Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680703930X/wn2185sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680703930X/wn2185Isup2.hkl |
CCDC reference: 660275
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.061
- wR factor = 0.176
- Data-to-parameter ratio = 15.9
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? PLAT057_ALERT_3_A Correction for Absorption Required RT(exp) ... 1.66
Alert level C PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C4 PLAT242_ALERT_2_C Check Low Ueq as Compared to Neighbors for C12 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
2 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 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 2 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
The title compound was prepared according to a literature method (Shilpa & 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 & Gowda, 2007). Single crystals of the title compound were obtained by slow evaporation of an ethanolic solution (2 g in about 30 ml e thanol) and used for the X-ray diffraction study at room temperature.
All H atoms were positioned geometrically and refined as riding with C—H = 0.93–0.96 Å and N—H = 0.86 Å; Uiso(H) = 1.2Ueq(C,N).
As part of a study of the effect of ring and side chain substitutions on the solid state structures of aromatic amides (Gowda et al., 2007a,b), the crystal structure of N-(2,3-dichlorophenyl)-2,2,2-trimethylacetamide (23DCPTMA) has been determined. The conformation of the N—H bond in 23DCPTMA is syn to both the 2-chloro and 3-chloro groups (Fig. 1), similar to that in N-(2,3-dichlorophenyl)-acetamide (23DCPA)(Gowda et al., 2007b), but in contrast to the anti conformation with respect to the 3-chloro substituent in N-(3-chlorophenyl)- 2,2,2-trimethylacetamide (3CPTMA) (Gowda et al., 2007a). Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2).
For related literature, see: Gowda et al. (2007a,b); Shilpa & Gowda (2007).
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.
C11H13Cl2NO | F(000) = 512 |
Mr = 246.12 | Dx = 1.333 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ybc | Cell parameters from 24 reflections |
a = 11.206 (3) Å | θ = 5.7–19.5° |
b = 11.139 (3) Å | µ = 4.55 mm−1 |
c = 10.075 (2) Å | T = 299 K |
β = 102.70 (3)° | Rod, colourless |
V = 1226.8 (5) Å3 | 0.60 × 0.30 × 0.20 mm |
Z = 4 |
Enraf–Nonius CAD-4 diffractometer | 1680 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 66.9°, θmin = 4.0° |
ω/2θ scans | h = −13→13 |
Absorption correction: ψ scan (North et al., 1968) | k = −3→13 |
Tmin = 0.264, Tmax = 0.402 | l = 0→12 |
2957 measured reflections | 3 standard reflections every 120 min |
2174 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)] = 0.061 | H-atom parameters constrained |
wR(F2) = 0.176 | w = 1/[σ2(Fo2) + (0.1081P)2 + 0.276P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
2174 reflections | Δρmax = 0.30 e Å−3 |
137 parameters | Δρmin = −0.50 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: 0.0058 (11) |
C11H13Cl2NO | V = 1226.8 (5) Å3 |
Mr = 246.12 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 11.206 (3) Å | µ = 4.55 mm−1 |
b = 11.139 (3) Å | T = 299 K |
c = 10.075 (2) Å | 0.60 × 0.30 × 0.20 mm |
β = 102.70 (3)° |
Enraf–Nonius CAD-4 diffractometer | 1680 reflections with I > 2σ(I) |
Absorption correction: ψ scan (North et al., 1968) | Rint = 0.029 |
Tmin = 0.264, Tmax = 0.402 | 3 standard reflections every 120 min |
2957 measured reflections | intensity decay: 1.0% |
2174 independent reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.176 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.30 e Å−3 |
2174 reflections | Δρmin = −0.50 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 | ||
Cl14 | 1.22112 (9) | 0.32462 (14) | 0.47441 (15) | 0.1266 (6) | |
Cl15 | 0.99510 (9) | 0.17412 (8) | 0.51766 (9) | 0.0841 (4) | |
O6 | 0.7204 (2) | 0.2107 (2) | 0.15772 (18) | 0.0698 (6) | |
N7 | 0.7557 (2) | 0.2709 (2) | 0.3746 (2) | 0.0570 (6) | |
H7N | 0.7322 | 0.2703 | 0.4503 | 0.068* | |
C1 | 0.6547 (4) | 0.0286 (4) | 0.4031 (4) | 0.1053 (14) | |
H1A | 0.5933 | −0.0254 | 0.4209 | 0.126* | |
H1B | 0.6931 | 0.0687 | 0.4858 | 0.126* | |
H1C | 0.7151 | −0.0159 | 0.3691 | 0.126* | |
C2 | 0.5355 (3) | 0.0561 (3) | 0.1681 (3) | 0.0802 (10) | |
H2A | 0.5961 | 0.0112 | 0.1351 | 0.096* | |
H2B | 0.4982 | 0.1136 | 0.1007 | 0.096* | |
H2C | 0.4741 | 0.0023 | 0.1864 | 0.096* | |
C3 | 0.5000 (4) | 0.1915 (4) | 0.3513 (5) | 0.0960 (13) | |
H3A | 0.4383 | 0.1376 | 0.3686 | 0.115* | |
H3B | 0.4630 | 0.2499 | 0.2848 | 0.115* | |
H3C | 0.5382 | 0.2315 | 0.4341 | 0.115* | |
C4 | 0.5956 (2) | 0.1210 (2) | 0.2978 (3) | 0.0525 (6) | |
C5 | 0.6947 (2) | 0.2046 (2) | 0.2697 (2) | 0.0466 (6) | |
C8 | 0.8579 (2) | 0.3419 (2) | 0.3625 (2) | 0.0537 (7) | |
C9 | 0.8410 (3) | 0.4482 (3) | 0.2922 (3) | 0.0674 (8) | |
H9 | 0.7623 | 0.4743 | 0.2531 | 0.081* | |
C10 | 0.9402 (4) | 0.5161 (3) | 0.2796 (3) | 0.0816 (10) | |
H10 | 0.9282 | 0.5883 | 0.2322 | 0.098* | |
C11 | 1.0561 (4) | 0.4787 (3) | 0.3358 (4) | 0.0854 (11) | |
H11 | 1.1226 | 0.5252 | 0.3264 | 0.102* | |
C12 | 1.0746 (3) | 0.3726 (3) | 0.4063 (3) | 0.0735 (9) | |
C13 | 0.9751 (3) | 0.3034 (3) | 0.4223 (3) | 0.0586 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl14 | 0.0569 (5) | 0.1743 (13) | 0.1510 (12) | −0.0080 (6) | 0.0279 (6) | −0.0386 (9) |
Cl15 | 0.0899 (6) | 0.0854 (6) | 0.0783 (6) | 0.0121 (4) | 0.0208 (4) | 0.0081 (4) |
O6 | 0.0851 (14) | 0.0934 (15) | 0.0356 (9) | −0.0323 (12) | 0.0234 (9) | −0.0110 (9) |
N7 | 0.0609 (12) | 0.0793 (15) | 0.0333 (10) | −0.0228 (11) | 0.0158 (9) | −0.0086 (9) |
C1 | 0.109 (3) | 0.097 (3) | 0.098 (3) | −0.031 (2) | 0.000 (2) | 0.045 (2) |
C2 | 0.079 (2) | 0.094 (2) | 0.0668 (19) | −0.0310 (18) | 0.0145 (16) | −0.0173 (17) |
C3 | 0.078 (2) | 0.095 (3) | 0.131 (3) | −0.0221 (19) | 0.059 (2) | −0.034 (2) |
C4 | 0.0542 (13) | 0.0578 (15) | 0.0476 (13) | −0.0097 (11) | 0.0155 (11) | −0.0023 (11) |
C5 | 0.0488 (12) | 0.0558 (14) | 0.0361 (12) | −0.0020 (10) | 0.0114 (9) | −0.0021 (9) |
C8 | 0.0606 (15) | 0.0651 (16) | 0.0375 (12) | −0.0170 (12) | 0.0157 (11) | −0.0112 (11) |
C9 | 0.082 (2) | 0.0704 (18) | 0.0499 (14) | −0.0113 (15) | 0.0140 (13) | −0.0026 (13) |
C10 | 0.117 (3) | 0.071 (2) | 0.0636 (18) | −0.029 (2) | 0.0357 (19) | −0.0050 (15) |
C11 | 0.095 (3) | 0.091 (3) | 0.084 (2) | −0.046 (2) | 0.049 (2) | −0.0300 (19) |
C12 | 0.0599 (16) | 0.096 (2) | 0.0704 (19) | −0.0200 (16) | 0.0268 (14) | −0.0292 (17) |
C13 | 0.0625 (16) | 0.0688 (17) | 0.0480 (14) | −0.0087 (12) | 0.0201 (12) | −0.0150 (12) |
Cl14—C12 | 1.720 (4) | C3—C4 | 1.519 (4) |
Cl15—C13 | 1.719 (3) | C3—H3A | 0.9600 |
O6—C5 | 1.226 (3) | C3—H3B | 0.9600 |
N7—C5 | 1.346 (3) | C3—H3C | 0.9600 |
N7—C8 | 1.419 (3) | C4—C5 | 1.523 (3) |
N7—H7N | 0.8600 | C8—C9 | 1.371 (4) |
C1—C4 | 1.522 (4) | C8—C13 | 1.387 (4) |
C1—H1A | 0.9600 | C9—C10 | 1.374 (5) |
C1—H1B | 0.9600 | C9—H9 | 0.9300 |
C1—H1C | 0.9600 | C10—C11 | 1.362 (6) |
C2—C4 | 1.516 (4) | C10—H10 | 0.9300 |
C2—H2A | 0.9600 | C11—C12 | 1.371 (5) |
C2—H2B | 0.9600 | C11—H11 | 0.9300 |
C2—H2C | 0.9600 | C12—C13 | 1.393 (4) |
C5—N7—C8 | 121.2 (2) | C2—C4—C5 | 109.6 (2) |
C5—N7—H7N | 119.4 | C3—C4—C5 | 110.5 (2) |
C8—N7—H7N | 119.4 | C1—C4—C5 | 108.7 (2) |
C4—C1—H1A | 109.5 | O6—C5—N7 | 120.6 (2) |
C4—C1—H1B | 109.5 | O6—C5—C4 | 122.3 (2) |
H1A—C1—H1B | 109.5 | N7—C5—C4 | 117.0 (2) |
C4—C1—H1C | 109.5 | C9—C8—C13 | 120.1 (3) |
H1A—C1—H1C | 109.5 | C9—C8—N7 | 120.2 (3) |
H1B—C1—H1C | 109.5 | C13—C8—N7 | 119.7 (2) |
C4—C2—H2A | 109.5 | C8—C9—C10 | 120.0 (3) |
C4—C2—H2B | 109.5 | C8—C9—H9 | 120.0 |
H2A—C2—H2B | 109.5 | C10—C9—H9 | 120.0 |
C4—C2—H2C | 109.5 | C11—C10—C9 | 120.7 (4) |
H2A—C2—H2C | 109.5 | C11—C10—H10 | 119.7 |
H2B—C2—H2C | 109.5 | C9—C10—H10 | 119.7 |
C4—C3—H3A | 109.5 | C10—C11—C12 | 120.0 (3) |
C4—C3—H3B | 109.5 | C10—C11—H11 | 120.0 |
H3A—C3—H3B | 109.5 | C12—C11—H11 | 120.0 |
C4—C3—H3C | 109.5 | C11—C12—C13 | 120.2 (3) |
H3A—C3—H3C | 109.5 | C11—C12—Cl14 | 119.8 (3) |
H3B—C3—H3C | 109.5 | C13—C12—Cl14 | 120.0 (3) |
C2—C4—C3 | 109.8 (3) | C8—C13—C12 | 119.0 (3) |
C2—C4—C1 | 108.7 (3) | C8—C13—Cl15 | 119.8 (2) |
C3—C4—C1 | 109.6 (3) | C12—C13—Cl15 | 121.3 (3) |
C8—N7—C5—O6 | −5.4 (4) | C8—C9—C10—C11 | 0.3 (5) |
C8—N7—C5—C4 | 173.3 (2) | C9—C10—C11—C12 | −0.3 (5) |
C2—C4—C5—O6 | −2.5 (4) | C10—C11—C12—C13 | −0.8 (5) |
C3—C4—C5—O6 | −123.5 (3) | C10—C11—C12—Cl14 | 178.8 (3) |
C1—C4—C5—O6 | 116.2 (3) | C9—C8—C13—C12 | −1.8 (4) |
C2—C4—C5—N7 | 178.8 (3) | N7—C8—C13—C12 | 178.3 (2) |
C3—C4—C5—N7 | 57.8 (4) | C9—C8—C13—Cl15 | 176.6 (2) |
C1—C4—C5—N7 | −62.5 (4) | N7—C8—C13—Cl15 | −3.3 (3) |
C5—N7—C8—C9 | 75.9 (4) | C11—C12—C13—C8 | 1.9 (4) |
C5—N7—C8—C13 | −104.3 (3) | Cl14—C12—C13—C8 | −177.8 (2) |
C13—C8—C9—C10 | 0.8 (4) | C11—C12—C13—Cl15 | −176.5 (2) |
N7—C8—C9—C10 | −179.4 (3) | Cl14—C12—C13—Cl15 | 3.8 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N7—H7N···O6i | 0.86 | 2.13 | 2.972 (3) | 165 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C11H13Cl2NO |
Mr | 246.12 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 299 |
a, b, c (Å) | 11.206 (3), 11.139 (3), 10.075 (2) |
β (°) | 102.70 (3) |
V (Å3) | 1226.8 (5) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 4.55 |
Crystal size (mm) | 0.60 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | ψ scan (North et al., 1968) |
Tmin, Tmax | 0.264, 0.402 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 2957, 2174, 1680 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.176, 1.06 |
No. of reflections | 2174 |
No. of parameters | 137 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.30, −0.50 |
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 |
N7—H7N···O6i | 0.86 | 2.13 | 2.972 (3) | 164.9 |
Symmetry code: (i) x, −y+1/2, z+1/2. |
As part of a study of the effect of ring and side chain substitutions on the solid state structures of aromatic amides (Gowda et al., 2007a,b), the crystal structure of N-(2,3-dichlorophenyl)-2,2,2-trimethylacetamide (23DCPTMA) has been determined. The conformation of the N—H bond in 23DCPTMA is syn to both the 2-chloro and 3-chloro groups (Fig. 1), similar to that in N-(2,3-dichlorophenyl)-acetamide (23DCPA)(Gowda et al., 2007b), but in contrast to the anti conformation with respect to the 3-chloro substituent in N-(3-chlorophenyl)- 2,2,2-trimethylacetamide (3CPTMA) (Gowda et al., 2007a). Intermolecular N—H···O hydrogen bonds (Table 1) link the molecules into chains (Fig. 2).