N-(2-Methyl­phen­yl)-6-(1H-pyrazol-1-yl)pyridazin-3-amine

Ather, A.Q.; Tahir, M.N.; Khan, M.A.; Athar, M.M.

doi:10.1107/S1600536809022867

organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page o1628

doi:10.1107/S1600536809022867

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N-(2-Methylphenyl)-6-(1H-pyrazol-1-yl)pyridazin-3-amine

Abdul Qayyum Ather,^a M. Nawaz Tahir,^b ^* Misbahul Ain Khan ^c and Muhammad Makshoof Athar ^d

^aDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, and, Applied Chemistry Research Center, PCSIR Laboratories complex, Lahore 54600, Pakistan, ^bDepartment of Physics, University of Sargodha, Sargodha, Pakistan, ^cDepartment of Chemistry, Islamia University, Bahawalpur, Pakistan, and ^dInstitute of Chemistry, University of the Punjab, Lahore, Pakistan
^*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 4 June 2009; accepted 14 June 2009; online 20 June 2009)

The title compound, C₁₄H₁₃N₅, crystallizes with two crystallographically independent molecules in the unit cell. The two molecules form dimers through intermolecular N—H⋯N and C—H⋯N hydrogen bonds. The hydrogen-bonding motifs are R₂²(8) for both the N—H⋯N and C—H⋯N interactions. The pyrazole and pyrimidine rings form dihedral angles of 6.2 (3) and 8.3 (3)° with each other and the dihedral angles between the pyrazole and benzene rings are 54.9 (2) and 58.6 (2)°. The benzene rings of neighbouring dimers also exhibit C—H⋯π interactions.

Related literature

A docking study of pyrazololylpyridazine has shown inhibitory action against glycogen synthase kinase 3, see: Xiao et al. (2006 ); For graph-set notation, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₄H₁₃N₅
M_r = 251.29
Monoclinic, C c
a = 16.548 (5) Å
b = 19.639 (4) Å
c = 8.015 (5) Å
β = 99.619 (5)°
V = 2568.1 (19) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 296 K
0.24 × 0.20 × 0.18 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.982, T_max = 0.988
13833 measured reflections
3209 independent reflections
1716 reflections with I > 2σ(I)
R_int = 0.042

Refinement

R[F² > 2σ(F²)] = 0.063
wR(F²) = 0.167
S = 1.02
3209 reflections
303 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.32 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N7ⁱ	0.86	2.26	3.086 (5)	162
N6—H6A⋯N2ⁱⁱ	0.86	2.26	3.065 (6)	156
C7—H7C⋯N8ⁱ	0.96	2.53	3.482 (8)	175
C21—H21C⋯N3ⁱⁱ	0.96	2.59	3.519 (10)	163
C6—H6⋯Cg1	0.93	2.80	3.529 (6)	136
Symmetry codes: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ . Cg1 is the centroid of benzene ring (C15–C20).

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); 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, 1997 ) and PLATON (Spek, 2009 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809022867/zl2217sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809022867/zl2217Isup2.hkl

checkCIF report

Comment top

Pyrazolylpyridazine derivatives are potential anticholestromic and antihypertensive agents. A docking study of pyrazololylpyridazine has shown inhibitory action against glycogen synthase kinase 3 (Xiao et al., 2006). In continuation of our work on the synthesis and reactions of azolylpyridazines, we have isolated crystals of the title compound, (Fig. 1).

The title compound contains pyrazole, pyridazine and benzene rings. In the asymmetric unit there are two molecules which differ from one another crystallographically.

In one molecule (containing C1—C14), the pyrazole ring is oriented at dihedral angles of 6.16 (30)° and 54.91 (21)° with the pyridazine and benzene rings, respectively. In the second molecule, the pyrazole ring exhibits dihedral angles of 8.26 (34)° and 58.57 (20)° with the pyridazine and benzene rings, respectively. Through intermolecular N–H···N and C–H···N hydrogen bonds the two molecules form dimers with hydrogen bonding ring motifs of R₂²(8) (Bernstein et al., 1995). C—H···π interactions between the benzene rings are also observed in the structure of the title compound (Table 1, Cg1 is the centroid of benzene ring (C15—C20)).

Related literature top

A docking study of pyrazololylpyridazine has shown

inhibitory action against glycogen synthase kinase 3, see: Xiao et al. (2006); For graph-set notation, see: Bernstein et al. (1995). Cg1 is the centroid of benzene ring (C15–C20).

Experimental top

3-Chloro-6-(1H-pyrazol-1-yl)pyridazine (1.68 g, 9.33 mmol) and 2-toluidine (1 g, 9.34 mmol) were refluxed in dimethylformamide (DMF) for 2 h. The reaction mixture was concentrated under vacuum and poured in cold water. The precipitates obtained were filtered, washed with distilled water and dried to give 51.28% yield. The product obtained was purified by column chromatography and recrystallized in benzene.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); 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, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown as small spheres of arbitrary radii.
	Fig. 2. Packing diagram of the title compound (PLATON: Spek, 2009) showing the dimers and ring motifs. Hydrogen bonds are symbolized by dashed lines.

N-(2-Methylphenyl)-6-(1H-pyrazol-1-yl)pyridazin-3-amine top

Crystal data top

C₁₄H₁₃N₅	F(000) = 1056
M_r = 251.29	D_x = 1.300 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 2920 reflections
a = 16.548 (5) Å	θ = 2.1–28.4°
b = 19.639 (4) Å	µ = 0.08 mm⁻¹
c = 8.015 (5) Å	T = 296 K
β = 99.619 (5)°	Prismatic, white
V = 2568.1 (19) Å³	0.24 × 0.20 × 0.18 mm
Z = 8

Data collection top

Bruker Kappa APEXII CCD diffractometer	3209 independent reflections
Radiation source: fine-focus sealed tube	1716 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.042
Detector resolution: 7.40 pixels mm^-1	θ_max = 28.4°, θ_min = 2.1°
ω scans	h = −22→22
Absorption correction: multi-scan (SADABS; Bruker, 2005)	k = −24→26
T_min = 0.982, T_max = 0.988	l = −8→10
13833 measured reflections

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)] = 0.063	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.056P)² + 2.2381P] where P = (F_o² + 2F_c²)/3
3209 reflections	(Δ/σ)_max < 0.001
303 parameters	Δρ_max = 0.40 e Å⁻³
2 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₁₄H₁₃N₅	V = 2568.1 (19) Å³
M_r = 251.29	Z = 8
Monoclinic, Cc	Mo Kα radiation
a = 16.548 (5) Å	µ = 0.08 mm⁻¹
b = 19.639 (4) Å	T = 296 K
c = 8.015 (5) Å	0.24 × 0.20 × 0.18 mm
β = 99.619 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	3209 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	1716 reflections with I > 2σ(I)
T_min = 0.982, T_max = 0.988	R_int = 0.042
13833 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.063	2 restraints
wR(F²) = 0.167	H-atom parameters constrained
S = 1.02	Δρ_max = 0.40 e Å⁻³
3209 reflections	Δρ_min = −0.32 e Å⁻³
303 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > σ(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
N1	0.3430 (2)	0.3434 (2)	0.7950 (6)	0.0617 (12)
H1	0.3887	0.3649	0.8034	0.074*
N2	0.4170 (2)	0.2448 (2)	0.8037 (6)	0.0629 (12)
N3	0.4249 (2)	0.1762 (2)	0.8272 (6)	0.0640 (12)
N4	0.3754 (3)	0.0702 (2)	0.8745 (6)	0.0615 (12)
N5	0.3154 (3)	0.0302 (3)	0.9209 (8)	0.0904 (18)
N6	0.0751 (3)	0.1921 (2)	0.2213 (6)	0.0609 (12)
H6A	0.0288	0.2129	0.2121	0.073*
N7	0.0075 (2)	0.0924 (2)	0.2451 (5)	0.0562 (11)
N8	0.0015 (2)	0.0239 (2)	0.2363 (6)	0.0544 (10)
N9	0.0521 (2)	−0.08308 (18)	0.1990 (5)	0.0522 (10)
N10	0.1036 (3)	−0.1245 (2)	0.1338 (6)	0.0680 (13)
C1	0.2696 (3)	0.3825 (2)	0.7595 (6)	0.0499 (11)
C2	0.2655 (3)	0.4452 (2)	0.8362 (6)	0.0567 (13)
C3	0.1903 (4)	0.4801 (3)	0.7933 (8)	0.0714 (16)
H3	0.1850	0.5229	0.8401	0.086*
C4	0.1249 (4)	0.4537 (3)	0.6860 (9)	0.0779 (17)
H4	0.0762	0.4781	0.6631	0.093*
C5	0.1306 (3)	0.3920 (3)	0.6125 (8)	0.0714 (15)
H5	0.0863	0.3739	0.5390	0.086*
C6	0.2032 (3)	0.3570 (3)	0.6494 (7)	0.0556 (12)
H6	0.2078	0.3149	0.5988	0.067*
C7	0.3362 (4)	0.4739 (3)	0.9540 (8)	0.0779 (18)
H7A	0.3461	0.4469	1.0552	0.117*
H7B	0.3241	0.5199	0.9823	0.117*
H7C	0.3840	0.4735	0.9008	0.117*
C8	0.3467 (3)	0.2744 (2)	0.8169 (6)	0.0521 (12)
C9	0.2804 (3)	0.2371 (3)	0.8593 (7)	0.0613 (14)
H9	0.2325	0.2590	0.8752	0.074*
C10	0.2878 (3)	0.1693 (3)	0.8763 (7)	0.0599 (14)
H10	0.2443	0.1425	0.8979	0.072*
C11	0.3625 (3)	0.1409 (3)	0.8603 (7)	0.0556 (12)
C12	0.4397 (4)	0.0335 (3)	0.8451 (9)	0.0790 (17)
H12	0.4871	0.0504	0.8118	0.095*
C13	0.4230 (5)	−0.0330 (3)	0.8729 (11)	0.098 (2)
H13	0.4560	−0.0707	0.8636	0.117*
C14	0.3461 (5)	−0.0318 (4)	0.9180 (11)	0.105 (3)
H14	0.3187	−0.0707	0.9437	0.126*
C15	0.1471 (2)	0.23170 (19)	0.2472 (5)	0.0810 (8)
C16	0.1493 (2)	0.2952 (2)	0.1713 (5)	0.0810 (8)
C17	0.2214 (2)	0.33286 (16)	0.1961 (5)	0.0810 (8)
H17	0.2229	0.3753	0.1453	0.097*
C18	0.2913 (2)	0.30707 (19)	0.2966 (6)	0.0810 (8)
H18	0.3395	0.3323	0.3131	0.097*
C19	0.2891 (2)	0.2436 (2)	0.3724 (5)	0.0810 (8)
H19	0.3358	0.2263	0.4397	0.097*
C20	0.2170 (2)	0.20591 (16)	0.3477 (5)	0.0810 (8)
H20	0.2155	0.1634	0.3984	0.097*
C21	0.0748 (5)	0.3242 (3)	0.0633 (10)	0.104 (3)
H21A	0.0527	0.2915	−0.0212	0.156*
H21B	0.0894	0.3649	0.0093	0.156*
H21C	0.0344	0.3347	0.1326	0.156*
C22	0.0745 (3)	0.1232 (2)	0.2100 (6)	0.0515 (12)
C23	0.1379 (3)	0.0856 (3)	0.1572 (7)	0.0599 (13)
H23	0.1829	0.1076	0.1264	0.072*
C24	0.1322 (3)	0.0166 (3)	0.1517 (6)	0.0551 (13)
H24	0.1734	−0.0102	0.1202	0.066*
C25	0.0619 (3)	−0.0118 (2)	0.1954 (6)	0.0466 (11)
C26	−0.0083 (4)	−0.1183 (3)	0.2518 (9)	0.084 (2)
H26	−0.0511	−0.1002	0.2995	0.101*
C27	0.0043 (4)	−0.1848 (3)	0.2232 (10)	0.085 (2)
H27	−0.0270	−0.2218	0.2470	0.102*
C28	0.0737 (4)	−0.1854 (3)	0.1509 (9)	0.0819 (19)
H28	0.0973	−0.2250	0.1173	0.098*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.045 (2)	0.044 (2)	0.096 (3)	−0.0036 (19)	0.011 (2)	−0.006 (2)
N2	0.045 (2)	0.044 (2)	0.100 (4)	−0.0009 (18)	0.010 (2)	−0.001 (2)
N3	0.046 (2)	0.048 (3)	0.098 (3)	−0.001 (2)	0.011 (2)	0.003 (2)
N4	0.050 (2)	0.050 (3)	0.082 (3)	−0.005 (2)	0.002 (2)	0.005 (2)
N5	0.067 (3)	0.064 (4)	0.136 (5)	−0.015 (3)	0.005 (3)	0.024 (3)
N6	0.054 (2)	0.038 (2)	0.091 (3)	0.001 (2)	0.013 (2)	−0.002 (2)
N7	0.047 (2)	0.043 (3)	0.079 (3)	0.0015 (19)	0.015 (2)	−0.006 (2)
N8	0.042 (2)	0.041 (2)	0.081 (3)	−0.0020 (18)	0.014 (2)	−0.005 (2)
N9	0.050 (2)	0.040 (2)	0.067 (3)	0.0012 (19)	0.010 (2)	−0.003 (2)
N10	0.068 (3)	0.044 (3)	0.097 (4)	0.006 (2)	0.027 (3)	−0.007 (2)
C1	0.052 (3)	0.039 (3)	0.062 (3)	0.000 (2)	0.020 (2)	0.002 (2)
C2	0.074 (3)	0.042 (3)	0.063 (3)	−0.005 (3)	0.037 (3)	0.001 (2)
C3	0.099 (5)	0.046 (3)	0.079 (4)	0.013 (3)	0.043 (4)	0.000 (3)
C4	0.069 (4)	0.078 (4)	0.090 (5)	0.023 (3)	0.024 (3)	0.017 (4)
C5	0.060 (3)	0.069 (4)	0.087 (4)	0.003 (3)	0.018 (3)	0.005 (3)
C6	0.056 (3)	0.044 (3)	0.069 (3)	0.004 (2)	0.018 (2)	−0.001 (2)
C7	0.096 (4)	0.064 (4)	0.080 (4)	−0.021 (3)	0.032 (3)	−0.016 (3)
C8	0.048 (3)	0.047 (3)	0.059 (3)	−0.006 (2)	0.004 (2)	0.001 (2)
C9	0.057 (3)	0.056 (3)	0.076 (4)	0.009 (3)	0.027 (3)	0.008 (3)
C10	0.052 (3)	0.062 (3)	0.068 (4)	−0.008 (3)	0.016 (3)	0.010 (3)
C11	0.052 (3)	0.047 (3)	0.068 (3)	−0.005 (2)	0.010 (2)	0.006 (2)
C12	0.069 (4)	0.059 (4)	0.108 (5)	0.004 (3)	0.011 (3)	−0.008 (3)
C13	0.094 (5)	0.060 (4)	0.126 (6)	0.008 (4)	−0.018 (4)	0.007 (4)
C14	0.083 (5)	0.053 (4)	0.166 (8)	−0.017 (4)	−0.019 (5)	0.033 (4)
C15	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C16	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C17	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C18	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C19	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C20	0.0806 (16)	0.0625 (15)	0.112 (2)	−0.0139 (12)	0.0506 (16)	−0.0222 (14)
C21	0.154 (7)	0.066 (4)	0.103 (6)	0.021 (5)	0.053 (5)	0.023 (4)
C22	0.048 (3)	0.047 (3)	0.061 (3)	−0.006 (2)	0.013 (2)	0.001 (2)
C23	0.055 (3)	0.054 (3)	0.077 (4)	−0.005 (3)	0.028 (3)	0.002 (3)
C24	0.047 (3)	0.052 (3)	0.071 (3)	0.003 (2)	0.022 (2)	−0.008 (3)
C25	0.042 (2)	0.046 (3)	0.051 (3)	0.003 (2)	0.007 (2)	−0.005 (2)
C26	0.070 (4)	0.052 (4)	0.139 (6)	0.005 (3)	0.044 (4)	0.011 (3)
C27	0.079 (4)	0.043 (3)	0.136 (6)	−0.003 (3)	0.025 (4)	0.001 (3)
C28	0.077 (4)	0.046 (4)	0.123 (6)	0.008 (3)	0.017 (4)	−0.011 (3)

Geometric parameters (Å, º) top

N1—C8	1.366 (6)	C8—C9	1.406 (7)
N1—C1	1.426 (6)	C9—C10	1.342 (7)
N1—H1	0.8600	C9—H9	0.9300
N2—C8	1.321 (6)	C10—C11	1.383 (7)
N2—N3	1.364 (6)	C10—H10	0.9300
N3—C11	1.306 (6)	C12—C13	1.362 (8)
N4—C12	1.338 (7)	C12—H12	0.9300
N4—N5	1.366 (6)	C13—C14	1.380 (11)
N4—C11	1.406 (6)	C13—H13	0.9300
N5—C14	1.321 (9)	C14—H14	0.9300
N6—C22	1.356 (6)	C15—C16	1.3900
N6—C15	1.407 (5)	C15—C20	1.3900
N6—H6A	0.8600	C16—C17	1.3900
N7—C22	1.335 (6)	C16—C21	1.495 (8)
N7—N8	1.349 (5)	C17—C18	1.3900
N8—C25	1.306 (6)	C17—H17	0.9300
N9—C26	1.341 (7)	C18—C19	1.3900
N9—N10	1.345 (6)	C18—H18	0.9300
N9—C25	1.411 (5)	C19—C20	1.3900
N10—C28	1.310 (7)	C19—H19	0.9300
C1—C6	1.383 (7)	C20—H20	0.9300
C1—C2	1.383 (6)	C21—H21A	0.9600
C2—C3	1.412 (8)	C21—H21B	0.9600
C2—C7	1.485 (8)	C21—H21C	0.9600
C3—C4	1.367 (9)	C22—C23	1.404 (7)
C3—H3	0.9300	C23—C24	1.358 (7)
C4—C5	1.356 (8)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.387 (7)
C5—C6	1.372 (7)	C24—H24	0.9300
C5—H5	0.9300	C26—C27	1.347 (8)
C6—H6	0.9300	C26—H26	0.9300
C7—H7A	0.9600	C27—C28	1.371 (9)
C7—H7B	0.9600	C27—H27	0.9300
C7—H7C	0.9600	C28—H28	0.9300

C8—N1—C1	125.3 (4)	N4—C12—C13	107.4 (6)
C8—N1—H1	117.3	N4—C12—H12	126.3
C1—N1—H1	117.3	C13—C12—H12	126.3
C8—N2—N3	119.3 (4)	C12—C13—C14	104.4 (6)
C11—N3—N2	119.5 (4)	C12—C13—H13	127.8
C12—N4—N5	112.0 (5)	C14—C13—H13	127.8
C12—N4—C11	129.1 (5)	N5—C14—C13	113.3 (6)
N5—N4—C11	118.9 (5)	N5—C14—H14	123.4
C14—N5—N4	103.1 (6)	C13—C14—H14	123.4
C22—N6—C15	123.9 (4)	C16—C15—C20	120.0
C22—N6—H6A	118.1	C16—C15—N6	120.9 (3)
C15—N6—H6A	118.1	C20—C15—N6	119.0 (3)
C22—N7—N8	119.8 (4)	C17—C16—C15	120.0
C25—N8—N7	119.7 (4)	C17—C16—C21	119.0 (4)
C26—N9—N10	111.4 (4)	C15—C16—C21	121.0 (4)
C26—N9—C25	127.8 (4)	C16—C17—C18	120.0
N10—N9—C25	120.7 (4)	C16—C17—H17	120.0
C28—N10—N9	103.7 (5)	C18—C17—H17	120.0
C6—C1—C2	120.9 (5)	C17—C18—C19	120.0
C6—C1—N1	119.5 (4)	C17—C18—H18	120.0
C2—C1—N1	119.6 (4)	C19—C18—H18	120.0
C1—C2—C3	115.5 (5)	C20—C19—C18	120.0
C1—C2—C7	121.9 (5)	C20—C19—H19	120.0
C3—C2—C7	122.6 (5)	C18—C19—H19	120.0
C4—C3—C2	122.8 (5)	C19—C20—C15	120.0
C4—C3—H3	118.6	C19—C20—H20	120.0
C2—C3—H3	118.6	C15—C20—H20	120.0
C5—C4—C3	120.5 (6)	C16—C21—H21A	109.5
C5—C4—H4	119.7	C16—C21—H21B	109.5
C3—C4—H4	119.7	H21A—C21—H21B	109.5
C4—C5—C6	118.3 (6)	C16—C21—H21C	109.5
C4—C5—H5	120.8	H21A—C21—H21C	109.5
C6—C5—H5	120.8	H21B—C21—H21C	109.5
C5—C6—C1	122.0 (5)	N7—C22—N6	115.8 (4)
C5—C6—H6	119.0	N7—C22—C23	120.9 (4)
C1—C6—H6	119.0	N6—C22—C23	123.2 (5)
C2—C7—H7A	109.5	C24—C23—C22	118.9 (5)
C2—C7—H7B	109.5	C24—C23—H23	120.5
H7A—C7—H7B	109.5	C22—C23—H23	120.5
C2—C7—H7C	109.5	C23—C24—C25	116.7 (5)
H7A—C7—H7C	109.5	C23—C24—H24	121.7
H7B—C7—H7C	109.5	C25—C24—H24	121.7
N2—C8—N1	116.6 (4)	N8—C25—C24	123.8 (4)
N2—C8—C9	121.5 (5)	N8—C25—N9	115.6 (4)
N1—C8—C9	121.8 (5)	C24—C25—N9	120.6 (4)
C10—C9—C8	118.7 (5)	N9—C26—C27	107.6 (6)
C10—C9—H9	120.7	N9—C26—H26	126.2
C8—C9—H9	120.7	C27—C26—H26	126.2
C9—C10—C11	117.3 (5)	C26—C27—C28	104.1 (6)
C9—C10—H10	121.4	C26—C27—H27	127.9
C11—C10—H10	121.4	C28—C27—H27	127.9
N3—C11—C10	123.6 (5)	N10—C28—C27	113.2 (6)
N3—C11—N4	115.2 (5)	N10—C28—H28	123.4
C10—C11—N4	121.1 (5)	C27—C28—H28	123.4

C8—N2—N3—C11	0.8 (8)	N4—C12—C13—C14	0.4 (8)
C12—N4—N5—C14	−0.1 (7)	N4—N5—C14—C13	0.4 (8)
C11—N4—N5—C14	178.6 (5)	C12—C13—C14—N5	−0.5 (9)
C22—N7—N8—C25	0.8 (7)	C22—N6—C15—C16	144.5 (4)
C26—N9—N10—C28	−1.0 (7)	C22—N6—C15—C20	−34.3 (6)
C25—N9—N10—C28	−176.7 (5)	C20—C15—C16—C17	0.0
C8—N1—C1—C6	−39.5 (7)	N6—C15—C16—C17	−178.8 (4)
C8—N1—C1—C2	140.1 (5)	C20—C15—C16—C21	−179.7 (5)
C6—C1—C2—C3	−0.3 (7)	N6—C15—C16—C21	1.5 (5)
N1—C1—C2—C3	−179.9 (4)	C15—C16—C17—C18	0.0
C6—C1—C2—C7	−179.6 (5)	C21—C16—C17—C18	179.7 (5)
N1—C1—C2—C7	0.8 (7)	C16—C17—C18—C19	0.0
C1—C2—C3—C4	1.2 (8)	C17—C18—C19—C20	0.0
C7—C2—C3—C4	−179.5 (6)	C18—C19—C20—C15	0.0
C2—C3—C4—C5	−1.2 (9)	C16—C15—C20—C19	0.0
C3—C4—C5—C6	0.3 (9)	N6—C15—C20—C19	178.8 (4)
C4—C5—C6—C1	0.6 (8)	N8—N7—C22—N6	179.7 (4)
C2—C1—C6—C5	−0.6 (8)	N8—N7—C22—C23	2.7 (7)
N1—C1—C6—C5	179.0 (5)	C15—N6—C22—N7	157.2 (4)
N3—N2—C8—N1	178.9 (4)	C15—N6—C22—C23	−25.8 (8)
N3—N2—C8—C9	1.8 (8)	N7—C22—C23—C24	−3.9 (8)
C1—N1—C8—N2	162.4 (5)	N6—C22—C23—C24	179.3 (5)
C1—N1—C8—C9	−20.5 (8)	C22—C23—C24—C25	1.6 (8)
N2—C8—C9—C10	−4.1 (8)	N7—N8—C25—C24	−3.1 (8)
N1—C8—C9—C10	179.0 (5)	N7—N8—C25—N9	176.5 (4)
C8—C9—C10—C11	3.6 (8)	C23—C24—C25—N8	1.8 (8)
N2—N3—C11—C10	−1.2 (8)	C23—C24—C25—N9	−177.7 (5)
N2—N3—C11—N4	177.1 (5)	C26—N9—C25—N8	−5.7 (8)
C9—C10—C11—N3	−1.2 (8)	N10—N9—C25—N8	169.3 (5)
C9—C10—C11—N4	−179.3 (5)	C26—N9—C25—C24	173.9 (6)
C12—N4—C11—N3	−6.2 (9)	N10—N9—C25—C24	−11.1 (7)
N5—N4—C11—N3	175.3 (5)	N10—N9—C26—C27	1.0 (8)
C12—N4—C11—C10	172.1 (6)	C25—N9—C26—C27	176.3 (5)
N5—N4—C11—C10	−6.3 (8)	N9—C26—C27—C28	−0.5 (8)
N5—N4—C12—C13	−0.2 (8)	N9—N10—C28—C27	0.6 (7)
C11—N4—C12—C13	−178.7 (6)	C26—C27—C28—N10	−0.1 (8)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7ⁱ	0.86	2.26	3.086 (5)	162
N6—H6A···N2ⁱⁱ	0.86	2.26	3.065 (6)	156
C7—H7C···N8ⁱ	0.96	2.53	3.482 (8)	175
C21—H21C···N3ⁱⁱ	0.96	2.59	3.519 (10)	163
C6—H6···Cg1	0.93	2.80	3.529 (6)	136

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

Experimental details

Crystal data
Chemical formula	C₁₄H₁₃N₅
M_r	251.29
Crystal system, space group	Monoclinic, Cc
Temperature (K)	296
a, b, c (Å)	16.548 (5), 19.639 (4), 8.015 (5)
β (°)	99.619 (5)
V (Å³)	2568.1 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.24 × 0.20 × 0.18

Data collection
Diffractometer	Bruker Kappa APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.982, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	13833, 3209, 1716
R_int	0.042
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.063, 0.167, 1.02
No. of reflections	3209
No. of parameters	303
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.32

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N7ⁱ	0.86	2.26	3.086 (5)	162
N6—H6A···N2ⁱⁱ	0.86	2.26	3.065 (6)	156
C7—H7C···N8ⁱ	0.96	2.53	3.482 (8)	175
C21—H21C···N3ⁱⁱ	0.96	2.59	3.519 (10)	163
C6—H6···Cg1	0.93	2.80	3.529 (6)	136

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

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer at GCU, Lahore and for technical support, respectively.

References

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