2-Amino-6-(piperidin-1-yl)-4-p-tolyl­pyridine-3,5-dicarbo­nitrile

Inglebert, S.A.; Kamalraja, J.; Sethusankar, K.; Vasuki, G.

doi:10.1107/S1600536813030845

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1807

doi:10.1107/S1600536813030845

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2-Amino-6-(piperidin-1-yl)-4-p-tolylpyridine-3,5-dicarbonitrile

S. Antony Inglebert,^a Jayabal Kamalraja,^b K. Sethusankar ^c ^* and Gnanasambandam Vasuki ^b

^aSri Ram Engineering College, Chennai 602 024, India, ^bDepartment of Chemistry, Pondichery University, Pondichery 605 014, India, and ^cDepartment of Physics, RKM Vivekananda College (Autonomous), Chennai 600 004, India
^*Correspondence e-mail: ksethusankar@yahoo.co.in

(Received 9 October 2013; accepted 10 November 2013; online 23 November 2013)

In the title compound, C₁₉H₁₉N₅, the piperidine ring adopts a chair conformation. The pyridine ring is essentially planar, with a maximum deviation of 0.039 (2) Å for a C atom substituted with a carbonitrile group. The mean plane of the central pyridine ring makes the dihedral angles of 37.90 (14) and 56.10 (12)° with the piperidine and benzene rings, respectively. In the crystal, molecules are linked via N—H⋯N and C—H⋯N hydrogen bonds, forming chains along [101], and enclosing R₂²(17) ring motifs. The chains are linked by further C—H⋯N hydrogen bonds, forming two-dimensional networks lying parallel to (10-1), and enclosing inversion dimers with R₂²(20) ring motifs.

CCDC reference: 971236

Related literature

For background to pyridine derivatives and their biological activity, see: Chaubey & Pandeya (2011 ). For puckering parameters, see: Cremer & Pople (1975 ). For graph-set notation, see: Bernstein et al. (1995 ). For a related structure, see: Inglebert et al. (2011 ).

Experimental

Crystal data

C₁₉H₁₉N₅
M_r = 317.39
Monoclinic, P 2₁ /n
a = 14.8695 (12) Å
b = 7.7350 (6) Å
c = 15.2791 (13) Å
β = 107.196 (8)°
V = 1678.8 (2) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.37 × 0.30 × 0.25 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2008 ) T_min = 0.972, T_max = 0.981
7726 measured reflections
3705 independent reflections
1346 reflections with I > 2σ(I)
R_int = 0.056

Refinement

R[F² > 2σ(F²)] = 0.060
wR(F²) = 0.148
S = 0.77
3705 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.18 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N5—H5C⋯N3ⁱ	0.86	2.18	2.999 (4)	160
C2—H2B⋯N4ⁱⁱ	0.97	2.62	3.509 (4)	153
C19—H19A⋯N4ⁱⁱⁱ	0.96	2.61	3.509 (4)	156
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z; (iii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 971236

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813030845/rk2416sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030845/rk2416Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030845/rk2416Isup3.cml

checkCIF report

Comment top

Pyridine ring system is widely distributed in nature, especially in plant kingdom. Many important alkaloids atropine from Deadly nightshade (Atropa belladonna) contains saturated pyridine nucleus. The pyridine is found to have a large number of biological activities those including antiviral, anticancer, antimicrobial, antidiabetic and antitubercular. Pyridine is also a very active neutraceutical found in the form of vitamin B3 (Chaubey & Pandeya, 2011).

The cyano groups are flipped to different sides of the pyridine plane with atoms C12 & N3 showing deviations of 0.3416 (1)Å and 0.6489 (1)Å, while atoms C11 & N4 are bent out of the pyridine plane by -0.0866 (1)Å and -0.1408 (1)Å, respectively. The pyridine ring (N1/C6–C10) forms dihedral angles of 37.90 (14)° and 56.10 (12)° with piperidine (N2/C1–C5) and phenyl ring (C13–C18).

The pyridine ring is essentially planar with a maximum deviation of -0.039 (2) Å for C7 atom. The piperidine ring adopts a chair conformation [puckering parameters (Cremer & Pople, 1975): Q = 0.579 (3)Å, θ = 172.5 (4)° and ϕ = 152 (3)°]. The amino group lies in the pyridine ring. The title compound exhibits the structural similarities with the reported related structure (Inglebert et al., 2011).

In the crystal, molecules are connected through the intermolecular C—H···N and N—H···N hydrogen bonds, generating a R₂²(17) (Bernstein et al., 1995) motif and also chain along a axis. In addition, another pair of intermolecular, C—H···N hydrogen bond link neighbouring molecules, forming an inversion dimer and generate a R₂²(20) ring motif (Table 1).

Related literature top

For background to pyridine derivatives and their biological activity, see: Chaubey & Pandeya (2011). For puckering parameters, see: Cremer & Pople (1975). For graph-set notation, see: Bernstein et al. (1995). For a related structure, see: Inglebert et al. (2011).

Experimental top

Initially a mixture of 4–methylbenzaldehyde (2 mmol, 0.24 g), malononitrile (3 mmol, 0.198 g), piperidine (1.5 mmol, 0.128 g) and was stirred without any solvent at room temperature. A solid appeared immediately which was dissolved in a minimum amount (3 ml) of ethanol and the solution was refluxed until completion of the reaction (monitered by TLC). The reaction mixture was cooled. Ethanol was evaporated under reduced pressure and the residue was extracted with dichloromethane (3×10ml). Evaporation of solvent left the crude solid which was subjected to silica gel column chromatography [25 : 75 / ethyl acetate : hexane] and the product was recrystallized from dichloromethane.

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. A view of the molecular structure, showing the atom numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing structure of the title compound shows two intermolecular C—H···N and N—H···N hydrogen bond to generate R₂²(17) motif. H atoms have been omited for clarity.
	Fig. 3. The packing structure of the title compound shows another pair of intermolecular C—H···N hydrogen bonds to form inversion dimer. H atoms have been omited for clarity.

2-Amino-6-(piperidin-1-yl)-4-p-tolylpyridine-3,5-dicarbonitrile top

Crystal data top

C₁₉H₁₉N₅	F(000) = 672
M_r = 317.39	D_x = 1.256 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -p 2yn	Cell parameters from 3705 reflections
a = 14.8695 (12) Å	θ = 2.8–27.5°
b = 7.7350 (6) Å	µ = 0.08 mm⁻¹
c = 15.2791 (13) Å	T = 295 K
β = 107.196 (8)°	Block, colourless
V = 1678.8 (2) Å³	0.37 × 0.30 × 0.25 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	3705 independent reflections
Radiation source: fine–focus sealed tube	1346 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.056
ω and ϕ scans	θ_max = 27.5°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Bruker, 2008)	h = −19→8
T_min = 0.972, T_max = 0.981	k = −10→9
7726 measured reflections	l = −19→19

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.148	H-atom parameters constrained
S = 0.77	w = 1/[σ²(F_o²) + (0.068P)² + 0.0452P] where P = (F_o² + 2F_c²)/3
3705 reflections	(Δ/σ)_max < 0.001
218 parameters	Δρ_max = 0.18 e Å⁻³
0 restraints	Δρ_min = −0.29 e Å⁻³

Crystal data top

C₁₉H₁₉N₅	V = 1678.8 (2) Å³
M_r = 317.39	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 14.8695 (12) Å	µ = 0.08 mm⁻¹
b = 7.7350 (6) Å	T = 295 K
c = 15.2791 (13) Å	0.37 × 0.30 × 0.25 mm
β = 107.196 (8)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3705 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2008)	1346 reflections with I > 2σ(I)
T_min = 0.972, T_max = 0.981	R_int = 0.056
7726 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.148	H-atom parameters constrained
S = 0.77	Δρ_max = 0.18 e Å⁻³
3705 reflections	Δρ_min = −0.29 e Å⁻³
218 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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 (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.18652 (19)	0.6347 (4)	−0.1252 (2)	0.0608 (9)
H1A	0.2077	0.5189	−0.1334	0.073*
H1B	0.2152	0.6684	−0.0619	0.073*
C2	0.2160 (2)	0.7592 (4)	−0.1883 (3)	0.0738 (10)
H2A	0.2834	0.7499	−0.1776	0.089*
H2B	0.2025	0.8763	−0.1733	0.089*
C3	0.1661 (3)	0.7255 (4)	−0.2895 (3)	0.0804 (11)
H3A	0.1796	0.8190	−0.3261	0.097*
H3B	0.1895	0.6189	−0.3083	0.097*
C4	0.0606 (2)	0.7120 (4)	−0.3062 (2)	0.0694 (9)
H4A	0.0355	0.8241	−0.2971	0.083*
H4B	0.0305	0.6762	−0.3689	0.083*
C5	0.0396 (2)	0.5832 (4)	−0.24158 (19)	0.0541 (8)
H5A	−0.0280	0.5735	−0.2534	0.065*
H5B	0.0636	0.4707	−0.2516	0.065*
C6	0.03918 (17)	0.6941 (3)	−0.08729 (18)	0.0377 (6)
C7	−0.06080 (18)	0.7199 (3)	−0.10909 (17)	0.0393 (7)
C8	−0.09990 (17)	0.7577 (3)	−0.03913 (17)	0.0371 (6)
C9	−0.04006 (17)	0.7845 (3)	0.04943 (17)	0.0390 (6)
C10	0.05840 (18)	0.7707 (3)	0.06310 (18)	0.0423 (7)
C11	−0.07316 (18)	0.8218 (4)	0.1260 (2)	0.0469 (7)
C12	−0.1223 (2)	0.7317 (4)	−0.2007 (2)	0.0501 (7)
C13	−0.20408 (17)	0.7636 (3)	−0.05558 (17)	0.0389 (7)
C14	−0.25728 (18)	0.6183 (3)	−0.09053 (18)	0.0480 (7)
H14	−0.2291	0.5234	−0.1090	0.058*
C15	−0.35192 (19)	0.6144 (4)	−0.09781 (19)	0.0503 (8)
H15	−0.3865	0.5158	−0.1212	0.060*
C16	−0.39660 (18)	0.7517 (4)	−0.07161 (18)	0.0457 (7)
C17	−0.34374 (19)	0.8981 (4)	−0.04005 (19)	0.0530 (8)
H17	−0.3729	0.9948	−0.0245	0.064*
C18	−0.24811 (19)	0.9038 (4)	−0.03101 (19)	0.0510 (8)
H18	−0.2137	1.0029	−0.0082	0.061*
C19	−0.49842 (18)	0.7409 (4)	−0.0753 (2)	0.0621 (9)
H19A	−0.5336	0.6874	−0.1317	0.093*
H19B	−0.5224	0.8552	−0.0719	0.093*
H19C	−0.5044	0.6734	−0.0246	0.093*
N1	0.09533 (14)	0.7257 (3)	−0.00185 (15)	0.0435 (6)
N2	0.08305 (15)	0.6368 (3)	−0.14634 (15)	0.0494 (6)
N3	−0.17316 (17)	0.7510 (3)	−0.27279 (18)	0.0718 (8)
N4	−0.09375 (18)	0.8519 (3)	0.19069 (18)	0.0690 (8)
N5	0.11881 (16)	0.8013 (3)	0.14709 (15)	0.0639 (7)
H5C	0.1785	0.7910	0.1561	0.077*
H5D	0.0976	0.8310	0.1915	0.077*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0354 (18)	0.091 (2)	0.051 (2)	0.0125 (16)	0.0047 (15)	−0.0054 (17)
C2	0.0436 (19)	0.088 (2)	0.091 (3)	−0.0040 (17)	0.0231 (19)	−0.004 (2)
C3	0.081 (3)	0.096 (3)	0.072 (3)	0.000 (2)	0.034 (2)	0.015 (2)
C4	0.073 (2)	0.084 (2)	0.045 (2)	0.0123 (18)	0.0078 (18)	0.0084 (17)
C5	0.0489 (18)	0.0681 (19)	0.0394 (18)	0.0019 (15)	0.0037 (14)	−0.0112 (15)
C6	0.0289 (15)	0.0466 (15)	0.0312 (16)	−0.0013 (12)	−0.0008 (12)	−0.0032 (13)
C7	0.0308 (14)	0.0550 (17)	0.0243 (15)	−0.0002 (13)	−0.0041 (12)	0.0013 (12)
C8	0.0289 (14)	0.0418 (15)	0.0321 (15)	−0.0006 (12)	−0.0043 (12)	0.0029 (12)
C9	0.0305 (14)	0.0521 (16)	0.0287 (16)	0.0030 (13)	0.0001 (12)	0.0008 (13)
C10	0.0328 (15)	0.0516 (16)	0.0308 (16)	0.0012 (13)	−0.0086 (13)	0.0005 (13)
C11	0.0366 (17)	0.0588 (17)	0.0363 (18)	0.0075 (14)	−0.0032 (14)	0.0022 (15)
C12	0.0346 (16)	0.073 (2)	0.0365 (17)	−0.0008 (15)	0.0006 (13)	−0.0015 (15)
C13	0.0291 (14)	0.0505 (16)	0.0302 (15)	0.0044 (13)	−0.0018 (11)	0.0026 (13)
C14	0.0348 (17)	0.0562 (18)	0.0464 (19)	−0.0003 (15)	0.0018 (14)	−0.0069 (14)
C15	0.0346 (17)	0.0627 (19)	0.0467 (19)	−0.0072 (15)	0.0013 (14)	−0.0071 (15)
C16	0.0298 (15)	0.0728 (19)	0.0286 (16)	−0.0015 (16)	−0.0005 (12)	0.0051 (15)
C17	0.0378 (18)	0.069 (2)	0.048 (2)	0.0125 (16)	0.0066 (14)	−0.0023 (15)
C18	0.0380 (17)	0.0588 (18)	0.0479 (19)	−0.0024 (15)	−0.0002 (14)	−0.0071 (15)
C19	0.0348 (16)	0.103 (2)	0.045 (2)	−0.0013 (16)	0.0072 (14)	−0.0007 (17)
N1	0.0292 (12)	0.0603 (14)	0.0322 (14)	0.0019 (11)	−0.0043 (10)	−0.0048 (11)
N2	0.0321 (13)	0.0779 (16)	0.0332 (14)	0.0014 (12)	0.0019 (11)	−0.0058 (12)
N3	0.0418 (15)	0.122 (2)	0.0382 (16)	0.0048 (15)	−0.0092 (12)	0.0035 (15)
N4	0.069 (2)	0.095 (2)	0.0407 (17)	0.0215 (15)	0.0134 (15)	0.0021 (15)
N5	0.0350 (13)	0.1071 (19)	0.0366 (15)	0.0111 (13)	−0.0094 (11)	−0.0156 (14)

Geometric parameters (Å, º) top

C1—N2	1.476 (3)	C9—C10	1.420 (3)
C1—C2	1.516 (4)	C9—C11	1.426 (4)
C1—H1A	0.9700	C10—N1	1.315 (3)
C1—H1B	0.9700	C10—N5	1.352 (3)
C2—C3	1.528 (4)	C11—N4	1.142 (3)
C2—H2A	0.9700	C12—N3	1.147 (3)
C2—H2B	0.9700	C13—C18	1.375 (3)
C3—C4	1.517 (4)	C13—C14	1.388 (3)
C3—H3A	0.9700	C14—C15	1.379 (3)
C3—H3B	0.9700	C14—H14	0.9300
C4—C5	1.498 (4)	C15—C16	1.374 (4)
C4—H4A	0.9700	C15—H15	0.9300
C4—H4B	0.9700	C16—C17	1.381 (4)
C5—N2	1.467 (3)	C16—C19	1.501 (4)
C5—H5A	0.9700	C17—C18	1.388 (4)
C5—H5B	0.9700	C17—H17	0.9300
C6—N2	1.336 (3)	C18—H18	0.9300
C6—N1	1.348 (3)	C19—H19A	0.9600
C6—C7	1.438 (3)	C19—H19B	0.9600
C7—C8	1.390 (3)	C19—H19C	0.9600
C7—C12	1.431 (4)	N5—H5C	0.8600
C8—C9	1.398 (3)	N5—H5D	0.8600
C8—C13	1.495 (3)

N2—C1—C2	109.4 (2)	C8—C9—C10	117.7 (2)
N2—C1—H1A	109.8	C8—C9—C11	123.3 (2)
C2—C1—H1A	109.8	C10—C9—C11	119.0 (2)
N2—C1—H1B	109.8	N1—C10—N5	117.0 (2)
C2—C1—H1B	109.8	N1—C10—C9	123.4 (2)
H1A—C1—H1B	108.2	N5—C10—C9	119.5 (3)
C1—C2—C3	113.0 (3)	N4—C11—C9	175.6 (3)
C1—C2—H2A	109.0	N3—C12—C7	175.8 (3)
C3—C2—H2A	109.0	C18—C13—C14	118.7 (2)
C1—C2—H2B	109.0	C18—C13—C8	122.1 (2)
C3—C2—H2B	109.0	C14—C13—C8	119.0 (2)
H2A—C2—H2B	107.8	C15—C14—C13	120.1 (3)
C4—C3—C2	110.4 (3)	C15—C14—H14	120.0
C4—C3—H3A	109.6	C13—C14—H14	120.0
C2—C3—H3A	109.6	C16—C15—C14	122.0 (3)
C4—C3—H3B	109.6	C16—C15—H15	119.0
C2—C3—H3B	109.6	C14—C15—H15	119.0
H3A—C3—H3B	108.1	C15—C16—C17	117.5 (2)
C5—C4—C3	110.0 (3)	C15—C16—C19	121.0 (3)
C5—C4—H4A	109.7	C17—C16—C19	121.5 (3)
C3—C4—H4A	109.7	C16—C17—C18	121.4 (3)
C5—C4—H4B	109.7	C16—C17—H17	119.3
C3—C4—H4B	109.7	C18—C17—H17	119.3
H4A—C4—H4B	108.2	C13—C18—C17	120.3 (3)
N2—C5—C4	110.5 (2)	C13—C18—H18	119.9
N2—C5—H5A	109.6	C17—C18—H18	119.9
C4—C5—H5A	109.6	C16—C19—H19A	109.5
N2—C5—H5B	109.6	C16—C19—H19B	109.5
C4—C5—H5B	109.6	H19A—C19—H19B	109.5
H5A—C5—H5B	108.1	C16—C19—H19C	109.5
N2—C6—N1	115.3 (2)	H19A—C19—H19C	109.5
N2—C6—C7	124.6 (2)	H19B—C19—H19C	109.5
N1—C6—C7	120.1 (2)	C10—N1—C6	120.1 (2)
C8—C7—C12	116.6 (2)	C6—N2—C5	127.2 (2)
C8—C7—C6	119.3 (2)	C6—N2—C1	122.8 (2)
C12—C7—C6	123.6 (3)	C5—N2—C1	109.8 (2)
C7—C8—C9	119.0 (2)	C10—N5—H5C	120.0
C7—C8—C13	121.7 (2)	C10—N5—H5D	120.0
C9—C8—C13	119.3 (2)	H5C—N5—H5D	120.0

N2—C1—C2—C3	−53.8 (3)	C9—C8—C13—C14	−120.1 (3)
C1—C2—C3—C4	50.1 (4)	C18—C13—C14—C15	−1.7 (4)
C2—C3—C4—C5	−52.2 (4)	C8—C13—C14—C15	173.6 (2)
C3—C4—C5—N2	60.4 (3)	C13—C14—C15—C16	0.2 (4)
N2—C6—C7—C8	171.4 (2)	C14—C15—C16—C17	2.1 (4)
N1—C6—C7—C8	−7.6 (4)	C14—C15—C16—C19	−176.6 (3)
N2—C6—C7—C12	−17.2 (4)	C15—C16—C17—C18	−2.9 (4)
N1—C6—C7—C12	163.8 (2)	C19—C16—C17—C18	175.7 (3)
C12—C7—C8—C9	−166.5 (2)	C14—C13—C18—C17	0.8 (4)
C6—C7—C8—C9	5.6 (4)	C8—C13—C18—C17	−174.3 (3)
C12—C7—C8—C13	15.9 (4)	C16—C17—C18—C13	1.5 (4)
C6—C7—C8—C13	−172.1 (2)	N5—C10—N1—C6	−179.7 (2)
C7—C8—C9—C10	−0.3 (3)	C9—C10—N1—C6	1.7 (4)
C13—C8—C9—C10	177.4 (2)	N2—C6—N1—C10	−175.2 (2)
C7—C8—C9—C11	−179.2 (2)	C7—C6—N1—C10	3.9 (4)
C13—C8—C9—C11	−1.5 (4)	N1—C6—N2—C5	176.4 (2)
C8—C9—C10—N1	−3.6 (4)	C7—C6—N2—C5	−2.6 (4)
C11—C9—C10—N1	175.4 (2)	N1—C6—N2—C1	−9.6 (4)
C8—C9—C10—N5	177.9 (2)	C7—C6—N2—C1	171.4 (2)
C11—C9—C10—N5	−3.1 (4)	C4—C5—N2—C6	109.7 (3)
C7—C8—C13—C18	−127.4 (3)	C4—C5—N2—C1	−64.9 (3)
C9—C8—C13—C18	55.0 (3)	C2—C1—N2—C6	−114.6 (3)
C7—C8—C13—C14	57.5 (3)	C2—C1—N2—C5	60.3 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···N3ⁱ	0.86	2.18	2.999 (4)	160
C2—H2B···N4ⁱⁱ	0.97	2.62	3.509 (4)	153
C19—H19A···N4ⁱⁱⁱ	0.96	2.61	3.509 (4)	156

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x, −y+2, −z; (iii) x−1/2, −y+3/2, z−1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N5—H5C···N3ⁱ	0.86	2.18	2.999 (4)	160
C2—H2B···N4ⁱⁱ	0.97	2.62	3.509 (4)	153
C19—H19A···N4ⁱⁱⁱ	0.96	2.61	3.509 (4)	156

Symmetry codes: (i) x+1/2, −y+3/2, z+1/2; (ii) −x, −y+2, −z; (iii) x−1/2, −y+3/2, z−1/2.

Acknowledgements

The authors gratefully acknowledge Dr Babu Varghese, SAIF, IIT, Chennai, India, for the data collection.

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