6,6-Dibenzyl­tetra­zolo[1,5-a]pyrimidine-5,7(4H,6H)-dione

Baruah, P.K.; Gonnade, R.G.; Sanjayan, G.J.

doi:10.1107/S1600536807034162

6,6-Dibenzyltetrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione

P. K. Baruah, R. G. Gonnade and G. J. Sanjayan

The title compound, C₁₈H₁₅N₅O₂, exhibits a conformation in which the benzyl groups are folded symmetrically towards the tetrazole–pyrimidine–dione group. Molecules related by an inversion centre form dimers via intermolecular N—H

O hydrogen bonds. These dimers are linked to each other through weak C—H

N hydrogen bonds.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807034162/cf2114sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807034162/cf2114Isup2.hkl Contains datablock I

CCDC reference: 657803

checkCIF report

Key indicators

Single-crystal X-ray study
T = 297 K
Mean (C-C) = 0.004 Å
R factor = 0.052
wR factor = 0.122
Data-to-parameter ratio = 10.3

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT230_ALERT_2_C Hirshfeld Test Diff for    N1     -   C2      ..       5.10 su
PLAT230_ALERT_2_C Hirshfeld Test Diff for    C3     -   C4      ..       6.40 su
PLAT245_ALERT_2_C U(iso) H18     Smaller than U(eq) C18     by ...       0.01 AngSq
PLAT480_ALERT_4_C Long H...A H-Bond Reported H15    ..  N2      ..       2.73 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H12B   ..  N3      ..       2.67 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  N4      ..       2.68 Ang.
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  N4      ..       2.71 Ang.

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   2 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   4 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

Heterocycle-based self-assembling systems capable of forming two-, three- and four-centered hydrogen bonds are gaining interest in designing functional solids due to their high dimerization constant (Zimmerman et al., 2002; Meijer et al., 2005; Baruah et al., 2005). The tetrazole-based title compound (I) has been synthesized and we report here its crystal structure.

The title molecule adopts a 'bat-like' conformation (Fig. 1). The central tetrazole-pyrimidine-dione group is approximately planar. Molecules of (I) form centrosymmetric dimers (Fig. 2) via intermolecular N—H···O hydrogen bonds (Table 1) in which tetrazole-pyrimidine-dione groups are coplanar and the benzyl groups are approximately perpendicular to this plane.

The molecular packing viewed down the a axis (Fig. 3) shows the association of the centrosymmetric dimers via C—H···N contacts (Table 1). The C9—H9···N4ⁱⁱⁱ and C15—H15···N2ⁱ interactions link the centrosymmetric dimers along the b axis, whereas along the c axis these dimers are associated via the C5—H5B···N4^iv contact.

Related literature top

For related literature, see: Baruah et al. (2005); Johnstone et al. (1980); Maslak et al. (1999); Meijer et al. (2005); Zimmerman et al. (2002).

Experimental top

Dibenzyl diethylmalonate and dibenzyl malonic acid were synthesized according to the literature procedure (Maslak et al., 1999; Johnstone et al., 1980). To a solution of dibenzyl malonic acid (2.85 g, 10 mmol, 1 equiv.) in dry dichloromethane (10 ml) at 273 K, oxalyl chloride (3.5 ml, 40 mmol, 4 equiv.) was added along with a catalytic amount of N,N-dimethylformamide (DMF). After stirring the reaction mixture at room temperature for 2 h, the solvent was removed under reduced pressure. The resulting diacid chloride was dissolved in dry DMF (5 ml) and added to a solution containing 5-aminotetrazole (1.27 g, 10 mmol, 1 equiv.) and N,N-diisopropylethylamine (5.2 ml, 30 mmol, 3 equiv.) in dry DMF (5 ml) maintained at 253 K. The reaction mixture was stirred for 4 h at room temperature and poured into water. The usual work-up and purification of the crude product by column chromatography afforded a white solid (1.95 g, 81.5%). Colorless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a solution in a dichloromethane-light petroleum ether mixture at room temperature.

Structure description top

For related literature, see: Baruah et al. (2005); Johnstone et al. (1980); Maslak et al. (1999); Meijer et al. (2005); Zimmerman et al. (2002).

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXTL (Bruker, 2003).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. Centrosymmetric dimeric association of molecules of (I), connected by N—H···O hydrogen bonds shown as dashed lines.
	Fig. 3. A packing diagram of (I), viewed down the a axis, showing linking of the centrosymmetric dimers through C—H···N hydrogen bonds depicted by red dashed lines.

6,6-Dibenzyltetrazolo[1,5-a]pyrimidine-5,7(4H,6H)-dione top

Crystal data top

C₁₈H₁₅N₅O₂	F(000) = 1392
M_r = 333.35	D_x = 1.334 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1821 reflections
a = 8.6247 (13) Å	θ = 2.4–21.4°
b = 16.777 (3) Å	µ = 0.09 mm⁻¹
c = 22.950 (4) Å	T = 297 K
V = 3320.8 (9) Å³	Needle, colorless
Z = 8	0.41 × 0.10 × 0.04 mm

Data collection top

CCD area-detector diffractometer	2932 independent reflections
Radiation source: fine-focus sealed tube	1813 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.074
φ and ω scans	θ_max = 25.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −10→10
T_min = 0.963, T_max = 0.997	k = −17→19
15340 measured reflections	l = −20→27

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	All H-atom parameters refined
S = 1.01	w = 1/[σ²(F_o²) + (0.0534P)² + 0.911P] where P = (F_o² + 2F_c²)/3
2932 reflections	(Δ/σ)_max < 0.001
286 parameters	Δρ_max = 0.19 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

C₁₈H₁₅N₅O₂	V = 3320.8 (9) Å³
M_r = 333.35	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 8.6247 (13) Å	µ = 0.09 mm⁻¹
b = 16.777 (3) Å	T = 297 K
c = 22.950 (4) Å	0.41 × 0.10 × 0.04 mm

Data collection top

CCD area-detector diffractometer	2932 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2003)	1813 reflections with I > 2σ(I)
T_min = 0.963, T_max = 0.997	R_int = 0.074
15340 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.122	All H-atom parameters refined
S = 1.01	Δρ_max = 0.19 e Å⁻³
2932 reflections	Δρ_min = −0.24 e Å⁻³
286 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
O1	−0.1488 (2)	0.03404 (11)	0.54832 (7)	0.0354 (5)
O2	0.0857 (2)	0.13057 (11)	0.72322 (8)	0.0453 (5)
N1	0.1102 (2)	0.03592 (14)	0.56024 (9)	0.0286 (5)
N2	0.3838 (3)	0.03595 (14)	0.58267 (10)	0.0399 (6)
N3	0.4617 (3)	0.05786 (14)	0.63174 (10)	0.0423 (6)
N4	0.3698 (3)	0.08262 (14)	0.67263 (10)	0.0420 (6)
N5	0.2222 (2)	0.07682 (13)	0.64897 (9)	0.0334 (6)
C1	−0.0375 (3)	0.04826 (15)	0.57957 (11)	0.0286 (6)
C2	0.2361 (3)	0.04863 (15)	0.59512 (11)	0.0314 (6)
C3	0.0833 (3)	0.09921 (15)	0.67621 (12)	0.0322 (6)
C4	−0.0634 (3)	0.07811 (15)	0.64204 (10)	0.0273 (6)
C5	−0.1472 (3)	0.00954 (16)	0.67624 (12)	0.0309 (7)
C6	−0.0575 (3)	−0.06689 (15)	0.68050 (10)	0.0286 (6)
C7	−0.0797 (3)	−0.12794 (16)	0.64032 (12)	0.0347 (7)
C8	0.0003 (4)	−0.19929 (18)	0.64508 (13)	0.0430 (8)
C9	0.1036 (4)	−0.21058 (19)	0.69051 (14)	0.0447 (8)
C10	0.1284 (4)	−0.15038 (18)	0.73039 (14)	0.0436 (8)
C11	0.0484 (3)	−0.07930 (18)	0.72570 (12)	0.0366 (7)
C12	−0.1717 (3)	0.15218 (17)	0.64069 (12)	0.0318 (7)
C13	−0.1120 (3)	0.22087 (16)	0.60477 (11)	0.0317 (6)
C14	−0.0059 (4)	0.27493 (18)	0.62691 (13)	0.0409 (7)
C15	0.0449 (4)	0.33920 (19)	0.59442 (15)	0.0506 (9)
C16	−0.0121 (4)	0.3509 (2)	0.53849 (14)	0.0501 (8)
C17	−0.1148 (4)	0.29751 (19)	0.51558 (13)	0.0473 (8)
C18	−0.1652 (4)	0.23301 (19)	0.54796 (12)	0.0407 (7)
H1	0.127 (4)	0.0115 (19)	0.5266 (15)	0.072 (11)*
H7	−0.158 (3)	−0.1225 (16)	0.6105 (11)	0.041 (8)*
H8	−0.014 (3)	−0.2450 (18)	0.6191 (13)	0.059 (9)*
H9	0.159 (3)	−0.2605 (16)	0.6925 (11)	0.042 (8)*
H10	0.199 (3)	−0.1603 (15)	0.7625 (11)	0.041 (8)*
H11	0.060 (3)	−0.0377 (15)	0.7524 (12)	0.036 (8)*
H14	0.033 (3)	0.2692 (17)	0.6642 (12)	0.051 (9)*
H15	0.118 (3)	0.3780 (17)	0.6111 (11)	0.043 (8)*
H16	0.021 (3)	0.3982 (17)	0.5183 (13)	0.057 (9)*
H17	−0.160 (3)	0.3020 (17)	0.4752 (13)	0.057 (9)*
H18	−0.232 (3)	0.1955 (14)	0.5325 (10)	0.030 (7)*
H5A	−0.242 (3)	0.0023 (13)	0.6565 (10)	0.027 (7)*
H12A	−0.187 (3)	0.1670 (14)	0.6826 (11)	0.033 (7)*
H5B	−0.163 (3)	0.0319 (13)	0.7160 (11)	0.029 (7)*
H12B	−0.269 (3)	0.1353 (14)	0.6252 (10)	0.024 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0256 (10)	0.0551 (12)	0.0254 (9)	0.0020 (9)	−0.0013 (8)	−0.0077 (9)
O2	0.0500 (13)	0.0565 (13)	0.0296 (11)	−0.0135 (10)	−0.0050 (9)	−0.0048 (10)
N1	0.0203 (12)	0.0438 (14)	0.0216 (11)	0.0002 (10)	−0.0002 (9)	−0.0031 (10)
N2	0.0284 (14)	0.0544 (15)	0.0370 (13)	0.0011 (11)	−0.0047 (11)	0.0029 (12)
N3	0.0257 (14)	0.0562 (16)	0.0451 (15)	−0.0016 (11)	−0.0060 (12)	−0.0055 (13)
N4	0.0317 (15)	0.0536 (15)	0.0406 (14)	−0.0056 (12)	−0.0114 (12)	0.0014 (12)
N5	0.0290 (14)	0.0406 (13)	0.0308 (13)	−0.0029 (11)	−0.0022 (10)	0.0017 (11)
C1	0.0292 (16)	0.0353 (15)	0.0212 (13)	−0.0012 (12)	−0.0001 (12)	0.0004 (12)
C2	0.0377 (18)	0.0318 (15)	0.0248 (14)	−0.0047 (13)	−0.0024 (12)	0.0060 (12)
C3	0.0354 (17)	0.0293 (15)	0.0318 (15)	−0.0039 (12)	0.0054 (13)	0.0055 (13)
C4	0.0247 (15)	0.0365 (15)	0.0207 (12)	−0.0020 (12)	0.0028 (11)	−0.0034 (12)
C5	0.0268 (16)	0.0438 (17)	0.0222 (14)	−0.0059 (13)	0.0031 (13)	−0.0061 (13)
C6	0.0242 (15)	0.0378 (15)	0.0237 (13)	−0.0074 (12)	0.0042 (11)	0.0018 (12)
C7	0.0314 (17)	0.0429 (18)	0.0298 (15)	−0.0081 (14)	−0.0009 (13)	−0.0043 (13)
C8	0.0441 (19)	0.0410 (18)	0.0439 (17)	−0.0056 (15)	0.0018 (15)	−0.0110 (15)
C9	0.0374 (18)	0.0400 (18)	0.057 (2)	0.0008 (16)	0.0023 (15)	0.0029 (17)
C10	0.0365 (19)	0.0483 (19)	0.0462 (18)	−0.0067 (15)	−0.0112 (16)	0.0048 (16)
C11	0.0378 (18)	0.0416 (17)	0.0303 (15)	−0.0081 (14)	−0.0028 (13)	−0.0033 (14)
C12	0.0261 (16)	0.0416 (17)	0.0278 (16)	0.0004 (13)	0.0037 (12)	−0.0023 (13)
C13	0.0300 (15)	0.0359 (15)	0.0293 (14)	0.0065 (13)	0.0033 (12)	−0.0024 (12)
C14	0.0439 (19)	0.0421 (18)	0.0367 (16)	0.0009 (15)	−0.0073 (15)	0.0020 (15)
C15	0.052 (2)	0.0407 (19)	0.059 (2)	−0.0102 (16)	−0.0100 (17)	0.0057 (17)
C16	0.056 (2)	0.0455 (19)	0.049 (2)	0.0007 (17)	0.0091 (17)	0.0103 (17)
C17	0.061 (2)	0.049 (2)	0.0325 (17)	0.0101 (17)	−0.0002 (16)	0.0018 (16)
C18	0.0422 (18)	0.0431 (18)	0.0367 (17)	0.0000 (15)	−0.0055 (14)	−0.0038 (15)

