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The structure of the title compound, C10H13NO, is closely related to the ring-unsubstituted N-phenyl­acetamide and N-(2-methyl­phen­yl)acetamide with slightly different bond parameters. At room temperature it crystallizes in the ortho­rhom­bic space group Pbca, in contrast with the monoclinic space group P21/n observed for the low-temperature structure of the compound. The mol­ecules are linked into chains running along the a-axis direction through N—H...O hydrogen bonding.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807027031/bx2089sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807027031/bx2089Isup2.hkl
Contains datablock I

CCDC reference: 613381

Key indicators

  • Single-crystal X-ray study
  • T = 299 K
  • Mean [sigma](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

Comment top

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).

Related literature top

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).

Experimental top

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.

Refinement top

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).

Structure description top

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).

Computing details top

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.

Figures top
[Figure 1] Fig. 1. Molecular structure of the title compound showing the atom labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Typical Hydrogen bond bridges observed in the title compound
N-(2,6-Dimethylphenyl)acetamide top
Crystal data top
C10H13NOF(000) = 704
Mr = 163.21Dx = 1.122 Mg m3
Orthorhombic, PbcaCu Kα radiation, λ = 1.54180 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 9.145 (1) Åθ = 6.7–22.2°
b = 13.215 (1) ŵ = 0.57 mm1
c = 15.993 (1) ÅT = 299 K
V = 1932.8 (3) Å3Prism, colourless
Z = 80.50 × 0.13 × 0.10 mm
Data collection top
Enraf–Nonius CAD-4
diffractometer
1055 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.027
Graphite monochromatorθmax = 66.9°, θmin = 5.5°
ω/2θ scansh = 010
Absorption correction: psi-scan
(North et al., 1968)
k = 152
Tmin = 0.742, Tmax = 0.944l = 019
1917 measured reflections3 standard reflections every 120 min
1710 independent reflections intensity decay: 2.5%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.056H 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 reflectionsΔρmax = 0.20 e Å3
113 parametersΔρmin = 0.20 e Å3
1 restraintExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0014 (5)
Crystal data top
C10H13NOV = 1932.8 (3) Å3
Mr = 163.21Z = 8
Orthorhombic, PbcaCu Kα radiation
a = 9.145 (1) ŵ = 0.57 mm1
b = 13.215 (1) ÅT = 299 K
c = 15.993 (1) Å0.50 × 0.13 × 0.10 mm
Data collection top
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 = 0.9443 standard reflections every 120 min
1917 measured reflections intensity decay: 2.5%
1710 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0561 restraint
wR(F2) = 0.182H atoms treated by a mixture of independent and constrained refinement
S = 1.03Δρmax = 0.20 e Å3
1710 reflectionsΔρmin = 0.20 e Å3
113 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.2449 (3)0.9101 (3)0.13523 (16)0.0651 (8)
H1A0.22850.98100.12650.078*
H1B0.22450.87390.08450.078*
H1C0.34500.89920.15100.078*
C20.1469 (2)0.87292 (19)0.20292 (14)0.0464 (6)
C50.1374 (2)0.8040 (2)0.34433 (15)0.0479 (6)
C60.1394 (3)0.8645 (2)0.41568 (16)0.0599 (8)
C70.0703 (3)0.8280 (3)0.48692 (18)0.0833 (11)
H70.07140.86650.53560.100*
C80.0014 (4)0.7376 (4)0.4867 (3)0.1018 (15)
H80.04520.71500.53490.122*
C90.0005 (4)0.6788 (3)0.4160 (3)0.0957 (13)
H90.04810.61660.41700.115*
