4-Cyclo­hexyl-1-(2-meth­oxy­benzo­yl)thio­semi­carbazide with an unknown solvent

Chaurasia, R.; Bharti, A.; Butcher, R.J.; Wikaira, J.L.; Bharty, M.K.

doi:10.1107/S2414314618003838

organic compounds

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ISSN: 2414-3146

Volume 3| Part 3| March 2018| x180383

https://doi.org/10.1107/S2414314618003838

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4-Cyclohexyl-1-(2-methoxybenzoyl)thiosemicarbazide with an unknown solvent

Rahul Chaurasia,^a Akhilesh Bharti,^b Ray J. Butcher,^c Jan L. Wikaira ^d and Manoj K. Bharty ^a ^*

^aDepartment of Chemistry, Banaras Hindu University, Varanasi 221 005, India, ^bDepartment of Chemistry, Kirori Mal College, University of Delhi, Delhi-110007, India, ^cDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA, and ^dDepartment of Chemistry, University of Canterbury, PO Box 4800, 8410, New Zealand
^*Correspondence e-mail: mkbharty@bhu.ac.in

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 6 February 2018; accepted 5 March 2018; online 13 March 2018)

In the title compound, C₁₅H₂₁N₃O₂S, a short intramolecular N—H⋯O hydrogen bond generates an S(6) ring. The molecule is twisted with a dihedral angle between the benzene ring and the mean plane of the cyclohexyl ring being 58.90 (6)°. In the crystal, inversion dimers are formed with each molecule linked to the other by two N—H(H)⋯O hydrogen bonds to the same acceptor, generating R₂¹(6) loops. A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON [Spek (2015 ). Acta Cryst. C71, 9–18]. The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s).

Keywords: crystal structure; thiosemicarbazide; N—H⋯O hydrogen bonding; inversion dimers.

CCDC reference: 1819711

Structure description

Thiosemicarbazides are a class of organic compounds which are known not only for their various biological activities but also as metal-chelating agents (Siddiqui & Singh, 2003 ; Castiñeiras et al., 2012 ; Singh et al., 2014 ). Thiosemicarbazide is the simplest representative of such ligands having both nitrogen and sulfur atoms as donors. Thiosemicarbazide and substituted thiosemicarbazides are an important class of intermediates used for the synthesis of nitrogen–sulfur or nitrogen–oxygen heterocyclic compounds (Hovsepian et al., 2004 ; Paswan et al., 2015 ). Substituted thiosemicarbazides are biologically versatile compounds displaying a variety of biological effects (Bharti et al., 2016 ; Plech et al., 2011 ; Siwek et al., 2011 ). The addition of hydrazides to various isothiocyanates is a convenient method for the synthesis of substituted thiosemicarbazides. As part of our studies in this area, we have synthesized the title compound and herein report on its crystal structure.

In the title compound, the dihedral angle of 58.90 (6)° between the benzene ring and the mean plane of the cyclohexyl ring indicates that the molecule is twisted (Fig. 1). A short intramolecular N—H⋯O hydrogen bond generates an S(6) ring (Fig. 1, Table 1). The lengths of the C8=O1 [1.2426 (13) Å] and C9=S1 [1.6737 (11) Å] double bonds are in agreement with bond lengths in related compounds (Nath et al., 2015 ; Dulare et al., 2011 ). The C—N bond lengths, N1—C8 1.3321 (13), N2—C9 1.3611 (13) and N3—C10 1.4593 (14) Å, are similar to standard C—N single bonds.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O2	0.88	1.90	2.5907 (12)	135
N2—H2A⋯O1ⁱ	0.88	2.11	2.8523 (12)	142
N3—H3B⋯O1ⁱ	0.88	2.04	2.8607 (12)	155
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 1
The molecular structure of the title compound, with atom labelling and displacement ellipsoids drawn at the 30% probability level. The intramolecular N—H⋯O hydrogen bond is shown as a dashed line (see Table 1

In the crystal, inversion dimers are formed with each molecule linked to the other by two N—H(H)⋯O hydrogen bonds to the same acceptor, generating $[R_{2}^{1}]$ (6) loops (Fig. 2, Table 1). The overall crystal packing is illustrated in Fig. 3.

Figure 2
A view of the N—H⋯O hydrogen-bonding interactions (dashed lines; Table l) involving the same acceptor atom, forming an inversion dimer. Unlabelled atoms are related to labelled ones by the symmetry operation −x + 1, −y + 1, −z + 1.

Figure 3
A view along the a axis of the crystal packing of the title compound, showing the N—H⋯O interactions as dashed lines (see Table 1

A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015). The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s). The region occupied by the disordered solvent is illustrated in Fig. 4, drawn using Mercury (Macrae et al., 2008 ).

Figure 4
A view along the c axis of the crystal packing of the title compound, showing the region occupied by the disordered solvent (Mercury; Macrae et al., 2008

Synthesis and crystallization

The synthesis of the title compound is illustrated in Fig. 5. Methyl-2-methoxy benzoate (1.436 ml, 10 mmol) and hydrazine hydrate (0.485 ml, 10 mmol) were refluxed for 5 h and kept for overnight. The white solid 2-methoxy benzoic acid hydrazide was obtained upon cooling and filtered off, washed with water and and thereafter with ether. A mixture of 2-methoxy benzoic acid hydrazide (1.660 g, 10 mmol) and cyclohexyl isothiocyanate (1.417 ml, 10 mmol) in absolute ethanol (20 ml) was refluxed for 4 h. The solid obtained upon cooling was filtered off and washed with water and thereafter with ether. The above solid was dissolved in methanol and kept for crystallization. Colorless crystals of the title compound were obtained after 10 days (yield: 60%, m.p. 468 K). Analysis calculated for C₁₅H₂₁N₃O₂S (307.41): C, 58.55; H, 6.83; N, 13.66, S, 10.40%; Found. C, 58.05; H, 6.95; N, 13.15, S, 10.60%. IR (Selected, KBr): ν(NH) 3281, 3188; ν(C=O) 1633; ν(N—N) 1046; ν(C=S) 975 cm⁻¹. ¹H NMR (DMSO d₆; δ p.p.m.): 10.45, 9.94 (s, 2H, NH), 7.48–7.07 (m, 4H, aromatic), 3.81 (s, 3H, OCH₃), 3.27 (s, 1H, NH), 2.46–1.51 (cyclohexyl protons). ¹³C NMR (DMSO-d_6; δ p.p.m.): 180.1 (C9), 163.0 (C8), 157.7 (C2), 133.9 (C4), 130.8 (C6), 122.3 (C5), 121.1 (C3), 112.9 (C1), 56.5 (C7), 49.0 (C10), 39.6 (C11, C15), 32.8 (C13), 25.1 (C12, C14).

Figure 5
The reaction scheme showing the synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. A region of disordered electron density was corrected for using the SQUEEZE routine in PLATON (Spek, 2015). The given chemical formula and other crystal data do not take into account the unknown solvent molecule(s).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₂₁N₃O₂S
M_r	307.41
Crystal system, space group	Orthorhombic, Pccn
Temperature (K)	100
a, b, c (Å)	29.5823 (10), 15.1971 (8), 7.4303 (2)
V (Å³)	3340.4 (2)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.20
Crystal size (mm)	0.35 × 0.31 × 0.18

Data collection
Diffractometer	Rigaku OD SuperNova, Dual, Cu at zero, Atlas
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ )
T_min, T_max	0.766, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	23969, 8579, 5943
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.865

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.051, 0.141, 1.01
No. of reflections	8579
No. of parameters	191
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.49
Computer programs: CrysAlis PRO (Rigaku OD, 2015 $[Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England.]$ ), SHELXT (Sheldrick, 2015a ), SHELXL2014 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Structural data

CCDC reference: 1819711

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2414314618003838/su5423sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314618003838/su5423Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis PRO (Rigaku OD, 2015); cell refinement: CrysAlis PRO (Rigaku OD, 2015); data reduction: CrysAlis PRO (Rigaku OD, 2015); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-Cyclohexyl-1-(2-methoxybenzoyl)thiosemicarbazide top

Crystal data top

C₁₅H₂₁N₃O₂S	D_x = 1.223 Mg m⁻³
M_r = 307.41	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pccn	Cell parameters from 5858 reflections
a = 29.5823 (10) Å	θ = 4.1–36.9°
b = 15.1971 (8) Å	µ = 0.20 mm⁻¹
c = 7.4303 (2) Å	T = 100 K
V = 3340.4 (2) Å³	Block, colourless
Z = 8	0.35 × 0.31 × 0.18 mm
F(000) = 1312

Data collection top

Rigaku OD SuperNova, Dual, Cu at zero, Atlas diffractometer	8579 independent reflections
Radiation source: micro-focus sealed X-ray tube	5943 reflections with I > 2σ(I)
Detector resolution: 10.6501 pixels mm^-1	R_int = 0.038
ω scans	θ_max = 38.0°, θ_min = 3.4°
Absorption correction: multi-scan (CrysAlis PRO; Rigaku OD, 2015)	h = −51→32
T_min = 0.766, T_max = 1.000	k = −22→25
23969 measured reflections	l = −12→9

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)] = 0.051	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.141	H-atom parameters constrained
S = 1.00	w = 1/[σ²(F_o²) + (0.0573P)² + 0.9308P] where P = (F_o² + 2F_c²)/3
8579 reflections	(Δ/σ)_max = 0.001
191 parameters	Δρ_max = 0.57 e Å⁻³
0 restraints	Δρ_min = −0.49 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 included in calculated positions and refined as riding: (N—H = 0.88 Å, C—H = 0.95–1.00 Å with U_iso(H) = 1.5U_eq(C-methyl) and 1.2Ueq (C, N) for other H atoms.

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

	x	y	z	U_iso*/U_eq
S1	0.35005 (2)	0.45941 (2)	0.30736 (4)	0.02840 (8)
O1	0.51910 (3)	0.44865 (6)	0.30165 (10)	0.02145 (16)
N1	0.44576 (3)	0.42049 (6)	0.25602 (12)	0.01785 (16)
H1A	0.4245	0.3969	0.1885	0.021*
N2	0.43510 (3)	0.45797 (6)	0.41971 (12)	0.01968 (17)
H2A	0.4555	0.4622	0.5055	0.024*
N3	0.38838 (3)	0.54063 (7)	0.58855 (13)	0.02328 (19)
H3B	0.4134	0.5557	0.6450	0.028*
C1	0.49867 (3)	0.38567 (6)	0.01910 (13)	0.01554 (16)
O2	0.42318 (3)	0.34449 (6)	−0.04284 (11)	0.02289 (16)
C2	0.46703 (4)	0.34759 (7)	−0.09866 (13)	0.01771 (18)
C3	0.48083 (4)	0.31472 (7)	−0.26464 (15)	0.0219 (2)
H3A	0.4594	0.2887	−0.3435	0.026*
C4	0.52583 (4)	0.31993 (7)	−0.31475 (14)	0.0236 (2)
H4A	0.5351	0.2970	−0.4278	0.028*
C5	0.55740 (4)	0.35814 (7)	−0.20190 (14)	0.0213 (2)
H5A	0.5882	0.3618	−0.2369	0.026*
C6	0.54345 (4)	0.39094 (7)	−0.03713 (13)	0.01772 (18)
H6A	0.5651	0.4178	0.0397	0.021*
C7	0.39000 (4)	0.30595 (9)	−0.15849 (19)	0.0305 (3)
H7A	0.3601	0.3105	−0.1022	0.046*
H7B	0.3974	0.2439	−0.1786	0.046*
H7C	0.3898	0.3371	−0.2740	0.046*
C8	0.48867 (4)	0.42057 (7)	0.20168 (13)	0.01617 (17)
C9	0.39228 (4)	0.48821 (8)	0.44523 (13)	0.01948 (19)
C10	0.34575 (4)	0.57477 (8)	0.65855 (14)	0.0207 (2)
H10A	0.3240	0.5806	0.5562	0.025*
C11	0.35395 (4)	0.66559 (8)	0.73803 (16)	0.0227 (2)
H11A	0.3648	0.7058	0.6425	0.027*
H11B	0.3777	0.6618	0.8316	0.027*
C12	0.31070 (4)	0.70242 (8)	0.82077 (15)	0.0240 (2)
H12A	0.3173	0.7597	0.8786	0.029*
H12B	0.2881	0.7126	0.7246	0.029*
C13	0.29112 (5)	0.63975 (9)	0.95964 (16)	0.0288 (3)
H13A	0.3124	0.6341	1.0617	0.035*
H13B	0.2624	0.6641	1.0065	0.035*
C14	0.28248 (5)	0.54955 (9)	0.87859 (18)	0.0294 (3)
H14A	0.2589	0.5542	0.7844	0.035*
H14B	0.2712	0.5092	0.9732	0.035*
C15	0.32559 (4)	0.51217 (8)	0.79683 (16)	0.0256 (2)
H15A	0.3479	0.5014	0.8935	0.031*
H15B	0.3188	0.4551	0.7385	0.031*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.01858 (12)	0.04279 (19)	0.02381 (13)	0.00557 (12)	−0.00243 (10)	−0.01162 (12)
O1	0.0177 (3)	0.0308 (4)	0.0158 (3)	0.0055 (3)	−0.0021 (3)	−0.0051 (3)
N1	0.0182 (4)	0.0209 (4)	0.0145 (3)	0.0035 (3)	0.0016 (3)	−0.0039 (3)
N2	0.0175 (4)	0.0287 (5)	0.0129 (3)	0.0079 (3)	−0.0003 (3)	−0.0034 (3)
N3	0.0160 (4)	0.0367 (5)	0.0172 (4)	0.0089 (4)	−0.0009 (3)	−0.0080 (3)
C1	0.0191 (4)	0.0149 (4)	0.0126 (3)	0.0043 (3)	0.0003 (3)	−0.0005 (3)
O2	0.0183 (3)	0.0273 (4)	0.0230 (4)	0.0018 (3)	−0.0018 (3)	−0.0079 (3)
C2	0.0213 (4)	0.0153 (4)	0.0165 (4)	0.0035 (3)	−0.0003 (4)	−0.0019 (3)
C3	0.0293 (5)	0.0190 (4)	0.0174 (4)	0.0018 (4)	0.0001 (4)	−0.0053 (3)
C4	0.0339 (6)	0.0204 (5)	0.0165 (4)	0.0032 (4)	0.0066 (4)	−0.0036 (3)
C5	0.0237 (5)	0.0208 (5)	0.0194 (4)	0.0036 (4)	0.0066 (4)	0.0004 (4)
C6	0.0200 (4)	0.0171 (4)	0.0161 (4)	0.0036 (3)	0.0015 (3)	0.0005 (3)
C7	0.0238 (5)	0.0315 (6)	0.0363 (6)	0.0025 (5)	−0.0071 (5)	−0.0124 (5)
C8	0.0181 (4)	0.0175 (4)	0.0129 (3)	0.0054 (3)	0.0004 (3)	0.0000 (3)
C9	0.0177 (4)	0.0256 (5)	0.0152 (4)	0.0062 (4)	0.0010 (3)	−0.0006 (3)
C10	0.0171 (4)	0.0297 (5)	0.0154 (4)	0.0082 (4)	0.0012 (3)	−0.0031 (4)
C11	0.0184 (4)	0.0284 (5)	0.0214 (4)	0.0065 (4)	−0.0016 (4)	−0.0027 (4)
C12	0.0215 (5)	0.0292 (5)	0.0213 (4)	0.0098 (4)	−0.0024 (4)	−0.0048 (4)
C13	0.0298 (6)	0.0357 (6)	0.0208 (5)	0.0131 (5)	0.0065 (4)	−0.0040 (4)
C14	0.0274 (5)	0.0351 (6)	0.0258 (5)	0.0049 (5)	0.0102 (5)	−0.0011 (5)
C15	0.0275 (5)	0.0280 (5)	0.0214 (5)	0.0080 (5)	0.0049 (4)	−0.0013 (4)

