9,9′-Biacridine

Liu, C.-S.

doi:10.1107/S1600536807041463

9,9′-Biacridine

The title molecule, C₂₆H₁₆N₂, is nonplanar, the dihedral angle between the two acridine ring systems being 84.67 (7)°. In the crystal structure, intermolecular C—H

N and C—H

π hydrogen-bonding interactions link the adjacent molecules into a two-dimensional network parallel to the ab plane.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807041463/ci2445sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807041463/ci2445Isup2.hkl Contains datablock I

CCDC reference: 660363

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Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.005 Å
R factor = 0.060
wR factor = 0.113
Data-to-parameter ratio = 12.5

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT026_ALERT_3_C Ratio Observed / Unique Reflections too Low ....         42 Perc.
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

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

   3 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
   2 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

N-containing heterocyclic aromatic compounds are extensively used as bridging ligands in coordination and metallosupramolecular chemistry (Steel, 2005). The most frequently used neutral bridging ligands are 4,4'-bipyridine and its derivatives (Kitagawa et al., 2004). In comparison with other N-containing heterocyclic ligands, acridine-based ligands have some primary structural characteristics: (a) acridine ring has larger conjugated π-systems, therefore π-π stacking interactions may play important roles in the formations of their metal complexes and (b) the larger conjugated π-systems and the steric hindrance of H atoms of the adjacent benzene rings may probably affect the coordination abilities of the acridine N donor atom (Bu et al., 2004; Liu et al., 2006). Recently, we synthesized a 4,4'-bipyridyl-like linear diamine bridging ligand, 9,9'-biacridine, (I). We report here the crystal structure of (I).

Bond distances and angles in (I) (Fig. 1) have normal values, and are comparable to those observed for similar acridine-based molecules (Boyer et al., 1999; Liu et al., 2006). Each of the acridine ring system is essentially planar. The two acridine ring systems are twisted away from one another by an angle of 84.67 (7)°.

In the crystal structure, the adjacent molecules are linked into a chain along the [1 1 0] direction by intermolecular C—H···N hydrogen-bonding interactions (Fig. 2 and Table 1) (Desiraju et al., 1999). The adjacent chains are cross-linked via intermolecular C—H···π interactions (Table 1) involving the N1/C9—C13 pyridine ring (centroid Cg1), forming a two-dimensional network parallel to the ab plane (Fig. 3). In the adjacent chains the acridine rings are arranged in an edge-to-face orientation (Sony et al., 2006).

Related literature top

For related literature, see: Boyer et al. (1999); Bu et al. (2004); Kitagawa et al. (2004); Liu et al. (2006); Steel (2005). For related hydrogen bonds, see: Desiraju & Steiner (1999); Sony & Ponnuswamy (2006).

Experimental top

Compound (I) was synthesized according to the method reported in the literature (Boyer et al., 1999). A solution of (I) (0.1 mmol) in methanol (15 ml) was filtered off and the resulting solution was kept at room temperature. Yellow single crystals suitable for X-ray analysis were obtained by slow evaporation of the solvent after several days (yield: 30%). Analysis calculated for C₂₆H₁₆N₂: C 87.62, H 4.52, N 7.86%; found: C 87.75, H 4.59, N 7.77%.

Structure description top

Computing details top

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT (Bruker, 1998); 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 (Bruker, 1998) and PLATON (Spek, 2003).

Figures top

	Fig. 1. The molecular structure of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. Part of the crystal packing in the title compound, showing a C—H···N hydrogen-bonded (dashed lines) chain. The atoms labelled with the suffixes B and C are generated by the symmetry operations (1/2 - x, 3/2 - y, -z) and (-x, 2 - y, -z), respectively. For clarity, only H atoms involved in the interactions are shown.
	Fig. 3. View of the two-dimensional network formed by intermolecular C—H···π interactions (dashed lines).

9,9'-Biacridine top

Crystal data top

C₂₆H₁₆N₂	F(000) = 1488
M_r = 356.41	D_x = 1.323 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 881 reflections
a = 24.427 (8) Å	θ = 2.3–21.3°
b = 9.463 (3) Å	µ = 0.08 mm⁻¹
c = 15.644 (5) Å	T = 293 K
β = 98.253 (6)°	Block, yellow
V = 3578.9 (19) Å³	0.30 × 0.25 × 0.25 mm
Z = 8

Data collection top

Bruker SMART CCD area-detector diffractometer	3166 independent reflections
Radiation source: fine-focus sealed tube	1342 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.099
φ and ω scans	θ_max = 25.0°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 1998)	h = −28→28
T_min = 0.977, T_max = 0.981	k = −8→11
8953 measured reflections	l = −14→18

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.113	H-atom parameters constrained
S = 0.96	w = 1/[σ²(F_o²) + (0.0303P)²] where P = (F_o² + 2F_c²)/3
3166 reflections	(Δ/σ)_max = 0.002
253 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.17 e Å⁻³

Crystal data top

C₂₆H₁₆N₂	V = 3578.9 (19) Å³
M_r = 356.41	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 24.427 (8) Å	µ = 0.08 mm⁻¹
b = 9.463 (3) Å	T = 293 K
c = 15.644 (5) Å	0.30 × 0.25 × 0.25 mm
β = 98.253 (6)°

Data collection top

Bruker SMART CCD area-detector diffractometer	3166 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 1998)	1342 reflections with I > 2σ(I)
T_min = 0.977, T_max = 0.981	R_int = 0.099
8953 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.060	0 restraints
wR(F²) = 0.113	H-atom parameters constrained
S = 0.96	Δρ_max = 0.16 e Å⁻³
3166 reflections	Δρ_min = −0.17 e Å⁻³
253 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	0.19370 (14)	0.7778 (3)	0.2003 (2)	0.0500 (10)
H1A	0.1676	0.8395	0.2173	0.060*
C2	0.23874 (15)	0.7408 (4)	0.2580 (2)	0.0572 (10)
H2A	0.2432	0.7773	0.3137	0.069*
C3	0.27834 (15)	0.6474 (4)	0.2331 (2)	0.0612 (11)
H3A	0.3093	0.6241	0.2724	0.073*
C4	0.27214 (13)	0.5911 (3)	0.1531 (2)	0.0544 (10)
H4A	0.2984	0.5277	0.1385	0.065*
C5	0.17604 (14)	0.5463 (4)	−0.1308 (2)	0.0545 (10)
H5A	0.2026	0.4810	−0.1420	0.065*
C6	0.13522 (16)	0.5805 (4)	−0.1946 (2)	0.0636 (11)
H6A	0.1339	0.5399	−0.2490	0.076*
C7	0.09413 (14)	0.6788 (4)	−0.1784 (2)	0.0569 (10)
H7A	0.0661	0.7030	−0.2227	0.068*
C8	0.09507 (14)	0.7383 (4)	−0.0992 (2)	0.0489 (9)
H8A	0.0675	0.8017	−0.0894	0.059*
C9	0.14161 (12)	0.7630 (3)	0.0516 (2)	0.0375 (8)
C10	0.18597 (13)	0.7233 (3)	0.1144 (2)	0.0391 (8)
C11	0.22609 (13)	0.6270 (3)	0.0906 (2)	0.0410 (9)
C12	0.17990 (13)	0.6065 (3)	−0.0472 (2)	0.0407 (9)
C13	0.13817 (12)	0.7038 (3)	−0.0310 (2)	0.0388 (8)
C14	0.03651 (14)	0.6738 (4)	0.1059 (2)	0.0566 (10)
H14A	0.0611	0.6050	0.0924	0.068*
C15	−0.01240 (15)	0.6344 (4)	0.1313 (2)	0.0662 (11)
H15A	−0.0209	0.5389	0.1345	0.079*
C16	−0.05029 (15)	0.7365 (5)	0.1529 (2)	0.0647 (11)
H16A	−0.0834	0.7081	0.1702	0.078*
C17	−0.03851 (13)	0.8749 (4)	0.1484 (2)	0.0550 (10)
H17A	−0.0637	0.9413	0.1630	0.066*
C18	0.07636 (15)	1.2536 (4)	0.08545 (19)	0.0542 (10)
H18A	0.0501	1.3163	0.1007	0.065*
C19	0.12268 (15)	1.3040 (4)	0.0582 (2)	0.0610 (10)
H19A	0.1277	1.4011	0.0545	0.073*
C20	0.16333 (14)	1.2119 (4)	0.0353 (2)	0.0532 (10)
H20A	0.1949	1.2487	0.0166	0.064*
C21	0.15701 (12)	1.0701 (3)	0.04014 (18)	0.0429 (9)
H21A	0.1843	1.0102	0.0252	0.052*
C22	0.09950 (12)	0.8657 (3)	0.07359 (18)	0.0377 (8)
C23	0.05018 (12)	0.8194 (4)	0.09971 (18)	0.0403 (8)
C24	0.01180 (13)	0.9217 (4)	0.12164 (19)	0.0415 (8)
C25	0.06751 (13)	1.1060 (3)	0.09096 (18)	0.0397 (8)
C26	0.10848 (12)	1.0121 (3)	0.06823 (17)	0.0365 (8)
N1	0.22283 (10)	0.5684 (3)	0.01215 (18)	0.0449 (8)
N2	0.02041 (10)	1.0618 (3)	0.11775 (15)	0.0447 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.055 (2)	0.038 (2)	0.057 (3)	0.0051 (19)	0.008 (2)	−0.001 (2)
C2	0.067 (3)	0.046 (3)	0.056 (3)	0.004 (2)	0.000 (2)	0.003 (2)
C3	0.057 (3)	0.055 (3)	0.068 (3)	0.010 (2)	−0.005 (2)	0.009 (2)
C4	0.046 (2)	0.042 (2)	0.076 (3)	0.0075 (19)	0.011 (2)	0.011 (2)
C5	0.059 (3)	0.045 (2)	0.063 (3)	0.004 (2)	0.022 (2)	−0.004 (2)
C6	0.077 (3)	0.061 (3)	0.056 (3)	−0.004 (2)	0.018 (2)	−0.010 (2)
C7	0.056 (3)	0.061 (3)	0.052 (2)	−0.004 (2)	0.0015 (19)	−0.001 (2)
C8	0.044 (2)	0.047 (2)	0.056 (2)	0.0013 (18)	0.0086 (19)	0.000 (2)
C9	0.0324 (19)	0.032 (2)	0.050 (2)	−0.0002 (17)	0.0128 (17)	0.0045 (18)
C10	0.038 (2)	0.030 (2)	0.050 (2)	0.0020 (17)	0.0116 (18)	0.0023 (18)
C11	0.0330 (19)	0.030 (2)	0.060 (3)	0.0017 (17)	0.0083 (18)	0.0112 (19)
C12	0.041 (2)	0.035 (2)	0.048 (2)	−0.0007 (18)	0.0153 (18)	0.0001 (18)
C13	0.034 (2)	0.030 (2)	0.055 (2)	−0.0009 (17)	0.0164 (18)	0.0012 (18)
C14	0.055 (2)	0.043 (3)	0.077 (3)	−0.002 (2)	0.025 (2)	0.005 (2)
C15	0.062 (3)	0.052 (3)	0.089 (3)	−0.009 (2)	0.024 (2)	0.006 (2)
C16	0.045 (2)	0.072 (3)	0.081 (3)	−0.003 (2)	0.024 (2)	0.010 (2)
C17	0.040 (2)	0.068 (3)	0.060 (3)	0.008 (2)	0.0170 (18)	0.007 (2)
C18	0.059 (3)	0.042 (3)	0.063 (3)	0.010 (2)	0.017 (2)	0.001 (2)
C19	0.071 (3)	0.037 (2)	0.078 (3)	0.000 (2)	0.020 (2)	0.004 (2)
C20	0.048 (2)	0.047 (3)	0.066 (2)	−0.005 (2)	0.0140 (18)	0.000 (2)
C21	0.041 (2)	0.037 (2)	0.051 (2)	0.0045 (19)	0.0097 (16)	−0.0013 (18)
C22	0.0327 (19)	0.040 (2)	0.041 (2)	0.0063 (18)	0.0058 (16)	−0.0002 (17)
C23	0.036 (2)	0.040 (2)	0.045 (2)	0.0037 (19)	0.0062 (16)	0.0031 (17)
C24	0.034 (2)	0.044 (2)	0.048 (2)	0.0020 (19)	0.0086 (16)	0.0021 (18)
C25	0.040 (2)	0.038 (2)	0.041 (2)	0.0056 (19)	0.0074 (16)	0.0003 (17)
C26	0.0338 (19)	0.037 (2)	0.039 (2)	0.0054 (18)	0.0066 (15)	0.0013 (17)
N1	0.0439 (18)	0.0339 (18)	0.059 (2)	0.0049 (15)	0.0141 (16)	0.0017 (16)
N2	0.0401 (18)	0.043 (2)	0.0533 (19)	0.0086 (16)	0.0131 (14)	0.0037 (15)

Geometric parameters (Å, º) top

C1—C2	1.365 (4)	C14—C15	1.364 (4)
C1—C10	1.427 (4)	C14—C23	1.425 (4)
C1—H1A	0.93	C14—H14A	0.93
C2—C3	1.406 (4)	C15—C16	1.412 (4)
C2—H2A	0.93	C15—H15A	0.93
C3—C4	1.349 (4)	C16—C17	1.345 (4)
C3—H3A	0.93	C16—H16A	0.93
C4—C11	1.421 (4)	C17—C24	1.424 (4)
C4—H4A	0.93	C17—H17A	0.93
C5—C6	1.345 (4)	C18—C19	1.352 (4)
C5—C12	1.418 (4)	C18—C25	1.419 (4)
C5—H5A	0.93	C18—H18A	0.93
C6—C7	1.418 (4)	C19—C20	1.406 (4)
C6—H6A	0.93	C19—H19A	0.93
C7—C8	1.358 (4)	C20—C21	1.354 (4)
C7—H7A	0.93	C20—H20A	0.93
C8—C13	1.425 (4)	C21—C26	1.432 (4)
C8—H8A	0.93	C21—H21A	0.93
C9—C13	1.399 (4)	C22—C23	1.397 (4)
C9—C10	1.405 (4)	C22—C26	1.407 (4)
C9—C22	1.491 (4)	C23—C24	1.423 (4)
C10—C11	1.426 (4)	C24—N2	1.345 (4)
C11—N1	1.339 (4)	C25—N2	1.346 (3)
C12—N1	1.346 (4)	C25—C26	1.421 (4)
C12—C13	1.423 (4)

C2—C1—C10	121.0 (3)	C15—C14—H14A	119.8
C2—C1—H1A	119.5	C23—C14—H14A	119.8
C10—C1—H1A	119.5	C14—C15—C16	120.9 (4)
C1—C2—C3	120.0 (3)	C14—C15—H15A	119.5
C1—C2—H2A	120.0	C16—C15—H15A	119.5
C3—C2—H2A	120.0	C17—C16—C15	120.1 (4)
C4—C3—C2	121.0 (3)	C17—C16—H16A	119.9
C4—C3—H3A	119.5	C15—C16—H16A	119.9
C2—C3—H3A	119.5	C16—C17—C24	121.2 (3)
C3—C4—C11	121.0 (3)	C16—C17—H17A	119.4
C3—C4—H4A	119.5	C24—C17—H17A	119.4
C11—C4—H4A	119.5	C19—C18—C25	120.5 (3)
C6—C5—C12	122.1 (4)	C19—C18—H18A	119.7
C6—C5—H5A	119.0	C25—C18—H18A	119.7
C12—C5—H5A	119.0	C18—C19—C20	121.0 (3)
C5—C6—C7	119.6 (4)	C18—C19—H19A	119.5
C5—C6—H6A	120.2	C20—C19—H19A	119.5
C7—C6—H6A	120.2	C21—C20—C19	120.6 (3)
C8—C7—C6	121.0 (3)	C21—C20—H20A	119.7
C8—C7—H7A	119.5	C19—C20—H20A	119.7
C6—C7—H7A	119.5	C20—C21—C26	120.2 (3)
C7—C8—C13	120.1 (3)	C20—C21—H21A	119.9
C7—C8—H8A	119.9	C26—C21—H21A	119.9
C13—C8—H8A	119.9	C23—C22—C26	118.3 (3)
C13—C9—C10	118.5 (3)	C23—C22—C9	121.0 (3)
C13—C9—C22	121.5 (3)	C26—C22—C9	120.7 (3)
C10—C9—C22	120.1 (3)	C22—C23—C24	118.8 (3)
C9—C10—C11	118.6 (3)	C22—C23—C14	122.9 (3)
C9—C10—C1	123.1 (3)	C24—C23—C14	118.2 (3)
C11—C10—C1	118.3 (3)	N2—C24—C23	123.2 (3)
N1—C11—C4	117.9 (3)	N2—C24—C17	117.8 (3)
N1—C11—C10	123.4 (3)	C23—C24—C17	119.0 (3)
C4—C11—C10	118.7 (3)	N2—C25—C18	118.0 (3)
N1—C12—C5	118.1 (3)	N2—C25—C26	123.2 (3)
N1—C12—C13	123.9 (3)	C18—C25—C26	118.8 (3)
C5—C12—C13	118.1 (3)	C22—C26—C25	118.6 (3)
C9—C13—C12	118.3 (3)	C22—C26—C21	122.6 (3)
C9—C13—C8	122.7 (3)	C25—C26—C21	118.8 (3)
C12—C13—C8	119.1 (3)	C11—N1—C12	117.3 (3)
C15—C14—C23	120.5 (3)	C24—N2—C25	117.8 (3)

C10—C1—C2—C3	−0.1 (5)	C13—C9—C22—C23	84.9 (4)
C1—C2—C3—C4	−1.3 (5)	C10—C9—C22—C23	−95.0 (4)
C2—C3—C4—C11	1.6 (5)	C13—C9—C22—C26	−94.8 (4)
C12—C5—C6—C7	−0.6 (5)	C10—C9—C22—C26	85.2 (4)
C5—C6—C7—C8	−0.5 (5)	C26—C22—C23—C24	−1.4 (4)
C6—C7—C8—C13	0.8 (5)	C9—C22—C23—C24	178.8 (3)
C13—C9—C10—C11	1.3 (4)	C26—C22—C23—C14	178.9 (3)
C22—C9—C10—C11	−178.8 (3)	C9—C22—C23—C14	−0.9 (4)
C13—C9—C10—C1	179.5 (3)	C15—C14—C23—C22	−179.7 (3)
C22—C9—C10—C1	−0.5 (4)	C15—C14—C23—C24	0.6 (5)
C2—C1—C10—C9	−177.1 (3)	C22—C23—C24—N2	0.6 (5)
C2—C1—C10—C11	1.1 (4)	C14—C23—C24—N2	−179.7 (3)
C3—C4—C11—N1	179.3 (3)	C22—C23—C24—C17	−180.0 (3)
C3—C4—C11—C10	−0.6 (5)	C14—C23—C24—C17	−0.2 (4)
C9—C10—C11—N1	−2.3 (4)	C16—C17—C24—N2	179.2 (3)
C1—C10—C11—N1	179.4 (3)	C16—C17—C24—C23	−0.2 (5)
C9—C10—C11—C4	177.6 (3)	C19—C18—C25—N2	−179.4 (3)
C1—C10—C11—C4	−0.8 (4)	C19—C18—C25—C26	0.7 (5)
C6—C5—C12—N1	−178.6 (3)	C23—C22—C26—C25	1.1 (4)
C6—C5—C12—C13	1.4 (5)	C9—C22—C26—C25	−179.2 (3)
C10—C9—C13—C12	−0.1 (4)	C23—C22—C26—C21	−178.4 (3)
C22—C9—C13—C12	180.0 (3)	C9—C22—C26—C21	1.3 (4)
C10—C9—C13—C8	−179.4 (3)	N2—C25—C26—C22	0.2 (4)
C22—C9—C13—C8	0.7 (4)	C18—C25—C26—C22	−179.9 (3)
N1—C12—C13—C9	−0.4 (5)	N2—C25—C26—C21	179.7 (3)
C5—C12—C13—C9	179.6 (3)	C18—C25—C26—C21	−0.3 (4)
N1—C12—C13—C8	178.9 (3)	C20—C21—C26—C22	179.3 (3)
C5—C12—C13—C8	−1.0 (4)	C20—C21—C26—C25	−0.2 (4)
C7—C8—C13—C9	179.3 (3)	C4—C11—N1—C12	−178.1 (3)
C7—C8—C13—C12	0.0 (4)	C10—C11—N1—C12	1.8 (4)
C23—C14—C15—C16	−0.6 (5)	C5—C12—N1—C11	179.5 (3)
C14—C15—C16—C17	0.1 (6)	C13—C12—N1—C11	−0.4 (4)
C15—C16—C17—C24	0.3 (5)	C23—C24—N2—C25	0.6 (4)
C25—C18—C19—C20	−0.5 (5)	C17—C24—N2—C25	−178.8 (3)
C18—C19—C20—C21	−0.1 (5)	C18—C25—N2—C24	179.0 (3)
C19—C20—C21—C26	0.4 (5)	C26—C25—N2—C24	−1.1 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N2ⁱ	0.93	2.49	3.374 (5)	159
C21—H21A···N1ⁱⁱ	0.93	2.53	3.419 (4)	159
C19—H19A···Cg1ⁱⁱⁱ	0.93	2.88	3.764 (4)	159

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

Experimental details

Crystal data
Chemical formula	C₂₆H₁₆N₂
M_r	356.41
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	24.427 (8), 9.463 (3), 15.644 (5)
β (°)	98.253 (6)
V (Å³)	3578.9 (19)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.25 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector
Absorption correction	Multi-scan (SADABS; Bruker, 1998)
T_min, T_max	0.977, 0.981
No. of measured, independent and observed [I > 2σ(I)] reflections	8953, 3166, 1342
R_int	0.099
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.060, 0.113, 0.96
No. of reflections	3166
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.17

Computer programs: SMART (Bruker, 1998), SAINT (Bruker, 1998), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1998) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8A···N2ⁱ	0.93	2.49	3.374 (5)	159
C21—H21A···N1ⁱⁱ	0.93	2.53	3.419 (4)	159
C19—H19A···Cg1ⁱⁱⁱ	0.93	2.88	3.764 (4)	159

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

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