5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)meth­yl]-5H-dibenzo[b,f]azepine

Manjunath, B.C.; Vinay Kumar, K.S.; Madan Kumar, S.; Sadashiva, M.P.; Lokanath, N.K.

doi:10.1107/S1600536813018412

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 69| Part 8| August 2013| Page o1233

doi:10.1107/S1600536813018412

Open

access

5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)methyl]-5H-dibenzo[b,f]azepine

B. C. Manjunath,^a K. S. Vinay Kumar,^b S. Madan Kumar,^a M. P. Sadashiva ^b and N. K. Lokanath ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India
^*Correspondence e-mail: lokanath@physics.uni-mysore.ac.in

(Received 24 June 2013; accepted 3 July 2013; online 10 July 2013)

In the title compound, C₂₄H₂₀N₄, the azepine ring adopts a boat conformation and the dihedral angle between the benzene rings fused to it is 57.95 (8)°. The bond-angle sum at the azepine N atom is 346.6°, indicating a significant deviation from planarity. The triazole ring subtends a dihedral angle of 71.45 (10)° with the terminal phenyl group. A weak intramolecular C—H⋯N_a (a = azepine) interaction occurs, which closes an S(6) ring.

Related literature

For a related structure and background to isoxazole derivatives, see: Abdoh et al. (2013 ).

Experimental

Crystal data

C₂₄H₂₀N₄
M_r = 364.44
Monoclinic, P 2₁ /c
a = 9.4394 (10) Å
b = 22.206 (3) Å
c = 9.4330 (9) Å
β = 107.172 (3)°
V = 1889.1 (4) Å³
Z = 4
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 300 K
0.26 × 0.23 × 0.20 mm

Data collection

Bruker APEXII CCD diffractometer
22703 measured reflections
3711 independent reflections
2982 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.01
3711 reflections
253 parameters
H-atom parameters constrained
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7A⋯N4	0.97	2.56	3.173 (2)	121

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: Mercury.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813018412/hb7099sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813018412/hb7099Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813018412/hb7099Isup3.cml

checkCIF report

Comment top

The title compound was synthesized, crystallized and its crystal structure is presented as part of our investigations on isoxazole derivatives (Abdoh, et al.,, 2013)

In the title molecule (Fig. 1.) benzene rings fused to azepine rings are nearly planar and its geometry is similar to 5-(Prop-2–1-yl)-5H-dibenzo[b,f]azepine: orthorhombic polymorph. Seven-membered azepine ring adopts a boat conformation as indicated by the puckering parameters Q₂ = 0.7392 (16) Å, Q₃ = 0.2157 (15) Å, ϕ₂ = 178.44 (12) °, ϕ₃ = 178.4 (4) °, and the total puckering amplitude, Q_T = 0.7700 (15) Å. The title molecule adopts butterfly shape. The dihedral angle between triazole moiety and benzene ring (C1/C2/C3/C4/C5/C6) is 71.45 (10)°. The packing of molecules is shown in the figure 2.

Related literature top

For a related structure and background to isoxazole derivatives, see: Abdoh et al. (2013).

Experimental top

5-(prop-2-yn-1-yl)-5H-dibenzo[b,f]azepine (2.1 mmol) was taken in a mixture of dichloromethane and water in the ratio 1:1, cuprous iodide (0.21 mmol) was added followed by sodium ascorbate (0.21 mmol) at room temperature. After 10 minutes, benzyl azide was added (2.3 mmol) at room temperature. Then, the resulting reaction mixture was allowed for stirring upto 6 h. After completion of reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 x 20 ml), the combined ethyl acetate layer was washed with brine solution (2 x 25 ml). Then, the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford crude, which was purified by column chromatography over silica gel (60–120 mesh) using Hexane: Ethyl acetate mixture in 8:2 ratios as eluent. The pure compound was crystallized in ethyl acetate and hexane to obtain light red blocks.

¹H NMR (DMSO-d6, 300 MHz): δ 7.33 (t, J=7.2 Hz, 2H), 7.13 (t, J=8.7 Hz, 4H), 7.02 (t, J=7.2 Hz, 2H), 6.75 (s, 2H), 4.51 (d, J=1.8 Hz, 2H), 3.08 (s, 1H).

MS (M⁺+1): 232. Melting point (°C): 90 (Uncorrected)

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: Mercury (Macrae et al., 2006).

Figures top

	Fig. 1. View of the title molecule with 50% probability ellipsoids.
	Fig. 2. Packing diagram of molecule, viewed along the crystallographic a axis.

5-[(4-Benzyl-1H-1,2,3-triazol-1-yl)methyl]-5H-dibenzo[b,f]azepine top

Crystal data top

C₂₄H₂₀N₄	F(000) = 768
M_r = 364.44	D_x = 1.281 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3711 reflections
a = 9.4394 (10) Å	θ = 1.8–26.0°
b = 22.206 (3) Å	µ = 0.08 mm⁻¹
c = 9.4330 (9) Å	T = 300 K
β = 107.172 (3)°	Block, red
V = 1889.1 (4) Å³	0.26 × 0.23 × 0.20 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	R_int = 0.045
Radiation source: graphite	θ_max = 26.0°, θ_min = 1.8°
ϕ and ω scans	h = −11→11
22703 measured reflections	k = −27→26
3711 independent reflections	l = −11→11
2982 reflections with I > 2σ(I)

