1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde

Ramathilagam, C.; Umarani, P.R.; Venkatesan, N.; Rajakumar, P.; Gunasekaran, B.; Manivannan, V.

doi:10.1107/S1600536813034375

organic compounds

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Volume 70| Part 2| February 2014| Page o106

doi:10.1107/S1600536813034375

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1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde

C. Ramathilagam,^a P. R. Umarani,^b N. Venkatesan,^c P. Rajakumar,^c B. Gunasekaran ^d and V. Manivannan ^e ^*

^aDepartment of Physics, AMET University, Kanathur, Chennai 603 112, India, ^bPrincipal, Kundavai Nachiyar Govt College for Women, Thanjavur 613 007, India, ^cDepartment of Organic Chemistry, University of Madras, Guindy campus, Chennai 600 025, India, ^dDepartment of Physics & Nano Technology, SRM University, SRM Nagar, Kattankulathur, Kancheepuram Dist, Chennai 603 203, Tamil Nadu, India, and ^eDepartment of Research and Development, PRIST University, Vallam, Thanjavur 613 403, Tamil Nadu, India
^*Correspondence e-mail: phdguna@gmail.com

(Received 13 December 2013; accepted 20 December 2013; online 4 January 2014)

In the title compound, C₂₂H₁₅N₃O, the dihedral angle between the two indole units is 33.72 (3)°. The molecular structure features a weak intramolecular C—H⋯N interaction. In the crystal, weak C—H⋯O and C—H⋯π interactions, forming a two-dimensional network parallel to the bc plane.

CCDC reference: 978294

Related literature

For the biological activity of indole derivatives, see: Macor et al. (1992 ); Andreani et al. (2001 ); Quetin-Leclercq (1994 ); Mukhopadhyay et al. (1981 ); Singh et al. (2000 ). For related structures see: Dileep et al. (2012 ); Wu et al. (2012 )

Experimental

Crystal data

C₂₂H₁₅N₃O
M_r = 337.37
Orthorhombic, P n n a
a = 18.2208 (7) Å
b = 15.7672 (9) Å
c = 11.7034 (7) Å
V = 3362.3 (3) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 295 K
0.25 × 0.20 × 0.15 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.980, T_max = 0.987
11189 measured reflections
3521 independent reflections
2072 reflections with I > 2σ(I)
R_int = 0.031

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.118
S = 1.00
3521 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 is the centroid of the C16–C21 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H6⋯O1ⁱ	0.93	2.50	3.227 (3)	135
C12—H12⋯N1	0.93	2.41	2.931 (2)	116
C2—H2⋯Cg5ⁱⁱ	0.93	2.73	3.554 (2)	148
Symmetry codes: (i) x, y, z+1; (ii) $[x, -y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009 ); software used to prepare material for publication: SHELXL97.

Supporting information

CCDC reference: 978294

Crystal structure: contains datablock I. DOI: 10.1107/S1600536813034375/hg5369sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536813034375/hg5369Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536813034375/hg5369Isup3.cml

checkCIF report

Comment top

The chemistry of indole has been of increasing interest, since several compounds of this type possess diverse biological activities (Macor et al., 1992). These derivatives exhibit antibacterial, antifungal (Singh et al., 2000) and antitumour activities (Andreani et al., 2001). Some of the indole alkaloids extracted from plants possess interesting cytotoxic and antiparasitic properties (Quetin-Leclercq, 1994; Mukhopadhyay et al., 1981).

The geometric parameters of the title molecule (Fig. 1) agree well with reported similar structure (Dileep et al., 2012; Wu et al., 2012). The dihedral angle between the two indole moieties is 33.72 (3) °. The molecular structure is stabilized by weak intramolecular C—H···N interaction and the crystal packing is controlled by weak intermolecular C—H···O and C—H···π [C2—H2···Cg5(x, 1/2 - y, 1/2 - z) distance of 3.554 (2) Å, (Cg5 is the centroid of the ring defined by the atoms C16—C21)] interactions.

