2-Anilino-5,7-dimethyl­pyrazolo­[1,5-a]pyrimidine-3-carbonitrile

Mohamed, S.K.; Akkurt, M.; Fronczek, F.R.; El-Remaily, M.A.A.; Abdelhamid, A.A.

doi:10.1107/S1600536812035878

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Pages o2782-o2783

doi:10.1107/S1600536812035878

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2-Anilino-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile

Shaaban K. Mohamed,^a Mehmet Akkurt,^b ^* Frank R. Fronczek,^c Mahmoud A. A. El-Remaily ^d and Antar A. Abdelhamid ^a

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, ^cDepartment of Chemistry, Louisiana State University, Baton Rouge, LA 70803-1804, USA, and ^dDepartment of Chemistry, Faculty of Science, Sohag University, 82524 Sohag, Egypt
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 14 August 2012; accepted 15 August 2012; online 25 August 2012)

The title compound, C₁₅H₁₃N₅, crystallizes with two independent molecules in the asymmetric unit. The molecular conformations are stabilized by C—H⋯N contacts forming S(6) ring motifs. In the crystal, pairs of molecules are connected into R₂²(12) dimers by N—H⋯N hydrogen bonds. C—H⋯π interactions and π–π stacking interactions [centroid–centroid distances = 3.6085 (8), 3.6657 (8), 3.4745 (8) and 3.5059 (8) Å] also also observed.

Related literature

For background details and bioactivity of pyrazolopyrimidine compounds, see: Singh et al. (2011 ); Rajendran et al. (2011 ); Earl et al.(1975 ); Bendich et al. (1954 ); Elion et al. (1963 ); Hildick & Shaw (1971 ); Kabayasahi (1973 ); Satherland et al. (1968 ); Soliman et al. (2010 ). For bond-length data, see: Allen et al. (1987 ). For hydrogen-bond motifs, see: Bernstein et al. (1995 ).

Experimental

Crystal data

C₁₅H₁₃N₅
M_r = 263.30
Monoclinic, P 2₁ /c
a = 11.2139 (4) Å
b = 10.4347 (4) Å
c = 22.1753 (9) Å
β = 94.569 (1)°
V = 2586.57 (17) Å³
Z = 8
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 90 K
0.30 × 0.14 × 0.13 mm

Data collection

Bruker Kappa APEXII DUO diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2004 ) T_min = 0.975, T_max = 0.989
16931 measured reflections
6402 independent reflections
4813 reflections with I > 2σ(I)
R_int = 0.027
Standard reflections: 0

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.116
S = 1.02
6402 reflections
365 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg3 are the centroids of the N2/N3/C7–C9 and N3/N5/C9/C11–C13 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N9ⁱ	0.86	2.20	3.0487 (17)	168
N6—H6⋯N4ⁱⁱ	0.86	2.23	3.0703 (17)	167
C1—H1⋯N2	0.93	2.40	2.9158 (17)	115
C16—H16⋯N7	0.93	2.28	2.9059 (17)	124
C4—H4⋯Cg1ⁱⁱⁱ	0.93	2.83	3.5730 (16)	138
C27—H27⋯Cg3ⁱⁱⁱ	0.93	2.99	3.7462 (15)	139
C29—H29B⋯Cg3	0.96	2.95	3.7420 (16)	141
Symmetry codes: (i) x-1, y, z; (ii) x+1, y, z; (iii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); 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/S1600536812035878/bt6821sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812035878/bt6821Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812035878/bt6821Isup3.cml

checkCIF report

Comment top

The pyrazole containing compounds have practical applications in the medicinal and agrochemical fields. Pyrazolopyrimidines in particular represent a class of nitrogen bridgehead antibiotic compounds such as formycin and and allopurinol (Elion et al., 1963) which are still the drug of choice for the treatment of hyperurecemia and gouty arthritis (Earl et al., 1975). In addition, pyrazolopyrimidines have exhibited antimicrobial (Singh et al., 2011; Rajendran et al. 2011, Hildick & Shaw, 1971), antitumor and antileukemic activities (Earl et al., 1975). They are as purine analogues (Bendich et al., 1954; Kabayasahi, 1973) and as such they have useful properties as antimetabolites in purine biochemical reaction (Satherland et al., 1968). In view of the importance of pyrazolpyrimidine derivatives we have planned a systematic study of such compounds, and describe here the crystal structure of the title compound (I) as one of potential bioactive derivative.

As shown in Fig. 1, the two independent molecules (A with N1 and B with N6) in the asymmetric unit of (I) have a similar conformation. In both molecules (A and B), the pyrazolo[1,5-a]pyrimidine rings are essentially planar [maximum deviaitions are 0.015 (1) Å for N2 and N3 in molecule A, and 0.018 (1) Å for N7 in molecule B]. The dihedral angles between the pyrazolo[1,5-a]pyrimidine and phenyl rings are 29.74 (6)° in molecule A and 3.34 (6)° in molecule B. In the both molecules (A and B) of (I), the bond lengths and bond angles are found to have normal values (Allen et al., 1987).

Molecular conformations of the molecules A and B are stabilized by C—H···N contacts generating S(6) ring motifs (Table 1). In the crystal, R₂²(12) dimers by N—H···N hydrogen bonds connect pairs of molecules to each other (Bernstein et al.,1995; Table 1, Fig. 2). Furthermore, C—H···π interactions and π-π stacking interactions [Cg1···Cg6 (x, y, z) = 3.6085 (8) Å, Cg2···Cg5 (x, y, z) = 3.6657 (8) Å, Cg5···Cg7 (2 - x, -y, 1 - z) = 3.4745 (8) Å and Cg6···Cg7 (2 - x, -y, 1 - z) = 3.5059 (8) Å; where Cg1, Cg2, Cg5, Cg6 and Cg7 are the N2/N3/C7–C9, N3/N5/C9/C11–C13, N7/N8/C22–C24, N8/N10/C24/C26–C28 and C16–C21 rings, respectively] are also observed in the crystal structure.

Related literature top

For background details and bioactivity of pyrazolopyrimidine compounds, see: Singh et al. (2011); Rajendran et al. (2011); Earl et al.(1975); Bendich et al. (1954); Elion et al. (1963); Hildick & Shaw (1971); Kabayasahi (1973); Satherland et al. (1968); Soliman et al. (2010). For bond-length data, see: Allen et al. (1987). For hydrogen-bond motifs, see: Bernstein et al. (1995).

Experimental top

The title compound was prepared according to the reported literature (Soliman et al., 2010). Suitable crystals for X-ray diffraction were obtained from ethanol solution of (I) by slow evaporation method (M.p.: 553 K).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SIR97 (Altomare et al., 1999); 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

View of two independent molecules of C₁₅H₁₃N₅ in the asymmetric unit. Displacement ellipsoids for non-H atoms are drawn at the 50% probability level.

View of the dimers formed by pairs of N—H···N hydrogen bonds, forming a R₂²(12) motif. H atoms not involved in hydrogen bonds have been omitted for clarity.

2-Anilino-5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carbonitrile top

Crystal data top

C₁₅H₁₃N₅	F(000) = 1104
M_r = 263.30	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5253 reflections
a = 11.2139 (4) Å	θ = 2.5–28.3°
b = 10.4347 (4) Å	µ = 0.09 mm⁻¹
c = 22.1753 (9) Å	T = 90 K
β = 94.569 (1)°	Needle, yellow
V = 2586.57 (17) Å³	0.30 × 0.14 × 0.13 mm
Z = 8

Data collection top

Bruker Kappa APEXII DUO diffractometer	6402 independent reflections
Radiation source: sealed tube	4813 reflections with I > 2σ(I)
TRIUMPH curved graphite monochromator	R_int = 0.027
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −14→14
T_min = 0.975, T_max = 0.989	k = −9→13
16931 measured reflections	l = −29→29

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0561P)² + 0.7958P] where P = (F_o² + 2F_c²)/3
6402 reflections	(Δ/σ)_max = 0.001
365 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₁₅H₁₃N₅	V = 2586.57 (17) Å³
M_r = 263.30	Z = 8
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.2139 (4) Å	µ = 0.09 mm⁻¹
b = 10.4347 (4) Å	T = 90 K
c = 22.1753 (9) Å	0.30 × 0.14 × 0.13 mm
β = 94.569 (1)°

Data collection top

Bruker Kappa APEXII DUO diffractometer	6402 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	4813 reflections with I > 2σ(I)
T_min = 0.975, T_max = 0.989	R_int = 0.027
16931 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.116	H-atom parameters constrained
S = 1.02	Δρ_max = 0.30 e Å⁻³
6402 reflections	Δρ_min = −0.21 e Å⁻³
365 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.47831 (10)	0.32101 (12)	0.70318 (5)	0.0199 (3)
N2	0.66448 (10)	0.40025 (11)	0.67523 (5)	0.0180 (3)
N3	0.70882 (10)	0.41926 (11)	0.61962 (5)	0.0166 (3)
N4	0.33625 (11)	0.25331 (13)	0.54197 (6)	0.0266 (4)
N5	0.65371 (10)	0.40210 (11)	0.51345 (5)	0.0192 (3)
C1	0.58840 (12)	0.39461 (14)	0.79791 (6)	0.0206 (4)
C2	0.60952 (12)	0.38176 (15)	0.86009 (6)	0.0231 (4)
C3	0.55016 (13)	0.28965 (15)	0.89136 (7)	0.0255 (4)
C4	0.46676 (13)	0.21140 (14)	0.85998 (7)	0.0251 (4)
C5	0.44404 (12)	0.22347 (14)	0.79814 (6)	0.0211 (4)
C6	0.50542 (11)	0.31412 (13)	0.76635 (6)	0.0178 (4)
C7	0.55347 (11)	0.35638 (13)	0.66085 (6)	0.0174 (4)
C8	0.52493 (11)	0.34861 (13)	0.59719 (6)	0.0178 (4)
C9	0.62799 (11)	0.39049 (13)	0.57116 (6)	0.0173 (4)
C10	0.42096 (12)	0.29756 (13)	0.56611 (6)	0.0193 (4)
C11	0.76337 (12)	0.44325 (13)	0.50442 (6)	0.0198 (4)
C12	0.84888 (12)	0.47222 (13)	0.55295 (6)	0.0205 (4)
C13	0.82237 (12)	0.45941 (13)	0.61182 (6)	0.0186 (4)
C14	0.79399 (13)	0.45550 (15)	0.44007 (7)	0.0246 (4)
C15	0.90416 (12)	0.48200 (14)	0.66696 (6)	0.0226 (4)
N6	1.07117 (10)	0.19315 (11)	0.50864 (5)	0.0198 (3)
N7	0.87866 (10)	0.13453 (11)	0.53749 (5)	0.0184 (3)
N8	0.83415 (10)	0.11918 (11)	0.59317 (5)	0.0171 (3)
N9	1.22465 (11)	0.22274 (14)	0.67265 (6)	0.0304 (4)
N10	0.89182 (10)	0.13317 (11)	0.69927 (5)	0.0186 (3)
C16	0.94456 (12)	0.15164 (13)	0.41364 (6)	0.0210 (4)
C17	0.93656 (13)	0.14738 (14)	0.35064 (7)	0.0229 (4)
C18	1.03505 (13)	0.17251 (14)	0.31852 (7)	0.0227 (4)
C19	1.14369 (13)	0.20196 (13)	0.35019 (6)	0.0216 (4)
C20	1.15306 (12)	0.20798 (13)	0.41256 (6)	0.0193 (4)
C21	1.05356 (12)	0.18282 (12)	0.44522 (6)	0.0181 (4)
C22	0.99284 (12)	0.16850 (12)	0.55138 (6)	0.0173 (4)
C23	1.02218 (12)	0.17663 (13)	0.61492 (6)	0.0180 (4)
C24	0.91709 (11)	0.14323 (13)	0.64140 (6)	0.0173 (4)
C25	1.13379 (12)	0.20222 (14)	0.64679 (6)	0.0206 (4)
C26	0.78134 (12)	0.09541 (13)	0.70864 (6)	0.0194 (4)
C27	0.69422 (12)	0.06867 (13)	0.66062 (6)	0.0193 (4)
C28	0.72062 (12)	0.08007 (13)	0.60174 (6)	0.0188 (4)
C29	0.75352 (13)	0.07701 (15)	0.77310 (7)	0.0240 (4)
C30	0.63923 (12)	0.05188 (14)	0.54696 (7)	0.0224 (4)
H1	0.62910	0.45630	0.77730	0.0250*
H1A	0.40660	0.30070	0.69000	0.0240*
H2	0.66430	0.43570	0.88110	0.0280*
H3	0.56610	0.28050	0.93290	0.0310*
H4	0.42580	0.15020	0.88080	0.0300*
H5	0.38750	0.17090	0.77760	0.0250*
H12	0.92450	0.50050	0.54470	0.0250*
H14A	0.84830	0.38830	0.43100	0.0370*
H14B	0.83090	0.53720	0.43440	0.0370*
H14C	0.72230	0.44880	0.41350	0.0370*
H15A	0.86990	0.54510	0.69190	0.0340*
H15B	0.98000	0.51210	0.65540	0.0340*
H15C	0.91540	0.40340	0.68920	0.0340*
H6	1.14110	0.21850	0.52240	0.0240*
H16	0.87780	0.13390	0.43450	0.0250*
H17	0.86380	0.12730	0.32970	0.0280*
H18	1.02860	0.16970	0.27650	0.0270*
H19	1.21060	0.21770	0.32910	0.0260*
H20	1.22600	0.22890	0.43310	0.0230*
H27	0.61800	0.04300	0.66920	0.0230*
H29A	0.76610	−0.01110	0.78440	0.0360*
H29B	0.67160	0.09970	0.77730	0.0360*
H29C	0.80500	0.13060	0.79890	0.0360*
H30A	0.56110	0.03090	0.55890	0.0340*
H30B	0.67020	−0.01920	0.52560	0.0340*
H30C	0.63390	0.12580	0.52110	0.0340*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0128 (5)	0.0291 (7)	0.0172 (6)	−0.0027 (5)	−0.0017 (4)	−0.0004 (5)
N2	0.0161 (5)	0.0196 (6)	0.0183 (6)	−0.0002 (4)	0.0009 (4)	0.0004 (4)
N3	0.0149 (5)	0.0172 (6)	0.0174 (6)	0.0003 (4)	−0.0004 (4)	−0.0020 (4)
N4	0.0188 (6)	0.0376 (8)	0.0231 (6)	−0.0026 (5)	0.0001 (5)	−0.0049 (5)
N5	0.0175 (5)	0.0210 (6)	0.0192 (6)	0.0012 (5)	0.0025 (4)	−0.0021 (4)
C1	0.0170 (6)	0.0245 (7)	0.0201 (7)	−0.0016 (5)	0.0010 (5)	0.0012 (5)
C2	0.0181 (6)	0.0303 (8)	0.0205 (7)	−0.0003 (6)	−0.0015 (5)	−0.0026 (6)
C3	0.0265 (7)	0.0327 (8)	0.0169 (7)	0.0040 (6)	−0.0006 (5)	0.0022 (6)
C4	0.0283 (7)	0.0240 (7)	0.0238 (7)	−0.0004 (6)	0.0068 (6)	0.0036 (6)
C5	0.0188 (6)	0.0215 (7)	0.0233 (7)	−0.0020 (5)	0.0032 (5)	−0.0033 (5)
C6	0.0137 (6)	0.0216 (7)	0.0180 (6)	0.0042 (5)	0.0003 (5)	−0.0007 (5)
C7	0.0152 (6)	0.0170 (6)	0.0196 (7)	0.0012 (5)	−0.0011 (5)	−0.0018 (5)
C8	0.0146 (6)	0.0200 (7)	0.0185 (7)	0.0009 (5)	−0.0003 (5)	−0.0016 (5)
C9	0.0144 (6)	0.0167 (6)	0.0203 (7)	0.0022 (5)	−0.0015 (5)	−0.0028 (5)
C10	0.0166 (6)	0.0237 (7)	0.0177 (7)	0.0017 (5)	0.0021 (5)	−0.0019 (5)
C11	0.0197 (7)	0.0176 (7)	0.0222 (7)	0.0027 (5)	0.0029 (5)	−0.0019 (5)
C12	0.0155 (6)	0.0195 (7)	0.0269 (7)	−0.0014 (5)	0.0034 (5)	−0.0017 (5)
C13	0.0139 (6)	0.0151 (6)	0.0266 (7)	0.0006 (5)	−0.0002 (5)	−0.0019 (5)
C14	0.0233 (7)	0.0269 (8)	0.0242 (7)	0.0004 (6)	0.0064 (6)	−0.0020 (6)
C15	0.0166 (6)	0.0251 (7)	0.0253 (7)	−0.0032 (6)	−0.0037 (5)	−0.0011 (6)
N6	0.0148 (5)	0.0241 (6)	0.0198 (6)	−0.0035 (5)	−0.0022 (4)	−0.0022 (5)
N7	0.0165 (5)	0.0181 (6)	0.0204 (6)	−0.0010 (4)	0.0001 (4)	−0.0005 (4)
N8	0.0147 (5)	0.0171 (6)	0.0191 (6)	−0.0004 (4)	−0.0015 (4)	−0.0010 (4)
N9	0.0208 (6)	0.0462 (8)	0.0237 (7)	−0.0064 (6)	−0.0005 (5)	−0.0009 (6)
N10	0.0158 (5)	0.0194 (6)	0.0205 (6)	0.0005 (4)	0.0002 (4)	−0.0027 (4)
C16	0.0181 (6)	0.0197 (7)	0.0247 (7)	−0.0008 (5)	−0.0008 (5)	0.0000 (5)
C17	0.0214 (7)	0.0221 (7)	0.0240 (7)	−0.0012 (6)	−0.0063 (5)	0.0000 (6)
C18	0.0263 (7)	0.0217 (7)	0.0194 (7)	0.0010 (6)	−0.0020 (5)	0.0013 (5)
C19	0.0207 (7)	0.0201 (7)	0.0240 (7)	0.0014 (5)	0.0016 (5)	0.0026 (5)
C20	0.0162 (6)	0.0182 (7)	0.0228 (7)	0.0008 (5)	−0.0023 (5)	0.0002 (5)
C21	0.0190 (6)	0.0141 (6)	0.0209 (7)	0.0026 (5)	−0.0011 (5)	−0.0001 (5)
C22	0.0162 (6)	0.0143 (6)	0.0209 (7)	0.0009 (5)	−0.0008 (5)	−0.0008 (5)
C23	0.0150 (6)	0.0181 (6)	0.0205 (7)	0.0002 (5)	−0.0011 (5)	−0.0017 (5)
C24	0.0151 (6)	0.0145 (6)	0.0217 (7)	0.0011 (5)	−0.0021 (5)	−0.0024 (5)
C25	0.0175 (6)	0.0248 (7)	0.0195 (7)	−0.0022 (5)	0.0022 (5)	−0.0004 (5)
C26	0.0177 (6)	0.0161 (6)	0.0244 (7)	0.0026 (5)	0.0012 (5)	−0.0015 (5)
C27	0.0134 (6)	0.0177 (7)	0.0267 (7)	0.0004 (5)	0.0011 (5)	−0.0005 (5)
C28	0.0144 (6)	0.0145 (6)	0.0270 (7)	0.0014 (5)	−0.0020 (5)	−0.0010 (5)
C29	0.0194 (7)	0.0290 (8)	0.0237 (7)	0.0008 (6)	0.0026 (5)	−0.0013 (6)
C30	0.0163 (6)	0.0235 (7)	0.0266 (7)	−0.0020 (6)	−0.0036 (5)	−0.0007 (6)

Geometric parameters (Å, º) top

N1—C6	1.4114 (17)	C3—H3	0.9300
N1—C7	1.3615 (17)	C4—H4	0.9300
N2—N3	1.3802 (16)	C5—H5	0.9300
N2—C7	1.3408 (17)	C12—H12	0.9300
N3—C9	1.3825 (17)	C14—H14C	0.9600
N3—C13	1.3645 (18)	C14—H14B	0.9600
N4—C10	1.1494 (19)	C14—H14A	0.9600
N5—C9	1.3396 (17)	C15—H15A	0.9600
N5—C11	1.3326 (18)	C15—H15B	0.9600
N1—H1A	0.8600	C15—H15C	0.9600
N6—C21	1.4086 (17)	C16—C21	1.3978 (19)
N6—C22	1.3670 (17)	C16—C17	1.394 (2)
N7—C22	1.3406 (18)	C17—C18	1.386 (2)
N7—N8	1.3775 (16)	C18—C19	1.391 (2)
N8—C28	1.3646 (18)	C19—C20	1.3801 (19)
N8—C24	1.3833 (17)	C20—C21	1.4026 (19)
N9—C25	1.1488 (19)	C22—C23	1.4237 (19)
N10—C26	1.3320 (18)	C23—C25	1.4129 (19)
N10—C24	1.3402 (17)	C23—C24	1.4019 (18)
N6—H6	0.8600	C26—C27	1.4144 (19)
C1—C2	1.3868 (19)	C26—C29	1.500 (2)
C1—C6	1.3991 (19)	C27—C28	1.3668 (19)
C2—C3	1.386 (2)	C28—C30	1.490 (2)
C3—C4	1.386 (2)	C16—H16	0.9300
C4—C5	1.380 (2)	C17—H17	0.9300
C5—C6	1.3938 (19)	C18—H18	0.9300
C7—C8	1.4247 (19)	C19—H19	0.9300
C8—C10	1.4107 (19)	C20—H20	0.9300
C8—C9	1.4022 (18)	C27—H27	0.9300
C11—C14	1.500 (2)	C29—H29A	0.9600
C11—C12	1.4158 (19)	C29—H29B	0.9600
C12—C13	1.3683 (19)	C29—H29C	0.9600
C13—C15	1.4877 (19)	C30—H30A	0.9600
C1—H1	0.9300	C30—H30B	0.9600
C2—H2	0.9300	C30—H30C	0.9600

C6—N1—C7	127.00 (11)	H14B—C14—H14C	109.00
N3—N2—C7	103.32 (10)	C11—C14—H14A	110.00
N2—N3—C9	113.75 (11)	C13—C15—H15A	109.00
N2—N3—C13	124.31 (11)	H15B—C15—H15C	109.00
C9—N3—C13	121.92 (11)	H15A—C15—H15B	109.00
C9—N5—C11	116.37 (11)	H15A—C15—H15C	109.00
C6—N1—H1A	117.00	C13—C15—H15B	109.00
C7—N1—H1A	116.00	C13—C15—H15C	110.00
C21—N6—C22	129.13 (11)	C17—C16—C21	119.58 (13)
N8—N7—C22	103.44 (10)	C16—C17—C18	121.26 (14)
N7—N8—C28	124.63 (11)	C17—C18—C19	118.94 (14)
C24—N8—C28	121.59 (11)	C18—C19—C20	120.64 (13)
N7—N8—C24	113.74 (11)	C19—C20—C21	120.58 (13)
C24—N10—C26	116.28 (11)	N6—C21—C20	116.56 (12)
C22—N6—H6	115.00	N6—C21—C16	124.43 (12)
C21—N6—H6	115.00	C16—C21—C20	119.00 (12)
C2—C1—C6	119.57 (13)	N6—C22—C23	124.36 (12)
C1—C2—C3	120.91 (13)	N6—C22—N7	123.04 (12)
C2—C3—C4	119.27 (14)	N7—C22—C23	112.60 (12)
C3—C4—C5	120.57 (14)	C24—C23—C25	125.32 (12)
C4—C5—C6	120.32 (13)	C22—C23—C25	129.20 (12)
C1—C6—C5	119.34 (12)	C22—C23—C24	105.31 (12)
N1—C6—C1	123.23 (12)	N8—C24—N10	123.07 (11)
N1—C6—C5	117.42 (12)	N8—C24—C23	104.90 (11)
N1—C7—C8	124.41 (12)	N10—C24—C23	132.03 (12)
N2—C7—C8	112.71 (11)	N9—C25—C23	179.83 (16)
N1—C7—N2	122.86 (12)	C27—C26—C29	120.58 (12)
C9—C8—C10	126.36 (12)	N10—C26—C27	122.42 (12)
C7—C8—C9	105.23 (11)	N10—C26—C29	116.96 (12)
C7—C8—C10	128.12 (12)	C26—C27—C28	120.85 (12)
N3—C9—N5	123.04 (11)	C27—C28—C30	126.63 (12)
N5—C9—C8	131.97 (12)	N8—C28—C27	115.76 (12)
N3—C9—C8	104.98 (11)	N8—C28—C30	117.60 (12)
N4—C10—C8	178.10 (15)	C17—C16—H16	120.00
N5—C11—C12	122.13 (12)	C21—C16—H16	120.00
N5—C11—C14	117.03 (12)	C16—C17—H17	119.00
C12—C11—C14	120.83 (12)	C18—C17—H17	119.00
C11—C12—C13	121.26 (12)	C17—C18—H18	121.00
C12—C13—C15	127.02 (12)	C19—C18—H18	121.00
N3—C13—C15	117.70 (12)	C18—C19—H19	120.00
N3—C13—C12	115.26 (12)	C20—C19—H19	120.00
C6—C1—H1	120.00	C19—C20—H20	120.00
C2—C1—H1	120.00	C21—C20—H20	120.00
C3—C2—H2	120.00	C26—C27—H27	120.00
C1—C2—H2	120.00	C28—C27—H27	120.00
C4—C3—H3	120.00	C26—C29—H29A	110.00
C2—C3—H3	120.00	C26—C29—H29B	110.00
C5—C4—H4	120.00	C26—C29—H29C	109.00
C3—C4—H4	120.00	H29A—C29—H29B	109.00
C4—C5—H5	120.00	H29A—C29—H29C	109.00
C6—C5—H5	120.00	H29B—C29—H29C	109.00
C13—C12—H12	119.00	C28—C30—H30A	109.00
C11—C12—H12	119.00	C28—C30—H30B	109.00
H14A—C14—H14B	109.00	C28—C30—H30C	109.00
H14A—C14—H14C	109.00	H30A—C30—H30B	109.00
C11—C14—H14B	110.00	H30A—C30—H30C	109.00
C11—C14—H14C	109.00	H30B—C30—H30C	109.00

