4-Meth-oxy-N-methyl-benzamide.

In the title compound, C(9)H(11)NO(2), the dihedral angle between the amide group and the benzene ring is 10.6 (1)°. In the crystal, mol-ecules 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 inter-actions 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 = 165.19

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.052

wR(F 2) = 0.169

S = 1.00

1573 reflections

110 parameters

H-atom parameters constrained

Δρmax = 0.18 e Å−3

Δρmin = −0.19 e Å−3

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.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812004746/sj5190sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812004746/sj5190Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C9H11NO2	F(000) = 352
Mr = 165.19	Dx = 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

Enraf–Nonius CAD-4 diffractometer	1088 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.042
Graphite monochromator	θmax = 25.4°, θmin = 2.4°
ω/2θ scans	h = 0→10
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.973, Tmax = 0.991	l = −12→12
3239 measured reflections	3 standard reflections every 200 reflections
1573 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)] = 0.052	H-atom parameters constrained
wR(F2) = 0.169	w = 1/[σ2(Fo2) + (0.1P)2 + 0.095P] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
1573 reflections	Δρmax = 0.18 e Å−3
110 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) ; (ii) .