4′-[4-(Pyridin-2-yl)phen­yl]-2,2′:6′,2′′-terpyridine

Zhu, C.-Y.

doi:10.1107/S1600536810039413

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2756

https://doi.org/10.1107/S1600536810039413

Open

access

4′-[4-(Pyridin-2-yl)phenyl]-2,2′:6′,2′′-terpyridine

Chao-Yun Zhu ^a ^*

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: zhuchaoyun120@163.com

(Received 17 September 2010; accepted 1 October 2010; online 9 October 2010)

In the title compound, C₂₆H₁₈N₄, each ring is almost planar with maximum deviation of 0.012 (5) Å. In the crystal, molecules are stacked by weak C—H⋯π interactions, forming a three-dimensional framework.

Related literature

For the uses and the synthesis of the title compound, see: Arm et al. (2006 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₆H₁₈N₄
M_r = 386.44
Monoclinic, P 2₁ /c
a = 11.056 (2) Å
b = 16.113 (3) Å
c = 11.748 (2) Å
β = 109.05 (3)°
V = 1978.2 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 298 K
0.30 × 0.20 × 0.05 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.977, T_max = 0.996
3778 measured reflections
3585 independent reflections
1576 reflections with I > 2σ(I)
R_int = 0.100
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.217
S = 0.88
3585 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the N2/C12–C16 and N3/C17–C21 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯Cg1ⁱ	0.93	2.97	3.675 (5)	134
C25—H25A⋯Cg2ⁱⁱ	0.93	3.19	3.989 (5)	146
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: CAD-4 Software (Enraf–Nonius, 1985 ); cell refinement: CAD-4 Software; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, Is1. DOI: https://doi.org/10.1107/S1600536810039413/bq2233sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810039413/bq2233Isup2.hkl

checkCIF report

Comment top

4'-(4-(Pyridin-2-yl)phenyl)-2,2':6',2''-terpyridine, (I), is an important intermediate used to synthesize luminescent transition metal complexes, which are potentially interesting components of new molecular sensors for detection of molecules or ions in aqueous solution (Arm et al., 2006). We report here the crystal structure of the title compound (Fig. 1).

Bond lengths (Allen et al., 1987) and angles of (I) are within normal ranges. In (I), each ring is planar with the max. deviation 0.012 (5) Å. The dihedral angles of the rings A (C1—C5/N1), B(C6—C11), C(C12—C16/N2), D(C17—C21/N3), E(C22—C26/N4) are: A/B = 159.6 (2)°, C/B = 158.5 (2)°, D/A = 4.8 (1)°, E/A = 170.6 (3)°.

In the crystal structure, no obvious hydrogen bond was observed, and molecules were stacked to form a three-dimensional framework by two C—H···π weak interactions, which may be effective for the stabilization of the crystal (Table 1, Fig 2).

Related literature top

For the uses and the synthesis of the title compound, see: Arm et al. (2006). For bond-length data, see: Allen et al. (1987).

Experimental top

The title compound (I) was prepared by the method reported in literature (Arm et al., 2006). Single crystals were obtained by dissolving the title compound (0.5 g, 1.3 mmol) in ethanol (100 ml) and evaporating the solvent slowly at room temperature for about 20 d.

Structure description top

For the uses and the synthesis of the title compound, see: Arm et al. (2006). For bond-length data, see: Allen et al. (1987).

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1985); cell refinement: CAD-4 Software (Enraf–Nonius, 1985); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of the title compound, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Crystal packing of the title compound.

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

Crystal data top

C₂₆H₁₈N₄	F(000) = 808
M_r = 386.44	D_x = 1.298 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 25 reflections
a = 11.056 (2) Å	θ = 9–12°
b = 16.113 (3) Å	µ = 0.08 mm⁻¹
c = 11.748 (2) Å	T = 298 K
β = 109.05 (3)°	Block, colorless
V = 1978.2 (7) Å³	0.30 × 0.20 × 0.05 mm
Z = 4

Data collection top

Enraf–Nonius CAD-4 diffractometer	1576 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.100
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = 0→13
Absorption correction: ψ scan (North et al., 1968)	k = 0→19
T_min = 0.977, T_max = 0.996	l = −14→13
3778 measured reflections	3 standard reflections every 200 reflections
3585 independent reflections	intensity decay: 1%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.217	H-atom parameters constrained
S = 0.88	w = 1/[σ²(F_o²) + (0.1P)²] where P = (F_o² + 2F_c²)/3
3585 reflections	(Δ/σ)_max < 0.001
271 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₆H₁₈N₄	V = 1978.2 (7) Å³
M_r = 386.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.056 (2) Å	µ = 0.08 mm⁻¹
b = 16.113 (3) Å	T = 298 K
c = 11.748 (2) Å	0.30 × 0.20 × 0.05 mm
β = 109.05 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1576 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.100
T_min = 0.977, T_max = 0.996	3 standard reflections every 200 reflections
3778 measured reflections	intensity decay: 1%
3585 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.217	H-atom parameters constrained
S = 0.88	Δρ_max = 0.16 e Å⁻³
3585 reflections	Δρ_min = −0.16 e Å⁻³
271 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
N1	0.0183 (4)	0.5691 (3)	−0.2077 (3)	0.0771 (12)
C1	0.1554 (4)	0.6611 (3)	−0.2631 (4)	0.0634 (12)
H1B	0.2255	0.6967	−0.2401	0.076*
N2	0.5599 (3)	0.65373 (19)	0.5784 (3)	0.0471 (8)
C2	0.0865 (5)	0.6503 (3)	−0.3842 (4)	0.0801 (15)
H2B	0.1114	0.6769	−0.4433	0.096*
N3	0.7514 (3)	0.7844 (2)	0.4578 (3)	0.0615 (10)
C3	−0.0173 (5)	0.6003 (4)	−0.4147 (4)	0.0881 (16)
H3B	−0.0671	0.5933	−0.4949	0.106*
N4	0.3280 (3)	0.5058 (2)	0.6038 (3)	0.0554 (9)
C4	−0.0471 (5)	0.5607 (4)	−0.3254 (4)	0.102 (2)
H4B	−0.1175	0.5254	−0.3472	0.122*
C5	0.1198 (4)	0.6189 (3)	−0.1773 (3)	0.0527 (11)
C6	0.1957 (4)	0.6248 (2)	−0.0466 (3)	0.0482 (10)
C7	0.2778 (4)	0.6900 (3)	−0.0008 (3)	0.0631 (12)
H7A	0.2854	0.7321	−0.0521	0.076*
C8	0.3490 (4)	0.6939 (3)	0.1201 (3)	0.0627 (12)
H8A	0.4035	0.7388	0.1479	0.075*
C9	0.3417 (4)	0.6330 (2)	0.2014 (3)	0.0458 (10)
C10	0.2592 (4)	0.5674 (2)	0.1543 (3)	0.0516 (10)
H10A	0.2524	0.5247	0.2051	0.062*
C11	0.1874 (4)	0.5641 (2)	0.0346 (3)	0.0540 (11)
H11A	0.1316	0.5198	0.0069	0.065*
C12	0.4183 (4)	0.6392 (2)	0.3317 (3)	0.0451 (10)
C13	0.5279 (4)	0.6881 (2)	0.3720 (3)	0.0504 (10)
H13A	0.5561	0.7165	0.3165	0.060*
C14	0.5960 (4)	0.6950 (2)	0.4949 (3)	0.0464 (10)
C15	0.4563 (4)	0.6052 (2)	0.5413 (3)	0.0433 (9)
C16	0.3837 (4)	0.5966 (2)	0.4191 (3)	0.0483 (10)
H16A	0.3121	0.5623	0.3967	0.058*
C17	0.7120 (4)	0.7465 (2)	0.5409 (3)	0.0459 (9)
C18	0.8562 (4)	0.8311 (3)	0.4969 (4)	0.0724 (14)
