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In the title compound, C16H18N6O, an N-carbonyl­imidazole derivative of pyrazoline-1-carboximid­amide, the π-electron density of the N atom in the 1-position on the pyrazoline ring is delocalized through the amidine moiety and the adjacent carbonyl group. The imidazole ring, though coplanar with the rest of the mol­ecule, is deconjugated. The pyrazoline ring adopts a flat-envelope conformation, having the substituted phenyl ring oriented perpendicular to the mean plane of the heterocycle. Both of the two potential hydrogen-bond donors are involved in intramolecular hydrogen-bonding interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S010827010400890X/jz1613sup1.cif
Contains datablocks global, VI

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S010827010400890X/jz1613VIsup2.hkl
Contains datablock VI

CCDC reference: 243614

Comment top

Recently, as a part of our program aimed at developing potent inhibitor(s) of nitric oxide synthase based on heterocyclic derivatives of aminoguanidine (Griffith & Gross, 1996), we reported a study of ring-closure reactions of 4,5-dihydro-3-methyl-5-(2-hydroxyphenyl)-1H-pyrazole-1-carboximidamide, (Ia), with C1–C3 reagents (Světlik & Liptaj, 2002). We have found that cyclocondensation of pyrazoline (Ia) with 1,1'-carbonyldiimidazole, (II), afforded a highly strained tetracyclic molecule, (III). Formation of the novel 5,11-methano[1,2,4]triazolo[1,2-c][1,2,4]benzoxadiazepine, (III), a prototype of a new bridged heterocyclic family, can be envisaged by the intermediacy of two transient structures, (IV) and (V) (Světlik & Liptaj, 2002). Since the inertness of the phenol hydroxy group in (Ia) towards (II) seemed us to be rather striking, it would be of interest to support the postulated reaction mechanism. For this purpose we chose a related tolyl derivative, (Ib), as a vehicle for better insight into the heterocyclization mentioned above. Thus, under similar conditions, condensation of (Ib) gave rise to a compound, the spectral properties of which are compatible with the first type of the two assumed intermediates, i.e. imidazole-1-carboxamide, (VI). To confirm this and, at the same time, to establish the spatial distribution of the functional groups for subsequent molecular-modeling study, we selected compound (VI) for X-ray structural analysis.

The molecular structure and the atom-numbering scheme of (VI) are shown in Fig. 1. As can be seen, the compound is indeed the tolyl derivative of the transient intermediate (IV), i.e. it consists of a substituted pyrazoline ring and a carbonylimidazole function attached to the amidine N atom. The overall conformation of the molecule can also be inferred from Fig. 1. Calculation of the least-squares plane has shown that the pyrazoline ring adopts a flat-envelope conformation, with atom C5 as the flap; the deviation of the out-of-plane atom from the mean plane of the remaining four atoms [r.m.s. deviation 0.006 (2) Å] is 0.307 (3) Å. The tolyl group occupies a pseudo-axial position and, as a result, it is approximately perpendicular to the mean plane of the pyrazoline ring [dihedral angle 77.9 (1)°]. The aryl ring is situated about the exocyclic C5—C6 bond in such a manner that the ring does not bisect the heterocyclic ring but is rotated towards atom N1 [N1—C5—C6—C7 = −20.3 (2)°].

