N-(2-Amino­phen­yl)-2-anilinobenzamide

Abstract

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,

• a = 6.707 (3) Å

• b = 25.95 (1) Å

• c = 9.480 (5) Å

• β = 103.398 (7)°

• V = 1605.0 (14) ų

• 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[F ² > 2σ(F ²)] = 0.035

• wR(F ²) = 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

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.

Supplementary Material

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

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)

supplementary crystallographic information

Comment

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)°.

Experimental

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.

Refinement

H atoms were placed in calculated positions with N—H = 0.88–0.93 Å and C—H = 0.95 Å and refined using a riding model with U_iso(H) = 1.2U_eq(C,N). In the absence of significant anomalous dispersion effects, Friedel pairs were averaged.

Figures

Fig. 1.

The molecular structure of the title compound, showing 30% probability displacement ellipsoids and the atomic numbering.

Crystal data

C19H17N3O	F(000) = 640
Mr = 303.36	Dx = 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

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

Refinement

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(Fo2) + (0.0376P)2] where P = (Fo2 + 2Fc2)/3
1844 reflections	(Δ/σ)max < 0.001
224 parameters	Δρmax = 0.14 e Å−3
2 restraints	Δρmin = −0.15 e Å−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
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 (Ų)

	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, °)

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, °)

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)