6-tert-Butyl-4-[(4-hy­droxy­methyl-2H-1,2,3-triazol-2-yl)meth­yl]-2H-chromen-2-one

El-Khatatneh, N.; Chandra; Shamala, D.; Shivashankar, K.; Mahendra, M.

doi:10.1107/S2414314616016187

organic compounds

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ISSN: 2414-3146

Volume 1| Part 10| October 2016| x161618

https://doi.org/10.1107/S2414314616016187

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RETRACTED ARTICLE
This article has been retracted. To view the retraction notice, click here.

Retracted: 6-tert-Butyl-4-[(4-hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-2H-chromen-2-one

Nasseem El-Khatatneh,^a Chandra,^a D. Shamala,^b K. Shivashankar ^b and M. Mahendra ^a ^*

^aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^bDepartment of Chemistry, Central College Campus, Bangalore University, Bangalore 560 001, India
^*Correspondence e-mail: mahendra@physics.uni-mysore.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 9 October 2016; accepted 12 October 2016; online 28 October 2016)

In the title compound, C₁₇H₁₉N₃O₃, the triazole ring and the chromene ring system [maximum deviation = 0.018 (2) Å for the O atom] bridged via a methylene C atom, are inclined to one another by 73.2 (1)°. In the crystal, molecules are linked by O—H⋯N hydrogen bonds, forming zigzag chains along [001]. The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to (010), and these layers are linked by C—H⋯π and π–π interactions [intercentroid distance = 3.557 (1) Å], forming a three-dimensional newwork. The hydroxymethyl group at the 4-position of the triazole ring is disordered over two sets of sites, with a refined occupancy ratio of 0.418 (11):0.584 (11).

Keywords: crystal structure; chromones; triazole; hydrogen bonding; C—H⋯π interactions.

CCDC reference: 1509457

Structure description

Chromones are a group of natural and synthetic oxygen heterocyclic compounds having a high degree of chemical diversity that is frequently linked to a broad array of biological activities (Gaspar et al., 2015 ). Coumarins and their derivatives have wide applications in a number of diverse areas. They are used in the pharmaceutical industry as precursor reagents in the synthesis of a number of synthetic anticoagulant pharmaceuticals (Bairagi et al., 2012 ), the most notable being warfarin (Holbrook et al., 2005 ). Modified coumarins are a type of vitamin K antagonist (Marongiu & Barcellona, 2015 ). Coumarins are of great interest due to their biological properties (Lacy & O'Kennedy, 2004 ). In particular, their physiological, bacteriostatic and anti-tumour activity (Mustafa et al., 2011 ) makes these compounds attractive for further backbone derivatization and screening for their therapeutic properties. 2H-chromen-2-ones exhibit extensive natural occurrence and biocompatibility, and have been found to exhibit variety of biological activities (Naik et al., 2012 ).

In the molecular structure of the title compound (Fig. 1), the chromene unit (O16/C9—C15/C17/C18), as expected, is almost planar, with a maximum deviation of 0.018 (2) Å for the ring atom O16. The carbonyl O atom, O19, is displaced from the chromene mean plane by 0.059 (2) Å. The triazole (N1/N4/N5/C2/C3) and the chromene (O16/C9–C15/C17/C18) rings, bridged via a methylene C atom, C8, are inclined to one another by 73.2 (1)°. The intra-ring bond conformation between chromene and triazole moieties are also characterized by torsion angles of −72.6 (2)° (C9—C8—N1—N5) and 178.24 (18)° (C20—C12—C11—C10). The hydroxymethyl O atom is not coplanar with the triazole ring, as indicated by torsion angle C2—C3—C6B—O7B = −58 (2)°. One methyl unit of the tert-butyl group is almost coplanar with the chromene ring as suggested by the torsion angle C11—C12—C20—C23 = 5.2 (3)°, while the other two methyl groups are above and below the ring plane, with torsion angles C13—C12—C20—C21 and C13—C12—C20—C22, being 64.9 (2) and −54.7 (3)°, respectively.

Figure 1
A view of the molecular structure of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 50% probability (atoms C6A/O7A and C6B/O7B concern the disordered hydroxymethyl group).

In the crystal, molecules are are linked by an O—H⋯N hydrogen bond, forming chains along the c-axis direction (Table 1). The chains are linked by C—H⋯O hydrogen bonds, forming layers parallel to the ac plane (Table 1 and Fig. 2). Finally, the layers are linked by C—H⋯π and π–π interactions, forming a three-dimensional network (Table 1 and Fig. 2). The π–π interactions involve Cg1⋯Cg2ⁱ = Cg2⋯Cg1ⁱⁱ = 3.557 (1) Å [the two rings are inclined to one another by 14.95 (11)°, and the interplanar distances and slippages are 3.463 (1) and 1.545 Å, and 3.204 (1) and 0.812 Å, respectively; Cg1 and Cg2 are the centroids of rings N1/N4/N5/C2/C3 and O16/C9/C10/C15/C17/C18; symmetry codes: (i) −x + 1, −y + 1, z − $[{1\over 2}]$ and (ii) −x + 1, −y + 1, z + $[{1\over 2}]$ ].

Table 1
Hydrogen-bond geometry (Å, °)

Cg3 is the centroid of the C10–C15 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O7B—H7B⋯N4ⁱ	0.82	2.49	3.198 (7)	146
C2—H2⋯O19ⁱⁱ	0.93	2.54	3.365 (3)	147
C23—H23B⋯O19ⁱⁱⁱ	0.96	2.59	3.421 (3)	146
C22—H22B⋯Cg3^iv	0.96	2.99	3.818 (3)	145
Symmetry codes: (i) $[-x+2, -y+1, z-{\script{1\over 2}}]$ ; (ii) x, y, z-1; (iii) x-1, y, z-1; (iv) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z]$ .

Figure 2
A view along the c axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines and the C—H⋯π interactions as black lines (see Table 1

), and examples of the π–π interactions as thick orange lines. For clarity, only the H atoms involved in these intermolecular interactions have been included.

Synthesis and crystallization

A mixture of propargyl alcohol (1.9 mmol), sodium azide (0.14 g, 2.0 mmol), copper(I) iodide (10 mol%) and triethylamine (0.19 g, 1.9 mmol) in 20 ml of acetone was taken in a round-bottom flask and stirred for 1 h. To this mixture, 4-bromomethylcoumarin (1.9 mmol) was added and the stirring continued for 8 h (the reaction was monitored by TLC). After the completion of the reaction, the catalyst was filtered through celite and the product was extracted with ether (3.10 ml). The solvent was removed under vacuum. The crude product was dried and recrystallized from ethyl acetate solution to give colourless block-like crystals of the title compound (yield 90%, m.p. 473–475 K). IR (KBr, cm⁻¹): 1715 (lactone C=O), 3221 (OH). ¹H NMR (400 MHz, CDC₁₃): δ 1.28 (s, 9H, 3-CH₃ of tert-butyl group), 1.70 (s, 1H, OH), 4.84 (s, 2H, –CH₂O–), 5.77 (s, 2H, –CH₂N–), 6.06 (s, 1H, C₃—H), 7.31 (d, 1H, C₇—H, J_1,2 = 12 Hz), 7.57(s, 1H, C₅—H), 7.61(d, 1H, C₈—H, J_1,2 = 8.8 Hz), 7.73 (s, 1H, Tr—H) p.p.m. ¹³C NMR (100 MHz, DMSO-d6): δ 31.0 (3C), 34.5, 49.2, 54.9, 113.7, 116.3, 116.4, 121.0, 123.7, 129.8, 147.0, 148.6, 150.4, 151.1, 159.5 p.p.m.. Analysis for C₁₇H₁₉N₃O₃. Calculated: C, 65.16; H, 6.11; N, 13.41%. Found: C, 65.12; H, 6.07; N, 13.39%.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The hydroxymethyl group at the 4-position of the triazole ring is disordered over two sets of sites, with a refined occupancy ratio of 0.418 (11):0.584 (11) for atoms C6A:C6B and O7A:O7B. The structure was refined as an inversion twin; Flack parameter = 0.2 (5).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₉N₃O₃
M_r	313.35
Crystal system, space group	Orthorhombic, Pna2₁
Temperature (K)	293
a, b, c (Å)	8.9099 (12), 24.550 (3), 7.2359 (11)
V (Å³)	1582.7 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.75
Crystal size (mm)	0.32 × 0.22 × 0.12

