4-Meth­oxy-N-methyl­benzamide

Yuan, J.; Liu, Y.-J.

doi:10.1107/S1600536812004746

organic compounds

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Volume 68| Part 3| March 2012| Page o647

doi:10.1107/S1600536812004746

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4-Methoxy-N-methylbenzamide

Juan Yuan ^a and Yan-Ju Liu ^a ^*

^aPharmacy College, Henan University of Traditional Chinese Medicine, Zhengzhou 450008, People's Republic of China
^*Correspondence e-mail: liuyanju886@163.com

(Received 29 January 2012; accepted 3 February 2012; online 10 February 2012)

In the title compound, C₉H₁₁NO₂, the dihedral angle between the amide group and the benzene ring is 10.6 (1)°. In the crystal, molecules are connected via N—H⋯O hydrogen bonds, supported by a C—H⋯O contact, forming chains along b. These chains are linked by C—H⋯π interactions to give a three-dimensional network.

Related literature

The title compound is an important intermediate in organic synthesis. For background to applications of the title compound and the synthesis, see: Lee et al. (2009 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₉H₁₁NO₂
M_r = 165.19
Monoclinic, P 2₁ /c
a = 8.7350 (17) Å
b = 9.2750 (19) Å
c = 10.719 (2) Å
β = 99.83 (3)°
V = 855.7 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.09 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 = 0.973, T_max = 0.991
3239 measured reflections
1573 independent reflections
1088 reflections with I > 2σ(I)
R_int = 0.042
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.169
S = 1.00
1573 reflections
110 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.19 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C1–C6 benzene ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O2ⁱ	0.86	2.20	2.961 (2)	147
C1—H1A⋯O2ⁱ	0.93	2.46	3.378 (3)	169
C7—H7C⋯Cg1ⁱⁱ	0.96	2.94	3.816 (3)	153
Symmetry codes: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x, -y-{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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/S1600536812004746/sj5190sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812004746/sj5190Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812004746/sj5190Isup3.cml

checkCIF report

Comment top

Benzamide derivatives exhibit interesting biological activities including antibacterial and antifungal effects (Lee et al., 2009). We report here the crystal structure of the title compound 4-methoxy-N-methylbenzamide, (I).

The molecular structure of (I) is shown in Fig. 1. The dihedral angle between the amide group and the benzene ring is 10.6 (1)°. The bond lengths are within normal ranges (Allen et al., 1987). In the crystal structure, intermolecular N—H0A···O2 hydrogen bonds, supported by C1—H1···O1 contacts (Table 1) result in the molecular chains along b. These chains are linked by C7—H7···π interactions to give a three-dimensional network.

Related literature top

The title compound is an important intermediate in organic synthesis. For background to applications of the title compound and the synthesis, see: Lee et al. (2009). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound, (I) was prepared by a literature method (Lee et al., 2009). Crystals were obtained by dissolving (I) (0.2 g) in methanol (50 ml) and evaporating the solvent slowly at room temperature for about 10 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. A packing diagram of (I).

4-Methoxy-N-methylbenzamide top

Crystal data top

C₉H₁₁NO₂	F(000) = 352
M_r = 165.19	D_x = 1.282 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.7350 (17) Å	θ = 10–14°
b = 9.2750 (19) Å	µ = 0.09 mm⁻¹
c = 10.719 (2) Å	T = 293 K
β = 99.83 (3)°	Block, colourless
V = 855.7 (3) Å³	0.30 × 0.20 × 0.10 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1088 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.042
Graphite monochromator	θ_max = 25.4°, θ_min = 2.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
T_min = 0.973, T_max = 0.991	l = −12→12
3239 measured reflections	3 standard reflections every 200 reflections
1573 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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.169	w = 1/[σ²(F_o²) + (0.1P)² + 0.095P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
1573 reflections	Δρ_max = 0.18 e Å⁻³
110 parameters	Δρ_min = −0.19 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: 0.25 (2)