Related literature top

For the biological activity of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For related structures see: Dileep et al. (2012); Wu et al. (2012)

Experimental top

To a stirred solution of dimethylformamide (2.10g, 28.70 mmol) at 0°C, added phosphorous oxycholoride (1.10g, 7.17 mmol) drop wise under nitrogen atmosphere. 2,6-bis(N-indolyl)pyridine (1.0g, 3.23 mmol) in dimethylformamide was then added to the reaction at 0°C to 10°C. After the completion of addition, the reaction mixture was allow to attain room temperature and then stirred for additional one hour at 35°C. The reaction was then quenched by adding crushed ice (100 g) and further water (100 ml). Then the reaction mixture was then treated thrice with NaOH solution (1M). The reaction mixture was heated after adding one portion of NaOH solution and the rest of the two portions were added later with stirring. The reaction mixture was then kept in refrigerator overnight. The precipitate obtained was collected by filtration and then dissolved in chloroform (2 x 100 ml). The organic layer was then dried over (Na₂SO₄), filtered and solvent was evaporated under reduced pressure to give the residue which was then chromatographed over SiO₂ using hexane: chloroform (1:4) as eluting solvent to give the mono aldehyde(27%) as a colourless solid and further elution with CHCl₃: methanol (99:1) afforded the corresponding dialdehyde (55%).

Structure description top

For the biological activity of indole derivatives, see: Macor et al. (1992); Andreani et al. (2001); Quetin-Leclercq (1994); Mukhopadhyay et al. (1981); Singh et al. (2000). For related structures see: Dileep et al. (2012); Wu et al. (2012)

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with atom labels and 30% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing of (I), viewed down the c axis. Hydrogen bonds are shown as dashed lines.

1-[6-(1H-Indol-1-yl)pyridin-2-yl]-1H-indole-3-carbaldehyde top

Crystal data top

C₂₂H₁₅N₃O	F(000) = 1408
M_r = 337.37	D_x = 1.333 Mg m⁻³
Orthorhombic, Pnna	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2a 2bc	Cell parameters from 3755 reflections
a = 18.2208 (7) Å	θ = 2.0–26.6°
b = 15.7672 (9) Å	µ = 0.08 mm⁻¹
c = 11.7034 (7) Å	T = 295 K
V = 3362.3 (3) Å³	Block, colourless
Z = 8	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3521 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.031
Detector resolution: 0 pixels mm^-1	θ_max = 26.7°, θ_min = 2.1°
ω and φ scans	h = −14→22
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −19→13
T_min = 0.980, T_max = 0.987	l = −14→10
11189 measured reflections

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) = 0.118	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0507P)² + 0.3404P] where P = (F_o² + 2F_c²)/3
3521 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₂₂H₁₅N₃O	V = 3362.3 (3) Å³
M_r = 337.37	Z = 8
Orthorhombic, Pnna	Mo Kα radiation
a = 18.2208 (7) Å	µ = 0.08 mm⁻¹
b = 15.7672 (9) Å	T = 295 K
c = 11.7034 (7) Å	0.25 × 0.20 × 0.15 mm

Data collection top

Bruker APEXII CCD diffractometer	3521 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2072 reflections with I > 2σ(I)
T_min = 0.980, T_max = 0.987	R_int = 0.031
11189 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.118	H-atom parameters constrained
S = 1.00	Δρ_max = 0.15 e Å⁻³
3521 reflections	Δρ_min = −0.16 e Å⁻³
235 parameters

