organic compounds
2-Chloro-N-(2,6-dimethylphenyl)acetamide
aDepartment of Chemistry, Mangalore University, Mangalagangotri-574 199, Mangalore, India, and bInstitute of Materials Science, Darmstadt University of Technology, Petersenstrasse 23, D-64287, Darmstadt, Germany
*Correspondence e-mail: gowdabt@yahoo.com
The 10H12ClNO, is closely related to those of side-chain-unsubstituted N-(2,6-dimethylphenyl)acetamide and side-chain-substituted 2,2,2-trichloro-N-(2,6-dimethylphenyl)acetamide and N-(2,6-dimethylphenyl)-2,2,2-trimethylacetamide, with slightly different bond parameters. The molecules in 26DMPCA are linked into chains through N—H⋯O hydrogen bonding.
of the title compound (26DMPCA), CRelated literature
For related literature, see: Gowda et al. (2004, 2007a,b,c,d,e,f); Gowda, Kozisek et al. (2007); Gowda, Svoboda & Fuess (2007).
Experimental
Crystal data
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Refinement
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Data collection: STADI4 (Stoe & Cie, 1987); cell STADI4; 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.
Supporting information
https://doi.org/10.1107/S160053680706624X/lw2052sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S160053680706624X/lw2052Isup2.hkl
The title compound was prepared according to the literature method (Gowda et al., 2004). The purity of the compound was checked by determining its melting point. The compound was further characterized by recording its infrared and NMR spectra (Gowda et al., 2004). Single crystals of the title compound were obtained from a slow evaporation of 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 C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3) or 0.97 Å (CH2Cl) and N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(CH or NH) and Uiso(H) = 1.4 Ueq(CH3).
Since the compound was prepared in a project that ended a few years ago, the measurement was performed using the theta range that was routinely applied at that time. In view of the fact that the structure is an organic compound, which scatters with minor intensity at high theta values we feel that the presented structural information on this compound is reliable enough in order to unambigiously solve the structure and refine the structure model reliably.
In the present work, the structure of 2-chloro-N-(2,6-dimethylphenyl)- acetamide (26DMPCA) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of chemically and biologically significant compounds such as acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The structure of 26DMPCA is closely related to the side chain unsubstituted N-(2,6-dimethylphenyl)-acetamide (26DMPA) (Gowda et al., 2007c) and side chain substituted, 2,2,2-trichloro-N-(2,6-dimethylphenyl)-acetamide (26DMPTCA) (Gowda et al., 2007b) and 2,2,2-trimethyl-N- (2,6-dimethylphenyl)-acetamide (26DMPTMA) (Gowda et al., 2007d). The bond parameters in 26DMPCA are similar to those in 26DMPA, 26DMPTCA, 26DMPTMA and other acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The molecules in 26DMPcA are linked into infinite chains through N—H···O hydrogen bonding (Table 1 and Fig.2).
For related literature, see: Gowda et al. (2004, 2007a,b,c,d,e,f); Gowda, Kozisek et al. (2007); Gowda, Svoboda & Fuess (2007).
