Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807031649/bt2406sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807031649/bt2406Isup2.hkl |
CCDC reference: 657657
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (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
For related literature, see: Gowda & Weiss (1994); Gowda et al. (2007, 2007a, 2007b, 2007c).
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.
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.
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).
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.
C8H7ClN2O3 | Dx = 1.590 Mg m−3 |
Mr = 214.61 | Cu Kα radiation, λ = 1.54180 Å |
Tetragonal, P43 | Cell parameters from 25 reflections |
Hall symbol: P 4cw | θ = 9.0–25.8° |
a = 4.999 (2) Å | µ = 3.67 mm−1 |
c = 35.876 (6) Å | T = 299 K |
V = 896.5 (5) Å3 | Prism, dark orange |
Z = 4 | 0.60 × 0.60 × 0.45 mm |
F(000) = 440 |
Enraf–Nonius CAD-4 diffractometer | 686 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.162 |
Graphite monochromator | θmax = 67.1°, θmin = 4.9° |
ω/2θ scans | h = 0→5 |
Absorption correction: ψ scan (North et al., 1968) | k = −5→5 |
Tmin = 0.220, Tmax = 0.276 | l = −42→0 |
1784 measured reflections | 3 standard reflections every 120 min |
810 independent reflections | intensity decay: 1.0% |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-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 = 1.13 | Δρmax = 0.31 e Å−3 |
810 reflections | Δρmin = −0.40 e Å−3 |
128 parameters | Extinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.022 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983), with no Friedel pairs |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.03 (4) |
C8H7ClN2O3 | Z = 4 |
Mr = 214.61 | Cu Kα radiation |
Tetragonal, P43 | µ = 3.67 mm−1 |
a = 4.999 (2) Å | T = 299 K |
c = 35.876 (6) Å | 0.60 × 0.60 × 0.45 mm |
V = 896.5 (5) Å3 |
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 = 0.276 | 3 standard reflections every 120 min |
1784 measured reflections | intensity decay: 1.0% |
810 independent reflections |
R[F2 > 2σ(F2)] = 0.066 | H-atom parameters constrained |
wR(F2) = 0.188 | Δρmax = 0.31 e Å−3 |
S = 1.13 | Δρmin = −0.40 e Å−3 |
810 reflections | Absolute structure: Flack (1983), with no Friedel pairs |
128 parameters | Absolute structure parameter: 0.03 (4) |
1 restraint |
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 | ||
C2 | −0.3115 (17) | 0.3054 (16) | 0.15620 (18) | 0.058 (2) | |
H2B | −0.3817 | 0.4858 | 0.1543 | 0.070* | |
H2A | −0.1869 | 0.3003 | 0.1769 | 0.070* | |
C3 | −0.1668 (14) | 0.2336 (13) | 0.12061 (17) | 0.0444 (16) | |
C6 | 0.1238 (13) | 0.4335 (12) | 0.07257 (17) | 0.0414 (14) | |
C7 | 0.0760 (14) | 0.2529 (14) | 0.04397 (18) | 0.0487 (16) | |
H7 | −0.0619 | 0.1287 | 0.0457 | 0.058* | |
C8 | 0.2381 (14) | 0.2624 (15) | 0.01301 (17) | 0.0484 (16) | |
C9 | 0.4455 (15) | 0.4393 (16) | 0.0093 (3) | 0.062 (2) | |
H9 | 0.5530 | 0.4392 | −0.0118 | 0.074* | |
C10 | 0.4895 (17) | 0.6160 (16) | 0.0377 (2) | 0.061 (2) | |
H10 | 0.6290 | 0.7382 | 0.0358 | 0.073* | |
C11 | 0.3318 (14) | 0.6165 (12) | 0.0690 (2) | 0.0505 (16) | |
H11 | 0.3641 | 0.7397 | 0.0879 | 0.061* | |
Cl1 | −0.5750 (3) | 0.0811 (4) | 0.16453 (4) | 0.0687 (8) | |
N5 | −0.0402 (12) | 0.4416 (10) | 0.10456 (15) | 0.0455 (14) | |
H5N | −0.0616 | 0.5954 | 0.1149 | 0.055* | |
N12 | 0.1788 (14) | 0.0720 (13) | −0.01703 (17) | 0.0581 (16) | |
O4 | −0.1610 (12) | 0.0095 (10) | 0.10761 (15) | 0.0587 (14) | |
O13 | −0.0164 (16) | −0.0715 (14) | −0.01436 (19) | 0.083 (2) | |
O14 | 0.3341 (15) | 0.0670 (15) | −0.04350 (16) | 0.084 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.065 (5) | 0.049 (4) | 0.061 (4) | −0.003 (4) | 0.008 (3) | −0.008 (3) |
C3 | 0.045 (4) | 0.031 (3) | 0.058 (3) | −0.001 (2) | −0.003 (3) | −0.007 (3) |
C6 | 0.039 (3) | 0.030 (3) | 0.055 (3) | 0.003 (2) | 0.000 (3) | 0.002 (3) |
C7 | 0.043 (4) | 0.043 (3) | 0.060 (3) | 0.006 (3) | 0.000 (3) | −0.001 (3) |
C8 | 0.047 (4) | 0.044 (3) | 0.054 (3) | 0.012 (3) | −0.001 (3) | 0.000 (3) |
C9 | 0.040 (4) | 0.062 (5) | 0.082 (4) | 0.012 (4) | 0.008 (3) | 0.021 (4) |
C10 | 0.049 (4) | 0.048 (4) | 0.086 (5) | −0.003 (4) | 0.002 (4) | 0.010 (4) |
C11 | 0.045 (4) | 0.027 (3) | 0.079 (4) | 0.002 (3) | −0.006 (3) | −0.001 (3) |
Cl1 | 0.0534 (13) | 0.0763 (15) | 0.0765 (11) | −0.0104 (8) | 0.0105 (8) | −0.0069 (9) |
N5 | 0.053 (3) | 0.028 (3) | 0.055 (3) | −0.001 (2) | 0.001 (3) | −0.008 (2) |
N12 | 0.061 (4) | 0.054 (4) | 0.059 (3) | 0.019 (3) | −0.006 (3) | −0.002 (3) |
O4 | 0.067 (3) | 0.035 (3) | 0.074 (3) | 0.000 (2) | 0.011 (3) | −0.004 (2) |
O13 | 0.084 (4) | 0.077 (5) | 0.086 (4) | −0.012 (4) | −0.007 (4) | −0.022 (3) |
O14 | 0.083 (4) | 0.103 (5) | 0.067 (3) | 0.029 (4) | 0.022 (3) | −0.014 (3) |
C2—C3 | 1.510 (9) | C8—C9 | 1.369 (11) |
C2—Cl1 | 1.756 (8) | C8—N12 | 1.468 (10) |
C2—H2B | 0.9700 | C9—C10 | 1.365 (13) |
C2—H2A | 0.9700 | C9—H9 | 0.9300 |
C3—O4 | 1.214 (8) | C10—C11 | 1.372 (12) |
C3—N5 | 1.347 (9) | C10—H10 | 0.9300 |
C6—C7 | 1.388 (9) | C11—H11 | 0.9300 |
C6—C11 | 1.391 (9) | N5—H5N | 0.8600 |
C6—N5 | 1.411 (9) | N12—O13 | 1.215 (10) |
C7—C8 | 1.376 (9) | N12—O14 | 1.227 (9) |
C7—H7 | 0.9300 | ||
C3—C2—Cl1 | 110.6 (5) | C7—C8—N12 | 116.8 (7) |
C3—C2—H2B | 109.5 | C10—C9—C8 | 117.9 (8) |
Cl1—C2—H2B | 109.5 | C10—C9—H9 | 121.1 |
C3—C2—H2A | 109.5 | C8—C9—H9 | 121.1 |
Cl1—C2—H2A | 109.5 | C9—C10—C11 | 121.3 (8) |
H2B—C2—H2A | 108.1 | C9—C10—H10 | 119.4 |
O4—C3—N5 | 122.5 (6) | C11—C10—H10 | 119.4 |
O4—C3—C2 | 123.7 (6) | C10—C11—C6 | 120.3 (7) |
N5—C3—C2 | 113.8 (6) | C10—C11—H11 | 119.9 |
C7—C6—C11 | 119.2 (6) | C6—C11—H11 | 119.9 |
C7—C6—N5 | 121.3 (6) | C3—N5—C6 | 126.8 (5) |
C11—C6—N5 | 119.4 (6) | C3—N5—H5N | 116.6 |
C8—C7—C6 | 118.2 (6) | C6—N5—H5N | 116.6 |
C8—C7—H7 | 120.9 | O13—N12—O14 | 123.9 (7) |
C6—C7—H7 | 120.9 | O13—N12—C8 | 119.1 (6) |
C9—C8—C7 | 123.1 (7) | O14—N12—C8 | 117.0 (7) |
C9—C8—N12 | 120.0 (7) | ||
Cl1—C2—C3—O4 | −25.7 (9) | C7—C6—C11—C10 | −0.7 (10) |
Cl1—C2—C3—N5 | 155.1 (5) | N5—C6—C11—C10 | −178.4 (6) |
C11—C6—C7—C8 | 0.1 (9) | O4—C3—N5—C6 | −3.3 (11) |
N5—C6—C7—C8 | 177.7 (6) | C2—C3—N5—C6 | 175.9 (7) |
C6—C7—C8—C9 | 0.8 (10) | C7—C6—N5—C3 | 32.2 (10) |
C6—C7—C8—N12 | −178.9 (6) | C11—C6—N5—C3 | −150.1 (6) |
C7—C8—C9—C10 | −0.9 (11) | C9—C8—N12—O13 | −175.2 (8) |
N12—C8—C9—C10 | 178.8 (7) | C7—C8—N12—O13 | 4.4 (10) |
C8—C9—C10—C11 | 0.1 (11) | C9—C8—N12—O14 | 5.4 (9) |
C9—C10—C11—C6 | 0.6 (11) | C7—C8—N12—O14 | −175.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.86 | 2.14 | 2.904 (7) | 147 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C8H7ClN2O3 |
Mr | 214.61 |
Crystal system, space group | Tetragonal, P43 |
Temperature (K) | 299 |
a, c (Å) | 4.999 (2), 35.876 (6) |
V (Å3) | 896.5 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 3.67 |
Crystal size (mm) | 0.60 × 0.60 × 0.45 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.220, 0.276 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1784, 810, 686 |
Rint | 0.162 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.066, 0.188, 1.13 |
No. of reflections | 810 |
No. of parameters | 128 |
No. of restraints | 1 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.40 |
Absolute structure | Flack (1983), with no Friedel pairs |
Absolute structure parameter | 0.03 (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.
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.86 | 2.14 | 2.904 (7) | 147.0 |
Symmetry code: (i) x, y+1, z. |
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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).