Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027031/bx2089sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027031/bx2089Isup2.hkl |
CCDC reference: 613381
Key indicators
- Single-crystal X-ray study
- T = 299 K
- Mean (C-C) = 0.005 Å
- R factor = 0.056
- wR factor = 0.182
- Data-to-parameter ratio = 15.1
checkCIF/PLATON results
No syntax errors found
Alert level C PLAT031_ALERT_4_C Refined Extinction Parameter within Range ...... 2.80 Sigma PLAT153_ALERT_1_C The su's on the Cell Axes are Equal (x 100000) 100 Ang. PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 = 3 PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor .... 2.08 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 5
Alert level G PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints ....... 1
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 3 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
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.
All H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (CH aromatic) or 0.96 Å (CH3) and N—H = 0.86 Å with Uiso(H) = 1.2 Ueq(CH or NH) and Uiso(H) = 1.5 Ueq(CH3).
Amides are of fundamental chemical interest as conjugation between the nitrogen lone pair electrons and the carbonyl pi-bond results in distinct physical and chemical properties. Further the amide moiety is an important constituent of many biologically significant compounds. Thus the structural studies of amides are of interest(Brown, 1966; Nagarajan et al., 1986; Hanson et al., 2004; Gowda, Foro & Fuess, 2007a,b; Gowda et al., 2007; Gowda, Kozisek, Tokarcik & Fuess, 20 07a,b). In the present work, the structure of N-(2,6-dimethylphenyl)-acetamide (26DMPA) has been determined at 299 (2) K, as part of our 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, Foro & Fuess, 2007a,b; Gowda et al., 2007; Gowda, Kozisek, Tokarcik & Fuess, 2007a,b). The present high temperature structure (299 (2) K) crystallizes in orthorhombic Pbca space group, in contrast to the monoclinic P21/n space group (Z = 4, a = 7.6836 (6) Å, b = 16.0769 (11) Å, c = 8.1209 (4) Å, beta = 111.881 (4)°) low temperature (173 K) structure of the compound (Hanson et al., 2004). The molecules in the title compound are linked into chains as layers running along the a axis direction through N—H···O hydrogen bonding (Table 1, Fig.2).
For related literature, see: Brown (1966); Gowda et al. (2004, 2007); Gowda, Foro & Fuess (2007a, 2007b); Gowda et al., 2007; Gowda, Kozisek, Tokarcik & Fuess (2007a, 2007b); Hanson et al. (2004); Nagarajan et al. (1986).
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: PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.
C10H13NO | F(000) = 704 |
Mr = 163.21 | Dx = 1.122 Mg m−3 |
Orthorhombic, Pbca | Cu Kα radiation, λ = 1.54180 Å |
Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
a = 9.145 (1) Å | θ = 6.7–22.2° |
b = 13.215 (1) Å | µ = 0.57 mm−1 |
c = 15.993 (1) Å | T = 299 K |
V = 1932.8 (3) Å3 | Prism, colourless |
Z = 8 | 0.50 × 0.13 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1055 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.027 |
Graphite monochromator | θmax = 66.9°, θmin = 5.5° |
ω/2θ scans | h = 0→10 |
Absorption correction: psi-scan (North et al., 1968) | k = −15→2 |
Tmin = 0.742, Tmax = 0.944 | l = 0→19 |
1917 measured reflections | 3 standard reflections every 120 min |
1710 independent reflections | intensity decay: 2.5% |
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)] = 0.056 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.182 | w = 1/[σ2(Fo2) + (0.104P)2 + 0.094P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.004 |
1710 reflections | Δρmax = 0.20 e Å−3 |
113 parameters | Δρmin = −0.20 e Å−3 |
1 restraint | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0014 (5) |
C10H13NO | V = 1932.8 (3) Å3 |
Mr = 163.21 | Z = 8 |
Orthorhombic, Pbca | Cu Kα radiation |
a = 9.145 (1) Å | µ = 0.57 mm−1 |
b = 13.215 (1) Å | T = 299 K |
c = 15.993 (1) Å | 0.50 × 0.13 × 0.10 mm |
Enraf–Nonius CAD-4 diffractometer | 1055 reflections with I > 2σ(I) |
Absorption correction: psi-scan (North et al., 1968) | Rint = 0.027 |
Tmin = 0.742, Tmax = 0.944 | 3 standard reflections every 120 min |
1917 measured reflections | intensity decay: 2.5% |
1710 independent reflections |
R[F2 > 2σ(F2)] = 0.056 | 1 restraint |
wR(F2) = 0.182 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.03 | Δρmax = 0.20 e Å−3 |
1710 reflections | Δρmin = −0.20 e Å−3 |
113 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 | ||
C1 | 0.2449 (3) | 0.9101 (3) | 0.13523 (16) | 0.0651 (8) | |
H1A | 0.2285 | 0.9810 | 0.1265 | 0.078* | |
H1B | 0.2245 | 0.8739 | 0.0845 | 0.078* | |
H1C | 0.3450 | 0.8992 | 0.1510 | 0.078* | |
C2 | 0.1469 (2) | 0.87292 (19) | 0.20292 (14) | 0.0464 (6) | |
C5 | 0.1374 (2) | 0.8040 (2) | 0.34433 (15) | 0.0479 (6) | |
C6 | 0.1394 (3) | 0.8645 (2) | 0.41568 (16) | 0.0599 (8) | |
C7 | 0.0703 (3) | 0.8280 (3) | 0.48692 (18) | 0.0833 (11) | |
H7 | 0.0714 | 0.8665 | 0.5356 | 0.100* | |
C8 | 0.0014 (4) | 0.7376 (4) | 0.4867 (3) | 0.1018 (15) | |
H8 | −0.0452 | 0.7150 | 0.5349 | 0.122* | |
C9 | −0.0005 (4) | 0.6788 (3) | 0.4160 (3) | 0.0957 (13) | |
H9 | −0.0481 | 0.6166 | 0.4170 | 0.115* | |
C10 | 0.0680 (3) | 0.7109 (2) | 0.3426 (2) | 0.0686 (9) | |
C11 | 0.0652 (5) | 0.6467 (2) | 0.2660 (3) | 0.0986 (13) | |
H11A | 0.0245 | 0.5817 | 0.2794 | 0.118* | |
H11B | 0.1630 | 0.6383 | 0.2454 | 0.118* | |
H11C | 0.0063 | 0.6788 | 0.2240 | 0.118* | |
C12 | 0.2110 (4) | 0.9663 (3) | 0.41539 (19) | 0.0813 (10) | |
H12A | 0.1599 | 1.0103 | 0.3775 | 0.098* | |
H12B | 0.3108 | 0.9596 | 0.3978 | 0.098* | |
