Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703187X/bt2420sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703187X/bt2420Isup2.hkl |
CCDC reference: 657678
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.055
- wR factor = 0.156
- Data-to-parameter ratio = 14.7
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT062_ALERT_4_C Rescale T(min) & T(max) by ..................... 0.29 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
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 0.286 Tmax scaled 0.057 Tmin scaled 0.026
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 1 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 2 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Gowda et al. (2000); Gowda, Kozisek et al. (2007); Gowda et al. (2007a,b,c); Pies et al. (1971); Shilpa & Gowda (2007).
The title compound was prepared according to the literature method (Shilpa & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR (Shilpa & Gowda, 2007) and NQR spectra (Pies et al., 1971). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution (2 g in about 30 ml e thanol) 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 Å]. Uiso(H) values were set equal to 1.2 Ueq of the parent atom.
In the present work, the structure of N-(2,4-dichlorophenyl)-2,2,2- trichloroacetamide has been determined as part of a study in the direction of systematization of the crystal structures of N-aromatic amides (Gowda et al., 2000; 2007a, b, c, d). The conformation of the N—H bond is syn to the ortho-chloro substituent (Fig. 1), similar to that observed in N-(2-chlorophenyl)-acetamide (Gowda et al., 2007c), N-(2,4-DiChlorophenyl)-acetamide (Gowda et al., 2007d), N-(2-chlorophenyl)-2,2,2- trichloroacetamide (Gowda et al., 2000) and N-(2-chlorophenyl)- 2,2,2-trimethylacetamide (Gowda et al., 2007b). The geometric parameters are similar to those in other acetanilides (Gowda et al., 2000; 2007a, b, c, d). The amide H is involved in two intra-molecular hydrogen bonding with the ortho ring Cl atom and one of the Cl atoms of the CCl3 group (Fig. 1) (Fig. 2 & Table 1).
For related literature, see: Gowda et al. (2000); Gowda, Kozisek et al. (2007); Gowda et al. (2007a,b,c); Pies et al. (1971); Shilpa & Gowda (2007).
Data collection: CAD-4-PC (Enraf-Nonius, 1996); cell refinement: CAD-4-PC; 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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C8H4Cl5NO | F(000) = 1216 |
Mr = 307.37 | Dx = 1.807 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 14.306 (2) Å | θ = 5.7–19.1° |
b = 8.625 (2) Å | µ = 11.47 mm−1 |
c = 18.317 (4) Å | T = 299 K |
V = 2260.1 (8) Å3 | Rod, colourless |
Z = 8 | 0.40 × 0.25 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | 1780 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 67.0°, θmin = 4.8° |
ω/2θ scans | h = −17→0 |
Absorption correction: psi-scan (North et al., 1968) | k = −10→0 |
Tmin = 0.091, Tmax = 0.199 | l = −21→21 |
3958 measured reflections | 3 standard reflections every 120 min |
2017 independent reflections | intensity decay: 1.0% |
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)] = 0.055 | H-atom parameters constrained |
wR(F2) = 0.156 | w = 1/[σ2(Fo2) + (0.1016P)2 + 1.9543P] where P = (Fo2 + 2Fc2)/3 |
S = 1.04 | (Δ/σ)max = 0.001 |
2017 reflections | Δρmax = 0.61 e Å−3 |
137 parameters | Δρmin = −0.57 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0026 (3) |
C8H4Cl5NO | V = 2260.1 (8) Å3 |
Mr = 307.37 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 14.306 (2) Å | µ = 11.47 mm−1 |
b = 8.625 (2) Å | T = 299 K |
c = 18.317 (4) Å | 0.40 × 0.25 × 0.25 mm |
Enraf-Nonius CAD-4 diffractometer | 1780 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.034 |
Tmin = 0.091, Tmax = 0.199 | 3 standard reflections every 120 min |
3958 measured reflections | intensity decay: 1.0% |
2017 independent reflections |
R[F2 > 2σ(F2)] = 0.055 | 0 restraints |
wR(F2) = 0.156 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.61 e Å−3 |
2017 reflections | Δρmin = −0.57 e Å−3 |
137 parameters |
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 | ||
C4 | 0.8787 (2) | 0.4639 (4) | 0.21953 (18) | 0.0379 (7) | |
C5 | 0.7991 (2) | 0.4206 (4) | 0.27435 (17) | 0.0363 (7) | |
C8 | 0.7702 (2) | 0.2521 (4) | 0.38080 (17) | 0.0376 (7) | |
C9 | 0.8146 (2) | 0.1638 (4) | 0.43387 (17) | 0.0411 (7) | |
C10 | 0.7655 (3) | 0.0913 (4) | 0.48874 (18) | 0.0455 (8) | |
H10 | 0.7961 | 0.0307 | 0.5233 | 0.055* | |
C11 | 0.6702 (3) | 0.1103 (4) | 0.49132 (17) | 0.0441 (8) | |
C12 | 0.6239 (2) | 0.1961 (5) | 0.4390 (2) | 0.0473 (8) | |
H12 | 0.5592 | 0.2064 | 0.4410 | 0.057* | |
C13 | 0.6742 (2) | 0.2669 (4) | 0.38368 (18) | 0.0444 (8) | |
H13 | 0.6431 | 0.3245 | 0.3483 | 0.053* | |
N7 | 0.8264 (2) | 0.3205 (4) | 0.32653 (15) | 0.0432 (7) | |
H7N | 0.8846 | 0.2955 | 0.3267 | 0.052* | |
O6 | 0.72271 (18) | 0.4723 (3) | 0.26554 (15) | 0.0549 (7) | |
Cl1 | 0.85165 (7) | 0.63777 (11) | 0.17582 (6) | 0.0615 (4) | |
Cl2 | 0.88387 (7) | 0.31299 (12) | 0.15463 (5) | 0.0555 (3) | |
Cl3 | 0.98924 (6) | 0.48027 (15) | 0.26205 (5) | 0.0634 (4) | |
Cl14 | 0.93496 (6) | 0.13974 (14) | 0.43103 (6) | 0.0628 (4) | |
Cl15 | 0.60865 (8) | 0.02480 (14) | 0.56195 (5) | 0.0654 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C4 | 0.0413 (16) | 0.0405 (17) | 0.0317 (15) | 0.0016 (13) | 0.0019 (12) | 0.0003 (14) |
C5 | 0.0360 (15) | 0.0407 (15) | 0.0323 (15) | −0.0028 (13) | 0.0027 (12) | −0.0064 (13) |
C8 | 0.0427 (16) | 0.0431 (16) | 0.0269 (14) | −0.0022 (13) | 0.0021 (12) | −0.0029 (13) |
C9 | 0.0388 (16) | 0.0503 (18) | 0.0343 (16) | −0.0006 (14) | −0.0053 (12) | −0.0033 (14) |
C10 | 0.056 (2) | 0.0504 (18) | 0.0299 (16) | −0.0004 (16) | −0.0030 (14) | 0.0018 (14) |
C11 | 0.0546 (19) | 0.0504 (18) | 0.0273 (15) | −0.0053 (15) | 0.0073 (13) | −0.0009 (14) |
C12 | 0.0396 (16) | 0.055 (2) | 0.047 (2) | −0.0009 (15) | 0.0063 (14) | 0.0037 (17) |
C13 | 0.0449 (16) | 0.0541 (19) | 0.0341 (15) | 0.0038 (15) | 0.0027 (13) | 0.0058 (15) |
N7 | 0.0348 (13) | 0.0548 (17) | 0.0400 (15) | 0.0028 (12) | 0.0055 (11) | 0.0101 (13) |
O6 | 0.0440 (14) | 0.0669 (17) | 0.0539 (16) | 0.0076 (12) | 0.0069 (11) | 0.0172 (13) |
Cl1 | 0.0623 (6) | 0.0503 (6) | 0.0718 (7) | 0.0066 (4) | 0.0147 (5) | 0.0210 (5) |
Cl2 | 0.0710 (6) | 0.0582 (6) | 0.0373 (5) | 0.0051 (4) | 0.0075 (4) | −0.0117 (4) |
Cl3 | 0.0425 (5) | 0.0980 (8) | 0.0499 (6) | −0.0173 (5) | −0.0058 (4) | 0.0079 (5) |
Cl14 | 0.0406 (5) | 0.0869 (8) | 0.0610 (6) | 0.0034 (4) | −0.0072 (4) | 0.0154 (5) |
Cl15 | 0.0772 (7) | 0.0718 (7) | 0.0473 (6) | −0.0046 (5) | 0.0198 (4) | 0.0156 (5) |
C4—C5 | 1.564 (4) | C9—Cl14 | 1.735 (3) |
C4—Cl1 | 1.744 (3) | C10—C11 | 1.374 (5) |
C4—Cl2 | 1.764 (3) | C10—H10 | 0.9300 |
C4—Cl3 | 1.769 (3) | C11—C12 | 1.379 (5) |
C5—O6 | 1.190 (4) | C11—Cl15 | 1.730 (3) |
C5—N7 | 1.347 (4) | C12—C13 | 1.385 (5) |
C8—C13 | 1.381 (5) | C12—H12 | 0.9300 |
C8—C9 | 1.389 (5) | C13—H13 | 0.9300 |
C8—N7 | 1.408 (4) | N7—H7N | 0.8600 |
C9—C10 | 1.377 (5) | ||
C5—C4—Cl1 | 109.8 (2) | C11—C10—C9 | 118.5 (3) |
C5—C4—Cl2 | 106.7 (2) | C11—C10—H10 | 120.7 |
Cl1—C4—Cl2 | 109.54 (18) | C9—C10—H10 | 120.7 |
C5—C4—Cl3 | 112.8 (2) | C10—C11—C12 | 121.1 (3) |
Cl1—C4—Cl3 | 109.38 (18) | C10—C11—Cl15 | 118.7 (3) |
Cl2—C4—Cl3 | 108.55 (18) | C12—C11—Cl15 | 120.2 (3) |
O6—C5—N7 | 127.1 (3) | C11—C12—C13 | 119.7 (3) |
O6—C5—C4 | 119.5 (3) | C11—C12—H12 | 120.1 |
N7—C5—C4 | 113.4 (3) | C13—C12—H12 | 120.1 |
C13—C8—C9 | 118.6 (3) | C8—C13—C12 | 120.3 (3) |
C13—C8—N7 | 123.8 (3) | C8—C13—H13 | 119.9 |
C9—C8—N7 | 117.6 (3) | C12—C13—H13 | 119.9 |
C10—C9—C8 | 121.8 (3) | C5—N7—C8 | 127.1 (3) |
C10—C9—Cl14 | 118.3 (3) | C5—N7—H7N | 116.4 |
C8—C9—Cl14 | 119.9 (3) | C8—N7—H7N | 116.4 |
Cl1—C4—C5—O6 | 23.0 (4) | C9—C10—C11—C12 | 2.0 (6) |
Cl2—C4—C5—O6 | −95.6 (3) | C9—C10—C11—Cl15 | −177.8 (3) |
Cl3—C4—C5—O6 | 145.3 (3) | C10—C11—C12—C13 | −1.2 (6) |
Cl1—C4—C5—N7 | −159.3 (2) | Cl15—C11—C12—C13 | 178.6 (3) |
Cl2—C4—C5—N7 | 82.1 (3) | C9—C8—C13—C12 | 0.7 (5) |
Cl3—C4—C5—N7 | −37.0 (3) | N7—C8—C13—C12 | −179.9 (3) |
C13—C8—C9—C10 | 0.0 (5) | C11—C12—C13—C8 | −0.2 (6) |
N7—C8—C9—C10 | −179.4 (3) | O6—C5—N7—C8 | 1.7 (6) |
C13—C8—C9—Cl14 | 178.8 (3) | C4—C5—N7—C8 | −175.7 (3) |
N7—C8—C9—Cl14 | −0.6 (4) | C13—C8—N7—C5 | 7.0 (5) |
C8—C9—C10—C11 | −1.4 (5) | C9—C8—N7—C5 | −173.7 (3) |
Cl14—C9—C10—C11 | 179.8 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···Cl3 | 0.86 | 2.49 | 2.953 (3) | 115 |
N7—H7N···Cl14 | 0.86 | 2.44 | 2.916 (3) | 115 |
Experimental details
Crystal data | |
Chemical formula | C8H4Cl5NO |
Mr | 307.37 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 299 |
a, b, c (Å) | 14.306 (2), 8.625 (2), 18.317 (4) |
V (Å3) | 2260.1 (8) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 11.47 |
Crystal size (mm) | 0.40 × 0.25 × 0.25 |
Data collection | |
Diffractometer | Enraf-Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.091, 0.199 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 3958, 2017, 1780 |
Rint | 0.034 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.156, 1.04 |
No. of reflections | 2017 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.61, −0.57 |
Computer programs: CAD-4-PC (Enraf-Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···Cl3 | 0.86 | 2.49 | 2.953 (3) | 114.8 |
N7—H7N···Cl14 | 0.86 | 2.44 | 2.916 (3) | 115.2 |
Subscribe to Acta Crystallographica Section E: Crystallographic Communications
The full text of this article is available to subscribers to the journal.
- Information on subscribing
- Sample issue
- If you have already subscribed, you may need to register
In the present work, the structure of N-(2,4-dichlorophenyl)-2,2,2- trichloroacetamide has been determined as part of a study in the direction of systematization of the crystal structures of N-aromatic amides (Gowda et al., 2000; 2007a, b, c, d). The conformation of the N—H bond is syn to the ortho-chloro substituent (Fig. 1), similar to that observed in N-(2-chlorophenyl)-acetamide (Gowda et al., 2007c), N-(2,4-DiChlorophenyl)-acetamide (Gowda et al., 2007d), N-(2-chlorophenyl)-2,2,2- trichloroacetamide (Gowda et al., 2000) and N-(2-chlorophenyl)- 2,2,2-trimethylacetamide (Gowda et al., 2007b). The geometric parameters are similar to those in other acetanilides (Gowda et al., 2000; 2007a, b, c, d). The amide H is involved in two intra-molecular hydrogen bonding with the ortho ring Cl atom and one of the Cl atoms of the CCl3 group (Fig. 1) (Fig. 2 & Table 1).