Data collection
Diffractometer	Bruker X8 Proteum
No. of measured, independent and observed [I > 2σ(I)] reflections	5136, 1581, 1565
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.585

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.080, 1.07
No. of reflections	1581
No. of parameters	227
No. of restraints	38
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.10, −0.11
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXS2016 (Sheldrick, 2008 ), SHELXL2016 (Sheldrick, 2015 ), PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2008 ).

Structural data

CCDC reference: 1509457

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314616016187/su4083sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616016187/su4083Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314616016187/su4083Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS2016 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2016 (Sheldrick, 2015) and PLATON (Spek, 2009).

6-tert-Butyl-4-[(4-hydroxymethyl-2H-1,2,3-triazol-2-yl)methyl]-2H-chromen-2-one top

Crystal data top

C₁₇H₁₉N₃O₃	D_x = 1.315 Mg m⁻³
M_r = 313.35	Cu Kα radiation, λ = 1.54178 Å
Orthorhombic, Pna2₁	Cell parameters from 1581 reflections
a = 8.9099 (12) Å	θ = 7.2–64.4°
b = 24.550 (3) Å	µ = 0.75 mm⁻¹
c = 7.2359 (11) Å	T = 293 K
V = 1582.7 (4) Å³	Block, colourless
Z = 4	0.32 × 0.22 × 0.12 mm
F(000) = 664

Data collection top

Bruker X8 Proteum diffractometer	1565 reflections with I > 2σ(I)
Radiation source: Bruker MicroStar microfocus rotating anode	R_int = 0.022
Helios multilayer optics monochromator	θ_max = 64.4°, θ_min = 7.2°
Detector resolution: 18.4 pixels mm^-1	h = −10→9
φ and ω scans	k = −28→27
5136 measured reflections	l = −3→8
1581 independent 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)] = 0.030	H-atom parameters constrained
wR(F²) = 0.080	w = 1/[σ²(F_o²) + (0.0492P)² + 0.1878P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
1581 reflections	Δρ_max = 0.10 e Å⁻³
227 parameters	Δρ_min = −0.11 e Å⁻³
38 restraints	Absolute structure: Refined as an inversion twin
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.2 (5)

