1-(4-Meth­oxy­phen­yl)-3-[2-(4-methyl­piperazin-1-yl)quinolin-3-yl]prop-2-en-1-one

Sharma, D.K.; Desai, N.R.; Sreenivasa, S.; Anthal, S.; Kant, R.

doi:10.1107/S2414314617016005

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 2| Part 11| November 2017| x171600

https://doi.org/10.1107/S2414314617016005

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1-(4-Methoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)quinolin-3-yl]prop-2-en-1-one

D. K. Sharma,^a N. R. Desai,^b S. Sreenivasa,^c Sumati Anthal ^a and Rajni Kant ^a ^*

^aDepartment of Physics , University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Chemistry, Tumkur University Tumkur, India, and ^cDepartment of Studies and Research in Chemistry, Tumkur University, Tumkur 572 103. Karnataka, India
^*Correspondence e-mail: rkant.ju@gmail.com

Edited by A. J. Lough, University of Toronto, Canada (Received 24 October 2017; accepted 6 November 2017; online 17 November 2017)

In the title molecule, C₂₄H₂₅N₃O₂, the piperazine ring adopts a chair conformation. The methoxyphenyl-substituted ring makes a dihedral angle of 6.79 (5)° with the quinoline ring system. In the crystal, molecules are consolidated in the crystal packing by a combination of weak C—H⋯N and C—H⋯O interactions. π–π stacking interactions also occur.

Keywords: crystal structure; direct methods; intermolecular hydrogen bonding; π–π interactions.

CCDC reference: 1584069

Structure description

Quinoline derivatives find importance owing to their wide occurrence in natural products and in biologically active compounds (Markees et al., 1970 ; Campbell et al., 1988 ; Kalluraya & Sreenivasa, 1998 ). Quinoline chalcone analogues have also attracted significant attention as a result of their bio-activity, e.g. anti-plasmodial, anti-microbial, anti-malarial and anti-cancer (Dimmock et al., 1999 ; Wu et al., 2006 ).

In the molecule of the title compound, (Fig. 1), bond lengths are in normal ranges and are comparable with related structures (Kaiser et al., 2009 ; Prasath et al., 2010 , 2011 ). The piperazine ring adopts a chair conformation with best mirror plane passing through atoms C20 and C22 [asymmetry parameter ΔC_s(C20) = 2/3] and the best twofold rotational axis bisecting the C22—C23 and C20—C21 bonds [asymmetry parameter ΔC₂(C22—C23) = 0.43; Duax & Norton, 1975 ). The quinoline ring system is essentially planar with a maximum deviation of 0.0384 (1) Å for atom C17. The methoxyphenyl-substituted ring makes a dihedral angle of 6.79 (5)° with the quinoline ring system.

Figure 1
The molecular structure of the title compound. Displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.

In the crystal, molecules are consolidated in the crystal packing by a combination of weak C—H⋯N and C—H⋯O interactions (Table 1, Fig. 2). The crystal structure also features π–π stacking interactions observed between the (C11–C13/C18/N1/C19) ring and the methoxyphenyl-substituted ring [centroid–centroid separation = 3.680 (1) Å, interplanar spacing = 3.350 Å and centroid shift = 1.52 Å] and the benzene ring (C13–C18) and the methoxyphenyl-substituted ring [centroid separation = 3.760 (1) Å, interplanar spacing = 3.625 Å and centroid shift = 1.00 Å].

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1A⋯O2ⁱ	0.96	2.52	3.3096 (2)	139
C14—H14⋯O1ⁱ	0.93	2.40	3.3112 (2)	165
C17—H17⋯N3ⁱⁱ	0.93	2.54	3.4029 (3)	155
Symmetry codes: (i) $[-x+2, y+{\script{1\over 2}}, -z-{\script{1\over 2}}]$ ; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
The packing arrangement of molecules viewed along the b axis.

Synthesis and crystallization

To a mixture of 9-acetylanthracene (0.01 mol) and 3-nitrobenzaldehyde (0.01 mol) in ethanol (50 ml), 15 ml of 10% sodium hydroxide solution was added and stirred at 273–278 K for 3 h. The precipitate formed was collected by filtration and purified by recrystallization from ethanol. Single crystals were grown from DMF by the slow evaporation method (m.p. 441–443 K).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₂₄H₂₅N₃O₂
M_r	387.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	12.1054 (9), 12.5816 (8), 13.8151 (10)
β (°)	104.660 (8)
V (Å³)	2035.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur, Sapphire3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ )
T_min, T_max	0.806, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7663, 3968, 2661
R_int	0.029
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.047, 0.129, 1.03
No. of reflections	3968
No. of parameters	264
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ), SHELXS97 (Sheldrick, 2008 ), SHELXL2016/6 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek,2009 ).

Structural data

CCDC reference: 1584069

Crystal structure: contains datablocks I, New_Global_Publ_Block. DOI: https://doi.org/10.1107/S2414314617016005/lh4028sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314617016005/lh4028Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314617016005/lh4028Isup3.cml

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016/6 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: PLATON (Spek,2009).

1-(4-Methoxyphenyl)-3-[2-(4-methylpiperazin-1-yl)quinolin-3-yl]prop-2-en-1-one top

Crystal data top

C₂₄H₂₅N₃O₂	F(000) = 824
M_r = 387.47	D_x = 1.264 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 12.1054 (9) Å	Cell parameters from 2213 reflections
b = 12.5816 (8) Å	θ = 3.8–28.1°
c = 13.8151 (10) Å	µ = 0.08 mm⁻¹
β = 104.660 (8)°	T = 293 K
V = 2035.6 (3) Å³	Block, white
Z = 4	0.30 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur, Sapphire3 diffractometer	3968 independent reflections
Radiation source: fine-focus sealed tube	2661 reflections with I > 2σ(I)
Detector resolution: 6.1049 pixels mm^-1	R_int = 0.029
ω scans	θ_max = 26.0°, θ_min = 3.7°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2010)	h = −10→14
T_min = 0.806, T_max = 1.000	k = −15→9
7663 measured reflections	l = −17→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.047	H-atom parameters constrained
wR(F²) = 0.129	w = 1/[σ²(F_o²) + (0.0522P)² + 0.2064P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
3968 reflections	Δρ_max = 0.14 e Å⁻³
264 parameters	Δρ_min = −0.16 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. All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å; and with U_iso(H) = 1.2U_eq(C), except for the methyl groups where U_iso(H) = 1.5U_eq(C).