Data collection: STADI4 (Stoe & Cie, 1987); cell
STADI4 (Stoe & Cie, 1987); 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).C10H12ClNO | F(000) = 416 |
Mr = 197.66 | Dx = 1.269 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 40 reflections |
a = 13.766 (3) Å | θ = 18.0–20.9° |
b = 8.911 (2) Å | µ = 0.33 mm−1 |
c = 8.538 (2) Å | T = 300 K |
β = 99.00 (1)° | Needle, colourless |
V = 1034.4 (4) Å3 | 0.50 × 0.15 × 0.12 mm |
Z = 4 |
Stoe Stadi-4 diffractometer | 1053 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.015 |
Graphite monochromator | θmax = 22.5°, θmin = 2.7° |
Profile fitted scans 2θ/ω=1/1 | h = −14→14 |
Absorption correction: numerical (North et al., 1968) | k = 0→9 |
Tmin = 0.952, Tmax = 0.968 | l = 0→9 |
1318 measured reflections | 3 standard reflections every 200 min |
1188 independent reflections | intensity decay: 2% |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0457P)2 + 0.4775P] where P = (Fo2 + 2Fc2)/3 |
1188 reflections | (Δ/σ)max < 0.001 |
123 parameters | Δρmax = 0.18 e Å−3 |
0 restraints | Δρmin = −0.20 e Å−3 |
C10H12ClNO | V = 1034.4 (4) Å3 |
Mr = 197.66 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 13.766 (3) Å | µ = 0.33 mm−1 |
b = 8.911 (2) Å | T = 300 K |
c = 8.538 (2) Å | 0.50 × 0.15 × 0.12 mm |
β = 99.00 (1)° |
Stoe Stadi-4 diffractometer | 1053 reflections with I > 2σ(I) |
Absorption correction: numerical (North et al., 1968) | Rint = 0.015 |
Tmin = 0.952, Tmax = 0.968 | θmax = 22.5° |
1318 measured reflections | 3 standard reflections every 200 min |
1188 independent reflections | intensity decay: 2% |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.104 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | Δρmax = 0.18 e Å−3 |
1188 reflections | Δρmin = −0.20 e Å−3 |
123 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 | 0.57659 (6) | 0.28510 (10) | 0.14255 (11) | 0.0828 (3) | |
C2 | 0.49079 (17) | 0.1523 (3) | 0.1922 (3) | 0.0513 (6) | |
H2A | 0.5164 | 0.0516 | 0.1845 | 0.062* | |
H2B | 0.4798 | 0.1684 | 0.3005 | 0.062* | |
C3 | 0.39513 (17) | 0.1690 (3) | 0.0802 (3) | 0.0429 (6) | |
O4 | 0.39022 (12) | 0.1400 (2) | −0.06122 (19) | 0.0558 (5) | |
N5 | 0.31738 (15) | 0.2133 (2) | 0.1451 (3) | 0.0453 (5) | |
H5N | 0.327 (2) | 0.249 (3) | 0.240 (4) | 0.054* | |
C6 | 0.22271 (18) | 0.2355 (3) | 0.0519 (3) | 0.0427 (6) | |
C7 | 0.19078 (19) | 0.3809 (3) | 0.0168 (3) | 0.0523 (6) | |
C8 | 0.0989 (2) | 0.3999 (3) | −0.0760 (3) | 0.0649 (8) | |
H8 | 0.0753 | 0.4963 | −0.1002 | 0.078* | |
C9 | 0.0431 (2) | 0.2789 (4) | −0.1320 (4) | 0.0708 (9) | |
H9 | −0.0176 | 0.2935 | −0.1952 | 0.085* | |
C10 | 0.0758 (2) | 0.1364 (4) | −0.0957 (3) | 0.0646 (8) | |
H10 | 0.0369 | 0.0552 | −0.1342 | 0.077* | |
C11 | 0.16630 (19) | 0.1110 (3) | −0.0023 (3) | 0.0520 (6) | |
C12 | 0.2526 (2) | 0.5139 (3) | 0.0770 (4) | 0.0811 (9) | |
H12A | 0.2218 | 0.6041 | 0.0322 | 0.097* | |
H12B | 0.3166 | 0.5044 | 0.0468 | 0.097* | |
H12C | 0.2588 | 0.5181 | 0.1905 | 0.097* | |
C13 | 0.2003 (2) | −0.0464 (3) | 0.0398 (4) | 0.0719 (8) | |
H13A | 0.2543 | −0.0711 | −0.0143 | 0.086* | |
H13B | 0.1471 | −0.1152 | 0.0083 | 0.086* | |
H13C | 0.2211 | −0.0536 | 0.1522 | 0.086* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.0568 (5) | 0.1009 (7) | 0.0869 (6) | −0.0204 (4) | −0.0005 (4) | 0.0113 (4) |
C2 | 0.0438 (13) | 0.0629 (16) | 0.0463 (13) | 0.0064 (12) | 0.0042 (11) | 0.0048 (11) |
C3 | 0.0452 (14) | 0.0458 (14) | 0.0374 (14) | 0.0021 (11) | 0.0058 (10) | 0.0056 (10) |
O4 | 0.0506 (10) | 0.0790 (13) | 0.0375 (10) | 0.0091 (9) | 0.0060 (7) | −0.0012 (8) |
N5 | 0.0404 (12) | 0.0594 (13) | 0.0347 (10) | 0.0028 (9) | 0.0016 (9) | −0.0026 (9) |
C6 | 0.0374 (14) | 0.0539 (15) | 0.0372 (11) | 0.0012 (11) | 0.0073 (11) | 0.0023 (10) |
C7 | 0.0493 (15) | 0.0548 (15) | 0.0522 (14) | 0.0009 (12) | 0.0062 (12) | 0.0040 (12) |
C8 | 0.0547 (17) | 0.0666 (18) | 0.0711 (17) | 0.0146 (14) | 0.0022 (14) | 0.0140 (15) |
C9 | 0.0447 (17) | 0.094 (2) | 0.0687 (18) | 0.0043 (16) | −0.0070 (15) | 0.0096 (16) |
C10 | 0.0479 (16) | 0.076 (2) | 0.0657 (17) | −0.0097 (14) | −0.0029 (14) | −0.0065 (14) |
C11 | 0.0483 (15) | 0.0563 (15) | 0.0505 (13) | −0.0007 (12) | 0.0053 (12) | −0.0026 (12) |
C12 | 0.085 (2) | 0.0578 (18) | 0.096 (2) | −0.0039 (16) | −0.0008 (18) | 0.0036 (16) |
C13 | 0.0662 (19) | 0.0567 (17) | 0.091 (2) | −0.0056 (14) | 0.0051 (16) | −0.0014 (15) |
Cl1—C2 | 1.770 (3) | C8—H8 | 0.9300 |
C2—C3 | 1.509 (3) | C9—C10 | 1.366 (4) |
C2—H2A | 0.9700 | C9—H9 | 0.9300 |
C2—H2B | 0.9700 | C10—C11 | 1.389 (4) |
C3—O4 | 1.227 (3) | C10—H10 | 0.9300 |
C3—N5 | 1.339 (3) | C11—C13 | 1.505 (4) |
N5—C6 | 1.431 (3) | C12—H12A | 0.9600 |
N5—H5N | 0.86 (3) | C12—H12B | 0.9600 |
C6—C7 | 1.386 (3) | C12—H12C | 0.9600 |
C6—C11 | 1.391 (3) | C13—H13A | 0.9600 |
C7—C8 | 1.394 (4) | C13—H13B | 0.9600 |
C7—C12 | 1.501 (4) | C13—H13C | 0.9600 |
C8—C9 | 1.367 (4) | ||
C3—C2—Cl1 | 109.33 (17) | C10—C9—C8 | 120.4 (3) |
C3—C2—H2A | 109.8 | C10—C9—H9 | 119.8 |
Cl1—C2—H2A | 109.8 | C8—C9—H9 | 119.8 |
C3—C2—H2B | 109.8 | C9—C10—C11 | 121.1 (3) |
Cl1—C2—H2B | 109.8 | C9—C10—H10 | 119.5 |
H2A—C2—H2B | 108.3 | C11—C10—H10 | 119.5 |
O4—C3—N5 | 123.0 (2) | C10—C11—C6 | 117.7 (2) |
O4—C3—C2 | 120.8 (2) | C10—C11—C13 | 120.4 (2) |
N5—C3—C2 | 116.2 (2) | C6—C11—C13 | 121.9 (2) |
C3—N5—C6 | 121.9 (2) | C7—C12—H12A | 109.5 |
C3—N5—H5N | 119 (2) | C7—C12—H12B | 109.5 |
C6—N5—H5N | 117.6 (19) | H12A—C12—H12B | 109.5 |
C7—C6—C11 | 122.1 (2) | C7—C12—H12C | 109.5 |
C7—C6—N5 | 118.7 (2) | H12A—C12—H12C | 109.5 |
C11—C6—N5 | 119.2 (2) | H12B—C12—H12C | 109.5 |
C6—C7—C8 | 117.7 (2) | C11—C13—H13A | 109.5 |
C6—C7—C12 | 121.3 (2) | C11—C13—H13B | 109.5 |
C8—C7—C12 | 120.9 (3) | H13A—C13—H13B | 109.5 |
C9—C8—C7 | 120.9 (3) | C11—C13—H13C | 109.5 |
C9—C8—H8 | 119.5 | H13A—C13—H13C | 109.5 |
C7—C8—H8 | 119.5 | H13B—C13—H13C | 109.5 |
Cl1—C2—C3—O4 | 66.1 (3) | C6—C7—C8—C9 | −0.9 (4) |
Cl1—C2—C3—N5 | −115.4 (2) | C12—C7—C8—C9 | 179.4 (3) |
O4—C3—N5—C6 | −2.4 (4) | C7—C8—C9—C10 | 1.0 (5) |
C2—C3—N5—C6 | 179.1 (2) | C8—C9—C10—C11 | −0.3 (5) |
C3—N5—C6—C7 | −103.9 (3) | C9—C10—C11—C6 | −0.5 (4) |
C3—N5—C6—C11 | 75.3 (3) | C9—C10—C11—C13 | 178.5 (3) |
C11—C6—C7—C8 | 0.0 (4) | C7—C6—C11—C10 | 0.7 (4) |
N5—C6—C7—C8 | 179.2 (2) | N5—C6—C11—C10 | −178.5 (2) |
C11—C6—C7—C12 | 179.7 (3) | C7—C6—C11—C13 | −178.4 (3) |
N5—C6—C7—C12 | −1.1 (4) | N5—C6—C11—C13 | 2.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5N···O4i | 0.86 (3) | 2.04 (3) | 2.866 (3) | 161 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H12ClNO |
Mr | 197.66 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 300 |
a, b, c (Å) | 13.766 (3), 8.911 (2), 8.538 (2) |
β (°) | 99.00 (1) |
V (Å3) | 1034.4 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.33 |
Crystal size (mm) | 0.50 × 0.15 × 0.12 |
Data collection | |
Diffractometer | Stoe Stadi-4 diffractometer |
Absorption correction | Numerical (North et al., 1968) |
Tmin, Tmax | 0.952, 0.968 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1318, 1188, 1053 |
Rint | 0.015 |
θmax (°) | 22.5 |
(sin θ/λ)max (Å−1) | 0.538 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.104, 1.10 |
No. of reflections | 1188 |
No. of parameters | 123 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.18, −0.20 |
Computer programs: STADI4 (Stoe & Cie, 1987), 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 |
N5—H5N···O4i | 0.86 (3) | 2.04 (3) | 2.866 (3) | 161 (3) |
Symmetry code: (i) x, −y+1/2, z+1/2. |
Acknowledgements
BTG thanks the Alexander von Humboldt Foundation, Bonn, Germany, for extensions of his research fellowship.
References
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In the present work, the structure of 2-chloro-N-(2,6-dimethylphenyl)- acetamide (26DMPCA) has been determined as part of a study of the effect of ring and side chain substitutions on the solid state geometry of chemically and biologically significant compounds such as acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The structure of 26DMPCA is closely related to the side chain unsubstituted N-(2,6-dimethylphenyl)-acetamide (26DMPA) (Gowda et al., 2007c) and side chain substituted, 2,2,2-trichloro-N-(2,6-dimethylphenyl)-acetamide (26DMPTCA) (Gowda et al., 2007b) and 2,2,2-trimethyl-N- (2,6-dimethylphenyl)-acetamide (26DMPTMA) (Gowda et al., 2007d). The bond parameters in 26DMPCA are similar to those in 26DMPA, 26DMPTCA, 26DMPTMA and other acetanilides (Gowda et al., 2007a, 2007b, 2007c, 2007d, 2007e). The molecules in 26DMPcA are linked into infinite chains through N—H···O hydrogen bonding (Table 1 and Fig.2).