(E)-5-(4-Chloro­benzyl­idene)-1-phenyl-4,5,6,7-tetra­hydro-1H-indazol-4-one: crystal structure and Hirshfeld surface analysis

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

doi:10.1107/S2414314621011950

organic compounds

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ISSN: 2414-3146

Volume 6| Part 11| November 2021| x211195

https://doi.org/10.1107/S2414314621011950

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(E)-5-(4-Chlorobenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H-indazol-4-one: crystal structure and Hirshfeld surface analysis

C. Selva Meenatchi,^a S. Athimoolam,^b J. Suresh,^a S. Raja Rubina,^c R. Ranjith Kumar ^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 2 November 2021; accepted 10 November 2021; online 16 November 2021)

In the title compound, C₂₀H₁₅ClN₂O, the non-aromatic six-membered ring adopts a distorted envelope conformation with methylene-C atom nearest to the five-membered ring being the flap atom. The dihedral angle between the phenyl and chlorobenzene rings is 74.5 (1)°. The heterocyclic ring forms dihedral angles of 37.9 (1) and 64.3 (1)° with the phenyl and chlorobenzene rings, respectively. In the crystal, weak C—H⋯O interactions feature predominantly within the three-dimensional architecture. The intermolecular interactions are further analysed with the calculation of the Hirshfeld surfaces highlighting the prominent role of C—H⋯O interactions, along with H⋯H (36.8%) and C⋯H/H⋯C (26.5%) contacts.

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

CCDC reference: 2121290

Structure description

Many heterocyclic compounds are studied for their biological and pharmacological activities. For example, 1,2-diazole derivatives are known to possess anti-depressant, anti-viral, anti-inflammatory and anti-cancer activities (Popat et al., 2003 ; Faisal et al., 2019 ). The crystal and molecular structure of one such indazole derivative, namely, (E)-5-(4-chlorobenzylidene)-1-phenyl-4,5,6,7-tetrahydro-1H- indazol-4-one, is reported herein.

The non-aromatic six-membered ring adopts a distorted envelope conformation with the methylene-C10 atom being the flap atom, Fig. 1. The heterocyclic ring forms dihedral angles of 37.9 (1) and 64.3 (1)° with the phenyl and chlorobenzene rings, respectively. The dihedral angle between the pendant rings is 74.5 (1)°. The molecular structure features a weak intramolecular interaction through C14—H14⋯O1 (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C14—H14⋯O1	0.93	2.43	2.804 (3)	104
C5—H5⋯O1ⁱ	0.93	2.53	3.320 (3)	143
C7—H7⋯O1ⁱⁱ	0.93	2.59	3.493 (3)	163
C17—H17⋯O1ⁱⁱⁱ	0.93	2.40	3.260 (3)	154
C2—H2⋯Cl1^iv	0.93	2.90	3.633 (3)	137
Symmetry codes: (i) ; (ii) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (iii) $[x, -y+2, z+{\script{1\over 2}}]$ ; (iv) $[x-{\script{1\over 2}}, y-{\script{1\over 2}}, z-1]$ .

Figure 1
The molecular structure of the title compound, showing 50% probability displacement ellipsoids

The molecular packing features two ring motifs, viz., R₂²(10) and R₂²(16) (Bernstein et al., 1995 ), each around an inversion centre, through two C—H⋯O interactions, i.e. C7—H7⋯O1ⁱⁱ and C5—H5⋯O1ⁱ, respectively, Fig. 2; for symmetry codes, refer to Table 1. The centrosymmetric dimers thus formed are connected through two C—H⋯X interactions, viz., C17—H17⋯Oⁱⁱⁱ and C2—H2⋯Cl^iv, leading to chain C(8) and C(15) motifs, respectively. The first named interaction serves to connect the molecules along the along [001] and the latter along [101], Fig. 3. Clearly, the carbonyl-O1 atom plays a pivotal role in the supramolecular assembly.

Figure 2
A view of the unit-cell contents viewed in projection down the b-axis.

Figure 3
Views of significant C—H⋯X interactions (X = O or Cl) shown as dashed lines forming (a) an R₂²(10) ring motif, (b) an R₂²(16) ring, (c) a C(8) chain motif and (d) a C(15) chain.

The intermolecular interactions in the crystal state can be visualized through the calculation of the Hirshfeld surfaces and associated two-dimensional fingerprint plots. These were generated by Crystal Explorer (Wolff et al., 2012 ). The Hirshfeld surface is colour-mapped with the normalized contact distance, d_norm, i.e. 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 distances from the surface to the nearest atom exterior (d_e) or interior (d_i) plots to the surface. The three-dimensional Hirshfeld surfaces and selected two-dimensional fingerprint plots (with percentage contributions) are given in Fig. 4.

Figure 4
Hirshfeld three-dimensional surfaces (showing d_norm, d_i and d_e) and selected two-dimensional fingerprint plots

The presence of spikes due to O⋯H/H⋯O interactions (8.6%) correspond to C—H⋯O intermolecular interactions, which feature predominantly within the crystalline assembly. The contribution of C⋯H/H⋯C contacts (26.5%), leading to a pair of well-defined wings, is also noteworthy. The H⋯H interactions contribute 36.8% with widely scattered points of high density, which is consistent with the large number of hydrogen atoms at the surface of the molecule. The Cl⋯H/H⋯Cl contacts also make a notable contribution to the total Hirshfeld surfaces, comprising about 12.9%. The large number of H⋯H, Cl⋯H/H⋯Cl, O⋯H/H⋯O interactions suggest that van der Waals interactions play a significant role in the packing in the crystal.

Synthesis and crystallization

A mixture of 1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-one, (1 mmol) and 4-chlorobenzaldehyde (1 mmol) was dissolved in ethanol followed by the addition of NaOH. The resulting mixture was stirred at room temperature for 1 h to afford (E)-5-(4-chlorobenzylidene)-1-phenyl-1,5,6,7-tetrahydro-4H-indazol-4-ones as the precipitate. This was filtered off and recrystallized from ethanol to afford colourless crystals; yield: 95%, m.p. 183–184°C.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₀H₁₅ClN₂O
M_r	334.79
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	293
a, b, c (Å)	30.4808 (16), 8.6604 (5), 14.0457 (7)
β (°)	115.071 (2)
V (Å³)	3358.4 (3)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.24
Crystal size (mm)	0.22 × 0.20 × 0.16

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	42189, 2949, 2353
R_int	0.056
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.146, 1.12
No. of reflections	2949
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.44
Computer programs: APEX2 and SAINT (Bruker, 2009 ), SHELXT (Sheldrick, 2015a ), SHELXL97 and SHELXL2018 (Sheldrick, 2015b ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2020 ) and PLATON (Spek, 2020 ).

Structural data

CCDC reference: 2121290

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314621011950/tk4071sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314621011950/tk4071Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314621011950/tk4071Isup3.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: SHELXL2018 (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: SHELXL97 (Sheldrick, 2015b).

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

Crystal data top

C₂₀H₁₅ClN₂O	F(000) = 1392
M_r = 334.79	D_x = 1.324 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 30.4808 (16) Å	Cell parameters from 2246 reflections
b = 8.6604 (5) Å	θ = 2.9–23.5°
c = 14.0457 (7) Å	µ = 0.24 mm⁻¹
β = 115.071 (2)°	T = 293 K
V = 3358.4 (3) Å³	Block, colourless
Z = 8	0.22 × 0.20 × 0.16 mm

Data collection top

Bruker SMART APEXII CCD diffractometer	R_int = 0.056
Radiation source: fine-focus sealed tube	θ_max = 25.5°, θ_min = 3.2°
ω and φ scans	h = −36→36
42189 measured reflections	k = −10→10
2949 independent reflections	l = −16→16
2353 reflections with I > 2σ(I)

