N-(3,5-Dimethyl­phen­yl)acetamide

Gowda, B.T.; Kožíšek, J.; Tokarčík, M.; Fuess, H.

doi:10.1107/S1600536807019812

N-(3,5-Dimethylphenyl)acetamide

B. T. Gowda, J. Kožíšek, M. Tokarčík and H. Fuess

The structure of the title compound (35DMPA), C₁₀H₁₃NO, closely resembles those of N-(3,5-dichlorophenyl)acetamide (35DCPA) and other amides. 35DMPA has two molecules in its asymmetric unit, in contrast to the single molecule observed in the asymmetric unit of 35DCPA. In addition, 35DMPA and 35DCPA crystallize in different crystal systems. The molecules in 35DMPA are packed into chains via N—H

O hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807019812/dn2166sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807019812/dn2166Isup2.hkl Contains datablock I

CCDC reference: 647705

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Key indicators

Single-crystal X-ray study
T = 295 K
Mean (C-C) = 0.004 Å
R factor = 0.066
wR factor = 0.175
Data-to-parameter ratio = 15.7

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No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         48 Perc.
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT250_ALERT_2_C Large U3/U1 Ratio for Average U(i,j) Tensor ....       2.31
PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety        C20

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 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
   1 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

In the present work, the structure of N-(3,5-dimethylphenyl)acetamide (35DMPA) has been determined to explore the substituent effects on the structures of N-aromatic amides (Gowda, Foro & Fuess, 2007; Gowda et al., 2007, 2007a, 2007b). 35DMPA has two molecules in its asymmetric unit (Fig. 1), in contrast to single molecule observed in the asymmetric unit of N-(3,5-dichlorophenyl)acetamide (35DCPA). Further, 35DMPA and 35DCPA crystallize in different space group, 35DMPA in monoclinic, P21/c and 35DCPA in orthorhombic, Pna21 (Gowda et al., 2007b), respectively. The bond lengths and angles in 35DMPA show normal values. Molecules in 35DMPA form chains by hydrogen bonding, along the base vector [201] (Table 1 and Fig. 2).

Related literature top

For related structures, see: Gowda, Foro & Fuess (2007); Gowda et al., 2007; Gowda et al., 2007a,b; Shilpa & Gowda (2007).

Experimental top

The title compound was prepared according to the literature method of Shilpa and Gowda (Shilpa & Gowda, 2007). The purity of the compound was checked by determining its melting point. It was characterized by recording its infrared, NMR (Shilpa & Gowda, 2007). Single crystals of the title compound were obtained from a slow evaporation of its ethanolic solution and used for X-ray diffraction studies at room temperature.

Structure description top

For related structures, see: Gowda, Foro & Fuess (2007); Gowda et al., 2007; Gowda et al., 2007a,b; Shilpa & Gowda (2007).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2007); cell refinement: CrysAlis RED (Oxford Diffraction, 2007); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).

Figures top

	Fig. 1. Molecular structure of (I) showing the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Part of the crystal structure of (I) showing formation of a chain along the base vector [2 0 1]. H atoms not involved in hydrogen bonding are omitted. Symmetry codes: (i): -1 + x,y,z (ii): x,1/2 - y,1/2 + z

N-(3,5-dimethylphenyl)acetamide top

Crystal data top

C₁₀H₁₃NO	F(000) = 704
M_r = 163.21	D_x = 1.165 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2654 reflections
a = 8.7925 (12) Å	θ = 3.0–29.5°
b = 27.690 (5) Å	µ = 0.08 mm⁻¹
c = 7.6525 (15) Å	T = 295 K
β = 92.65 (1)°	Block, colourless transparent
V = 1861.1 (6) Å³	0.31 × 0.26 × 0.08 mm
Z = 8

Data collection top

Xcalibur System, Oxford Diffraction, Ltd. diffractometer	3638 independent reflections
Graphite monochromator	1750 reflections with I > 2σ(I)
Detector resolution: 10.434 pixels mm^-1	R_int = 0.076
φ scans, and ω scans with κ offsets	θ_max = 26.0°, θ_min = 5.1°
Absorption correction: analytical (Clark & Reid, 1995)	h = −10→10
T_min = 0.965, T_max = 0.991	k = −34→34
17320 measured reflections	l = −9→9

Refinement top

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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.175	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0775P)²] where P = (F_o² + 2F_c²)/3
3638 reflections	(Δ/σ)_max = 0.001
231 parameters	Δρ_max = 0.16 e Å⁻³
56 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₀H₁₃NO	V = 1861.1 (6) Å³
M_r = 163.21	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7925 (12) Å	µ = 0.08 mm⁻¹
b = 27.690 (5) Å	T = 295 K
c = 7.6525 (15) Å	0.31 × 0.26 × 0.08 mm
β = 92.65 (1)°

Data collection top

Xcalibur System, Oxford Diffraction, Ltd. diffractometer	3638 independent reflections
Absorption correction: analytical (Clark & Reid, 1995)	1750 reflections with I > 2σ(I)
T_min = 0.965, T_max = 0.991	R_int = 0.076
17320 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.066	56 restraints
wR(F²) = 0.175	H-atom parameters constrained
S = 0.99	Δρ_max = 0.16 e Å⁻³
3638 reflections	Δρ_min = −0.15 e Å⁻³
231 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

	x	y	z	U_iso*/U_eq
C1	0.1177 (3)	0.19573 (10)	0.7152 (4)	0.0686 (8)
H1A	0.1829	0.178	0.641	0.103*
H1B	0.0196	0.1999	0.6567	0.103*
H1C	0.1066	0.1782	0.8221	0.103*
C2	0.1856 (3)	0.24375 (10)	0.7550 (3)	0.0571 (7)
C3	0.1248 (3)	0.33115 (10)	0.7634 (3)	0.0521 (7)
C4	0.2699 (3)	0.34970 (10)	0.7820 (3)	0.0556 (7)
H4	0.3539	0.3302	0.7642	0.067*
C5	0.2888 (3)	0.39746 (11)	0.8275 (4)	0.0606 (8)
C6	0.1616 (3)	0.42655 (11)	0.8545 (4)	0.0654 (8)
H6	0.1764	0.4586	0.8872	0.079*
C7	0.0158 (3)	0.40896 (11)	0.8341 (4)	0.0628 (8)
C8	0.0000 (3)	0.36131 (11)	0.7880 (3)	0.0584 (7)
H8	−0.0975	0.3485	0.7725	0.07*
C9	0.4470 (3)	0.41717 (12)	0.8490 (4)	0.0808 (10)
H9A	0.5021	0.3998	0.9403	0.121*
H9B	0.4427	0.4508	0.8793	0.121*
H9C	0.4977	0.4135	0.7414	0.121*
C10	−0.1225 (4)	0.44042 (12)	0.8622 (5)	0.0896 (11)
H10A	−0.1969	0.4354	0.7681	0.134*
H10B	−0.0924	0.4738	0.8652	0.134*
H10C	−0.1656	0.432	0.9711	0.134*
O1	0.3102 (2)	0.24743 (7)	0.8168 (3)	0.0835 (7)
N1	0.0982 (2)	0.28246 (8)	0.7227 (3)	0.0581 (6)
H1N	0.0123	0.2766	0.6686	0.07*
C11	0.6329 (3)	0.20839 (10)	0.4921 (4)	0.0673 (8)
H11A	0.6261	0.1979	0.3723	0.101*
H11B	0.5345	0.2061	0.5408	0.101*
H11C	0.7038	0.1883	0.5575	0.101*
C12	0.6859 (3)	0.25926 (10)	0.5005 (3)	0.0570 (7)
C13	0.6067 (3)	0.34252 (10)	0.4195 (3)	0.0524 (7)
C14	0.7468 (3)	0.36566 (11)	0.4156 (3)	0.0609 (8)
H14	0.8353	0.3478	0.4372	0.073*
C15	0.7582 (3)	0.41434 (11)	0.3807 (4)	0.0637 (8)
C16	0.6270 (3)	0.44056 (11)	0.3536 (4)	0.0662 (8)
H16	0.633	0.4735	0.3317	0.079*
C17	0.4852 (3)	0.41861 (11)	0.3583 (4)	0.0616 (8)
C18	0.4771 (3)	0.36980 (11)	0.3900 (3)	0.0582 (7)
H18	0.3823	0.3549	0.3916	0.07*
C19	0.9129 (4)	0.43826 (12)	0.3724 (5)	0.0913 (11)
H19A	0.9569	0.4302	0.2636	0.137*
H19B	0.9783	0.427	0.4678	0.137*
H19C	0.9014	0.4727	0.3805	0.137*
C20	0.3427 (4)	0.44701 (12)	0.3315 (5)	0.0924 (11)
H20A	0.2849	0.4346	0.2318	0.139*
H20B	0.3676	0.4803	0.3116	0.139*
H20C	0.2837	0.4445	0.4335	0.139*
N2	0.5871 (2)	0.29262 (8)	0.4446 (3)	0.0582 (6)
H2N	0.4967	0.2821	0.4198	0.07*
O2	0.8109 (2)	0.27020 (8)	0.5515 (3)	0.0881 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0605 (19)	0.0674 (19)	0.076 (2)	0.0005 (15)	−0.0193 (15)	−0.0054 (15)
C2	0.0450 (18)	0.0666 (19)	0.0580 (18)	0.0047 (15)	−0.0150 (13)	−0.0017 (14)
C3	0.0402 (16)	0.0650 (19)	0.0497 (16)	0.0012 (14)	−0.0127 (12)	0.0051 (13)
C4	0.0363 (15)	0.0679 (19)	0.0617 (17)	0.0008 (13)	−0.0081 (12)	0.0058 (14)
C5	0.0473 (17)	0.071 (2)	0.0624 (18)	−0.0075 (15)	−0.0144 (13)	0.0086 (15)
C6	0.0603 (19)	0.0638 (19)	0.070 (2)	−0.0034 (16)	−0.0170 (15)	0.0000 (15)
C7	0.0484 (18)	0.071 (2)	0.0676 (19)	0.0063 (15)	−0.0132 (14)	0.0010 (15)
C8	0.0393 (16)	0.070 (2)	0.0639 (18)	−0.0022 (14)	−0.0156 (13)	0.0031 (14)
C9	0.0557 (19)	0.086 (2)	0.099 (2)	−0.0193 (17)	−0.0199 (17)	0.0031 (18)
C10	0.066 (2)	0.088 (2)	0.113 (3)	0.0159 (19)	−0.0173 (19)	−0.019 (2)
O1	0.0508 (13)	0.0751 (15)	0.1202 (18)	0.0053 (10)	−0.0443 (12)	0.0007 (12)
N1	0.0388 (13)	0.0666 (15)	0.0665 (15)	−0.0002 (12)	−0.0235 (10)	0.0009 (12)
C11	0.062 (2)	0.069 (2)	0.0695 (18)	0.0019 (16)	−0.0153 (15)	0.0027 (15)
C12	0.0457 (18)	0.072 (2)	0.0519 (17)	0.0032 (15)	−0.0154 (13)	−0.0010 (14)
C13	0.0362 (15)	0.0675 (18)	0.0522 (16)	−0.0022 (14)	−0.0114 (12)	−0.0044 (13)
C14	0.0398 (16)	0.079 (2)	0.0622 (18)	−0.0015 (14)	−0.0139 (13)	0.0002 (14)
C15	0.0537 (18)	0.071 (2)	0.0650 (19)	−0.0126 (16)	−0.0125 (14)	0.0045 (15)
C16	0.062 (2)	0.0641 (19)	0.071 (2)	−0.0038 (16)	−0.0116 (16)	0.0013 (15)
C17	0.0486 (18)	0.070 (2)	0.0643 (19)	0.0029 (15)	−0.0119 (14)	−0.0073 (15)
C18	0.0393 (16)	0.0691 (19)	0.0648 (18)	−0.0050 (14)	−0.0124 (13)	−0.0065 (14)
C19	0.062 (2)	0.098 (3)	0.111 (3)	−0.0287 (19)	−0.0228 (18)	0.022 (2)
C20	0.065 (2)	0.088 (2)	0.121 (3)	0.0169 (19)	−0.0273 (19)	0.000 (2)
N2	0.0366 (13)	0.0624 (15)	0.0735 (15)	−0.0044 (11)	−0.0189 (11)	−0.0011 (12)
O2	0.0526 (14)	0.0954 (16)	0.1113 (17)	−0.0062 (12)	−0.0497 (12)	0.0078 (12)

Geometric parameters (Å, º) top

C1—C2	1.483 (4)	C11—C12	1.484 (4)
C1—H1A	0.96	C11—H11A	0.96
C1—H1B	0.96	C11—H11B	0.96
C1—H1C	0.96	C11—H11C	0.96
C2—O1	1.178 (3)	C12—O2	1.189 (3)
C2—N1	1.335 (3)	C12—N2	1.325 (3)
C3—C4	1.377 (3)	C13—C18	1.377 (3)
C3—C8	1.399 (3)	C13—C14	1.390 (3)
C3—N1	1.401 (3)	C13—N2	1.407 (3)
C4—C5	1.375 (4)	C14—C15	1.379 (4)
C4—H4	0.93	C14—H14	0.93
C5—C6	1.401 (4)	C15—C16	1.371 (4)
C5—C9	1.496 (4)	C15—C19	1.517 (4)
C6—C7	1.374 (4)	C16—C17	1.389 (4)
C6—H6	0.93	C16—H16	0.93
C7—C8	1.371 (4)	C17—C18	1.375 (4)
C7—C10	1.519 (4)	C17—C20	1.485 (4)
C8—H8	0.93	C18—H18	0.93
C9—H9A	0.96	C19—H19A	0.96
C9—H9B	0.96	C19—H19B	0.96
C9—H9C	0.96	C19—H19C	0.96
C10—H10A	0.96	C20—H20A	0.96
C10—H10B	0.96	C20—H20B	0.96
C10—H10C	0.96	C20—H20C	0.96
N1—H1N	0.86	N2—H2N	0.86

C2—C1—H1A	109.5	C12—C11—H11A	109.5
C2—C1—H1B	109.5	C12—C11—H11B	109.5
H1A—C1—H1B	109.5	H11A—C11—H11B	109.5
C2—C1—H1C	109.5	C12—C11—H11C	109.5
H1A—C1—H1C	109.5	H11A—C11—H11C	109.5
H1B—C1—H1C	109.5	H11B—C11—H11C	109.5
O1—C2—N1	121.4 (3)	O2—C12—N2	120.7 (3)
O1—C2—C1	121.2 (3)	O2—C12—C11	122.7 (3)
N1—C2—C1	117.3 (2)	N2—C12—C11	116.6 (2)
C4—C3—C8	119.5 (3)	C18—C13—C14	118.1 (3)
C4—C3—N1	121.8 (2)	C18—C13—N2	117.1 (2)
C8—C3—N1	118.7 (2)	C14—C13—N2	124.7 (2)
C5—C4—C3	119.0 (3)	C15—C14—C13	121.8 (3)
C5—C4—H4	120.5	C15—C14—H14	119.1
C3—C4—H4	120.5	C13—C14—H14	119.1
C4—C5—C6	120.1 (3)	C16—C15—C14	118.6 (3)
C4—C5—C9	118.6 (3)	C16—C15—C19	120.8 (3)
C6—C5—C9	121.2 (3)	C14—C15—C19	120.5 (3)
C7—C6—C5	121.8 (3)	C15—C16—C17	121.0 (3)
C7—C6—H6	119.1	C15—C16—H16	119.5
C5—C6—H6	119.1	C17—C16—H16	119.5
C8—C7—C6	116.9 (3)	C18—C17—C16	119.2 (3)
C8—C7—C10	121.1 (3)	C18—C17—C20	119.7 (3)
C6—C7—C10	122.0 (3)	C16—C17—C20	121.1 (3)
C7—C8—C3	122.6 (3)	C17—C18—C13	121.3 (3)
C7—C8—H8	118.7	C17—C18—H18	119.4
C3—C8—H8	118.7	C13—C18—H18	119.4
C5—C9—H9A	109.5	C15—C19—H19A	109.5
C5—C9—H9B	109.5	C15—C19—H19B	109.5
H9A—C9—H9B	109.5	H19A—C19—H19B	109.5
C5—C9—H9C	109.5	C15—C19—H19C	109.5
H9A—C9—H9C	109.5	H19A—C19—H19C	109.5
H9B—C9—H9C	109.5	H19B—C19—H19C	109.5
C7—C10—H10A	109.5	C17—C20—H20A	109.5
C7—C10—H10B	109.5	C17—C20—H20B	109.5
H10A—C10—H10B	109.5	H20A—C20—H20B	109.5
C7—C10—H10C	109.5	C17—C20—H20C	109.5
H10A—C10—H10C	109.5	H20A—C20—H20C	109.5
H10B—C10—H10C	109.5	H20B—C20—H20C	109.5
C2—N1—C3	130.0 (2)	C12—N2—C13	130.3 (2)
C2—N1—H1N	115	C12—N2—H2N	114.9
C3—N1—H1N	115	C13—N2—H2N	114.9

