N—H⋯N hydrogen bonding in 4,6-di­phenyl-2-pyrimidinyl­amine isolated from the plant Justicia secunda (Acanthaceae)

Gallagher, J.F.; Goswami, S.; Chatterjee, B.; Jana, S.; Dutta, K.

doi:10.1107/S0108270104002902

organic compounds

STRUCTURAL
CHEMISTRY

ISSN: 2053-2296

Volume 60| Part 4| April 2004| Pages o229-o231

doi:10.1107/S0108270104002902

N—H⋯N hydrogen bonding in 4,6-diphenyl-2-pyrimidinylamine isolated from the plant Justicia secunda (Acanthaceae)

John F. Gallagher,^a ^* Shyamaprosad Goswami,^b Baidyanath Chatterjee,^b Subrata Jana ^b and Kalyani Dutta ^c

^aSchool of Chemical Sciences, Dublin City University, Dublin 9, Ireland, ^bDepartment of Chemistry, B.E. College (Deemed University), Botanic Garden, Howrah 711 103, West Bengal, India, and ^cDepartment of Chemistry, IIT, Kharagpur, West Bengal, India
^*Correspondence e-mail: john.gallagher@dcu.ie

(Received 24 November 2003; accepted 5 February 2004; online 11 March 2004)

The title compound, C₁₆H₁₃N₃, isolated from Justicia secunda (Acanthaceae), comprises two molecules (which differ slightly in conformation) in the asymmetric unit of space group P $[\overline 1]$ . Intermolecular N_amino—H⋯N_pyrm interactions (N_pyrm is a pyrimidine ring N atom) involve only one of the two donor amino H atoms and pyrimidine N atoms per molecule, forming dimeric units via $[R{_2^2}]$ (8) rings, with N⋯N distances of 3.058 (2) and 3.106 (3) Å, and N—H⋯N angles of 172.7 (18) and 175.8 (17)°. The dimers are linked by C—H⋯π(arene) contacts, with an H⋯centroid distance of 2.77 Å and a C—H⋯centroid angle of 141°.

Comment

The title compound, 4,6-diphenyl-2-pyrimidinylamine, (I), was isolated as a natural product from the plant Justicia secunda (Acanthaceae) collected in Trinidad, West Indies. The parent structure, viz. 4,6-diphenyl-1,2-dihydropyrimidine, has been reported (Weis & Vishkautsan, 1985 ), but the coordinates are not in the Cambridge Structural Database (CSD; Allen, 2002 ) for comparison with (I) (CSD refcode DEZMEA for parent compound).

Compound (I) crystallizes in space group P $[\overline 1]$ (No. 2) with two independent molecules, A and B, in the asymmetric unit, which differ slightly in conformation (Fig. 1). Bond lengths and angles are largely unexceptional and in accord with anticipated values (Orpen et al., 1994 ); selected dimensions are given in Table 1. The central C—N bond lengths range from 1.340 (2) to 1.346 (2) Å, while the aromatic C—C distances are in the range 1.381 (3)–1.387 (3) Å. Torsion-angle differences are evident from analysis of the N1—C4—C21—C26 angles, which are −29.8 (3) and 36.5 (3)° in molecules A and B, respectively (Table 1). Even more dramatic is the difference in dihedral angles between the C11–C16 and C21–C26 planes, which are 52.15 (7) and 31.79 (7)° in molecules A and B, respectively. The weighted (unit weight) r.m.s. fit for the superposition of the non-H atoms in both molecules is 0.65 Å (0.55 Å) (Spek, 2003 ).

Molecules A and B associate in pairs through N_amino—H⋯N_pyrm intermolecular interactions (N_pyrm is a pyrimidine ring N atom), which only involve two of the four amino donor H atoms and N pyrimidine acceptors per A/B pair. The N⋯N distances are 3.058 (2) and 3.106 (3) Å, and the N—H⋯N angles are 172.7 (18) and 175.8 (17)° (Table 2), thus forming a hydrogen-bonded ring with an $[R{_2^2}]$ (8) graph set similar to that observed in centrosymmetric carboxylic acid pairs. A C—H⋯π(arene) contact from C12A—H12A to the C21A–C26A ring links the dimeric units into a dimer of dimers, which is further augmented via a contact from C26A—H26A group to the N1A/N2A/C1A–C4A ring into a one-dimensional stack (Fig. 2 and Table 2). These are the only contacts of note in the structure of (I), apart from the N—H⋯N hydrogen bonding.

Examination of the structure of (I) for interactions involving N2A/N2B reveals that, along the b direction, atom H24A (a potential donor) is 2.99 Å from N2Aⁱ, with a C24A—H24A⋯N2Aⁱ angle of 163° [symmetry code: (i) x, 1 + y, z]. Likewise, the closest N⋯H intermolecular distance involving atom N2B is N2B⋯H24Bⁱ of 3.08 Å, with an N2B⋯H24Bⁱ—C24Bⁱ angle of 155°. Neither of these interactions constitutes a hydrogen bond.

Inspection of Fig. 2 shows the dimeric units in a two-dimensional cross-section through the crystal structure parallel to the [101] plane. In the crystal structure, a more efficient packing could involve dimer formation about inversion centres, which would necessitate rotation of the phenyl rings to align and fulfil symmetry requirements, e.g. the phenyl rings have interplanar angles of 52.12 (7) and 31.79 (7)° in molecules A and B, respectively. The reason why this does not arise is due to the initial hydrogen-bonded dimer formation. Utilization of only half of the N—H⋯N donor/acceptors per A/B hydrogen-bonded dimer prevents the N2A/N2B pair from forming hydrogen bonds, as potential (C)N—H⋯N donor/acceptor pairs cannot approach one another and because of the concurrent formation of unfavourable H⋯H contacts. Interactions in (I) are therefore limited to the two N—H⋯N interactions per A/B pair.

Ab initio calculations on (I) gave results similar to those observed in molecules A and B. Calculations were undertaken at the 6-31⁺G(d) level in the search for a local minimum for comparison with molecules A and B, using GAUSSIAN03 (Frisch et al., 2003 ). The N—C—C—C torsion angles are 27.55°, similar to the value of −29.8 (3)° found in molecule A. The H₂N—C distance is 1.362 Å and the N—C—N angle is 116.79° [range 116.15 (17)–117.05 (17)° in molecule A]. Overall, the calculated results resemble those of molecule A. However, no attempt was made to find the global minimum in the system.

