organic compounds
N-Ethyl-2,2-dimethyl-N-(3-methylphenyl)propanamide
aDepartment of Studies and Research in Physics, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, bDepartment of Studies and Research in Chemistry, U.C.S., Tumkur University, Tumkur, Karnataka 572 103, India, cDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur, Karnataka 572 103, India, dDepartment of Studies in Physics, University of Mysore, Manasagangotri, Mysore, India, and eTadimety Aromatics Pvt Ltd, Hirehally Industrial Area, Tumkur, Karnataka 572 168, India
*Correspondence e-mail: drsreenivasa@yahoo.co.in
In the title compound, C14H21NO, the conformation across the N—C(O) bond is syn-periplanar, the C—N—C—C torsion being −5.9 (5)°. The atoms of the ethyl group attached to the N atom are disordered over two sets of sites with occupancy ratios of 0.65 (2):0.35 (2) (CH2) and 0.689 (14):0.311 (14) (CH3)are linked by very weak C—H⋯O interactions forming C(8) chains along [001]. C—H⋯π interactions link the molecules along the c-axis direction.
CCDC reference: 983181
Related literature
For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological activity of see: Manojkumar et al. (2013a,b). Amide groups can provide structural rigidity to molecules, see: Sreenivasa et al. (2013).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2009); cell APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).
Supporting information
CCDC reference: 983181
10.1107/S1600536814001718/hg5371sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001718/hg5371Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001718/hg5371Isup3.cml
N-Ethyl-3-methylaniline (1.00g,7.4 mmol) was taken in dry dichloromethane (10 mL) and the solution was cooled to 0 oC. To this reaction mixture 2,2-dimethylpropanoyl chloride (0.888 g, 7.4 mmol) in dichloromethane and triethylamine (1.49g, 1.48 mmol) were added slowly and the mixture was heated to 50oC for 4 hours. Reaction was monitored by TLC. Reaction mixture was cooled and washed with 10% NaHCO3 solution. The organic layer was separated, dried and concentrated to obtained crude product which was purified by
using petroleum ether: ethyl acetate (7:3) as Yellow prisms of the title compound were obtained from slow evapouration of the solution of the compound in petroleum ether: ethyl acetate (7:3).The H atoms were positioned with idealized geometry using a riding model with C-H = 0.93-0.96Å. All H atoms were refined with isotropic displacement parameters (set to 1.2-1.5 times of the Ueq of the parent atom).
value (Flack, 1983) of 0.5 (5) was obtained in the final calculation, the presence of can lead to uncertainties about the correct especially in the presence of twinning.The C8 and C9 atoms of the ethyl group attached to N atom are disordered with site occupation factors of 0.65 (2):0.35 (2) and 0.689 (14):0.311 (14) respectively.
Amides are very common in nature, formed easily and provides structural rigidity to the molecules (Sreenivasa et al. 2013).
show a broad spectrum of pharmacological properties, including antibacterial (Manojkumar et al. 2013a), anti-inflammatory, antioxidant, analgesic and antiviral activity (Manojkumar et al. 2013b). Keeping this in mind, the of the title compound was determined.For hydrogen-bond motifs, see: Bernstein et al. (1995). For the biological activity of
see: Manojkumar et al. (2013a,b). Amide groups can provide structural rigidity to molecules, see: Sreenivasa et al. (2013).Data collection: APEX2 (Bruker, 2009); cell
APEX2 and SAINT-Plus (Bruker, 2009); data reduction: SAINT-Plus and XPREP (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H21NO | Prism |
Mr = 219.32 | Dx = 1.091 Mg m−3 |
Monoclinic, P21 | Melting point: 492 K |
Hall symbol: P 2yb | Cu Kα radiation, λ = 1.54178 Å |
a = 7.631 (4) Å | Cell parameters from 172 reflections |
b = 10.878 (7) Å | θ = 5.5–65.5° |
c = 8.350 (3) Å | µ = 0.52 mm−1 |
β = 105.60 (2)° | T = 294 K |
V = 667.6 (6) Å3 | Prism, yellow |
Z = 2 | 0.22 × 0.20 × 0.16 mm |
F(000) = 240 |
Bruker APEXII diffractometer | 1883 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.034 |
Graphite monochromator | θmax = 65.5°, θmin = 5.5° |
phi and ω scans | h = −8→8 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −11→12 |
Tmin = 0.893, Tmax = 0.921 | l = −9→9 |
3786 measured reflections | 1012 standard reflections every 2 reflections |
2016 independent reflections | intensity decay: 1% |
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)] = 0.057 | H-atom parameters constrained |
wR(F2) = 0.160 | w = 1/[σ2(Fo2) + (0.093P)2 + 0.1495P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
2016 reflections | Δρmax = 0.34 e Å−3 |
172 parameters | Δρmin = −0.16 e Å−3 |
55 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 constraints | Extinction coefficient: 0.018 (4) |
Primary atom site location: structure-invariant direct methods |
C14H21NO | V = 667.6 (6) Å3 |
Mr = 219.32 | Z = 2 |
Monoclinic, P21 | Cu Kα radiation |
a = 7.631 (4) Å | µ = 0.52 mm−1 |
b = 10.878 (7) Å | T = 294 K |
c = 8.350 (3) Å | 0.22 × 0.20 × 0.16 mm |
β = 105.60 (2)° |
Bruker APEXII diffractometer | 1883 reflections with I > 2σ(I) |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | Rint = 0.034 |
Tmin = 0.893, Tmax = 0.921 | 1012 standard reflections every 2 reflections |
3786 measured reflections | intensity decay: 1% |
2016 independent reflections |
R[F2 > 2σ(F2)] = 0.057 | 55 restraints |
wR(F2) = 0.160 | H-atom parameters constrained |
S = 1.06 | Δρmax = 0.34 e Å−3 |
2016 reflections | Δρmin = −0.16 e Å−3 |
172 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 | Occ. (<1) | |
O | 0.2284 (2) | 0.7636 (3) | 0.6964 (2) | 0.0725 (7) | |
