N,4-Dimethyl-benzamide.

In the crystal of the title compound, C(9)H(11)NO, mol-ecules are connected via inter-molecular 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 = 149.19

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.050

wR(F 2) = 0.166

S = 1.01

1510 reflections

103 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.15 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 datablocks I, global. DOI: 10.1107/S1600536811003527/vm2076sup1.cif

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

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

C9H11NO	F(000) = 320
Mr = 149.19	Dx = 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

Enraf–Nonius CAD-4 diffractometer	1062 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 25.4°, θmin = 2.6°
ω/2θ scans	h = 0→8
Absorption correction: ψ scan (North et al., 1968)	k = −11→11
Tmin = 0.977, Tmax = 0.992	l = −14→14
3362 measured reflections	3 standard reflections every 200 reflections
1510 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)] = 0.050	H-atom parameters constrained
wR(F2) = 0.166	w = 1/[σ2(Fo2) + (0.1P)2 + 0.080P] where P = (Fo2 + 2Fc2)/3
S = 1.01	(Δ/σ)max < 0.001
1510 reflections	Δρmax = 0.20 e Å−3
103 parameters	Δρmin = −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)

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
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*

	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)

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)

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

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) .