Crystal structures with more than one molecule present in the asymmetric unit are not uncommon (Steiner, 2000 ; Gallagher et al., 1998 ). Recently, Görbitz (2002 , 2003 ) has reported on dipeptide derivatives, e.g. two forms of L-valyl-L-phenylalanine trihydrate (P2₁, Z = 16, Z′ = 8; P2₁2₁2₁, Z = 4, Z′ = 1) and L-methionyl-L-alanine (P6₁, Z = 42, Z′ = 7), which provide rare examples of systems with Z′ = 8 and 7 molecules in their respective asymmetric units, in contrast with Z′ = 2, which is not uncommon. Analysis of the CSD (February 2004, version 5.25; Allen, 2002) reveals a total of 65 935 crystal structures in space group P $[\overline 1]$ (No. 2) (and equivalents with no restrictions), 7625 with Z′ > 1, some 11.6% of the total, and 6775 with Z′ = 2. No attempt was made to examine incorrect space groups.

Figure 1
A view of the two independent molecules in (I

) as a hydrogen-bonded dimer, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.

Figure 2
A view of the dimeric units in (I

) linked by C—H⋯π(arene) interactions. Atoms are depicted as small spheres of arbitrary sizes. The ten phenyl-ring H atoms in molecule B have been omitted for clarity. The centroid labels are as defined in Table 2

, and the centroids labelled with an asterisk (*) or a prime (′) are at symmetry positions (i) and (ii), respectively, given in Table 2

Experimental

The plant Justicia secunda (Acanthaceae) was collected in Trinidad, West Indies, and dried at 308–313 K. A large quantity (1 kg) of this dried powdered plant (except root and flower/fruit) was placed in a large separating funnel and soaked in acetone overnight. The acetone layer was collected and the process repeated until the acetone layer became faintly green in colour. The combined acetone extracts were evaporated and the dry mass extracted with benzene. The benzene-soluble fraction was dried, dissolved in the minimum amount of dry warm CHCl₃ and spread over activated silica gel in a sintered glass Buchner funnel. It was then eluted with 50 ml portions of benzene and then a CHCl₃–benzene mixture (1:4) under a slight vacuum. The fraction obtained from CHCl₃–benzene (1:4) was collected and the solvent removed. It was then subjected to column chromatography with light petroleum (b.p. 313–333 K) and benzene. After concentration, the benzene fraction yielded gummy crystals upon refrigeration. These crystals were further purified by preparative chromatography to afford the pure title compound, (I), as well shaped crystals from CHCl₃.

Crystal data

C₁₆H₁₃N₃
M_r = 247.29
Triclinic, $[P\overline 1]$
a = 7.8263 (9) Å
b = 10.8009 (9) Å
c = 15.7878 (12) Å
α = 83.457 (5)°
β = 77.039 (7)°
γ = 82.326 (7)°
V = 1284.0 (2) Å³
Z = 4
D_x = 1.279 Mg m⁻³
Mo Kα radiation
Cell parameters from 74 reflections
θ = 5.4–17.9°
μ = 0.08 mm⁻¹
T = 294 (1) K
Plate, colourless
0.50 × 0.30 × 0.08 mm

Data collection

Siemens P4 diffractometer
ω/2θ scans
5607 measured reflections
4529 independent reflections
2987 reflections with I > 2σ(I)
R_int = 0.019
θ_max = 25.0°
h = −9 → 1
k = −12 → 12
l = −18 → 18
4 standard reflections every 296 reflections intensity decay: 1%

Refinement

Refinement on F²
R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.119
S = 1.01
4529 reflections
359 parameters
H atoms treated by a mixture of independent and constrained refinement
w = 1/[σ²(F_o²) + (0.055P)² + 0.13P] where P = (F_o² + 2F_c²)/3
(Δ/σ)_max = 0.001
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.17 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

N1A—C1A	1.345 (2)
N1A—C4A	1.346 (2)
N2A—C1A	1.343 (2)
N2A—C2A	1.340 (2)
N4A—C1A	1.357 (2)
C2A—C3A	1.385 (2)
C2A—C11A	1.488 (2)
C3A—C4A	1.384 (2)
C4A—C21A	1.481 (2)
N1B—C1B	1.346 (2)
N1B—C4B	1.343 (2)
N2B—C1B	1.343 (2)
N2B—C2B	1.340 (2)
N4B—C1B	1.347 (2)
C2B—C3B	1.381 (3)
C2B—C11B	1.488 (3)
C3B—C4B	1.387 (3)
C4B—C21B	1.484 (3)

N1A—C1A—N2A	126.76 (17)
N1A—C1A—N4A	117.05 (17)
N2A—C1A—N4A	116.15 (17)
N1B—C1B—N2B	126.72 (17)
N1B—C1B—N4B	116.73 (18)
N2B—C1B—N4B	116.55 (18)

N1A—C4A—C21A—C26A	−29.8 (3)
C3A—C4A—C21A—C26A	151.83 (19)
C3A—C2A—C11A—C12A	149.4 (2)
N1B—C4B—C21B—C26B	−36.5 (3)
C3B—C4B—C21B—C26B	142.9 (2)
C3B—C2B—C11B—C12B	−152.6 (2)

Table 2
Hydrogen-bonding and contact geometry (Å, °) for compound (I)

Cg1 and Cg2 represent the centroids of the rings C21A–C26A and N1A/N2A/C1A–C4A, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N4A—H1A⋯N1B	0.89 (2)	2.17 (2)	3.058 (2)	172.7 (18)
N4B—H2B⋯N1A	0.91 (2)	2.20 (2)	3.106 (3)	175.8 (17)
C12A—H12A⋯Cg1ⁱ	0.93	2.77	3.538 (2)	141
C26A—H26A⋯Cg2ⁱⁱ	0.93	2.78	3.393 (2)	124
Symmetry codes: (i) -x,2-y,1-z; (ii) 1-x,2-y,1-z.

Compound (I) crystallized in the triclinic system, the systematic absences permitting space group P1 or P $[\overline 1]$ ; P $[\overline 1]$ was assumed and confirmed by the analysis. All H atoms bonded to C atoms were treated as riding atoms, with C—H distances of 0.93 Å, while the four amino H atoms were refined with isotropic displacement parameters, giving N—H distances in the range 0.89 (2)–0.91 (2) Å.

Data collection: XSCANS (Siemens, 1996 ); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996 ) and PLATON (Spek, 2003); software used to prepare material for publication: NRCVAX96 (Gabe et al., 1989 ), SHELXL97 and PREP8 (Ferguson, 1998 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S0108270104002902/gd1292sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S0108270104002902/gd1292Isup2.hkl

Comment top

The title compound, 4,6-diphenyl-2-pyrimidinylamine, (I), was isolated as a natural product from the plant Justicia Secunda (Acanthaceae) in Trinidad, West Indies. The parent structure, 4,6-diphenyl-1,2-dihydropyrimidine, has been reported (Weis & Vishkautsan, 1985), but the coordinates are not in the Cambridge Structural Database (CSD; Allen, 2002) for comparison with (I) (CSD refcode DEZMEA). \sch

Compound (I) crystallizes in space group P1 (No. 2) with two independent molecules, A and B, in the asymmetric unit, which differ slightly in conformation (Fig. 1). Bond lengths and angles are largely unexceptional and are in accord with anticipated values (Orpen et al., 1994); selected dimensions are given in Table 1. The central C—N bond lengths are from 1.340 (2) to 1.346 (2) Å, while the aromatic C—C distances are in the range 1.381 (3)–1.387 (3) Å. Torsion-angle differences are evident from analysis of the N1—C4—C21—C26 angles, which are −29.8 (3) and 36.5 (3)° in molecules A and B, respectively (Table 1). Even more dramatic is the difference in dihedral angles between the C11—C16 and C21—C26 planes, at 52.15 (7) and 31.79 (7)° in A and B, respectively. The weighted (unit weight) r.m.s. fit for the superposition of the non-H atoms in both molecules is 0.65(0.55) Å (Spek, 2003).

Molecules A and B associate in pairs through N_amino—H···N_pyrm intermolecular interactions, which only involve two of the four amino donor H atoms and N pyrimidine acceptors per A/B pair. The N···N distances are 3.058 (2) and 3.106 (3) Å and the N—H···N angles 172.7 (18) and 175.8 (17)° (Table 2), thus forming a hydrogen-bonded ring with an R₂²(8) graph set similar to that observed in centrosymmetric carboxylic acid pairs. A C—H···π(arene) contact from C12A—H12A to the C21A—C26A ring links the dimeric units into a dimer of dimers, which is further augmented, by a contact from C26A—H26A to the N1A/N2A/C1A—C4A ring, into a one-dimensional stack (Fig. 2, Table 2). These are the only contacts of note in the structure of (I), apart from the N—H···N hydrogen bonding.

Examination of the structure of (I) for interactions involving N2A/N2B reveals that, along the b direction, atom H24A (a potential donor) is 2.99 Å from N2Aⁱ, with C24A—H24A···N2Aⁱ 163° [symmetry code: (i) x, 1 + y, z]. Likewise, the closest N···H intermolecular distance involving atom N2B is N2B···H24Bⁱ of 3.08 Å, with N2B···H24Bⁱ—C24Bⁱ 155°. Neither of these constitutes a hydrogen bond.

Inspection of Fig. 2 shows the dimeric units in a two-dimensional cross section through the crystal structure parallel to the [101] plane. In the crystal structure packing, a more efficient packing could involve dimeric formation about inversion centres, which would necessitate rotation of the phenyl rings to align and fulfil symmetry requirements, e.g. the phenyl rings have interplanar angles of 52.12 (7) and 31.79 (7)° in A and B, respectively. The reason why this does not arise is due to the initial hydrogen-bonded dimer formation. Utilization of only half of the N—H/N donor/acceptors per A/B hydrogen-bonded dimer prevents the N2A/N2B pair from forming hydrogen bonds, as potential (C)N—H/N donor/acceptor pairs cannot approach one another, and largely due to the concurrent formation of H···H contacts Please clarify to what this last clause refers. Interactions in (I) are therefore limited to the two N—H···N per A/B pair.

Ab initio calculations on the 4,6-diphenyl-2-pyrimidinylamine system, (I), gave results similar to that observed in the A/B molecules. Calculations were undertaken at the 6–31⁺G(d) level in the search for a local minimum for comparison with the A/B molecules, using GAUSSIAN03 (Frisch et al., 2003). The N—C—C—C torsion angles are 27.55°, similar to the value of −29.8 (3)° in A. The H₂N—C distance is 1.362 Å and the N—C—N angle is 116.79° [range 116.15 (17)–117.05 (17)° in molecule A]. Overall, the calculation result resembles molecule A. However, no attempt was made to find the global minimum in the system.

Crystal structures with more than one molecule present in the asymmetric unit are not uncommon (Steiner, 2000; Gallagher et al., 1998). Recently, Görbitz (2002, 2003) has reported on dipeptide derivatives, e.g. the two forms of L-valyl-L-phenylalanine trihydrate (P2₁, Z = 16, Z' = 8, and P2₁2₁2₁, Z = 4, Z' = 1) and L-methionyl-L-alanine (P6₁, Z = 42, Z' = 7), which provide rare examples of systems with Z' = 8 and 7 molecules in their respective asymmetric units, in contrast with Z' = 2 which is not uncommon. Analysis of the CSD (February 2004, version 5.25; Allen, 2002) reveals a total of 65935 crystal structures in space group P1 (No. 2) (and equivalents with no restrictions), 7625 with Z' > 1, some 11.6% of the total, and 6775 with Z'= 2. No attempt was made to examine incorrect space groups.

Table 2. Hydrogen-bond and contact data (Å, °) for compound (I). Cg1 and Cg2 represent the centroids of the rings C21A—C26A and N1A/N2A/C1A—C4A, respectively.

Experimental top

The plant Justicia Secunda (Acanthaceae) was collected from Trinidad, West Indies, and dried at 308–313 K. A large quantity (1 kg) of this dried powdered plant (except root and flower/fruit) was placed in a large separating funnel and soaked in acetone overnight. The acetone layer was collected and the process was repeated until the acetone layer became faint green in colour. The combined acetone extracts were evaporated and the dry mass was extracted with benzene. The benzene-soluble fraction was dried, dissolved in the minimum amount of dry warm CHCl₃ and spread over activated silica gel in a sintered glass Buchner funnel. It was then eluted with 50 ml portions of benzene and then a CHCl₃:benzene mixture (1:4) under a slight vacuum. The fraction obtained from CHCl₃:benzene (1:4) was collected and the solvent removed. It was then subjected to column chromatography with light petroleum (b.p. 313–333 K) and benzene. After concentration, the benzene fraction yielded gummy crystals upon refrigeration. These crystals were further purified by preparative chromatography to afford the pure compound, (I), as well shaped crystals from CHCl₃.

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003); software used to prepare material for publication: NRCVAX96 (Gabe et al., 1989), SHELXL97 and PREP8 (Ferguson, 1998).

Figures top

	Fig. 1. A view of molecules in (I) as a hydrogen-bonded dimer, with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the dimeric units in (I) linked by C—H···π(arene) interactions. Atoms are depicted as small spheres of an arbitrary size. The ten phenyl-ring H atoms in molecule B have been omitted for clarity. The centroid labels are as defined in Table 2. Atoms labelled with an asterisk (*) or a prime (') are at symmetry positions (i) and (ii), respectively, as given in Table 2.

4,6-diphenyl-2-pyrimidinylamine top

Crystal data top

C₁₆H₁₃N₃	Z = 4
M_r = 247.29	F(000) = 520
Triclinic, P1	D_x = 1.279 Mg m⁻³
Hall symbol: -P 1	Melting point: 408 K
a = 7.8263 (9) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.8009 (9) Å	Cell parameters from 74 reflections
c = 15.7878 (12) Å	θ = 5.4–17.9°
α = 83.457 (5)°	µ = 0.08 mm⁻¹
β = 77.039 (7)°	T = 294 K
γ = 82.326 (7)°	Plate, colourless
V = 1284.0 (2) Å³	0.50 × 0.30 × 0.08 × not measured (radius) mm

Data collection top

Siemens P4 diffractometer	R_int = 0.019
Radiation source: X-ray tube	θ_max = 25.0°, θ_min = 1.9°
Graphite monochromator	h = −9→1
ω/2θ scans	k = −12→12
5607 measured reflections	l = −18→18
4529 independent reflections	4 standard reflections every 296 reflections
2987 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.047	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	w = 1/[σ²(F_o²) + (0.055P)² + 0.13P] where P = (F_o² + 2F_c²)/3
4529 reflections	(Δ/σ)_max = 0.001
359 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₁₆H₁₃N₃	γ = 82.326 (7)°
M_r = 247.29	V = 1284.0 (2) Å³
Triclinic, P1	Z = 4
a = 7.8263 (9) Å	Mo Kα radiation
b = 10.8009 (9) Å	µ = 0.08 mm⁻¹
c = 15.7878 (12) Å	T = 294 K
α = 83.457 (5)°	0.50 × 0.30 × 0.08 × not measured (radius) mm
β = 77.039 (7)°

Data collection top

Siemens P4 diffractometer	R_int = 0.019
5607 measured reflections	4 standard reflections every 296 reflections
4529 independent reflections	intensity decay: 1%
2987 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.119	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.18 e Å⁻³
4529 reflections	Δρ_min = −0.17 e Å⁻³
359 parameters

Special details top

Geometry. Gaussian '03 reference ======================

M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 2003.

Torsional angles #===============

Dihedral angle NCCC

−29.81 (26) N1A–C4A–C21A–C26A −36.46 (27) N1B–C4B–C21B–C26B 154.15 (18) N2A–C2A–C11A–C16A −152.50 (19) N2B–C2B–C11B–C16B

Dihedral angle CCCC

106.98 (22) C12A–C11A–C21A–C22A −170.55 (24) C12B–C11B–C21B–C22B 1.34 (32) C14A–C2A–C4A–C24A −1.40 (34) C14B–C2B–C4B–C24B

Mean plane data ex-SHELXL97 for molecule (I) ############################################

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

-5.8182(0.0047)x + 6.0658(0.0079)y − 2.5280(0.0137)z = 2.8570(0.0128)

* 0.0067 (0.0013) C11A * −0.0072 (0.0014) C12A * 0.0012 (0.0015) C13A * 0.0053 (0.0016) C14A * −0.0057 (0.0016) C15A * −0.0003 (0.0015) C16A

Rms deviation of fitted atoms = 0.0051

7.2778(0.0022)x − 1.3368(0.0077)y + 7.0895(0.0113)z = 4.0232(0.0104)

Angle to previous plane (with approximate e.s.d.) = 29.31 (8)

* 0.0120 (0.0013) C1A * −0.0045 (0.0013) C2A * 0.0136 (0.0013) C3A * −0.0108 (0.0013) C4A * −0.0020 (0.0012) N1A * −0.0082 (0.0012) N2A 0.0009 (0.0029) N4A

Rms deviation of fitted atoms = 0.0095

5.4509(0.0048)x + 0.0533(0.0089)y + 13.2611(0.0074)z = 8.3696(0.0127)

Angle to previous plane (with approximate e.s.d.) = 30.48 (8)

* −0.0048 (0.0013) C21A * 0.0072 (0.0014) C22A * −0.0026 (0.0016) C23A * −0.0045 (0.0015) C24A * 0.0068 (0.0015) C25A * −0.0021 (0.0014) C26A

Rms deviation of fitted atoms = 0.0050

−5.8182(0.0047)x + 6.0658(0.0079)y − 2.5280(0.0137)z = 2.8570(0.0128)

Angle to previous plane (with approximate e.s.d.) = 52.15 (7)

* 0.0067 (0.0013) C11A * −0.0072 (0.0014) C12A * 0.0012 (0.0015) C13A * 0.0053 (0.0016) C14A * −0.0057 (0.0016) C15A * −0.0003 (0.0015) C16A

Rms deviation of fitted atoms = 0.0051

−6.9426(0.0035)x + 3.6543(0.0097)y − 2.9128(0.0142)z = 2.8663(0.0190)

Angle to previous plane (with approximate e.s.d.) = 14.50 (11)

* −0.0005 (0.0014) C11B * 0.0078 (0.0015) C12B * −0.0089 (0.0017) C13B * 0.0028 (0.0017) C14B * 0.0045 (0.0016) C15B * −0.0056 (0.0015) C16B

Rms deviation of fitted atoms = 0.0058

7.5633(0.0019)x + 0.8967(0.0086)y + 7.2350(0.0118)z = 6.2720(0.0176)

Angle to previous plane (with approximate e.s.d.) = 27.74 (6)

* −0.0114 (0.0014) C1B * 0.0099 (0.0014) C2B * −0.0051 (0.0014) C3B * −0.0071 (0.0013) C4B * 0.0153 (0.0013) N1B * −0.0015 (0.0013) N2B −0.0378 (0.0033) N4B

Rms deviation of fitted atoms = 0.0095

−7.1932(0.0030)x − 0.2947(0.0097)y + 2.7303(0.0144)z = 5.5969(0.0173)

Angle to previous plane (with approximate e.s.d.) = 37.24 (5)

* −0.0060 (0.0014) C21B * −0.0018 (0.0016) C22B * 0.0059 (0.0017) C23B * −0.0022 (0.0017) C24B * −0.0056 (0.0016) C25B * 0.0097 (0.0015) C26B

Rms deviation of fitted atoms = 0.0058

−6.9426(0.0035)x + 3.6543(0.0097)y − 2.9128(0.0142)z = 2.8663(0.0190)

Angle to previous plane (with approximate e.s.d.) = 31.79 (7)

* −0.0005 (0.0014) C11B * 0.0078 (0.0015) C12B * −0.0089 (0.0017) C13B * 0.0028 (0.0017) C14B * 0.0045 (0.0016) C15B * −0.0056 (0.0015) C16B

Rms deviation of fitted atoms = 0.0058

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

	x	y	z	U_iso*/U_eq
N1A	0.2906 (2)	0.98395 (14)	0.45438 (9)	0.0400 (4)
N2A	0.1831 (2)	0.79337 (13)	0.52793 (10)	0.0414 (4)
N4A	0.3263 (3)	0.80359 (18)	0.38421 (12)	0.0534 (5)
C1A	0.2662 (2)	0.86235 (17)	0.45848 (12)	0.0398 (5)
C2A	0.1229 (2)	0.85133 (16)	0.60125 (11)	0.0379 (4)
C3A	0.1455 (3)	0.97573 (17)	0.60400 (12)	0.0431 (5)
C4A	0.2277 (2)	1.04082 (16)	0.52846 (12)	0.0380 (4)
C11A	0.0241 (2)	0.77766 (16)	0.67766 (12)	0.0409 (5)
C12A	−0.0673 (3)	0.68216 (17)	0.66437 (13)	0.0457 (5)
C13A	−0.1672 (3)	0.61669 (19)	0.73382 (14)	0.0562 (6)
C14A	−0.1751 (3)	0.6447 (2)	0.81763 (15)	0.0627 (6)
C15A	−0.0830 (3)	0.7372 (2)	0.83208 (14)	0.0619 (6)
C16A	0.0159 (3)	0.80401 (19)	0.76258 (13)	0.0534 (5)
C21A	0.2457 (2)	1.17614 (16)	0.52505 (11)	0.0377 (4)
C22A	0.1199 (3)	1.25391 (17)	0.57738 (12)	0.0468 (5)
C23A	0.1299 (3)	1.38105 (19)	0.57199 (14)	0.0562 (6)
C24A	0.2672 (3)	1.4328 (2)	0.51521 (15)	0.0595 (6)
C25A	0.3950 (3)	1.3568 (2)	0.46384 (14)	0.0569 (6)
C26A	0.3841 (3)	1.22946 (18)	0.46815 (12)	0.0464 (5)
N4B	0.4727 (3)	1.10820 (19)	0.27553 (13)	0.0658 (6)
N1B	0.5567 (2)	0.91786 (14)	0.21871 (10)	0.0446 (4)
N2B	0.6145 (2)	1.11152 (14)	0.13196 (10)	0.0487 (4)
C1B	0.5502 (3)	1.04366 (18)	0.20622 (12)	0.0458 (5)
C2B	0.6895 (3)	1.04656 (17)	0.06315 (12)	0.0426 (5)
C3B	0.6976 (3)	0.91746 (17)	0.06856 (12)	0.0464 (5)
C4B	0.6286 (2)	0.85520 (17)	0.14819 (12)	0.0422 (5)
C11B	0.7655 (3)	1.12079 (17)	−0.01874 (12)	0.0443 (5)
C12B	0.8234 (3)	1.23583 (19)	−0.01535 (14)	0.0543 (6)
C13B	0.8942 (3)	1.3053 (2)	−0.09111 (16)	0.0643 (6)
C14B	0.9032 (3)	1.2623 (2)	−0.17068 (16)	0.0689 (7)
C15B	0.8456 (3)	1.1497 (2)	−0.17527 (14)	0.0641 (6)
C16B	0.7778 (3)	1.0784 (2)	−0.09973 (13)	0.0533 (5)
C21B	0.6333 (3)	0.71662 (17)	0.15886 (12)	0.0444 (5)
C22B	0.6101 (3)	0.65153 (19)	0.09227 (14)	0.0573 (6)
C23B	0.6179 (3)	0.5226 (2)	0.10172 (17)	0.0677 (7)
C24B	0.6505 (3)	0.4568 (2)	0.17753 (17)	0.0679 (7)
C25B	0.6736 (3)	0.5198 (2)	0.24393 (15)	0.0617 (6)
C26B	0.6631 (3)	0.64968 (18)	0.23587 (13)	0.0517 (5)
H1A	0.397 (3)	0.8411 (18)	0.3389 (13)	0.052 (6)*
H2A	0.326 (3)	0.721 (2)	0.3912 (15)	0.076 (8)*
H1B	0.448 (3)	1.190 (2)	0.2646 (14)	0.067 (7)*
H2B	0.418 (3)	1.0687 (18)	0.3265 (14)	0.054 (6)*
H3A	0.1063	1.0147	0.6555	0.052*
H12A	−0.0610	0.6622	0.6079	0.055*
H13A	−0.2290	0.5538	0.7241	0.067*
H14A	−0.2429	0.6009	0.8646	0.075*
H15A	−0.0873	0.7550	0.8888	0.074*
H16A	0.0772	0.8669	0.7728	0.064*
H22A	0.0273	1.2196	0.6167	0.056*
H23A	0.0436	1.4319	0.6069	0.067*
H24A	0.2739	1.5186	0.5114	0.071*
H25A	0.4891	1.3915	0.4260	0.068*
H26A	0.4702	1.1792	0.4326	0.056*
H3B	0.7481	0.8734	0.0201	0.056*
H12B	0.8145	1.2664	0.0384	0.065*
H13B	0.9356	1.3812	−0.0882	0.077*
H14B	0.9487	1.3100	−0.2216	0.083*
H15B	0.8520	1.1209	−0.2294	0.077*
H16B	0.7403	1.0014	−0.1033	0.064*
H22B	0.5890	0.6953	0.0407	0.069*
H23B	0.6011	0.4799	0.0568	0.081*
H24B	0.6568	0.3698	0.1836	0.081*
H25B	0.6965	0.4752	0.2949	0.074*
H26B	0.6759	0.6919	0.2818	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0424 (9)	0.0397 (9)	0.0362 (9)	−0.0074 (7)	−0.0027 (7)	−0.0043 (7)
N2A	0.0437 (9)	0.0400 (9)	0.0388 (9)	−0.0081 (7)	−0.0023 (8)	−0.0052 (7)
N4A	0.0684 (13)	0.0465 (11)	0.0400 (11)	−0.0141 (10)	0.0076 (9)	−0.0107 (9)
C1A	0.0409 (11)	0.0408 (11)	0.0364 (10)	−0.0054 (9)	−0.0042 (9)	−0.0057 (9)
C2A	0.0378 (11)	0.0381 (10)	0.0368 (10)	−0.0038 (8)	−0.0057 (9)	−0.0046 (8)
C3A	0.0526 (12)	0.0400 (11)	0.0341 (10)	−0.0068 (9)	−0.0016 (9)	−0.0058 (8)
C4A	0.0380 (11)	0.0379 (10)	0.0382 (10)	−0.0045 (8)	−0.0076 (9)	−0.0042 (8)
C11A	0.0430 (11)	0.0360 (10)	0.0397 (11)	−0.0026 (9)	−0.0034 (9)	0.0002 (8)
C12A	0.0505 (12)	0.0379 (11)	0.0462 (11)	−0.0046 (9)	−0.0062 (10)	−0.0021 (9)
C13A	0.0618 (14)	0.0419 (11)	0.0608 (14)	−0.0119 (10)	−0.0033 (11)	0.0009 (10)
C14A	0.0702 (16)	0.0513 (13)	0.0532 (14)	−0.0074 (12)	0.0075 (12)	0.0109 (11)
C15A	0.0799 (17)	0.0623 (14)	0.0371 (12)	−0.0054 (13)	−0.0026 (11)	−0.0003 (10)
C16A	0.0687 (15)	0.0500 (12)	0.0408 (12)	−0.0103 (11)	−0.0090 (11)	−0.0028 (9)
C21A	0.0432 (11)	0.0381 (10)	0.0335 (10)	−0.0091 (9)	−0.0102 (9)	−0.0011 (8)
C22A	0.0551 (13)	0.0404 (11)	0.0428 (11)	−0.0079 (10)	−0.0047 (10)	−0.0038 (9)
C23A	0.0710 (15)	0.0426 (12)	0.0547 (13)	−0.0037 (11)	−0.0115 (12)	−0.0094 (10)
C24A	0.0851 (18)	0.0393 (12)	0.0617 (14)	−0.0187 (12)	−0.0265 (13)	−0.0001 (11)
C25A	0.0640 (15)	0.0577 (14)	0.0533 (13)	−0.0290 (12)	−0.0132 (11)	0.0041 (11)
C26A	0.0482 (12)	0.0492 (12)	0.0439 (11)	−0.0135 (10)	−0.0095 (10)	−0.0033 (9)
N1B	0.0515 (10)	0.0420 (9)	0.0372 (9)	−0.0037 (8)	−0.0034 (8)	−0.0043 (7)
N2B	0.0606 (11)	0.0427 (9)	0.0376 (9)	−0.0063 (8)	0.0011 (8)	−0.0038 (8)
N4B	0.1016 (17)	0.0440 (12)	0.0395 (11)	−0.0028 (11)	0.0087 (11)	−0.0059 (9)
C1B	0.0541 (13)	0.0433 (11)	0.0361 (11)	−0.0027 (10)	−0.0017 (10)	−0.0065 (9)
C2B	0.0419 (11)	0.0448 (11)	0.0385 (11)	−0.0033 (9)	−0.0046 (9)	−0.0022 (9)
C3B	0.0543 (13)	0.0429 (11)	0.0362 (11)	0.0000 (10)	0.0007 (9)	−0.0063 (9)
C4B	0.0408 (11)	0.0445 (11)	0.0396 (11)	−0.0029 (9)	−0.0061 (9)	−0.0040 (9)
C11B	0.0437 (12)	0.0442 (11)	0.0393 (11)	−0.0006 (9)	−0.0007 (9)	−0.0005 (9)
C12B	0.0607 (14)	0.0488 (12)	0.0497 (13)	−0.0059 (11)	−0.0057 (11)	−0.0005 (10)
C13B	0.0643 (15)	0.0529 (13)	0.0692 (16)	−0.0151 (12)	−0.0027 (13)	0.0082 (12)
C14B	0.0619 (16)	0.0781 (17)	0.0542 (15)	−0.0091 (13)	0.0020 (12)	0.0199 (13)
C15B	0.0683 (16)	0.0774 (16)	0.0403 (12)	−0.0095 (13)	−0.0007 (11)	0.0014 (11)
C16B	0.0566 (13)	0.0573 (13)	0.0427 (12)	−0.0087 (11)	−0.0035 (10)	−0.0019 (10)
C21B	0.0434 (12)	0.0394 (11)	0.0456 (12)	−0.0026 (9)	−0.0008 (9)	−0.0035 (9)
C22B	0.0690 (15)	0.0501 (13)	0.0531 (13)	−0.0037 (11)	−0.0132 (12)	−0.0085 (10)
C23B	0.0787 (17)	0.0479 (13)	0.0796 (17)	−0.0068 (12)	−0.0177 (14)	−0.0172 (12)
C24B	0.0706 (17)	0.0415 (12)	0.0856 (18)	−0.0064 (12)	−0.0057 (14)	−0.0020 (13)
C25B	0.0654 (15)	0.0502 (13)	0.0601 (14)	−0.0036 (11)	−0.0021 (12)	0.0094 (11)
C26B	0.0546 (13)	0.0482 (12)	0.0464 (12)	−0.0045 (10)	−0.0005 (10)	−0.0017 (10)

Geometric parameters (Å, º) top

N1A—C1A	1.345 (2)	N1B—C1B	1.346 (2)
N1A—C4A	1.346 (2)	N1B—C4B	1.343 (2)
N2A—C1A	1.343 (2)	N2B—C1B	1.343 (2)
N2A—C2A	1.340 (2)	N2B—C2B	1.340 (2)
N4A—C1A	1.357 (2)	N4B—C1B	1.347 (2)
C2A—C3A	1.385 (2)	C2B—C3B	1.381 (3)
C2A—C11A	1.488 (2)	C2B—C11B	1.488 (3)
C3A—C4A	1.384 (2)	C3B—C4B	1.387 (3)
C4A—C21A	1.481 (2)	C4B—C21B	1.484 (3)
C11A—C16A	1.388 (3)	C11B—C16B	1.386 (3)
C11A—C12A	1.390 (3)	C11B—C12B	1.389 (3)
C12A—C13A	1.378 (3)	C12B—C13B	1.382 (3)
C13A—C14A	1.377 (3)	C13B—C14B	1.372 (3)
C14A—C15A	1.374 (3)	C14B—C15B	1.368 (3)
C15A—C16A	1.382 (3)	C15B—C16B	1.383 (3)
C21A—C26A	1.387 (3)	C21B—C22B	1.386 (3)
C21A—C22A	1.389 (2)	C21B—C26B	1.392 (3)
C22A—C23A	1.378 (3)	C22B—C23B	1.378 (3)
C23A—C24A	1.373 (3)	C23B—C24B	1.377 (3)
C24A—C25A	1.378 (3)	C24B—C25B	1.369 (3)
C25A—C26A	1.383 (3)	C25B—C26B	1.387 (3)
N4A—H1A	0.89 (2)	N4B—H1B	0.89 (2)
N4A—H2A	0.89 (2)	N4B—H2B	0.91 (2)
C3A—H3A	0.9300	C3B—H3B	0.9300
C12A—H12A	0.9300	C12B—H12B	0.9300
C13A—H13A	0.9300	C13B—H13B	0.9300
C14A—H14A	0.9300	C14B—H14B	0.9300
C15A—H15A	0.9300	C15B—H15B	0.9300
C16A—H16A	0.9300	C16B—H16B	0.9300
C22A—H22A	0.9300	C22B—H22B	0.9300
C23A—H23A	0.9300	C23B—H23B	0.9300
C24A—H24A	0.9300	C24B—H24B	0.9300
C25A—H25A	0.9300	C25B—H25B	0.9300
C26A—H26A	0.9300	C26B—H26B	0.9300