H18A	0.8851	0.8572	0.4399	0.087*
C19	0.9243 (4)	0.8431 (3)	0.6170 (4)	0.0694 (13)
H19A	0.9967	0.8767	0.6403	0.083*
C20	0.8825 (4)	0.8045 (3)	0.7007 (4)	0.0650 (12)
H20A	0.9264	0.8113	0.7824	0.078*
C21	0.7747 (4)	0.7551 (3)	0.6631 (3)	0.0571 (11)
H21A	0.7448	0.7283	0.7188	0.069*
C22	0.4209 (4)	0.5621 (2)	0.6383 (3)	0.0459 (10)
C23	0.4842 (4)	0.5816 (3)	0.7587 (3)	0.0534 (11)
H23A	0.5490	0.6212	0.7796	0.064*
C24	0.4488 (4)	0.5412 (3)	0.8459 (3)	0.0636 (12)
H24A	0.4879	0.5543	0.9267	0.076*
C25	0.3555 (4)	0.4814 (3)	0.8129 (3)	0.0638 (12)
H25A	0.3315	0.4522	0.8704	0.077*
C26	0.2982 (4)	0.4660 (3)	0.6910 (4)	0.0626 (12)
H26A	0.2351	0.4254	0.6685	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.071 (3)	0.105 (3)	0.053 (2)	−0.025 (2)	0.017 (2)	−0.008 (2)
C1	0.070 (3)	0.073 (3)	0.044 (2)	−0.002 (3)	0.014 (2)	0.000 (2)
N2	0.056 (2)	0.050 (2)	0.0383 (17)	−0.0039 (17)	0.0195 (16)	−0.0027 (15)
C2	0.094 (4)	0.102 (4)	0.044 (3)	0.004 (3)	0.021 (3)	0.009 (3)
N3	0.065 (2)	0.075 (3)	0.048 (2)	−0.011 (2)	0.0235 (19)	0.0061 (18)
C3	0.093 (4)	0.115 (5)	0.047 (3)	−0.009 (4)	0.010 (3)	−0.008 (3)
N4	0.066 (2)	0.065 (2)	0.0406 (19)	−0.010 (2)	0.0247 (17)	0.0004 (17)
C4	0.091 (4)	0.144 (6)	0.062 (3)	−0.045 (4)	0.013 (3)	−0.020 (3)
C5	0.055 (3)	0.065 (3)	0.040 (2)	0.003 (2)	0.018 (2)	−0.003 (2)
C6	0.053 (2)	0.054 (3)	0.041 (2)	0.002 (2)	0.0200 (19)	0.0002 (19)
C7	0.082 (3)	0.068 (3)	0.037 (2)	−0.020 (3)	0.016 (2)	0.006 (2)
C8	0.088 (3)	0.057 (3)	0.042 (2)	−0.024 (3)	0.020 (2)	0.000 (2)
C9	0.050 (2)	0.051 (2)	0.039 (2)	0.003 (2)	0.0194 (19)	−0.0030 (19)
C10	0.061 (3)	0.055 (3)	0.039 (2)	−0.010 (2)	0.017 (2)	0.0022 (19)
C11	0.059 (3)	0.058 (3)	0.050 (2)	−0.011 (2)	0.025 (2)	−0.003 (2)
C12	0.057 (3)	0.049 (2)	0.034 (2)	0.006 (2)	0.0220 (19)	0.0035 (18)
C13	0.057 (3)	0.051 (2)	0.047 (2)	0.001 (2)	0.023 (2)	0.0008 (19)
C14	0.058 (2)	0.046 (2)	0.041 (2)	0.002 (2)	0.0233 (19)	0.0005 (18)
C15	0.051 (2)	0.044 (2)	0.039 (2)	0.003 (2)	0.0202 (19)	−0.0022 (17)
C16	0.058 (3)	0.053 (2)	0.037 (2)	−0.005 (2)	0.0208 (19)	−0.0054 (18)
C17	0.056 (2)	0.047 (2)	0.037 (2)	0.001 (2)	0.0191 (18)	−0.0026 (18)
C18	0.078 (3)	0.084 (4)	0.059 (3)	−0.021 (3)	0.027 (3)	0.003 (3)
C19	0.069 (3)	0.072 (3)	0.071 (3)	−0.014 (3)	0.027 (3)	−0.002 (3)
C20	0.067 (3)	0.074 (3)	0.049 (3)	−0.008 (3)	0.014 (2)	−0.013 (2)
C21	0.063 (3)	0.070 (3)	0.040 (2)	−0.007 (2)	0.020 (2)	−0.003 (2)
C22	0.058 (3)	0.041 (2)	0.044 (2)	0.006 (2)	0.023 (2)	0.0038 (18)
C23	0.062 (3)	0.057 (3)	0.041 (2)	−0.002 (2)	0.017 (2)	0.0040 (19)
C24	0.079 (3)	0.075 (3)	0.033 (2)	−0.001 (3)	0.014 (2)	0.013 (2)
C25	0.076 (3)	0.076 (3)	0.044 (3)	−0.002 (3)	0.025 (2)	0.017 (2)
C26	0.067 (3)	0.072 (3)	0.050 (3)	−0.015 (2)	0.021 (2)	0.008 (2)

Geometric parameters (Å, º) top

N1—C5	1.330 (5)	C10—H10A	0.9300
N1—C4	1.342 (5)	C11—H11A	0.9300
C1—C5	1.376 (5)	C12—C16	1.389 (5)
C1—C2	1.388 (5)	C12—C13	1.392 (5)
C1—H1B	0.9300	C13—C14	1.398 (5)
N2—C15	1.338 (4)	C13—H13A	0.9300
N2—C14	1.348 (4)	C14—C17	1.474 (5)
C2—C3	1.351 (7)	C15—C16	1.404 (5)
C2—H2B	0.9300	C15—C22	1.491 (5)
N3—C18	1.332 (5)	C16—H16A	0.9300
N3—C17	1.339 (4)	C17—C21	1.382 (5)
C3—C4	1.358 (7)	C18—C19	1.379 (5)
C3—H3B	0.9300	C18—H18A	0.9300
N4—C22	1.331 (5)	C19—C20	1.366 (5)
N4—C26	1.339 (4)	C19—H19A	0.9300
C4—H4B	0.9300	C20—C21	1.380 (5)
C5—C6	1.493 (5)	C20—H20A	0.9300
C6—C7	1.378 (5)	C21—H21A	0.9300
C6—C11	1.390 (5)	C22—C23	1.394 (5)
C7—C8	1.382 (5)	C23—C24	1.374 (5)
C7—H7A	0.9300	C23—H23A	0.9300
C8—C9	1.390 (5)	C24—C25	1.372 (6)
C8—H8A	0.9300	C24—H24A	0.9300
C9—C10	1.387 (5)	C25—C26	1.386 (5)
C9—C12	1.492 (5)	C25—H25A	0.9300
C10—C11	1.372 (5)	C26—H26A	0.9300

C5—N1—C4	117.5 (4)	C12—C13—H13A	119.6
C5—C1—C2	119.8 (4)	C14—C13—H13A	119.6
C5—C1—H1B	120.1	N2—C14—C13	121.6 (4)
C2—C1—H1B	120.1	N2—C14—C17	116.1 (3)
C15—N2—C14	118.5 (3)	C13—C14—C17	122.3 (3)
C3—C2—C1	118.8 (5)	N2—C15—C16	122.3 (3)
C3—C2—H2B	120.6	N2—C15—C22	115.7 (3)
C1—C2—H2B	120.6	C16—C15—C22	122.0 (4)
C18—N3—C17	117.4 (4)	C12—C16—C15	120.2 (4)
C2—C3—C4	118.4 (5)	C12—C16—H16A	119.9
C2—C3—H3B	120.8	C15—C16—H16A	119.9
C4—C3—H3B	120.8	N3—C17—C21	122.6 (4)
C22—N4—C26	116.9 (3)	N3—C17—C14	116.2 (3)
N1—C4—C3	124.3 (5)	C21—C17—C14	121.3 (3)
N1—C4—H4B	117.9	N3—C18—C19	123.7 (4)
C3—C4—H4B	117.9	N3—C18—H18A	118.2
N1—C5—C1	121.3 (4)	C19—C18—H18A	118.2
N1—C5—C6	117.1 (4)	C20—C19—C18	118.2 (4)
C1—C5—C6	121.5 (4)	C20—C19—H19A	120.9
C7—C6—C11	116.8 (4)	C18—C19—H19A	120.9
C7—C6—C5	121.9 (4)	C19—C20—C21	119.5 (4)
C11—C6—C5	121.4 (4)	C19—C20—H20A	120.3
C6—C7—C8	121.2 (4)	C21—C20—H20A	120.3
C6—C7—H7A	119.4	C20—C21—C17	118.6 (4)
C8—C7—H7A	119.4	C20—C21—H21A	120.7
C7—C8—C9	122.2 (4)	C17—C21—H21A	120.7
C7—C8—H8A	118.9	N4—C22—C23	123.0 (3)
C9—C8—H8A	118.9	N4—C22—C15	116.9 (3)
C10—C9—C8	116.2 (3)	C23—C22—C15	120.1 (4)
C10—C9—C12	122.6 (3)	C24—C23—C22	118.6 (4)
C8—C9—C12	121.2 (4)	C24—C23—H23A	120.7
C11—C10—C9	121.6 (4)	C22—C23—H23A	120.7
C11—C10—H10A	119.2	C25—C24—C23	119.6 (4)
C9—C10—H10A	119.2	C25—C24—H24A	120.2
C10—C11—C6	122.0 (4)	C23—C24—H24A	120.2
C10—C11—H11A	119.0	C24—C25—C26	117.7 (4)
C6—C11—H11A	119.0	C24—C25—H25A	121.1
C16—C12—C13	116.6 (3)	C26—C25—H25A	121.1
C16—C12—C9	121.7 (4)	N4—C26—C25	124.2 (4)
C13—C12—C9	121.7 (3)	N4—C26—H26A	117.9
C12—C13—C14	120.8 (3)	C25—C26—H26A	117.9

C5—C1—C2—C3	2.2 (7)	C12—C13—C14—C17	−179.8 (3)
C1—C2—C3—C4	−2.1 (8)	C14—N2—C15—C16	−0.6 (5)
C5—N1—C4—C3	−0.8 (8)	C14—N2—C15—C22	−179.3 (3)
C2—C3—C4—N1	1.5 (10)	C13—C12—C16—C15	1.2 (5)
C4—N1—C5—C1	0.8 (7)	C9—C12—C16—C15	−178.6 (3)
C4—N1—C5—C6	−177.2 (4)	N2—C15—C16—C12	0.0 (6)
C2—C1—C5—N1	−1.6 (7)	C22—C15—C16—C12	178.6 (3)
C2—C1—C5—C6	176.3 (4)	C18—N3—C17—C21	0.8 (6)
N1—C5—C6—C7	−161.0 (4)	C18—N3—C17—C14	−179.9 (4)
C1—C5—C6—C7	21.0 (6)	N2—C14—C17—N3	176.9 (3)
N1—C5—C6—C11	19.6 (6)	C13—C14—C17—N3	−2.1 (5)
C1—C5—C6—C11	−158.4 (4)	N2—C14—C17—C21	−3.7 (5)
C11—C6—C7—C8	0.5 (6)	C13—C14—C17—C21	177.2 (4)
C5—C6—C7—C8	−178.9 (4)	C17—N3—C18—C19	−0.8 (7)
C6—C7—C8—C9	−0.1 (7)	N3—C18—C19—C20	0.5 (7)
C7—C8—C9—C10	0.4 (6)	C18—C19—C20—C21	0.0 (7)
C7—C8—C9—C12	−179.2 (4)	C19—C20—C21—C17	0.0 (6)
C8—C9—C10—C11	−1.1 (6)	N3—C17—C21—C20	−0.4 (6)
C12—C9—C10—C11	178.4 (4)	C14—C17—C21—C20	−179.6 (4)
C9—C10—C11—C6	1.7 (6)	C26—N4—C22—C23	−1.4 (6)
C7—C6—C11—C10	−1.3 (6)	C26—N4—C22—C15	178.7 (3)
C5—C6—C11—C10	178.1 (4)	N2—C15—C22—N4	−172.0 (3)
C10—C9—C12—C16	−21.2 (6)	C16—C15—C22—N4	9.3 (5)
C8—C9—C12—C16	158.4 (4)	N2—C15—C22—C23	8.0 (5)
C10—C9—C12—C13	159.0 (4)	C16—C15—C22—C23	−170.6 (3)
C8—C9—C12—C13	−21.4 (6)	N4—C22—C23—C24	−0.3 (6)
C16—C12—C13—C14	−1.8 (5)	C15—C22—C23—C24	179.6 (4)
C9—C12—C13—C14	178.0 (3)	C22—C23—C24—C25	1.9 (6)
C15—N2—C14—C13	0.0 (5)	C23—C24—C25—C26	−1.6 (6)
C15—N2—C14—C17	−179.0 (3)	C22—N4—C26—C25	1.7 (6)
C12—C13—C14—N2	1.3 (6)	C24—C25—C26—N4	−0.2 (7)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N2/C12–C16 and N3/C17–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1ⁱ	0.93	2.97	3.675 (5)	134
C25—H25A···Cg2ⁱⁱ	0.93	3.19	3.989 (5)	146

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₄
M_r	386.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	298
a, b, c (Å)	11.056 (2), 16.113 (3), 11.748 (2)
β (°)	109.05 (3)
V (Å³)	1978.2 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.05

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.977, 0.996
No. of measured, independent and observed [I > 2σ(I)] reflections	3778, 3585, 1576
R_int	0.100
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.217, 0.88
No. of reflections	3585
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.16

Computer programs: CAD-4 Software (Enraf–Nonius, 1985), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the N2/C12–C16 and N3/C17–C21 rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···Cg1ⁱ	0.93	2.9728	3.675 (5)	133.55
C25—H25A···Cg2ⁱⁱ	0.93	3.1870	3.989 (5)	145.56

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

Acknowledgements

The authors thank the Center of Testing and Analysis, Nanjing University, for the data collection.

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. CSD CrossRef Web of Science Google Scholar
Arm, K. J., Leslie, W. & Williams, J. A. G. (2006). Inorg. Chim. Acta, 359, 1222–1232. Web of Science CrossRef CAS Google Scholar
Enraf–Nonius (1985). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2756

https://doi.org/10.1107/S1600536810039413

Open

access