4′-[4-(Imidazol-1-yl)phen­yl]-2,2′:6′,2′′-terpyridine (IPTP)

Wang, C.X.; Li, L.; Yu, W.T.; Yang, J.X.; Wu, J.Y.

doi:10.1107/S1600536805041000

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4'-[4-(Imidazol-1-yl)phenyl]-2,2':6',2''-terpyridine (IPTP)

C. X. Wang, L. Li, W. T. Yu, J. X. Yang and J. Y. Wu

The title compound (IPTP), C₂₄H₁₇N₅, has been synthesized and characterized by ¹H NMR, ¹³C NMR and single-crystal X-ray diffraction. The three pyridyl rings are almost coplanar. The benzene ring forms dihedral angles of 49.59 (17) and 19.18 (13)° with the central pyridyl ring and the imidazole ring, respectively.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805041000/ww6443sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536805041000/ww6443Isup2.hkl Contains datablock I

CCDC reference: 296700

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.004 Å
R factor = 0.051
wR factor = 0.156
Data-to-parameter ratio = 13.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         43 Perc.
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C2

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 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
   1 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

Comment top

Polypyridine ligands have played an important role in many areas. In particular, the chelating ligand terpyridine (terpy) and its functionalized derivatives have been studied extensively as outstanding complexing agents for a wide range of transition metal ions (Heller & Schubert, 2003). This property has been widely used in analytical chemistry (Schubert & Eschbaumer, 2002), photochemistry for the design of luminescent devices (Harriman & Ziessel, 1998) and biochemistry (Trawick et al., 1998). Although the number of publications or investigations of terpyridine complexes has increased enormously, comparably few preparations of functionalized terpyridine derivatives have been reported as yet. 4-(4-Imidazole-1-yl-phenyl)-[2,2':6',2"] terpyridine is a novel compound containing terpyridine and imidazole coordination sites. We report here the synthesis, characterization and crystal structure of the title compound, IPTP or (I).

The molecular structure of the title compound was determined by single-crystal X-ray diffraction and shown in Fig. 1. The packing diagram is shown in Fig. 2. Bond lengths and angles in the compound are given in Table 1. The three pyridyl rings are almost co-planar, with interplanar angles of 7.1 (su?), 171 (su?) and 168.3 (su?)°, respectively. The benzene ring forms dihedral angles of 49.6 (su?) and 19.2 (su?)° with the medial pyridyl ring and imidazole ring.

Experimental top

For the preparation of 3-(4-imidazole-1-yl-phenyl)-1-(pyridin-2-yl)-prop-2-en-1-one, a flask charged with a mixture of 4-imidazole-1-benzaldehyde (8.6 g, 50 mmol), 2-acetylpyridine (6.1 g, 50 mmol) and 2% aqueous sodium hydroxide (150 ml) was stirred vigorously at room temperature for 30 min, and was then heated to about 333 K for 6 h. The reaction was monitored by TLC. After the reaction was complete, the reaction mixture was cooled to room temperature. A light-yellow solid was precipitated which was then filtered, washed thoroughly with water and air-dried to give 13.6 g of 3-(4-imidazole-1-yl-phenyl)-1-(pyridin-2-yl)-prop-2-en-1-one (yield: 98.0%).

For the preparation of IPTP, 2-acetylpyridine (1.8 g, 15 mmol) and 3-(4-imidazole-1-yl-phenyl)-1- (pyridin-2-yl)-prop-2-en-1-one (4.1 g, 15 mmol) and NaOH (2.4 g, 60 mmol) powder were crushed together with a pestle and mortar for 2 h. The yellow powder was added to a stirred solution of ammonium acetate (10 g, excess) in ethanol (100 ml). The reaction mixture was heated at reflux for 10 h. Upon cooling to room temperature, the precipitate was filtered, washed with water three times and dried to afford the product. Recrystallization from ethanol afforded white needle crystals. ¹H NMR (CDCl₃): δ 7.27 (t, 1H), 7.37 (m, 3H), 7.55 (d, 2H), 7.90 (m, 2H), 7.98 (s, 1H), 8.04 (d, 2H), 8.67 (s, 1H), 8.70 (s, 1H), 8.74 (m, 2H), 8.76 (s, 2H). ¹³C NMR (CDCl₃): δ 117.7, 118.2, 120.9, 121.2, 123.5, 128.5, 129.9, 134.9, 136.3, 136.5, 148.5, 148.7, 155.3, 155.5, 155.7.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of IPTP showing 50% probability displacement ellipsoids.
	Fig. 2. The packing diagram of IPTP. Hydrogen bonds are shown as dashed lines.