Refinement top

Refinement on F²	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H-atom parameters constrained
R[F² > 2σ(F²)] = 0.051	w = 1/[σ²(F_o²) + (0.0578P)² + 3.7997P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.146	(Δ/σ)_max < 0.001
S = 1.12	Δρ_max = 0.39 e Å⁻³
2949 reflections	Δρ_min = −0.44 e Å⁻³
218 parameters	Extinction correction: SHELXL2018 (Sheldrick, 2015b), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
0 restraints	Extinction coefficient: 0.0169 (15)

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. The hydrogen atoms were included in their geometrically calculated positions and refined isotropically with C—H = 0.93 or 0.97 Å and U_iso(H) = 1.2U_eq(C).

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

	x	y	z	U_iso*/U_eq
C1	0.30506 (10)	0.5737 (4)	0.3310 (2)	0.0788 (9)
H1	0.3008	0.6269	0.2702	0.095*
C2	0.26559 (11)	0.5226 (5)	0.3465 (3)	0.0966 (12)
H2	0.2345	0.5414	0.2953	0.116*
C3	0.27141 (10)	0.4449 (4)	0.4359 (3)	0.0853 (9)
H3	0.2445	0.4113	0.4450	0.102*
C4	0.31708 (10)	0.4167 (3)	0.5118 (2)	0.0706 (7)
H4	0.3212	0.3647	0.5729	0.085*
C5	0.35712 (9)	0.4656 (3)	0.49759 (19)	0.0580 (6)
H5	0.3881	0.4453	0.5487	0.070*
C6	0.35095 (8)	0.5440 (3)	0.40771 (17)	0.0531 (6)
C7	0.43290 (9)	0.6267 (3)	0.30115 (16)	0.0558 (6)
H7	0.4422	0.6301	0.2461	0.067*
C8	0.46319 (8)	0.6698 (3)	0.40535 (15)	0.0466 (5)
C9	0.43539 (8)	0.6472 (2)	0.46043 (15)	0.0447 (5)
C10	0.45229 (8)	0.6841 (3)	0.57428 (15)	0.0490 (5)
H10A	0.4664	0.5931	0.6165	0.059*
H10B	0.4252	0.7178	0.5882	0.059*
C11	0.49020 (8)	0.8128 (3)	0.60228 (17)	0.0536 (6)
H11A	0.4739	0.9090	0.5720	0.064*
H11B	0.5055	0.8254	0.6780	0.064*
C12	0.52910 (8)	0.7832 (3)	0.56429 (16)	0.0460 (5)
C13	0.51238 (8)	0.7266 (3)	0.45363 (16)	0.0480 (5)
C14	0.57663 (8)	0.8010 (3)	0.62150 (17)	0.0503 (5)
H14	0.5962	0.7770	0.5876	0.060*
C15	0.60225 (8)	0.8534 (3)	0.73111 (17)	0.0483 (5)
C16	0.58651 (9)	0.9775 (3)	0.77156 (18)	0.0545 (6)
H16	0.5589	1.0315	0.7278	0.065*
C17	0.61102 (9)	1.0221 (3)	0.87534 (19)	0.0599 (6)
H17	0.6002	1.1056	0.9011	0.072*
C18	0.65138 (9)	0.9423 (3)	0.93968 (19)	0.0617 (7)
C19	0.66861 (9)	0.8207 (3)	0.9027 (2)	0.0666 (7)
H19	0.6962	0.7676	0.9473	0.080*
