N-(2-Amino­phen­yl)-2-anilinobenzamide

Huang, K.; Huang, F.; Qin, D.-B.

doi:10.1107/S1600536809013014

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o1108

doi:10.1107/S1600536809013014

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N-(2-Aminophenyl)-2-anilinobenzamide

Kun Huang,^a Feng Huang ^a and Da-Bin Qin ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: qindabincwnu@yahoo.com.cn

(Received 16 March 2009; accepted 6 April 2009; online 25 April 2009)

In the title compound, C₁₉H₁₇N₃O, the planes of the aromatic substituents attached to the benzamide moiety are almost perpendicular to one another, making a dihedral angle of 88.16 (7)°. The observed conformation of the molecule is produced by an intramolecular N—H⋯O hydrogen bond.

Related literature

For the synthesis, see: Martín et al. (2006 ); Charton et al. (2006 ). For related structures, see: Yusof et al. (2003 ); Du et al. (2009 ).

Experimental

Crystal data

C₁₉H₁₇N₃O
M_r = 303.36
Monoclinic, C c
a = 6.707 (3) Å
b = 25.95 (1) Å
c = 9.480 (5) Å
β = 103.398 (7)°
V = 1605.0 (14) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 93 K
0.40 × 0.27 × 0.10 mm

Data collection

Rigaku Spider diffractometer
Absorption correction: none
6515 measured reflections
1844 independent reflections
1695 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.035
wR(F²) = 0.072
S = 1.00
1844 reflections
224 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.15 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1	0.88 (3)	1.96 (3)	2.714 (3)	142 (2)

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; 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 global, I. DOI: 10.1107/S1600536809013014/im2107sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809013014/im2107Isup2.hkl

checkCIF report

Comment top

Nowadays many researchers are intrested in the synthesis of new insecticides. Benzamide or its derivatives or analogs are used in the pharmaceutical industry for this purpose. We herein report the crystal structure of the title compound.

Bond lengths and angles in the title molecule (Fig. 1) are within normal ranges. The planes of the aromatic substituents attached to the benzamide moiety (C7—C12 and C14—C19) are almost perpendicular to one another, with a dihedral angle of 88.16 (7)° whereas the dihedral angle between C7—C12 and C1—C6 measures to 47.28 (9)°. The planes between C7—C12 and the amide moiety C12/C13/N2/O1 enclose an angle of 63.06 (8)°.

Related literature top

For the synthesis, see: Martín et al. (2006); Charton et al. (2006). For related structures, see: Yusof et al. (2003); Du et al. (2009).

Experimental top

The title compound was prepared according to the reported procedure of Martín et al. (2006). and Charton et al. (2006). Colourless single crystals suitable for X-ray diffraction were obtained by recrystallization from dichloromethane.

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); 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 the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

N-(2-Aminophenyl)-2-anilinobenzamide top

Crystal data top

C₁₉H₁₇N₃O	F(000) = 640
M_r = 303.36	D_x = 1.255 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2858 reflections
a = 6.707 (3) Å	θ = 3.1–27.5°
b = 25.95 (1) Å	µ = 0.08 mm⁻¹
c = 9.480 (5) Å	T = 93 K
β = 103.398 (7)°	Platelet, colorless
V = 1605.0 (14) Å³	0.40 × 0.27 × 0.10 mm
Z = 4

Data collection top

Rigaku Spider diffractometer	1695 reflections with I > 2σ(I)
Radiation source: Rotating Anode	R_int = 0.029
Graphite monochromator	θ_max = 27.5°, θ_min = 3.1°
ω scans	h = −8→8
6515 measured reflections	k = −33→31
1844 independent reflections	l = −12→12

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.035	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	w = 1/[σ²(F_o²) + (0.0376P)²] where P = (F_o² + 2F_c²)/3
1844 reflections	(Δ/σ)_max < 0.001
224 parameters	Δρ_max = 0.14 e Å⁻³
2 restraints	Δρ_min = −0.15 e Å⁻³

Crystal data top

C₁₉H₁₇N₃O	V = 1605.0 (14) Å³
M_r = 303.36	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 6.707 (3) Å	µ = 0.08 mm⁻¹
b = 25.95 (1) Å	T = 93 K
c = 9.480 (5) Å	0.40 × 0.27 × 0.10 mm
β = 103.398 (7)°

Data collection top

Rigaku Spider diffractometer	1695 reflections with I > 2σ(I)
6515 measured reflections	R_int = 0.029
1844 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.035	2 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.00	Δρ_max = 0.14 e Å⁻³
1844 reflections	Δρ_min = −0.15 e Å⁻³
224 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
O1	0.4009 (2)	0.47225 (5)	0.56166 (13)	0.0295 (3)
N2	0.3896 (2)	0.51617 (6)	0.35407 (16)	0.0257 (3)
N1	0.4426 (3)	0.36962 (7)	0.52152 (19)	0.0368 (4)
N3	0.0087 (3)	0.53595 (9)	0.16236 (19)	0.0418 (5)
H3A	0.106 (4)	0.5228 (9)	0.121 (3)	0.053 (7)*
H3B	−0.103 (4)	0.5495 (10)	0.097 (3)	0.063 (8)*
C1	0.3021 (4)	0.28921 (8)	0.3998 (2)	0.0435 (6)
H1	0.3647	0.2955	0.3212	0.052*
C2	0.1803 (4)	0.24613 (9)	0.3980 (3)	0.0600 (7)
H2	0.1605	0.2230	0.3183	0.072*
C3	0.0878 (5)	0.23638 (10)	0.5100 (4)	0.0725 (9)
H3	0.0028	0.2070	0.5080	0.087*
C4	0.1209 (5)	0.27031 (10)	0.6262 (4)	0.0674 (8)
H4	0.0588	0.2638	0.7049	0.081*
C5	0.2422 (4)	0.31325 (9)	0.6295 (3)	0.0470 (6)
H5	0.2633	0.3360	0.7100	0.056*
C6	0.3335 (3)	0.32336 (8)	0.5156 (2)	0.0366 (5)
C7	0.5729 (3)	0.38514 (8)	0.4348 (2)	0.0326 (5)
C8	0.7016 (3)	0.34982 (9)	0.3887 (2)	0.0425 (5)
H8	0.6954	0.3144	0.4127	0.051*
C9	0.8377 (4)	0.36594 (10)	0.3087 (2)	0.0475 (6)
H9	0.9231	0.3413	0.2773	0.057*
C10	0.8519 (3)	0.41732 (10)	0.2733 (2)	0.0429 (6)
H10	0.9467	0.4281	0.2187	0.052*
C11	0.7264 (3)	0.45261 (9)	0.3184 (2)	0.0331 (5)
H11	0.7366	0.4880	0.2952	0.040*
C12	0.5841 (3)	0.43752 (8)	0.39754 (18)	0.0271 (4)
C13	0.4524 (3)	0.47661 (7)	0.44460 (18)	0.0245 (4)
C14	0.2603 (3)	0.55640 (7)	0.38352 (19)	0.0272 (4)
C15	0.3209 (3)	0.58570 (8)	0.5089 (2)	0.0324 (4)
H15	0.4505	0.5797	0.5728	0.039*
C16	0.1931 (4)	0.62359 (9)	0.5410 (2)	0.0420 (5)
H16	0.2341	0.6435	0.6269	0.050*
C17	0.0059 (4)	0.63226 (10)	0.4473 (2)	0.0492 (6)
H17	−0.0831	0.6579	0.4697	0.059*
C18	−0.0532 (4)	0.60405 (10)	0.3216 (2)	0.0468 (6)
H18	−0.1821	0.6108	0.2577	0.056*
C19	0.0727 (3)	0.56574 (8)	0.2863 (2)	0.0339 (5)
H1N	0.400 (4)	0.3966 (10)	0.563 (3)	0.053 (7)*
H2N	0.414 (3)	0.5148 (7)	0.269 (2)	0.030 (5)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0355 (7)	0.0417 (8)	0.0137 (6)	−0.0010 (6)	0.0106 (5)	−0.0004 (5)
N2	0.0232 (8)	0.0413 (9)	0.0144 (7)	0.0023 (7)	0.0076 (6)	0.0006 (7)
N1	0.0459 (11)	0.0375 (10)	0.0305 (9)	−0.0001 (8)	0.0162 (8)	−0.0020 (8)
N3	0.0251 (9)	0.0777 (15)	0.0209 (9)	0.0039 (9)	0.0022 (8)	−0.0025 (9)
C1	0.0528 (14)	0.0313 (11)	0.0418 (13)	0.0092 (10)	0.0019 (11)	0.0049 (10)
C2	0.0694 (18)	0.0288 (12)	0.0729 (18)	0.0060 (11)	−0.0017 (16)	0.0033 (12)
C3	0.078 (2)	0.0320 (14)	0.107 (3)	−0.0012 (13)	0.0214 (19)	0.0199 (16)
C4	0.084 (2)	0.0450 (15)	0.081 (2)	0.0042 (14)	0.0353 (17)	0.0261 (15)
C5	0.0580 (15)	0.0393 (12)	0.0475 (14)	0.0108 (11)	0.0199 (12)	0.0167 (11)
C6	0.0423 (13)	0.0324 (11)	0.0330 (11)	0.0081 (9)	0.0043 (9)	0.0101 (9)
C7	0.0315 (11)	0.0456 (13)	0.0207 (10)	0.0045 (9)	0.0058 (8)	−0.0018 (9)
C8	0.0457 (13)	0.0486 (13)	0.0325 (12)	0.0126 (10)	0.0076 (10)	−0.0025 (10)
C9	0.0411 (13)	0.0673 (17)	0.0364 (13)	0.0193 (12)	0.0137 (11)	−0.0061 (11)
C10	0.0275 (11)	0.0734 (17)	0.0294 (12)	0.0091 (10)	0.0098 (9)	−0.0053 (11)
C11	0.0226 (9)	0.0560 (13)	0.0207 (10)	0.0036 (9)	0.0050 (8)	−0.0017 (9)
C12	0.0239 (9)	0.0413 (11)	0.0151 (9)	0.0032 (8)	0.0025 (7)	−0.0017 (8)
C13	0.0198 (9)	0.0383 (11)	0.0153 (9)	−0.0034 (8)	0.0037 (7)	−0.0020 (8)
C14	0.0263 (10)	0.0371 (10)	0.0193 (9)	0.0006 (8)	0.0079 (8)	0.0041 (8)
C15	0.0366 (11)	0.0403 (11)	0.0211 (10)	−0.0017 (9)	0.0082 (8)	0.0019 (9)
C16	0.0592 (15)	0.0385 (12)	0.0340 (11)	0.0015 (10)	0.0225 (11)	0.0003 (10)
C17	0.0615 (16)	0.0546 (15)	0.0392 (14)	0.0227 (12)	0.0274 (13)	0.0120 (11)
C18	0.0390 (13)	0.0721 (16)	0.0319 (12)	0.0204 (12)	0.0132 (10)	0.0145 (11)
C19	0.0287 (11)	0.0548 (13)	0.0196 (9)	0.0035 (9)	0.0085 (8)	0.0064 (9)

Geometric parameters (Å, º) top

O1—C13	1.241 (2)	C7—C8	1.397 (3)
N2—C13	1.342 (2)	C7—C12	1.411 (3)
N2—C14	1.425 (2)	C8—C9	1.380 (3)
N2—H2N	0.86 (2)	C8—H8	0.9500
N1—C7	1.391 (3)	C9—C10	1.384 (4)
N1—C6	1.400 (3)	C9—H9	0.9500
N1—H1N	0.88 (3)	C10—C11	1.377 (3)
N3—C19	1.389 (3)	C10—H10	0.9500
N3—H3A	0.90 (3)	C11—C12	1.400 (3)
N3—H3B	0.93 (3)	C11—H11	0.9500
C1—C2	1.382 (4)	C12—C13	1.480 (2)
C1—C6	1.389 (3)	C14—C15	1.390 (3)
C1—H1	0.9500	C14—C19	1.398 (3)
C2—C3	1.372 (4)	C15—C16	1.384 (3)
C2—H2	0.9500	C15—H15	0.9500
C3—C4	1.387 (4)	C16—C17	1.378 (3)
C3—H3	0.9500	C16—H16	0.9500
C4—C5	1.376 (4)	C17—C18	1.376 (4)
C4—H4	0.9500	C17—H17	0.9500
C5—C6	1.383 (3)	C18—C19	1.394 (3)
C5—H5	0.9500	C18—H18	0.9500

C13—N2—C14	123.37 (15)	C8—C9—C10	121.1 (2)
C13—N2—H2N	118.0 (13)	C8—C9—H9	119.4
C14—N2—H2N	118.0 (13)	C10—C9—H9	119.4
C7—N1—C6	128.24 (19)	C11—C10—C9	119.0 (2)
C7—N1—H1N	110.2 (17)	C11—C10—H10	120.5
C6—N1—H1N	118.5 (17)	C9—C10—H10	120.5
C19—N3—H3A	117.9 (16)	C10—C11—C12	121.5 (2)
C19—N3—H3B	113.5 (16)	C10—C11—H11	119.3
H3A—N3—H3B	114 (2)	C12—C11—H11	119.3
C2—C1—C6	120.4 (2)	C11—C12—C7	119.10 (18)
C2—C1—H1	119.8	C11—C12—C13	119.91 (18)
C6—C1—H1	119.8	C7—C12—C13	120.96 (17)
C3—C2—C1	120.8 (3)	O1—C13—N2	122.03 (17)
C3—C2—H2	119.6	O1—C13—C12	121.07 (17)
C1—C2—H2	119.6	N2—C13—C12	116.89 (15)
C2—C3—C4	118.7 (3)	C15—C14—C19	120.58 (18)
C2—C3—H3	120.7	C15—C14—N2	119.84 (17)
C4—C3—H3	120.7	C19—C14—N2	119.57 (17)
C5—C4—C3	121.1 (3)	C16—C15—C14	120.2 (2)
C5—C4—H4	119.4	C16—C15—H15	119.9
C3—C4—H4	119.4	C14—C15—H15	119.9
C4—C5—C6	120.1 (3)	C17—C16—C15	119.5 (2)
C4—C5—H5	119.9	C17—C16—H16	120.2
C6—C5—H5	119.9	C15—C16—H16	120.2
C5—C6—C1	118.9 (2)	C18—C17—C16	120.5 (2)
C5—C6—N1	116.9 (2)	C18—C17—H17	119.8
C1—C6—N1	124.09 (19)	C16—C17—H17	119.8
N1—C7—C8	120.88 (19)	C17—C18—C19	121.2 (2)
N1—C7—C12	120.29 (18)	C17—C18—H18	119.4
C8—C7—C12	118.77 (19)	C19—C18—H18	119.4
C9—C8—C7	120.6 (2)	N3—C19—C18	120.96 (19)
C9—C8—H8	119.7	N3—C19—C14	121.04 (19)
C7—C8—H8	119.7	C18—C19—C14	117.92 (19)

C6—C1—C2—C3	0.2 (4)	N1—C7—C12—C13	−2.4 (3)
C1—C2—C3—C4	−0.8 (4)	C8—C7—C12—C13	−179.51 (17)
C2—C3—C4—C5	0.6 (4)	C14—N2—C13—O1	0.2 (3)
C3—C4—C5—C6	0.1 (4)	C14—N2—C13—C12	179.19 (17)
C4—C5—C6—C1	−0.7 (4)	C11—C12—C13—O1	−145.63 (18)
C4—C5—C6—N1	175.5 (2)	C7—C12—C13—O1	32.5 (3)
C2—C1—C6—C5	0.5 (3)	C11—C12—C13—N2	35.3 (2)
C2—C1—C6—N1	−175.4 (2)	C7—C12—C13—N2	−146.50 (18)
C7—N1—C6—C5	169.1 (2)	C13—N2—C14—C15	57.6 (2)
C7—N1—C6—C1	−14.9 (3)	C13—N2—C14—C19	−121.91 (19)
C6—N1—C7—C8	−37.1 (3)	C19—C14—C15—C16	1.8 (3)
C6—N1—C7—C12	145.9 (2)	N2—C14—C15—C16	−177.67 (18)
N1—C7—C8—C9	−176.8 (2)	C14—C15—C16—C17	−0.4 (3)
C12—C7—C8—C9	0.2 (3)	C15—C16—C17—C18	−0.9 (3)
C7—C8—C9—C10	0.7 (3)	C16—C17—C18—C19	0.7 (3)
C8—C9—C10—C11	−0.5 (3)	C17—C18—C19—N3	177.3 (2)
C9—C10—C11—C12	−0.7 (3)	C17—C18—C19—C14	0.7 (3)
C10—C11—C12—C7	1.6 (3)	C15—C14—C19—N3	−178.58 (18)
C10—C11—C12—C13	179.76 (18)	N2—C14—C19—N3	0.9 (3)
N1—C7—C12—C11	175.75 (17)	C15—C14—C19—C18	−2.0 (3)
C8—C7—C12—C11	−1.3 (3)	N2—C14—C19—C18	177.54 (18)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88 (3)	1.96 (3)	2.714 (3)	142 (2)

Experimental details

Crystal data
Chemical formula	C₁₉H₁₇N₃O
M_r	303.36
Crystal system, space group	Monoclinic, Cc
Temperature (K)	93
a, b, c (Å)	6.707 (3), 25.95 (1), 9.480 (5)
β (°)	103.398 (7)
V (Å³)	1605.0 (14)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.40 × 0.27 × 0.10

Data collection
Diffractometer	Rigaku Spider diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	6515, 1844, 1695
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.651

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.035, 0.072, 1.00
No. of reflections	1844
No. of parameters	224
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.15

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1	0.88 (3)	1.96 (3)	2.714 (3)	142 (2)

Acknowledgements

The authors thank the Scientific Research Fund Projects of China West Normal University (grant No. 06B003) and the Youth Fund Projects of Sichuan Educational Department (grant No. 2006B039).

References

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