N-(3,5-Dimeth-oxy-phen-yl)benzamide.

The title compound, C(15)H(15)NO(3), was prepared by stirring benzoyl chloride with 3,5-dimeth-oxy-aniline in dioxane at ambient temperature. The dimeth-oxy-phen-yl-amide segment of the mol-ecule is almost planar, with a C-N-C=O torsion angle of -4.1 (4)°. The two benzene rings are inclined at an angle of 76.66 (13)°. In the crystal, inter-molecular N-H⋯O inter-actions generate centrosymmetric dimers..

Related literature

For related structures, see: Faler & Joullie (2006 ▶); Hadjeri et al. (2002 ▶); Beney et al. (2000 ▶). For bond lengths and angles in related structures, see: Saeed et al. (2010 ▶); Wang et al. (2010 ▶); Anderson et al. (2005 ▶).

Experimental

Crystal data

C15H15NO3

M = 257.28

Monoclinic,

a = 8.0390 (16) Å

b = 20.003 (4) Å

c = 9.2710 (19) Å

β = 111.39 (3)°

V = 1388.1 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.30 × 0.30 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968) ▶ T min = 0.975, T max = 0.991

2737 measured reflections

2550 independent reflections

1564 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)] = 0.054

wR(F 2) = 0.165

S = 1.00

2550 reflections

173 parameters

H-atom parameters constrained

Δρmax = 0.17 e Å−3

Δρmin = −0.19 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ▶); cell refinement: CAD-4 EXPRESS; 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: publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536811019350/zj2010sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536811019350/zj2010Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536811019350/zj2010Isup3.cml

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

C15H15NO3	F(000) = 544
Mr = 257.28	Dx = 1.231 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 8.0390 (16) Å	θ = 9–13°
b = 20.003 (4) Å	µ = 0.09 mm−1
c = 9.2710 (19) Å	T = 293 K
β = 111.39 (3)°	Block, colourless
V = 1388.1 (5) Å3	0.30 × 0.30 × 0.10 mm
Z = 4

Enraf–Nonius CAD-4 diffractometer	1564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.033
graphite	θmax = 25.4°, θmin = 2.0°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→24
Tmin = 0.975, Tmax = 0.991	l = −11→10
2737 measured reflections	3 standard reflections every 200 reflections
2550 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)] = 0.054	H-atom parameters constrained
wR(F2) = 0.165	w = 1/[σ2(Fo2) + (0.093P)2] where P = (Fo2 + 2Fc2)/3
S = 1.00	(Δ/σ)max < 0.001
2550 reflections	Δρmax = 0.17 e Å−3
173 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: 0.037 (5)

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 F2are 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	0.3527 (3)	0.25056 (10)	0.78089 (19)	0.0513 (5)
H0A	0.3555	0.2581	0.8731	0.062*
O1	0.4214 (3)	0.01660 (9)	0.8098 (2)	0.0754 (6)
C1	0.8603 (5)	0.20349 (18)	0.5865 (5)	0.1074 (13)
H1A	0.9541	0.1959	0.5476	0.161*
H1B	0.9054	0.2297	0.6795	0.161*
H1C	0.7641	0.2271	0.5102	0.161*
O2	0.7975 (3)	0.14175 (11)	0.6190 (3)	0.0872 (7)
C2	0.5014 (5)	−0.04432 (14)	0.7878 (4)	0.0954 (11)
H2A	0.4455	−0.0813	0.8181	0.143*
H2B	0.6266	−0.0438	0.8498	0.143*
H2C	0.4859	−0.0488	0.6805	0.143*
O3	0.2596 (3)	0.28887 (9)	0.53489 (18)	0.0732 (6)
C3	0.3954 (3)	0.13183 (12)	0.7943 (2)	0.0505 (6)
H3A	0.3059	0.1283	0.8351	0.061*
C4	0.4817 (3)	0.07509 (12)	0.7710 (3)	0.0532 (6)
C5	0.6135 (3)	0.07981 (13)	0.7111 (3)	0.0576 (7)
H5A	0.6695	0.0415	0.6944	0.069*
C6	0.6628 (3)	0.14226 (14)	0.6757 (3)	0.0578 (7)
C7	0.5794 (3)	0.19976 (12)	0.6982 (2)	0.0533 (6)
H7A	0.6134	0.2416	0.6751	0.064*
C8	0.4436 (3)	0.19328 (12)	0.7564 (2)	0.0475 (6)
C9	0.2622 (3)	0.29379 (11)	0.6675 (2)	0.0472 (6)
C10	0.1626 (3)	0.34835 (11)	0.7090 (2)	0.0456 (6)
C11	0.0282 (4)	0.38045 (14)	0.5912 (3)	0.0674 (8)
H11A	−0.0003	0.3667	0.4892	0.081*
C12	−0.0632 (4)	0.43259 (16)	0.6242 (4)	0.0859 (10)
H12A	−0.1556	0.4531	0.5446	0.103*
C13	−0.0196 (4)	0.45452 (16)	0.7731 (3)	0.0824 (9)
H13A	−0.0789	0.4909	0.7943	0.099*
C14	0.1106 (4)	0.42291 (15)	0.8899 (3)	0.0762 (9)
H14A	0.1382	0.4371	0.9915	0.091*
C15	0.2022 (3)	0.37003 (12)	0.8593 (3)	0.0561 (7)
H15A	0.2913	0.3488	0.9403	0.067*

	U11	U22	U33	U12	U13	U23
N	0.0740 (13)	0.0518 (11)	0.0370 (9)	0.0088 (10)	0.0309 (9)	0.0003 (8)
O1	0.0848 (14)	0.0517 (11)	0.1028 (15)	0.0087 (10)	0.0497 (12)	0.0051 (10)
C1	0.093 (2)	0.108 (3)	0.152 (3)	−0.001 (2)	0.083 (2)	0.020 (2)
O2	0.0725 (13)	0.0954 (16)	0.1176 (18)	0.0032 (11)	0.0631 (13)	−0.0041 (13)
C2	0.106 (2)	0.0526 (18)	0.139 (3)	0.0147 (18)	0.059 (2)	−0.0014 (18)
O3	0.1181 (16)	0.0728 (13)	0.0434 (10)	0.0226 (11)	0.0468 (10)	0.0080 (8)
C3	0.0572 (14)	0.0549 (14)	0.0460 (13)	0.0036 (12)	0.0265 (11)	0.0021 (11)
C4	0.0544 (15)	0.0516 (15)	0.0547 (14)	0.0013 (12)	0.0212 (12)	0.0005 (11)
C5	0.0507 (14)	0.0616 (16)	0.0602 (15)	0.0077 (12)	0.0200 (12)	−0.0068 (12)
C6	0.0459 (14)	0.0732 (19)	0.0578 (15)	0.0014 (13)	0.0230 (12)	−0.0059 (13)
C7	0.0548 (15)	0.0582 (15)	0.0505 (13)	−0.0068 (12)	0.0233 (12)	−0.0044 (11)
C8	0.0543 (14)	0.0542 (14)	0.0359 (11)	0.0045 (11)	0.0186 (10)	−0.0026 (10)
C9	0.0627 (15)	0.0464 (13)	0.0406 (12)	−0.0052 (11)	0.0287 (11)	0.0011 (10)
C10	0.0527 (13)	0.0470 (13)	0.0419 (12)	−0.0042 (11)	0.0231 (11)	0.0015 (10)
C11	0.0783 (19)	0.0716 (17)	0.0452 (14)	0.0092 (15)	0.0138 (13)	−0.0006 (12)
C12	0.080 (2)	0.089 (2)	0.073 (2)	0.0328 (18)	0.0089 (16)	0.0047 (17)
C13	0.081 (2)	0.082 (2)	0.080 (2)	0.0323 (18)	0.0247 (17)	−0.0104 (16)
C14	0.083 (2)	0.090 (2)	0.0554 (16)	0.0262 (18)	0.0246 (15)	−0.0113 (15)
C15	0.0623 (16)	0.0633 (15)	0.0430 (13)	0.0122 (13)	0.0195 (12)	−0.0017 (11)

N—C9	1.350 (3)	C5—C6	1.386 (4)
N—C8	1.421 (3)	C5—H5A	0.9300
N—H0A	0.8600	C6—C7	1.385 (3)
O1—C4	1.364 (3)	C7—C8	1.389 (3)
O1—C2	1.427 (3)	C7—H7A	0.9300
C1—O2	1.408 (4)	C9—C10	1.485 (3)
C1—H1A	0.9600	C10—C15	1.381 (3)
C1—H1B	0.9600	C10—C11	1.382 (4)
C1—H1C	0.9600	C11—C12	1.374 (4)
O2—C6	1.365 (3)	C11—H11A	0.9300
C2—H2A	0.9600	C12—C13	1.367 (4)
C2—H2B	0.9600	C12—H12A	0.9300
C2—H2C	0.9600	C13—C14	1.357 (4)
O3—C9	1.226 (2)	C13—H13A	0.9300
C3—C8	1.372 (3)	C14—C15	1.376 (3)
C3—C4	1.387 (3)	C14—H14A	0.9300
C3—H3A	0.9300	C15—H15A	0.9300
C4—C5	1.367 (3)
C9—N—C8	123.69 (17)	C7—C6—C5	121.1 (2)
C9—N—H0A	118.2	C6—C7—C8	118.3 (2)
C8—N—H0A	118.2	C6—C7—H7A	120.9
C4—O1—C2	118.2 (2)	C8—C7—H7A	120.9
O2—C1—H1A	109.5	C3—C8—C7	121.2 (2)
O2—C1—H1B	109.5	C3—C8—N	118.17 (19)
H1A—C1—H1B	109.5	C7—C8—N	120.6 (2)
O2—C1—H1C	109.5	O3—C9—N	122.4 (2)
H1A—C1—H1C	109.5	O3—C9—C10	120.3 (2)
H1B—C1—H1C	109.5	N—C9—C10	117.24 (18)
C6—O2—C1	118.2 (2)	C15—C10—C11	118.5 (2)
O1—C2—H2A	109.5	C15—C10—C9	123.0 (2)
O1—C2—H2B	109.5	C11—C10—C9	118.5 (2)
H2A—C2—H2B	109.5	C12—C11—C10	120.3 (2)
O1—C2—H2C	109.5	C12—C11—H11A	119.9
H2A—C2—H2C	109.5	C10—C11—H11A	119.9
H2B—C2—H2C	109.5	C13—C12—C11	120.5 (3)
C8—C3—C4	119.3 (2)	C13—C12—H12A	119.7
C8—C3—H3A	120.3	C11—C12—H12A	119.7
C4—C3—H3A	120.3	C14—C13—C12	119.7 (3)
O1—C4—C5	124.7 (2)	C14—C13—H13A	120.2
O1—C4—C3	114.5 (2)	C12—C13—H13A	120.2
C5—C4—C3	120.8 (2)	C13—C14—C15	120.6 (2)
C4—C5—C6	119.3 (2)	C13—C14—H14A	119.7
C4—C5—H5A	120.3	C15—C14—H14A	119.7
C6—C5—H5A	120.3	C14—C15—C10	120.3 (2)
O2—C6—C7	124.0 (2)	C14—C15—H15A	119.8
O2—C6—C5	114.8 (2)	C10—C15—H15A	119.8
C2—O1—C4—C5	0.4 (4)	C9—N—C8—C3	−122.0 (2)
C2—O1—C4—C3	179.3 (2)	C9—N—C8—C7	59.1 (3)
C8—C3—C4—O1	−178.9 (2)	C8—N—C9—O3	−4.1 (4)
C8—C3—C4—C5	0.1 (3)	C8—N—C9—C10	175.41 (19)
O1—C4—C5—C6	179.8 (2)	O3—C9—C10—C15	−158.9 (2)
C3—C4—C5—C6	0.9 (4)	N—C9—C10—C15	21.6 (3)
C1—O2—C6—C7	2.3 (4)	O3—C9—C10—C11	18.8 (3)
C1—O2—C6—C5	−177.3 (3)	N—C9—C10—C11	−160.8 (2)
C4—C5—C6—O2	179.0 (2)	C15—C10—C11—C12	−0.2 (4)
C4—C5—C6—C7	−0.7 (4)	C9—C10—C11—C12	−177.9 (3)
O2—C6—C7—C8	179.9 (2)	C10—C11—C12—C13	1.7 (5)
C5—C6—C7—C8	−0.5 (3)	C11—C12—C13—C14	−2.5 (5)
C4—C3—C8—C7	−1.3 (3)	C12—C13—C14—C15	1.6 (5)
C4—C3—C8—N	179.8 (2)	C13—C14—C15—C10	−0.1 (4)
C6—C7—C8—C3	1.5 (3)	C11—C10—C15—C14	−0.7 (4)
C6—C7—C8—N	−179.6 (2)	C9—C10—C15—C14	177.0 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N—H0A···O3i	0.86	2.14	2.831 (3)	137

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N—H0A⋯O3i	0.86	2.14	2.831 (3)	137

Symmetry code: (i) .