2-Anilino-N-methyl-N-phenyl-benzamide.

The title compound, C(20)H(18)N(2)O, is composed of three aromatic rings, the dihedral angles between the phenyl and benzamide rings, and between the benzamide and aniline rings being 59.86 (9) and 46.57 (10)°, respectively. The mol-ecular structure is stabilized by an intra-molecular N-H⋯O hydrogen bond involving the amino H atom and the benzamide carbonyl O atom. In the crystal structure, C-H⋯O and C-H⋯π inter-actions are present.

Related literature

For the synthesis of the title compound, see: Martín et al. (2006 ▶); Charton et al. (2006 ▶). For related structures, see: Du et al. (2009 ▶); Qi et al. (2002 ▶). For further information on mol­ecular recognition and self-assembly, see: Brunsveld et al. (2001 ▶); Prins et al. (2001 ▶).

Experimental

Crystal data

C20H18N2O

M = 302.36

Orthorhombic,

a = 11.086 (2) Å

b = 18.150 (4) Å

c = 7.5962 (17) Å

V = 1528.4 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 93 K

0.40 × 0.30 × 0.20 mm

Data collection

Rigaku Spider diffractometer

Absorption correction: none

12048 measured reflections

1887 independent reflections

1803 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.033

wR(F 2) = 0.080

S = 1.18

1887 reflections

213 parameters

1 restraint

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.37 e Å−3

Δρmin = −0.18 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.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809013026/su2103sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809013026/su2103Isup2.hkl

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

C20H18N2O	F(000) = 640
Mr = 302.36	Dx = 1.314 Mg m−3
Orthorhombic, Pna21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2n	Cell parameters from 5383 reflections
a = 11.086 (2) Å	θ = 3.3–27.5°
b = 18.150 (4) Å	µ = 0.08 mm−1
c = 7.5962 (17) Å	T = 93 K
V = 1528.4 (6) Å3	Block, colorless
Z = 4	0.40 × 0.30 × 0.20 mm

Rigaku Spider diffractometer	1803 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.034
graphite	θmax = 27.5°, θmin = 3.4°
ω scans	h = −14→14
12048 measured reflections	k = −23→20
1887 independent reflections	l = −9→9

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)] = 0.033	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.080	H atoms treated by a mixture of independent and constrained refinement
S = 1.18	w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3
1887 reflections	(Δ/σ)max = 0.029
213 parameters	Δρmax = 0.37 e Å−3
1 restraint	Δρmin = −0.18 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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
O1	0.31344 (11)	0.23042 (7)	0.31485 (19)	0.0223 (4)
N1	0.17863 (14)	0.22432 (8)	0.5355 (2)	0.0181 (4)
N2	0.39961 (14)	0.36734 (8)	0.2705 (2)	0.0209 (5)
C1	0.15046 (16)	0.31901 (10)	0.7624 (3)	0.0185 (5)
C2	0.08545 (17)	0.34772 (10)	0.9013 (3)	0.0214 (5)
C3	−0.02095 (17)	0.31422 (11)	0.9550 (3)	0.0227 (5)
C4	−0.06272 (17)	0.25292 (10)	0.8662 (3)	0.0236 (5)
C5	0.00131 (18)	0.22422 (10)	0.7240 (3)	0.0221 (5)
C6	0.10850 (17)	0.25700 (10)	0.6736 (2)	0.0168 (5)
C7	0.23363 (16)	0.26105 (9)	0.4024 (2)	0.0170 (5)
C8	0.19527 (16)	0.33817 (9)	0.3594 (2)	0.0167 (5)
C9	0.07452 (17)	0.35920 (9)	0.3734 (3)	0.0186 (5)
C10	0.03721 (17)	0.42992 (10)	0.3310 (3)	0.0211 (5)
C11	0.12207 (17)	0.48030 (10)	0.2705 (2)	0.0210 (5)
C12	0.24121 (17)	0.46011 (9)	0.2502 (3)	0.0199 (5)
C13	0.28079 (16)	0.38908 (10)	0.2941 (2)	0.0174 (5)
C14	0.50151 (16)	0.41172 (10)	0.2448 (3)	0.0184 (5)
C15	0.51552 (17)	0.47993 (9)	0.3279 (3)	0.0198 (5)
C16	0.61982 (17)	0.52057 (10)	0.3017 (3)	0.0207 (5)
C17	0.71193 (17)	0.49442 (10)	0.1958 (3)	0.0209 (5)
C18	0.69897 (16)	0.42597 (10)	0.1170 (3)	0.0200 (5)
C19	0.59525 (16)	0.38490 (10)	0.1413 (3)	0.0193 (5)
C20	0.21883 (19)	0.14779 (10)	0.5689 (3)	0.0233 (6)
H1	0.22390	0.34160	0.72730	0.0220*
H2	0.11360	0.39050	0.96040	0.0260*
H2N	0.4137 (18)	0.3218 (13)	0.255 (3)	0.030 (6)*
H3	−0.06480	0.33330	1.05230	0.0270*
H4	−0.13580	0.23010	0.90230	0.0280*
H5	−0.02840	0.18250	0.66220	0.0260*
H9	0.01670	0.32430	0.41300	0.0220*
H10	−0.04500	0.44370	0.34300	0.0250*
H11	0.09780	0.52910	0.24290	0.0250*
H12	0.29740	0.49490	0.20560	0.0240*
H15	0.45360	0.49840	0.40230	0.0240*
H16	0.62820	0.56720	0.35740	0.0250*
H17	0.78280	0.52280	0.17750	0.0250*
H18	0.76210	0.40710	0.04550	0.0240*
H19	0.58790	0.33800	0.08690	0.0230*
H20A	0.23570	0.12330	0.45660	0.0280*
H20B	0.15520	0.12090	0.63140	0.0280*
H20C	0.29220	0.14850	0.64090	0.0280*

	U11	U22	U33	U12	U13	U23
O1	0.0217 (6)	0.0176 (6)	0.0277 (8)	0.0002 (5)	0.0058 (6)	−0.0024 (6)
N1	0.0235 (8)	0.0128 (7)	0.0179 (8)	0.0006 (6)	0.0020 (7)	−0.0003 (6)
N2	0.0190 (8)	0.0137 (7)	0.0300 (10)	−0.0008 (6)	0.0053 (7)	−0.0012 (7)
C1	0.0189 (8)	0.0175 (8)	0.0190 (9)	−0.0007 (7)	−0.0012 (8)	0.0013 (8)
C2	0.0259 (10)	0.0198 (9)	0.0185 (9)	0.0029 (7)	−0.0031 (8)	−0.0020 (8)
C3	0.0209 (9)	0.0295 (10)	0.0177 (9)	0.0076 (8)	0.0012 (8)	0.0014 (8)
C4	0.0190 (8)	0.0326 (10)	0.0193 (10)	−0.0017 (8)	0.0004 (8)	0.0039 (9)
C5	0.0258 (9)	0.0203 (9)	0.0202 (10)	−0.0043 (7)	−0.0014 (8)	0.0007 (8)
C6	0.0203 (9)	0.0162 (8)	0.0139 (9)	0.0023 (7)	−0.0004 (8)	0.0023 (7)
C7	0.0174 (8)	0.0160 (8)	0.0175 (9)	−0.0032 (7)	−0.0013 (8)	−0.0033 (7)
C8	0.0194 (9)	0.0165 (8)	0.0142 (9)	0.0001 (7)	0.0008 (7)	−0.0007 (7)
C9	0.0183 (9)	0.0220 (9)	0.0154 (9)	−0.0023 (7)	−0.0003 (7)	−0.0001 (8)
C10	0.0190 (9)	0.0241 (9)	0.0201 (10)	0.0027 (7)	−0.0012 (8)	0.0001 (8)
C11	0.0269 (10)	0.0169 (8)	0.0193 (10)	0.0025 (7)	−0.0037 (8)	0.0014 (8)
C12	0.0243 (9)	0.0173 (9)	0.0180 (10)	−0.0043 (7)	0.0004 (8)	0.0008 (8)
C13	0.0203 (8)	0.0178 (8)	0.0140 (9)	−0.0003 (7)	0.0003 (8)	−0.0033 (7)
C14	0.0199 (8)	0.0184 (8)	0.0169 (9)	−0.0013 (7)	0.0009 (8)	0.0033 (8)
C15	0.0208 (9)	0.0197 (9)	0.0189 (9)	0.0008 (7)	0.0021 (8)	0.0005 (8)
C16	0.0248 (9)	0.0162 (8)	0.0210 (10)	−0.0016 (7)	−0.0036 (8)	−0.0004 (7)
C17	0.0184 (9)	0.0207 (9)	0.0235 (10)	−0.0023 (7)	−0.0024 (8)	0.0060 (8)
C18	0.0178 (9)	0.0216 (9)	0.0207 (10)	0.0036 (7)	0.0017 (8)	0.0041 (8)
C19	0.0220 (9)	0.0176 (8)	0.0184 (9)	0.0036 (7)	−0.0002 (8)	0.0004 (8)
C20	0.0339 (11)	0.0132 (9)	0.0227 (10)	0.0012 (8)	0.0017 (9)	0.0018 (8)

O1—C7	1.239 (2)	C15—C16	1.386 (3)
N1—C6	1.434 (2)	C16—C17	1.384 (3)
N1—C7	1.356 (2)	C17—C18	1.387 (3)
N1—C20	1.481 (2)	C18—C19	1.383 (3)
N2—C13	1.387 (2)	C1—H1	0.9500
N2—C14	1.401 (2)	C2—H2	0.9500
N2—H2N	0.85 (2)	C3—H3	0.9500
C1—C2	1.380 (3)	C4—H4	0.9500
C1—C6	1.392 (3)	C5—H5	0.9500
C2—C3	1.388 (3)	C9—H9	0.9500
C3—C4	1.381 (3)	C10—H10	0.9500
C4—C5	1.394 (3)	C11—H11	0.9500
C5—C6	1.383 (3)	C12—H12	0.9500
C7—C8	1.499 (2)	C15—H15	0.9500
C8—C9	1.396 (3)	C16—H16	0.9500
C8—C13	1.414 (2)	C17—H17	0.9500
C9—C10	1.387 (3)	C18—H18	0.9500
C10—C11	1.390 (3)	C19—H19	0.9500
C11—C12	1.379 (3)	C20—H20A	0.9800
C12—C13	1.402 (2)	C20—H20B	0.9800
C14—C19	1.391 (3)	C20—H20C	0.9800
C14—C15	1.398 (3)
C6—N1—C7	125.87 (15)	C2—C1—H1	120.00
C6—N1—C20	115.20 (15)	C6—C1—H1	120.00
C7—N1—C20	116.98 (15)	C1—C2—H2	120.00
C13—N2—C14	128.34 (15)	C3—C2—H2	120.00
C14—N2—H2N	113.1 (14)	C2—C3—H3	120.00
C13—N2—H2N	118.0 (14)	C4—C3—H3	120.00
C2—C1—C6	120.08 (17)	C3—C4—H4	120.00
C1—C2—C3	120.20 (18)	C5—C4—H4	120.00
C2—C3—C4	119.6 (2)	C4—C5—H5	120.00
C3—C4—C5	120.59 (18)	C6—C5—H5	120.00
C4—C5—C6	119.44 (17)	C8—C9—H9	119.00
N1—C6—C5	119.37 (16)	C10—C9—H9	119.00
N1—C6—C1	120.51 (16)	C9—C10—H10	121.00
C1—C6—C5	120.05 (17)	C11—C10—H10	121.00
O1—C7—C8	120.32 (15)	C10—C11—H11	120.00
N1—C7—C8	119.61 (15)	C12—C11—H11	120.00
O1—C7—N1	120.06 (15)	C11—C12—H12	119.00
C9—C8—C13	119.41 (15)	C13—C12—H12	119.00
C7—C8—C9	120.71 (15)	C14—C15—H15	120.00
C7—C8—C13	119.77 (16)	C16—C15—H15	120.00
C8—C9—C10	121.43 (17)	C15—C16—H16	119.00
C9—C10—C11	118.94 (17)	C17—C16—H16	119.00
C10—C11—C12	120.68 (17)	C16—C17—H17	121.00
C11—C12—C13	121.16 (17)	C18—C17—H17	121.00
N2—C13—C8	119.76 (16)	C17—C18—H18	120.00
N2—C13—C12	121.88 (16)	C19—C18—H18	120.00
C8—C13—C12	118.33 (16)	C14—C19—H19	120.00
N2—C14—C15	122.39 (17)	C18—C19—H19	120.00
C15—C14—C19	118.82 (17)	N1—C20—H20A	109.00