Selected bond lengths and angles in the molecule are listed in Table 1. It has been reported (Krishna et al., 1999) that the N—N bond length in the pyrazoline ring lies in a wide range, from 1.385 (4) to 1.234 (8) Å, depending on the substituents bonded to the N atoms; accordingly, the length of the adjacent CN bond ranges from 1.288 (4) to 1.461 (8) Å. This is variation is caused by varying degrees of conjugation within the π-electron portion of the pyrazoline ring, which is sensitively affected by the nature of substituent(s) bonded to the atoms of the π system. The N1—N2 bond length [1.401 (2) Å] found in the present derivative further extends this range, approximating to a purely single bond (1.41 Å; Burke-Laing & Laing, 1976). Similarly, the corresponding N2C3 bond [1.280 (2) Å] has pure double-bond character (1.28 Å). That the lone-pair electrons on atom N1 are delocalized through conjugation with the amidine group rather than the N2C3 double bond is also seen in the N1—C14 bond length [1.342 (2) Å], which is intermediate between a single and double bond and equivalent to the two C—N bonds in the amidine moiety. The conjugation is further extended to the N4—C15—O1 moiety as reflected in its molecular dimensions (Table 1), which are comparable to those typically found in amides (Benedetti et al., 1983). In contrast, the imidazole ring is deconjugated (though coplanar) with the adjacent π system, as indicated by (i) the N5—C15 bond distance [1.435 (2) Å], which is slightly longer than the value [1.425 (3) Å] reported for a pure Nsp2—Csp2 single bond (Adler at al., 1976) and (ii) the pattern of bond lengths and angles within the imidazole ring, which is identical to that found in unsubstituted imidazole or its derivatives containing substituents not involved in conjugation with the aromatic system (e.g. Perry et al., 1980; Moriuchi et al. 2001) as revealed by a search of the Cambridge Structural Database (Allen et al., 1983). Other bond distances and angles are close to those generally expected.

The molecule is stabilized by two intramolecular hydrogen bonds between atom N3 as a double hydrogen-bond donor, and atoms O1 and N2 as acceptors (Table 2). Besides these H-bonds, there is also a short intramolecular C16—H···N4 contact which, based on its H···N distance (Table 2), can be regarded as a weak hydrogen-bonding interaction (Taylor & Kennard, 1982) and may contribute to the planarity of the imidazole–carboxamide moiety. An analysis of the intermolecular contacts reveals two weak intermolecular C—H···π(aryl) interactions [H8···Cg1 = 3.01 Å and H13C···Cg2 = 3.08 Å, where Cg1 and Cg2 are the centroids of the phenyl ring of the molecules at (x-y,x,-z) and (y,-x + y,-z), respectively] and a number of van der Waals interactions.

Experimental top

The title compound, (VI), was synthesized by reaction of 3-methyl-5- (4-methylphenyl)-4,5-dihydro-1H-pyrazole-1-carboximidamide acetate, prepared according to the method described by Světlik & Sallai (2002), with 1,1'-carbonyldiimidazole according to the method of Světlik & Liptaj (2002). A solution of the pyrazole derivative (0.5 mmol) and 1,1'-carbonyldiimidazole (5 ml) was heated at 373 K for 1 h. The reaction mixture was concentrated in vacuo and the residue was dissolved in dichloromethane (10 ml). After washing with 5% HCl (2 x 5 ml) and water (1 x 5 ml), the organic layer was dried (MgSO4) and concentrated. The resulting oil was dissolved in ethyl acetate (5 ml) and left to stand at room temperature. The crystalline material was collected and recrystallized from acetone (yield 0.040 g, 26%, m.p. 446–448 K). IR (KBr): 3470 (NH2), 3330 (NH2 assoc.), 1663 (C=O + C=N), 1596 (C=N), 1562 (C=C) cm−1; 1H NMR (CDCl3): 2.17 (3H, s, Me), 2.31 (3H, s, Me-tolyl), 2.78 (1H, dd, J=18.3 and 5.4 Hz, 4-Ha pyrazole), 3.46 (1H, dd, J= 18.3 and 11.7 Hz, 4-Hb pyrazole), 5.48 (1H, dd, J=11.7 and 5.4 Hz, 5-H pyrazole), 6.56 (1H, brs, NH), 6.89 (1H, s, 4-H imidazole), 7.07 (2H, d, H-3' and H-5'), 7.16 (2H, d, H-2' and H-6'), 7.30 (1H, s, 5-H imidazole), 7.90 (1H, s, 2-H imidazole), 8.72 (1-H, brs, NH assoc.); 13C NMR (CDCl3): 16.2 (Me), 21.0 (Me-tolyl), 47.4 (CH2), 60.9 (CH), 116.8 (CH-5 imidazole), 124.8 (CH-2' + CH-6'), 129.1 (CH-4 imidazole), 129.8 (CH-3' + CH-5'), 137.3 (CH-2 imidazole), 137.6 (C-4'), 139.4 (C-1'), 157.2,157.3 (CON, N—C=N), 158.1 (C-3 pyrazole).

Refinement top

The two H atoms bonded to N3 were included in the refinement using isotropic displacement parameters; other H atoms were refined with fixed geometry, riding on their carrier atoms, with Uiso set to 1.2 (1.5 for the methyl H atoms) times Ueq of the parent atom. The C12 methyl H atoms were treated by using a twofold disorder model. Reflection −1 2 0, affected by secondary extinction, was omitted from the refinement.

Computing details top

Data collection: XSCANS (Siemens, 1991); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLUTON (Spek, 1992); software used to prepare material for publication: SHELXL97.

Figures top
[Figure 1] Fig. 1. A view of the title compound, with its numbering scheme. Displacement ellipsoids are shown at the 35% probability level and H atoms are shown as circles of arbitrary radii.
N-{(1E)-Amino[3-methyl-5-(4-methylphenyl)-4,5-dihydro-1H-pyrazol-1- yl]methylene}-1H-imidazole-1-carboxamide top
Crystal data top
C16H18N6OMelting point: 720 K
Mr = 310.36Mo Kα radiation, λ = 0.71073 Å
Trigonal, R3Cell parameters from 25 reflections
a = 32.322 (5) Åθ = 9–20°
c = 8.084 (2) ŵ = 0.09 mm1
V = 7314 (2) Å3T = 293 K
Z = 18Prism, colourless
F(000) = 29520.35 × 0.30 × 0.25 mm
Dx = 1.267 Mg m3
Data collection top
Siemens P4
diffractometer
Rint = 0.040
Radiation source: fine-focus sealed tubeθmax = 25.1°, θmin = 1.3°
Graphite monochromatorh = 3838
ω/2θ scansk = 3838
3678 measured reflectionsl = 19
2872 independent reflections3 standard reflections every 97 reflections
2061 reflections with I > 2σ(I) intensity decay: 2%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0531P)2 + 2.798P]
where P = (Fo2 + 2Fc2)/3
2872 reflections(Δ/σ)max = 0.001
218 parametersΔρmax = 0.14 e Å3
0 restraintsΔρmin = 0.16 e Å3
Crystal data top
C16H18N6OZ = 18
Mr = 310.36Mo Kα radiation
Trigonal, R3µ = 0.09 mm1
a = 32.322 (5) ÅT = 293 K
c = 8.084 (2) Å0.35 × 0.30 × 0.25 mm
V = 7314 (2) Å3
Data collection top
Siemens P4
diffractometer
Rint = 0.040
3678 measured reflections3 standard reflections every 97 reflections
2872 independent reflections intensity decay: 2%
2061 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0400 restraints
wR(F2) = 0.108H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.14 e Å3
2872 reflectionsΔρmin = 0.16 e Å3
218 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
N10.51395 (5)0.07997 (5)0.52788 (16)0.0472 (3)
N20.50330 (5)0.09956 (5)0.66483 (18)0.0519 (4)
C30.47543 (6)0.11434 (6)0.6142 (2)0.0545 (5)
C40.46290 (6)0.10509 (7)0.4350 (2)0.0579 (5)
H4A0.46680.13350.37990.070*
H4B0.43030.07930.42010.070*
C50.49900 (6)0.09123 (6)0.3703 (2)0.0479 (4)
H50.48310.06280.30010.057*
C60.54057 (6)0.13154 (6)0.2800 (2)0.0471 (4)
C70.58232 (6)0.16343 (6)0.3588 (2)0.0550 (5)
H70.58610.15960.47080.066*
C80.61877 (7)0.20114 (7)0.2731 (3)0.0642 (5)
H80.64680.22220.32830.077*
C90.61424 (7)0.20798 (8)0.1066 (3)0.0693 (6)
C100.57281 (8)0.17520 (9)0.0282 (3)0.0807 (7)
H100.56930.17850.08440.097*
C110.53652 (7)0.13763 (8)0.1132 (3)0.0685 (5)
H110.50890.11610.05720.082*
C120.65423 (9)0.24926 (10)0.0142 (4)0.1090 (10)
H12A0.67100.27580.08810.163*0.50
H12B0.64120.25850.07570.163*0.50
H12C0.67590.23970.02830.163*0.50
H12D0.65440.24020.09870.163*0.50
H12E0.68420.25750.06510.163*0.50
H12F0.64950.27630.01770.163*0.50
C130.45627 (8)0.13673 (8)0.7273 (3)0.0771 (6)
H13A0.47000.14010.83510.116*
H13B0.42220.11700.73440.116*
H13C0.46420.16760.68560.116*
C140.54185 (5)0.06036 (5)0.5431 (2)0.0433 (4)
N30.55710 (6)0.05794 (6)0.6932 (2)0.0574 (4)
H3A0.5706 (7)0.0407 (7)0.704 (2)0.068 (6)*
H3B0.5452 (8)0.0679 (8)0.779 (3)0.083 (7)*
N40.55077 (5)0.04537 (5)0.40127 (17)0.0462 (3)
C150.57830 (6)0.02551 (6)0.3992 (2)0.0466 (4)
O10.60074 (5)0.01906 (5)0.50799 (16)0.0666 (4)
N50.58038 (5)0.00980 (5)0.23495 (17)0.0463 (3)
C160.55479 (6)0.00935 (6)0.1004 (2)0.0543 (4)
H160.53390.02130.10120.065*
N60.56258 (6)0.00957 (6)0.0293 (2)0.0649 (4)
C170.59532 (7)0.02244 (6)0.0239 (3)0.0626 (5)
H170.60790.03700.04220.075*
C180.60639 (6)0.01110 (6)0.1837 (3)0.0569 (5)
H180.62740.01630.24720.068*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
N10.0510 (8)0.0534 (8)0.0445 (8)0.0317 (7)0.0015 (6)0.0005 (6)
N20.0511 (8)0.0512 (8)0.0527 (9)0.0252 (7)0.0068 (7)0.0017 (7)
C30.0455 (9)0.0488 (10)0.0686 (12)0.0232 (8)0.0095 (9)0.0042 (9)
C40.0466 (10)0.0585 (11)0.0730 (13)0.0295 (9)0.0005 (9)0.0070 (9)
C50.0466 (9)0.0493 (9)0.0494 (10)0.0252 (8)0.0076 (8)0.0008 (8)
C60.0485 (9)0.0503 (9)0.0504 (10)0.0306 (8)0.0016 (8)0.0014 (8)
C70.0520 (10)0.0566 (11)0.0556 (11)0.0265 (9)0.0006 (9)0.0011 (9)
C80.0501 (10)0.0609 (12)0.0791 (14)0.0259 (9)0.0017 (10)0.0028 (10)
C90.0591 (12)0.0729 (13)0.0827 (15)0.0381 (11)0.0182 (11)0.0268 (12)
C100.0745 (15)0.0989 (17)0.0641 (14)0.0399 (13)0.0046 (12)0.0272 (13)
C110.0633 (12)0.0776 (13)0.0579 (12)0.0302 (11)0.0075 (10)0.0094 (11)
C120.0793 (16)0.114 (2)0.125 (2)0.0415 (15)0.0327 (16)0.0580 (18)
C130.0769 (14)0.0767 (14)0.0918 (16)0.0490 (12)0.0178 (12)0.0005 (12)
C140.0378 (8)0.0397 (8)0.0474 (10)0.0157 (7)0.0048 (7)0.0011 (7)
N30.0617 (10)0.0695 (10)0.0498 (10)0.0396 (9)0.0117 (8)0.0039 (8)
N40.0474 (8)0.0480 (8)0.0486 (8)0.0280 (7)0.0044 (6)0.0017 (6)
C150.0393 (9)0.0452 (9)0.0520 (10)0.0188 (7)0.0029 (8)0.0023 (8)
O10.0675 (8)0.0907 (10)0.0617 (8)0.0546 (8)0.0148 (7)0.0031 (7)
N50.0414 (7)0.0449 (7)0.0540 (9)0.0227 (6)0.0002 (6)0.0010 (6)
C160.0574 (11)0.0587 (11)0.0529 (11)0.0337 (9)0.0045 (9)0.0001 (9)
N60.0753 (11)0.0689 (10)0.0564 (10)0.0404 (9)0.0004 (8)0.0059 (8)
C170.0625 (12)0.0531 (11)0.0719 (14)0.0287 (10)0.0139 (10)0.0031 (10)
C180.0472 (10)0.0546 (10)0.0746 (13)0.0298 (9)0.0032 (9)0.0023 (10)
Geometric parameters (Å, º) top
N1—C141.342 (2)C12—H12B0.9600
N1—N21.401 (2)C12—H12C0.9600
N1—C51.471 (2)C12—H12D0.9600
N2—C31.280 (2)C12—H12E0.9600
C3—C131.480 (3)C12—H12F0.9600
C3—C41.493 (3)C13—H13A0.9600
C4—C51.536 (2)C13—H13B0.9600
C4—H4A0.9700C13—H13C0.9600
C4—H4B0.9700C14—N31.327 (2)
C5—C61.512 (2)C14—N41.331 (2)
C5—H50.9800N3—H3A0.87 (2)
C6—C71.378 (2)N3—H3B0.92 (2)
C6—C111.378 (3)N4—C151.332 (2)
C7—C81.385 (3)C15—O11.2224 (19)
C7—H70.9300C15—N51.435 (2)
C8—C91.383 (3)N5—C161.362 (2)
C8—H80.9300N5—C181.379 (2)
C9—C101.378 (3)C16—N61.300 (2)
C9—C121.511 (3)C16—H160.9300
C10—C111.378 (3)N6—C171.385 (2)
C10—H100.9300C17—C181.342 (3)
C11—H110.9300C17—H170.9300
C12—H12A0.9600C18—H180.9300
C14—N1—N2121.07 (13)H12A—C12—H12D141.1
C14—N1—C5125.26 (14)H12B—C12—H12D56.3
N2—N1—C5112.77 (12)H12C—C12—H12D56.3
C3—N2—N1107.09 (14)C9—C12—H12E109.5
N2—C3—C13121.98 (18)H12A—C12—H12E56.3
N2—C3—C4114.00 (15)H12B—C12—H12E141.1
C13—C3—C4123.98 (17)H12C—C12—H12E56.3
C3—C4—C5102.65 (14)H12D—C12—H12E109.5
C3—C4—H4A111.2C9—C12—H12F109.5
C5—C4—H4A111.2H12A—C12—H12F56.3
C3—C4—H4B111.2H12B—C12—H12F56.3
C5—C4—H4B111.2H12C—C12—H12F141.1
H4A—C4—H4B109.1H12D—C12—H12F109.5
N1—C5—C6111.79 (13)H12E—C12—H12F109.5
N1—C5—C499.72 (13)C3—C13—H13A109.5
C6—C5—C4112.99 (14)C3—C13—H13B109.5
N1—C5—H5110.6H13A—C13—H13B109.5
C6—C5—H5110.6C3—C13—H13C109.5
C4—C5—H5110.6H13A—C13—H13C109.5
C7—C6—C11118.23 (17)H13B—C13—H13C109.5
C7—C6—C5122.49 (16)N3—C14—N4127.73 (16)
C11—C6—C5119.26 (16)N3—C14—N1117.93 (16)
C6—C7—C8120.73 (18)N4—C14—N1114.34 (14)
C6—C7—H7119.6C14—N3—H3A117.0 (13)
C8—C7—H7119.6C14—N3—H3B115.6 (14)
C9—C8—C7121.06 (19)H3A—N3—H3B125 (2)
C9—C8—H8119.5C14—N4—C15120.31 (14)
C7—C8—H8119.5O1—C15—N4132.00 (16)
C10—C9—C8117.68 (19)O1—C15—N5117.94 (14)
C10—C9—C12121.7 (2)N4—C15—N5110.06 (14)
C8—C9—C12120.6 (2)C16—N5—C18105.70 (15)
C11—C10—C9121.3 (2)C16—N5—C15127.36 (14)
C11—C10—H10119.3C18—N5—C15126.80 (14)
C9—C10—H10119.3N6—C16—N5112.92 (16)
C10—C11—C6120.92 (19)N6—C16—H16123.5
C10—C11—H11119.5N5—C16—H16123.5
C6—C11—H11119.5C16—N6—C17104.35 (16)
C9—C12—H12A109.5C18—C17—N6110.86 (17)
C9—C12—H12B109.5C18—C17—H17124.6
H12A—C12—H12B109.5N6—C17—H17124.6
C9—C12—H12C109.5C17—C18—N5106.16 (16)
H12A—C12—H12C109.5C17—C18—H18126.9
H12B—C12—H12C109.5N5—C18—H18126.9
C9—C12—H12D109.5
C14—N1—N2—C3178.46 (14)C9—C10—C11—C60.2 (3)
C5—N1—N2—C311.83 (18)C7—C6—C11—C101.4 (3)
N1—N2—C3—C13179.20 (16)C5—C6—C11—C10177.11 (19)
N1—N2—C3—C41.51 (19)N2—N1—C14—N33.3 (2)
N2—C3—C4—C513.03 (19)C5—N1—C14—N3171.66 (15)
C13—C3—C4—C5169.33 (17)N2—N1—C14—N4176.83 (13)
C14—N1—C5—C668.29 (19)C5—N1—C14—N48.5 (2)
N2—N1—C5—C6100.91 (15)N3—C14—N4—C150.6 (3)
C14—N1—C5—C4172.03 (14)N1—C14—N4—C15179.54 (14)
N2—N1—C5—C418.77 (16)C14—N4—C15—O13.6 (3)
C3—C4—C5—N117.53 (16)C14—N4—C15—N5176.64 (13)
C3—C4—C5—C6101.26 (16)O1—C15—N5—C16173.25 (16)
N1—C5—C6—C720.3 (2)N4—C15—N5—C166.9 (2)
C4—C5—C6—C791.3 (2)O1—C15—N5—C181.9 (2)
N1—C5—C6—C11161.29 (16)N4—C15—N5—C18177.96 (15)
C4—C5—C6—C1187.2 (2)C18—N5—C16—N60.3 (2)
C11—C6—C7—C81.3 (3)C15—N5—C16—N6176.24 (15)
C5—C6—C7—C8177.14 (16)N5—C16—N6—C170.1 (2)
C6—C7—C8—C90.3 (3)C16—N6—C17—C180.1 (2)
C7—C8—C9—C101.9 (3)N6—C17—C18—N50.3 (2)
C7—C8—C9—C12180.0 (2)C16—N5—C18—C170.33 (19)
C8—C9—C10—C111.8 (3)C15—N5—C18—C17176.31 (15)
C12—C9—C10—C11179.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.87 (2)2.15 (2)2.754 (2)126 (2)
N3—H3B···N20.92 (2)2.26 (2)2.688 (2)108 (2)
C16—H16···N40.932.522.728 (2)93