C7—N1—C6—C1	31.2 (2)	C2—C1—C6—N1	179.79 (13)
C7—N1—C6—C5	−149.89 (14)	C2—C1—C6—C5	0.9 (2)
C6—N1—C7—N2	−5.5 (2)	C6—C1—C2—C3	0.5 (2)
C6—N1—C7—C8	173.05 (13)	C1—C2—C3—C4	−1.4 (2)
C7—N2—N3—C13	−177.38 (12)	C2—C3—C4—C5	0.9 (2)
N3—N2—C7—C8	−0.88 (15)	C3—C4—C5—C6	0.4 (2)
C7—N2—N3—C9	1.00 (15)	C4—C5—C6—N1	179.70 (13)
N3—N2—C7—N1	177.84 (12)	C4—C5—C6—C1	−1.4 (2)
N2—N3—C9—N5	−179.79 (12)	N2—C7—C8—C9	0.48 (16)
N2—N3—C13—C12	179.92 (13)	N1—C7—C8—C10	−4.3 (2)
C9—N3—C13—C12	1.67 (19)	N2—C7—C8—C10	174.45 (13)
C13—N3—C9—N5	−1.4 (2)	N1—C7—C8—C9	−178.22 (13)
C9—N3—C13—C15	−177.18 (12)	C7—C8—C9—N3	0.15 (15)
N2—N3—C9—C8	−0.73 (15)	C10—C8—C9—N3	−173.96 (13)
N2—N3—C13—C15	1.07 (19)	C10—C8—C9—N5	5.0 (2)
C13—N3—C9—C8	177.69 (12)	C7—C8—C9—N5	179.09 (14)
C9—N5—C11—C14	179.40 (12)	C14—C11—C12—C13	−178.97 (13)
C9—N5—C11—C12	0.55 (19)	N5—C11—C12—C13	−0.2 (2)
C11—N5—C9—N3	0.18 (19)	C11—C12—C13—N3	−0.9 (2)
C11—N5—C9—C8	−178.60 (14)	C11—C12—C13—C15	177.78 (13)
C21—N6—C22—C23	176.95 (13)	C21—C16—C17—C18	0.5 (2)
C22—N6—C21—C16	4.5 (2)	C17—C16—C21—C20	−0.6 (2)
C21—N6—C22—N7	−3.5 (2)	C17—C16—C21—N6	178.31 (13)
C22—N6—C21—C20	−176.57 (13)	C16—C17—C18—C19	0.3 (2)
N8—N7—C22—N6	179.77 (12)	C17—C18—C19—C20	−1.0 (2)
C22—N7—N8—C24	0.31 (14)	C18—C19—C20—C21	0.9 (2)
N8—N7—C22—C23	−0.64 (14)	C19—C20—C21—C16	−0.1 (2)
C22—N7—N8—C28	−177.66 (12)	C19—C20—C21—N6	−179.07 (12)
N7—N8—C28—C30	0.07 (19)	N6—C22—C23—C25	−4.3 (2)
N7—N8—C24—C23	0.13 (15)	N7—C22—C23—C25	176.09 (14)
C28—N8—C24—N10	−1.7 (2)	N6—C22—C23—C24	−179.68 (12)
N7—N8—C24—N10	−179.72 (12)	N7—C22—C23—C24	0.74 (15)
C24—N8—C28—C27	1.12 (19)	C22—C23—C24—N8	−0.49 (14)
C28—N8—C24—C23	178.17 (12)	C22—C23—C24—N10	179.33 (14)
C24—N8—C28—C30	−177.75 (12)	C25—C23—C24—N8	−176.07 (13)
N7—N8—C28—C27	178.94 (12)	C25—C23—C24—N10	3.8 (2)
C26—N10—C24—N8	1.42 (19)	C29—C26—C27—C28	−177.22 (13)
C26—N10—C24—C23	−178.38 (14)	N10—C26—C27—C28	0.4 (2)
C24—N10—C26—C29	176.88 (12)	C26—C27—C28—N8	−0.5 (2)
C24—N10—C26—C27	−0.77 (19)	C26—C27—C28—C30	178.25 (13)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg3 are the centroids of the N2/N3/C7–C9 and N3/N5/C9/C11–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N9ⁱ	0.86	2.20	3.0487 (17)	168
N6—H6···N4ⁱⁱ	0.86	2.23	3.0703 (17)	167
C1—H1···N2	0.93	2.40	2.9158 (17)	115
C16—H16···N7	0.93	2.28	2.9059 (17)	124
C4—H4···Cg1ⁱⁱⁱ	0.93	2.83	3.5730 (16)	138
C27—H27···Cg3ⁱⁱⁱ	0.93	2.99	3.7462 (15)	139
C29—H29B···Cg3	0.96	2.95	3.7420 (16)	141

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

Experimental details

Crystal data
Chemical formula	C₁₅H₁₃N₅
M_r	263.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	90
a, b, c (Å)	11.2139 (4), 10.4347 (4), 22.1753 (9)
β (°)	94.569 (1)
V (Å³)	2586.57 (17)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.30 × 0.14 × 0.13

Data collection
Diffractometer	Bruker Kappa APEXII DUO diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2004)
T_min, T_max	0.975, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	16931, 6402, 4813
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.116, 1.02
No. of reflections	6402
No. of parameters	365
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SIR97 (Altomare et al., 1999), 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

Cg1 and Cg3 are the centroids of the N2/N3/C7–C9 and N3/N5/C9/C11–C13 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N9ⁱ	0.86	2.20	3.0487 (17)	168
N6—H6···N4ⁱⁱ	0.86	2.23	3.0703 (17)	167
C1—H1···N2	0.93	2.40	2.9158 (17)	115
C16—H16···N7	0.93	2.28	2.9059 (17)	124
C4—H4···Cg1ⁱⁱⁱ	0.93	2.83	3.5730 (16)	138
C27—H27···Cg3ⁱⁱⁱ	0.93	2.99	3.7462 (15)	139
C29—H29B···Cg3	0.96	2.95	3.7420 (16)	141

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

Acknowledgements

We thank Sohag University for the financial support of this project. Manchester Metropolitan University, Erciyes University and Louisiana State University are also gratefuly acknowledged for supporting this study.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Altomare, A., Burla, M. C., Camalli, M., Cascarano, G. L., Giacovazzo, C., Guagliardi, A., Moliterni, A. G. G., Polidori, G. & Spagna, R. (1999). J. Appl. Cryst. 32, 115–119. Web of Science CrossRef CAS IUCr Journals Google Scholar
Bendich, A., Russell, P. J. Jr & Fox, J. J. (1954). J. Am. Chem. Soc. 76, 6073–6077. CrossRef CAS Web of Science Google Scholar
Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Earl, R. A., Pugmire, R. J., Revanker, G. R. & Townsend, L. B. (1975). J. Org. Chem. 40, 1822–1828. CrossRef CAS Web of Science Google Scholar
Elion, G. B., Callahan, S., Nathan, H., Bieher, S., Rundles, R. W. & Hitchings, G. H. (1963). Biochem. Pharmacol. 12, 85–93. CrossRef CAS Web of Science Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Hildick, B. G. & Shaw, G. (1971). J. Chem. Soc. pp. 1610–1613. Google Scholar
Kabayasahi, S. J. (1973). Pharm. Bull. 21, 941–949. Google Scholar
Rajendran, A., Raghupathy, D. & Priyadarshini, M. (2011). Int. J. Chem. Technol. 3, 293–297. CAS Google Scholar
Satherland, E. W., Robinson, G. A. & Butcher, R. W. (1968). Circulation, 37, 279–287. Google Scholar
Sheldrick, G. M. (2004). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, S., Sharma, P. K., Dudhe, R. & Kumar, N. (2011). Int. J. Pharm. Sci. 2, 131–144. CAS Google Scholar
Soliman, A. M., Sultan, A. A., Abdel-Aleem, M. & Abdel-Ghany, H. (2010). J. Int. Environ. Appl. Sci. 5, 883–889. Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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Volume 68| Part 9| September 2012| Pages o2782-o2783

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