C1A—N1A—C4A	116.02 (15)	C1B—N1B—C4B	115.96 (16)
C1A—N2A—C2A	116.30 (15)	C1B—N2B—C2B	116.09 (16)
N1A—C1A—N2A	126.76 (17)	N1B—C1B—N2B	126.72 (17)
N1A—C1A—N4A	117.05 (17)	N1B—C1B—N4B	116.73 (18)
N2A—C1A—N4A	116.15 (17)	N2B—C1B—N4B	116.55 (18)
N2A—C2A—C3A	121.13 (17)	N2B—C2B—C3B	121.59 (17)
N2A—C2A—C11A	116.88 (16)	N2B—C2B—C11B	116.43 (17)
C3A—C2A—C11A	121.94 (17)	C3B—C2B—C11B	121.98 (18)
C2A—C3A—C4A	118.63 (17)	C2B—C3B—C4B	118.26 (18)
N1A—C4A—C3A	121.11 (16)	N1B—C4B—C3B	121.32 (17)
N1A—C4A—C21A	117.32 (16)	N1B—C4B—C21B	117.49 (16)
C3A—C4A—C21A	121.56 (17)	C3B—C4B—C21B	121.19 (17)
C12A—C11A—C2A	119.64 (17)	C12B—C11B—C2B	120.26 (18)
C16A—C11A—C2A	121.73 (18)	C16B—C11B—C2B	121.24 (18)
C12A—C11A—C16A	118.59 (18)	C16B—C11B—C12B	118.49 (18)
C11A—C12A—C13A	120.85 (19)	C11B—C12B—C13B	120.6 (2)
C12A—C13A—C14A	119.8 (2)	C12B—C13B—C14B	119.9 (2)
C13A—C14A—C15A	120.1 (2)	C13B—C14B—C15B	120.2 (2)
C14A—C15A—C16A	120.3 (2)	C14B—C15B—C16B	120.2 (2)
C15A—C16A—C11A	120.3 (2)	C15B—C16B—C11B	120.5 (2)
C22A—C21A—C4A	120.32 (17)	C22B—C21B—C4B	120.76 (18)
C26A—C21A—C4A	121.40 (17)	C26B—C21B—C4B	120.34 (18)
C22A—C21A—C26A	118.25 (17)	C22B—C21B—C26B	118.89 (18)
C21A—C22A—C23A	121.08 (19)	C21B—C22B—C23B	120.6 (2)
C22A—C23A—C24A	120.1 (2)	C22B—C23B—C24B	120.1 (2)
C23A—C24A—C25A	119.64 (19)	C23B—C24B—C25B	119.9 (2)
C24A—C25A—C26A	120.4 (2)	C24B—C25B—C26B	120.6 (2)
C25A—C26A—C21A	120.4 (2)	C25B—C26B—C21B	119.8 (2)
C2A—C3A—H3A	120.7	C2B—C3B—H3B	120.9
C4A—C3A—H3A	120.7	C4B—C3B—H3B	120.9
C13A—C12A—H12A	119.6	C13B—C12B—H12B	119.7
C11A—C12A—H12A	119.6	C11B—C12B—H12B	119.7
C14A—C13A—H13A	120.1	C14B—C13B—H13B	120.0
C12A—C13A—H13A	120.1	C12B—C13B—H13B	120.0
C15A—C14A—H14A	119.9	C15B—C14B—H14B	119.9
C13A—C14A—H14A	119.9	C13B—C14B—H14B	119.9
C14A—C15A—H15A	119.9	C14B—C15B—H15B	119.9
C16A—C15A—H15A	119.9	C16B—C15B—H15B	119.9
C15A—C16A—H16A	119.8	C15B—C16B—H16B	119.7
C11A—C16A—H16A	119.8	C11B—C16B—H16B	119.7
C23A—C22A—H22A	119.5	C23B—C22B—H22B	119.7
C21A—C22A—H22A	119.5	C21B—C22B—H22B	119.7
C24A—C23A—H23A	119.9	C24B—C23B—H23B	119.9
C22A—C23A—H23A	119.9	C22B—C23B—H23B	119.9
C23A—C24A—H24A	120.2	C23B—C24B—H24B	120.1
C25A—C24A—H24A	120.2	C25B—C24B—H24B	120.1
C24A—C25A—H25A	119.8	C24B—C25B—H25B	119.7
C26A—C25A—H25A	119.8	C26B—C25B—H25B	119.7
C25A—C26A—H26A	119.8	C25B—C26B—H26B	120.1
C21A—C26A—H26A	119.8	C21B—C26B—H26B	120.1
C1A—N4A—H1A	119.5 (13)	C1B—N4B—H1B	116.3 (14)
C1A—N4A—H2A	114.8 (15)	C1B—N4B—H2B	121.1 (12)
H1A—N4A—H2A	122 (2)	H1B—N4B—H2B	119.8 (19)

N1A—C4A—C21A—C26A	−29.8 (3)	N1B—C4B—C21B—C26B	−36.5 (3)
C3A—C4A—C21A—C26A	151.83 (19)	C3B—C4B—C21B—C26B	142.9 (2)
C3A—C2A—C11A—C12A	149.4 (2)	C3B—C2B—C11B—C12B	−152.6 (2)
C2A—N2A—C1A—N1A	−2.0 (3)	C2B—N2B—C1B—N1B	1.4 (3)
C2A—N2A—C1A—N4A	−179.66 (17)	C2B—N2B—C1B—N4B	−179.29 (19)
C4A—N1A—C1A—N2A	1.4 (3)	C4B—N1B—C1B—N2B	−3.0 (3)
C4A—N1A—C1A—N4A	179.04 (17)	C4B—N1B—C1B—N4B	177.69 (19)
C1A—N2A—C2A—C3A	0.3 (3)	C1B—N2B—C2B—C3B	0.8 (3)
C1A—N2A—C2A—C11A	177.57 (17)	C1B—N2B—C2B—C11B	−178.38 (18)
N2A—C2A—C3A—C4A	1.8 (3)	N2B—C2B—C3B—C4B	−1.2 (3)
C11A—C2A—C3A—C4A	−175.34 (17)	C11B—C2B—C3B—C4B	177.94 (18)
C1A—N1A—C4A—C3A	0.9 (3)	C1B—N1B—C4B—C3B	2.4 (3)
C1A—N1A—C4A—C21A	−177.45 (16)	C1B—N1B—C4B—C21B	−178.26 (17)
C2A—C3A—C4A—N1A	−2.5 (3)	C2B—C3B—C4B—N1B	−0.5 (3)
C2A—C3A—C4A—C21A	175.85 (17)	C2B—C3B—C4B—C21B	−179.81 (18)
N2A—C2A—C11A—C16A	154.15 (18)	N2B—C2B—C11B—C16B	−152.50 (19)
C3A—C2A—C11A—C16A	−28.6 (3)	C3B—C2B—C11B—C16B	28.3 (3)
N2A—C2A—C11A—C12A	−27.9 (3)	N2B—C2B—C11B—C12B	26.5 (3)
C16A—C11A—C12A—C13A	1.4 (3)	C16B—C11B—C12B—C13B	−1.0 (3)
C2A—C11A—C12A—C13A	−176.68 (18)	C2B—C11B—C12B—C13B	180.0 (2)
C11A—C12A—C13A—C14A	−0.9 (3)	C11B—C12B—C13B—C14B	1.8 (3)
C12A—C13A—C14A—C15A	−0.3 (3)	C12B—C13B—C14B—C15B	−1.3 (4)
C13A—C14A—C15A—C16A	1.0 (3)	C13B—C14B—C15B—C16B	0.0 (4)
C14A—C15A—C16A—C11A	−0.5 (3)	C14B—C15B—C16B—C11B	0.8 (3)
C12A—C11A—C16A—C15A	−0.7 (3)	C12B—C11B—C16B—C15B	−0.3 (3)
C2A—C11A—C16A—C15A	177.30 (19)	C2B—C11B—C16B—C15B	178.7 (2)
N1A—C4A—C21A—C22A	148.11 (18)	N1B—C4B—C21B—C22B	144.24 (19)
C3A—C4A—C21A—C22A	−30.3 (3)	C3B—C4B—C21B—C22B	−36.4 (3)
C26A—C21A—C22A—C23A	1.2 (3)	C26B—C21B—C22B—C23B	−0.6 (3)
C4A—C21A—C22A—C23A	−176.82 (19)	C4B—C21B—C22B—C23B	178.7 (2)
C21A—C22A—C23A—C24A	−1.0 (3)	C21B—C22B—C23B—C24B	−0.6 (4)
C22A—C23A—C24A—C25A	−0.2 (3)	C22B—C23B—C24B—C25B	0.6 (4)
C23A—C24A—C25A—C26A	1.1 (3)	C23B—C24B—C25B—C26B	0.5 (4)
C24A—C25A—C26A—C21A	−0.9 (3)	C24B—C25B—C26B—C21B	−1.6 (3)
C22A—C21A—C26A—C25A	−0.3 (3)	C22B—C21B—C26B—C25B	1.7 (3)
C4A—C21A—C26A—C25A	177.71 (18)	C4B—C21B—C26B—C25B	−177.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H1A···N1B	0.89 (2)	2.17 (2)	3.058 (2)	172.7 (18)
N4B—H2B···N1A	0.91 (2)	2.20 (2)	3.106 (3)	175.8 (17)
C12A—H12A···Cg1ⁱ	0.93	2.77	3.538 (2)	141
C26A—H26A···Cg2ⁱⁱ	0.93	2.78	3.393 (2)	124

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₃N₃
M_r	247.29
Crystal system, space group	Triclinic, P1
Temperature (K)	294
a, b, c (Å)	7.8263 (9), 10.8009 (9), 15.7878 (12)
α, β, γ (°)	83.457 (5), 77.039 (7), 82.326 (7)
V (Å³)	1284.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.50 × 0.30 × 0.08 × not measured (radius)

Data collection
Diffractometer	Siemens P4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5607, 4529, 2987
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.119, 1.01
No. of reflections	4529
No. of parameters	359
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.18, −0.17

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEPIII (Burnett & Johnson, 1996) and PLATON (Spek, 2003), NRCVAX96 (Gabe et al., 1989), SHELXL97 and PREP8 (Ferguson, 1998).

Selected geometric parameters (Å, º) top

N1A—C1A	1.345 (2)	N1B—C1B	1.346 (2)
N1A—C4A	1.346 (2)	N1B—C4B	1.343 (2)
N2A—C1A	1.343 (2)	N2B—C1B	1.343 (2)
N2A—C2A	1.340 (2)	N2B—C2B	1.340 (2)
N4A—C1A	1.357 (2)	N4B—C1B	1.347 (2)
C2A—C3A	1.385 (2)	C2B—C3B	1.381 (3)
C2A—C11A	1.488 (2)	C2B—C11B	1.488 (3)
C3A—C4A	1.384 (2)	C3B—C4B	1.387 (3)
C4A—C21A	1.481 (2)	C4B—C21B	1.484 (3)

N1A—C1A—N2A	126.76 (17)	N1B—C1B—N2B	126.72 (17)
N1A—C1A—N4A	117.05 (17)	N1B—C1B—N4B	116.73 (18)
N2A—C1A—N4A	116.15 (17)	N2B—C1B—N4B	116.55 (18)

N1A—C4A—C21A—C26A	−29.8 (3)	N1B—C4B—C21B—C26B	−36.5 (3)
C3A—C4A—C21A—C26A	151.83 (19)	C3B—C4B—C21B—C26B	142.9 (2)
C3A—C2A—C11A—C12A	149.4 (2)	C3B—C2B—C11B—C12B	−152.6 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N4A—H1A···N1B	0.89 (2)	2.17 (2)	3.058 (2)	172.7 (18)
N4B—H2B···N1A	0.91 (2)	2.20 (2)	3.106 (3)	175.8 (17)
C12A—H12A···Cg1ⁱ	0.93	2.77	3.538 (2)	141
C26A—H26A···Cg2ⁱⁱ	0.93	2.78	3.393 (2)	124

Symmetry codes: (i) −x, −y+2, −z+1; (ii) −x+1, −y+2, −z+1.

Acknowledgements

JFG thanks Dublin City University for the purchase of a diffractometer and computer system. The authors thank the Department of Chemistry, University of West Indies, St Augustine, Trinidad, West Indies, for the plant material. SPG thanks CSIR, Government of India, for a fellowship to SJ.

References

Allen, F. H. (2002). Acta Cryst. B58, 380–388. Web of Science CrossRef CAS IUCr Journals Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Ferguson, G. (1998). PREP8. University of Guelph, Canada. Google Scholar
Frisch, M. J., Trucks, G. W., Schlegel, H. B., Scuseria, G. E., Robb, M. A., Cheeseman, J. R., Montgomery, J. A., Vrenen, T. et al. (2003). GAUSSIAN03 for Windows. March 2003 release. Gaussian Inc., Pittsburgh, Pennsylvania, USA. Google Scholar
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ISSN: 2053-2296

Volume 60| Part 4| April 2004| Pages o229-o231

doi:10.1107/S0108270104002902

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

N—H⋯N hydrogen bonding in 4,6-di­phenyl-2-pyrimidinyl­amine isolated from the plant Justicia secunda (Acanthaceae)

Comment

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N—H⋯N hydrogen bonding in 4,6-diphenyl-2-pyrimidinylamine isolated from the plant Justicia secunda (Acanthaceae)