Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807057054/bt2597sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807057054/bt2597Isup2.hkl |
CCDC reference: 672936
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.046
- wR factor = 0.129
- Data-to-parameter ratio = 15.4
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C8 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 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 0 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check
For related literature, see: Gowda et al. (2001, 2006, 2007a,b); Shilpa & Gowda (2007).
The title compound was prepared according to the literature method (Shilpa and Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared and NMR spectra (Shilpa and Gowda, 2007). 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 = 0.93–0.98 Å. Uiso(H) values were set equal to 1.2 Ueq of the parent atom.
Data collection: CAD-4-PC Software (Enraf–Nonius, 1996); cell refinement: CAD-4-PC Software (Enraf–Nonius, 1996); 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 (Sheldrick, 1997).
C8H5Cl4NO | F(000) = 544 |
Mr = 272.93 | Dx = 1.663 Mg m−3 |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2yn | Cell parameters from 25 reflections |
a = 4.674 (1) Å | θ = 5.8–20.3° |
b = 11.804 (2) Å | µ = 9.60 mm−1 |
c = 19.833 (3) Å | T = 299 K |
β = 95.05 (1)° | Needle, colourless |
V = 1090.0 (3) Å3 | 0.60 × 0.08 × 0.03 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1421 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 66.9°, θmin = 4.4° |
ω/2θ scans | h = 0→5 |
Absorption correction: ψ scan (North et al., 1968) | k = −14→2 |
Tmin = 0.322, Tmax = 0.750 | l = −23→23 |
2435 measured reflections | 3 standard reflections every 120 min |
1950 independent reflections | intensity decay: 1.0% |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.046 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0721P)2 + 0.5313P] where P = (Fo2 + 2Fc2)/3 |
1950 reflections | (Δ/σ)max < 0.001 |
127 parameters | Δρmax = 0.31 e Å−3 |
0 restraints | Δρmin = −0.44 e Å−3 |
C8H5Cl4NO | V = 1090.0 (3) Å3 |
Mr = 272.93 | Z = 4 |
Monoclinic, P21/n | Cu Kα radiation |
a = 4.674 (1) Å | µ = 9.60 mm−1 |
b = 11.804 (2) Å | T = 299 K |
c = 19.833 (3) Å | 0.60 × 0.08 × 0.03 mm |
β = 95.05 (1)° |
Enraf–Nonius CAD-4 diffractometer | 1421 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.025 |
Tmin = 0.322, Tmax = 0.750 | 3 standard reflections every 120 min |
2435 measured reflections | intensity decay: 1.0% |
1950 independent reflections |
R[F2 > 2σ(F2)] = 0.046 | 0 restraints |
wR(F2) = 0.129 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.31 e Å−3 |
1950 reflections | Δρmin = −0.44 e Å−3 |
127 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 | ||
Cl1 | 0.8086 (2) | −0.02347 (8) | 0.21645 (5) | 0.0564 (3) | |
Cl2 | 0.6830 (3) | −0.03704 (9) | 0.36898 (5) | 0.0763 (4) | |
Cl3 | 0.4053 (3) | 0.33369 (10) | −0.00199 (6) | 0.0782 (4) | |
Cl4 | 0.2454 (3) | 0.10696 (11) | −0.04307 (5) | 0.0761 (4) | |
O1 | 0.0589 (5) | 0.1713 (3) | 0.09146 (13) | 0.0714 (9) | |
N1 | 0.5159 (5) | 0.1646 (2) | 0.13964 (13) | 0.0395 (6) | |
H1N | 0.6933 | 0.1633 | 0.1312 | 0.047* | |
C1 | 0.4524 (6) | 0.1571 (3) | 0.20853 (15) | 0.0365 (7) | |
C2 | 0.5814 (7) | 0.0733 (3) | 0.24928 (15) | 0.0378 (7) | |
C3 | 0.5257 (8) | 0.0668 (3) | 0.31709 (17) | 0.0474 (8) | |
C4 | 0.3431 (9) | 0.1429 (4) | 0.34292 (17) | 0.0572 (10) | |
H4 | 0.3052 | 0.1382 | 0.3881 | 0.069* | |
C5 | 0.2162 (9) | 0.2260 (4) | 0.30237 (19) | 0.0587 (10) | |
H5 | 0.0922 | 0.2773 | 0.3203 | 0.070* | |
C6 | 0.2705 (8) | 0.2346 (3) | 0.23480 (18) | 0.0478 (8) | |
H6 | 0.1856 | 0.2918 | 0.2076 | 0.057* | |
C7 | 0.3169 (7) | 0.1735 (3) | 0.08749 (16) | 0.0414 (7) | |
C8 | 0.4369 (7) | 0.1891 (3) | 0.01915 (16) | 0.0454 (8) | |
H8 | 0.6398 | 0.1671 | 0.0227 | 0.054* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0591 (6) | 0.0535 (5) | 0.0558 (5) | 0.0144 (4) | −0.0003 (4) | −0.0054 (4) |
Cl2 | 0.1161 (10) | 0.0611 (6) | 0.0478 (5) | −0.0047 (6) | −0.0142 (6) | 0.0150 (5) |
Cl3 | 0.1027 (9) | 0.0732 (7) | 0.0587 (6) | −0.0169 (6) | 0.0076 (6) | 0.0143 (5) |
Cl4 | 0.0814 (8) | 0.0907 (8) | 0.0537 (5) | −0.0051 (6) | −0.0080 (5) | −0.0211 (5) |
O1 | 0.0236 (12) | 0.143 (3) | 0.0475 (14) | −0.0033 (14) | 0.0037 (10) | 0.0094 (17) |
N1 | 0.0253 (12) | 0.0599 (17) | 0.0337 (13) | 0.0029 (12) | 0.0044 (10) | 0.0049 (12) |
C1 | 0.0301 (15) | 0.0456 (17) | 0.0337 (15) | −0.0059 (13) | 0.0026 (12) | 0.0014 (13) |
C2 | 0.0359 (16) | 0.0404 (16) | 0.0366 (16) | −0.0065 (13) | −0.0003 (13) | −0.0046 (13) |
C3 | 0.057 (2) | 0.0499 (19) | 0.0335 (15) | −0.0115 (17) | −0.0036 (15) | 0.0044 (15) |
C4 | 0.066 (2) | 0.074 (3) | 0.0332 (17) | −0.008 (2) | 0.0136 (17) | −0.0058 (17) |
C5 | 0.056 (2) | 0.073 (3) | 0.049 (2) | 0.007 (2) | 0.0141 (17) | −0.014 (2) |
C6 | 0.0415 (18) | 0.055 (2) | 0.0468 (18) | 0.0075 (16) | 0.0043 (15) | 0.0019 (16) |
C7 | 0.0292 (15) | 0.059 (2) | 0.0363 (16) | 0.0010 (14) | 0.0048 (12) | 0.0036 (15) |
C8 | 0.0332 (16) | 0.069 (2) | 0.0340 (16) | 0.0006 (15) | 0.0031 (13) | 0.0016 (16) |
Cl1—C2 | 1.726 (3) | C2—C3 | 1.394 (4) |
Cl2—C3 | 1.723 (4) | C3—C4 | 1.369 (5) |
Cl3—C8 | 1.761 (4) | C4—C5 | 1.370 (6) |
Cl4—C8 | 1.752 (4) | C4—H4 | 0.9300 |
O1—C7 | 1.216 (4) | C5—C6 | 1.389 (5) |
N1—C7 | 1.333 (4) | C5—H5 | 0.9300 |
N1—C1 | 1.426 (4) | C6—H6 | 0.9300 |
N1—H1N | 0.8600 | C7—C8 | 1.523 (4) |
C1—C2 | 1.382 (4) | C8—H8 | 0.9800 |
C1—C6 | 1.382 (5) | ||
C7—N1—C1 | 123.9 (3) | C4—C5—C6 | 120.8 (4) |
C7—N1—H1N | 118.0 | C4—C5—H5 | 119.6 |
C1—N1—H1N | 118.0 | C6—C5—H5 | 119.6 |
C2—C1—C6 | 120.3 (3) | C1—C6—C5 | 119.1 (3) |
C2—C1—N1 | 119.2 (3) | C1—C6—H6 | 120.5 |
C6—C1—N1 | 120.5 (3) | C5—C6—H6 | 120.5 |
C1—C2—C3 | 119.6 (3) | O1—C7—N1 | 125.2 (3) |
C1—C2—Cl1 | 120.3 (2) | O1—C7—C8 | 120.4 (3) |
C3—C2—Cl1 | 120.1 (3) | N1—C7—C8 | 114.4 (3) |
C4—C3—C2 | 120.0 (3) | C7—C8—Cl4 | 110.8 (2) |
C4—C3—Cl2 | 119.4 (3) | C7—C8—Cl3 | 107.4 (2) |
C2—C3—Cl2 | 120.6 (3) | Cl4—C8—Cl3 | 109.98 (19) |
C3—C4—C5 | 120.1 (3) | C7—C8—H8 | 109.5 |
C3—C4—H4 | 119.9 | Cl4—C8—H8 | 109.5 |
C5—C4—H4 | 119.9 | Cl3—C8—H8 | 109.5 |
C7—N1—C1—C2 | 131.1 (3) | Cl2—C3—C4—C5 | 180.0 (3) |
C7—N1—C1—C6 | −50.7 (5) | C3—C4—C5—C6 | −0.1 (6) |
C6—C1—C2—C3 | 0.4 (5) | C2—C1—C6—C5 | −0.9 (5) |
N1—C1—C2—C3 | 178.6 (3) | N1—C1—C6—C5 | −179.1 (3) |
C6—C1—C2—Cl1 | −180.0 (3) | C4—C5—C6—C1 | 0.8 (6) |
N1—C1—C2—Cl1 | −1.8 (4) | C1—N1—C7—O1 | −3.4 (6) |
C1—C2—C3—C4 | 0.3 (5) | C1—N1—C7—C8 | 175.7 (3) |
Cl1—C2—C3—C4 | −179.3 (3) | O1—C7—C8—Cl4 | −42.7 (4) |
C1—C2—C3—Cl2 | 179.9 (2) | N1—C7—C8—Cl4 | 138.2 (3) |
Cl1—C2—C3—Cl2 | 0.3 (4) | O1—C7—C8—Cl3 | 77.5 (4) |
C2—C3—C4—C5 | −0.4 (6) | N1—C7—C8—Cl3 | −101.6 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 1.95 | 2.790 (3) | 167 |
Symmetry code: (i) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C8H5Cl4NO |
Mr | 272.93 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 299 |
a, b, c (Å) | 4.674 (1), 11.804 (2), 19.833 (3) |
β (°) | 95.05 (1) |
V (Å3) | 1090.0 (3) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 9.60 |
Crystal size (mm) | 0.60 × 0.08 × 0.03 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 diffractometer |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.322, 0.750 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2435, 1950, 1421 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.046, 0.129, 1.05 |
No. of reflections | 1950 |
No. of parameters | 127 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.31, −0.44 |
Computer programs: CAD-4-PC Software (Enraf–Nonius, 1996), REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···O1i | 0.86 | 1.95 | 2.790 (3) | 166.7 |
Symmetry code: (i) x+1, y, z. |
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In the present work, the structure of N-(2,3-dichlorophenyl)-2,2- dichloroacetamide (23DCPDCA) has been determined to study the substituent effects on the structures of N-aromatic amides (Gowda et al., 2001, 2006; 2007a, b). The conformation of the N—H bond in 23DCPDCA is syn to both the 2-chloro and 3-chloro substituent (Fig. 1), similar to that of 2-chloro substituent in N-(2-chlorophenyl)-2,2- dichloroacetamide (2CPDCA)(Gowda et al., 2001), 3-chloro substituent in N-(3,4-dichlorophenyl)-2,2-dichloroacetamide (34DCPDCA) (Gowda et al., 2007b), and 2- and 3-chloro substituents in N-(2,3-dichlorophenyl)-acetamide (23DCPA)(Gowda et al., 2007a), but in contrast to the anti conformation observed with respect to the 3-chloro substituent in the N-(3-chlorophenyl)- 2,2-dichloroacetamide (3CPDCA)(Gowda et al., 2006)·The bond parameters in 23DCPDCA are similar to those in N-(phenyl)-2,2-dichloroacetamide, 2CPDCA, 3CPDCA, 34DCPDCA, 23DCPA and other acetanilides (Gowda et al., 2001, 2006; 2007a, b). The molecules in 23DCPDCA are linked into chains through N—H···O hydrogen bonding (Table 1 and Fig.2).