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
C1	0.19452 (8)	0.09535 (11)	0.38032 (14)	0.0407 (4)
C2	0.23265 (9)	0.15297 (11)	0.44461 (16)	0.0493 (5)
H2	0.2599	0.1961	0.4109	0.059*
C3	0.22882 (10)	0.14407 (12)	0.56135 (16)	0.0541 (5)
H3	0.2545	0.1812	0.6083	0.065*
C4	0.18729 (10)	0.08067 (12)	0.60890 (15)	0.0506 (5)
H4	0.1840	0.0745	0.6877	0.061*
C5	0.15023 (8)	0.02580 (10)	0.53543 (14)	0.0408 (4)
C6	0.10521 (10)	−0.06632 (14)	0.69106 (16)	0.0595 (5)
H6	0.1322	−0.0413	0.7495	0.071*
C7	0.05930 (11)	−0.13186 (14)	0.70475 (18)	0.0658 (6)
H7	0.0495	−0.1599	0.7730	0.079*
C8	0.02821 (9)	−0.15088 (12)	0.59656 (16)	0.0510 (5)
C9	−0.02337 (10)	−0.21026 (13)	0.55946 (19)	0.0619 (6)
H9	−0.0439	−0.2484	0.6109	0.074*
C10	−0.04334 (10)	−0.21191 (13)	0.4474 (2)	0.0639 (6)
H10	−0.0771	−0.2520	0.4222	0.077*
C11	−0.01383 (10)	−0.15451 (13)	0.37027 (18)	0.0598 (5)
H11	−0.0286	−0.1565	0.2943	0.072*
C12	0.03711 (9)	−0.09435 (12)	0.40377 (16)	0.0500 (5)
H12	0.0564	−0.0557	0.3518	0.060*
C13	0.05850 (9)	−0.09360 (10)	0.51763 (15)	0.0417 (4)
C14	0.13419 (11)	0.07765 (11)	0.19300 (16)	0.0528 (5)
H14	0.0891	0.0604	0.2220	0.063*
C15	0.15005 (12)	0.08533 (11)	0.07958 (16)	0.0579 (5)
C16	0.22504 (11)	0.11196 (11)	0.07240 (16)	0.0530 (5)
C17	0.27264 (15)	0.12907 (13)	−0.01922 (19)	0.0745 (7)
H17	0.2566	0.1241	−0.0943	0.089*
C18	0.34277 (16)	0.15310 (15)	0.0044 (2)	0.0852 (8)
H18	0.3745	0.1651	−0.0557	0.102*
C19	0.36810 (13)	0.16008 (14)	0.1154 (2)	0.0807 (7)
H19	0.4164	0.1765	0.1283	0.097*
C20	0.32270 (11)	0.14309 (12)	0.20799 (19)	0.0610 (5)
H20	0.3396	0.1470	0.2828	0.073*
C21	0.25168 (10)	0.12027 (10)	0.18389 (15)	0.0489 (5)
C22	0.09838 (16)	0.06891 (14)	−0.0091 (2)	0.0804 (7)
H22	0.0518	0.0513	0.0129	0.096*
N1	0.15424 (7)	0.03227 (8)	0.42256 (11)	0.0408 (4)
N2	0.10689 (7)	−0.04099 (9)	0.57769 (11)	0.0438 (4)
N3	0.19390 (8)	0.09876 (9)	0.25834 (12)	0.0464 (4)
O1	0.10984 (12)	0.07594 (11)	−0.11088 (14)	0.1121 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0422 (9)	0.0379 (10)	0.0420 (10)	0.0049 (8)	0.0027 (8)	0.0014 (8)
C2	0.0513 (11)	0.0412 (10)	0.0555 (12)	−0.0061 (9)	0.0021 (9)	−0.0001 (9)
C3	0.0583 (12)	0.0485 (11)	0.0555 (12)	−0.0063 (10)	−0.0070 (9)	−0.0080 (10)
C4	0.0599 (11)	0.0518 (12)	0.0402 (11)	−0.0027 (10)	−0.0033 (9)	−0.0020 (9)
C5	0.0404 (9)	0.0405 (10)	0.0415 (10)	0.0049 (8)	0.0026 (8)	0.0004 (8)
C6	0.0656 (12)	0.0715 (14)	0.0415 (11)	−0.0075 (11)	0.0011 (9)	0.0080 (10)
C7	0.0693 (13)	0.0733 (15)	0.0548 (13)	−0.0130 (12)	0.0074 (10)	0.0201 (11)
C8	0.0455 (10)	0.0474 (11)	0.0600 (12)	0.0034 (9)	0.0045 (9)	0.0108 (10)
C9	0.0523 (12)	0.0494 (13)	0.0841 (16)	−0.0028 (10)	0.0022 (11)	0.0159 (11)
C10	0.0525 (12)	0.0461 (13)	0.0930 (18)	−0.0048 (10)	−0.0075 (12)	0.0009 (12)
C11	0.0575 (12)	0.0569 (13)	0.0650 (13)	−0.0005 (11)	−0.0078 (10)	−0.0025 (11)
C12	0.0501 (10)	0.0461 (11)	0.0537 (12)	−0.0003 (9)	0.0010 (9)	0.0014 (9)
C13	0.0378 (9)	0.0380 (10)	0.0493 (11)	0.0060 (8)	0.0033 (8)	0.0006 (9)
C14	0.0634 (12)	0.0436 (11)	0.0515 (12)	−0.0067 (10)	−0.0049 (10)	0.0035 (9)
C15	0.0851 (15)	0.0409 (11)	0.0476 (12)	−0.0030 (11)	−0.0051 (11)	0.0012 (9)
C16	0.0813 (14)	0.0307 (10)	0.0469 (12)	0.0023 (10)	0.0109 (10)	0.0005 (9)
C17	0.117 (2)	0.0508 (13)	0.0559 (14)	0.0038 (14)	0.0237 (14)	−0.0006 (10)
C18	0.100 (2)	0.0672 (16)	0.088 (2)	−0.0025 (15)	0.0469 (16)	0.0001 (14)
C19	0.0740 (15)	0.0641 (15)	0.104 (2)	−0.0029 (12)	0.0309 (15)	−0.0014 (14)
C20	0.0591 (12)	0.0508 (12)	0.0729 (14)	0.0022 (10)	0.0118 (11)	0.0007 (10)
C21	0.0614 (12)	0.0323 (10)	0.0530 (12)	−0.0003 (9)	0.0097 (10)	0.0017 (9)
C22	0.125 (2)	0.0581 (14)	0.0584 (15)	−0.0025 (14)	−0.0222 (14)	−0.0043 (12)
N1	0.0427 (8)	0.0375 (8)	0.0422 (9)	0.0005 (7)	0.0031 (6)	0.0023 (7)
N2	0.0475 (8)	0.0438 (9)	0.0400 (9)	−0.0009 (7)	0.0039 (7)	0.0025 (7)
N3	0.0538 (9)	0.0405 (9)	0.0448 (9)	−0.0051 (7)	0.0049 (7)	0.0043 (7)
O1	0.189 (2)	0.0900 (13)	0.0577 (12)	0.0140 (13)	−0.0299 (12)	−0.0115 (9)

Geometric parameters (Å, º) top

C1—N1	1.331 (2)	C11—H11	0.9300
C1—C2	1.369 (2)	C12—C13	1.388 (2)
C1—N3	1.429 (2)	C12—H12	0.9300
C2—C3	1.375 (2)	C13—N2	1.400 (2)
C2—H2	0.9300	C14—C15	1.364 (2)
C3—C4	1.372 (2)	C14—N3	1.371 (2)
C3—H3	0.9300	C14—H14	0.9300
C4—C5	1.394 (2)	C15—C22	1.425 (3)
C4—H4	0.9300	C15—C16	1.432 (3)
C5—N1	1.3269 (19)	C16—C21	1.398 (2)
C5—N2	1.406 (2)	C16—C17	1.405 (3)
C6—C7	1.339 (3)	C17—C18	1.361 (3)
C6—N2	1.386 (2)	C17—H17	0.9300
C6—H6	0.9300	C18—C19	1.383 (3)
C7—C8	1.419 (3)	C18—H18	0.9300
C7—H7	0.9300	C19—C20	1.390 (3)
C8—C9	1.396 (3)	C19—H19	0.9300
C8—C13	1.405 (2)	C20—C21	1.372 (3)
C9—C10	1.362 (3)	C20—H20	0.9300
C9—H9	0.9300	C21—N3	1.408 (2)
C10—C11	1.386 (3)	C22—O1	1.215 (3)
C10—H10	0.9300	C22—H22	0.9300
C11—C12	1.384 (3)