N | 0.4145 (3) | 0.7530 (3) | 0.9461 (2) | 0.0670 (8) | |
C11 | 0.5373 (3) | 0.7418 (3) | 0.6942 (3) | 0.0489 (6) | |
C6 | 0.8300 (4) | 0.8185 (3) | 1.2843 (3) | 0.0494 (6) | |
C10 | 0.3855 (3) | 0.7522 (3) | 0.7806 (3) | 0.0452 (6) | |
C4 | 0.5820 (3) | 0.7342 (3) | 1.0730 (3) | 0.0487 (7) | |
C5 | 0.6765 (4) | 0.8340 (3) | 1.1519 (3) | 0.0520 (7) | |
H5 | 0.6374 | 0.9128 | 1.1164 | 0.062* | |
C3 | 0.6371 (4) | 0.6191 (3) | 1.1298 (3) | 0.0586 (8) | |
H3 | 0.5716 | 0.5510 | 1.0789 | 0.070* | |
C2 | 0.7875 (4) | 0.6028 (3) | 1.2607 (4) | 0.0602 (8) | |
H2 | 0.8249 | 0.5239 | 1.2975 | 0.072* | |
C1 | 0.8829 (4) | 0.7029 (3) | 1.3376 (3) | 0.0520 (7) | |
H1 | 0.9848 | 0.6916 | 1.4271 | 0.062* | |
C7 | 0.9325 (5) | 0.9283 (4) | 1.3690 (5) | 0.0834 (11) | |
H7A | 0.9820 | 0.9109 | 1.4851 | 0.125* | |
H7B | 0.8515 | 0.9974 | 1.3563 | 0.125* | |
H7C | 1.0295 | 0.9472 | 1.3200 | 0.125* | |
C14 | 0.4518 (6) | 0.7552 (8) | 0.5111 (5) | 0.129 (2) | |
H14A | 0.5454 | 0.7608 | 0.4542 | 0.193* | |
H14B | 0.3787 | 0.8283 | 0.4908 | 0.193* | |
H14C | 0.3766 | 0.6849 | 0.4710 | 0.193* | |
C13 | 0.6307 (11) | 0.6209 (5) | 0.7262 (9) | 0.136 (3) | |
H13A | 0.5417 | 0.5564 | 0.7079 | 0.205* | |
H13B | 0.7044 | 0.6178 | 0.8392 | 0.205* | |
H13C | 0.7066 | 0.6103 | 0.6523 | 0.205* | |
C12 | 0.6785 (8) | 0.8393 (6) | 0.7487 (7) | 0.135 (3) | |
H12A | 0.7324 | 0.8325 | 0.8663 | 0.202* | |
H12B | 0.6230 | 0.9187 | 0.7237 | 0.202* | |
H12C | 0.7708 | 0.8293 | 0.6910 | 0.202* | |
C8A | 0.2598 (9) | 0.7879 (9) | 1.0135 (7) | 0.052 (2) | 0.65 (2) |
H8A1 | 0.1744 | 0.8395 | 0.9348 | 0.063* | 0.65 (2) |
H8A2 | 0.3035 | 0.8329 | 1.1169 | 0.063* | 0.65 (2) |
C8B | 0.2459 (15) | 0.7104 (19) | 1.0046 (14) | 0.059 (4) | 0.35 (2) |
H8B1 | 0.1529 | 0.6742 | 0.9142 | 0.070* | 0.35 (2) |
H8B2 | 0.2801 | 0.6522 | 1.0958 | 0.070* | 0.35 (2) |
C9A | 0.1691 (10) | 0.6700 (7) | 1.0428 (8) | 0.087 (2) | 0.689 (14) |
H9A1 | 0.1289 | 0.6256 | 0.9400 | 0.131* | 0.689 (14) |
H9A2 | 0.0664 | 0.6887 | 1.0843 | 0.131* | 0.689 (14) |
H9A3 | 0.2542 | 0.6207 | 1.1226 | 0.131* | 0.689 (14) |
C9B | 0.1877 (19) | 0.8243 (14) | 1.0567 (15) | 0.071 (4) | 0.311 (14) |
H9B1 | 0.2883 | 0.8636 | 1.1337 | 0.107* | 0.311 (14) |
H9B2 | 0.0925 | 0.8096 | 1.1096 | 0.107* | 0.311 (14) |
H9B3 | 0.1429 | 0.8765 | 0.9617 | 0.107* | 0.311 (14) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O | 0.0395 (10) | 0.130 (2) | 0.0405 (9) | 0.0096 (12) | −0.0029 (8) | −0.0003 (11) |
N | 0.0294 (10) | 0.136 (2) | 0.0338 (10) | 0.0065 (14) | 0.0055 (8) | 0.0032 (14) |
C11 | 0.0481 (13) | 0.0608 (15) | 0.0394 (12) | 0.0028 (13) | 0.0147 (10) | 0.0013 (11) |
C6 | 0.0429 (14) | 0.0613 (17) | 0.0417 (12) | −0.0053 (13) | 0.0072 (10) | 0.0004 (12) |
C10 | 0.0375 (12) | 0.0603 (14) | 0.0343 (11) | −0.0002 (12) | 0.0038 (9) | −0.0004 (11) |