C8—C3—C4—C5	1.1 (4)	C18—C13—C14—C15	−1.1 (4)
N1—C3—C4—C5	−178.0 (2)	N2—C13—C14—C15	176.3 (2)
C3—C4—C5—C6	0.1 (4)	C13—C14—C15—C16	1.7 (4)
C3—C4—C5—C9	179.4 (2)	C13—C14—C15—C19	−178.3 (3)
C4—C5—C6—C7	−1.1 (4)	C14—C15—C16—C17	−1.0 (4)
C9—C5—C6—C7	179.6 (3)	C19—C15—C16—C17	179.0 (3)
C5—C6—C7—C8	0.8 (4)	C15—C16—C17—C18	−0.3 (4)
C5—C6—C7—C10	−179.6 (3)	C15—C16—C17—C20	179.2 (3)
C6—C7—C8—C3	0.5 (4)	C16—C17—C18—C13	0.9 (4)
C10—C7—C8—C3	−179.1 (3)	C20—C17—C18—C13	−178.5 (3)
C4—C3—C8—C7	−1.4 (4)	C14—C13—C18—C17	−0.3 (4)
N1—C3—C8—C7	177.7 (2)	N2—C13—C18—C17	−177.8 (2)
O1—C2—N1—C3	−5.6 (5)	O2—C12—N2—C13	5.9 (4)
C1—C2—N1—C3	172.5 (2)	C11—C12—N2—C13	−172.9 (2)
C4—C3—N1—C2	26.9 (4)	C18—C13—N2—C12	−168.5 (3)
C8—C3—N1—C2	−152.1 (3)	C14—C13—N2—C12	14.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4···O1	0.93	2.36	2.865 (4)	114
N1—H1N···O2ⁱ	0.86	1.96	2.812 (3)	174
C14—H14···O2	0.93	2.33	2.886 (4)	118
N2—H2N···O1ⁱⁱ	0.86	1.96	2.810 (3)	167

Symmetry codes: (i) x−1, y, z; (ii) x, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₀H₁₃NO
M_r	163.21
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	295
a, b, c (Å)	8.7925 (12), 27.690 (5), 7.6525 (15)
β (°)	92.65 (1)
V (Å³)	1861.1 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.31 × 0.26 × 0.08

Data collection
Diffractometer	Xcalibur System, Oxford Diffraction, Ltd.
Absorption correction	Analytical (Clark & Reid, 1995)
T_min, T_max	0.965, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	17320, 3638, 1750
R_int	0.076
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.066, 0.175, 0.99
No. of reflections	3638
No. of parameters	231
No. of restraints	56
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.15

Computer programs: CrysAlis CCD (Oxford Diffraction, 2007), CrysAlis RED (Oxford Diffraction, 2007), CrysAlis RED, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), SHELXL97, PLATON (Spek, 2003) and WinGX (Farrugia, 1999).