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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C12	0.1311 (2)	0.32195 (7)	0.4515 (3)	0.0390 (4)
N1	0.60931 (17)	0.47866 (6)	0.3641 (3)	0.0440 (4)
C11	0.2465 (2)	0.35946 (7)	0.4284 (3)	0.0362 (4)
H11	0.246706	0.381302	0.323334	0.043*
O16	0.47177 (19)	0.33551 (6)	0.8472 (3)	0.0573 (4)
C13	0.1364 (2)	0.28959 (8)	0.6120 (3)	0.0498 (5)
H13	0.060668	0.264168	0.631743	0.060*
C15	0.3613 (2)	0.33239 (8)	0.7134 (3)	0.0431 (5)
O19	0.6737 (2)	0.37446 (8)	0.9624 (3)	0.0858 (7)
C9	0.4845 (2)	0.40488 (8)	0.5398 (3)	0.0399 (5)
N4	0.7328 (2)	0.54936 (8)	0.4439 (3)	0.0576 (5)
C10	0.3626 (2)	0.36557 (7)	0.5575 (3)	0.0359 (4)
C2	0.7321 (2)	0.47844 (8)	0.2567 (3)	0.0438 (5)
H2	0.757906	0.453111	0.166558	0.053*
N5	0.6080 (2)	0.52202 (8)	0.4770 (3)	0.0578 (6)
C17	0.5846 (3)	0.37326 (9)	0.8355 (4)	0.0564 (6)
C8	0.4850 (2)	0.44007 (9)	0.3695 (4)	0.0472 (5)
H8A	0.490187	0.416841	0.261230	0.057*
H8B	0.391225	0.460096	0.363693	0.057*
C18	0.5886 (2)	0.40772 (9)	0.6742 (4)	0.0497 (5)
H18	0.666089	0.432863	0.662608	0.060*
C20	0.0017 (2)	0.31619 (8)	0.3138 (4)	0.0442 (5)
C23	0.0228 (3)	0.35213 (11)	0.1440 (4)	0.0645 (7)
H23A	0.023399	0.389703	0.180780	0.097*
H23B	−0.058150	0.345981	0.058916	0.097*
H23C	0.116334	0.343349	0.085332	0.097*
C21	−0.1441 (2)	0.33404 (11)	0.4108 (5)	0.0676 (7)
H21A	−0.135254	0.371364	0.448802	0.101*
H21B	−0.160897	0.311489	0.517178	0.101*
H21C	−0.226873	0.330379	0.326834	0.101*
C14	0.2491 (3)	0.29416 (9)	0.7405 (3)	0.0531 (5)
H14	0.250115	0.271857	0.844358	0.064*
C6A	0.957 (3)	0.5456 (15)	0.238 (6)	0.0620 (7)	0.418 (11)
H6A1	0.981776	0.528038	0.121698	0.074*	0.418 (11)
H6A2	0.947595	0.584396	0.215757	0.074*	0.418 (11)
O7A	1.0709 (6)	0.5357 (3)	0.3685 (13)	0.076 (3)	0.418 (11)
H7A	1.126711	0.562246	0.373797	0.113*	0.418 (11)
C6B	0.958 (2)	0.5453 (10)	0.243 (4)	0.0620 (7)	0.582 (11)
H6B1	0.949910	0.554755	0.113039	0.074*	0.582 (11)
H6B2	0.981856	0.578301	0.310511	0.074*	0.582 (11)
O7B	1.0773 (4)	0.5076 (3)	0.2653 (10)	0.0883 (19)	0.582 (11)
H7B	1.086999	0.489670	0.170471	0.132*	0.582 (11)
C3	0.8105 (2)	0.52358 (8)	0.3088 (3)	0.0456 (5)
C22	−0.0126 (3)	0.25684 (10)	0.2520 (5)	0.0696 (7)
H22A	−0.097310	0.253182	0.170927	0.104*
H22B	−0.026487	0.233981	0.358248	0.104*
H22C	0.077008	0.246108	0.187940	0.104*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C12	0.0373 (9)	0.0366 (8)	0.0432 (11)	−0.0002 (7)	0.0003 (10)	−0.0017 (9)
N1	0.0402 (8)	0.0519 (9)	0.0397 (10)	−0.0097 (6)	−0.0021 (8)	−0.0082 (9)
C11	0.0372 (10)	0.0377 (8)	0.0338 (11)	0.0004 (7)	−0.0020 (8)	0.0010 (8)
O16	0.0706 (10)	0.0580 (8)	0.0434 (9)	0.0082 (7)	−0.0239 (9)	0.0048 (8)
C13	0.0542 (12)	0.0445 (10)	0.0508 (13)	−0.0063 (9)	0.0027 (11)	0.0063 (10)
C15	0.0509 (11)	0.0427 (10)	0.0356 (11)	0.0083 (8)	−0.0067 (10)	−0.0006 (9)
O19	0.0912 (14)	0.0893 (12)	0.0769 (14)	0.0107 (10)	−0.0554 (13)	−0.0029 (12)
C9	0.0339 (9)	0.0470 (10)	0.0388 (11)	0.0024 (7)	−0.0050 (9)	−0.0057 (9)
N4	0.0570 (10)	0.0593 (10)	0.0566 (12)	−0.0176 (8)	0.0027 (11)	−0.0126 (10)
C10	0.0372 (9)	0.0382 (8)	0.0323 (10)	0.0039 (7)	−0.0032 (9)	−0.0021 (8)
C2	0.0435 (11)	0.0489 (10)	0.0389 (11)	−0.0026 (8)	0.0026 (9)	−0.0026 (9)
N5	0.0543 (10)	0.0618 (11)	0.0573 (14)	−0.0144 (9)	0.0083 (10)	−0.0190 (11)
C17	0.0573 (13)	0.0580 (12)	0.0538 (15)	0.0130 (10)	−0.0274 (13)	−0.0112 (12)
C8	0.0399 (10)	0.0591 (11)	0.0426 (12)	−0.0140 (8)	−0.0071 (10)	0.0021 (11)
C18	0.0420 (10)	0.0566 (11)	0.0505 (13)	0.0010 (9)	−0.0124 (11)	−0.0103 (11)
C20	0.0354 (9)	0.0446 (10)	0.0525 (13)	−0.0069 (7)	−0.0045 (10)	0.0017 (10)
C23	0.0521 (12)	0.0841 (16)	0.0572 (16)	−0.0168 (12)	−0.0195 (13)	0.0131 (14)
C21	0.0410 (11)	0.0788 (15)	0.083 (2)	−0.0002 (10)	0.0005 (14)	−0.0012 (15)
C14	0.0702 (13)	0.0482 (11)	0.0409 (12)	0.0017 (10)	−0.0016 (11)	0.0120 (10)
C6A	0.0507 (13)	0.0732 (15)	0.062 (2)	−0.0176 (11)	0.0022 (14)	0.0079 (14)
O7A	0.049 (3)	0.085 (4)	0.092 (6)	−0.014 (3)	−0.016 (3)	0.022 (4)
C6B	0.0507 (13)	0.0732 (15)	0.062 (2)	−0.0176 (11)	0.0022 (14)	0.0079 (14)
O7B	0.0576 (19)	0.094 (3)	0.113 (4)	−0.0042 (19)	0.029 (2)	−0.010 (3)
C3	0.0431 (10)	0.0502 (10)	0.0434 (12)	−0.0084 (8)	−0.0005 (10)	0.0036 (10)
C22	0.0727 (15)	0.0572 (13)	0.0789 (19)	−0.0102 (11)	−0.0213 (16)	−0.0117 (13)

Geometric parameters (Å, º) top

C12—C11	1.391 (3)	C18—H18	0.9300
C12—C13	1.408 (3)	C20—C23	1.524 (4)
C12—C20	1.531 (3)	C20—C22	1.529 (3)
N1—C2	1.342 (3)	C20—C21	1.540 (3)
N1—N5	1.342 (2)	C23—H23A	0.9600
N1—C8	1.458 (2)	C23—H23B	0.9600
C11—C10	1.402 (3)	C23—H23C	0.9600
C11—H11	0.9300	C21—H21A	0.9600
O16—C17	1.370 (3)	C21—H21B	0.9600
O16—C15	1.383 (3)	C21—H21C	0.9600
C13—C14	1.373 (3)	C14—H14	0.9300
C13—H13	0.9300	C6A—O7A	1.411 (18)
C15—C14	1.385 (3)	C6A—C3	1.50 (4)
C15—C10	1.391 (3)	C6A—H6A1	0.9700
O19—C17	1.214 (3)	C6A—H6A2	0.9700
C9—C18	1.346 (3)	O7A—H7A	0.8200
C9—C10	1.458 (3)	C6B—O7B	1.416 (15)
C9—C8	1.505 (3)	C6B—C3	1.50 (3)
N4—N5	1.320 (3)	C6B—H6B1	0.9700
N4—C3	1.355 (3)	C6B—H6B2	0.9700
C2—C3	1.363 (3)	O7B—H7B	0.8200
C2—H2	0.9300	C22—H22A	0.9600
C17—C18	1.442 (4)	C22—H22B	0.9600
C8—H8A	0.9700	C22—H22C	0.9600
C8—H8B	0.9700

C11—C12—C13	116.66 (19)	C22—C20—C21	109.52 (19)
C11—C12—C20	122.66 (18)	C12—C20—C21	108.2 (2)
C13—C12—C20	120.67 (17)	C20—C23—H23A	109.5
C2—N1—N5	111.27 (16)	C20—C23—H23B	109.5
C2—N1—C8	129.22 (18)	H23A—C23—H23B	109.5
N5—N1—C8	119.51 (17)	C20—C23—H23C	109.5
C12—C11—C10	122.41 (19)	H23A—C23—H23C	109.5
C12—C11—H11	118.8	H23B—C23—H23C	109.5
C10—C11—H11	118.8	C20—C21—H21A	109.5
C17—O16—C15	121.1 (2)	C20—C21—H21B	109.5
C14—C13—C12	122.45 (19)	H21A—C21—H21B	109.5
C14—C13—H13	118.8	C20—C21—H21C	109.5
C12—C13—H13	118.8	H21A—C21—H21C	109.5
O16—C15—C14	116.9 (2)	H21B—C21—H21C	109.5
O16—C15—C10	121.97 (18)	C13—C14—C15	119.2 (2)
C14—C15—C10	121.14 (19)	C13—C14—H14	120.4
C18—C9—C10	118.9 (2)	C15—C14—H14	120.4
C18—C9—C8	124.07 (18)	O7A—C6A—C3	110 (3)
C10—C9—C8	116.99 (17)	O7A—C6A—H6A1	109.8
N5—N4—C3	108.91 (18)	C3—C6A—H6A1	109.8
C15—C10—C11	118.14 (17)	O7A—C6A—H6A2	109.8
C15—C10—C9	117.70 (18)	C3—C6A—H6A2	109.8
C11—C10—C9	124.15 (18)	H6A1—C6A—H6A2	108.2
N1—C2—C3	104.73 (19)	C6A—O7A—H7A	109.5
N1—C2—H2	127.6	O7B—C6B—C3	112.9 (18)
C3—C2—H2	127.6	O7B—C6B—H6B1	109.0
N4—N5—N1	106.58 (18)	C3—C6B—H6B1	109.0
O19—C17—O16	116.7 (3)	O7B—C6B—H6B2	109.0
O19—C17—C18	125.6 (2)	C3—C6B—H6B2	109.0
O16—C17—C18	117.72 (19)	H6B1—C6B—H6B2	107.8
N1—C8—C9	113.38 (18)	C6B—O7B—H7B	109.5
N1—C8—H8A	108.9	N4—C3—C2	108.50 (18)
C9—C8—H8A	108.9	N4—C3—C6B	120.9 (11)
N1—C8—H8B	108.9	C2—C3—C6B	130.6 (11)
C9—C8—H8B	108.9	N4—C3—C6A	121.5 (15)
H8A—C8—H8B	107.7	C2—C3—C6A	130.0 (15)
C9—C18—C17	122.5 (2)	C20—C22—H22A	109.5
C9—C18—H18	118.7	C20—C22—H22B	109.5
C17—C18—H18	118.7	H22A—C22—H22B	109.5
C23—C20—C22	109.0 (2)	C20—C22—H22C	109.5
C23—C20—C12	112.25 (16)	H22A—C22—H22C	109.5
C22—C20—C12	109.95 (17)	H22B—C22—H22C	109.5
C23—C20—C21	107.9 (2)

Hydrogen-bond geometry (Å, º) top

Cg3 is the centroid of the C10–C15 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O7B—H7B···N4ⁱ	0.82	2.49	3.198 (7)	146
C2—H2···O19ⁱⁱ	0.93	2.54	3.365 (3)	147
C23—H23B···O19ⁱⁱⁱ	0.96	2.59	3.421 (3)	146
C22—H22B···Cg3^iv	0.96	2.99	3.818 (3)	145

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

Acknowledgements

MM thanks the UGC, New Delhi, Government of India, for awarding a project under the title F. No. 41–920/2012(SR) dated: 25–07-2012. SD is grateful to the Council of Scientific and Industrial Research, New Delhi, India, for financial assistance [grant No. 02 (0172)/13/EMR-II].

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