N1—C1—C2	124.85 (16)	C12—C13—C8	121.02 (17)
N1—C1—N3	113.26 (15)	N2—C13—C8	107.35 (16)
C2—C1—N3	121.88 (16)	C15—C14—N3	110.69 (17)
C1—C2—C3	116.90 (17)	C15—C14—H14	124.7
C1—C2—H2	121.5	N3—C14—H14	124.7
C3—C2—H2	121.5	C14—C15—C22	123.6 (2)
C4—C3—C2	120.36 (17)	C14—C15—C16	106.58 (17)
C4—C3—H3	119.8	C22—C15—C16	129.9 (2)
C2—C3—H3	119.8	C21—C16—C17	118.7 (2)
C3—C4—C5	117.99 (17)	C21—C16—C15	107.70 (16)
C3—C4—H4	121.0	C17—C16—C15	133.6 (2)
C5—C4—H4	121.0	C18—C17—C16	118.6 (2)
N1—C5—C4	122.65 (16)	C18—C17—H17	120.7
N1—C5—N2	116.02 (15)	C16—C17—H17	120.7
C4—C5—N2	121.32 (16)	C17—C18—C19	121.7 (2)
C7—C6—N2	110.53 (17)	C17—C18—H18	119.1
C7—C6—H6	124.7	C19—C18—H18	119.1
N2—C6—H6	124.7	C18—C19—C20	121.2 (2)
C6—C7—C8	107.79 (17)	C18—C19—H19	119.4
C6—C7—H7	126.1	C20—C19—H19	119.4
C8—C7—H7	126.1	C21—C20—C19	116.9 (2)
C9—C8—C13	119.42 (18)	C21—C20—H20	121.6
C9—C8—C7	133.48 (18)	C19—C20—H20	121.6
C13—C8—C7	107.10 (17)	C20—C21—C16	122.93 (17)
C10—C9—C8	119.50 (19)	C20—C21—N3	129.86 (18)
C10—C9—H9	120.2	C16—C21—N3	107.17 (16)
C8—C9—H9	120.2	O1—C22—C15	125.7 (3)
C9—C10—C11	120.73 (19)	O1—C22—H22	117.1
C9—C10—H10	119.6	C15—C22—H22	117.1
C11—C10—H10	119.6	C5—N1—C1	117.23 (14)
C12—C11—C10	121.54 (19)	C6—N2—C13	107.22 (14)
C12—C11—H11	119.2	C6—N2—C5	124.40 (15)
C10—C11—H11	119.2	C13—N2—C5	128.38 (14)
C11—C12—C13	117.77 (17)	C14—N3—C21	107.86 (15)
C11—C12—H12	121.1	C14—N3—C1	123.68 (14)
C13—C12—H12	121.1	C21—N3—C1	128.43 (15)
C12—C13—N2	131.59 (16)

