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

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

doi:10.1107/S1600536813030547

organic compounds

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ISSN: 2056-9890

Volume 69| Part 12| December 2013| Page o1763

doi:10.1107/S1600536813030547

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5-[(1-Benzyl-1H-1,2,3-triazol-4-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 5 November 2013; accepted 7 November 2013; online 13 November 2013)

In the title compound, C₂₄H₂₀N₄, the azepine ring adopts a boat conformation. The dihedral angle between the benzene rings fused to the azepine ring is 49.40 (9)°. The triazole ring makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring. In the crystal, molecules are linked via C—H⋯π interactions and a parallel slipped π–π interaction [centroid–centroid distance = 3.7324 (9), normal distance = 3.4060 (6) and slippage = 1.526 Å], forming a three-dimensional network.

CCDC reference: 970672

Related literature

For the use of dibenzo azepine derivatives in the preparation of carbamazepine, see: Rockliff & Davis (1966 ). For their antitumor properties, see: Al-Qawasmeh et al. (2009 ). For related structures, see: Abdoh et al. (2013 ); Manjunath et al. (2013 ). For ring-puckering analysis, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₄H₂₀N₄
M_r = 364.44
Monoclinic, P 2₁ /c
a = 11.4339 (10) Å
b = 11.7140 (12) Å
c = 14.4527 (13) Å
β = 98.610 (4)°
V = 1913.9 (3) Å³
Z = 4
Cu Kα radiation
μ = 0.60 mm⁻¹
T = 296 K
0.23 × 0.22 × 0.21 mm

Data collection

Bruker X8 Proteum diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2013 ) T_min = 0.871, T_max = 0.882
11434 measured reflections
3160 independent reflections
2742 reflections with I > 2σ(I)
R_int = 0.029

Refinement

R[F² > 2σ(F²)] = 0.047
wR(F²) = 0.135
S = 1.06
3160 reflections
242 parameters
H-atom parameters constrained
Δρ_max = 0.37 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯Cg2ⁱ	0.97	2.83	3.600 (2)	137
C20—H20⋯Cg1ⁱ	0.93	2.79	3.642 (2)	153
Symmetry code: (i) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); 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., 2008 ); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Supporting information

CCDC reference: 970672

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536813030547/su2664sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813030547/su2664Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813030547/su2664Isup3.cml

checkCIF report

Comment top

Dibenzo azepine derivatives have been shown to act as antitumor drugs (Al-Qawasmeh et al., 2009). They are used in the prepration of carbamazepine, an anticonvulsant (Rockliff & Davis, 1966). As a part of our on-going research on the synthesis and crystal structural studies of dibenzo azepine derivatives (Abdoh et al., 2013; Manjunath et al., 2013), we present herein the crystal structure of the title compound.

The molecular structure of the title molecule is shown in Fig. 1. The seven-membered azepine ring adopts a boat conformation with puckering parameters (Cremer & Pople, 1975): Q₂ = 0.6845 (18) Å, Q3 = 0.2069 (17) Å, ϕ₂ = 178.28 (16)°, ϕ₃ = 178.9 (5)°, and a total puckering amplitude Q_T = 0.7149 (17) Å .

The dihedral angle between the two benzene rings, (C1—C6) and (C9—C14), fused to the azepine ring is 49.40 (9)°. The triazole ring (C16/N2—N4/C17) makes a dihedral angle of 77.88 (9)° with the terminal phenyl ring (C19—C24). The overall geometry of the title molecule is similar that of earlier reported structures (Abdoh et al., 2013; Manjunath et al., 2013).

In the crystal, molecules are connected by C—H···π interactions (Table 1), and a slipped parallel π-π interaction involving inversion related terminal phenyl rings [Cg3···Cg3ⁱ = 3.7324 (9) Å; normal distance = 3.4060 (6) Å; slippage = 1.526 Å; Cg3 is the centroid of ring (C20—C24); symmetry code: (i) = -x + 2, -y + 1, -z + 2]. These interactions result in the formation of a three-dimensional structure (Fig. 2).

Related literature top

For the use of dibenzo azepine derivatives in the preparation of carbamazepine, see: Rockliff & Davis (1966). For their antitumor properties, see: Al-Qawasmeh et al. (2009). For related structures, see: Abdoh et al. (2013); Manjunath et al. (2013). For ring-puckering analysis, see: Cremer & Pople (1975).

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. The resulting reaction mixture was stirred for 6 h. After completion of the reaction (monitored by TLC), the reaction mixture was diluted with water (50 ml). The aqueous layer was extracted with ethyl acetate (3 × 20 ml), the combined ethyl acetate layer was washed with brine solution (2 × 25 ml). The organic layer was then dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The crude product obtained was purified by column chromatography over silica gel (60–120 mesh) using hexane:ethyl acetate (8:2) as eluent. The pure compound was recrystallized in ethyl acetate/hexane (1:1) to obtain light-yellow block-like crystals.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008); software used to prepare material for publication: Mercury (Macrae et al., 2008).

Figures top

	Fig. 1. A view of the molecular structure of the title molecule, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. A viewed along the b axis of the crystal packing of the title compound.

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

Crystal data top

C₂₄H₂₀N₄	F(000) = 768
M_r = 364.44	D_x = 1.265 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
Hall symbol: -P 2ybc	Cell parameters from 3160 reflections
a = 11.4339 (10) Å	θ = 3.9–64.7°
b = 11.7140 (12) Å	µ = 0.60 mm⁻¹
c = 14.4527 (13) Å	T = 296 K
β = 98.610 (4)°	Block, yellow
V = 1913.9 (3) Å³	0.23 × 0.22 × 0.21 mm
Z = 4

Data collection top

Bruker X8 Proteum diffractometer	3160 independent reflections
Radiation source: Bruker MicroStar microfocus rotating anode	2742 reflections with I > 2σ(I)
Helios multilayer optics monochromator	R_int = 0.029
Detector resolution: 10.7 pixels mm^-1	θ_max = 64.7°, θ_min = 3.9°
ϕ and ω scans	h = −13→13
Absorption correction: multi-scan (SADABS; Bruker, 2013)	k = −6→13
T_min = 0.871, T_max = 0.882	l = −16→16
11434 measured reflections

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)] = 0.047	H-atom parameters constrained
wR(F²) = 0.135	w = 1/[σ²(F_o²) + (0.0672P)² + 0.668P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
3160 reflections	Δρ_max = 0.37 e Å⁻³
242 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0022 (4)

Crystal data top

C₂₄H₂₀N₄	V = 1913.9 (3) Å³
M_r = 364.44	Z = 4
Monoclinic, P2₁/c	Cu Kα radiation
a = 11.4339 (10) Å	µ = 0.60 mm⁻¹
b = 11.7140 (12) Å	T = 296 K
c = 14.4527 (13) Å	0.23 × 0.22 × 0.21 mm
β = 98.610 (4)°

Data collection top

Bruker X8 Proteum diffractometer	3160 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2013)	2742 reflections with I > 2σ(I)
T_min = 0.871, T_max = 0.882	R_int = 0.029
11434 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.047	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.06	Δρ_max = 0.37 e Å⁻³
3160 reflections	Δρ_min = −0.35 e Å⁻³
242 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 esds are taken into account in the estimation of distances, angles and torsion angles