N2—C14—C19	118.68 (17)	N1—C20—H20B	109.00
C14—C15—C16	119.94 (18)	N1—C20—H20C	109.00
C15—C16—C17	121.10 (18)	H20A—C20—H20B	109.00
C16—C17—C18	118.80 (17)	H20A—C20—H20C	109.00
C17—C18—C19	120.77 (18)	H20B—C20—H20C	109.00
C14—C19—C18	120.53 (18)
C7—N1—C6—C1	−46.1 (3)	N1—C7—C8—C9	−35.8 (2)
C7—N1—C6—C5	137.06 (19)	N1—C7—C8—C13	147.89 (16)
C20—N1—C6—C1	117.39 (19)	C7—C8—C9—C10	−178.79 (18)
C20—N1—C6—C5	−59.4 (2)	C13—C8—C9—C10	−2.5 (3)
C6—N1—C7—O1	163.40 (16)	C7—C8—C13—N2	−0.1 (2)
C6—N1—C7—C8	−18.0 (3)	C7—C8—C13—C12	178.12 (16)
C20—N1—C7—O1	0.1 (2)	C9—C8—C13—N2	−176.40 (16)
C20—N1—C7—C8	178.73 (15)	C9—C8—C13—C12	1.8 (2)
C14—N2—C13—C8	−164.91 (18)	C8—C9—C10—C11	1.1 (3)
C14—N2—C13—C12	17.0 (3)	C9—C10—C11—C12	1.0 (3)
C13—N2—C14—C15	35.8 (3)	C10—C11—C12—C13	−1.7 (3)
C13—N2—C14—C19	−148.16 (19)	C11—C12—C13—N2	178.41 (17)
C6—C1—C2—C3	1.1 (3)	C11—C12—C13—C8	0.3 (3)
C2—C1—C6—N1	−176.53 (17)	N2—C14—C15—C16	178.11 (19)
C2—C1—C6—C5	0.3 (3)	C19—C14—C15—C16	2.1 (3)
C1—C2—C3—C4	−1.4 (3)	N2—C14—C19—C18	−178.01 (19)
C2—C3—C4—C5	0.4 (3)	C15—C14—C19—C18	−1.9 (3)
C3—C4—C5—C6	1.0 (3)	C14—C15—C16—C17	−0.8 (3)
C4—C5—C6—N1	175.56 (17)	C15—C16—C17—C18	−0.7 (3)
C4—C5—C6—C1	−1.3 (3)	C16—C17—C18—C19	1.0 (3)
O1—C7—C8—C9	142.75 (18)	C17—C18—C19—C14	0.3 (3)
O1—C7—C8—C13	−33.5 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1	0.85 (2)	2.05 (2)	2.684 (2)	131.1 (18)
C9—H9···O1i	0.95	2.57	3.350 (2)	139
C2—H2···Cg2ii	0.95	2.75	3.420 (2)	129
C15—H15···Cg3iii	0.95	2.67	3.503 (2)	147
C20—H20A···Cg3i	0.98	2.67	3.441 (2)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1	0.85 (2)	2.05 (2)	2.684 (2)	131.1 (18)
C9—H9⋯O1i	0.95	2.57	3.350 (2)	139
C2—H2⋯Cg2ii	0.95	2.75	3.420 (2)	129
C15—H15⋯Cg3iii	0.95	2.67	3.503 (2)	147
C20—H20A⋯Cg3i	0.98	2.67	3.441 (2)	136

Symmetry codes: (i) ; (ii) ; (iii) . Cg2 and Cg3 are the centroids of the C8–C13 and C14–C19 rings, respectively.