 0.0272 (9) | 0.0233 (8) | 0.0185 (9) | −0.0026 (7) | −0.0001 (8) | −0.0001 (7) |
Cl1—C24 | 1.7522 (19) | C14—H14 | 0.9500 |
C1—O1 | 1.224 (3) | C15—C16 | 1.400 (3) |
C1—N1 | 1.352 (3) | C15—H15 | 0.9500 |
C1—C11 | 1.500 (3) | C16—H16 | 0.9500 |
N1—C21 | 1.426 (2) | C21—C22 | 1.392 (3) |
N1—H1 | 0.88 (3) | C21—C26 | 1.393 (3) |
N2—O2 | 1.218 (2) | C22—C23 | 1.386 (3) |
N2—O3 | 1.229 (3) | C22—H22 | 0.9500 |
N2—C12 | 1.469 (3) | C23—C24 | 1.384 (3) |
C11—C16 | 1.390 (3) | C23—H23 | 0.9500 |
C11—C12 | 1.399 (3) | C24—C25 | 1.386 (3) |
C12—C13 | 1.379 (3) | C25—C26 | 1.392 (3) |
C13—C14 | 1.389 (3) | C25—H25 | 0.9500 |
C13—H13 | 0.9500 | C26—H26 | 0.9500 |
C14—C15 | 1.375 (4) | ||
O1—C1—N1 | 123.72 (17) | C16—C15—H15 | 119.7 |
O1—C1—C11 | 120.40 (17) | C11—C16—C15 | 120.1 (2) |
N1—C1—C11 | 115.83 (17) | C11—C16—H16 | 119.9 |
C1—N1—C21 | 125.47 (16) | C15—C16—H16 | 119.9 |
C1—N1—H1 | 118.3 (16) | C22—C21—C26 | 120.14 (16) |
C21—N1—H1 | 116.2 (16) | C22—C21—N1 | 118.19 (16) |
O2—N2—O3 | 123.93 (19) | C26—C21—N1 | 121.59 (17) |
O2—N2—C12 | 117.93 (17) | C23—C22—C21 | 120.22 (17) |
O3—N2—C12 | 118.10 (17) | C23—C22—H22 | 119.9 |
C16—C11—C12 | 117.46 (18) | C21—C22—H22 | 119.9 |
C16—C11—C1 | 121.20 (18) | C24—C23—C22 | 119.14 (18) |
C12—C11—C1 | 120.75 (17) | C24—C23—H23 | 120.4 |
C13—C12—C11 | 122.96 (18) | C22—C23—H23 | 120.4 |
C13—C12—N2 | 117.26 (17) | C23—C24—C25 | 121.51 (17) |
C11—C12—N2 | 119.64 (16) | C23—C24—Cl1 | 119.15 (16) |
C12—C13—C14 | 118.3 (2) | C25—C24—Cl1 | 119.33 (15) |
C12—C13—H13 | 120.9 | C24—C25—C26 | 119.21 (18) |
C14—C13—H13 | 120.9 | C24—C25—H25 | 120.4 |
C15—C14—C13 | 120.4 (2) | C26—C25—H25 | 120.4 |
C15—C14—H14 | 119.8 | C25—C26—C21 | 119.78 (18) |
C13—C14—H14 | 119.8 | C25—C26—H26 | 120.1 |
C14—C15—C16 | 120.7 (2) | C21—C26—H26 | 120.1 |
C14—C15—H15 | 119.7 | ||
O1—C1—N1—C21 | 2.6 (3) | C13—C14—C15—C16 | 1.0 (4) |
C11—C1—N1—C21 | −175.00 (16) | C12—C11—C16—C15 | −1.3 (3) |
O1—C1—C11—C16 | −128.4 (2) | C1—C11—C16—C15 | 170.0 (2) |
N1—C1—C11—C16 | 49.3 (3) | C14—C15—C16—C11 | −0.8 (4) |
O1—C1—C11—C12 | 42.6 (3) | C1—N1—C21—C22 | −147.03 (19) |
N1—C1—C11—C12 | −139.74 (19) | C1—N1—C21—C26 | 36.1 (3) |
C16—C11—C12—C13 | 3.3 (3) | C26—C21—C22—C23 | 0.2 (3) |
C1—C11—C12—C13 | −168.00 (18) | N1—C21—C22—C23 | −176.74 (17) |
C16—C11—C12—N2 | −172.14 (18) | C21—C22—C23—C24 | 0.1 (3) |
C1—C11—C12—N2 | 16.5 (3) | C22—C23—C24—C25 | −0.5 (3) |
O2—N2—C12—C13 | −137.1 (2) | C22—C23—C24—Cl1 | 178.17 (15) |
O3—N2—C12—C13 | 40.6 (3) | C23—C24—C25—C26 | 0.6 (3) |
O2—N2—C12—C11 | 38.6 (3) | Cl1—C24—C25—C26 | −178.13 (14) |
O3—N2—C12—C11 | −143.7 (2) | C24—C25—C26—C21 | −0.2 (3) |
C11—C12—C13—C14 | −3.1 (3) | C22—C21—C26—C25 | −0.1 (3) |
N2—C12—C13—C14 | 172.42 (18) | N1—C21—C26—C25 | 176.67 (17) |
C12—C13—C14—C15 | 0.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (3) | 2.05 (3) | 2.874 (2) | 157 (2) |
Symmetry code: (i) x, y, z+1. |
Experimental details
Crystal data | |
Chemical formula | C13H9ClN2O3 |
Mr | 276.67 |
Crystal system, space group | Orthorhombic, Fdd2 |
Temperature (K) | 173 |
a, b, c (Å) | 23.8527 (15), 40.936 (3), 5.0780 (4) |
V (Å3) | 4958.3 (6) |
Z | 16 |
Radiation type | Mo Kα |
µ (mm−1) | 0.31 |
Crystal size (mm) | 0.33 × 0.12 × 0.11 |
Data collection | |
Diffractometer | STOE IPDS II two-circle- diffractometer |
Absorption correction | Multi-scan (MULABS; Spek, 2003; Blessing, 1995) |
Tmin, Tmax | 0.904, 0.956 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10236, 2181, 2083 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.034, 0.090, 1.04 |
No. of reflections | 2181 |
No. of parameters | 176 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.23 |
Absolute structure | Flack (1983), 955 Friedel pairs |
Absolute structure parameter | 0.00 (6) |
Computer programs: X-AREA (Stoe & Cie, 2001), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.88 (3) | 2.05 (3) | 2.874 (2) | 157 (2) |
Symmetry code: (i) x, y, z+1. |
The benzanilide core is present in compounds with such a wide range of biological activities that it has been called a privileged structure (e.g. Makino et al., 2003; Igawa et al., 1999). As part of our studies in this area, the synthesis and structure of the title compound, (I), is now presented.
The geometric parameters for (I) are in the usual ranges. The dihedral angle between the two aromatic rings is 82.71 (6)°. The nitro group is twisted by 40.6 (2)° from the plane of the phenyl ring to which it is attached (Fig. 1). The crystal packing is stabilized by an N—H···O hydrogen bond (Table 1), leading to C(4) chains propagating in [001].