N1—C1—C2—C3	0.3 (3)	C19—C20—C21—N3	179.32 (18)
N3—C1—C2—C3	179.43 (15)	C17—C16—C21—C20	−1.1 (3)
C1—C2—C3—C4	−1.1 (3)	C15—C16—C21—C20	178.44 (17)
C2—C3—C4—C5	0.6 (3)	C17—C16—C21—N3	−179.34 (16)
C3—C4—C5—N1	0.6 (2)	C15—C16—C21—N3	0.19 (19)
C3—C4—C5—N2	179.67 (16)	C14—C15—C22—O1	179.0 (2)
N2—C6—C7—C8	−0.6 (2)	C16—C15—C22—O1	−0.8 (4)
C6—C7—C8—C9	−178.4 (2)	C4—C5—N1—C1	−1.4 (2)
C6—C7—C8—C13	0.5 (2)	N2—C5—N1—C1	179.54 (13)
C13—C8—C9—C10	0.2 (3)	C2—C1—N1—C5	0.9 (2)
C7—C8—C9—C10	178.9 (2)	N3—C1—N1—C5	−178.30 (13)
C8—C9—C10—C11	−1.0 (3)	C7—C6—N2—C13	0.6 (2)
C9—C10—C11—C12	0.6 (3)	C7—C6—N2—C5	−179.48 (16)
C10—C11—C12—C13	0.6 (3)	C12—C13—N2—C6	177.36 (18)
C11—C12—C13—N2	−178.68 (16)	C8—C13—N2—C6	−0.26 (18)
C11—C12—C13—C8	−1.3 (3)	C12—C13—N2—C5	−2.6 (3)
C9—C8—C13—C12	1.0 (3)	C8—C13—N2—C5	179.79 (15)
C7—C8—C13—C12	−178.03 (16)	N1—C5—N2—C6	169.29 (16)
C9—C8—C13—N2	178.90 (15)	C4—C5—N2—C6	−9.8 (2)
C7—C8—C13—N2	−0.11 (19)	N1—C5—N2—C13	−10.8 (2)
N3—C14—C15—C22	−179.03 (18)	C4—C5—N2—C13	170.11 (16)
N3—C14—C15—C16	0.8 (2)	C15—C14—N3—C21	−0.7 (2)
C14—C15—C16—C21	−0.6 (2)	C15—C14—N3—C1	−178.77 (16)
C22—C15—C16—C21	179.2 (2)	C20—C21—N3—C14	−177.78 (18)
C14—C15—C16—C17	178.8 (2)	C16—C21—N3—C14	0.30 (19)
C22—C15—C16—C17	−1.4 (4)	C20—C21—N3—C1	0.2 (3)
C21—C16—C17—C18	0.0 (3)	C16—C21—N3—C1	178.24 (16)
C15—C16—C17—C18	−179.4 (2)	N1—C1—N3—C14	34.4 (2)
C16—C17—C18—C19	0.7 (3)	C2—C1—N3—C14	−144.83 (17)
C17—C18—C19—C20	−0.3 (4)	N1—C1—N3—C21	−143.23 (16)
C18—C19—C20—C21	−0.8 (3)	C2—C1—N3—C21	37.5 (3)
C19—C20—C21—C16	1.5 (3)

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.50	3.227 (3)	135
C12—H12···N1	0.93	2.41	2.931 (2)	116
C2—H2···Cg5ⁱⁱ	0.93	2.73	3.554 (2)	148

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

Hydrogen-bond geometry (Å, º) top

Cg5 is the centroid of the C16–C21 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C6—H6···O1ⁱ	0.93	2.50	3.227 (3)	135.1
C12—H12···N1	0.93	2.41	2.931 (2)	115.6
C2—H2···Cg5ⁱⁱ	0.93	2.73	3.554 (2)	148.0

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

Acknowledgements

CR acknowledge the AMET University management, India, for their kind support.

References

Andreani, A., Granaiola, M., Leoni, A., Locatelli, A., Morigi, R., Rambaldi, M., Giorgi, G., Salvini, L. & Garaliene, V. (2001). Anticancer Drug. Des. 16, 167–174. Web of Science PubMed CAS Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dileep, C. S., Abdoh, M. M. M., Chakravarthy, M. P., Mohana, K. N. & Sridhar, M. A. (2012). Acta Cryst. E68, o3135. CSD CrossRef IUCr Journals Google Scholar
Macor, J. E., Fox, C. B., Johnson, C., Koe, B. K., Lebel, L. A. & Zorn, S. H. (1992). J. Med. Chem. 35, 3625–3632. CrossRef PubMed CAS Web of Science Google Scholar
Mukhopadhyay, S., Handy, G. A., Funayama, S. & Cordell, G. A. (1981). J. Nat. Prod. 44, 696–700. CrossRef CAS PubMed Web of Science Google Scholar
Quetin-Leclercq, J. (1994). J. Pharm. Belg. 49, 181–192. CAS PubMed Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Singh, U. P., Sarma, B. K., Mishra, P. K. & Ray, A. B. (2000). Fol. Microbiol. 45, 173–176. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wu, Y., Ren, W., Wang, Q. & He, G. (2012). Acta Cryst. E68, o1151. CSD CrossRef IUCr Journals Google Scholar

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