Crystal structure of (E)-N-(3,3-di­phenyl­allyl­idene)-9-ethyl-9H-carbazol-3-amine

Thirumurthy, K.; Thirunarayanan, G.; Murugavel, S.

doi:10.1107/S2056989015005770

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ISSN: 2056-9890

Volume 71| Part 4| April 2015| Pages 418-420

doi:10.1107/S2056989015005770

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Crystal structure of (E)-N-(3,3-diphenylallylidene)-9-ethyl-9H-carbazol-3-amine

Kannan Thirumurthy,^a Ganesamoorthy Thirunarayanan ^a ^* and S. Murugavel ^b ^*

^aDepartment of Chemistry, Annamalai University, Annamalainagar 608 002, Chidambaram, Tamilnadu, India, and ^bDepartment of Physics, Thanthai Periyar Government Institute of Technology, Vellore 632 002, India
^*Correspondence e-mail: drgtnarayanan@rediffmail.com, smurugavel27@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 16 March 2015; accepted 22 March 2015; online 28 March 2015)

In the title compound, C₂₉H₂₄N₂, the C=N bond of the central imine group adopts an E conformation. The dihedral angles between the mean plane of the essentially planar carbazole ring system [r.m.s. deviation = 0.039 (2) Å] and the two phenyl rings of the 3,3-diphenylallylidene unit are 75.9 (1) and 64.6 (1)°. In the crystal, molecules are linked by C—H⋯π interactions, forming a three-dimensional supramolecular network.

Keywords: crystal structure; carbazole; 9-ethyl-9H-carbazol-3-amine; C—H⋯π interactions.

CCDC reference: 967497

1. Chemical context

Carbazole and its derivatives have become quite attractive compounds owing to their applications in pharmacy and molecular electronics. It has been reported that carbazole derivatives possess various biological activities, such as antitumor (Itoigawa et al., 2000 ), anti-oxidative (Tachibana et al., 2001 ), anti-inflammatory and antimutagenic (Ramsewak et al., 1999 ). Carbazole derivatives also exhibit electroactivity and luminescence properties and are considered to be potential candidates for electronic devices such as colour displays, organic semiconductor lasers and solar cells (Friend et al., 1999 ). These compounds are thermally and photochemically stable, which makes them useful materials for technological applications. For instance, the carbazole ring is easily funtionalized and covalently linked to other molecules (Díaz et al., 2002 ). This enables its use as a convenient building block for the design and synthesis of molecular glasses, which are widely studied as components of electroactive and photoactive materials (Zhang et al., 2004 ). Against this background, and in order to obtain detailed information on molecular conformations in the solid state, X-ray studies of the title compound have been carried out.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The C15=N2 bond of the central imine group adopts an E conformation. The carbazole ring system (N1/C1–C12) is essentially planar [maximum deviation = 0.039 (2) Å for atom C9]. The phenyl rings C18–C23 and C24–C29 of the (3,3-diphenylallylidene) unit are oriented at dihedral angles of 75.9 (1) and 64.6 (1)°, respectively, to the mean plane of the carbazole ring system. The dihedral angle between the two phenyl rings is 76.1 (1)°. The sum of the bond angles around atom N1 (359.7°) of the pyrrole ring is in accordance with sp² hybridization. The geometric parameters of the title molecule agree well with those reported for similar structures (Murugavel et al., 2009 ; Archana et al., 2011 ).

Figure 1
Molecular structure of the title compound with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level.

3. Supramolecular features

In the crystal, molecules are linked by six intermolecular C—H⋯π interactions, forming a three-dimensional supramolecular network (Table 1 and Fig. 2). Four of these interactions involves a benzene H atom of the carbazole ring system and a benzene ring of an adjacent molecule, viz. C7—H7⋯Cg1ⁱ, C11—H11⋯Cg3ⁱⁱ, C20—H20⋯Cg4^iv, and C29—H29⋯Cg3^v. The other two involve a benzene H atom of the carbazole ring system and the pyrrole ring of an adjacent molecule (C8—H8⋯Cg2ⁱ), and a methylene H atom of the ethyl group and a benzene ring of an adjacent molecule (C13—H13A⋯Cg1ⁱⁱⁱ); see Table 1 and Fig. 2 for full details.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg2, Cg3 and Cg4 are the centroids of rings C3/C4/C9–C12, N1/C1–C4, C18–C23 and C1/C2/C5–C8, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C7—H7⋯Cg1ⁱ	0.93	2.92	3.647 (2)	136
C8—H8⋯Cg2ⁱ	0.93	2.98	3.777 (2)	145
C11—H11⋯Cg3ⁱⁱ	0.93	2.85	3.551 (2)	133
C13—H13A⋯Cg1ⁱⁱⁱ	0.97	3.00	3.749 (2)	135
C20—H20⋯Cg4^iv	0.93	2.62	3.498 (2)	157
C29—H29⋯Cg3^v	0.93	2.87	3.796 (3)	175
Symmetry codes: (i) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) -x, -y+2, -z; (iii) -x+1, -y+2, -z; (iv) x-1, y, z; (v) -x, -y+1, -z.

Figure 2
A partial view along the b axis of the crystal packing of the title compound, showing the intermolecular C—H⋯π interactions (see Table 1

for details), forming a three-dimensional supramolecular network. H atoms not involved in these interactions have been omitted for clarity.

4. Synthesis and crystallization

A 25 ml round-bottom flask was charged with 9-ethyl-9H-carbazol-3-amine (1 mmol), 3,3-diphenylacrylaldehyde (1 mmol) and sulfated SnO₂-Bi₂O₃-fly ash catalyst (20 mg) in water (15 ml) and the mixture was refluxed at 363 K for 1h. On completion of the reaction (monitored by TLC with ethyl acetate and hexane as an eluent 20%) the mixture was cooled to ambient temperature. Dichloromethane (20 ml) was then added to separate the organic and aqueous layers. The organic layer was filtered, dried on anhydrous Na₂SO₄ and the solvent removed using a rotary evaporator. The crude product obtained was purified by column chromatography on silica gel (200 mesh) with hexane and ethyl acetate (4:1) as eluent, to afford the title compound in good yield (93%). Red crystals suitable for X-ray diffraction analysis were obtained after recrystallization in CH₂Cl₂.

5. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. H atoms were positioned geometrically and constrained to ride on their parent atom with C—H = 0.93–0.97 Å and with U_iso(H) = 1.5U_eq for methyl H atoms and 1.2U_eq(C) for other H atoms.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₉H₂₄N₂
M_r	400.50
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	13.6502 (17), 8.7616 (13), 18.224 (2)
β (°)	92.234 (11)
V (Å³)	2177.9 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.07
Crystal size (mm)	0.23 × 0.21 × 0.15

Data collection
Diffractometer	Bruker SMART CCD area detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996 )
T_min, T_max	0.984, 0.989
No. of measured, independent and observed [I > 2σ(I)] reflections	9709, 4982, 3066
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.688

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.056, 0.150, 1.03
No. of reflections	4982
No. of parameters	280
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.17, −0.19
Computer programs: SMART and SAINT (Bruker, 2002 ), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows (Farrugia (2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 967497

Crystal structure: contains datablocks global, I. DOI: 10.1107/S2056989015005770/su5095sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2056989015005770/su5095Isup2.hkl

checkCIF report

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia (2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

(E)-N-(3,3-Diphenylallylidene)-9-ethyl-9H-carbazol-3-amine top

Crystal data top

C₂₉H₂₄N₂	F(000) = 848
M_r = 400.50	D_x = 1.221 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5927 reflections
a = 13.6502 (17) Å	θ = 2.8–29.3°
b = 8.7616 (13) Å	µ = 0.07 mm⁻¹
c = 18.224 (2) Å	T = 293 K
β = 92.234 (11)°	Block, red
V = 2177.9 (5) Å³	0.23 × 0.21 × 0.15 mm
Z = 4

Data collection top

Bruker SMART CCD area-detector diffractometer	4982 independent reflections
Radiation source: fine-focus sealed tube	3066 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
φ and ω scans	θ_max = 29.3°, θ_min = 2.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −15→18
T_min = 0.984, T_max = 0.989	k = −11→11
9709 measured reflections	l = −24→23

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)] = 0.056	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.150	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0555P)² + 0.1709P] where P = (F_o² + 2F_c²)/3
4982 reflections	(Δ/σ)_max < 0.001
280 parameters	Δρ_max = 0.17 e Å⁻³
0 restraints	Δρ_min = −0.19 e Å⁻³

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 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
C14	0.5899 (2)	1.3222 (3)	0.14013 (13)	0.0822 (7)
H14A	0.6192	1.4132	0.1215	0.123*
H14B	0.6144	1.3041	0.1894	0.123*
H14C	0.5200	1.3346	0.1399	0.123*
N2	0.19996 (10)	0.8129 (2)	0.10030 (8)	0.0516 (4)
C10	0.29431 (12)	0.8778 (2)	0.09957 (9)	0.0454 (4)
C9	0.36711 (12)	0.8093 (2)	0.14234 (9)	0.0449 (4)
H9	0.3538	0.7226	0.1696	0.054*
C4	0.47794 (13)	1.0054 (2)	0.10553 (9)	0.0462 (4)
C3	0.46026 (12)	0.8713 (2)	0.14420 (9)	0.0427 (4)
N1	0.57338 (11)	1.04985 (18)	0.11800 (8)	0.0530 (4)
C12	0.40455 (14)	1.0746 (2)	0.06391 (10)	0.0530 (5)
H12	0.4166	1.1636	0.0380	0.064*
C11	0.31382 (14)	1.0100 (2)	0.06153 (10)	0.0518 (5)
H11	0.2636	1.0560	0.0336	0.062*
C19	−0.16510 (13)	0.7140 (2)	0.04772 (10)	0.0533 (5)
H19	−0.1369	0.7691	0.0867	0.064*
C15	0.14631 (13)	0.8153 (2)	0.04164 (10)	0.0529 (5)
H15	0.1714	0.8548	−0.0011	0.063*
C2	0.55154 (13)	0.8316 (2)	0.18155 (9)	0.0455 (4)
C18	−0.11167 (13)	0.6882 (2)	−0.01430 (10)	0.0471 (4)
C1	0.61869 (13)	0.9460 (2)	0.16451 (10)	0.0510 (5)
C16	0.04842 (13)	0.7586 (3)	0.04026 (10)	0.0553 (5)
H16	0.0230	0.7319	0.0851	0.066*
C23	−0.15719 (14)	0.6089 (2)	−0.07131 (11)	0.0588 (5)
H23	−0.1235	0.5911	−0.1139	0.071*
C20	−0.25842 (14)	0.6598 (3)	0.05254 (12)	0.0614 (6)
H20	−0.2930	0.6772	0.0947	0.074*
C24	0.02709 (12)	0.7604 (2)	−0.09425 (9)	0.0477 (5)
C13	0.61468 (15)	1.1902 (2)	0.09293 (11)	0.0614 (5)
H13A	0.5906	1.2099	0.0430	0.074*
H13B	0.6854	1.1800	0.0923	0.074*
C8	0.58185 (14)	0.7119 (2)	0.22603 (10)	0.0550 (5)
H8	0.5385	0.6343	0.2374	0.066*
C29	0.10181 (14)	0.6715 (3)	−0.11811 (11)	0.0592 (5)
H29	0.1314	0.6011	−0.0862	0.071*
C28	0.13409 (15)	0.6844 (3)	−0.18854 (13)	0.0714 (7)
H28	0.1846	0.6220	−0.2037	0.086*
C5	0.71384 (14)	0.9426 (3)	0.19254 (11)	0.0666 (6)
H5	0.7580	1.0194	0.1817	0.080*
C22	−0.25053 (16)	0.5561 (3)	−0.06653 (13)	0.0688 (6)
H22	−0.2800	0.5034	−0.1058	0.083*
C25	−0.01406 (15)	0.8636 (3)	−0.14288 (11)	0.0639 (6)
H25	−0.0655	0.9249	−0.1284	0.077*
C21	−0.30082 (16)	0.5802 (3)	−0.00460 (13)	0.0675 (6)
H21	−0.3641	0.5423	−0.0012	0.081*
C27	0.09292 (18)	0.7869 (3)	−0.23570 (12)	0.0767 (7)
H27	0.1145	0.7952	−0.2833	0.092*
C6	0.74105 (16)	0.8237 (3)	0.23656 (12)	0.0746 (7)
H6	0.8050	0.8196	0.2560	0.089*
C26	0.01946 (18)	0.8779 (3)	−0.21270 (12)	0.0784 (7)
H26	−0.0083	0.9503	−0.2445	0.094*
C7	0.67657 (16)	0.7091 (3)	0.25318 (11)	0.0699 (6)
H7	0.6977	0.6289	0.2832	0.084*
C17	−0.00988 (13)	0.7403 (2)	−0.01930 (9)	0.0478 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C14	0.116 (2)	0.0536 (15)	0.0788 (15)	−0.0230 (14)	0.0288 (14)	−0.0040 (12)
N2	0.0456 (9)	0.0658 (12)	0.0433 (8)	0.0018 (8)	−0.0019 (7)	−0.0031 (8)
C10	0.0456 (10)	0.0533 (12)	0.0372 (9)	0.0019 (8)	0.0004 (7)	−0.0053 (8)
C9	0.0533 (11)	0.0435 (11)	0.0377 (9)	−0.0022 (8)	−0.0017 (8)	−0.0005 (8)
C4	0.0522 (11)	0.0419 (11)	0.0444 (9)	0.0002 (8)	0.0019 (8)	−0.0038 (8)
C3	0.0499 (10)	0.0401 (10)	0.0380 (9)	0.0004 (8)	−0.0001 (7)	−0.0022 (8)
N1	0.0532 (9)	0.0478 (10)	0.0578 (9)	−0.0083 (8)	0.0017 (7)	−0.0004 (8)
C12	0.0614 (12)	0.0441 (12)	0.0535 (11)	0.0019 (9)	0.0023 (9)	0.0054 (9)
C11	0.0568 (11)	0.0526 (12)	0.0455 (10)	0.0101 (9)	−0.0034 (8)	0.0013 (9)
C19	0.0526 (11)	0.0567 (13)	0.0504 (10)	0.0044 (9)	−0.0021 (8)	0.0045 (9)
C15	0.0484 (10)	0.0683 (14)	0.0418 (10)	0.0015 (9)	−0.0006 (8)	−0.0023 (9)
C2	0.0482 (10)	0.0488 (11)	0.0393 (9)	0.0001 (8)	0.0002 (7)	−0.0041 (8)
C18	0.0471 (10)	0.0461 (11)	0.0474 (10)	0.0048 (8)	−0.0057 (8)	0.0054 (8)
C1	0.0532 (11)	0.0524 (12)	0.0472 (10)	−0.0032 (9)	−0.0009 (8)	−0.0064 (9)
C16	0.0472 (10)	0.0735 (15)	0.0451 (10)	0.0008 (10)	−0.0007 (8)	0.0036 (10)
C23	0.0559 (12)	0.0603 (14)	0.0596 (12)	0.0007 (10)	−0.0046 (9)	−0.0024 (10)
C20	0.0531 (12)	0.0642 (15)	0.0671 (13)	0.0050 (10)	0.0057 (10)	0.0154 (11)
C24	0.0446 (10)	0.0522 (12)	0.0459 (10)	0.0039 (9)	−0.0039 (8)	−0.0050 (9)
C13	0.0704 (13)	0.0566 (14)	0.0584 (12)	−0.0141 (11)	0.0164 (10)	0.0004 (10)
C8	0.0571 (11)	0.0621 (14)	0.0456 (10)	0.0048 (10)	0.0005 (8)	0.0032 (9)
C29	0.0545 (12)	0.0603 (14)	0.0626 (12)	0.0056 (10)	0.0008 (9)	−0.0078 (10)
C28	0.0530 (12)	0.0880 (19)	0.0741 (15)	−0.0027 (12)	0.0132 (11)	−0.0268 (14)
C5	0.0539 (12)	0.0804 (17)	0.0649 (13)	−0.0121 (11)	−0.0057 (10)	−0.0085 (12)
C22	0.0697 (14)	0.0616 (15)	0.0738 (14)	−0.0076 (11)	−0.0155 (12)	−0.0035 (12)
C25	0.0635 (13)	0.0712 (15)	0.0568 (12)	0.0143 (11)	−0.0012 (10)	0.0049 (11)
C21	0.0553 (12)	0.0585 (15)	0.0879 (16)	−0.0069 (10)	−0.0070 (12)	0.0194 (13)
C27	0.0734 (15)	0.108 (2)	0.0490 (12)	−0.0204 (15)	0.0074 (11)	−0.0124 (13)
C6	0.0600 (13)	0.101 (2)	0.0610 (13)	0.0021 (13)	−0.0172 (11)	−0.0034 (14)
C26	0.0879 (17)	0.092 (2)	0.0542 (13)	0.0018 (15)	−0.0057 (12)	0.0154 (13)
C7	0.0667 (14)	0.0886 (18)	0.0534 (12)	0.0103 (13)	−0.0094 (10)	0.0095 (12)
C17	0.0488 (10)	0.0488 (12)	0.0454 (10)	0.0066 (9)	−0.0037 (8)	0.0012 (9)

Geometric parameters (Å, º) top

C14—C13	1.488 (3)	C18—C23	1.378 (3)
N2—C15	1.272 (2)	C18—C17	1.469 (2)
N2—C10	1.408 (2)	C1—C5	1.377 (3)
C10—C9	1.376 (2)	C16—C17	1.330 (2)
C10—C11	1.381 (3)	C23—C22	1.361 (3)
C9—C3	1.382 (2)	C20—C21	1.364 (3)
C4—N1	1.370 (2)	C24—C29	1.367 (3)
C4—C12	1.374 (2)	C24—C25	1.371 (3)
C4—C3	1.396 (3)	C24—C17	1.485 (2)
C3—C2	1.439 (2)	C8—C7	1.367 (3)
N1—C1	1.374 (2)	C29—C28	1.378 (3)
N1—C13	1.435 (2)	C28—C27	1.351 (3)
C12—C11	1.361 (3)	C5—C6	1.358 (3)
C19—C20	1.365 (3)	C22—C21	1.360 (3)
C19—C18	1.387 (3)	C25—C26	1.375 (3)
C15—C16	1.425 (2)	C27—C26	1.360 (3)
C2—C8	1.379 (3)	C6—C7	1.377 (3)
C2—C1	1.401 (3)

C15—N2—C10	118.81 (16)	N1—C1—C5	129.66 (19)
C9—C10—C11	120.03 (17)	N1—C1—C2	109.14 (15)
C9—C10—N2	117.33 (17)	C5—C1—C2	121.20 (19)
C11—C10—N2	122.53 (16)	C17—C16—C15	125.96 (18)
C10—C9—C3	119.10 (17)	C22—C23—C18	121.2 (2)
N1—C4—C12	129.36 (18)	C21—C20—C19	119.9 (2)
N1—C4—C3	109.73 (15)	C29—C24—C25	117.50 (18)
C12—C4—C3	120.90 (17)	C29—C24—C17	120.63 (17)
C9—C3—C4	119.69 (16)	C25—C24—C17	121.82 (17)
C9—C3—C2	134.08 (17)	N1—C13—C14	112.39 (17)
C4—C3—C2	106.19 (16)	C7—C8—C2	119.0 (2)
C4—N1—C1	108.43 (15)	C24—C29—C28	121.3 (2)
C4—N1—C13	125.00 (17)	C27—C28—C29	120.4 (2)
C1—N1—C13	126.23 (16)	C6—C5—C1	117.9 (2)
C11—C12—C4	118.49 (18)	C21—C22—C23	120.3 (2)
C12—C11—C10	121.74 (17)	C24—C25—C26	121.0 (2)
C20—C19—C18	121.14 (19)	C22—C21—C20	120.0 (2)
N2—C15—C16	121.17 (18)	C28—C27—C26	119.2 (2)
C8—C2—C1	119.35 (17)	C5—C6—C7	121.8 (2)
C8—C2—C3	134.14 (18)	C27—C26—C25	120.5 (2)
C1—C2—C3	106.50 (16)	C8—C7—C6	120.7 (2)
C23—C18—C19	117.43 (18)	C16—C17—C18	121.61 (17)
C23—C18—C17	120.66 (17)	C16—C17—C24	121.49 (17)
C19—C18—C17	121.91 (16)	C18—C17—C24	116.75 (15)

C15—N2—C10—C9	−145.48 (18)	N2—C15—C16—C17	−172.1 (2)
C15—N2—C10—C11	38.4 (3)	C19—C18—C23—C22	−0.9 (3)
C11—C10—C9—C3	−2.6 (3)	C17—C18—C23—C22	178.05 (19)
N2—C10—C9—C3	−178.80 (15)	C18—C19—C20—C21	−0.7 (3)
C10—C9—C3—C4	2.9 (2)	C4—N1—C13—C14	79.5 (2)
C10—C9—C3—C2	179.98 (18)	C1—N1—C13—C14	−93.1 (2)
N1—C4—C3—C9	177.03 (15)	C1—C2—C8—C7	0.8 (3)
C12—C4—C3—C9	−1.8 (3)	C3—C2—C8—C7	180.0 (2)
N1—C4—C3—C2	−0.8 (2)	C25—C24—C29—C28	−0.5 (3)
C12—C4—C3—C2	−179.66 (16)	C17—C24—C29—C28	177.20 (19)
C12—C4—N1—C1	178.78 (19)	C24—C29—C28—C27	0.7 (3)
C3—C4—N1—C1	0.1 (2)	N1—C1—C5—C6	−178.4 (2)
C12—C4—N1—C13	5.1 (3)	C2—C1—C5—C6	0.8 (3)
C3—C4—N1—C13	−173.63 (17)	C18—C23—C22—C21	−0.4 (3)
N1—C4—C12—C11	−178.20 (17)	C29—C24—C25—C26	−0.6 (3)
C3—C4—C12—C11	0.4 (3)	C17—C24—C25—C26	−178.3 (2)
C4—C12—C11—C10	−0.1 (3)	C23—C22—C21—C20	1.2 (3)
C9—C10—C11—C12	1.2 (3)	C19—C20—C21—C22	−0.6 (3)
N2—C10—C11—C12	177.20 (17)	C29—C28—C27—C26	0.3 (3)
C10—N2—C15—C16	−176.66 (18)	C1—C5—C6—C7	0.0 (3)
C9—C3—C2—C8	4.6 (3)	C28—C27—C26—C25	−1.4 (4)
C4—C3—C2—C8	−178.0 (2)	C24—C25—C26—C27	1.6 (4)
C9—C3—C2—C1	−176.15 (19)	C2—C8—C7—C6	0.0 (3)
C4—C3—C2—C1	1.23 (19)	C5—C6—C7—C8	−0.5 (4)
C20—C19—C18—C23	1.4 (3)	C15—C16—C17—C18	−176.78 (19)
C20—C19—C18—C17	−177.52 (18)	C15—C16—C17—C24	7.9 (3)
C4—N1—C1—C5	−179.9 (2)	C23—C18—C17—C16	−152.0 (2)
C13—N1—C1—C5	−6.3 (3)	C19—C18—C17—C16	26.9 (3)
C4—N1—C1—C2	0.8 (2)	C23—C18—C17—C24	23.6 (3)
C13—N1—C1—C2	174.34 (17)	C19—C18—C17—C24	−157.54 (18)
C8—C2—C1—N1	178.13 (16)	C29—C24—C17—C16	59.9 (3)
C3—C2—C1—N1	−1.2 (2)	C25—C24—C17—C16	−122.5 (2)
C8—C2—C1—C5	−1.3 (3)	C29—C24—C17—C18	−115.7 (2)
C3—C2—C1—C5	179.36 (17)	C25—C24—C17—C18	61.9 (3)

Hydrogen-bond geometry (Å, º) top

Cg1, Cg2, Cg3 and Cg4 are the centroids of rings C3/C4/C9–C12, N1/C1–C4, C18–C23 and C1/C2/C5–C8, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
C7—H7···Cg1ⁱ	0.93	2.92	3.647 (2)	136
C8—H8···Cg2ⁱ	0.93	2.98	3.777 (2)	145
C11—H11···Cg3ⁱⁱ	0.93	2.85	3.551 (2)	133
C13—H13A···Cg1ⁱⁱⁱ	0.97	3.00	3.749 (2)	135
C20—H20···Cg4^iv	0.93	2.62	3.498 (2)	157
C29—H29···Cg3^v	0.93	2.87	3.796 (3)	175

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

Acknowledgements

We gratefully acknowledge Professor M. Periasamy, School of Chemistry, University of Hyderabad, for providing laboratory facilities and the UGC Networking Resource Centre, School of Chemistry, University of Hyderabad, for providing characterization facilities.

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