Experimental details

Crystal data
Chemical formulaC16H18N6O
Mr310.36
Crystal system, space groupTrigonal, R3
Temperature (K)293
a, c (Å)32.322 (5), 8.084 (2)
V3)7314 (2)
Z18
Radiation typeMo Kα
µ (mm1)0.09
Crystal size (mm)0.35 × 0.30 × 0.25
Data collection
DiffractometerSiemens P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3678, 2872, 2061
Rint0.040
(sin θ/λ)max1)0.597
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.040, 0.108, 1.01
No. of reflections2872
No. of parameters218
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.14, 0.16

Computer programs: XSCANS (Siemens, 1991), XSCANS, SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), PLUTON (Spek, 1992), SHELXL97.

Selected geometric parameters (Å, º) top
N1—C141.342 (2)C14—N31.327 (2)
N1—N21.401 (2)C14—N41.331 (2)
N1—C51.471 (2)N4—C151.332 (2)
N2—C31.280 (2)C15—O11.2224 (19)
C3—C41.493 (3)C15—N51.435 (2)
C4—C51.536 (2)
C14—N1—N2121.07 (13)N4—C14—N1114.34 (14)
C14—N1—C5125.26 (14)C14—N4—C15120.31 (14)
N2—N1—C5112.77 (12)O1—C15—N4132.00 (16)
N3—C14—N4127.73 (16)O1—C15—N5117.94 (14)
N3—C14—N1117.93 (16)N4—C15—N5110.06 (14)
N1—C5—C6—C720.3 (2)C14—N4—C15—O13.6 (3)
N2—N1—C14—N33.3 (2)N4—C15—N5—C166.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···O10.87 (2)2.15 (2)2.754 (2)126 (2)
N3—H3B···N20.92 (2)2.26 (2)2.688 (2)108 (2)
C16—H16···N40.932.522.728 (2)93
 

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