(E)-5-(4-Methyl­benzyl­idene)-1-phenyl-4,5,6,7-tetra­hydro-1H-indazol-4-one

Meenatchi, C.S.; Athimoolam, S.; Suresh, J.; Priya, R.V.; Rubina, S.R.; Bhandari, S.R.

doi:10.1107/S2414314622002838

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 7| Part 3| March 2022| x220283

https://doi.org/10.1107/S2414314622002838

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(E)-5-(4-Methylbenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one

C. Selva Meenatchi,^a S. Athimoolam,^b J. Suresh,^a R. Vishnu Priya,^a S. Raja Rubina ^c and S. R. Bhandari ^d ^*

^aDepartment of Physics, The Madura College, Madurai 625 011, India, ^bDepartment of Physics, University College of Engineering Nagercoil, Anna University, Nagercoil 629 004, Tamilnadu, India, ^cDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625 021, India, and ^dDepartment of Physics, Bhairahawa M. Campus, Tribhuvan University, Nepal
^*Correspondence e-mail: shalikaa.bh@gmail.com

Edited by E. R. T. Tiekink, Sunway University, Malaysia (Received 16 February 2022; accepted 14 March 2022; online 29 March 2022)

In the title compound, C₂₁H₁₈N₂O, the non-aromatic six-membered ring adopts a distorted envelope conformation with one of the methylene-C atoms being the flap atom. The dihedral angle between the phenyl and 4-tolyl rings is 75.3 (1)°. The 1,2-diazole ring forms dihedral angles of 41.9 (1) and 65.5 (1)° with the phenyl and 4-tolyl rings, respectively. In the crystal, stabilizing C—H⋯O, C—H⋯π and π–π interactions are evident. The calculated Hirshfeld surfaces highlight the prominent role of C—H⋯O interactions (8.6%), along with H⋯H (51.7%) and C⋯H/H⋯C (29.2%) surface contacts.

Keywords: crystal structure; Hirshfeld surface; indazol-4-one.

CCDC reference: 2158365

Structure description

Heterocyclic compounds have been investigated for a long while in view of their pharmaceutical and biological importance. 1,2-Diazole derivatives are found to possess anti-bacterial, anti-viral, anti-inflammatory, anti-depressant and anti-cancer activities (Popat et al., 2003 ; Faisal et al., 2019 ) because of their conformational freedom and exhibit intermolecular interactions of biological relevance. Owing to its medicinal interest and in a continuation of previous work, the crystal and molecular structures of another indazole derivative, namely, (E)-5-(4-methylbenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one, (I), is reported here.

The molecule of (I) and the recently reported 4-chlorobenzylidene derivative (II) (Meenatchi et al., 2021 ) are isomorphous. The shorter b-axis lengths differ slightly between the isomorphous crystal structures, i.e. 8.7177 (5) Å for (I) and 8.6604 (5) Å for (II). In (I), the non-aromatic six-membered ring adopts a distorted envelope conformation with the methylene-C9 atom being the flap atom, Fig. 1. The heterocyclic five-membered ring forms dihedral angles of 41.9 (1) and 65.5 (1)° with the pendent N-bound phenyl and 4-tolyl rings, respectively. A weak intramolecular C6—H12⋯O1 interaction (Table 1) stabilizes the molecular structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C6—H12⋯O1	0.93	2.43	2.806 (2)	104
C12—H4⋯O1ⁱ	0.93	2.52	3.312 (2)	143
C17—H5⋯O1ⁱⁱ	0.93	2.60	3.5081 (19)	164
C18—H8⋯O1ⁱⁱⁱ	0.93	2.46	3.325 (2)	155
Symmetry codes: (i) ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y, z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of (I), showing 50% probability displacement ellipsoids

The molecular packing features C—H⋯O, C—H⋯π and π–π interactions (Fig. 2). The C—H⋯O intermolecular interactions, viz., C12—H4⋯O1ⁱ and C17—H5⋯O1ⁱⁱ, lead, respectively, to two centrosymmetric ring R₂²(16) and R₂²(10) motifs (Bernstein et al., 1995 ) (Fig. 3); see Table 1 for symmetry operations. These centrosymmetric dimers are connected through another C—H⋯O interaction, namely, C18—H8⋯O1ⁱⁱⁱ, leading to a chain C(8) motif along the c-axis direction of the unit cell (Fig. 4).

Figure 2
The molecular packing of (I), viewed down the b axis.

Figure 3
C—H⋯O interactions shown as dashed lines forming ring (a) R₂²(16) and (b) R₂²(10) motifs.