C4 | 0.0336 (12) | 0.0806 (19) | 0.0298 (10) | 0.0034 (13) | 0.0051 (9) | 0.0036 (12) |
C5 | 0.0456 (15) | 0.0645 (17) | 0.0427 (13) | 0.0073 (13) | 0.0063 (11) | 0.0077 (12) |
C3 | 0.0559 (17) | 0.0689 (19) | 0.0469 (15) | −0.0075 (15) | 0.0067 (13) | −0.0085 (13) |
C2 | 0.0631 (18) | 0.0565 (17) | 0.0542 (15) | 0.0061 (14) | 0.0040 (14) | 0.0069 (13) |
C1 | 0.0417 (15) | 0.0677 (18) | 0.0404 (12) | 0.0050 (13) | 0.0003 (11) | 0.0069 (12) |
C7 | 0.079 (2) | 0.073 (2) | 0.083 (3) | −0.0182 (19) | −0.0049 (19) | −0.0069 (18) |
C14 | 0.086 (3) | 0.254 (7) | 0.0529 (18) | 0.027 (4) | 0.0323 (19) | 0.021 (3) |
C13 | 0.189 (6) | 0.118 (4) | 0.150 (5) | 0.083 (4) | 0.126 (5) | 0.052 (3) |
C12 | 0.134 (4) | 0.178 (5) | 0.125 (4) | −0.087 (4) | 0.091 (4) | −0.062 (4) |
C8A | 0.038 (3) | 0.075 (5) | 0.045 (2) | 0.006 (3) | 0.0115 (19) | −0.008 (3) |
C8B | 0.037 (5) | 0.083 (10) | 0.054 (5) | −0.014 (6) | 0.009 (4) | 0.001 (5) |
C9A | 0.066 (4) | 0.110 (5) | 0.101 (4) | −0.013 (3) | 0.049 (3) | 0.001 (4) |
C9B | 0.057 (7) | 0.095 (8) | 0.073 (7) | 0.006 (6) | 0.035 (5) | 0.003 (6) |
O—C10 | 1.222 (3) | C7—H7C | 0.9600 |
N—C10 | 1.339 (3) | C14—H14A | 0.9600 |
N—C4 | 1.439 (3) | C14—H14B | 0.9600 |
N—C8A | 1.488 (7) | C14—H14C | 0.9600 |
N—C8B | 1.564 (12) | C13—H13A | 0.9600 |
C11—C13 | 1.486 (5) | C13—H13B | 0.9600 |
C11—C12 | 1.493 (5) | C13—H13C | 0.9600 |
C11—C14 | 1.499 (5) | C12—H12A | 0.9600 |
C11—C10 | 1.525 (3) | C12—H12B | 0.9600 |
C6—C1 | 1.359 (4) | C12—H12C | 0.9600 |
C6—C5 | 1.388 (4) | C8A—C9A | 1.508 (13) |
C6—C7 | 1.497 (5) | C8A—H8A1 | 0.9700 |
C4—C3 | 1.364 (4) | C8A—H8A2 | 0.9700 |
C4—C5 | 1.370 (4) | C8B—C9B | 1.42 (3) |
C5—H5 | 0.9300 | C8B—H8B1 | 0.9700 |
C3—C2 | 1.367 (4) | C8B—H8B2 | 0.9700 |
C3—H3 | 0.9300 | C9A—H9A1 | 0.9600 |
C2—C1 | 1.370 (4) | C9A—H9A2 | 0.9600 |
C2—H2 | 0.9300 | C9A—H9A3 | 0.9600 |
C1—H1 | 0.9300 | C9B—H9B1 | 0.9600 |
C7—H7A | 0.9600 | C9B—H9B2 | 0.9600 |
C7—H7B | 0.9600 | C9B—H9B3 | 0.9600 |
C10—N—C4 | 128.83 (19) | H7B—C7—H7C | 109.5 |
C10—N—C8A | 117.7 (3) | C11—C14—H14A | 109.5 |
C4—N—C8A | 113.3 (2) | C11—C14—H14B | 109.5 |
C10—N—C8B | 113.5 (5) | H14A—C14—H14B | 109.5 |
C4—N—C8B | 111.7 (4) | C11—C14—H14C | 109.5 |
C13—C11—C12 | 107.6 (5) | H14A—C14—H14C | 109.5 |
C13—C11—C14 | 109.0 (4) | H14B—C14—H14C | 109.5 |
C12—C11—C14 | 108.8 (4) | C11—C13—H13A | 109.5 |
C13—C11—C10 | 111.7 (3) | C11—C13—H13B | 109.5 |
C12—C11—C10 | 112.4 (3) | H13A—C13—H13B | 109.5 |
C14—C11—C10 | 107.3 (2) | C11—C13—H13C | 109.5 |
C1—C6—C5 | 119.1 (3) | H13A—C13—H13C | 109.5 |
C1—C6—C7 | 120.8 (3) | H13B—C13—H13C | 109.5 |
C5—C6—C7 | 120.1 (3) | C11—C12—H12A | 109.5 |
O—C10—N | 117.2 (2) | C11—C12—H12B | 109.5 |
O—C10—C11 | 119.2 (2) | H12A—C12—H12B | 109.5 |
N—C10—C11 | 123.6 (2) | C11—C12—H12C | 109.5 |
C3—C4—C5 | 119.1 (2) | H12A—C12—H12C | 109.5 |
C3—C4—N | 121.1 (3) | H12B—C12—H12C | 109.5 |