C20	0.64429 (8)	0.7783 (3)	0.7983 (2)	0.0595 (6)
H20	0.6563	0.6978	0.7725	0.071*
N1	0.39190 (7)	0.5928 (2)	0.39106 (13)	0.0502 (5)
N2	0.39011 (8)	0.5812 (2)	0.29111 (14)	0.0588 (5)
O1	0.53879 (6)	0.7264 (2)	0.40725 (12)	0.0669 (5)
Cl1	0.68147 (4)	0.99499 (12)	1.07100 (6)	0.1050 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0585 (16)	0.120 (3)	0.0481 (14)	0.0063 (16)	0.0129 (12)	−0.0020 (15)
C2	0.0489 (15)	0.156 (3)	0.0687 (19)	−0.0017 (18)	0.0097 (14)	−0.014 (2)
C3	0.0570 (16)	0.119 (3)	0.082 (2)	−0.0160 (17)	0.0322 (15)	−0.0208 (19)
C4	0.0634 (16)	0.0813 (19)	0.0700 (17)	−0.0088 (14)	0.0310 (14)	−0.0017 (14)
C5	0.0515 (13)	0.0658 (15)	0.0528 (13)	−0.0032 (11)	0.0185 (11)	−0.0002 (11)
C6	0.0450 (12)	0.0638 (14)	0.0472 (12)	−0.0030 (10)	0.0163 (10)	−0.0126 (11)
C7	0.0719 (16)	0.0620 (14)	0.0346 (11)	−0.0053 (12)	0.0235 (11)	−0.0014 (10)
C8	0.0588 (12)	0.0498 (12)	0.0326 (10)	−0.0014 (10)	0.0205 (9)	−0.0006 (9)
C9	0.0512 (12)	0.0463 (12)	0.0342 (10)	0.0015 (9)	0.0159 (9)	−0.0006 (8)
C10	0.0503 (12)	0.0643 (14)	0.0354 (10)	−0.0041 (10)	0.0208 (9)	−0.0065 (10)
C11	0.0565 (13)	0.0652 (14)	0.0418 (11)	−0.0061 (11)	0.0234 (10)	−0.0131 (10)
C12	0.0542 (12)	0.0478 (12)	0.0389 (11)	−0.0037 (10)	0.0225 (9)	−0.0017 (9)
C13	0.0612 (13)	0.0496 (12)	0.0380 (10)	−0.0013 (10)	0.0256 (10)	0.0011 (9)
C14	0.0583 (13)	0.0526 (13)	0.0458 (12)	−0.0079 (10)	0.0278 (10)	−0.0038 (10)
C15	0.0494 (12)	0.0484 (12)	0.0476 (12)	−0.0080 (10)	0.0211 (10)	−0.0035 (9)
C16	0.0570 (13)	0.0497 (13)	0.0512 (13)	−0.0031 (10)	0.0175 (11)	−0.0019 (10)
C17	0.0673 (15)	0.0550 (14)	0.0565 (14)	−0.0070 (12)	0.0253 (12)	−0.0130 (11)
C18	0.0647 (15)	0.0654 (16)	0.0472 (13)	−0.0158 (12)	0.0162 (12)	−0.0066 (11)
C19	0.0528 (13)	0.0643 (16)	0.0637 (16)	−0.0029 (12)	0.0064 (12)	−0.0019 (13)
C20	0.0498 (13)	0.0578 (14)	0.0671 (15)	−0.0046 (11)	0.0211 (12)	−0.0139 (12)
N1	0.0526 (10)	0.0598 (12)	0.0343 (9)	−0.0020 (9)	0.0146 (8)	−0.0049 (8)
N2	0.0689 (13)	0.0686 (13)	0.0332 (9)	−0.0044 (10)	0.0163 (9)	−0.0038 (9)
O1	0.0719 (11)	0.0929 (14)	0.0488 (9)	−0.0152 (10)	0.0382 (9)	−0.0104 (9)
Cl1	0.1194 (8)	0.1189 (8)	0.0501 (4)	−0.0154 (6)	0.0101 (4)	−0.0184 (4)