H12C | 0.2080 | 0.9945 | 0.4707 | 0.098* | |
N4 | 0.21296 (19) | 0.83891 (16) | 0.27191 (12) | 0.0473 (5) | |
H4N | 0.3045 (12) | 0.8486 (18) | 0.2789 (15) | 0.057* | |
O3 | 0.01362 (17) | 0.87350 (17) | 0.19453 (10) | 0.0639 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0379 (12) | 0.097 (2) | 0.0600 (15) | −0.0013 (14) | 0.0082 (11) | 0.0107 (16) |
C2 | 0.0257 (11) | 0.0619 (15) | 0.0515 (14) | 0.0041 (11) | 0.0023 (9) | −0.0031 (12) |
C5 | 0.0282 (10) | 0.0649 (16) | 0.0504 (13) | 0.0041 (11) | −0.0019 (10) | 0.0103 (13) |
C6 | 0.0312 (12) | 0.096 (2) | 0.0526 (15) | 0.0082 (14) | −0.0042 (10) | 0.0043 (15) |
C7 | 0.0518 (17) | 0.147 (4) | 0.0515 (16) | 0.007 (2) | 0.0011 (13) | 0.012 (2) |
C8 | 0.064 (2) | 0.163 (4) | 0.079 (2) | 0.000 (3) | 0.0123 (19) | 0.055 (3) |
C9 | 0.069 (2) | 0.103 (3) | 0.114 (3) | −0.018 (2) | −0.002 (2) | 0.054 (3) |
C10 | 0.0502 (16) | 0.0663 (18) | 0.089 (2) | −0.0030 (15) | −0.0024 (15) | 0.0177 (18) |
C11 | 0.101 (3) | 0.0607 (18) | 0.134 (3) | −0.012 (2) | −0.009 (2) | −0.008 (2) |
C12 | 0.068 (2) | 0.101 (3) | 0.0740 (19) | −0.003 (2) | −0.0031 (16) | −0.0269 (19) |
N4 | 0.0229 (8) | 0.0694 (13) | 0.0497 (11) | −0.0020 (10) | −0.0016 (8) | 0.0018 (10) |
O3 | 0.0241 (9) | 0.1064 (17) | 0.0612 (11) | 0.0028 (9) | −0.0014 (7) | 0.0110 (11) |
C1—C2 | 1.489 (3) | C8—C9 | 1.372 (6) |
C1—H1A | 0.9600 | C8—H8 | 0.9300 |
C1—H1B | 0.9600 | C9—C10 | 1.397 (5) |
C1—H1C | 0.9600 | C9—H9 | 0.9300 |
C2—O3 | 1.226 (3) | C10—C11 | 1.489 (5) |
C2—N4 | 1.336 (3) | C11—H11A | 0.9600 |
C5—C10 | 1.385 (4) | C11—H11B | 0.9600 |
C5—C6 | 1.394 (4) | C11—H11C | 0.9600 |
C5—N4 | 1.425 (3) | C12—H12A | 0.9600 |
C6—C7 | 1.390 (4) | C12—H12B | 0.9600 |
C6—C12 | 1.496 (4) | C12—H12C | 0.9600 |
C7—C8 | 1.350 (6) | N4—H4N | 0.854 (10) |
C7—H7 | 0.9300 | ||
C2—C1—H1A | 109.5 | C8—C9—C10 | 121.1 (4) |
C2—C1—H1B | 109.5 | C8—C9—H9 | 119.5 |
H1A—C1—H1B | 109.5 | C10—C9—H9 | 119.5 |
C2—C1—H1C | 109.5 | C5—C10—C9 | 117.2 (3) |
H1A—C1—H1C | 109.5 | C5—C10—C11 | 122.0 (3) |
H1B—C1—H1C | 109.5 | C9—C10—C11 | 120.7 (3) |
O3—C2—N4 | 122.8 (2) | C10—C11—H11A | 109.5 |
O3—C2—C1 | 121.1 (2) | C10—C11—H11B | 109.5 |
N4—C2—C1 | 116.1 (2) | H11A—C11—H11B | 109.5 |
C10—C5—C6 | 122.2 (2) | C10—C11—H11C | 109.5 |
C10—C5—N4 | 119.6 (3) | H11A—C11—H11C | 109.5 |
C6—C5—N4 | 118.2 (2) | H11B—C11—H11C | 109.5 |
C7—C6—C5 | 117.8 (3) | C6—C12—H12A | 109.5 |
C7—C6—C12 | 120.9 (3) | C6—C12—H12B | 109.5 |
C5—C6—C12 | 121.3 (2) | H12A—C12—H12B | 109.5 |
C8—C7—C6 | 121.2 (4) | C6—C12—H12C | 109.5 |
C8—C7—H7 | 119.4 | H12A—C12—H12C | 109.5 |
C6—C7—H7 | 119.4 | H12B—C12—H12C | 109.5 |
C7—C8—C9 | 120.5 (3) | C2—N4—C5 | 124.13 (18) |
C7—C8—H8 | 119.7 | C2—N4—H4N | 120.0 (17) |
C9—C8—H8 | 119.7 | C5—N4—H4N | 114.7 (17) |
C10—C5—C6—C7 | 0.8 (4) | N4—C5—C10—C9 | 178.0 (2) |
N4—C5—C6—C7 | −177.6 (2) | C6—C5—C10—C11 | 179.6 (3) |
C10—C5—C6—C12 | −178.0 (3) | N4—C5—C10—C11 | −2.0 (4) |
N4—C5—C6—C12 | 3.6 (3) | C8—C9—C10—C5 | 0.1 (5) |
C5—C6—C7—C8 | −1.0 (4) | C8—C9—C10—C11 | −179.9 (3) |
C12—C6—C7—C8 | 177.8 (3) | O3—C2—N4—C5 | −2.9 (4) |
C6—C7—C8—C9 | 0.7 (5) | C1—C2—N4—C5 | 177.6 (3) |
C7—C8—C9—C10 | −0.2 (6) | C10—C5—N4—C2 | 73.7 (3) |
C6—C5—C10—C9 | −0.4 (4) | C6—C5—N4—C2 | −107.9 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O3i | 0.85 (1) | 1.99 (1) | 2.838 (2) | 175 (2) |
Symmetry code: (i) x+1/2, y, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C10H13NO |
Mr | 163.21 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 299 |
a, b, c (Å) | 9.145 (1), 13.215 (1), 15.993 (1) |
V (Å3) | 1932.8 (3) |
Z | 8 |
Radiation type | Cu Kα |
µ (mm−1) | 0.57 |
Crystal size (mm) | 0.50 × 0.13 × 0.10 |
Data collection | |
Diffractometer | Enraf–Nonius CAD-4 |
Absorption correction | Psi-scan (North et al., 1968) |
Tmin, Tmax | 0.742, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 1917, 1710, 1055 |
Rint | 0.027 |
(sin θ/λ)max (Å−1) | 0.597 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.056, 0.182, 1.03 |
No. of reflections | 1710 |
No. of parameters | 113 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.20, −0.20 |
Computer programs: CAD-4-PC (Enraf–Nonius, 1996), CAD-4-PC, REDU4 (Stoe & Cie, 1987), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997), SHELXL97.
D—H···A | D—H | H···A | D···A | D—H···A |
N4—H4N···O3i | 0.854 (10) | 1.986 (10) | 2.838 (2) | 175 (2) |
Symmetry code: (i) x+1/2, y, −z+1/2. |
Amides are of fundamental chemical interest as conjugation between the nitrogen lone pair electrons and the carbonyl pi-bond results in distinct physical and chemical properties. Further the amide moiety is an important constituent of many biologically significant compounds. Thus the structural studies of amides are of interest(Brown, 1966; Nagarajan et al., 1986; Hanson et al., 2004; Gowda, Foro & Fuess, 2007a,b; Gowda et al., 2007; Gowda, Kozisek, Tokarcik & Fuess, 20 07a,b). In the present work, the structure of N-(2,6-dimethylphenyl)-acetamide (26DMPA) has been determined at 299 (2) K, as part of our 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, Foro & Fuess, 2007a,b; Gowda et al., 2007; Gowda, Kozisek, Tokarcik & Fuess, 2007a,b). The present high temperature structure (299 (2) K) crystallizes in orthorhombic Pbca space group, in contrast to the monoclinic P21/n space group (Z = 4, a = 7.6836 (6) Å, b = 16.0769 (11) Å, c = 8.1209 (4) Å, beta = 111.881 (4)°) low temperature (173 K) structure of the compound (Hanson et al., 2004). The molecules in the title compound are linked into chains as layers running along the a axis direction through N—H···O hydrogen bonding (Table 1, Fig.2).