C5—C4—N | 119.3 (3) | N—C8A—C9A | 106.8 (6) |
C4—C5—C6 | 120.6 (3) | N—C8A—H8A1 | 110.4 |
C4—C5—H5 | 119.7 | C9A—C8A—H8A1 | 110.4 |
C6—C5—H5 | 119.7 | N—C8A—H8A2 | 110.4 |
C4—C3—C2 | 120.7 (3) | C9A—C8A—H8A2 | 110.4 |
C4—C3—H3 | 119.6 | H8A1—C8A—H8A2 | 108.6 |
C2—C3—H3 | 119.6 | C9B—C8B—N | 100.9 (13) |
C3—C2—C1 | 119.9 (3) | C9B—C8B—H8B1 | 111.6 |
C3—C2—H2 | 120.1 | N—C8B—H8B1 | 111.6 |
C1—C2—H2 | 120.1 | C9B—C8B—H8B2 | 111.6 |
C6—C1—C2 | 120.6 (2) | N—C8B—H8B2 | 111.6 |
C6—C1—H1 | 119.7 | H8B1—C8B—H8B2 | 109.4 |
C2—C1—H1 | 119.7 | C8A—C9A—H9A1 | 109.5 |
C6—C7—H7A | 109.5 | C8A—C9A—H9A2 | 109.5 |
C6—C7—H7B | 109.5 | H9A1—C9A—H9A2 | 109.5 |
H7A—C7—H7B | 109.5 | C8A—C9A—H9A3 | 109.5 |
C6—C7—H7C | 109.5 | H9A1—C9A—H9A3 | 109.5 |
H7A—C7—H7C | 109.5 | H9A2—C9A—H9A3 | 109.5 |
C4—N—C10—O | 175.9 (3) | C8B—N—C4—C5 | −109.8 (9) |
C8A—N—C10—O | −9.8 (6) | C3—C4—C5—C6 | 2.2 (4) |
C8B—N—C10—O | 25.7 (9) | N—C4—C5—C6 | 174.5 (2) |
C4—N—C10—C11 | −5.9 (5) | C1—C6—C5—C4 | −1.7 (4) |
C8A—N—C10—C11 | 168.3 (5) | C7—C6—C5—C4 | 179.8 (3) |
C8B—N—C10—C11 | −156.1 (9) | C5—C4—C3—C2 | −1.8 (4) |
C13—C11—C10—O | −116.5 (5) | N—C4—C3—C2 | −174.0 (3) |
C12—C11—C10—O | 122.5 (4) | C4—C3—C2—C1 | 0.9 (5) |
C14—C11—C10—O | 2.9 (5) | C5—C6—C1—C2 | 0.8 (4) |
C13—C11—C10—N | 65.3 (5) | C7—C6—C1—C2 | 179.3 (3) |
C12—C11—C10—N | −55.7 (5) | C3—C2—C1—C6 | −0.4 (4) |
C14—C11—C10—N | −175.2 (4) | C10—N—C8A—C9A | 94.8 (5) |
C10—N—C4—C3 | −88.2 (4) | C4—N—C8A—C9A | −90.0 (5) |
C8A—N—C4—C3 | 97.3 (5) | C8B—N—C8A—C9A | 4.1 (8) |
C8B—N—C4—C3 | 62.4 (9) | C10—N—C8B—C9B | −107.2 (7) |
C10—N—C4—C5 | 99.6 (4) | C4—N—C8B—C9B | 97.4 (8) |
C8A—N—C4—C5 | −74.9 (5) | C8A—N—C8B—C9B | −2.2 (6) |
Cg is the centoid of the benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Oi | 0.93 | 2.62 | 3.481 (2) | 153 |
C14—H14A···Cgii | 0.96 | 2.85 | 3.769 (8) | 161 |
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1. |
Cg is the centoid of the benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
C1—H1···Oi | 0.93 | 2.623 | 3.481 (2) | 153 |
C14—H14A···Cgii | 0.96 | 2.85 | 3.769 (8) | 161 |
Symmetry codes: (i) x+1, y, z+1; (ii) x, y, z+1. |
Acknowledgements
The authors acknowledge the IOE X-ray diffractometer facility, University of Mysore, Mysore, for the data collection. BSPM thanks Dr H. C. Devarajegowda, Department of Physics, Yuvarajas College (constituent), University of Mysore, for his support and guidence.
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Amides are very common in nature, formed easily and provides structural rigidity to the molecules (Sreenivasa et al. 2013). Amides show a broad spectrum of pharmacological properties, including antibacterial (Manojkumar et al. 2013a), anti-inflammatory, antioxidant, analgesic and antiviral activity (Manojkumar et al. 2013b). Keeping this in mind, the crystal structure of the title compound was determined.