Geometric parameters (Å, º) top

C1—C6	1.380 (3)	C10—H10B	0.9700
C1—C2	1.383 (4)	C11—C12	1.514 (3)
C1—H1	0.9300	C11—H11A	0.9700
C2—C3	1.367 (5)	C11—H11B	0.9700
C2—H2	0.9300	C12—C14	1.335 (3)
C3—C4	1.370 (4)	C12—C13	1.498 (3)
C3—H3	0.9300	C13—O1	1.232 (2)
C4—C5	1.384 (3)	C14—C15	1.472 (3)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.375 (3)	C15—C20	1.389 (3)
C5—H5	0.9300	C15—C16	1.393 (3)
C6—N1	1.428 (3)	C16—C17	1.382 (3)
C7—N2	1.312 (3)	C16—H16	0.9300
C7—C8	1.410 (3)	C17—C18	1.366 (4)
C7—H7	0.9300	C17—H17	0.9300
C8—C9	1.382 (3)	C18—C19	1.373 (4)
C8—C13	1.445 (3)	C18—Cl1	1.737 (2)
C9—N1	1.354 (3)	C19—C20	1.384 (3)
C9—C10	1.492 (3)	C19—H19	0.9300
C10—C11	1.532 (3)	C20—H20	0.9300
C10—H10A	0.9700	N1—N2	1.385 (2)

C6—C1—C2	118.6 (3)	C10—C11—H11A	108.8
C6—C1—H1	120.7	C12—C11—H11B	108.8
C2—C1—H1	120.7	C10—C11—H11B	108.8
C3—C2—C1	121.3 (3)	H11A—C11—H11B	107.7
C3—C2—H2	119.4	C14—C12—C13	117.88 (19)
C1—C2—H2	119.4	C14—C12—C11	125.50 (19)
C2—C3—C4	119.7 (3)	C13—C12—C11	116.62 (18)
C2—C3—H3	120.1	O1—C13—C8	122.14 (19)
C4—C3—H3	120.1	O1—C13—C12	122.5 (2)
C3—C4—C5	120.0 (3)	C8—C13—C12	115.31 (18)
C3—C4—H4	120.0	C12—C14—C15	128.6 (2)
C5—C4—H4	120.0	C12—C14—H14	115.7
C6—C5—C4	119.8 (2)	C15—C14—H14	115.7
C6—C5—H5	120.1	C20—C15—C16	117.5 (2)
C4—C5—H5	120.1	C20—C15—C14	119.6 (2)
C5—C6—C1	120.5 (2)	C16—C15—C14	122.9 (2)
C5—C6—N1	120.5 (2)	C17—C16—C15	121.3 (2)
C1—C6—N1	119.0 (2)	C17—C16—H16	119.3
N2—C7—C8	112.04 (19)	C15—C16—H16	119.3
N2—C7—H7	124.0	C18—C17—C16	119.3 (2)
C8—C7—H7	124.0	C18—C17—H17	120.3
C9—C8—C7	104.84 (19)	C16—C17—H17	120.3
C9—C8—C13	123.08 (18)	C17—C18—C19	121.3 (2)
C7—C8—C13	132.08 (19)	C17—C18—Cl1	119.5 (2)
N1—C9—C8	106.97 (18)	C19—C18—Cl1	119.2 (2)
N1—C9—C10	129.34 (19)	C18—C19—C20	119.0 (2)
C8—C9—C10	123.66 (19)	C18—C19—H19	120.5
C9—C10—C11	108.14 (18)	C20—C19—H19	120.5
C9—C10—H10A	110.1	C19—C20—C15	121.4 (2)
C11—C10—H10A	110.1	C19—C20—H20	119.3
C9—C10—H10B	110.1	C15—C20—H20	119.3
C11—C10—H10B	110.1	C9—N1—N2	111.14 (18)
H10A—C10—H10B	108.4	C9—N1—C6	129.95 (17)
C12—C11—C10	113.84 (19)	N2—N1—C6	118.87 (17)
C12—C11—H11A	108.8	C7—N2—N1	105.00 (17)

