cis-(±)-Phen­yl[2,4,5-tri-2-pyridyl-4,5-dihydro­imidazol-1-yl]methanone

Campos-Gaxiola, J.J.; Aguirre, G.; Parra-Hake, M.

doi:10.1107/S1600536807026414

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cis-(±)-Phenyl[2,4,5-tri-2-pyridyl-4,5-dihydroimidazol-1-yl]methanone

J. J. Campos-Gaxiola, G. Aguirre and M. Parra-Hake

In the title compound, C₂₅H₁₉N₅O, two types of intermolecular interactions are observed. Edge-to-face C—H

π interactions between neighbouring molecules form a one-dimensional network, while C—H

N and C—H

O interactions form a two-dimensional network.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807026414/pk2022sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807026414/pk2022Isup2.hkl Contains datablock I

CCDC reference: 654892

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.057
wR factor = 0.140
Data-to-parameter ratio = 12.4

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT480_ALERT_4_C Long H...A H-Bond Reported H5B    ..  N4      ..       2.69 Ang.

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C2     = ...          R
PLAT793_ALERT_1_G Check the Absolute Configuration of C3     = ...          S

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

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

Comment top

The coordination chemistry of transition metals with polypyridyl ligands has progressed considerably during the last decade, and has been widely used for the construction of coordination polymers and other supramolecular structures (Itoh et al., 2005; Albrechy, 2001; Leininger et al., 2000). Complex metal-organic coordination polymers, macrocycles, networks and other metallosupramolecular structures can be constructed by self-assembly from small, easily prepared building blocks, which are combined either through coordinative bonds, hydrogen bonding (Majumder et al., 2006; Burchell et al. 2006; Gallego et al. 2004), π-π (Zou et al., 2006; Liu et al., 2005; Roesky et al., 2003; Wang et al., 2006) or CH/π interactions (Chen et al., 2002; Janiak et al., 2000). Such supramolecular architectures have attracted considerable attention due to the useful electronic, magnetic, optical and catalytic properties of these materials (Lehn, 1995; Séneque et al., 2001). In this direction, previous work in our laboratory has been focused on the coordination chemistry of the ligand cis-(±)2-(2,5-di(pyridin-2-yl)-4,5-dihydro-1H-imidazol-4-yl)pyridine (Larter et al., 1998) with transition metals such as Ni(II), Cu(II), Zn(II) (Parra-Hake et al., 2000) and Cd(II) (Campos-Gaxiola et al., 2007).

As part of our ongoing research on the chemistry of polypyridine ligands we have synthesized Cis-(±)-phenyl[2,4,5-tri(pyridin-2-yl)-4,5- dihydroimidazol-1-yl]methanone (I) in order to modify the coordination environment that could assist in the formation of coordination macromolecules. To gain insight on the new coordination capabilities, the X-ray crystal structure of the title compound has been carried out (Fig. 1).

In the crystal structure, adjacent units are linked together by strong and weak edge-to-face C—H···π interactions (Fig. 2) between pyridyl protons and the pyridyl ring [H···π 3.250 (4) Å and C—H···π 129.3 (2)°], phenyl protons and the pyridyl ring [H···π 2.917 (4) Å and C—H···π 154.0 (2)°](Yang et al., 2006; Jennings et al., 2001; Planas et al., 2006; Jayaraman et al., 2006; Reger et al., 2001), to form one-dimensional chains along the [001] direction. In addition, adjacent units are arranged into a two-dimensional network propagated along the (011) plane via intermolecular C—H···N hydrogen bond interactions between the H-atoms of phenyl or pyridyl rings and pyridyl N atoms as well as C—H···O interactions between pyridyl protons and the O atom of carbonyl group (Fig. 3). The hydrogen bond distances are within the range found for other reported structures (Oxtoby et al., 2003; Thallapally et al., 2003; Kapildev et al., 2005). These interactions may be attributed to the orientation of the aromatic rings, which help to stabilize the structure.

Related literature top

For related literature, see: Albrechy (2001); Burchell & Puddephatt (2006); Campos-Gaxiola, Höpfl & Parra-Hake (2007); Chen & Liu (2002); Gallego et al. (2004); Itoh et al. (2005); Janiak (2000); Jayaraman et al. (2006); Jennings et al. (2001); Kapildev et al. (2005); Larter et al. (1998); Lehn (1995); Leininger et al. (2000); Liu et al. (2005); Majumder et al. (2006); Oxtoby et al. (2003); Parra-Hake et al. (2000); Planas et al. (2006); Reger et al. (2001); Roesky & Andruh (2003); Séneque et al. (2001); Thallapally et al. (2003); Wang et al. (2006); Yang et al. (2006); Zou et al. (2006). It would be helpful to the reader if this long list could be split up into groups concerning different topics, e.g. supramolecular structures, hydrogen bonding, related compounds etc. Please rearrange and rephrase accordingly.

Experimental top

To a stirring solution of cis-(±)2-(2,5-di(pyridin-2-yl)-4,5-dihydro-1H-imidazol-4-yl)pyridine (0.3 g, 0.9966 mmol) in dichloromethane (10 ml) was added Et₃N (0.5 g, 4.9807 mmol). After an additional 5 min, benzoyl chloride (0.28 g, 1.9931 mmol) and 4-dimethylaminopyridine (0.012 g, 0.0982 mmol) was added. The solution was stirred for 22 h at room temperature. The resulting mixture was washed with 0.1 N NaOH (3 × 10 ml). The organic layer was dried over MgSO₄, filtered, and the solvent removed under reduced pressure. The remaining solid was crystallized from CH₂Cl₂/pentane by gas phase diffusion providing colourless crystals that were dried under high vacuum. Yield (0.1930 g, 48%) Mp: 248–250 °K. IR (KBr): 3039, 2929, 2852, 1651, 1613, 1589, 1473, 1438, 1354, 1147, 996, 784, 704 cm^{-1. 1}H NMR (CDCl₃, 500 MHz): d8.34 (ta, J = 4.8, 2H), 8.24 (da, J = 4.6, 2.0, 0.8 Hz,1H), 7.85 (d, J = 7.5 Hz,1H), 7.62 (td, J = 7.7, 2.0 Hz, 1H), 7.42–7.38 (m, 3H),7.32 (td, J = 7.5, 1.6, Hz, 1H), 7.23–7.16 (m, 2H), 7.15 (ddd, J = 7.6,4.8, 1.1 Hz, 1H), 7.09 (t, J = 7.6 Hz, 3H), 6.95(ddd, J = 7.4, J = 4.9, J = 1.0 Hz,1H), 6.91(ddd, J = 7.5,4.8, 1.0 Hz, 1H), 6.08 (d, J = 9.1 Hz, 1H), 6.05 (d, J = 9.1 Hz, 1H). ¹³C NMR (CDCl₃ 125.7 MHz): 168.83, 161.43, 157.52, 156.53, 150.14, 149.04, 148.96, 148.89, 148.33, 136.11, 135.88, 153.47, 131.04, 128.43, 127.77, 124.41, 122.85, 122.34, 121.97, 121.90, 75.40, 70.36. EMIES m/e (int. rel.): [M+H]⁺ 406 (100%).

Structure description top

Computing details top

Data collection: XSCANS (Siemens, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

Figures top

	Fig. 1. Molecular structure of (I) with 30% thermal ellipsoid and labeling schemes.
	Fig. 2. Edge-to-face C—H···π interactions between neighboring molecules form chains along the [001] direction. All interactions are indicated by dashed lines.
	Fig. 3. C—H···N and C—H···O interactions form two-dimensional networks along the (011) plane. All interactions are indicated by dashed lines.

cis-(±)-Phenyl[2,4,5-tri-2-pyridyl-4,5-dihydroimidazol-1-yl]methanone top

Crystal data top

C₂₅H₁₉N₅O	Z = 2
M_r = 405.45	F(000) = 424
Triclinic, P1	D_x = 1.341 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.004 (3) Å	Cell parameters from 39 reflections
b = 10.085 (4) Å	θ = 4.6–11.6°
c = 13.432 (4) Å	µ = 0.09 mm⁻¹
α = 108.65 (4)°	T = 298 K
β = 93.56 (3)°	Prismatic, colourless
γ = 99.84 (4)°	0.5 × 0.42 × 0.14 mm
V = 1004.2 (7) Å³

Data collection top

Bruker P4 diffractometer	R_int = 0.030
Radiation source: fine-focus sealed tube	θ_max = 25.0°, θ_min = 2.2°
Graphite monochromator	h = 0→9
2θ/ω scans	k = −11→11
3758 measured reflections	l = −15→15
3483 independent reflections	3 standard reflections every 97 reflections
1931 reflections with I > 2σ(I)	intensity decay: 13.7%

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)] = 0.057	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0581P)²] where P = (F_o² + 2F_c²)/3
3483 reflections	(Δ/σ)_max = 0.010
280 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₅H₁₉N₅O	γ = 99.84 (4)°
M_r = 405.45	V = 1004.2 (7) Å³
Triclinic, P1	Z = 2
a = 8.004 (3) Å	Mo Kα radiation
b = 10.085 (4) Å	µ = 0.09 mm⁻¹
c = 13.432 (4) Å	T = 298 K
α = 108.65 (4)°	0.5 × 0.42 × 0.14 mm
β = 93.56 (3)°

Data collection top

Bruker P4 diffractometer	R_int = 0.030
3758 measured reflections	3 standard reflections every 97 reflections
3483 independent reflections	intensity decay: 13.7%
1931 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.140	H-atom parameters constrained
S = 0.99	Δρ_max = 0.15 e Å⁻³
3483 reflections	Δρ_min = −0.21 e Å⁻³
280 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
C1	0.4369 (4)	0.1653 (3)	0.7048 (2)	0.0388 (7)
C2	0.4347 (4)	0.1829 (3)	0.5448 (2)	0.0433 (8)
H2B	0.5467	0.1729	0.5211	0.052*
C3	0.4522 (4)	0.3372 (3)	0.6233 (2)	0.0435 (8)
H3B	0.5464	0.4015	0.6087	0.052*
C4	0.4006 (4)	0.1088 (3)	0.7916 (2)	0.0388 (7)
C5	0.3979 (4)	−0.0332 (3)	0.7776 (3)	0.0479 (8)
H5B	0.4261	−0.0932	0.7152	0.057*
C6	0.3527 (5)	−0.0842 (4)	0.8574 (3)	0.0589 (10)
H6A	0.3497	−0.1795	0.8500	0.071*
C7	0.3124 (4)	0.0069 (4)	0.9475 (3)	0.0578 (10)
H7A	0.2817	−0.0248	1.0029	0.069*
C8	0.3181 (4)	0.1471 (4)	0.9550 (3)	0.0539 (9)
H8A	0.2899	0.2086	1.0167	0.065*
C9	0.3068 (4)	0.1464 (3)	0.4479 (2)	0.0415 (8)
C10	0.1672 (4)	0.0362 (3)	0.4222 (3)	0.0513 (9)
H10A	0.1478	−0.0208	0.4644	0.062*
C11	0.0569 (5)	0.0117 (4)	0.3332 (3)	0.0625 (10)
H11A	−0.0397	−0.0612	0.3146	0.075*
C12	0.0912 (5)	0.0962 (4)	0.2719 (3)	0.0583 (10)
H12A	0.0182	0.0819	0.2112	0.070*
C13	0.2343 (5)	0.2014 (4)	0.3016 (3)	0.0557 (9)
H13A	0.2579	0.2573	0.2589	0.067*
C14	0.2925 (4)	0.3986 (3)	0.6281 (2)	0.0407 (8)
C15	0.2940 (5)	0.5330 (3)	0.6216 (3)	0.0561 (9)
H15A	0.3945	0.5878	0.6131	0.067*
C16	0.1466 (6)	0.5843 (4)	0.6277 (3)	0.0683 (11)
H16A	0.1453	0.6745	0.6236	0.082*
C17	0.0008 (5)	0.5011 (4)	0.6399 (3)	0.0669 (11)
H17A	−0.1013	0.5337	0.6449	0.080*
C18	0.0088 (5)	0.3687 (4)	0.6447 (3)	0.0587 (9)
H18A	−0.0912	0.3117	0.6514	0.070*
C19	0.5967 (4)	0.4186 (3)	0.8071 (2)	0.0459 (8)
C20	0.6959 (4)	0.3814 (3)	0.8878 (2)	0.0401 (8)
C21	0.7149 (4)	0.4693 (3)	0.9926 (3)	0.0479 (8)
H21A	0.6591	0.5457	1.0118	0.057*
C22	0.8166 (5)	0.4436 (4)	1.0685 (3)	0.0590 (10)
H22A	0.8246	0.5001	1.1392	0.071*
C23	0.9049 (5)	0.3364 (4)	1.0408 (3)	0.0632 (10)
H23A	0.9764	0.3222	1.0921	0.076*
C24	0.8890 (4)	0.2488 (4)	0.9372 (3)	0.0565 (9)
H24A	0.9488	0.1749	0.9185	0.068*
C25	0.7838 (4)	0.2708 (3)	0.8608 (3)	0.0465 (8)
H25A	0.7721	0.2107	0.7908	0.056*
N1	0.5004 (3)	0.3120 (2)	0.72264 (18)	0.0417 (6)
N2	0.3949 (3)	0.0892 (3)	0.6083 (2)	0.0443 (7)
N3	0.3616 (3)	0.1996 (3)	0.8789 (2)	0.0448 (7)
N4	0.3427 (3)	0.2286 (3)	0.3890 (2)	0.0505 (7)
N5	0.1514 (4)	0.3169 (3)	0.6402 (2)	0.0522 (7)
O1	0.6116 (3)	0.5423 (2)	0.80961 (17)	0.0641 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0382 (18)	0.0368 (17)	0.0389 (18)	0.0068 (14)	0.0009 (14)	0.0105 (15)
C2	0.0434 (19)	0.0461 (18)	0.0357 (18)	0.0063 (15)	0.0033 (15)	0.0092 (15)
C3	0.047 (2)	0.0443 (18)	0.0369 (18)	0.0011 (15)	0.0008 (15)	0.0160 (14)
C4	0.0349 (17)	0.0384 (17)	0.0388 (18)	0.0022 (14)	−0.0060 (14)	0.0119 (15)
C5	0.053 (2)	0.0417 (19)	0.047 (2)	0.0091 (16)	−0.0030 (16)	0.0156 (16)
C6	0.069 (3)	0.043 (2)	0.063 (2)	0.0028 (18)	−0.011 (2)	0.0245 (19)
C7	0.061 (2)	0.060 (2)	0.053 (2)	−0.0052 (19)	−0.0043 (18)	0.0316 (19)
C8	0.056 (2)	0.064 (2)	0.042 (2)	0.0058 (18)	0.0062 (17)	0.0199 (18)
C9	0.048 (2)	0.0400 (18)	0.0363 (18)	0.0123 (16)	0.0086 (15)	0.0102 (15)
C10	0.052 (2)	0.051 (2)	0.048 (2)	0.0009 (17)	0.0044 (17)	0.0180 (17)
C11	0.050 (2)	0.064 (2)	0.059 (2)	−0.0017 (18)	−0.0064 (19)	0.009 (2)
C12	0.054 (2)	0.063 (2)	0.050 (2)	0.0173 (19)	−0.0115 (18)	0.0091 (19)
C13	0.069 (3)	0.055 (2)	0.046 (2)	0.016 (2)	−0.0006 (19)	0.0208 (18)
C14	0.048 (2)	0.0377 (18)	0.0313 (17)	0.0019 (15)	−0.0016 (14)	0.0093 (14)
C15	0.065 (2)	0.041 (2)	0.057 (2)	−0.0011 (18)	−0.0061 (18)	0.0183 (17)
C16	0.084 (3)	0.044 (2)	0.077 (3)	0.017 (2)	−0.013 (2)	0.024 (2)
C17	0.067 (3)	0.061 (2)	0.066 (3)	0.023 (2)	−0.003 (2)	0.008 (2)
C18	0.054 (2)	0.058 (2)	0.064 (2)	0.0099 (19)	0.0120 (19)	0.0217 (19)
C19	0.049 (2)	0.0395 (19)	0.0426 (19)	−0.0007 (16)	0.0011 (16)	0.0103 (15)
C20	0.0380 (18)	0.0421 (18)	0.0351 (18)	−0.0026 (15)	−0.0020 (14)	0.0129 (15)
C21	0.046 (2)	0.0458 (19)	0.046 (2)	0.0005 (16)	0.0052 (16)	0.0133 (16)
C22	0.065 (2)	0.063 (2)	0.0367 (19)	−0.005 (2)	−0.0083 (18)	0.0106 (17)
C23	0.059 (2)	0.070 (3)	0.058 (3)	−0.002 (2)	−0.0115 (19)	0.030 (2)
C24	0.050 (2)	0.053 (2)	0.067 (3)	0.0056 (17)	−0.0057 (19)	0.0248 (19)
C25	0.0432 (19)	0.049 (2)	0.0407 (19)	−0.0006 (16)	0.0011 (15)	0.0117 (15)
N1	0.0479 (16)	0.0360 (14)	0.0337 (14)	−0.0023 (12)	−0.0069 (12)	0.0095 (11)
N2	0.0532 (17)	0.0366 (14)	0.0405 (16)	0.0062 (12)	0.0007 (13)	0.0117 (12)
N3	0.0463 (16)	0.0445 (15)	0.0422 (16)	0.0042 (13)	0.0040 (13)	0.0157 (13)
N4	0.0567 (18)	0.0476 (16)	0.0436 (16)	0.0035 (14)	0.0008 (14)	0.0152 (14)
N5	0.0569 (19)	0.0499 (17)	0.0538 (18)	0.0121 (15)	0.0124 (15)	0.0213 (14)
O1	0.0910 (19)	0.0381 (14)	0.0542 (15)	−0.0024 (13)	−0.0156 (13)	0.0157 (11)

Geometric parameters (Å, º) top

C1—N2	1.267 (4)	C12—H12A	0.9300
C1—N1	1.416 (4)	C13—N4	1.340 (4)
C1—C4	1.476 (4)	C13—H13A	0.9300
C2—N2	1.473 (4)	C14—N5	1.331 (4)
C2—C9	1.509 (4)	C14—C15	1.384 (4)
C2—C3	1.552 (4)	C15—C16	1.363 (5)
C2—H2B	0.9800	C15—H15A	0.9300
C3—N1	1.477 (4)	C16—C17	1.368 (5)
C3—C14	1.509 (4)	C16—H16A	0.9300
C3—H3B	0.9800	C17—C18	1.369 (5)
C4—N3	1.330 (4)	C17—H17A	0.9300
C4—C5	1.380 (4)	C18—N5	1.331 (4)
C5—C6	1.371 (4)	C18—H18A	0.9300
C5—H5B	0.9300	C19—O1	1.222 (3)
C6—C7	1.361 (5)	C19—N1	1.366 (4)
C6—H6A	0.9300	C19—C20	1.483 (4)
C7—C8	1.377 (4)	C20—C25	1.383 (4)
C7—H7A	0.9300	C20—C21	1.385 (4)
C8—N3	1.332 (4)	C21—C22	1.381 (4)
C8—H8A	0.9300	C21—H21A	0.9300
C9—N4	1.327 (4)	C22—C23	1.358 (5)
C9—C10	1.373 (4)	C22—H22A	0.9300
C10—C11	1.369 (4)	C23—C24	1.373 (5)
C10—H10A	0.9300	C23—H23A	0.9300
C11—C12	1.369 (5)	C24—C25	1.384 (4)
C11—H11A	0.9300	C24—H24A	0.9300
C12—C13	1.362 (5)	C25—H25A	0.9300

N2—C1—N1	114.6 (3)	C12—C13—H13A	118.3
N2—C1—C4	122.2 (3)	N5—C14—C15	122.2 (3)
N1—C1—C4	122.7 (3)	N5—C14—C3	116.2 (3)
N2—C2—C9	113.5 (3)	C15—C14—C3	121.6 (3)
N2—C2—C3	105.2 (2)	C16—C15—C14	119.3 (3)
C9—C2—C3	114.1 (2)	C16—C15—H15A	120.3
N2—C2—H2B	107.9	C14—C15—H15A	120.3
C9—C2—H2B	107.9	C15—C16—C17	119.0 (3)
C3—C2—H2B	107.9	C15—C16—H16A	120.5
N1—C3—C14	111.5 (2)	C17—C16—H16A	120.5
N1—C3—C2	98.9 (2)	C18—C17—C16	118.4 (4)
C14—C3—C2	115.8 (3)	C18—C17—H17A	120.8
N1—C3—H3B	110.1	C16—C17—H17A	120.8
C14—C3—H3B	110.1	N5—C18—C17	123.8 (4)
C2—C3—H3B	110.1	N5—C18—H18A	118.1
N3—C4—C5	123.3 (3)	C17—C18—H18A	118.1
N3—C4—C1	116.2 (3)	O1—C19—N1	119.1 (3)
C5—C4—C1	120.3 (3)	O1—C19—C20	121.1 (3)
C6—C5—C4	118.7 (3)	N1—C19—C20	119.5 (3)
C6—C5—H5B	120.6	C25—C20—C21	118.8 (3)
C4—C5—H5B	120.6	C25—C20—C19	122.2 (3)
C7—C6—C5	118.9 (3)	C21—C20—C19	118.7 (3)
C7—C6—H6A	120.5	C22—C21—C20	120.1 (3)
C5—C6—H6A	120.5	C22—C21—H21A	119.9
C6—C7—C8	118.6 (3)	C20—C21—H21A	119.9
C6—C7—H7A	120.7	C23—C22—C21	120.6 (3)
C8—C7—H7A	120.7	C23—C22—H22A	119.7
N3—C8—C7	123.8 (3)	C21—C22—H22A	119.7
N3—C8—H8A	118.1	C22—C23—C24	120.2 (3)
C7—C8—H8A	118.1	C22—C23—H23A	119.9
N4—C9—C10	123.1 (3)	C24—C23—H23A	119.9
N4—C9—C2	114.1 (3)	C23—C24—C25	119.9 (3)
C10—C9—C2	122.8 (3)	C23—C24—H24A	120.1
C11—C10—C9	118.8 (3)	C25—C24—H24A	120.1
C11—C10—H10A	120.6	C24—C25—C20	120.4 (3)
C9—C10—H10A	120.6	C24—C25—H25A	119.8
C10—C11—C12	118.9 (3)	C20—C25—H25A	119.8
C10—C11—H11A	120.5	C19—N1—C1	132.2 (3)
C12—C11—H11A	120.5	C19—N1—C3	121.1 (2)
C13—C12—C11	118.8 (3)	C1—N1—C3	106.6 (2)
C13—C12—H12A	120.6	C1—N2—C2	107.4 (2)
C11—C12—H12A	120.6	C4—N3—C8	116.6 (3)
N4—C13—C12	123.3 (3)	C9—N4—C13	117.1 (3)
N4—C13—H13A	118.3	C14—N5—C18	117.3 (3)

N2—C2—C3—N1	25.5 (3)	N1—C19—C20—C21	−145.6 (3)
C9—C2—C3—N1	150.6 (3)	C25—C20—C21—C22	−1.7 (5)
N2—C2—C3—C14	−93.6 (3)	C19—C20—C21—C22	−175.4 (3)
C9—C2—C3—C14	31.4 (4)	C20—C21—C22—C23	3.0 (5)
N2—C1—C4—N3	−144.7 (3)	C21—C22—C23—C24	−2.4 (6)
N1—C1—C4—N3	26.8 (4)	C22—C23—C24—C25	0.6 (5)
N2—C1—C4—C5	31.4 (4)	C23—C24—C25—C20	0.7 (5)
N1—C1—C4—C5	−157.1 (3)	C21—C20—C25—C24	−0.2 (5)
N3—C4—C5—C6	0.0 (5)	C19—C20—C25—C24	173.3 (3)
C1—C4—C5—C6	−175.8 (3)	O1—C19—N1—C1	−168.1 (3)
C4—C5—C6—C7	−0.1 (5)	C20—C19—N1—C1	18.4 (5)
C5—C6—C7—C8	0.2 (5)	O1—C19—N1—C3	16.1 (5)
C6—C7—C8—N3	−0.3 (5)	C20—C19—N1—C3	−157.4 (3)
N2—C2—C9—N4	−178.9 (3)	N2—C1—N1—C19	−160.5 (3)
C3—C2—C9—N4	60.5 (4)	C4—C1—N1—C19	27.4 (5)
N2—C2—C9—C10	0.0 (4)	N2—C1—N1—C3	15.7 (3)
C3—C2—C9—C10	−120.6 (3)	C4—C1—N1—C3	−156.4 (3)
N4—C9—C10—C11	−1.8 (5)	C14—C3—N1—C19	−85.2 (3)
C2—C9—C10—C11	179.4 (3)	C2—C3—N1—C19	152.4 (3)
C9—C10—C11—C12	1.2 (5)	C14—C3—N1—C1	98.1 (3)
C10—C11—C12—C13	0.2 (5)	C2—C3—N1—C1	−24.3 (3)
C11—C12—C13—N4	−1.1 (5)	N1—C1—N2—C2	2.3 (3)
N1—C3—C14—N5	−62.1 (3)	C4—C1—N2—C2	174.4 (3)
C2—C3—C14—N5	49.9 (4)	C9—C2—N2—C1	−143.8 (3)
N1—C3—C14—C15	117.1 (3)	C3—C2—N2—C1	−18.3 (3)
C2—C3—C14—C15	−130.9 (3)	C5—C4—N3—C8	−0.1 (4)
N5—C14—C15—C16	0.0 (5)	C1—C4—N3—C8	175.9 (3)
C3—C14—C15—C16	−179.2 (3)	C7—C8—N3—C4	0.2 (5)
C14—C15—C16—C17	−0.1 (5)	C10—C9—N4—C13	0.9 (5)
C15—C16—C17—C18	−0.5 (6)	C2—C9—N4—C13	179.8 (3)
C16—C17—C18—N5	1.4 (6)	C12—C13—N4—C9	0.6 (5)
O1—C19—C20—C25	−132.3 (3)	C15—C14—N5—C18	0.7 (4)
N1—C19—C20—C25	41.0 (4)	C3—C14—N5—C18	180.0 (3)
O1—C19—C20—C21	41.1 (5)	C17—C18—N5—C14	−1.5 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.57	3.469 (5)	163
C15—H15A···N4ⁱ	0.93	2.56	3.483 (5)	171
C5—H5B···N4ⁱⁱ	0.93	2.69	3.515 (5)	149
C21—H21A···N3ⁱⁱⁱ	0.93	2.56	3.413 (5)	153

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

Experimental details

Crystal data
Chemical formula	C₂₅H₁₉N₅O
M_r	405.45
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.004 (3), 10.085 (4), 13.432 (4)
α, β, γ (°)	108.65 (4), 93.56 (3), 99.84 (4)
V (Å³)	1004.2 (7)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.5 × 0.42 × 0.14

Data collection
Diffractometer	Bruker P4
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	3758, 3483, 1931
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.057, 0.140, 0.99
No. of reflections	3483
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.21

Computer programs: XSCANS (Siemens, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998), SHELXTL.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C13—H13A···O1ⁱ	0.93	2.57	3.469 (5)	162.6
C15—H15A···N4ⁱ	0.93	2.56	3.483 (5)	171.1
C5—H5B···N4ⁱⁱ	0.93	2.69	3.515 (5)	149.0
C21—H21A···N3ⁱⁱⁱ	0.93	2.56	3.413 (5)	153.1

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

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