Figure 4
C—H⋯O interactions shown as dashed lines forming chain C(8) motif along b axis of the unit cell

As a quantitative approach to analyse the intermolecular interactions, the Hirshfeld surfaces and two-dimensional (2-D) fingerprint plots were generated by employing the Crystal Explorer software (Wolff et al., 2012 ). The Hirshfeld surface is colour-mapped with the normalized contact distance, d_norm, from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The different types of intermolecular interactions can be identified by colour coding the distances from the surface to the nearest atom exterior (d_e) or interior (d_i) plots to the surface. The 2-D fingerprint plots from the surface analysis and the d_norm surface were analysed for (I) to further explore the packing modes and intermolecular interactions. The 3-D Hirshfeld surfaces and 2-D fingerprint plots with percentage contributions are shown in Fig. 5. C⋯H/H⋯C contacts (with a pair of spikes in the fingerprint plot, 29.2%) and O⋯H/H⋯O interactions (sharp spikes, 8.6%) make a significant contribution to the overall contacts; the latter incorporate the notable C—H⋯O interactions. The H⋯H interactions contribute 51.7% with widely scattered points of high density showing a large proportion of hydrogen atoms in the molecular structure, indicating the importance of van der Waals contacts in the molecular packing. The N⋯H/H⋯N intermolecular contacts are identified as making a notable contribution to the total Hirshfeld surface comprising about 6.9%. However, the C—H⋯N intermolecular interactions are not prominent in the packing as the separations are greater than the van der Waals radii.

Figure 5
3-D Hirshfeld surfaces (showing d_norm, d_i and d_e) and 2-D fingerprint plots.

Synthesis and crystallization

A mixture of 1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one (1 mmol) and 4-methylbenzaldehyde (1 mmol) was dissolved in ethanol followed by the addition of alcoholic NaOH. The mixture was stirred at room temperature for 1 h to afford (E)-5-(4-methylbenzylidene)-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones as a precipitate, which was filtered, dried and recrystallized from ethanol: yield: 99%, m.p. 172–175°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₁H₁₈N₂O
M_r	314.37
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	30.3989 (15), 8.7177 (5), 14.0581 (7)
β (°)	115.367 (2)
V (Å³)	3366.3 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.08
Crystal size (mm)	0.20 × 0.20 × 0.18

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	22457, 2948, 2557
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.126, 1.07
No. of reflections	2948
No. of parameters	219
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.18
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2158365

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002838/tk4075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314622002838/tk4075Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314622002838/tk4075Isup3.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: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012), Mercury (Macrae et al., 2020) and PLATON (Spek, 2020); software used to prepare material for publication: SHELXL (Sheldrick, 2015b).

(E)-5-(4-Methylbenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one top

Crystal data top

C₂₁H₁₈N₂O	F(000) = 1328
M_r = 314.37	D_x = 1.241 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.3989 (15) Å	Cell parameters from 3243 reflections
b = 8.7177 (5) Å	θ = 28.7–1.8°
c = 14.0581 (7) Å	µ = 0.08 mm⁻¹
β = 115.367 (2)°	T = 293 K
V = 3366.3 (3) Å³	Block, colourless
Z = 8	0.20 × 0.20 × 0.18 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2557 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.048
Graphite monochromator	θ_max = 25.0°, θ_min = 2.9°
ω and φ scans	h = −36→36
22457 measured reflections	k = −10→10
2948 independent reflections	l = −16→16

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)] = 0.044	H-atom parameters constrained
wR(F²) = 0.126	w = 1/[σ²(F_o²) + (0.0626P)² + 1.8343P] where P = (F_o² + 2F_c²)/3
S = 1.07	(Δ/σ)_max < 0.001
2948 reflections	Δρ_max = 0.16 e Å⁻³
219 parameters	Δρ_min = −0.17 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.075 (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.

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

	x	y	z	U_iso*/U_eq
C1	0.67927 (8)	0.0162 (3)	1.06046 (15)	0.0789 (6)
H1	0.6816	−0.0935	1.0667	0.118*
H9	0.6614	0.0543	1.0977	0.118*
H10	0.7114	0.0599	1.0900	0.118*
C2	0.65323 (6)	0.0598 (2)	0.94602 (13)	0.0543 (4)
C3	0.66930 (6)	0.1813 (2)	0.90557 (14)	0.0586 (5)
H11	0.6970	0.2352	0.9496	0.070*
C4	0.64503 (6)	0.2237 (2)	0.80118 (14)	0.0550 (4)
H6	0.6572	0.3038	0.7758	0.066*
C5	0.60276 (5)	0.14887 (18)	0.73320 (12)	0.0450 (4)
C6	0.57687 (6)	0.20157 (19)	0.62334 (12)	0.0487 (4)
H12	0.5965	0.2260	0.5899	0.058*
C7	0.52919 (6)	0.21900 (18)	0.56538 (11)	0.0445 (4)
C8	0.48996 (6)	0.1884 (2)	0.60232 (12)	0.0516 (4)
H13	0.5052	0.1753	0.6781	0.062*
H14	0.4736	0.0931	0.5713	0.062*
C9	0.45177 (5)	0.3169 (2)	0.57388 (11)	0.0462 (4)
H15	0.4246	0.2838	0.5876	0.055*
H16	0.4660	0.4074	0.6160	0.055*
C10	0.43483 (5)	0.35272 (17)	0.45978 (11)	0.0416 (4)
C11	0.34983 (5)	0.45572 (19)	0.40541 (12)	0.0487 (4)
C12	0.35632 (6)	0.5344 (2)	0.49555 (13)	0.0541 (4)
H4	0.3875	0.5536	0.5471	0.065*
C13	0.31616 (7)	0.5847 (2)	0.50901 (16)	0.0657 (5)
H3	0.3205	0.6369	0.5701	0.079*
C14	0.27001 (7)	0.5582 (3)	0.43271 (17)	0.0761 (6)
H2	0.2431	0.5928	0.4417	0.091*
C15	0.51236 (6)	0.27563 (18)	0.45440 (11)	0.0449 (4)
C16	0.46258 (6)	0.32941 (18)	0.40502 (11)	0.0440 (4)
C17	0.43202 (6)	0.3710 (2)	0.30018 (12)	0.0518 (4)
H5	0.4413	0.3674	0.2453	0.062*
C18	0.61226 (6)	−0.01863 (19)	0.87812 (13)	0.0545 (4)
H8	0.6013	−0.1025	0.9029	0.065*
C19	0.58722 (6)	0.02523 (18)	0.77400 (13)	0.0509 (4)
H7	0.5595	−0.0287	0.7304	0.061*
C20	0.30333 (6)	0.4275 (3)	0.32794 (14)	0.0679 (5)
H18	0.2989	0.3743	0.2671	0.081*
C21	0.26374 (7)	0.4799 (3)	0.34264 (17)	0.0825 (7)
H17	0.2324	0.4620	0.2910	0.099*
N1	0.39101 (4)	0.40554 (15)	0.38972 (9)	0.0463 (3)
N2	0.38894 (5)	0.41551 (17)	0.28944 (10)	0.0550 (4)
O1	0.53899 (4)	0.27719 (16)	0.40893 (9)	0.0624 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0871 (14)	0.0832 (14)	0.0504 (11)	0.0112 (11)	0.0142 (10)	0.0108 (10)
C2	0.0548 (9)	0.0552 (10)	0.0472 (9)	0.0125 (7)	0.0163 (7)	0.0056 (7)
C3	0.0443 (8)	0.0577 (10)	0.0587 (10)	0.0017 (7)	0.0079 (7)	0.0034 (8)
C4	0.0442 (8)	0.0548 (10)	0.0624 (10)	0.0039 (7)	0.0192 (7)	0.0142 (8)
C5	0.0442 (8)	0.0470 (9)	0.0442 (8)	0.0097 (6)	0.0194 (6)	0.0042 (6)
C6	0.0527 (9)	0.0532 (9)	0.0453 (8)	0.0075 (7)	0.0259 (7)	0.0052 (7)
C7	0.0510 (8)	0.0484 (8)	0.0371 (7)	0.0075 (6)	0.0218 (6)	0.0038 (6)
C8	0.0522 (9)	0.0645 (10)	0.0409 (8)	0.0091 (7)	0.0226 (7)	0.0154 (7)
C9	0.0449 (8)	0.0614 (9)	0.0339 (7)	0.0044 (7)	0.0183 (6)	0.0071 (6)
C10	0.0443 (7)	0.0444 (8)	0.0329 (7)	−0.0007 (6)	0.0134 (6)	0.0012 (6)
C11	0.0432 (8)	0.0558 (9)	0.0430 (8)	0.0023 (7)	0.0146 (6)	0.0117 (7)
C12	0.0455 (8)	0.0617 (10)	0.0509 (9)	0.0024 (7)	0.0168 (7)	0.0010 (8)
C13	0.0602 (10)	0.0758 (13)	0.0659 (11)	0.0090 (9)	0.0317 (9)	0.0046 (9)
C14	0.0502 (10)	0.1054 (17)	0.0754 (14)	0.0144 (10)	0.0296 (10)	0.0224 (12)
C15	0.0550 (9)	0.0479 (9)	0.0366 (7)	0.0026 (7)	0.0244 (7)	−0.0001 (6)
C16	0.0547 (8)	0.0465 (8)	0.0313 (7)	0.0011 (6)	0.0191 (6)	0.0003 (6)
C17	0.0654 (10)	0.0582 (10)	0.0324 (8)	0.0072 (8)	0.0214 (7)	0.0027 (7)
C18	0.0589 (9)	0.0478 (9)	0.0540 (9)	0.0043 (7)	0.0217 (8)	0.0100 (7)
C19	0.0505 (9)	0.0457 (9)	0.0493 (9)	0.0013 (7)	0.0145 (7)	0.0004 (7)
C20	0.0513 (10)	0.0972 (15)	0.0440 (9)	−0.0042 (9)	0.0097 (7)	0.0053 (9)
C21	0.0429 (10)	0.128 (2)	0.0619 (12)	−0.0002 (11)	0.0088 (8)	0.0193 (13)
N1	0.0480 (7)	0.0545 (8)	0.0324 (6)	0.0029 (6)	0.0134 (5)	0.0035 (5)
N2	0.0639 (9)	0.0638 (9)	0.0313 (7)	0.0062 (7)	0.0146 (6)	0.0044 (6)
O1	0.0667 (8)	0.0851 (9)	0.0476 (7)	0.0143 (6)	0.0361 (6)	0.0098 (6)

Geometric parameters (Å, º) top

C1—C2	1.506 (2)	C10—C16	1.379 (2)
C1—H1	0.9600	C11—C12	1.379 (2)
C1—H9	0.9600	C11—C20	1.388 (2)
C1—H10	0.9600	C11—N1	1.430 (2)
C2—C18	1.382 (2)	C12—C13	1.384 (2)
C2—C3	1.386 (3)	C12—H4	0.9300
C3—C4	1.381 (2)	C13—C14	1.372 (3)
C3—H11	0.9300	C13—H3	0.9300
C4—C5	1.392 (2)	C14—C21	1.378 (3)
C4—H6	0.9300	C14—H2	0.9300
C5—C19	1.395 (2)	C15—O1	1.2279 (18)
C5—C6	1.474 (2)	C15—C16	1.446 (2)
C6—C7	1.333 (2)	C16—C17	1.412 (2)
C6—H12	0.9300	C17—N2	1.311 (2)
C7—C15	1.502 (2)	C17—H5	0.9300
C7—C8	1.514 (2)	C18—C19	1.383 (2)
C8—C9	1.538 (2)	C18—H8	0.9300
C8—H13	0.9700	C19—H7	0.9300
C8—H14	0.9700	C20—C21	1.383 (3)
C9—C10	1.4925 (19)	C20—H18	0.9300
C9—H15	0.9700	C21—H17	0.9300
C9—H16	0.9700	N1—N2	1.3867 (17)
C10—N1	1.3535 (18)

C2—C1—H1	109.5	C16—C10—C9	123.85 (13)
C2—C1—H9	109.5	C12—C11—C20	120.41 (16)
H1—C1—H9	109.5	C12—C11—N1	120.27 (13)
C2—C1—H10	109.5	C20—C11—N1	119.30 (15)
H1—C1—H10	109.5	C11—C12—C13	119.73 (16)
H9—C1—H10	109.5	C11—C12—H4	120.1
C18—C2—C3	117.79 (15)	C13—C12—H4	120.1
C18—C2—C1	121.21 (17)	C14—C13—C12	120.38 (19)
C3—C2—C1	120.99 (17)	C14—C13—H3	119.8
C4—C3—C2	121.26 (16)	C12—C13—H3	119.8
C4—C3—H11	119.4	C13—C14—C21	119.64 (18)
C2—C3—H11	119.4	C13—C14—H2	120.2
C3—C4—C5	121.32 (16)	C21—C14—H2	120.2
C3—C4—H6	119.3	O1—C15—C16	122.29 (13)
C5—C4—H6	119.3	O1—C15—C7	122.50 (14)
C4—C5—C19	117.09 (14)	C16—C15—C7	115.20 (12)
C4—C5—C6	119.64 (14)	C10—C16—C17	104.99 (13)
C19—C5—C6	123.27 (14)	C10—C16—C15	122.98 (13)
C7—C6—C5	128.94 (14)	C17—C16—C15	132.02 (14)
C7—C6—H12	115.5	N2—C17—C16	111.97 (14)
C5—C6—H12	115.5	N2—C17—H5	124.0
C6—C7—C15	118.02 (14)	C16—C17—H5	124.0
C6—C7—C8	125.46 (13)	C2—C18—C19	121.22 (16)
C15—C7—C8	116.51 (13)	C2—C18—H8	119.4
C7—C8—C9	113.58 (13)	C19—C18—H8	119.4
C7—C8—H13	108.8	C18—C19—C5	121.25 (15)
C9—C8—H13	108.8	C18—C19—H7	119.4
C7—C8—H14	108.8	C5—C19—H7	119.4
C9—C8—H14	108.8	C21—C20—C11	118.89 (19)
H13—C8—H14	107.7	C21—C20—H18	120.6
C10—C9—C8	107.83 (12)	C11—C20—H18	120.6
C10—C9—H15	110.1	C14—C21—C20	120.94 (18)
C8—C9—H15	110.1	C14—C21—H17	119.5
C10—C9—H16	110.1	C20—C21—H17	119.5
C8—C9—H16	110.1	C10—N1—N2	111.28 (12)
H15—C9—H16	108.5	C10—N1—C11	130.21 (12)
N1—C10—C16	106.89 (12)	N2—N1—C11	118.44 (12)
N1—C10—C9	129.20 (13)	C17—N2—N1	104.86 (12)

C18—C2—C3—C4	0.6 (3)	O1—C15—C16—C10	−168.78 (15)
C1—C2—C3—C4	−178.75 (18)	C7—C15—C16—C10	10.8 (2)
C2—C3—C4—C5	1.8 (3)	O1—C15—C16—C17	10.0 (3)
C3—C4—C5—C19	−2.7 (2)	C7—C15—C16—C17	−170.40 (16)
C3—C4—C5—C6	177.62 (15)	C10—C16—C17—N2	−0.38 (19)
C4—C5—C6—C7	−137.43 (18)	C15—C16—C17—N2	−179.36 (16)
C19—C5—C6—C7	42.9 (3)	C3—C2—C18—C19	−1.9 (3)
C5—C6—C7—C15	179.80 (15)	C1—C2—C18—C19	177.42 (17)
C5—C6—C7—C8	0.7 (3)	C2—C18—C19—C5	0.9 (3)
C6—C7—C8—C9	133.31 (17)	C4—C5—C19—C18	1.3 (2)
C15—C7—C8—C9	−45.8 (2)	C6—C5—C19—C18	−178.96 (15)
C7—C8—C9—C10	49.38 (18)	C12—C11—C20—C21	0.1 (3)
C8—C9—C10—N1	150.39 (16)	N1—C11—C20—C21	−178.39 (18)
C8—C9—C10—C16	−26.6 (2)	C13—C14—C21—C20	0.0 (4)
C20—C11—C12—C13	0.4 (3)	C11—C20—C21—C14	−0.3 (3)
N1—C11—C12—C13	178.88 (16)	C16—C10—N1—N2	0.89 (17)
C11—C12—C13—C14	−0.7 (3)	C9—C10—N1—N2	−176.49 (15)
C12—C13—C14—C21	0.5 (3)	C16—C10—N1—C11	−176.18 (15)
C6—C7—C15—O1	14.8 (2)	C9—C10—N1—C11	6.4 (3)
C8—C7—C15—O1	−166.01 (16)	C12—C11—N1—C10	36.0 (2)
C6—C7—C15—C16	−164.78 (15)	C20—C11—N1—C10	−145.48 (17)
C8—C7—C15—C16	14.4 (2)	C12—C11—N1—N2	−140.90 (16)
N1—C10—C16—C17	−0.32 (17)	C20—C11—N1—N2	37.6 (2)
C9—C10—C16—C17	177.24 (15)	C16—C17—N2—N1	0.89 (19)
N1—C10—C16—C15	178.78 (14)	C10—N1—N2—C17	−1.10 (18)
C9—C10—C16—C15	−3.7 (2)	C11—N1—N2—C17	176.35 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C6—H12···O1	0.93	2.43	2.806 (2)	104
C12—H4···O1ⁱ	0.93	2.52	3.312 (2)	143
C17—H5···O1ⁱⁱ	0.93	2.60	3.5081 (19)	164
C18—H8···O1ⁱⁱⁱ	0.93	2.46	3.325 (2)	155

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

Acknowledgements

JS and RV thank the management of The Madura College for their constant support and encouragement. The authors' contributions are as follows: Conceptualization, CSM; methodology, CSM, SA; investigation, CSM, RVP; synthesis, X-ray, analysis and validation, SA; writing (original draft), CSM; writing (review and editing of the manuscript), SRB; visualization, JS; resources, RVP, SRR; supervision, JS; project administration, SRB.

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