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In the title compound, C13H9ClN2O3, 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 its attached benzene ring. The packing is stabilized by an N—H...O hydrogen bond.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807055742/hb2615sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807055742/hb2615Isup2.hkl
Contains datablock I

CCDC reference: 674080

Key indicators

  • Single-crystal X-ray study
  • T = 173 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.034
  • wR factor = 0.090
  • Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 1.01 PLAT850_ALERT_2_C Check Flack Parameter Exact Value 0.00 and su .. 0.06
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 25.02 From the CIF: _reflns_number_total 2181 Count of symmetry unique reflns 1230 Completeness (_total/calc) 177.32% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 951 Fraction of Friedel pairs measured 0.773 Are heavy atom types Z>Si present yes PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 2 ALERT level G = General alerts; check 0 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 1 ALERT type 3 Indicator that the structure quality may be low 2 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 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].

Related literature top

For background, see: Makino et al. (2003); Igawa et al. (1999).

Experimental top

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).

Refinement top

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.

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, 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).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I) with displacement ellipsoids for the non-hydrogen atoms at the 50% probability level.
N-(4-Chlorophenyl)-2-nitrobenzamide top
Crystal data top
C13H9ClN2O3F(000) = 2272
Mr = 276.67Dx = 1.483 Mg m3
Orthorhombic, Fdd2Mo Kα radiation, λ = 0.71073 Å
Hall symbol: F 2 -2dCell parameters from 9190 reflections
a = 23.8527 (15) Åθ = 2.8–25.2°
b = 40.936 (3) ŵ = 0.31 mm1
c = 5.0780 (4) ÅT = 173 K
V = 4958.3 (6) Å3Needle, colourless
Z = 160.33 × 0.12 × 0.11 mm
Data collection top
STOE IPDS II two-circle-
diffractometer
2181 independent reflections
Radiation source: fine-focus sealed tube2083 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.071
ω scansθmax = 25.0°, θmin = 2.6°
Absorption correction: multi-scan
(MULABS; Spek, 2003; Blessing, 1995)
h = 2628
Tmin = 0.904, Tmax = 0.956k = 4048
10236 measured reflectionsl = 66
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) = 0.090 w = 1/[σ2(Fo2) + (0.0698P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.04(Δ/σ)max = 0.001
2181 reflectionsΔρmax = 0.16 e Å3
176 parametersΔρmin = 0.23 e Å3
1 restraintAbsolute structure: Flack (1983), 955 Friedel pairs
Primary atom site location: structure-invariant direct methodsAbsolute structure parameter: 0.00 (6)
Crystal data top
C13H9ClN2O3V = 4958.3 (6) Å3
Mr = 276.67Z = 16
Orthorhombic, Fdd2Mo Kα radiation
a = 23.8527 (15) ŵ = 0.31 mm1
b = 40.936 (3) ÅT = 173 K
c = 5.0780 (4) Å0.33 × 0.12 × 0.11 mm
Data collection top
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 = 0.956Rint = 0.071
10236 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.090Δρmax = 0.16 e Å3
S = 1.04Δρmin = 0.23 e Å3
2181 reflectionsAbsolute structure: Flack (1983), 955 Friedel pairs
176 parametersAbsolute structure parameter: 0.00 (6)
1 restraint
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
Cl10.67478 (2)0.239794 (13)0.39083 (13)0.03892 (17)
C10.41096 (8)0.18013 (4)0.1564 (4)0.0221 (4)
O10.42715 (6)0.18287 (4)0.0713 (3)0.0355 (4)
N10.44331 (7)0.18661 (4)0.3687 (3)0.0215 (3)
H10.4295 (10)0.1826 (6)0.526 (6)0.026 (6)*
N20.35978 (7)0.12292 (4)0.0872 (4)0.0269 (4)
O20.40437 (7)0.11395 (4)0.0044 (4)0.0413 (4)
O30.34094 (7)0.11341 (5)0.2990 (4)0.0481 (5)
C110.35158 (8)0.17038 (5)0.2139 (3)0.0222 (4)
C120.32552 (8)0.14551 (5)0.0699 (4)0.0220 (4)
C130.26869 (9)0.13956 (5)0.0811 (4)0.0296 (5)
H130.25200.12320.02580.036*
C140.23644 (9)0.15811 (6)0.2528 (5)0.0360 (5)
H140.19730.15420.26580.043*
C150.26085 (9)0.18207 (6)0.4040 (6)0.0401 (5)
H150.23850.19440.52280.048*
C160.31833 (9)0.18851 (5)0.3848 (5)0.0320 (5)
H160.33470.20530.48860.038*
C210.49942 (7)0.19862 (4)0.3606 (4)0.0197 (4)
C220.53631 (8)0.18872 (5)0.5573 (4)0.0240 (4)
H220.52440.17350.68670.029*
C230.59041 (9)0.20106 (5)0.5651 (4)0.0267 (4)
H230.61570.19430.69900.032*
C240.60706 (8)0.22331 (4)0.3755 (4)0.0251 (4)
C250.57105 (8)0.23332 (5)0.1771 (4)0.0260 (4)
H250.58330.24850.04760.031*
C260.51674 (8)0.22091 (4)0.1699 (4)0.0230 (4)
H260.49160.22760.03540.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0231 (3)0.0424 (3)0.0512 (3)0.0075 (2)0.0017 (2)0.0032 (3)
C10.0232 (9)0.0261 (9)0.0170 (9)0.0025 (7)0.0021 (8)0.0016 (8)
O10.0297 (8)0.0608 (10)0.0161 (8)0.0190 (7)0.0022 (6)0.0030 (7)
N10.0236 (8)0.0275 (8)0.0134 (8)0.0042 (6)0.0022 (7)0.0016 (7)
N20.0248 (8)0.0264 (8)0.0296 (9)0.0019 (7)0.0011 (8)0.0049 (7)
O20.0273 (9)0.0520 (10)0.0445 (10)0.0115 (7)0.0022 (7)0.0088 (8)
O30.0438 (10)0.0580 (10)0.0424 (10)0.0010 (8)0.0110 (8)0.0273 (8)
C110.0236 (10)0.0245 (9)0.0185 (10)0.0012 (7)0.0005 (7)0.0015 (7)
C120.0230 (10)0.0232 (8)0.0198 (9)0.0006 (7)0.0011 (8)0.0013 (7)
C130.0220 (10)0.0316 (10)0.0352 (12)0.0020 (7)0.0041 (9)0.0046 (9)
C140.0201 (10)0.0446 (12)0.0432 (13)0.0004 (9)0.0032 (9)0.0062 (10)
C150.0303 (11)0.0447 (12)0.0453 (14)0.0078 (10)0.0136 (11)0.0048 (11)
C160.0320 (11)0.0348 (10)0.0294 (11)0.0002 (8)0.0055 (9)0.0071 (10)
C210.0223 (9)0.0194 (8)0.0173 (8)0.0013 (7)0.0001 (7)0.0028 (7)
C220.0270 (10)0.0256 (8)0.0196 (9)0.0012 (8)0.0014 (7)0.0030 (7)
C230.0240 (10)0.0310 (10)0.0252 (10)0.0043 (8)0.0037 (8)0.0010 (8)
C240.0205 (9)0.0251 (9)0.0298 (11)0.0016 (7)0.0029 (8)0.0055 (8)
C250.0295 (10)0.0233 (8)0.0252 (11)0.0040 (7)0.0036 (8)0.0009 (8)
C260.0272 (9)0.0233 (8)0.0185 (9)0.0026 (7)0.0001 (8)0.0001 (7)
Geometric parameters (Å, º) top
Cl1—C241.7522 (19)C14—H140.9500
C1—O11.224 (3)C15—C161.400 (3)
C1—N11.352 (3)C15—H150.9500
C1—C111.500 (3)C16—H160.9500
N1—C211.426 (2)C21—C221.392 (3)
N1—H10.88 (3)C21—C261.393 (3)
N2—O21.218 (2)C22—C231.386 (3)
N2—O31.229 (3)C22—H220.9500
N2—C121.469 (3)C23—C241.384 (3)
C11—C161.390 (3)C23—H230.9500
C11—C121.399 (3)C24—C251.386 (3)
C12—C131.379 (3)C25—C261.392 (3)
C13—C141.389 (3)C25—H250.9500
C13—H130.9500C26—H260.9500
C14—C151.375 (4)
O1—C1—N1123.72 (17)C16—C15—H15119.7
O1—C1—C11120.40 (17)C11—C16—C15120.1 (2)
N1—C1—C11115.83 (17)C11—C16—H16119.9
C1—N1—C21125.47 (16)C15—C16—H16119.9
C1—N1—H1118.3 (16)C22—C21—C26120.14 (16)
C21—N1—H1116.2 (16)C22—C21—N1118.19 (16)
O2—N2—O3123.93 (19)C26—C21—N1121.59 (17)
O2—N2—C12117.93 (17)C23—C22—C21120.22 (17)
O3—N2—C12118.10 (17)C23—C22—H22119.9
C16—C11—C12117.46 (18)C21—C22—H22119.9
C16—C11—C1121.20 (18)C24—C23—C22119.14 (18)
C12—C11—C1120.75 (17)C24—C23—H23120.4
C13—C12—C11122.96 (18)C22—C23—H23120.4
C13—C12—N2117.26 (17)C23—C24—C25121.51 (17)
C11—C12—N2119.64 (16)C23—C24—Cl1119.15 (16)
C12—C13—C14118.3 (2)C25—C24—Cl1119.33 (15)
C12—C13—H13120.9C24—C25—C26119.21 (18)
C14—C13—H13120.9C24—C25—H25120.4
C15—C14—C13120.4 (2)C26—C25—H25120.4
C15—C14—H14119.8C25—C26—C21119.78 (18)
C13—C14—H14119.8C25—C26—H26120.1
C14—C15—C16120.7 (2)C21—C26—H26120.1
C14—C15—H15119.7
O1—C1—N1—C212.6 (3)C13—C14—C15—C161.0 (4)
C11—C1—N1—C21175.00 (16)C12—C11—C16—C151.3 (3)
O1—C1—C11—C16128.4 (2)C1—C11—C16—C15170.0 (2)
N1—C1—C11—C1649.3 (3)C14—C15—C16—C110.8 (4)
O1—C1—C11—C1242.6 (3)C1—N1—C21—C22147.03 (19)
N1—C1—C11—C12139.74 (19)C1—N1—C21—C2636.1 (3)
C16—C11—C12—C133.3 (3)C26—C21—C22—C230.2 (3)
C1—C11—C12—C13168.00 (18)N1—C21—C22—C23176.74 (17)
C16—C11—C12—N2172.14 (18)C21—C22—C23—C240.1 (3)
C1—C11—C12—N216.5 (3)C22—C23—C24—C250.5 (3)
O2—N2—C12—C13137.1 (2)C22—C23—C24—Cl1178.17 (15)
O3—N2—C12—C1340.6 (3)C23—C24—C25—C260.6 (3)
O2—N2—C12—C1138.6 (3)Cl1—C24—C25—C26178.13 (14)
O3—N2—C12—C11143.7 (2)C24—C25—C26—C210.2 (3)
C11—C12—C13—C143.1 (3)C22—C21—C26—C250.1 (3)
N2—C12—C13—C14172.42 (18)N1—C21—C26—C25176.67 (17)
C12—C13—C14—C150.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (3)2.05 (3)2.874 (2)157 (2)
Symmetry code: (i) x, y, z+1.

Experimental details

Crystal data
Chemical formulaC13H9ClN2O3
Mr276.67
Crystal system, space groupOrthorhombic, Fdd2
Temperature (K)173
a, b, c (Å)23.8527 (15), 40.936 (3), 5.0780 (4)
V3)4958.3 (6)
Z16
Radiation typeMo Kα
µ (mm1)0.31
Crystal size (mm)0.33 × 0.12 × 0.11
Data collection
DiffractometerSTOE IPDS II two-circle-
diffractometer
Absorption correctionMulti-scan
(MULABS; Spek, 2003; Blessing, 1995)
Tmin, Tmax0.904, 0.956
No. of measured, independent and
observed [I > 2σ(I)] reflections
10236, 2181, 2083
Rint0.071
(sin θ/λ)max1)0.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.090, 1.04
No. of reflections2181
No. of parameters176
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.16, 0.23
Absolute structureFlack (1983), 955 Friedel pairs
Absolute structure parameter0.00 (6)

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

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.88 (3)2.05 (3)2.874 (2)157 (2)
Symmetry code: (i) x, y, z+1.
 

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