4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

Khan, F.N.; Manivel, P.; Prabakaran, K.; Hathwar, V.R.; Akkurt, M.

doi:10.1107/S1600536810013012

organic compounds

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ISSN: 2056-9890

Volume 66| Part 5| May 2010| Page o1081

https://doi.org/10.1107/S1600536810013012

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4-(5-Phenyl-1,2,4-triazolo[3,4-a]isoquinolin-3-yl)benzonitrile

F. Nawaz Khan,^a P. Manivel,^a K. Prabakaran,^a Venkatesha R. Hathwar ^b and Mehmet Akkurt ^c ^*

^aOrganic and Medicinal Chemistry Research Laboratory, Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore 632 014, Tamil Nadu, India, ^bSolid State and Structural Chemistry Unit, Indian Institute of Science, Bangalore 560 012, Karnataka, India, and ^cDepartment of Physics, Faculty of Arts and Sciences, Erciyes University, 38039 Kayseri, Turkey
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 3 April 2010; accepted 7 April 2010; online 14 April 2010)

In the title molecule, C₂₃H₁₄N₄, the triazoloisoquinoline ring system is nearly planar, with an r.m.s. deviation of 0.038 (2) Å and a maximum deviation of −0.030 (2) Å from the mean plane of the triazole ring C atom which is bonded to the benzene ring. The benzene and phenyl rings are twisted by 57.65 (8) and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. In the crystal structure, molecules are linked by weak aromatic π–π interactions [centroid–centroid distance = 3.8074 (12) Å]. In addition, the crystal structure exhibits a nonclassical intermolecular C—H⋯N hydrogen bond.

Related literature

For a related crystal structure, see: Khan et al. (2010 ).

Experimental

Crystal data

C₂₃H₁₄N₄
M_r = 346.38
Orthorhombic, P b c a
a = 7.1614 (3) Å
b = 18.0957 (7) Å
c = 26.4021 (9) Å
V = 3421.5 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 290 K
0.25 × 0.21 × 0.17 mm

Data collection

Oxford Xcalibur Eos (Nova) CCD detector diffractometer
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ) T_min = 0.959, T_max = 0.986
14977 measured reflections
3164 independent reflections
1490 reflections with I > 2σ(I)
R_int = 0.070

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.100
S = 0.81
3164 reflections
244 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C11—H11⋯N3ⁱ	0.93	2.50	3.418 (3)	170
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z]$ .

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); cell refinement: CrysAlis PRO CCD; data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England.]$ ); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810013012/rk2199sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810013012/rk2199Isup2.hkl

checkCIF report

Comment top

As part of our search for new isoquinoline analogues (Khan et al., 2010), we focused on synthesis of titled compounds and the crystal structure is reported.

In the title molecule, Fig. 1, the triazoloisoquinoline ring system (N1-N3/C1-C9/C16) is nearly planar, with an r.m.s. deviation of 0.038 (2)Å and a maximum deviation of -0.030 (2)Å from the mean plane for the triazole ring C16 atom which is bonded to the benzene ring (C17-C22). The benzene (C17-C22) and phenyl (C10-C15) rings are twisted by 57.65 (8)° and 53.60 (9)°, respectively, with respect to the mean plane of the triazoloisoquinoline ring system. The benzene (C17-C22) and phenyl (C10-C15) rings make a dihedral angle of 29.10 (11)° with each other.

Molecular conformation is stabilized by a weak π–π interaction [Cg4···Cg5 = 3.8229 (14)Å, where are Cg4 and Cg5 are centroids of the C10-C15 and C17-C22 rings, respectively]. In the crystal structure, the molecules are linked by weak aromatic π–π interactions [Cg1···Cg1ⁱⁱ = 3.8074 (12)Å, symmetry code: (ii) x-1/2, 1/2-y, -z. Cg1 is the centroid of the N1-N3/C1/C16 ring]. In addition, the crystal structure exhibits an intermolecular non-classical C–H···N hydrogen bond (Table 1, Fig. 2).

Related literature top

For a related crystal structure, see: Khan et al. (2010).

Experimental top

2-(3-Phenylisoquinolin-1-yl)hydrazine (1 mmol) was condensed with 4-formylbenzonitrile (1.1 mmol) under refluxing conditions isopropanol (10 ml) solvent to give the corresponding hydrazone in high yield. After removal of solvent the compound was then oxidatively cyclized in nitrobenzene (10 ml) at 473 K. The product was recrystallized from dichlomethane to give block-shaped crystals.

Structure description top

As part of our search for new isoquinoline analogues (Khan et al., 2010), we focused on synthesis of titled compounds and the crystal structure is reported.

For a related crystal structure, see: Khan et al. (2010).

Computing details top

Data collection: CrysAlis PRO CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO CCD (Oxford Diffraction, 2009); data reduction: CrysAlis PRO RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The view of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are presented as a small spheres of arbitrary radius.
	Fig. 2. The packing diagram and the hydrogen bonding in the title crystal structure viewed down the [1 0 0] direction. H atoms not involved in the motif shown have been omitted for clarity.

(I) top

Crystal data top

C₂₃H₁₄N₄	F(000) = 1440
M_r = 346.38	D_x = 1.345 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 1235 reflections
a = 7.1614 (3) Å	θ = 1.6–20.4°
b = 18.0957 (7) Å	µ = 0.08 mm⁻¹
c = 26.4021 (9) Å	T = 290 K
V = 3421.5 (2) Å³	Block, colourless
Z = 8	0.25 × 0.21 × 0.17 mm

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	3164 independent reflections
Radiation source: Enhance (Mo) X-ray Source	1490 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.070
ω scans	θ_max = 25.5°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	h = −8→7
T_min = 0.959, T_max = 0.986	k = −21→21
14977 measured reflections	l = −31→31

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.100	H-atom parameters constrained
S = 0.81	w = 1/[σ²(F_o²) + (0.0413P)²] where P = (F_o² + 2F_c²)/3
3164 reflections	(Δ/σ)_max < 0.001
244 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.20 e Å⁻³

Crystal data top

C₂₃H₁₄N₄	V = 3421.5 (2) Å³
M_r = 346.38	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 7.1614 (3) Å	µ = 0.08 mm⁻¹
b = 18.0957 (7) Å	T = 290 K
c = 26.4021 (9) Å	0.25 × 0.21 × 0.17 mm

Data collection top

Oxford Xcalibur Eos (Nova) CCD detector diffractometer	3164 independent reflections
Absorption correction: multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)	1490 reflections with I > 2σ(I)
T_min = 0.959, T_max = 0.986	R_int = 0.070
14977 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.100	H-atom parameters constrained
S = 0.81	Δρ_max = 0.15 e Å⁻³
3164 reflections	Δρ_min = −0.20 e Å⁻³
244 parameters

