N,4-Dimethyl­benzamide

Xu, J.-Y.; Cheng, W.-H.

doi:10.1107/S1600536811003527

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Page o557

doi:10.1107/S1600536811003527

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N,4-Dimethylbenzamide

Jia-Ying Xu ^a ^* and Wei-Hua Cheng ^b

^aCollege of Chemical and Biological Engineering, Yancheng Institute of Technology, Yinbing Road No. 9 Yancheng, Yancheng 224051, People's Republic of China, and ^bDepartment of Chemical Engineering, Yancheng College of Textile Technology, Yancheng 224051, People's Republic of China
^*Correspondence e-mail: xujiaying-1984@163.com

(Received 20 January 2011; accepted 27 January 2011; online 5 February 2011)

In the crystal of the title compound, C₉H₁₁NO, molecules are connected via intermolecular N—H⋯O hydrogen bonds, forming a one-dimensional network in the b-axis direction. The dihedral angle between the amide group and the benzyl ring is 13.8 (2)°.

Related literature

For the synthetic procedure, see: Lee et al. (2009 ). For bond-length data, see: Allen et al. (1987 ). ?show [softreturn]>

Experimental

Crystal data

C₉H₁₁NO
M_r = 149.19
Monoclinic, P 2₁ /n
a = 6.7670 (14) Å
b = 9.946 (2) Å
c = 12.229 (2) Å
β = 92.63 (3)°
V = 822.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.977, T_max = 0.992
3362 measured reflections
1510 independent reflections
1062 reflections with I > 2σ(I)
R_int = 0.033
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.166
S = 1.01
1510 reflections
103 parameters
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯Oⁱ	0.86	2.10	2.912 (2)	158
Symmetry code: (i) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo,1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811003527/vm2076sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811003527/vm2076Isup2.hkl

checkCIF report

Comment top

Benzamide derivatives exhibit interesting biological activities such as antibacterial and antifungal effects (Lee et al., 2009) We report here the crystal structure of the title compound N,4-dimethylbenzamide (I), an important organic intermediate (Fig. 1). Bond lengths and angles are within normal ranges (Allen et al., 1987).

In the crystal packing of (I) the molecules are connected together via N—H···O intermolecular hydrogen bonds to form a one-dimensional network in the b direction (Table 1, graph set C1,1(4)), which seems to be very effective in the stabilization of the crystal structure.

Related literature top

For the synthetic procedure, see: Lee et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by a method reported in literature (Lee et al. (2009)). Crystals were obtained by dissolving (I) (0.2 g, 1.34 mmol) in ethanol (25 ml) and evaporating the solvent slowly at room temperature for about 7 d.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo,1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Packing diagram for (I) showing the N—H···O hydrogen bonds as dashed lines.

N,4-Dimethylbenzamide top

Crystal data top

C₉H₁₁NO	F(000) = 320
M_r = 149.19	D_x = 1.205 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 25 reflections
a = 6.7670 (14) Å	θ = 9–13°
b = 9.946 (2) Å	µ = 0.08 mm⁻¹
c = 12.229 (2) Å	T = 293 K
β = 92.63 (3)°	Block, colourless
V = 822.2 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.4°, θ_min = 2.6°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.977, T_max = 0.992	l = −14→14
3362 measured reflections	3 standard reflections every 200 reflections
1510 independent reflections	intensity decay: 1%

Refinement top

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)] = 0.050	H-atom parameters constrained
wR(F²) = 0.166	w = 1/[σ²(F_o²) + (0.1P)² + 0.080P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max < 0.001
1510 reflections	Δρ_max = 0.20 e Å⁻³
103 parameters	Δρ_min = −0.15 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (8)

Crystal data top

C₉H₁₁NO	V = 822.2 (3) Å³
M_r = 149.19	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 6.7670 (14) Å	µ = 0.08 mm⁻¹
b = 9.946 (2) Å	T = 293 K
c = 12.229 (2) Å	0.30 × 0.20 × 0.10 mm
β = 92.63 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1062 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.033
T_min = 0.977, T_max = 0.992	3 standard reflections every 200 reflections
3362 measured reflections	intensity decay: 1%
1510 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.166	H-atom parameters constrained
S = 1.01	Δρ_max = 0.20 e Å⁻³
1510 reflections	Δρ_min = −0.15 e Å⁻³
103 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
O	0.2041 (3)	0.99892 (14)	0.23558 (16)	0.0773 (6)
N	0.2849 (2)	0.78998 (15)	0.28900 (14)	0.0514 (5)
H0A	0.2554	0.7059	0.2868	0.062*
C1	−0.5644 (4)	0.6995 (3)	0.0146 (2)	0.0766 (8)
H1A	−0.6295	0.6353	0.0592	0.115*
H1B	−0.5367	0.6591	−0.0543	0.115*
H1C	−0.6485	0.7763	0.0023	0.115*
C2	−0.3742 (3)	0.7431 (2)	0.07191 (17)	0.0550 (6)
C3	−0.2949 (4)	0.8698 (2)	0.05499 (19)	0.0652 (7)
H3A	−0.3599	0.9283	0.0062	0.078*
C4	−0.1226 (3)	0.9106 (2)	0.10867 (18)	0.0591 (6)
H4A	−0.0750	0.9968	0.0969	0.071*
C5	−0.0184 (3)	0.82556 (17)	0.18015 (15)	0.0440 (5)
C6	−0.0961 (3)	0.69834 (18)	0.19627 (17)	0.0530 (6)
H6A	−0.0291	0.6387	0.2434	0.064*
C7	−0.2701 (3)	0.6593 (2)	0.14374 (18)	0.0581 (6)
H7A	−0.3195	0.5738	0.1569	0.070*
C8	0.1657 (3)	0.87739 (18)	0.23661 (16)	0.0479 (5)
C9	0.4623 (3)	0.8321 (2)	0.3494 (2)	0.0613 (6)
H9A	0.5168	0.7575	0.3904	0.092*
H9B	0.4309	0.9034	0.3987	0.092*
H9C	0.5571	0.8637	0.2993	0.092*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O	0.0747 (11)	0.0273 (8)	0.1272 (15)	−0.0054 (7)	−0.0245 (10)	0.0023 (8)
N	0.0498 (10)	0.0296 (8)	0.0737 (12)	−0.0025 (7)	−0.0084 (8)	−0.0006 (7)
C1	0.0590 (15)	0.0951 (19)	0.0743 (16)	−0.0004 (13)	−0.0132 (12)	−0.0086 (14)
C2	0.0481 (12)	0.0610 (13)	0.0555 (12)	0.0047 (10)	−0.0017 (10)	−0.0086 (10)
C3	0.0654 (15)	0.0563 (13)	0.0721 (15)	0.0125 (11)	−0.0159 (12)	0.0065 (11)
C4	0.0631 (14)	0.0396 (11)	0.0739 (14)	0.0040 (10)	−0.0038 (12)	0.0083 (10)
C5	0.0446 (11)	0.0321 (9)	0.0552 (11)	0.0050 (8)	0.0007 (9)	−0.0030 (8)
C6	0.0531 (12)	0.0351 (10)	0.0695 (13)	0.0000 (9)	−0.0108 (10)	0.0047 (9)
C7	0.0547 (13)	0.0463 (12)	0.0724 (14)	−0.0055 (9)	−0.0068 (11)	−0.0010 (10)
C8	0.0503 (12)	0.0288 (9)	0.0647 (12)	0.0016 (8)	0.0017 (9)	−0.0024 (8)
C9	0.0537 (13)	0.0506 (12)	0.0783 (15)	−0.0037 (10)	−0.0122 (11)	−0.0019 (11)

Geometric parameters (Å, º) top

O—C8	1.237 (2)	C3—H3A	0.9300
N—C8	1.330 (2)	C4—C5	1.386 (3)
N—C9	1.442 (3)	C4—H4A	0.9300
N—H0A	0.8600	C5—C6	1.388 (3)
C1—C2	1.501 (3)	C5—C8	1.489 (3)
C1—H1A	0.9600	C6—C7	1.372 (3)
C1—H1B	0.9600	C6—H6A	0.9300
C1—H1C	0.9600	C7—H7A	0.9300
C2—C7	1.381 (3)	C9—H9A	0.9600
C2—C3	1.389 (3)	C9—H9B	0.9600
C3—C4	1.373 (3)	C9—H9C	0.9600

C8—N—C9	121.90 (17)	C4—C5—C6	117.46 (19)
C8—N—H0A	119.0	C4—C5—C8	118.17 (17)
C9—N—H0A	119.0	C6—C5—C8	124.35 (17)
C2—C1—H1A	109.5	C7—C6—C5	120.96 (19)
C2—C1—H1B	109.5	C7—C6—H6A	119.5
H1A—C1—H1B	109.5	C5—C6—H6A	119.5
C2—C1—H1C	109.5	C6—C7—C2	121.9 (2)
H1A—C1—H1C	109.5	C6—C7—H7A	119.0
H1B—C1—H1C	109.5	C2—C7—H7A	119.0
C7—C2—C3	117.0 (2)	O—C8—N	121.39 (19)
C7—C2—C1	121.6 (2)	O—C8—C5	120.36 (18)
C3—C2—C1	121.4 (2)	N—C8—C5	118.24 (16)
C4—C3—C2	121.5 (2)	N—C9—H9A	109.5
C4—C3—H3A	119.2	N—C9—H9B	109.5
C2—C3—H3A	119.2	H9A—C9—H9B	109.5
C3—C4—C5	121.2 (2)	N—C9—H9C	109.5
C3—C4—H4A	119.4	H9A—C9—H9C	109.5
C5—C4—H4A	119.4	H9B—C9—H9C	109.5

C7—C2—C3—C4	−1.1 (3)	C3—C2—C7—C6	−0.1 (3)
C1—C2—C3—C4	178.9 (2)	C1—C2—C7—C6	179.9 (2)
C2—C3—C4—C5	1.5 (4)	C9—N—C8—O	1.5 (3)
C3—C4—C5—C6	−0.7 (3)	C9—N—C8—C5	−177.53 (18)
C3—C4—C5—C8	−179.17 (19)	C4—C5—C8—O	13.1 (3)
C4—C5—C6—C7	−0.4 (3)	C6—C5—C8—O	−165.2 (2)
C8—C5—C6—C7	177.91 (18)	C4—C5—C8—N	−167.81 (18)
C5—C6—C7—C2	0.8 (3)	C6—C5—C8—N	13.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	2.10	2.912 (2)	158

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₉H₁₁NO
M_r	149.19
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	6.7670 (14), 9.946 (2), 12.229 (2)
β (°)	92.63 (3)
V (Å³)	822.2 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.977, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	3362, 1510, 1062
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.166, 1.01
No. of reflections	1510
No. of parameters	103
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.15

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo,1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···Oⁱ	0.86	2.10	2.912 (2)	158

Symmetry code: (i) −x+1/2, y−1/2, −z+1/2.

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Lee, S., Song, K. H., Choe, J., Ju, J. & Jo, Y. (2009). J. Org. Chem. 74, 6358–6361. Web of Science PubMed Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar