2,2'-Diamino-N,N'-(o-phenyl-ene)di-benz-amide.

In the structure of the title compound, C(20)H(18)N(4)O(2), the N-H and C=O bonds are trans to each other and the amide O atoms are syn to the ortho amino N atom in the benzoyl rings. The amide groups form dihedral angles of 8.4 (2) and 13.8 (2)° with their respective benzoyl rings, and dihedral angles of 51.85 (16) and 51.19 (17)° with the phenyl-enediamine ring. In the crystal, a centrosymmetric dimer is formed by inter-molecular N-H⋯O hydrogen bonds, resulting in an R(2) (2)(14) descriptor on a unitary level of graph-set analysis, and three intramolecular N-H⋯O bonds also occur.

Related literature

For the synthesis, see: Black & Rothnie (1983 ▶). For metal coordination, see: Booysen et al. (2008 ▶). For stereoselectivity in synthesis, see: Valik et al. (2002 ▶). For applications of polyamides, see: Kang et al. (2001 ▶). For related structures, see Gowda et al. (2003 ▶, 2008 ▶). For graph-set notation, see: Bernstein et al. (1995 ▶).

Experimental

Crystal data

C20H18N4O2

M = 346.38

Monoclinic,

a = 8.7464 (3) Å

b = 14.4308 (6) Å

c = 13.6161 (6) Å

β = 97.291 (3)°

V = 1704.69 (12) Å3

Z = 4

Mo Kα radiation

μ = 0.09 mm−1

T = 200 K

0.16 × 0.14 × 0.10 mm

Data collection

Nonius KappaCCD diffractometer

Absorption correction: none

7575 measured reflections

3893 independent reflections

2085 reflections with I > 2σ(I)

R int = 0.049

Refinement

R[F 2 > 2σ(F 2)] = 0.047

wR(F 2) = 0.122

S = 0.99

3893 reflections

308 parameters

All H-atom parameters refined

Δρmax = 0.19 e Å−3

Δρmin = −0.20 e Å−3

Data collection: COLLECT (Nonius, 2004 ▶); cell refinement: SCALEPACK (Otwinowski & Minor, 1997 ▶); data reduction: DENZO (Otwinowski & Minor, 1997 ▶) and SCALEPACK; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2006 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶) and WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809009283/sj2594sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809009283/sj2594Isup2.hkl

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

C20H18N4O2	F(000) = 728
Mr = 346.38	Dx = 1.350 Mg m−3
Monoclinic, P21/n	Melting point: 532 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.7464 (3) Å	Cell parameters from 12612 reflections
b = 14.4308 (6) Å	θ = 3.1–27.5°
c = 13.6161 (6) Å	µ = 0.09 mm−1
β = 97.291 (3)°	T = 200 K
V = 1704.69 (12) Å3	Block, brown
Z = 4	0.16 × 0.14 × 0.10 mm

Nonius KappaCCD diffractometer	2085 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.049
MONTEL, graded multilayered X-ray optics	θmax = 27.5°, θmin = 3.2°
Detector resolution: 9 pixels mm-1	h = −11→11
CCD; rotation images; thick slices scans	k = −18→18
7575 measured reflections	l = −17→17
3893 independent reflections

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)] = 0.047	All H-atom parameters refined
wR(F2) = 0.122	w = 1/[σ2(Fo2) + (0.0521P)2] where P = (Fo2 + 2Fc2)/3
S = 0.99	(Δ/σ)max = 0.001
3893 reflections	Δρmax = 0.19 e Å−3
308 parameters	Δρmin = −0.19 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (17)