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

	x	y	z	U_iso*/U_eq
N1	0.66324 (12)	0.04111 (11)	0.17671 (11)	0.0403 (4)
C19	0.68787 (15)	−0.02479 (13)	0.11184 (13)	0.0370 (4)
N2	0.65342 (12)	−0.13104 (11)	0.11343 (10)	0.0401 (4)
C13	0.75452 (15)	0.18349 (13)	0.10684 (13)	0.0399 (4)
C18	0.69723 (14)	0.14485 (13)	0.17632 (13)	0.0377 (4)
C11	0.75333 (15)	0.00475 (13)	0.04249 (13)	0.0381 (4)
C5	0.94339 (15)	−0.12384 (14)	−0.21987 (13)	0.0396 (4)
O1	1.11216 (12)	−0.07992 (10)	−0.44155 (10)	0.0572 (4)
N3	0.52218 (13)	−0.31851 (11)	0.11631 (12)	0.0464 (4)
C10	0.79570 (15)	−0.07570 (14)	−0.01499 (14)	0.0434 (5)
H10	0.786172	−0.146122	0.001693	0.052*
O2	0.86919 (14)	−0.24023 (10)	−0.11961 (11)	0.0661 (4)
C4	0.99289 (16)	−0.02680 (14)	−0.22924 (13)	0.0430 (5)
H4	0.987250	0.027752	−0.185317	0.052*
C17	0.67233 (16)	0.21571 (14)	0.24651 (14)	0.0466 (5)
H17	0.636395	0.191100	0.294237	0.056*
C23	0.62185 (18)	−0.16514 (14)	0.20369 (14)	0.0511 (5)
H23A	0.550435	−0.131980	0.206621	0.061*
H23B	0.680250	−0.143472	0.262350	0.061*
C12	0.78272 (16)	0.10930 (14)	0.04139 (13)	0.0431 (5)
H12	0.822651	0.131995	−0.004154	0.052*
C16	0.70063 (17)	0.32018 (14)	0.24486 (15)	0.0519 (5)
H16	0.682082	0.366850	0.290523	0.062*
C7	1.00681 (18)	−0.18600 (14)	−0.36065 (15)	0.0527 (5)
H7	1.010137	−0.239544	−0.406238	0.063*
C8	0.88595 (16)	−0.14806 (15)	−0.14025 (14)	0.0448 (5)
C2	1.05822 (16)	−0.08888 (14)	−0.36738 (14)	0.0430 (5)
C14	0.78453 (17)	0.29115 (14)	0.10835 (15)	0.0495 (5)
H14	0.823418	0.316742	0.063107	0.059*
C9	0.84587 (17)	−0.05991 (15)	−0.08776 (14)	0.0492 (5)
H9	0.856454	0.009486	−0.106793	0.059*
C22	0.60924 (18)	−0.28353 (15)	0.20268 (15)	0.0539 (5)
H22A	0.681542	−0.316235	0.201805	0.065*
H22B	0.589184	−0.306217	0.263146	0.065*
C21	0.55201 (18)	−0.28423 (14)	0.02596 (15)	0.0519 (5)
H21A	0.492652	−0.305925	−0.032006	0.062*
H21B	0.622716	−0.318125	0.022020	0.062*
C20	0.56593 (17)	−0.16596 (14)	0.02492 (14)	0.0476 (5)
H20A	0.587873	−0.144925	−0.035153	0.057*
H20B	0.493794	−0.131959	0.024143	0.057*
C3	1.05028 (16)	−0.00856 (14)	−0.30169 (14)	0.0440 (5)
H3	1.083415	0.057313	−0.306325	0.053*
C6	0.95132 (18)	−0.20370 (15)	−0.28761 (15)	0.0514 (5)
H6	0.918482	−0.269727	−0.283015	0.062*
C15	0.75707 (17)	0.35818 (15)	0.17556 (16)	0.0530 (5)
H15	0.775998	0.429808	0.175411	0.064*
C24	0.5069 (2)	−0.43288 (15)	0.11815 (19)	0.0685 (7)
H24A	0.447997	−0.454164	0.060792	0.103*
H24B	0.485380	−0.452479	0.178032	0.103*
H24C	0.577077	−0.467626	0.116856	0.103*
C1	1.17742 (19)	0.01359 (15)	−0.44464 (16)	0.0601 (6)
H1A	1.128690	0.074776	−0.451322	0.090*
H1B	1.210611	0.009934	−0.500733	0.090*
H1C	1.236977	0.019112	−0.383948	0.090*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0412 (9)	0.0439 (8)	0.0390 (9)	−0.0042 (7)	0.0159 (7)	−0.0015 (7)
C19	0.0351 (10)	0.0426 (10)	0.0330 (10)	−0.0027 (8)	0.0082 (8)	0.0027 (8)
N2	0.0437 (9)	0.0430 (8)	0.0341 (9)	−0.0088 (7)	0.0109 (7)	−0.0005 (7)
C13	0.0382 (10)	0.0431 (10)	0.0401 (11)	−0.0010 (8)	0.0131 (8)	0.0041 (8)
C18	0.0336 (9)	0.0414 (10)	0.0389 (10)	−0.0012 (8)	0.0108 (8)	0.0001 (8)
C11	0.0387 (10)	0.0437 (10)	0.0329 (10)	−0.0014 (8)	0.0112 (8)	0.0020 (8)
C5	0.0386 (10)	0.0427 (10)	0.0374 (10)	0.0080 (8)	0.0096 (8)	−0.0005 (8)
O1	0.0688 (10)	0.0589 (9)	0.0542 (9)	−0.0094 (7)	0.0349 (8)	−0.0149 (7)
N3	0.0481 (9)	0.0412 (9)	0.0540 (10)	−0.0087 (7)	0.0203 (8)	−0.0072 (7)
C10	0.0441 (11)	0.0459 (10)	0.0423 (11)	−0.0020 (9)	0.0145 (9)	−0.0002 (8)
O2	0.0970 (12)	0.0472 (8)	0.0651 (10)	0.0037 (8)	0.0410 (9)	0.0072 (7)
C4	0.0430 (11)	0.0469 (11)	0.0406 (11)	0.0040 (9)	0.0130 (9)	−0.0099 (9)
C17	0.0492 (12)	0.0503 (11)	0.0453 (12)	−0.0034 (9)	0.0211 (9)	−0.0028 (9)
C23	0.0645 (13)	0.0529 (11)	0.0379 (11)	−0.0167 (10)	0.0166 (10)	−0.0015 (9)
C12	0.0447 (11)	0.0504 (11)	0.0387 (11)	−0.0018 (9)	0.0188 (9)	0.0058 (9)
C16	0.0524 (12)	0.0487 (11)	0.0575 (14)	−0.0018 (10)	0.0193 (11)	−0.0114 (10)
C7	0.0696 (14)	0.0430 (11)	0.0516 (13)	−0.0004 (10)	0.0264 (11)	−0.0117 (9)
C8	0.0485 (11)	0.0462 (11)	0.0403 (11)	0.0068 (9)	0.0123 (9)	0.0023 (9)
C2	0.0419 (11)	0.0488 (11)	0.0408 (11)	0.0040 (9)	0.0153 (9)	−0.0055 (9)
C14	0.0533 (12)	0.0453 (10)	0.0551 (13)	−0.0043 (9)	0.0230 (10)	0.0056 (10)
C9	0.0597 (13)	0.0461 (11)	0.0476 (12)	0.0053 (10)	0.0243 (10)	0.0031 (9)
C22	0.0593 (13)	0.0537 (12)	0.0494 (13)	−0.0102 (10)	0.0149 (10)	0.0073 (10)
C21	0.0530 (12)	0.0560 (12)	0.0478 (12)	−0.0089 (10)	0.0149 (10)	−0.0133 (10)
C20	0.0492 (12)	0.0545 (11)	0.0382 (11)	−0.0078 (9)	0.0091 (9)	−0.0005 (9)
C3	0.0440 (11)	0.0437 (10)	0.0467 (12)	−0.0020 (9)	0.0161 (9)	−0.0082 (9)
C6	0.0646 (14)	0.0415 (10)	0.0534 (13)	0.0009 (10)	0.0246 (11)	−0.0033 (9)
C15	0.0527 (12)	0.0417 (11)	0.0657 (14)	−0.0058 (9)	0.0170 (11)	−0.0029 (10)
C24	0.0784 (17)	0.0465 (12)	0.0893 (18)	−0.0112 (11)	0.0370 (14)	−0.0112 (11)
C1	0.0659 (15)	0.0636 (13)	0.0588 (14)	−0.0145 (11)	0.0307 (12)	−0.0108 (11)