C6—C1—C2—C3	0.3 (5)	C11—C12—C13—C8	−15.1 (3)
C1—C2—C3—C4	0.0 (6)	C13—C12—C14—C15	−179.6 (2)
C2—C3—C4—C5	−0.6 (5)	C11—C12—C14—C15	−0.8 (4)
C3—C4—C5—C6	0.8 (4)	C12—C14—C15—C20	137.4 (3)
C4—C5—C6—C1	−0.4 (4)	C12—C14—C15—C16	−43.2 (4)
C4—C5—C6—N1	−178.9 (2)	C20—C15—C16—C17	−1.6 (3)
C2—C1—C6—C5	−0.1 (4)	C14—C15—C16—C17	179.0 (2)
C2—C1—C6—N1	178.3 (3)	C15—C16—C17—C18	−0.3 (4)
N2—C7—C8—C9	0.0 (3)	C16—C17—C18—C19	1.3 (4)
N2—C7—C8—C13	−179.9 (2)	C16—C17—C18—Cl1	−178.43 (19)
C7—C8—C9—N1	0.5 (2)	C17—C18—C19—C20	−0.3 (4)
C13—C8—C9—N1	−179.6 (2)	Cl1—C18—C19—C20	179.4 (2)
C7—C8—C9—C10	−177.5 (2)	C18—C19—C20—C15	−1.7 (4)
C13—C8—C9—C10	2.3 (3)	C16—C15—C20—C19	2.7 (4)
N1—C9—C10—C11	−150.9 (2)	C14—C15—C20—C19	−177.9 (2)
C8—C9—C10—C11	26.7 (3)	C8—C9—N1—N2	−0.9 (2)
C9—C10—C11—C12	−48.7 (3)	C10—C9—N1—N2	177.0 (2)
C10—C11—C12—C14	−133.4 (2)	C8—C9—N1—C6	176.8 (2)
C10—C11—C12—C13	45.5 (3)	C10—C9—N1—C6	−5.3 (4)
C9—C8—C13—O1	169.9 (2)	C5—C6—N1—C9	−37.2 (4)
C7—C8—C13—O1	−10.2 (4)	C1—C6—N1—C9	144.3 (3)
C9—C8—C13—C12	−9.1 (3)	C5—C6—N1—N2	140.4 (2)
C7—C8—C13—C12	170.7 (2)	C1—C6—N1—N2	−38.1 (3)
C14—C12—C13—O1	−15.3 (3)	C8—C7—N2—N1	−0.5 (3)
C11—C12—C13—O1	165.8 (2)	C9—N1—N2—C7	0.9 (3)
C14—C12—C13—C8	163.8 (2)	C6—N1—N2—C7	−177.1 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C14—H14···O1	0.93	2.43	2.804 (3)	104
C5—H5···O1ⁱ	0.93	2.53	3.320 (3)	143
C7—H7···O1ⁱⁱ	0.93	2.59	3.493 (3)	163
C17—H17···O1ⁱⁱⁱ	0.93	2.40	3.260 (3)	154
C2—H2···Cl1^iv	0.93	2.90	3.633 (3)	137

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

Acknowledgements

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

References

Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N. L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573. CrossRef CAS Web of Science Google Scholar
Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Faisal, M., Saeed, A., Hussain, S., Dar, P. & Larik, F. A. (2019). J. Chem. Sci. 131(8), 1–30. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Macrae, C. F., Sovago, I., Cottrell, S. J., Galek, P. T. A., McCabe, P., Pidcock, E., Platings, M., Shields, G. P., Stevens, J. S., Towler, M. & Wood, P. A. (2020). J. Appl. Cryst. 53, 226–235. Web of Science CrossRef CAS IUCr Journals Google Scholar
Popat, K. H., Nimavat, K. S., Vasoya, S. L. & Joshi, H. S. (2003). Indian J. Chem. Sect. B, 42, 1497–1501. Google Scholar
Sheldrick, G. M. (2015a). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2015b). Acta Cryst. C71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2020). Acta Cryst. E76, 1–11. Web of Science CrossRef IUCr Journals Google Scholar
Wolff, S. K., Grimwood, D. J., McKinnon, J. J., Turner, M. J., Jayatilaka, D. & Spackman, M. A. (2012). Crystal Explorer, University of Western Australia, Crawley. Google Scholar

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