Crystal data top

C₉H₁₁NO₂	V = 855.7 (3) Å³
M_r = 165.19	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.7350 (17) Å	µ = 0.09 mm⁻¹
b = 9.2750 (19) Å	T = 293 K
c = 10.719 (2) Å	0.30 × 0.20 × 0.10 mm
β = 99.83 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1088 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.042
T_min = 0.973, T_max = 0.991	3 standard reflections every 200 reflections
3239 measured reflections	intensity decay: 1%
1573 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.169	H-atom parameters constrained
S = 1.00	Δρ_max = 0.18 e Å⁻³
1573 reflections	Δρ_min = −0.19 e Å⁻³
110 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
N	−0.0727 (2)	0.35158 (19)	0.24974 (17)	0.0581 (6)
H0A	−0.0375	0.4382	0.2598	0.070*
O1	0.4704 (2)	0.42231 (19)	0.72531 (15)	0.0746 (6)
C1	0.1914 (3)	0.4288 (2)	0.4363 (2)	0.0641 (7)
H1A	0.1610	0.4937	0.3706	0.077*
O2	−0.0596 (2)	0.12586 (17)	0.32506 (15)	0.0701 (6)
C2	0.3083 (3)	0.4659 (2)	0.5335 (2)	0.0701 (8)
H2A	0.3569	0.5550	0.5321	0.084*
C3	0.3548 (3)	0.3727 (2)	0.63338 (19)	0.0544 (6)
C4	0.2849 (3)	0.2390 (3)	0.63200 (19)	0.0564 (6)
H4A	0.3161	0.1740	0.6975	0.068*
C5	0.1686 (3)	0.2022 (2)	0.5331 (2)	0.0532 (6)
H5A	0.1229	0.1116	0.5328	0.064*
C6	0.1180 (2)	0.2963 (2)	0.43448 (19)	0.0474 (6)
C7	0.5133 (3)	0.3375 (3)	0.8361 (2)	0.0813 (9)
H7A	0.5957	0.3847	0.8921	0.122*
H7B	0.5481	0.2445	0.8131	0.122*
H7C	0.4253	0.3260	0.8779	0.122*
C8	−0.0109 (2)	0.2511 (2)	0.33215 (18)	0.0497 (6)
C9	−0.1962 (3)	0.3222 (3)	0.1440 (2)	0.0700 (8)
H9A	−0.2229	0.4094	0.0970	0.105*
H9B	−0.2857	0.2867	0.1753	0.105*
H9C	−0.1618	0.2512	0.0898	0.105*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N	0.0653 (12)	0.0475 (10)	0.0548 (11)	−0.0002 (9)	−0.0089 (9)	−0.0047 (8)
O1	0.0820 (12)	0.0739 (11)	0.0562 (10)	−0.0104 (9)	−0.0210 (9)	0.0078 (8)
C1	0.0857 (17)	0.0445 (12)	0.0520 (13)	−0.0056 (12)	−0.0170 (12)	0.0065 (10)
O2	0.0913 (13)	0.0485 (9)	0.0628 (10)	−0.0150 (8)	−0.0085 (9)	−0.0023 (7)
C2	0.0898 (18)	0.0466 (12)	0.0629 (14)	−0.0129 (12)	−0.0185 (13)	0.0059 (10)
C3	0.0585 (13)	0.0559 (13)	0.0445 (11)	0.0014 (10)	−0.0034 (10)	−0.0015 (10)
C4	0.0685 (14)	0.0558 (13)	0.0429 (11)	0.0057 (11)	0.0045 (10)	0.0115 (10)
C5	0.0644 (14)	0.0459 (11)	0.0483 (12)	−0.0041 (10)	0.0065 (10)	0.0011 (9)
C6	0.0575 (12)	0.0411 (11)	0.0427 (11)	0.0032 (9)	0.0058 (9)	−0.0017 (8)
C7	0.0776 (17)	0.106 (2)	0.0522 (14)	−0.0006 (16)	−0.0108 (13)	0.0132 (14)
C8	0.0593 (13)	0.0460 (12)	0.0427 (11)	0.0008 (10)	0.0058 (9)	−0.0059 (9)
C9	0.0688 (15)	0.0703 (16)	0.0630 (16)	−0.0017 (12)	−0.0117 (13)	−0.0018 (12)

Geometric parameters (Å, º) top

N—C8	1.333 (3)	C4—C5	1.380 (3)
N—C9	1.451 (3)	C4—H4A	0.9300
N—H0A	0.8600	C5—C6	1.384 (3)
O1—C3	1.365 (3)	C5—H5A	0.9300
O1—C7	1.420 (3)	C6—C8	1.492 (3)
C1—C2	1.372 (3)	C7—H7A	0.9600
C1—C6	1.385 (3)	C7—H7B	0.9600
C1—H1A	0.9300	C7—H7C	0.9600
O2—C8	1.235 (3)	C9—H9A	0.9600
C2—C3	1.383 (3)	C9—H9B	0.9600
C2—H2A	0.9300	C9—H9C	0.9600
C3—C4	1.381 (3)

C8—N—C9	123.30 (19)	C5—C6—C1	117.52 (19)
C8—N—H0A	118.3	C5—C6—C8	119.12 (19)
C9—N—H0A	118.3	C1—C6—C8	123.36 (19)
C3—O1—C7	118.3 (2)	O1—C7—H7A	109.5
C2—C1—C6	121.1 (2)	O1—C7—H7B	109.5
C2—C1—H1A	119.5	H7A—C7—H7B	109.5
C6—C1—H1A	119.5	O1—C7—H7C	109.5
C1—C2—C3	120.9 (2)	H7A—C7—H7C	109.5
C1—C2—H2A	119.6	H7B—C7—H7C	109.5
C3—C2—H2A	119.6	O2—C8—N	121.38 (19)
O1—C3—C4	125.57 (19)	O2—C8—C6	121.26 (19)
O1—C3—C2	115.6 (2)	N—C8—C6	117.36 (18)
C4—C3—C2	118.86 (19)	N—C9—H9A	109.5
C5—C4—C3	119.8 (2)	N—C9—H9B	109.5
C5—C4—H4A	120.1	H9A—C9—H9B	109.5
C3—C4—H4A	120.1	N—C9—H9C	109.5
C4—C5—C6	121.9 (2)	H9A—C9—H9C	109.5
C4—C5—H5A	119.1	H9B—C9—H9C	109.5
C6—C5—H5A	119.1

C6—C1—C2—C3	−0.9 (4)	C4—C5—C6—C8	−178.5 (2)
C7—O1—C3—C4	−6.9 (4)	C2—C1—C6—C5	−1.0 (4)
C7—O1—C3—C2	174.2 (2)	C2—C1—C6—C8	179.2 (2)
C1—C2—C3—O1	−179.0 (2)	C9—N—C8—O2	−2.2 (3)
C1—C2—C3—C4	2.0 (4)	C9—N—C8—C6	178.6 (2)
O1—C3—C4—C5	179.8 (2)	C5—C6—C8—O2	−9.3 (3)
C2—C3—C4—C5	−1.4 (3)	C1—C6—C8—O2	170.5 (2)
C3—C4—C5—C6	−0.5 (3)	C5—C6—C8—N	169.8 (2)
C4—C5—C6—C1	1.7 (3)	C1—C6—C8—N	−10.4 (3)

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.20	2.961 (2)	147
C1—H1A···O2ⁱ	0.93	2.46	3.378 (3)	169
C7—H7C···Cg1ⁱⁱ	0.96	2.94	3.816 (3)	153

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

Experimental details

Crystal data
Chemical formula	C₉H₁₁NO₂
M_r	165.19
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.7350 (17), 9.2750 (19), 10.719 (2)
β (°)	99.83 (3)
V (Å³)	855.7 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
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	0.973, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	3239, 1573, 1088
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.169, 1.00
No. of reflections	1573
No. of parameters	110
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.19

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

Cg1 is the centroid of the C1–C6 benzene ring.

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O2ⁱ	0.86	2.20	2.961 (2)	147
C1—H1A···O2ⁱ	0.93	2.46	3.378 (3)	169
C7—H7C···Cg1ⁱⁱ	0.96	2.94	3.816 (3)	153

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

Acknowledgements

This study was supported by the Science and Technology Department of Henan Province (grant No. 102102310321) and the Doctoral Research Fund of Henan Chinese Medicine (grant No. BSJJ2009-38). 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

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CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 3| March 2012| Page o647

doi:10.1107/S1600536812004746

Open

access