Geometric parameters (Å, º) top

N1—C19	1.309 (2)	C23—H23B	0.9700
N1—C18	1.369 (2)	C12—H12	0.9300
C19—N2	1.402 (2)	C16—C15	1.394 (3)
C19—C11	1.438 (2)	C16—H16	0.9300
N2—C23	1.458 (2)	C7—C6	1.365 (2)
N2—C20	1.468 (2)	C7—C2	1.385 (2)
C13—C14	1.401 (2)	C7—H7	0.9300
C13—C12	1.401 (2)	C8—C9	1.473 (2)
C13—C18	1.406 (2)	C2—C3	1.378 (2)
C18—C17	1.405 (2)	C14—C15	1.357 (3)
C11—C12	1.364 (2)	C14—H14	0.9300
C11—C10	1.458 (2)	C9—H9	0.9300
C5—C4	1.381 (2)	C22—H22A	0.9700
C5—C6	1.393 (2)	C22—H22B	0.9700
C5—C8	1.474 (2)	C21—C20	1.498 (2)
O1—C2	1.352 (2)	C21—H21A	0.9700
O1—C1	1.424 (2)	C21—H21B	0.9700
N3—C22	1.446 (2)	C20—H20A	0.9700
N3—C21	1.450 (2)	C20—H20B	0.9700
N3—C24	1.452 (2)	C3—H3	0.9300
C10—C9	1.315 (2)	C6—H6	0.9300
C10—H10	0.9300	C15—H15	0.9300
O2—C8	1.223 (2)	C24—H24A	0.9600
C4—C3	1.374 (2)	C24—H24B	0.9600
C4—H4	0.9300	C24—H24C	0.9600
C17—C16	1.360 (2)	C1—H1A	0.9600
C17—H17	0.9300	C1—H1B	0.9600
C23—C22	1.497 (2)	C1—H1C	0.9600
C23—H23A	0.9700

