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The conformation of the N—H bond in the structure of the title compound, C8H7ClN2O3, is anti to the meta-nitro group, in contrast with the syn conformation observed with respect to the ortho-nitro substituent in 2-chloro-N-(2-nitro­phenyl)­acetamide. The geometric parameters of the title compound are similar to those of 2-chloro-N-(4-nitro­phenyl)­acetamide and other acetanilides. Inter­molecular N—H...O hydrogen bonds link the mol­ecules into zigzag chains running along the a and b axes.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031649/bt2406sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031649/bt2406Isup2.hkl
Contains datablock I

CCDC reference: 657657

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](C-C) = 0.010 Å
  • R factor = 0.065
  • wR factor = 0.188
  • Data-to-parameter ratio = 6.3

checkCIF/PLATON results

No syntax errors found



Alert level B RINTA01_ALERT_3_B The value of Rint is greater than 0.15 Rint given 0.162 PLAT020_ALERT_3_B The value of Rint is greater than 0.10 ......... 0.16
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.69 PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.33 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 10 PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. O14 .. 3.13 Ang. PLAT431_ALERT_2_C Short Inter HL..A Contact Cl1 .. N12 .. 3.29 Ang.
Alert level G ABSTM02_ALERT_3_G When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.695 Tmax scaled 0.192 Tmin scaled 0.153 REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 67.05 From the CIF: _reflns_number_total 810 Count of symmetry unique reflns 809 Completeness (_total/calc) 100.12% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 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 2 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 3 ALERT level G = General alerts; check 0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 6 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 amide moiety is an important constituent of many biologically significant compounds. The structural studies of amides are therefore of interest. As part of a study of the effect of ring and side chain substitutions on the solid state structures of this class of compounds (Gowda et al., 2007a,b,c,d), the crystal structure of N-(3-nitrophenyl)-2-chloroacetamide has been determined to explore the effects of polar substituent groups on the structures of N-aromatic amides. The conformation of the N—H bond (Fig. 1) is anti to the meta nitro group, in contrast to the syn conformation observed with respect to ortho nitro substituent in N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a). The geometric parameters of are similar to those of N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a), N-(4-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007c) and other acetanilides (Gowda et al., 2007b, Gowda et al., 2007). The molecular skeleton is essentially planar. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into zigzag chains running along the a and b axis (Fig. 2).

Related literature top

For related literature, see: Gowda & Weiss (1994); Gowda et al. (2007, 2007a, 2007b, 2007c).

Experimental top

The title compound was prepared according to the literature method (Gowda & Weiss, 1994). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NQR spectra (Gowda & Weiss, 1994). Single crystals of the title compound were obtained from an ethanolic solution and used for X-ray diffraction studies at room temperature.

Refinement top

The H atoms were positioned with idealized geometry using a riding model with N—H = 0.86 Å and C—H = 0.93–0.97 Å]. Uiso(H) values were set equal to 1.2Ueq of the parent atom.

Structure description top

The amide moiety is an important constituent of many biologically significant compounds. The structural studies of amides are therefore of interest. As part of a study of the effect of ring and side chain substitutions on the solid state structures of this class of compounds (Gowda et al., 2007a,b,c,d), the crystal structure of N-(3-nitrophenyl)-2-chloroacetamide has been determined to explore the effects of polar substituent groups on the structures of N-aromatic amides. The conformation of the N—H bond (Fig. 1) is anti to the meta nitro group, in contrast to the syn conformation observed with respect to ortho nitro substituent in N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a). The geometric parameters of are similar to those of N-(2-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007a), N-(4-nitrophenyl)-2-chloroacetamide (Gowda et al., 2007c) and other acetanilides (Gowda et al., 2007b, Gowda et al., 2007). The molecular skeleton is essentially planar. Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into zigzag chains running along the a and b axis (Fig. 2).

For related literature, see: Gowda & Weiss (1994); Gowda et al. (2007, 2007a, 2007b, 2007c).

Computing details top

Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software; data reduction: REDU4 (Stoe & Cie, 1987); 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.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Molecular packing of (I) with hydrogen bonding shown as dashed lines.
2-Chloro-N-(3-nitrophenyl)acetamide top
Crystal data top
C8H7ClN2O3Dx = 1.590 Mg m3
Mr = 214.61Cu Kα radiation, λ = 1.54180 Å
Tetragonal, P43Cell parameters from 25 reflections
Hall symbol: P 4cwθ = 9.0–25.8°
a = 4.999 (2) ŵ = 3.67 mm1
c = 35.876 (6) ÅT = 299 K
V = 896.5 (5) Å3Prism, dark orange
Z = 40.60 × 0.60 × 0.45 mm
F(000) = 440
Data collection top
Enraf–Nonius CAD-4
diffractometer
686 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.162
Graphite monochromatorθmax = 67.1°, θmin = 4.9°
ω/2θ scansh = 05
Absorption correction: ψ scan
(North et al., 1968)
k = 55
Tmin = 0.220, Tmax = 0.276l = 420
1784 measured reflections3 standard reflections every 120 min
810 independent reflections intensity decay: 1.0%
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH-atom parameters constrained
R[F2 > 2σ(F2)] = 0.066 w = 1/[σ2(Fo2) + (0.078P)2 + 0.1695P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.188(Δ/σ)max < 0.001
S = 1.13Δρmax = 0.31 e Å3
810 reflectionsΔρmin = 0.40 e Å3
128 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
1 restraintExtinction coefficient: 0.022 (5)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with no Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.03 (4)
Crystal data top
C8H7ClN2O3Z = 4
Mr = 214.61Cu Kα radiation
Tetragonal, P43µ = 3.67 mm1
a = 4.999 (2) ÅT = 299 K
c = 35.876 (6) Å0.60 × 0.60 × 0.45 mm
V = 896.5 (5) Å3
Data collection top
Enraf–Nonius CAD-4
diffractometer
686 reflections with I > 2σ(I)
Absorption correction: ψ scan
(North et al., 1968)
Rint = 0.162
Tmin = 0.220, Tmax = 0.2763 standard reflections every 120 min
1784 measured reflections intensity decay: 1.0%
810 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.066H-atom parameters constrained
wR(F2) = 0.188Δρmax = 0.31 e Å3
S = 1.13Δρmin = 0.40 e Å3
810 reflectionsAbsolute structure: Flack (1983), with no Friedel pairs
128 parametersAbsolute structure parameter: 0.03 (4)
1 restraint
Special details top