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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0634P)² + 0.445P] where P = (F_o² + 2F_c²)/3
3711 reflections	(Δ/σ)_max < 0.001
253 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₂₄H₂₀N₄	V = 1889.1 (4) Å³
M_r = 364.44	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.4394 (10) Å	µ = 0.08 mm⁻¹
b = 22.206 (3) Å	T = 300 K
c = 9.4330 (9) Å	0.26 × 0.23 × 0.20 mm
β = 107.172 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2982 reflections with I > 2σ(I)
22703 measured reflections	R_int = 0.045
3711 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.01	Δρ_max = 0.16 e Å⁻³
3711 reflections	Δρ_min = −0.23 e Å⁻³
253 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs 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	0.48315 (15)	0.41800 (6)	0.71285 (15)	0.0485 (4)
N2	0.59240 (19)	0.44728 (7)	0.81571 (19)	0.0671 (6)
N3	0.68625 (18)	0.40672 (9)	0.89031 (18)	0.0687 (6)
N4	0.35717 (13)	0.32303 (5)	0.47460 (12)	0.0358 (3)
C1	0.0910 (2)	0.43114 (8)	0.5802 (2)	0.0602 (6)
C2	0.22436 (19)	0.45366 (6)	0.66850 (18)	0.0475 (5)
C3	0.2290 (2)	0.48013 (7)	0.8030 (2)	0.0536 (6)
C4	0.1028 (2)	0.48466 (8)	0.8465 (2)	0.0605 (6)
C5	−0.0294 (2)	0.46273 (8)	0.7577 (3)	0.0667 (7)
C6	−0.0358 (2)	0.43573 (8)	0.6250 (3)	0.0690 (7)
C7	0.3606 (2)	0.45281 (7)	0.6163 (2)	0.0562 (6)
C8	0.63739 (19)	0.35255 (9)	0.83410 (18)	0.0551 (5)
C9	0.50799 (17)	0.35803 (7)	0.72201 (15)	0.0410 (4)
C10	0.40884 (17)	0.31033 (7)	0.63385 (15)	0.0408 (4)
C11	0.46560 (15)	0.33324 (6)	0.39878 (15)	0.0357 (4)
C12	0.42678 (17)	0.37101 (6)	0.27384 (16)	0.0404 (4)
C13	0.5336 (2)	0.38298 (7)	0.20193 (19)	0.0527 (6)
C14	0.6730 (2)	0.35838 (9)	0.2500 (2)	0.0600 (6)
C15	0.71005 (19)	0.32105 (8)	0.3721 (2)	0.0553 (6)
C16	0.60713 (17)	0.30859 (7)	0.44645 (17)	0.0445 (5)
C17	0.27898 (19)	0.39760 (7)	0.21582 (17)	0.0478 (5)
C18	0.15052 (19)	0.37247 (7)	0.21404 (18)	0.0484 (5)
C19	0.13042 (16)	0.31254 (7)	0.26945 (16)	0.0402 (4)
C20	0.23460 (15)	0.28684 (6)	0.39198 (14)	0.0353 (4)
C21	0.00604 (17)	0.27797 (8)	0.19635 (18)	0.0523 (5)
C22	−0.01154 (19)	0.21998 (9)	0.2393 (2)	0.0582 (6)
C23	0.0936 (2)	0.19481 (8)	0.35653 (19)	0.0544 (6)
C24	0.21656 (18)	0.22797 (7)	0.43327 (17)	0.0447 (5)
H1	0.08630	0.41280	0.49030	0.0720*
H3	0.31830	0.49490	0.86420	0.0640*
H4	0.10710	0.50270	0.93670	0.0730*
H5	−0.11480	0.46610	0.78720	0.0800*
H6	−0.12530	0.42050	0.56520	0.0830*
H7A	0.33470	0.43590	0.51710	0.0670*
H7B	0.39350	0.49390	0.61070	0.0670*
H8	0.68500	0.31630	0.86690	0.0660*
H10A	0.46180	0.27230	0.64940	0.0490*
H10B	0.32350	0.30600	0.67030	0.0490*
H13	0.50970	0.40820	0.11960	0.0630*
H14	0.74230	0.36690	0.20030	0.0720*
H15	0.80430	0.30420	0.40460	0.0660*
H16	0.63290	0.28350	0.52900	0.0530*
H17	0.27440	0.43610	0.17600	0.0570*
H18	0.06540	0.39520	0.17370	0.0580*
H21	−0.06640	0.29470	0.11680	0.0630*
H22	−0.09480	0.19790	0.18860	0.0700*
H23	0.08250	0.15540	0.38470	0.0650*
H24	0.28760	0.21070	0.51300	0.0540*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0535 (8)	0.0486 (7)	0.0494 (8)	−0.0117 (6)	0.0243 (7)	−0.0132 (6)
N2	0.0721 (11)	0.0676 (10)	0.0667 (10)	−0.0319 (8)	0.0284 (9)	−0.0278 (8)
N3	0.0584 (9)	0.0904 (12)	0.0560 (9)	−0.0262 (9)	0.0148 (8)	−0.0203 (9)
N4	0.0388 (6)	0.0403 (6)	0.0274 (6)	−0.0056 (5)	0.0084 (5)	−0.0010 (5)
C1	0.0747 (12)	0.0467 (9)	0.0548 (10)	0.0002 (8)	0.0122 (9)	−0.0074 (8)
C2	0.0605 (10)	0.0334 (7)	0.0510 (9)	0.0017 (7)	0.0203 (8)	−0.0009 (6)
C3	0.0587 (10)	0.0483 (9)	0.0551 (10)	−0.0030 (7)	0.0190 (8)	−0.0087 (7)
C4	0.0681 (12)	0.0592 (10)	0.0615 (11)	0.0058 (9)	0.0305 (10)	−0.0041 (8)
C5	0.0601 (12)	0.0564 (11)	0.0906 (15)	0.0077 (9)	0.0329 (11)	0.0111 (10)
C6	0.0547 (11)	0.0542 (10)	0.0881 (15)	−0.0045 (8)	0.0056 (10)	0.0011 (10)
C7	0.0755 (12)	0.0450 (9)	0.0562 (10)	0.0010 (8)	0.0319 (9)	−0.0008 (7)
C8	0.0511 (9)	0.0718 (11)	0.0393 (8)	−0.0110 (8)	0.0085 (7)	−0.0070 (8)
C9	0.0454 (8)	0.0498 (8)	0.0310 (7)	−0.0091 (6)	0.0164 (6)	−0.0051 (6)
C10	0.0476 (8)	0.0450 (8)	0.0285 (7)	−0.0077 (6)	0.0092 (6)	−0.0005 (6)
C11	0.0412 (7)	0.0350 (7)	0.0309 (7)	−0.0060 (5)	0.0108 (6)	−0.0053 (5)
C12	0.0506 (8)	0.0365 (7)	0.0350 (7)	−0.0059 (6)	0.0139 (7)	−0.0016 (6)
C13	0.0663 (11)	0.0538 (9)	0.0420 (9)	−0.0098 (8)	0.0222 (8)	0.0044 (7)
C14	0.0581 (11)	0.0758 (12)	0.0545 (10)	−0.0136 (9)	0.0297 (9)	−0.0049 (9)
C15	0.0427 (9)	0.0717 (11)	0.0528 (10)	−0.0017 (8)	0.0159 (8)	−0.0090 (8)
C16	0.0449 (8)	0.0506 (8)	0.0368 (8)	−0.0016 (7)	0.0101 (7)	−0.0024 (6)
C17	0.0645 (10)	0.0375 (8)	0.0393 (8)	0.0062 (7)	0.0123 (7)	0.0068 (6)
C18	0.0516 (9)	0.0478 (8)	0.0419 (8)	0.0150 (7)	0.0079 (7)	0.0031 (6)
C19	0.0362 (7)	0.0493 (8)	0.0352 (7)	0.0042 (6)	0.0106 (6)	−0.0033 (6)
C20	0.0364 (7)	0.0410 (7)	0.0293 (7)	−0.0022 (6)	0.0109 (6)	−0.0046 (5)
C21	0.0367 (8)	0.0746 (11)	0.0409 (8)	0.0023 (7)	0.0041 (7)	−0.0035 (8)
C22	0.0477 (9)	0.0767 (12)	0.0487 (10)	−0.0226 (8)	0.0118 (8)	−0.0122 (8)
C23	0.0641 (11)	0.0534 (9)	0.0448 (9)	−0.0206 (8)	0.0145 (8)	−0.0045 (7)
C24	0.0500 (9)	0.0468 (8)	0.0351 (8)	−0.0079 (7)	0.0090 (7)	0.0003 (6)

Geometric parameters (Å, º) top

N1—N2	1.355 (2)	C19—C20	1.399 (2)
N1—C7	1.464 (2)	C19—C21	1.402 (2)
N1—C9	1.351 (2)	C20—C24	1.389 (2)
N2—N3	1.313 (3)	C21—C22	1.375 (3)
N3—C8	1.340 (3)	C22—C23	1.368 (3)
N4—C10	1.4634 (17)	C23—C24	1.385 (2)
N4—C11	1.4293 (19)	C1—H1	0.9300
N4—C20	1.4351 (18)	C3—H3	0.9300
C1—C2	1.382 (3)	C4—H4	0.9300
C1—C6	1.386 (3)	C5—H5	0.9300
C2—C3	1.387 (2)	C6—H6	0.9300
C2—C7	1.507 (3)	C7—H7A	0.9700
C3—C4	1.373 (3)	C7—H7B	0.9700
C4—C5	1.371 (3)	C8—H8	0.9300
C5—C6	1.373 (4)	C10—H10A	0.9700
C8—C9	1.365 (2)	C10—H10B	0.9700
C9—C10	1.493 (2)	C13—H13	0.9300
C11—C12	1.404 (2)	C14—H14	0.9300
C11—C16	1.390 (2)	C15—H15	0.9300
C12—C13	1.397 (2)	C16—H16	0.9300
C12—C17	1.464 (2)	C17—H17	0.9300
C13—C14	1.372 (3)	C18—H18	0.9300
C14—C15	1.378 (3)	C21—H21	0.9300
C15—C16	1.384 (2)	C22—H22	0.9300
C17—C18	1.330 (3)	C23—H23	0.9300
C18—C19	1.463 (2)	C24—H24	0.9300

N2—N1—C7	119.12 (13)	C20—C24—C23	120.48 (15)
N2—N1—C9	110.26 (13)	C2—C1—H1	120.00
C7—N1—C9	130.61 (14)	C6—C1—H1	120.00
N1—N2—N3	107.76 (15)	C2—C3—H3	120.00
N2—N3—C8	107.75 (16)	C4—C3—H3	120.00
C10—N4—C11	118.25 (12)	C3—C4—H4	120.00
C10—N4—C20	114.87 (11)	C5—C4—H4	120.00
C11—N4—C20	113.50 (11)	C4—C5—H5	120.00
C2—C1—C6	120.31 (18)	C6—C5—H5	120.00
C1—C2—C3	118.80 (17)	C1—C6—H6	120.00
C1—C2—C7	120.80 (15)	C5—C6—H6	120.00
C3—C2—C7	120.31 (16)	N1—C7—H7A	109.00
C2—C3—C4	120.55 (17)	N1—C7—H7B	109.00
C3—C4—C5	120.32 (18)	C2—C7—H7A	109.00
C4—C5—C6	119.96 (19)	C2—C7—H7B	109.00
C1—C6—C5	120.0 (2)	H7A—C7—H7B	108.00
N1—C7—C2	113.40 (14)	N3—C8—H8	125.00
N3—C8—C9	110.56 (17)	C9—C8—H8	125.00
N1—C9—C8	103.67 (14)	N4—C10—H10A	109.00
N1—C9—C10	126.54 (14)	N4—C10—H10B	109.00
C8—C9—C10	129.70 (15)	C9—C10—H10A	109.00
N4—C10—C9	113.52 (12)	C9—C10—H10B	109.00
N4—C11—C12	117.83 (13)	H10A—C10—H10B	108.00
N4—C11—C16	122.52 (12)	C12—C13—H13	119.00
C12—C11—C16	119.64 (14)	C14—C13—H13	119.00
C11—C12—C13	118.32 (15)	C13—C14—H14	120.00
C11—C12—C17	122.57 (14)	C15—C14—H14	120.00
C13—C12—C17	119.11 (14)	C14—C15—H15	120.00
C12—C13—C14	121.53 (16)	C16—C15—H15	120.00
C13—C14—C15	119.85 (18)	C11—C16—H16	120.00
C14—C15—C16	120.07 (17)	C15—C16—H16	120.00
C11—C16—C15	120.59 (15)	C12—C17—H17	117.00
C12—C17—C18	126.86 (14)	C18—C17—H17	117.00
C17—C18—C19	126.24 (16)	C17—C18—H18	117.00
C18—C19—C20	122.19 (14)	C19—C18—H18	117.00
C18—C19—C21	120.05 (14)	C19—C21—H21	119.00
C20—C19—C21	117.73 (14)	C22—C21—H21	119.00
N4—C20—C19	118.53 (12)	C21—C22—H22	120.00
N4—C20—C24	121.38 (12)	C23—C22—H22	120.00
C19—C20—C24	120.08 (14)	C22—C23—H23	120.00
C19—C21—C22	121.63 (16)	C24—C23—H23	120.00
C21—C22—C23	119.93 (17)	C20—C24—H24	120.00
C22—C23—C24	120.09 (17)	C23—C24—H24	120.00

C7—N1—N2—N3	178.33 (15)	N3—C8—C9—C10	−175.78 (16)
C9—N1—N2—N3	−0.1 (2)	N1—C9—C10—N4	48.1 (2)
N2—N1—C7—C2	−97.83 (18)	C8—C9—C10—N4	−136.11 (17)
C9—N1—C7—C2	80.2 (2)	N4—C11—C12—C13	177.82 (13)
N2—N1—C9—C8	−0.40 (18)	N4—C11—C12—C17	−2.8 (2)
N2—N1—C9—C10	176.29 (15)	C16—C11—C12—C13	−0.6 (2)
C7—N1—C9—C8	−178.59 (17)	C16—C11—C12—C17	178.82 (14)
C7—N1—C9—C10	−1.9 (3)	N4—C11—C16—C15	−178.14 (14)
N1—N2—N3—C8	0.6 (2)	C12—C11—C16—C15	0.1 (2)
N2—N3—C8—C9	−0.9 (2)	C11—C12—C13—C14	0.6 (2)
C11—N4—C10—C9	56.44 (17)	C17—C12—C13—C14	−178.83 (16)
C20—N4—C10—C9	−165.14 (13)	C11—C12—C17—C18	−35.1 (2)
C10—N4—C11—C12	−150.96 (13)	C13—C12—C17—C18	144.31 (17)
C10—N4—C11—C16	27.36 (19)	C12—C13—C14—C15	−0.2 (3)
C20—N4—C11—C12	70.09 (15)	C13—C14—C15—C16	−0.3 (3)
C20—N4—C11—C16	−111.60 (15)	C14—C15—C16—C11	0.3 (3)
C10—N4—C20—C19	146.64 (13)	C12—C17—C18—C19	−0.3 (3)
C10—N4—C20—C24	−31.99 (19)	C17—C18—C19—C20	33.4 (2)
C11—N4—C20—C19	−72.97 (16)	C17—C18—C19—C21	−144.41 (17)
C11—N4—C20—C24	108.41 (15)	C18—C19—C20—N4	6.5 (2)
C6—C1—C2—C3	0.8 (2)	C18—C19—C20—C24	−174.85 (15)
C6—C1—C2—C7	−175.74 (16)	C21—C19—C20—N4	−175.64 (13)
C2—C1—C6—C5	0.0 (3)	C21—C19—C20—C24	3.0 (2)
C1—C2—C3—C4	−1.0 (2)	C18—C19—C21—C22	175.63 (16)
C7—C2—C3—C4	175.58 (15)	C20—C19—C21—C22	−2.3 (2)
C1—C2—C7—N1	−119.86 (17)	N4—C20—C24—C23	176.75 (15)
C3—C2—C7—N1	63.67 (18)	C19—C20—C24—C23	−1.9 (2)
C2—C3—C4—C5	0.4 (3)	C19—C21—C22—C23	0.3 (3)
C3—C4—C5—C6	0.4 (3)	C21—C22—C23—C24	0.9 (3)
C4—C5—C6—C1	−0.6 (3)	C22—C23—C24—C20	−0.2 (3)
N3—C8—C9—N1	0.77 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N4	0.97	2.56	3.173 (2)	121

Experimental details

Crystal data
Chemical formula	C₂₄H₂₀N₄
M_r	364.44
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	300
a, b, c (Å)	9.4394 (10), 22.206 (3), 9.4330 (9)
β (°)	107.172 (3)
V (Å³)	1889.1 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.26 × 0.23 × 0.20

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22703, 3711, 2982
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.01
No. of reflections	3711
No. of parameters	253
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.23

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7A···N4	0.97	2.56	3.173 (2)	121

Acknowledgements

We thank Professor T. N. Guru Row and Vijith Kumar, SSCU, IISc, Bangalore, India, for providing facilities for the data collection.

References

Abdoh, M. M. M., Madan Kumar, S., Vinay Kumar, K. S., Manjunath, B. C., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o17. CSD CrossRef IUCr Journals Google Scholar
Bruker (2005). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Macrae, C. F., Edgington, P. R., McCabe, P., Pidcock, E., Shields, G. P., Taylor, R., Towler, M. & van de Streek, J. (2006). J. Appl. Cryst. 39, 453–457. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar