N-(3,5-Dimeth­oxy­phen­yl)benzamide

Li, H.-L.; Cui, J.-T.

doi:10.1107/S1600536811019350

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1596

doi:10.1107/S1600536811019350

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N-(3,5-Dimethoxyphenyl)benzamide

Hong-Lei Li ^a ^* and Jiang-Tao Cui ^a

^aInstitute of Functional Biomolecules, State Key Laboratory of Pharmaceutical Biotechnology, Nanjing University, Nanjing 210093, People's Republic of China
^*Correspondence e-mail: lhlei2004@sina.com

(Received 11 April 2011; accepted 22 May 2011; online 11 June 2011)

The title compound, C₁₅H₁₅NO₃, was prepared by stirring benzoyl chloride with 3,5-dimethoxyaniline in dioxane at ambient temperature. The dimethoxyphenyl–amide segment of the molecule 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, intermolecular N—H⋯O interactions 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_r = 257.28
Monoclinic, P 2₁ /c
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[F² > 2σ(F²)] = 0.054
wR(F²) = 0.165
S = 1.00
2550 reflections
173 parameters
H-atom parameters constrained
Δρ_max = 0.17 e Å⁻³
Δρ_min = −0.19 e Å⁻³

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) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

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 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811019350/zj2010sup1.cif

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

Supporting information file. DOI: 10.1107/S1600536811019350/zj2010Isup3.cml

checkCIF report

Comment top

In this paper we report the structural information for the title compound, C₁₅H₁₅NO₃, obtained in our search for a strong anti-tumor reagent, for which the methoxyphenyl amide segment of the molecule is planar with a C8—N1—C9—O3 torsion angle of -4.1 (4)°. The two benzene rings are inclined at an angle of 76.66 (13)°. In the crystal structure, intermolecular O3···N interactions of 2.831 (3) Å, generate centrosymmetric dimmers, Fig 2. The packing is shown in Fig. 3. The bond lengths and angles of the title compound are in normal ranges when comparing with similar structures reported previously (Saeed et al. 2010; Wang et al. 2010; Anderson et al. 2005).

Related literature top

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 top

To a solution of 3, 5-dimethoxyaniline (1 mmol) in dry dioxane (2 ml) was added Et₃N (1 mmol). The solution was stirred at ambient temperature for 10 min and treated by dropwise addition of benzoyl chloride (1 mmol). The reaction mixture was stirred at room temperature for 1 h then hydrolyzed by adding H₂O and extracted with EtOAc. The organic layer was washed with brine, dried over anhydrous Na₂SO₄ and evaporated. The residue was purified by column chromatography eluted with petroleum ether: acetic ether (5:1) to N-(3, 5-dimethoxyphenyl) Benzamide as a light yellow powder and Yield 90%. Crystallization of the residue from methanol afforded the title compound (87%) as colourless crystals: ESI-MS TOF. calcd. for [M+Na]⁺: 280.09441; found: 280.09443.

Computing details top

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

Figures top

	Fig. 1. The structure of the title compound at 50% probability level.
	Fig. 2. N···O contacts in title compound (yellow line) linking the molecules into centrosymmetric dimers.
	Fig. 3. Crystal packing of title compound viewed down the b axis, with hydrogen bonds drawn as yellow lines and representative C–H interactions shown as light blue lines.

N-(3,5-Dimethoxyphenyl)benzamide top

Crystal data top

C₁₅H₁₅NO₃	F(000) = 544
M_r = 257.28	D_x = 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

Data collection top

Enraf–Nonius CAD-4 diffractometer	1564 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.033
Graphite monochromator	θ_max = 25.4°, θ_min = 2.0°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (North et al., 1968)	k = 0→24
T_min = 0.975, T_max = 0.991	l = −11→10
2737 measured reflections	3 standard reflections every 200 reflections
2550 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)] = 0.054	H-atom parameters constrained
wR(F²) = 0.165	w = 1/[σ²(F_o²) + (0.093P)²] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
2550 reflections	Δρ_max = 0.17 e Å⁻³
173 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: 0.037 (5)

Crystal data top

C₁₅H₁₅NO₃	V = 1388.1 (5) Å³
M_r = 257.28	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.0390 (16) Å	µ = 0.09 mm⁻¹
b = 20.003 (4) Å	T = 293 K
c = 9.2710 (19) Å	0.30 × 0.30 × 0.10 mm
β = 111.39 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1564 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.033
T_min = 0.975, T_max = 0.991	3 standard reflections every 200 reflections
2737 measured reflections	intensity decay: 1%
2550 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.165	H-atom parameters constrained
S = 1.00	Δρ_max = 0.17 e Å⁻³
2550 reflections	Δρ_min = −0.19 e Å⁻³
173 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 F²are 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	0.3527 (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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₅NO₃
M_r	257.28
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.0390 (16), 20.003 (4), 9.2710 (19)
β (°)	111.39 (3)
V (Å³)	1388.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.30 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.975, 0.991
No. of measured, independent and observed [I > 2σ(I)] reflections	2737, 2550, 1564
R_int	0.033

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.165, 1.00
No. of reflections	2550
No. of parameters	173
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

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) x, −y+1/2, z+1/2.

Acknowledgements

We thank Hua-Qin Wang of Center of Modern Analysis Nanjing University for valuable suggestions.

References

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