Special details top

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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	0.6627 (2)	0.33099 (9)	0.03366 (6)	0.0370 (4)
N2	0.5820 (3)	0.22467 (10)	−0.00072 (7)	0.0510 (5)
N3	0.6063 (2)	0.27481 (11)	−0.03950 (7)	0.0495 (5)
N4	0.5390 (3)	0.08980 (15)	0.27259 (9)	0.0927 (9)
C1	0.6539 (3)	0.33812 (13)	−0.01851 (8)	0.0395 (5)
C2	0.6915 (3)	0.40722 (12)	−0.04237 (8)	0.0407 (6)
C3	0.6888 (3)	0.41638 (14)	−0.09495 (8)	0.0490 (6)
H3	0.6586	0.3766	−0.1157	0.059*
C4	0.7302 (3)	0.48368 (15)	−0.11611 (9)	0.0570 (7)
H4	0.7297	0.4894	−0.1511	0.068*
C5	0.7728 (3)	0.54308 (14)	−0.08507 (9)	0.0581 (7)
H5	0.8002	0.5887	−0.0996	0.070*
C6	0.7754 (3)	0.53585 (13)	−0.03328 (9)	0.0526 (6)
H6	0.8030	0.5764	−0.0130	0.063*
C7	0.7364 (3)	0.46741 (12)	−0.01110 (8)	0.0416 (6)
C8	0.7527 (3)	0.45523 (12)	0.04249 (8)	0.0454 (6)
H8	0.7853	0.4952	0.0628	0.054*
C9	0.7238 (3)	0.38972 (12)	0.06498 (8)	0.0387 (6)
C10	0.7671 (3)	0.37673 (11)	0.11909 (8)	0.0374 (5)
C11	0.8907 (3)	0.32192 (12)	0.13406 (8)	0.0456 (6)
H11	0.9426	0.2903	0.1101	0.055*
C12	0.9365 (3)	0.31454 (14)	0.18466 (9)	0.0562 (7)
H12	1.0180	0.2774	0.1948	0.067*
C13	0.8625 (4)	0.36161 (15)	0.22007 (9)	0.0645 (8)
H13	0.8935	0.3561	0.2541	0.077*
C14	0.7438 (4)	0.41647 (15)	0.20553 (9)	0.0595 (7)
H14	0.6960	0.4490	0.2295	0.071*
C15	0.6944 (3)	0.42380 (13)	0.15537 (9)	0.0478 (6)
H15	0.6114	0.4608	0.1458	0.057*
C16	0.6137 (3)	0.25837 (12)	0.04252 (8)	0.0406 (6)
C17	0.5906 (3)	0.22246 (12)	0.09194 (8)	0.0403 (5)
C18	0.6918 (3)	0.15870 (13)	0.10218 (8)	0.0480 (6)
H18	0.7701	0.1391	0.0775	0.058*
C19	0.6771 (3)	0.12414 (12)	0.14857 (9)	0.0523 (6)
H19	0.7474	0.0821	0.1554	0.063*
C20	0.5575 (3)	0.15217 (13)	0.18497 (8)	0.0480 (6)
C21	0.4514 (3)	0.21414 (13)	0.17476 (8)	0.0524 (6)
H21	0.3693	0.2324	0.1990	0.063*
C22	0.4678 (3)	0.24882 (13)	0.12834 (8)	0.0503 (6)
H22	0.3957	0.2903	0.1214	0.060*
C23	0.5459 (3)	0.11720 (15)	0.23405 (10)	0.0629 (8)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0393 (10)	0.0337 (11)	0.0381 (11)	−0.0026 (8)	−0.0031 (8)	−0.0012 (9)
N2	0.0631 (13)	0.0439 (12)	0.0459 (12)	−0.0068 (10)	−0.0062 (10)	−0.0041 (11)
N3	0.0614 (13)	0.0457 (13)	0.0414 (11)	−0.0057 (10)	−0.0054 (9)	0.0003 (10)
N4	0.0964 (19)	0.124 (2)	0.0576 (16)	0.0151 (16)	0.0099 (14)	0.0261 (16)
C1	0.0394 (14)	0.0404 (15)	0.0387 (13)	−0.0003 (11)	−0.0054 (10)	−0.0027 (12)
C2	0.0357 (13)	0.0443 (15)	0.0421 (14)	0.0023 (11)	−0.0010 (10)	0.0016 (12)
C3	0.0463 (15)	0.0544 (17)	0.0463 (15)	0.0062 (13)	0.0002 (11)	0.0032 (13)
C4	0.0515 (17)	0.0687 (19)	0.0507 (15)	0.0085 (14)	0.0028 (12)	0.0160 (15)
C5	0.0464 (16)	0.0584 (19)	0.0695 (19)	−0.0011 (13)	−0.0002 (13)	0.0241 (15)
C6	0.0500 (15)	0.0465 (16)	0.0613 (17)	−0.0003 (12)	−0.0016 (13)	0.0076 (13)
C7	0.0344 (14)	0.0413 (15)	0.0490 (14)	0.0004 (11)	−0.0046 (11)	0.0072 (12)
C8	0.0461 (14)	0.0387 (15)	0.0513 (15)	−0.0011 (11)	−0.0052 (12)	−0.0054 (12)
C9	0.0347 (14)	0.0368 (15)	0.0445 (13)	−0.0002 (10)	−0.0019 (11)	−0.0060 (11)
C10	0.0399 (14)	0.0336 (13)	0.0386 (13)	−0.0029 (11)	−0.0012 (10)	−0.0018 (11)
C11	0.0441 (14)	0.0436 (15)	0.0492 (15)	−0.0011 (12)	−0.0005 (11)	−0.0047 (12)
C12	0.0519 (16)	0.0604 (18)	0.0563 (17)	0.0036 (13)	−0.0129 (13)	0.0072 (15)
C13	0.075 (2)	0.077 (2)	0.0416 (15)	−0.0091 (16)	−0.0111 (14)	0.0000 (15)
C14	0.0721 (18)	0.0580 (18)	0.0483 (16)	−0.0068 (15)	0.0073 (14)	−0.0115 (14)
C15	0.0507 (15)	0.0429 (15)	0.0497 (15)	0.0013 (12)	0.0008 (12)	−0.0051 (13)
C16	0.0436 (14)	0.0361 (14)	0.0423 (13)	−0.0039 (11)	−0.0025 (11)	−0.0031 (12)
C17	0.0400 (13)	0.0351 (14)	0.0458 (14)	−0.0048 (11)	−0.0039 (11)	−0.0015 (11)
C18	0.0586 (15)	0.0392 (15)	0.0463 (15)	0.0034 (13)	0.0039 (12)	−0.0031 (12)
C19	0.0637 (17)	0.0400 (15)	0.0532 (16)	0.0085 (12)	0.0004 (13)	0.0023 (13)
C20	0.0498 (15)	0.0497 (16)	0.0446 (14)	−0.0053 (13)	−0.0014 (12)	0.0051 (13)
C21	0.0516 (16)	0.0559 (17)	0.0497 (16)	0.0024 (14)	0.0067 (12)	−0.0002 (13)
C22	0.0516 (16)	0.0417 (15)	0.0575 (16)	0.0052 (12)	−0.0014 (13)	0.0000 (13)
C23	0.0591 (18)	0.075 (2)	0.0546 (18)	0.0052 (14)	0.0030 (14)	0.0043 (16)

Geometric parameters (Å, º) top

N1—C16	1.380 (2)	C10—C11	1.387 (3)
N1—C1	1.385 (2)	C11—C12	1.382 (3)
N1—C9	1.416 (2)	C11—H11	0.9300
N2—C16	1.314 (2)	C12—C13	1.371 (3)
N2—N3	1.379 (2)	C12—H12	0.9300
N3—C1	1.318 (3)	C13—C14	1.362 (3)
N4—C23	1.133 (3)	C13—H13	0.9300
C1—C2	1.426 (3)	C14—C15	1.377 (3)
C2—C3	1.398 (3)	C14—H14	0.9300
C2—C7	1.404 (3)	C15—H15	0.9300
C3—C4	1.372 (3)	C16—C17	1.467 (3)
C3—H3	0.9300	C17—C22	1.387 (3)
C4—C5	1.386 (3)	C17—C18	1.389 (3)
C4—H4	0.9300	C18—C19	1.379 (3)
C5—C6	1.374 (3)	C18—H18	0.9300
C5—H5	0.9300	C19—C20	1.384 (3)
C6—C7	1.398 (3)	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.381 (3)
C7—C8	1.437 (3)	C20—C23	1.445 (3)
C8—C9	1.342 (3)	C21—C22	1.382 (3)
C8—H8	0.9300	C21—H21	0.9300
C9—C10	1.481 (3)	C22—H22	0.9300
C10—C15	1.384 (3)