C19—N1—C18	118.71 (14)	C9—C8—C5	119.22 (16)
N1—C19—N2	118.22 (15)	O1—C2—C3	124.44 (16)
N1—C19—C11	123.47 (15)	O1—C2—C7	115.85 (16)
N2—C19—C11	118.23 (15)	C3—C2—C7	119.70 (17)
C19—N2—C23	115.93 (14)	C15—C14—C13	120.24 (17)
C19—N2—C20	115.28 (14)	C15—C14—H14	119.9
C23—N2—C20	109.53 (14)	C13—C14—H14	119.9
C14—C13—C12	123.31 (16)	C10—C9—C8	122.43 (17)
C14—C13—C18	119.68 (16)	C10—C9—H9	118.8
C12—C13—C18	116.96 (15)	C8—C9—H9	118.8
N1—C18—C13	122.23 (15)	N3—C22—C23	111.21 (16)
N1—C18—C17	119.01 (15)	N3—C22—H22A	109.4
C13—C18—C17	118.75 (15)	C23—C22—H22A	109.4
C12—C11—C19	116.49 (15)	N3—C22—H22B	109.4
C12—C11—C10	122.34 (15)	C23—C22—H22B	109.4
C19—C11—C10	120.84 (15)	H22A—C22—H22B	108.0
C4—C5—C6	118.01 (17)	N3—C21—C20	110.90 (15)
C4—C5—C8	123.41 (16)	N3—C21—H21A	109.5
C6—C5—C8	118.55 (16)	C20—C21—H21A	109.5
C2—O1—C1	118.02 (14)	N3—C21—H21B	109.5
C22—N3—C21	109.36 (15)	C20—C21—H21B	109.5
C22—N3—C24	110.90 (16)	H21A—C21—H21B	108.0
C21—N3—C24	111.75 (15)	N2—C20—C21	110.39 (15)
C9—C10—C11	127.31 (17)	N2—C20—H20A	109.6
C9—C10—H10	116.3	C21—C20—H20A	109.6
C11—C10—H10	116.3	N2—C20—H20B	109.6
C3—C4—C5	121.83 (16)	C21—C20—H20B	109.6
C3—C4—H4	119.1	H20A—C20—H20B	108.1
C5—C4—H4	119.1	C4—C3—C2	119.31 (17)
C16—C17—C18	120.18 (17)	C4—C3—H3	120.3
C16—C17—H17	119.9	C2—C3—H3	120.3
C18—C17—H17	119.9	C7—C6—C5	120.64 (18)
N2—C23—C22	109.45 (15)	C7—C6—H6	119.7
N2—C23—H23A	109.8	C5—C6—H6	119.7
C22—C23—H23A	109.8	C14—C15—C16	120.30 (17)
N2—C23—H23B	109.8	C14—C15—H15	119.9
C22—C23—H23B	109.8	C16—C15—H15	119.9
H23A—C23—H23B	108.2	N3—C24—H24A	109.5
C11—C12—C13	121.92 (16)	N3—C24—H24B	109.5
C11—C12—H12	119.0	H24A—C24—H24B	109.5
C13—C12—H12	119.0	N3—C24—H24C	109.5
C17—C16—C15	120.82 (18)	H24A—C24—H24C	109.5
C17—C16—H16	119.6	H24B—C24—H24C	109.5
C15—C16—H16	119.6	O1—C1—H1A	109.5
C6—C7—C2	120.48 (17)	O1—C1—H1B	109.5
C6—C7—H7	119.8	H1A—C1—H1B	109.5
C2—C7—H7	119.8	O1—C1—H1C	109.5
O2—C8—C9	120.28 (17)	H1A—C1—H1C	109.5
O2—C8—C5	120.48 (16)	H1B—C1—H1C	109.5

C18—N1—C19—N2	179.50 (15)	C4—C5—C8—O2	−161.56 (18)
C18—N1—C19—C11	2.8 (3)	C6—C5—C8—O2	16.5 (3)
N1—C19—N2—C23	−16.4 (2)	C4—C5—C8—C9	20.2 (3)
C11—C19—N2—C23	160.47 (16)	C6—C5—C8—C9	−161.74 (18)
N1—C19—N2—C20	113.40 (18)	C1—O1—C2—C3	8.3 (3)
C11—C19—N2—C20	−69.7 (2)	C1—O1—C2—C7	−172.89 (18)
C19—N1—C18—C13	1.9 (3)	C6—C7—C2—O1	179.19 (18)
C19—N1—C18—C17	−179.23 (16)	C6—C7—C2—C3	−2.0 (3)
C14—C13—C18—N1	178.29 (17)	C12—C13—C14—C15	−178.26 (19)
C12—C13—C18—N1	−4.2 (3)	C18—C13—C14—C15	−0.9 (3)
C14—C13—C18—C17	−0.5 (3)	C11—C10—C9—C8	179.61 (17)
C12—C13—C18—C17	176.95 (17)	O2—C8—C9—C10	2.9 (3)
N1—C19—C11—C12	−4.9 (3)	C5—C8—C9—C10	−178.87 (18)
N2—C19—C11—C12	178.38 (15)	C21—N3—C22—C23	58.9 (2)
N1—C19—C11—C10	168.70 (16)	C24—N3—C22—C23	−177.45 (16)
N2—C19—C11—C10	−8.0 (3)	N2—C23—C22—N3	−59.8 (2)
C12—C11—C10—C9	−14.4 (3)	C22—N3—C21—C20	−57.6 (2)
C19—C11—C10—C9	172.4 (2)	C24—N3—C21—C20	179.26 (17)
C6—C5—C4—C3	−1.1 (3)	C19—N2—C20—C21	169.36 (14)
C8—C5—C4—C3	176.98 (17)	C23—N2—C20—C21	−57.75 (19)
N1—C18—C17—C16	−177.06 (17)	N3—C21—C20—N2	57.7 (2)
C13—C18—C17—C16	1.8 (3)	C5—C4—C3—C2	0.4 (3)
C19—N2—C23—C22	−169.17 (16)	O1—C2—C3—C4	179.83 (18)
C20—N2—C23—C22	58.3 (2)	C7—C2—C3—C4	1.1 (3)
C19—C11—C12—C13	2.3 (3)	C2—C7—C6—C5	1.3 (3)
C10—C11—C12—C13	−171.15 (17)	C4—C5—C6—C7	0.2 (3)
C14—C13—C12—C11	179.28 (18)	C8—C5—C6—C7	−177.96 (18)
C18—C13—C12—C11	1.9 (3)	C13—C14—C15—C16	1.2 (3)
C18—C17—C16—C15	−1.6 (3)	C17—C16—C15—C14	0.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···O2ⁱ	0.96	2.52	3.3096 (2)	139
C14—H14···O1ⁱ	0.93	2.40	3.3112 (2)	165
C17—H17···N3ⁱⁱ	0.93	2.54	3.4029 (3)	155

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

Acknowledgements

RK acknowledges the Department of Science & Technology for a single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

Funding information

Funding for this research was provided by: Indian Council of Medical Research (grant No. BIC/12(14)/2012 to Rajni Kant); Department of Science and Technology, Ministry of Science and Technology, Science and Engineering Research Board (grant No. EMR/2014/000467 to Rajni Kant).

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