	x	y	z	Uiso*/Ueq
O1	0.50757 (13)	0.19967 (8)	1.10126 (9)	0.0426 (4)
O2	0.33370 (13)	0.11696 (9)	0.75452 (9)	0.0431 (4)
N1	0.45030 (17)	0.17105 (11)	0.93824 (12)	0.0371 (4)
N2	0.3038 (2)	0.28860 (15)	1.19702 (14)	0.0599 (5)
N3	0.43678 (16)	−0.00594 (12)	0.84087 (11)	0.0364 (4)
N4	0.1025 (3)	0.08932 (14)	0.61238 (15)	0.0579 (5)
C1	0.41993 (19)	0.21187 (12)	1.02250 (14)	0.0343 (4)
C2	0.27907 (18)	0.27011 (11)	1.01692 (13)	0.0350 (4)
C3	0.2292 (2)	0.30615 (13)	1.10429 (15)	0.0437 (5)
C4	0.0941 (2)	0.35939 (15)	1.0947 (2)	0.0552 (6)
C5	0.0119 (2)	0.37821 (15)	1.00496 (19)	0.0566 (6)
C6	0.0630 (2)	0.34564 (15)	0.91861 (18)	0.0552 (6)
C7	0.1946 (2)	0.29271 (14)	0.92620 (16)	0.0457 (5)
C8	0.58760 (18)	0.12237 (12)	0.92527 (12)	0.0334 (4)
C9	0.57907 (18)	0.03780 (12)	0.87594 (12)	0.0331 (4)
C10	0.7152 (2)	−0.00822 (14)	0.86314 (14)	0.0408 (5)
C11	0.8571 (2)	0.02948 (15)	0.89720 (14)	0.0451 (5)
C12	0.8644 (2)	0.11444 (14)	0.94410 (14)	0.0422 (5)
C13	0.7312 (2)	0.16123 (14)	0.95732 (13)	0.0377 (5)
C14	0.32233 (19)	0.03407 (13)	0.77899 (12)	0.0346 (4)
C15	0.18663 (18)	−0.02232 (12)	0.74265 (12)	0.0339 (4)
C16	0.0793 (2)	0.00956 (13)	0.66357 (13)	0.0419 (5)
C17	−0.0521 (2)	−0.04422 (16)	0.63397 (16)	0.0501 (5)
C18	−0.0768 (2)	−0.12620 (16)	0.67972 (17)	0.0515 (6)
C19	0.0285 (2)	−0.15877 (15)	0.75605 (16)	0.0480 (5)
C20	0.1582 (2)	−0.10711 (13)	0.78674 (15)	0.0408 (5)
H13	0.7350 (18)	0.2213 (13)	0.9913 (13)	0.043 (5)*
H20	0.2287 (19)	−0.1285 (12)	0.8428 (13)	0.044 (5)*
H1	0.3885 (19)	0.1773 (13)	0.8853 (13)	0.040 (6)*
H10	0.7102 (18)	−0.0671 (13)	0.8292 (12)	0.041 (5)*
H12	0.960 (2)	0.1435 (12)	0.9685 (13)	0.047 (5)*
H3	0.435 (2)	−0.0647 (15)	0.8504 (13)	0.044 (6)*
H11	0.951 (2)	−0.0045 (13)	0.8853 (15)	0.062 (6)*
H5	−0.083 (2)	0.4151 (14)	1.0036 (13)	0.059 (6)*
H17	−0.132 (2)	−0.0200 (13)	0.5784 (14)	0.056 (6)*
H18	−0.168 (2)	−0.1625 (14)	0.6568 (14)	0.056 (6)*
H7	0.231 (2)	0.2720 (13)	0.8671 (15)	0.050 (5)*
H4	0.063 (2)	0.3824 (14)	1.1515 (16)	0.068 (7)*
H19	0.011 (2)	−0.2158 (14)	0.7871 (13)	0.052 (6)*
H41	0.027 (3)	0.1085 (16)	0.5717 (18)	0.076 (8)*
H6	0.010 (2)	0.3612 (14)	0.8493 (17)	0.076 (7)*
H42	0.178 (3)	0.1311 (17)	0.647 (2)	0.090 (8)*
H21	0.405 (3)	0.2631 (16)	1.2012 (17)	0.083 (8)*
H22	0.288 (3)	0.3284 (19)	1.2441 (19)	0.090 (9)*

	U11	U22	U33	U12	U13	U23
O1	0.0509 (8)	0.0387 (8)	0.0375 (8)	0.0062 (6)	0.0034 (6)	−0.0021 (6)
O2	0.0499 (8)	0.0374 (8)	0.0412 (8)	−0.0016 (6)	0.0027 (6)	0.0061 (6)
N1	0.0371 (9)	0.0387 (10)	0.0349 (10)	0.0081 (7)	0.0030 (7)	−0.0038 (8)
N2	0.0682 (14)	0.0678 (14)	0.0466 (12)	0.0046 (10)	0.0183 (10)	−0.0122 (10)
N3	0.0359 (9)	0.0300 (10)	0.0427 (10)	0.0037 (7)	0.0025 (7)	0.0016 (8)
N4	0.0608 (12)	0.0560 (13)	0.0524 (12)	0.0074 (10)	−0.0109 (10)	0.0137 (10)
C1	0.0402 (10)	0.0275 (10)	0.0362 (11)	−0.0034 (8)	0.0095 (9)	0.0002 (8)
C2	0.0378 (10)	0.0266 (10)	0.0423 (11)	0.0012 (8)	0.0113 (8)	0.0010 (8)
C3	0.0472 (11)	0.0365 (12)	0.0508 (13)	−0.0022 (9)	0.0190 (10)	−0.0027 (9)
C4	0.0543 (13)	0.0481 (14)	0.0689 (17)	0.0041 (11)	0.0304 (13)	−0.0071 (12)
C5	0.0436 (12)	0.0419 (13)	0.0876 (19)	0.0088 (10)	0.0206 (13)	0.0030 (12)
C6	0.0478 (12)	0.0506 (14)	0.0675 (16)	0.0117 (10)	0.0088 (11)	0.0100 (12)
C7	0.0450 (11)	0.0459 (13)	0.0481 (13)	0.0087 (9)	0.0135 (10)	0.0040 (10)
C8	0.0332 (9)	0.0344 (11)	0.0333 (10)	0.0045 (8)	0.0072 (7)	0.0033 (8)
C9	0.0343 (10)	0.0332 (11)	0.0318 (10)	0.0030 (8)	0.0048 (7)	0.0029 (8)
C10	0.0428 (11)	0.0397 (12)	0.0410 (12)	0.0073 (9)	0.0089 (9)	−0.0009 (9)
C11	0.0380 (11)	0.0521 (14)	0.0462 (13)	0.0092 (10)	0.0093 (9)	0.0028 (10)
C12	0.0336 (11)	0.0521 (14)	0.0409 (12)	−0.0017 (10)	0.0043 (9)	0.0058 (10)
C13	0.0400 (11)	0.0370 (12)	0.0364 (11)	−0.0004 (9)	0.0054 (8)	0.0022 (9)
C14	0.0388 (10)	0.0367 (12)	0.0302 (10)	0.0053 (9)	0.0114 (8)	0.0008 (9)
C15	0.0363 (10)	0.0355 (11)	0.0303 (10)	0.0035 (8)	0.0061 (8)	−0.0022 (8)
C16	0.0456 (11)	0.0428 (13)	0.0370 (12)	0.0075 (9)	0.0041 (9)	−0.0029 (9)
C17	0.0438 (12)	0.0540 (15)	0.0498 (14)	0.0046 (11)	−0.0045 (10)	−0.0093 (11)
C18	0.0405 (12)	0.0522 (15)	0.0613 (15)	−0.0014 (11)	0.0038 (10)	−0.0189 (12)
C19	0.0451 (12)	0.0421 (13)	0.0580 (14)	−0.0019 (10)	0.0113 (10)	−0.0032 (11)
C20	0.0406 (11)	0.0416 (12)	0.0403 (12)	0.0018 (9)	0.0055 (9)	−0.0002 (9)

O1—C1	1.249 (2)	C6—H6	1.02 (2)
O2—C14	1.249 (2)	C7—H7	0.95 (2)
N1—C1	1.346 (2)	C8—C9	1.390 (2)
N1—C8	1.421 (2)	C8—C13	1.394 (2)
N1—H1	0.849 (17)	C9—C10	1.394 (2)
N2—C3	1.369 (3)	C10—C11	1.380 (3)
N2—H21	0.95 (2)	C10—H10	0.966 (19)
N2—H22	0.89 (3)	C11—C12	1.380 (3)
N3—C14	1.353 (2)	C11—H11	0.986 (19)
N3—C9	1.423 (2)	C12—C13	1.378 (3)
N3—H3	0.86 (2)	C12—H12	0.957 (18)
N4—C16	1.374 (2)	C13—H13	0.981 (18)
N4—H41	0.85 (2)	C14—C15	1.472 (2)
N4—H42	0.97 (3)	C15—C20	1.399 (2)
C1—C2	1.485 (2)	C15—C16	1.413 (2)
C2—C7	1.395 (3)	C16—C17	1.403 (3)
C2—C3	1.417 (2)	C17—C18	1.367 (3)
C3—C4	1.402 (3)	C17—H17	1.024 (19)
C4—C5	1.364 (3)	C18—C19	1.380 (3)
C4—H4	0.91 (2)	C18—H18	0.97 (2)
C5—C6	1.391 (3)	C19—C20	1.378 (3)
C5—H5	0.98 (2)	C19—H19	0.945 (19)
C6—C7	1.374 (3)	C20—H20	0.968 (18)
C1—N1—C8	125.70 (16)	C8—C9—C10	118.97 (16)
C1—N1—H1	120.3 (12)	C8—C9—N3	122.85 (14)
C8—N1—H1	113.8 (12)	C10—C9—N3	118.14 (17)
C3—N2—H21	117.2 (14)	C11—C10—C9	121.07 (19)
C3—N2—H22	116.6 (16)	C11—C10—H10	119.5 (10)
H21—N2—H22	116 (2)	C9—C10—H10	119.4 (10)
C14—N3—C9	124.48 (17)	C10—C11—C12	119.55 (18)
C14—N3—H3	119.2 (12)	C10—C11—H11	118.6 (11)
C9—N3—H3	114.9 (12)	C12—C11—H11	121.8 (11)
C16—N4—H41	116.7 (15)	C13—C12—C11	120.32 (18)
C16—N4—H42	114.2 (15)	C13—C12—H12	117.2 (11)
H41—N4—H42	122 (2)	C11—C12—H12	122.5 (11)
O1—C1—N1	120.28 (16)	C12—C13—C8	120.35 (19)
O1—C1—C2	122.57 (16)	C12—C13—H13	121.0 (10)
N1—C1—C2	117.15 (16)	C8—C13—H13	118.6 (10)
C7—C2—C3	118.21 (17)	O2—C14—N3	119.81 (16)
C7—C2—C1	121.35 (16)	O2—C14—C15	121.86 (16)
C3—C2—C1	120.42 (16)	N3—C14—C15	118.33 (17)
N2—C3—C4	118.99 (19)	C20—C15—C16	118.35 (17)
N2—C3—C2	123.05 (17)	C20—C15—C14	121.25 (16)
C4—C3—C2	117.92 (19)	C16—C15—C14	120.38 (17)
C5—C4—C3	122.4 (2)	N4—C16—C17	119.08 (19)
C5—C4—H4	120.6 (13)	N4—C16—C15	122.20 (18)
C3—C4—H4	117.0 (13)	C17—C16—C15	118.67 (19)
C4—C5—C6	120.0 (2)	C18—C17—C16	121.3 (2)
C4—C5—H5	118.2 (11)	C18—C17—H17	120.0 (10)
C6—C5—H5	121.8 (11)	C16—C17—H17	118.7 (10)
C7—C6—C5	118.7 (2)	C17—C18—C19	120.6 (2)
C7—C6—H6	118.2 (12)	C17—C18—H18	119.4 (11)
C5—C6—H6	123.1 (12)	C19—C18—H18	120.0 (11)
C6—C7—C2	122.8 (2)	C20—C19—C18	119.3 (2)
C6—C7—H7	118.4 (11)	C20—C19—H19	120.4 (11)
C2—C7—H7	118.8 (11)	C18—C19—H19	120.3 (11)
C9—C8—C13	119.69 (15)	C19—C20—C15	121.82 (19)
C9—C8—N1	119.96 (15)	C19—C20—H20	118.9 (10)
C13—C8—N1	120.27 (16)	C15—C20—H20	119.1 (10)
C8—N1—C1—O1	−8.7 (3)	C8—C9—C10—C11	−1.0 (3)
C8—N1—C1—C2	171.86 (15)	N3—C9—C10—C11	−178.69 (17)
O1—C1—C2—C7	171.32 (17)	C9—C10—C11—C12	−0.5 (3)
N1—C1—C2—C7	−9.2 (2)	C10—C11—C12—C13	0.3 (3)
O1—C1—C2—C3	−7.1 (3)	C11—C12—C13—C8	1.3 (3)
N1—C1—C2—C3	172.34 (16)	C9—C8—C13—C12	−2.8 (3)
C7—C2—C3—N2	−179.81 (18)	N1—C8—C13—C12	−179.49 (16)
C1—C2—C3—N2	−1.3 (3)	C9—N3—C14—O2	−5.0 (2)
C7—C2—C3—C4	2.6 (3)	C9—N3—C14—C15	175.18 (14)
C1—C2—C3—C4	−178.97 (16)	O2—C14—C15—C20	−165.42 (16)
N2—C3—C4—C5	−178.67 (19)	N3—C14—C15—C20	14.4 (2)
C2—C3—C4—C5	−0.9 (3)	O2—C14—C15—C16	12.8 (2)
C3—C4—C5—C6	−1.2 (3)	N3—C14—C15—C16	−167.37 (15)
C4—C5—C6—C7	1.6 (3)	C20—C15—C16—N4	−176.21 (16)
C5—C6—C7—C2	0.1 (3)	C14—C15—C16—N4	5.5 (3)
C3—C2—C7—C6	−2.2 (3)	C20—C15—C16—C17	1.1 (3)
C1—C2—C7—C6	179.34 (17)	C14—C15—C16—C17	−177.18 (14)
C1—N1—C8—C9	135.32 (18)	N4—C16—C17—C18	177.07 (18)
C1—N1—C8—C13	−48.0 (3)	C15—C16—C17—C18	−0.3 (3)
C13—C8—C9—C10	2.6 (2)	C16—C17—C18—C19	−0.7 (3)
N1—C8—C9—C10	179.31 (16)	C17—C18—C19—C20	0.8 (3)
C13—C8—C9—N3	−179.83 (16)	C18—C19—C20—C15	0.0 (3)
N1—C8—C9—N3	−3.1 (2)	C16—C15—C20—C19	−1.0 (3)
C14—N3—C9—C8	55.6 (2)	C14—C15—C20—C19	177.33 (16)
C14—N3—C9—C10	−126.74 (18)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2	0.849 (17)	1.986 (18)	2.694 (2)	140.4 (17)
N3—H3···O1i	0.86 (2)	2.10 (2)	2.929 (2)	163.0 (17)
N4—H42···O2	0.97 (3)	1.88 (3)	2.646 (3)	134 (2)
N2—H21···O1	0.95 (2)	1.95 (2)	2.667 (2)	130.2 (19)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2	0.849 (17)	1.986 (18)	2.694 (2)	140.4 (17)
N3—H3⋯O1i	0.86 (2)	2.10 (2)	2.929 (2)	163.0 (17)
N4—H42⋯O2	0.97 (3)	1.88 (3)	2.646 (3)	134 (2)
N2—H21⋯O1	0.95 (2)	1.95 (2)	2.667 (2)	130.2 (19)

Symmetry code: (i) .