C16—N1—C1	104.23 (17)	C12—C11—H11	120.1
C16—N1—C9	133.97 (18)	C10—C11—H11	120.1
C1—N1—C9	121.67 (19)	C13—C12—C11	120.5 (2)
C16—N2—N3	108.54 (17)	C13—C12—H12	119.7
C1—N3—N2	107.01 (17)	C11—C12—H12	119.7
N3—C1—N1	110.4 (2)	C14—C13—C12	120.1 (2)
N3—C1—C2	128.7 (2)	C14—C13—H13	119.9
N1—C1—C2	120.8 (2)	C12—C13—H13	119.9
C3—C2—C7	119.7 (2)	C13—C14—C15	120.1 (2)
C3—C2—C1	122.7 (2)	C13—C14—H14	120.0
C7—C2—C1	117.6 (2)	C15—C14—H14	120.0
C4—C3—C2	120.4 (2)	C14—C15—C10	120.7 (2)
C4—C3—H3	119.8	C14—C15—H15	119.7
C2—C3—H3	119.8	C10—C15—H15	119.7
C3—C4—C5	119.7 (2)	N2—C16—N1	109.78 (18)
C3—C4—H4	120.2	N2—C16—C17	123.23 (19)
C5—C4—H4	120.2	N1—C16—C17	126.94 (19)
C6—C5—C4	121.2 (2)	C22—C17—C18	118.8 (2)
C6—C5—H5	119.4	C22—C17—C16	122.4 (2)
C4—C5—H5	119.4	C18—C17—C16	118.8 (2)
C5—C6—C7	119.9 (2)	C19—C18—C17	120.6 (2)
C5—C6—H6	120.0	C19—C18—H18	119.7
C7—C6—H6	120.0	C17—C18—H18	119.7
C6—C7—C2	119.1 (2)	C18—C19—C20	119.9 (2)
C6—C7—C8	122.1 (2)	C18—C19—H19	120.1
C2—C7—C8	118.6 (2)	C20—C19—H19	120.1
C9—C8—C7	124.0 (2)	C21—C20—C19	120.2 (2)
C9—C8—H8	118.0	C21—C20—C23	119.9 (2)
C7—C8—H8	118.0	C19—C20—C23	119.9 (2)
C8—C9—N1	116.90 (19)	C20—C21—C22	119.7 (2)
C8—C9—C10	122.32 (19)	C20—C21—H21	120.2
N1—C9—C10	120.61 (19)	C22—C21—H21	120.2
C15—C10—C11	118.9 (2)	C21—C22—C17	120.8 (2)
C15—C10—C9	119.4 (2)	C21—C22—H22	119.6
C11—C10—C9	121.49 (19)	C17—C22—H22	119.6
C12—C11—C10	119.7 (2)	N4—C23—C20	179.2 (3)

C16—N2—N3—C1	0.5 (2)	N1—C9—C10—C15	−131.8 (2)
N2—N3—C1—N1	0.3 (2)	C8—C9—C10—C11	−121.8 (2)
N2—N3—C1—C2	−178.9 (2)	N1—C9—C10—C11	53.2 (3)
C16—N1—C1—N3	−0.9 (2)	C15—C10—C11—C12	1.0 (3)
C9—N1—C1—N3	175.46 (16)	C9—C10—C11—C12	176.0 (2)
C16—N1—C1—C2	178.40 (18)	C10—C11—C12—C13	−0.9 (3)
C9—N1—C1—C2	−5.2 (3)	C11—C12—C13—C14	−0.4 (4)
N3—C1—C2—C3	−2.5 (3)	C12—C13—C14—C15	1.4 (4)
N1—C1—C2—C3	178.35 (17)	C13—C14—C15—C10	−1.3 (4)
N3—C1—C2—C7	178.8 (2)	C11—C10—C15—C14	0.0 (3)
N1—C1—C2—C7	−0.4 (3)	C9—C10—C15—C14	−175.0 (2)
C7—C2—C3—C4	0.2 (3)	N3—N2—C16—N1	−1.0 (2)
C1—C2—C3—C4	−178.5 (2)	N3—N2—C16—C17	176.63 (18)
C2—C3—C4—C5	−0.8 (3)	C1—N1—C16—N2	1.2 (2)
C3—C4—C5—C6	0.4 (3)	C9—N1—C16—N2	−174.51 (19)
C4—C5—C6—C7	0.7 (3)	C1—N1—C16—C17	−176.38 (19)
C5—C6—C7—C2	−1.2 (3)	C9—N1—C16—C17	7.9 (4)
C5—C6—C7—C8	174.57 (19)	N2—C16—C17—C22	−120.5 (2)
C3—C2—C7—C6	0.8 (3)	N1—C16—C17—C22	56.7 (3)
C1—C2—C7—C6	179.55 (19)	N2—C16—C17—C18	57.8 (3)
C3—C2—C7—C8	−175.16 (18)	N1—C16—C17—C18	−125.0 (2)
C1—C2—C7—C8	3.6 (3)	C22—C17—C18—C19	−3.0 (3)
C6—C7—C8—C9	−177.2 (2)	C16—C17—C18—C19	178.6 (2)
C2—C7—C8—C9	−1.5 (3)	C17—C18—C19—C20	1.4 (3)
C7—C8—C9—N1	−3.9 (3)	C18—C19—C20—C21	0.7 (3)
C7—C8—C9—C10	171.32 (18)	C18—C19—C20—C23	−178.3 (2)
C16—N1—C9—C8	−177.6 (2)	C19—C20—C21—C22	−1.2 (3)
C1—N1—C9—C8	7.3 (3)	C23—C20—C21—C22	177.8 (2)
C16—N1—C9—C10	7.0 (3)	C20—C21—C22—C17	−0.4 (3)
C1—N1—C9—C10	−168.06 (17)	C18—C17—C22—C21	2.5 (3)
C8—C9—C10—C15	53.1 (3)	C16—C17—C22—C21	−179.2 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N3ⁱ	0.93	2.50	3.418 (3)	170

Symmetry code: (i) x+1/2, −y+1/2, −z.

Experimental details

Crystal data
Chemical formula	C₂₃H₁₄N₄
M_r	346.38
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	290
a, b, c (Å)	7.1614 (3), 18.0957 (7), 26.4021 (9)
V (Å³)	3421.5 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.25 × 0.21 × 0.17

Data collection
Diffractometer	Oxford Xcalibur Eos (Nova) CCD detector
Absorption correction	Multi-scan (CrysAlis PRO RED; Oxford Diffraction, 2009)
T_min, T_max	0.959, 0.986
No. of measured, independent and observed [I > 2σ(I)] reflections	14977, 3164, 1490
R_int	0.070
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.100, 0.81
No. of reflections	3164
No. of parameters	244
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.20

Computer programs: CrysAlis PRO CCD (Oxford Diffraction, 2009), CrysAlis PRO RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C11—H11···N3ⁱ	0.93	2.50	3.418 (3)	170

Symmetry code: (i) x+1/2, −y+1/2, −z.

Acknowledgements

The authors thank the FIST program for data collection on the Oxford single-crystal diffractometer at SSCU, IISc, Bangalore. The authors also thank Professor T. N. Guru Row, IISc, Bangalore, for his help with the data collection. FNK thanks the DST for Fast Track Proposal funding.

References

Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Khan, F. N., Manivel, P., Prabakaran, K., Hathwar, V. R. & Ng, S. W. (2010). Acta Cryst. E66, o488. Web of Science CSD CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO CCD and CrysAlis PRO RED. Oxford Diffraction Ltd, Yarnton, Oxfordshire, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar