2,2′-Diamino-N,N′-(o-phenyl­ene)di­benz­amide

Booysen, I.; Gerber, T.I.A.; Hosten, E.; Mayer, P.

doi:10.1107/S1600536809009283

organic compounds

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o850

doi:10.1107/S1600536809009283

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2,2′-Diamino-N,N′-(o-phenylene)dibenzamide

Irvin Booysen,^a Thomas I. A. Gerber,^a ^* Eric Hosten ^a and Peter Mayer ^b

^aDepartment of Chemistry, Nelson Mandela Metropolitan University, 6031 Port Elizabeth, South Africa, and ^bDepartment of Chemistry, Ludiwig-Maximilians University, D-81377 München, Germany
^*Correspondence e-mail: thomas.gerber@nmmu.ac.za

(Received 9 March 2009; accepted 13 March 2009; online 25 March 2009)

In the structure of the title compound, C₂₀H₁₈N₄O₂, 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 phenylenediamine ring. In the crystal, a centrosymmetric dimer is formed by intermolecular N—H⋯O hydrogen bonds, resulting in an R₂²(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_r = 346.38
Monoclinic, P 2₁ /n
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[F² > 2σ(F²)] = 0.047
wR(F²) = 0.122
S = 0.99
3893 reflections
308 parameters
All H-atom parameters refined
Δρ_max = 0.19 e Å⁻³
Δρ_min = −0.20 e Å⁻³

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) -x+1, -y, -z+2.

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 ).

Supporting information

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

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

checkCIF report

Comment top

In the present work the structure of N,N'-(1,2-phenylene)bis(2-aminobenzamide) has been determined to explore its suitability as a tetradentate ligand for various metal ions. The conformations of N—H and C═O bonds in the amide groups are trans to each other (Fig. 1), similar to that observed in other benzamides and benzanilides (Gowda et al., 2003, 2008). Also, the conformations of the amide O atoms are syn to the ortho amino groups in the benzoyl rings. The amide group N1HC1O1 makes dihedral angles of 8.4 (2)° and 51.85 (16)° with the benzoyl and phenylene rings respectively. For the N3HC14O2 group, these values are 13.8 (2)° and 51.19 (17)°. The C2–C7 and C15–C20 benzoyl rings form dihedral angles of 59.64 (17)° and 64.86 (18)° respectively with the phenylene ring.

The conformational arrangement of the rings is mainly determined by intra- and intermolecular hydrogen-bonds. The graph set descriptor for the intramolecular hydrogen bonds is S(6)S(6)S(7) on a unitary level. Centrosymmetric dimers are formed by two intermolecular hydrogen bonds of the type N—H···O resulting in a R²₂(14) descriptor on a unitary level. The hydrogen bonding pattern is shown in Fig. 2.

Related literature top

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 top

The title compound was prepared according to the literature method (Black & Rothnie, 1983). The purity of the compound was checked by determining its melting point. It was characterized by recording its IR and ¹H NMR spectra. Single crystals of the title compound were obtained from a pyridine/ethanol (1:1, v/v) solution.

Computing details top

Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); 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).

Figures top

	Fig. 1. The molecular structure of the title compound (anisotropic displacement ellipsoids drawn at the 50% probability level).
	Fig. 2. Hydrogen bonds (dashed lines) determining the conformational arrangement of the rings. For details of the hydrogen bonds see Table 1.

2,2'-Diamino-N,N'-(o-phenylene)dibenzamide top

Crystal data top

C₂₀H₁₈N₄O₂	F(000) = 728
M_r = 346.38	D_x = 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

Data collection top

Nonius KappaCCD diffractometer	2085 reflections with I > 2σ(I)
Radiation source: rotating anode	R_int = 0.049
MONTEL, graded multilayered X-ray optics monochromator	θ_max = 27.5°, θ_min = 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 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)] = 0.047	All H-atom parameters refined
wR(F²) = 0.122	w = 1/[σ²(F_o²) + (0.0521P)²] where P = (F_o² + 2F_c²)/3
S = 0.99	(Δ/σ)_max = 0.001
3893 reflections	Δρ_max = 0.19 e Å⁻³
308 parameters	Δρ_min = −0.20 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008)
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0130 (17)

Crystal data top

C₂₀H₁₈N₄O₂	V = 1704.69 (12) Å³
M_r = 346.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 8.7464 (3) Å	µ = 0.09 mm⁻¹
b = 14.4308 (6) Å	T = 200 K
c = 13.6161 (6) Å	0.16 × 0.14 × 0.10 mm
β = 97.291 (3)°

Data collection top

Nonius KappaCCD diffractometer	2085 reflections with I > 2σ(I)
7575 measured reflections	R_int = 0.049
3893 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.122	All H-atom parameters refined
S = 0.99	Δρ_max = 0.19 e Å⁻³
3893 reflections	Δρ_min = −0.20 e Å⁻³
308 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₀H₁₈N₄O₂
M_r	346.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	200
a, b, c (Å)	8.7464 (3), 14.4308 (6), 13.6161 (6)
β (°)	97.291 (3)
V (Å³)	1704.69 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.16 × 0.14 × 0.10

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	7575, 3893, 2085
R_int	0.049
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.122, 0.99
No. of reflections	3893
No. of parameters	308
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.20

Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), PLATON (Spek, 2009) and WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y, −z+2.

Acknowledgements

The authors thank Professor P. Klüfers for generous allocation of diffractometer time.

References

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