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 > 2sigma(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	0.43569 (11)	0.09444 (13)	0.81026 (9)	0.0380 (4)
N2	0.75967 (14)	0.07129 (16)	0.84538 (13)	0.0587 (6)
N3	0.83816 (14)	0.15341 (17)	0.84788 (13)	0.0615 (6)
N4	0.78072 (13)	0.25199 (14)	0.84990 (10)	0.0466 (5)
C1	0.42570 (14)	0.13226 (14)	0.71500 (11)	0.0362 (5)
C2	0.50035 (15)	0.09093 (17)	0.65474 (12)	0.0444 (6)
C3	0.49640 (18)	0.13523 (19)	0.56554 (13)	0.0529 (7)
C4	0.41693 (18)	0.22002 (19)	0.53381 (13)	0.0552 (7)
C5	0.34204 (17)	0.26084 (17)	0.59263 (13)	0.0493 (6)
C6	0.34446 (15)	0.21923 (15)	0.68381 (12)	0.0397 (5)
C7	0.26469 (16)	0.26982 (16)	0.74219 (13)	0.0472 (6)
C8	0.21604 (16)	0.21843 (17)	0.80959 (14)	0.0502 (6)
C9	0.22998 (15)	0.10011 (17)	0.83926 (12)	0.0434 (6)
C10	0.33367 (14)	0.03702 (16)	0.83579 (11)	0.0390 (5)
C11	0.33787 (16)	−0.07699 (17)	0.86185 (13)	0.0486 (6)
C12	0.24221 (19)	−0.1295 (2)	0.89303 (15)	0.0606 (8)
C13	0.14115 (19)	−0.0676 (2)	0.89868 (16)	0.0654 (8)
C14	0.13561 (18)	0.0451 (2)	0.87236 (14)	0.0577 (7)
C15	0.54828 (15)	0.04203 (17)	0.85030 (13)	0.0450 (6)
C16	0.65211 (14)	0.11824 (16)	0.84764 (11)	0.0404 (6)
C17	0.66473 (15)	0.23304 (17)	0.85105 (13)	0.0473 (6)
C18	0.84716 (19)	0.3590 (2)	0.86075 (13)	0.0559 (7)
C19	0.86839 (10)	0.39520 (10)	0.96072 (6)	0.0391 (5)
C20	0.78941 (10)	0.47031 (11)	0.99293 (9)	0.0577 (7)
C21	0.80418 (14)	0.50082 (13)	1.08690 (11)	0.0767 (10)
C22	0.89793 (16)	0.45624 (15)	1.14866 (7)	0.0805 (10)
C23	0.97691 (13)	0.38113 (14)	1.11645 (8)	0.0791 (9)
C24	0.96214 (10)	0.35062 (11)	1.02248 (9)	0.0527 (7)
H2	0.55350	0.03280	0.67480	0.0530*
H3	0.54780	0.10750	0.52670	0.0630*
H4	0.41380	0.24930	0.47370	0.0660*
H5	0.28820	0.31780	0.57110	0.0590*
H7	0.24560	0.34630	0.73130	0.0570*
H8	0.16780	0.26350	0.84110	0.0600*
H11	0.40610	−0.11910	0.85840	0.0580*
H12	0.24630	−0.20610	0.91000	0.0730*
H13	0.07700	−0.10200	0.92020	0.0790*
H14	0.06700	0.08620	0.87660	0.0690*
H15A	0.55930	−0.02740	0.81610	0.0540*
H15B	0.54470	0.02110	0.91480	0.0540*
H17	0.60590	0.28730	0.85360	0.0570*
H18A	0.80330	0.41800	0.82330	0.0670*
H18B	0.92240	0.34900	0.83840	0.0670*
H20	0.72670	0.50010	0.95160	0.0690*
H21	0.75130	0.55110	1.10850	0.0920*
H22	0.90780	0.47670	1.21150	0.0970*
H23	1.03960	0.35130	1.15780	0.0950*
H24	1.01500	0.30040	1.00090	0.0630*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0325 (7)	0.0412 (8)	0.0377 (7)	−0.0023 (6)	−0.0028 (5)	0.0018 (6)
N2	0.0383 (8)	0.0599 (11)	0.0768 (12)	−0.0014 (8)	0.0054 (8)	−0.0219 (9)
N3	0.0411 (9)	0.0662 (12)	0.0775 (12)	−0.0055 (8)	0.0101 (8)	−0.0265 (9)
N4	0.0411 (8)	0.0578 (10)	0.0396 (8)	−0.0123 (7)	0.0016 (6)	−0.0084 (7)
C1	0.0342 (8)	0.0356 (9)	0.0361 (8)	−0.0059 (7)	−0.0032 (6)	−0.0037 (7)
C2	0.0399 (9)	0.0466 (11)	0.0447 (10)	−0.0010 (8)	−0.0001 (7)	−0.0063 (8)
C3	0.0518 (11)	0.0648 (14)	0.0422 (10)	−0.0080 (10)	0.0078 (8)	−0.0096 (9)
C4	0.0608 (12)	0.0639 (14)	0.0385 (10)	−0.0142 (10)	−0.0008 (9)	0.0034 (9)
C5	0.0500 (10)	0.0450 (11)	0.0478 (10)	−0.0040 (8)	−0.0091 (8)	0.0054 (8)
C6	0.0386 (9)	0.0344 (9)	0.0431 (9)	−0.0048 (7)	−0.0035 (7)	−0.0015 (7)
C7	0.0455 (10)	0.0356 (10)	0.0584 (11)	0.0037 (8)	0.0011 (8)	−0.0026 (8)
C8	0.0419 (10)	0.0499 (12)	0.0589 (11)	0.0036 (8)	0.0079 (8)	−0.0119 (9)
C9	0.0395 (9)	0.0497 (11)	0.0399 (9)	−0.0034 (8)	0.0028 (7)	−0.0061 (8)
C10	0.0374 (9)	0.0445 (11)	0.0329 (8)	−0.0062 (7)	−0.0018 (6)	−0.0020 (7)
C11	0.0439 (10)	0.0497 (12)	0.0490 (10)	−0.0051 (8)	−0.0038 (8)	0.0070 (8)
C12	0.0601 (13)	0.0582 (14)	0.0602 (12)	−0.0146 (10)	−0.0019 (10)	0.0169 (10)
C13	0.0521 (12)	0.0800 (17)	0.0652 (13)	−0.0177 (11)	0.0120 (10)	0.0137 (12)
C14	0.0428 (11)	0.0732 (15)	0.0582 (12)	−0.0036 (10)	0.0108 (9)	0.0013 (10)
C15	0.0368 (9)	0.0465 (11)	0.0478 (10)	−0.0007 (8)	−0.0066 (7)	0.0048 (8)
C16	0.0347 (9)	0.0487 (11)	0.0351 (9)	−0.0011 (7)	−0.0040 (7)	−0.0034 (7)
C17	0.0356 (9)	0.0521 (12)	0.0521 (10)	0.0000 (8)	−0.0006 (8)	0.0013 (9)
C18	0.0566 (12)	0.0647 (14)	0.0451 (10)	−0.0223 (10)	0.0032 (9)	0.0003 (9)
C19	0.0352 (8)	0.0382 (10)	0.0422 (9)	−0.0097 (7)	0.0005 (7)	0.0027 (7)
C20	0.0457 (11)	0.0518 (13)	0.0753 (14)	−0.0038 (9)	0.0080 (9)	−0.0076 (10)
C21	0.0734 (16)	0.0795 (18)	0.0832 (17)	−0.0254 (14)	0.0317 (14)	−0.0304 (14)
C22	0.107 (2)	0.088 (2)	0.0506 (13)	−0.0487 (17)	0.0250 (13)	−0.0149 (13)
C23	0.0800 (16)	0.0812 (18)	0.0630 (14)	−0.0326 (14)	−0.0319 (12)	0.0246 (13)
C24	0.0437 (10)	0.0481 (12)	0.0618 (12)	−0.0041 (8)	−0.0064 (9)	0.0076 (9)

Geometric parameters (Å, º) top

N1—C1	1.435 (2)	C19—C20	1.3900 (17)
N1—C10	1.442 (2)	C19—C24	1.3900 (16)
N1—C15	1.465 (2)	C20—C21	1.390 (2)
N2—N3	1.312 (3)	C21—C22	1.390 (2)
N2—C16	1.352 (2)	C22—C23	1.390 (2)
N3—N4	1.331 (2)	C23—C24	1.3900 (18)
N4—C17	1.347 (2)	C2—H2	0.9300
N4—C18	1.462 (3)	C3—H3	0.9300
C1—C2	1.394 (2)	C4—H4	0.9300
C1—C6	1.407 (2)	C5—H5	0.9300
C2—C3	1.384 (3)	C7—H7	0.9300
C3—C4	1.378 (3)	C8—H8	0.9300
C4—C5	1.379 (3)	C11—H11	0.9300
C5—C6	1.401 (3)	C12—H12	0.9300
C6—C7	1.458 (3)	C13—H13	0.9300
C7—C8	1.335 (3)	C14—H14	0.9300
C8—C9	1.453 (3)	C15—H15A	0.9700
C9—C10	1.404 (2)	C15—H15B	0.9700
C9—C14	1.401 (3)	C17—H17	0.9300
C10—C11	1.387 (3)	C18—H18A	0.9700
C11—C12	1.388 (3)	C18—H18B	0.9700
C12—C13	1.377 (3)	C20—H20	0.9300
C13—C14	1.373 (3)	C21—H21	0.9300
C15—C16	1.491 (3)	C22—H22	0.9300
C16—C17	1.353 (3)	C23—H23	0.9300
C18—C19	1.490 (2)	C24—H24	0.9300

C1—N1—C10	116.01 (13)	C19—C24—C23	120.00 (12)
C1—N1—C15	116.59 (13)	C1—C2—H2	119.00
C10—N1—C15	113.59 (14)	C3—C2—H2	120.00
N3—N2—C16	108.78 (17)	C2—C3—H3	120.00
N2—N3—N4	107.39 (15)	C4—C3—H3	120.00
N3—N4—C17	110.32 (16)	C3—C4—H4	121.00
N3—N4—C18	119.74 (16)	C5—C4—H4	120.00
C17—N4—C18	129.54 (17)	C4—C5—H5	119.00
N1—C1—C2	121.60 (15)	C6—C5—H5	119.00
N1—C1—C6	119.02 (14)	C6—C7—H7	116.00
C2—C1—C6	119.21 (15)	C8—C7—H7	116.00
C1—C2—C3	120.93 (17)	C7—C8—H8	116.00
C2—C3—C4	120.55 (18)	C9—C8—H8	116.00
C3—C4—C5	118.96 (18)	C10—C11—H11	119.00
C4—C5—C6	122.16 (18)	C12—C11—H11	119.00
C1—C6—C5	118.19 (16)	C11—C12—H12	120.00
C1—C6—C7	123.32 (16)	C13—C12—H12	120.00
C5—C6—C7	118.48 (16)	C12—C13—H13	120.00
C6—C7—C8	127.16 (18)	C14—C13—H13	120.00
C7—C8—C9	127.32 (18)	C9—C14—H14	119.00
C8—C9—C10	123.20 (16)	C13—C14—H14	119.00
C8—C9—C14	118.92 (17)	N1—C15—H15A	109.00
C10—C9—C14	117.88 (18)	N1—C15—H15B	109.00
N1—C10—C9	118.91 (16)	C16—C15—H15A	109.00
N1—C10—C11	121.50 (15)	C16—C15—H15B	109.00
C9—C10—C11	119.49 (16)	H15A—C15—H15B	108.00
C10—C11—C12	121.22 (18)	N4—C17—H17	127.00
C11—C12—C13	119.7 (2)	C16—C17—H17	127.00
C12—C13—C14	119.6 (2)	N4—C18—H18A	110.00
C9—C14—C13	122.1 (2)	N4—C18—H18B	109.00
N1—C15—C16	113.27 (16)	C19—C18—H18A	109.00
N2—C16—C15	119.20 (17)	C19—C18—H18B	109.00
N2—C16—C17	108.23 (16)	H18A—C18—H18B	108.00
C15—C16—C17	132.50 (16)	C19—C20—H20	120.00
N4—C17—C16	105.26 (16)	C21—C20—H20	120.00
N4—C18—C19	110.77 (15)	C20—C21—H21	120.00
C18—C19—C20	119.02 (12)	C22—C21—H21	120.00
C18—C19—C24	120.91 (13)	C21—C22—H22	120.00
C20—C19—C24	120.00 (10)	C23—C22—H22	120.00
C19—C20—C21	120.00 (12)	C22—C23—H23	120.00
C20—C21—C22	120.00 (14)	C24—C23—H23	120.00
C21—C22—C23	120.00 (11)	C19—C24—H24	120.00
C22—C23—C24	120.00 (12)	C23—C24—H24	120.00

C10—N1—C1—C2	−118.27 (18)	C1—C6—C7—C8	−32.0 (3)
C10—N1—C1—C6	66.5 (2)	C5—C6—C7—C8	149.4 (2)
C15—N1—C1—C2	19.7 (2)	C6—C7—C8—C9	−1.0 (3)
C15—N1—C1—C6	−155.60 (16)	C7—C8—C9—C10	31.6 (3)
C1—N1—C10—C9	−68.6 (2)	C7—C8—C9—C14	−147.9 (2)
C1—N1—C10—C11	114.98 (18)	C8—C9—C10—N1	6.2 (3)
C15—N1—C10—C9	152.20 (15)	C8—C9—C10—C11	−177.34 (17)
C15—N1—C10—C11	−24.2 (2)	C14—C9—C10—N1	−174.34 (16)
C1—N1—C15—C16	57.8 (2)	C14—C9—C10—C11	2.1 (3)
C10—N1—C15—C16	−163.24 (14)	C8—C9—C14—C13	177.84 (19)
C16—N2—N3—N4	−1.2 (2)	C10—C9—C14—C13	−1.7 (3)
N3—N2—C16—C15	−176.98 (16)	N1—C10—C11—C12	175.13 (17)
N3—N2—C16—C17	0.4 (2)	C9—C10—C11—C12	−1.2 (3)
N2—N3—N4—C17	1.5 (2)	C10—C11—C12—C13	−0.2 (3)
N2—N3—N4—C18	174.94 (16)	C11—C12—C13—C14	0.8 (3)
N3—N4—C17—C16	−1.3 (2)	C12—C13—C14—C9	0.2 (3)
C18—N4—C17—C16	−173.84 (16)	N1—C15—C16—N2	−153.38 (16)
N3—N4—C18—C19	−95.86 (19)	N1—C15—C16—C17	30.0 (3)
C17—N4—C18—C19	76.1 (2)	N2—C16—C17—N4	0.5 (2)
N1—C1—C2—C3	−174.45 (17)	C15—C16—C17—N4	177.41 (17)
C6—C1—C2—C3	0.8 (3)	N4—C18—C19—C20	−93.75 (18)
N1—C1—C6—C5	175.42 (16)	N4—C18—C19—C24	83.06 (19)
N1—C1—C6—C7	−3.2 (3)	C18—C19—C20—C21	176.83 (15)
C2—C1—C6—C5	0.1 (2)	C24—C19—C20—C21	−0.02 (19)
C2—C1—C6—C7	−178.55 (17)	C18—C19—C24—C23	−176.77 (15)
C1—C2—C3—C4	−1.1 (3)	C20—C19—C24—C23	0.0 (2)
C2—C3—C4—C5	0.6 (3)	C19—C20—C21—C22	0.0 (2)
C3—C4—C5—C6	0.3 (3)	C20—C21—C22—C23	0.0 (2)
C4—C5—C6—C1	−0.6 (3)	C21—C22—C23—C24	0.0 (2)
C4—C5—C6—C7	178.08 (18)	C22—C23—C24—C19	0.0 (2)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cg2ⁱ	0.97	2.83	3.600 (2)	137
C20—H20···Cg1ⁱ	0.93	2.79	3.642 (2)	153

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

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C1–C6 and C9–C14 rings, respectively

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cg2ⁱ	0.97	2.83	3.600 (2)	137
C20—H20···Cg1ⁱ	0.93	2.79	3.642 (2)	153

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

Acknowledgements

We are grateful to the IOE, University of Mysore, for providing the single-crystal X-ray diffraction facility.

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
Al-Qawasmeh, R. A., Lee, Y., Cao, M.-Y., Gu, X., Viau, S., Lightfoot, J., Wright, J. A. & Young, A. H. (2009). Bioorg. Med. Chem., 19 104–107. Google Scholar
Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354–1358. CrossRef CAS Web of Science Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CrossRef CAS IUCr Journals Google Scholar
Manjunath, B. C., Vinay Kumar, K. S., Madan Kumar, S., Sadashiva, M. P. & Lokanath, N. K. (2013). Acta Cryst. E69, o1233. CSD CrossRef IUCr Journals Google Scholar
Rockliff, B. W. & Davis, E. H. (1966). Arch. Neurol. 15, 129–136. CrossRef CAS PubMed Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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