4'-[4-(Imidazol-1-yl)phenyl]-2,2':6',2''-terpyridine top

Crystal data top

C₂₄H₁₇N₅	F(000) = 784
M_r = 375.43	D_x = 1.352 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 41 reflections
a = 5.4807 (5) Å	θ = 5.2–12.5°
b = 38.653 (5) Å	µ = 0.08 mm⁻¹
c = 8.953 (1) Å	T = 293 K
β = 103.470 (9)°	Plate, pale yellow
V = 1844.5 (4) Å³	0.45 × 0.34 × 0.10 mm
Z = 4

Data collection top

Bruker P4 diffractometer	1574 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.035
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
ω scans	h = −6→1
Absorption correction: ψ scan (North et al., 1968)	k = −1→47
T_min = 0.918, T_max = 0.992	l = −11→11
4935 measured reflections	3 standard reflections every 97 reflections
3625 independent reflections	intensity decay: none

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.051	H-atom parameters constrained
wR(F²) = 0.156	w = 1/[σ²(F_o²) + (0.0662P)²] where P = (F_o² + 2F_c²)/3
S = 0.93	(Δ/σ)_max < 0.001
3625 reflections	Δρ_max = 0.19 e Å⁻³
263 parameters	Δρ_min = −0.18 e Å⁻³
0 restraints	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.025 (2)

Crystal data top

C₂₄H₁₇N₅	V = 1844.5 (4) Å³
M_r = 375.43	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 5.4807 (5) Å	µ = 0.08 mm⁻¹
b = 38.653 (5) Å	T = 293 K
c = 8.953 (1) Å	0.45 × 0.34 × 0.10 mm
β = 103.470 (9)°

Data collection top

Bruker P4 diffractometer	1574 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.035
T_min = 0.918, T_max = 0.992	3 standard reflections every 97 reflections
4935 measured reflections	intensity decay: none
3625 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.051	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 0.93	Δρ_max = 0.19 e Å⁻³
3625 reflections	Δρ_min = −0.18 e Å⁻³
263 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 > 2σ(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	−0.4512 (7)	−0.04771 (9)	0.2268 (3)	0.0733 (10)
H1A	−0.4764	−0.0707	0.1969	0.088*
C2	−0.2582 (7)	−0.02841 (9)	0.2078 (4)	0.0804 (11)
H2A	−0.1282	−0.0354	0.1640	0.096*
C3	−0.4990 (6)	0.00118 (9)	0.3178 (4)	0.0744 (10)
H3A	−0.5633	0.0193	0.3654	0.089*
C4	−0.1317 (5)	0.03304 (7)	0.2661 (3)	0.0499 (7)
C5	−0.0669 (6)	0.04179 (7)	0.1325 (3)	0.0613 (8)
H5A	−0.1328	0.0295	0.0428	0.074*
C6	0.0977 (6)	0.06907 (7)	0.1314 (3)	0.0605 (8)
H6A	0.1413	0.0748	0.0401	0.073*
C7	0.1989 (5)	0.08803 (7)	0.2626 (3)	0.0482 (7)
C8	0.1219 (6)	0.07932 (7)	0.3943 (3)	0.0591 (8)
H8A	0.1809	0.0921	0.4834	0.071*
C9	−0.0417 (6)	0.05193 (7)	0.3969 (3)	0.0584 (8)
H9A	−0.0897	0.0465	0.4871	0.070*
C10	0.3796 (5)	0.11633 (6)	0.2575 (3)	0.0468 (7)
C11	0.5083 (5)	0.11794 (7)	0.1412 (3)	0.0528 (7)
H11A	0.4864	0.1006	0.0674	0.063*
C12	0.6693 (5)	0.14529 (7)	0.1343 (3)	0.0499 (7)
C13	0.7993 (5)	0.14817 (7)	0.0071 (3)	0.0517 (7)
C14	0.9829 (6)	0.17280 (8)	0.0081 (3)	0.0639 (8)
H14A	1.0220	0.1888	0.0876	0.077*
C15	1.1069 (6)	0.17355 (9)	−0.1083 (4)	0.0754 (10)
H15A	1.2316	0.1899	−0.1079	0.090*
C16	1.0451 (7)	0.15002 (10)	−0.2246 (4)	0.0747 (10)
H16A	1.1280	0.1497	−0.3042	0.090*
C17	0.8564 (7)	0.12678 (9)	−0.2208 (4)	0.0780 (10)
H17A	0.8114	0.1111	−0.3012	0.094*
C18	0.4279 (5)	0.14264 (7)	0.3670 (3)	0.0519 (7)
H18A	0.3462	0.1428	0.4471	0.062*
C19	0.5981 (5)	0.16861 (6)	0.3561 (3)	0.0475 (7)
C20	0.6595 (5)	0.19635 (6)	0.4745 (3)	0.0463 (7)
C21	0.8600 (6)	0.21828 (7)	0.4796 (3)	0.0570 (8)
H21A	0.9587	0.2160	0.4086	0.068*
C22	0.9126 (6)	0.24360 (7)	0.5913 (4)	0.0637 (8)
H22A	1.0456	0.2588	0.5957	0.076*
C23	0.7665 (6)	0.24595 (8)	0.6951 (4)	0.0641 (8)
H23A	0.7980	0.2625	0.7726	0.077*
C24	0.5715 (6)	0.22305 (8)	0.6814 (4)	0.0674 (9)
H24A	0.4714	0.2249	0.7519	0.081*
N1	−0.6040 (5)	−0.02951 (7)	0.2949 (3)	0.0787 (9)
N2	−0.2893 (4)	0.00369 (6)	0.2655 (3)	0.0545 (6)
N3	0.7155 (4)	0.17048 (5)	0.2408 (2)	0.0508 (6)
N4	0.5142 (5)	0.19843 (6)	0.5750 (3)	0.0593 (7)
N5	0.7345 (5)	0.12550 (6)	−0.1082 (3)	0.0659 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.080 (2)	0.071 (2)	0.072 (2)	−0.024 (2)	0.0217 (19)	−0.0142 (17)
C2	0.093 (3)	0.070 (2)	0.093 (2)	−0.030 (2)	0.051 (2)	−0.0287 (19)
C3	0.066 (2)	0.065 (2)	0.102 (3)	0.0005 (19)	0.040 (2)	0.0008 (19)
C4	0.0511 (18)	0.0487 (16)	0.0517 (16)	−0.0092 (14)	0.0154 (14)	−0.0025 (13)
C5	0.071 (2)	0.0618 (19)	0.0518 (17)	−0.0178 (17)	0.0145 (16)	−0.0059 (15)
C6	0.072 (2)	0.0613 (18)	0.0507 (17)	−0.0102 (17)	0.0201 (16)	0.0041 (14)
C7	0.0536 (17)	0.0434 (15)	0.0487 (15)	−0.0021 (14)	0.0140 (14)	0.0004 (13)
C8	0.070 (2)	0.0538 (17)	0.0575 (17)	−0.0168 (16)	0.0222 (16)	−0.0091 (14)
C9	0.069 (2)	0.0574 (17)	0.0548 (17)	−0.0132 (17)	0.0257 (16)	−0.0057 (14)
C10	0.0520 (18)	0.0400 (14)	0.0490 (15)	0.0001 (13)	0.0132 (14)	0.0047 (12)
C11	0.0589 (19)	0.0441 (15)	0.0578 (17)	−0.0037 (15)	0.0186 (15)	−0.0014 (13)
C12	0.0527 (18)	0.0448 (15)	0.0544 (16)	0.0037 (14)	0.0169 (14)	0.0043 (13)
C13	0.0541 (18)	0.0457 (16)	0.0581 (17)	0.0031 (15)	0.0186 (15)	0.0062 (14)
C14	0.067 (2)	0.0626 (19)	0.0672 (19)	−0.0034 (18)	0.0263 (17)	0.0092 (16)
C15	0.069 (2)	0.083 (2)	0.083 (2)	−0.008 (2)	0.034 (2)	0.016 (2)
C16	0.078 (2)	0.088 (2)	0.068 (2)	0.013 (2)	0.037 (2)	0.022 (2)
C17	0.095 (3)	0.079 (2)	0.070 (2)	0.002 (2)	0.039 (2)	0.0034 (18)
C18	0.0560 (18)	0.0473 (15)	0.0556 (16)	−0.0013 (15)	0.0196 (15)	0.0024 (13)
C19	0.0502 (17)	0.0400 (14)	0.0539 (16)	0.0007 (14)	0.0155 (14)	0.0020 (13)
C20	0.0441 (16)	0.0408 (14)	0.0536 (16)	0.0020 (13)	0.0103 (14)	0.0044 (13)
C21	0.0561 (19)	0.0532 (17)	0.0654 (19)	−0.0051 (15)	0.0218 (16)	0.0035 (15)
C22	0.062 (2)	0.0505 (17)	0.078 (2)	−0.0080 (16)	0.0142 (18)	−0.0019 (16)
C23	0.062 (2)	0.0540 (18)	0.075 (2)	−0.0015 (17)	0.0126 (18)	−0.0120 (16)
C24	0.064 (2)	0.0657 (19)	0.078 (2)	−0.0029 (18)	0.0260 (18)	−0.0155 (17)
N1	0.0642 (19)	0.0696 (18)	0.107 (2)	−0.0169 (16)	0.0293 (17)	0.0019 (17)
N2	0.0526 (15)	0.0550 (15)	0.0579 (14)	−0.0115 (13)	0.0173 (12)	−0.0058 (12)
N3	0.0514 (14)	0.0448 (13)	0.0584 (14)	0.0010 (12)	0.0175 (12)	0.0017 (11)
N4	0.0579 (16)	0.0551 (15)	0.0701 (16)	−0.0050 (13)	0.0252 (14)	−0.0100 (13)
N5	0.082 (2)	0.0620 (16)	0.0618 (15)	−0.0047 (15)	0.0334 (15)	−0.0008 (13)

Geometric parameters (Å, º) top

C1—C2	1.338 (4)	C12—C13	1.482 (4)
C1—N1	1.343 (4)	C13—N5	1.338 (3)
C1—H1A	0.9300	C13—C14	1.384 (4)
C2—N2	1.370 (4)	C14—C15	1.370 (4)
C2—H2A	0.9300	C14—H14A	0.9300
C3—N1	1.314 (4)	C15—C16	1.365 (4)
C3—N2	1.342 (3)	C15—H15A	0.9300
C3—H3A	0.9300	C16—C17	1.376 (4)
C4—C5	1.367 (3)	C16—H16A	0.9300
C4—C9	1.371 (3)	C17—N5	1.333 (3)
C4—N2	1.425 (3)	C17—H17A	0.9300
C5—C6	1.389 (4)	C18—C19	1.389 (3)
C5—H5A	0.9300	C18—H18A	0.9300
C6—C7	1.386 (4)	C19—N3	1.339 (3)
C6—H6A	0.9300	C19—C20	1.490 (3)
C7—C8	1.384 (3)	C20—N4	1.336 (3)
C7—C10	1.484 (4)	C20—C21	1.380 (4)
C8—C9	1.391 (4)	C21—C22	1.381 (4)
C8—H8A	0.9300	C21—H21A	0.9300
C9—H9A	0.9300	C22—C23	1.364 (4)
C10—C11	1.388 (3)	C22—H22A	0.9300
C10—C18	1.394 (3)	C23—C24	1.371 (4)
C11—C12	1.388 (4)	C23—H23A	0.9300
C11—H11A	0.9300	C24—N4	1.331 (3)
C12—N3	1.345 (3)	C24—H24A	0.9300

C2—C1—N1	111.1 (3)	C15—C14—H14A	120.1
C2—C1—H1A	124.4	C13—C14—H14A	120.1
N1—C1—H1A	124.4	C16—C15—C14	119.2 (3)
C1—C2—N2	106.6 (3)	C16—C15—H15A	120.4
C1—C2—H2A	126.7	C14—C15—H15A	120.4
N2—C2—H2A	126.7	C15—C16—C17	118.0 (3)
N1—C3—N2	113.0 (3)	C15—C16—H16A	121.0
N1—C3—H3A	123.5	C17—C16—H16A	121.0
N2—C3—H3A	123.5	N5—C17—C16	123.7 (3)
C5—C4—C9	120.0 (3)	N5—C17—H17A	118.1
C5—C4—N2	118.3 (2)	C16—C17—H17A	118.1
C9—C4—N2	121.7 (2)	C19—C18—C10	119.9 (3)
C4—C5—C6	119.7 (3)	C19—C18—H18A	120.1
C4—C5—H5A	120.2	C10—C18—H18A	120.1
C6—C5—H5A	120.2	N3—C19—C18	122.9 (2)
C7—C6—C5	121.8 (3)	N3—C19—C20	116.1 (2)
C7—C6—H6A	119.1	C18—C19—C20	120.9 (2)
C5—C6—H6A	119.1	N4—C20—C21	122.4 (3)
C8—C7—C6	116.9 (3)	N4—C20—C19	116.8 (2)
C8—C7—C10	123.0 (2)	C21—C20—C19	120.8 (3)
C6—C7—C10	120.1 (2)	C20—C21—C22	119.3 (3)
C7—C8—C9	121.7 (3)	C20—C21—H21A	120.3
C7—C8—H8A	119.1	C22—C21—H21A	120.3
C9—C8—H8A	119.1	C23—C22—C21	118.9 (3)
C4—C9—C8	119.8 (3)	C23—C22—H22A	120.5
C4—C9—H9A	120.1	C21—C22—H22A	120.5
C8—C9—H9A	120.1	C22—C23—C24	117.7 (3)
C11—C10—C18	116.6 (3)	C22—C23—H23A	121.1
C11—C10—C7	121.0 (2)	C24—C23—H23A	121.1
C18—C10—C7	122.3 (2)	N4—C24—C23	125.1 (3)
C12—C11—C10	120.5 (3)	N4—C24—H24A	117.5
C12—C11—H11A	119.8	C23—C24—H24A	117.5
C10—C11—H11A	119.8	C3—N1—C1	104.3 (3)
N3—C12—C11	122.5 (2)	C3—N2—C2	104.9 (3)
N3—C12—C13	116.5 (2)	C3—N2—C4	128.6 (3)
C11—C12—C13	121.1 (3)	C2—N2—C4	126.4 (2)
N5—C13—C14	121.2 (3)	C19—N3—C12	117.5 (2)
N5—C13—C12	117.1 (3)	C24—N4—C20	116.5 (3)
C14—C13—C12	121.7 (3)	C17—N5—C13	118.0 (3)
C15—C14—C13	119.9 (3)

N1—C1—C2—N2	−0.4 (4)	C10—C18—C19—C20	−177.9 (2)
C9—C4—C5—C6	2.4 (4)	N3—C19—C20—N4	168.8 (2)
N2—C4—C5—C6	−176.4 (3)	C18—C19—C20—N4	−11.1 (4)
C4—C5—C6—C7	−0.3 (4)	N3—C19—C20—C21	−12.1 (4)
C5—C6—C7—C8	−2.1 (4)	C18—C19—C20—C21	168.1 (2)
C5—C6—C7—C10	178.3 (3)	N4—C20—C21—C22	−0.6 (4)
C6—C7—C8—C9	2.5 (4)	C19—C20—C21—C22	−179.7 (2)
C10—C7—C8—C9	−177.9 (3)	C20—C21—C22—C23	0.9 (4)
C5—C4—C9—C8	−2.0 (4)	C21—C22—C23—C24	−0.8 (5)
N2—C4—C9—C8	176.8 (3)	C22—C23—C24—N4	0.5 (5)
C7—C8—C9—C4	−0.5 (5)	N2—C3—N1—C1	1.1 (4)
C8—C7—C10—C11	160.8 (3)	C2—C1—N1—C3	−0.4 (4)
C6—C7—C10—C11	−19.7 (4)	N1—C3—N2—C2	−1.3 (4)
C8—C7—C10—C18	−19.7 (4)	N1—C3—N2—C4	177.9 (3)
C6—C7—C10—C18	159.8 (3)	C1—C2—N2—C3	1.0 (4)
C18—C10—C11—C12	−2.1 (4)	C1—C2—N2—C4	−178.3 (3)
C7—C10—C11—C12	177.5 (2)	C5—C4—N2—C3	−130.4 (3)
C10—C11—C12—N3	2.5 (4)	C9—C4—N2—C3	50.8 (4)
C10—C11—C12—C13	−177.3 (2)	C5—C4—N2—C2	48.7 (4)
N3—C12—C13—N5	−172.9 (2)	C9—C4—N2—C2	−130.1 (3)
C11—C12—C13—N5	6.9 (4)	C18—C19—N3—C12	−2.0 (4)
N3—C12—C13—C14	8.2 (4)	C20—C19—N3—C12	178.2 (2)
C11—C12—C13—C14	−172.0 (3)	C11—C12—N3—C19	−0.4 (4)
N5—C13—C14—C15	−2.0 (4)	C13—C12—N3—C19	179.3 (2)
C12—C13—C14—C15	176.9 (3)	C23—C24—N4—C20	−0.2 (5)
C13—C14—C15—C16	0.6 (5)	C21—C20—N4—C24	0.3 (4)
C14—C15—C16—C17	1.0 (5)	C19—C20—N4—C24	179.4 (2)
C15—C16—C17—N5	−1.5 (5)	C16—C17—N5—C13	0.1 (5)
C11—C10—C18—C19	−0.2 (4)	C14—C13—N5—C17	1.6 (4)
C7—C10—C18—C19	−179.7 (2)	C12—C13—N5—C17	−177.4 (3)
C10—C18—C19—N3	2.3 (4)

Experimental details

Crystal data
Chemical formula	C₂₄H₁₇N₅
M_r	375.43
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	5.4807 (5), 38.653 (5), 8.953 (1)
β (°)	103.470 (9)
V (Å³)	1844.5 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.45 × 0.34 × 0.10

Data collection
Diffractometer	Bruker P4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.918, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections	4935, 3625, 1574
R_int	0.035
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.156, 0.93
No. of reflections	3625
No. of parameters	263
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.19, −0.18

Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXTL (Bruker, 1997), SHELXTL.

Selected geometric parameters (Å, º) top

C1—N1	1.343 (4)	C12—N3	1.345 (3)
C2—N2	1.370 (4)	C13—N5	1.338 (3)
C3—N1	1.314 (4)	C17—N5	1.333 (3)
C3—N2	1.342 (3)	C19—N3	1.339 (3)
C4—N2	1.425 (3)	C20—N4	1.336 (3)
C7—C10	1.484 (4)	C24—N4	1.331 (3)

C3—N1—C1	104.3 (3)	C19—N3—C12	117.5 (2)
C3—N2—C2	104.9 (3)	C24—N4—C20	116.5 (3)
C3—N2—C4	128.6 (3)	C17—N5—C13	118.0 (3)
C2—N2—C4	126.4 (2)

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