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
C20.3115 (17)0.3054 (16)0.15620 (18)0.058 (2)
H2B0.38170.48580.15430.070*
H2A0.18690.30030.17690.070*
C30.1668 (14)0.2336 (13)0.12061 (17)0.0444 (16)
C60.1238 (13)0.4335 (12)0.07257 (17)0.0414 (14)
C70.0760 (14)0.2529 (14)0.04397 (18)0.0487 (16)
H70.06190.12870.04570.058*
C80.2381 (14)0.2624 (15)0.01301 (17)0.0484 (16)
C90.4455 (15)0.4393 (16)0.0093 (3)0.062 (2)
H90.55300.43920.01180.074*
C100.4895 (17)0.6160 (16)0.0377 (2)0.061 (2)
H100.62900.73820.03580.073*
C110.3318 (14)0.6165 (12)0.0690 (2)0.0505 (16)
H110.36410.73970.08790.061*
Cl10.5750 (3)0.0811 (4)0.16453 (4)0.0687 (8)
N50.0402 (12)0.4416 (10)0.10456 (15)0.0455 (14)
H5N0.06160.59540.11490.055*
N120.1788 (14)0.0720 (13)0.01703 (17)0.0581 (16)
O40.1610 (12)0.0095 (10)0.10761 (15)0.0587 (14)
O130.0164 (16)0.0715 (14)0.01436 (19)0.083 (2)
O140.3341 (15)0.0670 (15)0.04350 (16)0.084 (2)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C20.065 (5)0.049 (4)0.061 (4)0.003 (4)0.008 (3)0.008 (3)
C30.045 (4)0.031 (3)0.058 (3)0.001 (2)0.003 (3)0.007 (3)
C60.039 (3)0.030 (3)0.055 (3)0.003 (2)0.000 (3)0.002 (3)
C70.043 (4)0.043 (3)0.060 (3)0.006 (3)0.000 (3)0.001 (3)
C80.047 (4)0.044 (3)0.054 (3)0.012 (3)0.001 (3)0.000 (3)
C90.040 (4)0.062 (5)0.082 (4)0.012 (4)0.008 (3)0.021 (4)
C100.049 (4)0.048 (4)0.086 (5)0.003 (4)0.002 (4)0.010 (4)
C110.045 (4)0.027 (3)0.079 (4)0.002 (3)0.006 (3)0.001 (3)
Cl10.0534 (13)0.0763 (15)0.0765 (11)0.0104 (8)0.0105 (8)0.0069 (9)
N50.053 (3)0.028 (3)0.055 (3)0.001 (2)0.001 (3)0.008 (2)
N120.061 (4)0.054 (4)0.059 (3)0.019 (3)0.006 (3)0.002 (3)
O40.067 (3)0.035 (3)0.074 (3)0.000 (2)0.011 (3)0.004 (2)
O130.084 (4)0.077 (5)0.086 (4)0.012 (4)0.007 (4)0.022 (3)
O140.083 (4)0.103 (5)0.067 (3)0.029 (4)0.022 (3)0.014 (3)
Geometric parameters (Å, º) top
C2—C31.510 (9)C8—C91.369 (11)
C2—Cl11.756 (8)C8—N121.468 (10)
C2—H2B0.9700C9—C101.365 (13)
C2—H2A0.9700C9—H90.9300
C3—O41.214 (8)C10—C111.372 (12)
C3—N51.347 (9)C10—H100.9300
C6—C71.388 (9)C11—H110.9300
C6—C111.391 (9)N5—H5N0.8600
C6—N51.411 (9)N12—O131.215 (10)
C7—C81.376 (9)N12—O141.227 (9)
C7—H70.9300
C3—C2—Cl1110.6 (5)C7—C8—N12116.8 (7)
C3—C2—H2B109.5C10—C9—C8117.9 (8)
Cl1—C2—H2B109.5C10—C9—H9121.1
C3—C2—H2A109.5C8—C9—H9121.1
Cl1—C2—H2A109.5C9—C10—C11121.3 (8)
H2B—C2—H2A108.1C9—C10—H10119.4
O4—C3—N5122.5 (6)C11—C10—H10119.4
O4—C3—C2123.7 (6)C10—C11—C6120.3 (7)
N5—C3—C2113.8 (6)C10—C11—H11119.9
C7—C6—C11119.2 (6)C6—C11—H11119.9
C7—C6—N5121.3 (6)C3—N5—C6126.8 (5)
C11—C6—N5119.4 (6)C3—N5—H5N116.6
C8—C7—C6118.2 (6)C6—N5—H5N116.6
C8—C7—H7120.9O13—N12—O14123.9 (7)
C6—C7—H7120.9O13—N12—C8119.1 (6)
C9—C8—C7123.1 (7)O14—N12—C8117.0 (7)
C9—C8—N12120.0 (7)
Cl1—C2—C3—O425.7 (9)C7—C6—C11—C100.7 (10)
Cl1—C2—C3—N5155.1 (5)N5—C6—C11—C10178.4 (6)
C11—C6—C7—C80.1 (9)O4—C3—N5—C63.3 (11)
N5—C6—C7—C8177.7 (6)C2—C3—N5—C6175.9 (7)
C6—C7—C8—C90.8 (10)C7—C6—N5—C332.2 (10)
C6—C7—C8—N12178.9 (6)C11—C6—N5—C3150.1 (6)
C7—C8—C9—C100.9 (11)C9—C8—N12—O13175.2 (8)
N12—C8—C9—C10178.8 (7)C7—C8—N12—O134.4 (10)
C8—C9—C10—C110.1 (11)C9—C8—N12—O145.4 (9)
C9—C10—C11—C60.6 (11)C7—C8—N12—O14175.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O4i0.862.142.904 (7)147
Symmetry code: (i) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC8H7ClN2O3
Mr214.61
Crystal system, space groupTetragonal, P43
Temperature (K)299
a, c (Å)4.999 (2), 35.876 (6)
V3)896.5 (5)
Z4
Radiation typeCu Kα
µ (mm1)3.67
Crystal size (mm)0.60 × 0.60 × 0.45
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionψ scan
(North et al., 1968)
Tmin, Tmax0.220, 0.276
No. of measured, independent and
observed [I > 2σ(I)] reflections
1784, 810, 686
Rint0.162
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.066, 0.188, 1.13
No. of reflections810
No. of parameters128
No. of restraints1
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.31, 0.40
Absolute structureFlack (1983), with no Friedel pairs
Absolute structure parameter0.03 (4)

Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), CAD-4-PC Software, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003), SHELXL97.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N5—H5N···O4i0.862.142.904 (7)147.0
Symmetry code: (i) x, y+1, z.
 

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