Geometric parameters (Å, º) top

O1—C1	1.222 (3)	C8—C9	1.384 (4)
O2—C3	1.201 (3)	C8—H8	0.98 (3)
N1—C1	1.364 (3)	C9—C10	1.380 (4)
N1—C2	1.366 (3)	C9—H9	0.97 (3)
N1—H1	0.89 (3)	C10—C11	1.382 (4)
N2—C2	1.323 (3)	C10—H10	0.97 (3)
N2—N3	1.361 (3)	C11—H11	0.93 (3)
N3—N4	1.297 (3)	C12—C13	1.507 (4)
N4—N5	1.388 (3)	C12—H12A	1.00 (2)
N5—C2	1.329 (3)	C12—H12B	0.95 (2)
N5—C3	1.402 (3)	C13—C14	1.385 (4)
C1—C4	1.535 (3)	C13—C18	1.397 (4)
C3—C4	1.530 (4)	C14—C15	1.382 (4)
C4—C12	1.555 (4)	C14—H14	0.92 (3)
C4—C5	1.569 (4)	C15—C16	1.388 (4)
C5—C6	1.501 (4)	C15—H15	0.98 (3)
C5—H5A	0.94 (3)	C16—C17	1.366 (4)
C5—H5B	1.00 (2)	C16—H16	0.96 (3)
C6—C7	1.391 (3)	C17—C18	1.383 (4)
C6—C11	1.397 (4)	C17—H17	1.01 (3)
C7—C8	1.386 (4)	C18—H18	0.92 (2)
C7—H7	0.96 (3)

C1—N1—C2	121.9 (2)	C9—C8—C7	119.9 (3)
C1—N1—H1	120 (2)	C9—C8—H8	115.7 (17)
C2—N1—H1	117 (2)	C7—C8—H8	124.4 (18)
C2—N2—N3	104.6 (2)	C10—C9—C8	120.0 (3)
N4—N3—N2	112.6 (2)	C10—C9—H9	121.7 (16)
N3—N4—N5	104.8 (2)	C8—C9—H9	118.3 (16)
C2—N5—N4	107.8 (2)	C9—C10—C11	120.2 (3)
C2—N5—C3	126.0 (2)	C9—C10—H10	118.3 (15)
N4—N5—C3	126.2 (2)	C11—C10—H10	121.4 (15)
O1—C1—N1	120.9 (2)	C10—C11—C6	120.8 (3)
O1—C1—C4	119.8 (2)	C10—C11—H11	122.8 (16)
N1—C1—C4	119.3 (2)	C6—C11—H11	116.4 (16)
N2—C2—N5	110.2 (2)	C13—C12—C4	114.6 (2)
N2—C2—N1	127.9 (2)	C13—C12—H12A	112.2 (14)
N5—C2—N1	121.9 (2)	C4—C12—H12A	104.9 (14)
O2—C3—N5	120.3 (2)	C13—C12—H12B	108.8 (14)
O2—C3—C4	125.1 (2)	C4—C12—H12B	107.3 (14)
N5—C3—C4	114.6 (2)	H12A—C12—H12B	109 (2)
C3—C4—C1	115.7 (2)	C14—C13—C18	117.6 (3)
C3—C4—C12	108.8 (2)	C14—C13—C12	121.7 (2)
C1—C4—C12	109.3 (2)	C18—C13—C12	120.6 (3)
C3—C4—C5	107.1 (2)	C15—C14—C13	121.5 (3)
C1—C4—C5	107.2 (2)	C15—C14—H14	117.8 (18)
C12—C4—C5	108.6 (2)	C13—C14—H14	120.7 (18)
C6—C5—C4	115.0 (2)	C14—C15—C16	119.8 (3)
C6—C5—H5A	111.6 (14)	C14—C15—H15	120.6 (15)
C4—C5—H5A	104.7 (14)	C16—C15—H15	119.5 (15)
C6—C5—H5B	109.4 (14)	C17—C16—C15	119.5 (3)
C4—C5—H5B	104.2 (13)	C17—C16—H16	123.2 (18)
H5A—C5—H5B	112 (2)	C15—C16—H16	117.2 (18)
C7—C6—C11	118.2 (3)	C16—C17—C18	120.7 (3)
C7—C6—C5	121.0 (2)	C16—C17—H17	123.8 (17)
C11—C6—C5	120.8 (2)	C18—C17—H17	115.5 (18)
C8—C7—C6	121.0 (3)	C17—C18—C13	120.8 (3)
C8—C7—H7	119.0 (16)	C17—C18—H18	121.5 (15)
C6—C7—H7	119.8 (16)	C13—C18—H18	117.7 (15)

C2—N2—N3—N4	0.1 (3)	O1—C1—C4—C5	64.4 (3)
N2—N3—N4—N5	−0.1 (3)	N1—C1—C4—C5	−113.8 (3)
N3—N4—N5—C2	0.1 (3)	C3—C4—C5—C6	−63.6 (3)
N3—N4—N5—C3	−177.9 (2)	C1—C4—C5—C6	61.2 (3)
C2—N1—C1—O1	−177.6 (2)	C12—C4—C5—C6	179.1 (2)
C2—N1—C1—C4	0.6 (4)	C4—C5—C6—C7	−94.0 (3)
N3—N2—C2—N5	−0.1 (3)	C4—C5—C6—C11	87.3 (3)
N3—N2—C2—N1	−179.9 (2)	C11—C6—C7—C8	0.3 (4)
N4—N5—C2—N2	0.0 (3)	C5—C6—C7—C8	−178.4 (3)
C3—N5—C2—N2	178.0 (2)	C6—C7—C8—C9	0.3 (4)
N4—N5—C2—N1	179.8 (2)	C7—C8—C9—C10	−1.0 (5)
C3—N5—C2—N1	−2.1 (4)	C8—C9—C10—C11	1.1 (5)
C1—N1—C2—N2	177.0 (3)	C9—C10—C11—C6	−0.5 (4)
C1—N1—C2—N5	−2.8 (4)	C7—C6—C11—C10	−0.2 (4)
C2—N5—C3—O2	−173.4 (2)	C5—C6—C11—C10	178.5 (3)
N4—N5—C3—O2	4.3 (4)	C3—C4—C12—C13	68.6 (3)
C2—N5—C3—C4	8.3 (3)	C1—C4—C12—C13	−58.5 (3)
N4—N5—C3—C4	−174.0 (2)	C5—C4—C12—C13	−175.1 (2)
O2—C3—C4—C1	172.4 (2)	C4—C12—C13—C14	−82.6 (3)
N5—C3—C4—C1	−9.4 (3)	C4—C12—C13—C18	98.8 (3)
O2—C3—C4—C12	49.0 (3)	C18—C13—C14—C15	0.6 (4)
N5—C3—C4—C12	−132.7 (2)	C12—C13—C14—C15	−178.0 (3)
O2—C3—C4—C5	−68.2 (3)	C13—C14—C15—C16	0.7 (5)
N5—C3—C4—C5	110.0 (2)	C14—C15—C16—C17	−1.8 (5)
O1—C1—C4—C3	−176.3 (2)	C15—C16—C17—C18	1.5 (5)
N1—C1—C4—C3	5.5 (3)	C16—C17—C18—C13	−0.2 (5)
O1—C1—C4—C12	−53.1 (3)	C14—C13—C18—C17	−0.9 (4)
N1—C1—C4—C12	128.6 (2)	C12—C13—C18—C17	177.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C15—H15···N2ⁱ	0.98 (3)	2.73 (3)	3.368 (4)	123.0 (19)
C12—H12B···N3ⁱⁱ	0.95 (2)	2.67 (3)	3.542 (4)	152.8 (18)
C9—H9···N4ⁱⁱⁱ	0.97 (3)	2.68 (3)	3.501 (4)	143 (2)
C5—H5B···N4^iv	1.00 (2)	2.71 (3)	3.682 (4)	165.8 (19)
N1—H1···O1^v	0.89 (3)	1.89 (4)	2.774 (3)	175 (3)

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

Experimental details

Crystal data
Chemical formula	C₁₈H₁₅N₅O₂
M_r	333.35
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	297
a, b, c (Å)	8.6247 (13), 16.777 (3), 22.950 (4)
V (Å³)	3320.8 (9)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.41 × 0.10 × 0.04

Data collection
Diffractometer	CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.963, 0.997
No. of measured, independent and observed [I > 2σ(I)] reflections	15340, 2932, 1813
R_int	0.074
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.122, 1.01
No. of reflections	2932
No. of parameters	286
H-atom treatment	All H-atom parameters refined
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.24

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2006), SHELXTL (Bruker, 2003).