C100.0680 (3)0.7109 (2)0.3426 (2)0.0686 (9)
C110.0652 (5)0.6467 (2)0.2660 (3)0.0986 (13)
H11A0.02450.58170.27940.118*
H11B0.16300.63830.24540.118*
H11C0.00630.67880.22400.118*
C120.2110 (4)0.9663 (3)0.41539 (19)0.0813 (10)
H12A0.15991.01030.37750.098*
H12B0.31080.95960.39780.098*
H12C0.20800.99450.47070.098*
N40.21296 (19)0.83891 (16)0.27191 (12)0.0473 (5)
H4N0.3045 (12)0.8486 (18)0.2789 (15)0.057*
O30.01362 (17)0.87350 (17)0.19453 (10)0.0639 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0379 (12)0.097 (2)0.0600 (15)0.0013 (14)0.0082 (11)0.0107 (16)
C20.0257 (11)0.0619 (15)0.0515 (14)0.0041 (11)0.0023 (9)0.0031 (12)
C50.0282 (10)0.0649 (16)0.0504 (13)0.0041 (11)0.0019 (10)0.0103 (13)
C60.0312 (12)0.096 (2)0.0526 (15)0.0082 (14)0.0042 (10)0.0043 (15)
C70.0518 (17)0.147 (4)0.0515 (16)0.007 (2)0.0011 (13)0.012 (2)
C80.064 (2)0.163 (4)0.079 (2)0.000 (3)0.0123 (19)0.055 (3)
C90.069 (2)0.103 (3)0.114 (3)0.018 (2)0.002 (2)0.054 (3)
C100.0502 (16)0.0663 (18)0.089 (2)0.0030 (15)0.0024 (15)0.0177 (18)
C110.101 (3)0.0607 (18)0.134 (3)0.012 (2)0.009 (2)0.008 (2)
C120.068 (2)0.101 (3)0.0740 (19)0.003 (2)0.0031 (16)0.0269 (19)
N40.0229 (8)0.0694 (13)0.0497 (11)0.0020 (10)0.0016 (8)0.0018 (10)
O30.0241 (9)0.1064 (17)0.0612 (11)0.0028 (9)0.0014 (7)0.0110 (11)
Geometric parameters (Å, º) top
C1—C21.489 (3)C8—C91.372 (6)
C1—H1A0.9600C8—H80.9300
C1—H1B0.9600C9—C101.397 (5)
C1—H1C0.9600C9—H90.9300
C2—O31.226 (3)C10—C111.489 (5)
C2—N41.336 (3)C11—H11A0.9600
C5—C101.385 (4)C11—H11B0.9600
C5—C61.394 (4)C11—H11C0.9600
C5—N41.425 (3)C12—H12A0.9600
C6—C71.390 (4)C12—H12B0.9600
C6—C121.496 (4)C12—H12C0.9600
C7—C81.350 (6)N4—H4N0.854 (10)
C7—H70.9300
C2—C1—H1A109.5C8—C9—C10121.1 (4)
C2—C1—H1B109.5C8—C9—H9119.5
H1A—C1—H1B109.5C10—C9—H9119.5
C2—C1—H1C109.5C5—C10—C9117.2 (3)
H1A—C1—H1C109.5C5—C10—C11122.0 (3)
H1B—C1—H1C109.5C9—C10—C11120.7 (3)
O3—C2—N4122.8 (2)C10—C11—H11A109.5
O3—C2—C1121.1 (2)C10—C11—H11B109.5
N4—C2—C1116.1 (2)H11A—C11—H11B109.5
C10—C5—C6122.2 (2)C10—C11—H11C109.5
C10—C5—N4119.6 (3)H11A—C11—H11C109.5
C6—C5—N4118.2 (2)H11B—C11—H11C109.5
C7—C6—C5117.8 (3)C6—C12—H12A109.5
C7—C6—C12120.9 (3)C6—C12—H12B109.5
C5—C6—C12121.3 (2)H12A—C12—H12B109.5
C8—C7—C6121.2 (4)C6—C12—H12C109.5
C8—C7—H7119.4H12A—C12—H12C109.5
C6—C7—H7119.4H12B—C12—H12C109.5
C7—C8—C9120.5 (3)C2—N4—C5124.13 (18)
C7—C8—H8119.7C2—N4—H4N120.0 (17)
C9—C8—H8119.7C5—N4—H4N114.7 (17)
C10—C5—C6—C70.8 (4)N4—C5—C10—C9178.0 (2)
N4—C5—C6—C7177.6 (2)C6—C5—C10—C11179.6 (3)
C10—C5—C6—C12178.0 (3)N4—C5—C10—C112.0 (4)
N4—C5—C6—C123.6 (3)C8—C9—C10—C50.1 (5)
C5—C6—C7—C81.0 (4)C8—C9—C10—C11179.9 (3)
C12—C6—C7—C8177.8 (3)O3—C2—N4—C52.9 (4)
C6—C7—C8—C90.7 (5)C1—C2—N4—C5177.6 (3)
C7—C8—C9—C100.2 (6)C10—C5—N4—C273.7 (3)
C6—C5—C10—C90.4 (4)C6—C5—N4—C2107.9 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.85 (1)1.99 (1)2.838 (2)175 (2)
Symmetry code: (i) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC10H13NO
Mr163.21
Crystal system, space groupOrthorhombic, Pbca
Temperature (K)299
a, b, c (Å)9.145 (1), 13.215 (1), 15.993 (1)
V3)1932.8 (3)
Z8
Radiation typeCu Kα
µ (mm1)0.57
Crystal size (mm)0.50 × 0.13 × 0.10
Data collection
DiffractometerEnraf–Nonius CAD-4
Absorption correctionPsi-scan
(North et al., 1968)
Tmin, Tmax0.742, 0.944
No. of measured, independent and
observed [I > 2σ(I)] reflections
1917, 1710, 1055
Rint0.027
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.182, 1.03
No. of reflections1710
No. of parameters113
No. of restraints1
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N4—H4N···O3i0.854 (10)1.986 (10)2.838 (2)175 (2)
Symmetry code: (i) x+1/2, y, z+1/2.
 

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