Geometric parameters (Å, º) top

S1—C9	1.6737 (11)	C6—H6A	0.9500
O1—C8	1.2426 (13)	C7—H7A	0.9800
N1—C8	1.3321 (13)	C7—H7B	0.9800
N1—N2	1.3795 (12)	C7—H7C	0.9800
N1—H1A	0.8800	C10—C11	1.5207 (17)
N2—C9	1.3611 (13)	C10—C15	1.5221 (17)
N2—H2A	0.8800	C10—H10A	1.0000
N3—C9	1.3349 (14)	C11—C12	1.5259 (15)
N3—C10	1.4593 (14)	C11—H11A	0.9900
N3—H3B	0.8800	C11—H11B	0.9900
C1—C6	1.3912 (15)	C12—C13	1.5190 (18)
C1—C2	1.4059 (14)	C12—H12A	0.9900
C1—C8	1.4864 (13)	C12—H12B	0.9900
O2—C2	1.3629 (13)	C13—C14	1.5189 (19)
O2—C7	1.4299 (14)	C13—H13A	0.9900
C2—C3	1.3918 (14)	C13—H13B	0.9900
C3—C4	1.3845 (17)	C14—C15	1.5225 (17)
C3—H3A	0.9500	C14—H14A	0.9900
C4—C5	1.3830 (17)	C14—H14B	0.9900
C4—H4A	0.9500	C15—H15A	0.9900
C5—C6	1.3848 (14)	C15—H15B	0.9900
C5—H5A	0.9500

C8—N1—N2	118.99 (9)	N3—C9—S1	125.44 (8)
C8—N1—H1A	120.5	N2—C9—S1	121.41 (8)
N2—N1—H1A	120.5	N3—C10—C11	108.87 (9)
C9—N2—N1	118.36 (9)	N3—C10—C15	110.91 (9)
C9—N2—H2A	120.8	C11—C10—C15	111.57 (9)
N1—N2—H2A	120.8	N3—C10—H10A	108.5
C9—N3—C10	124.83 (10)	C11—C10—H10A	108.5
C9—N3—H3B	117.6	C15—C10—H10A	108.5
C10—N3—H3B	117.6	C10—C11—C12	110.84 (10)
C6—C1—C2	118.08 (9)	C10—C11—H11A	109.5
C6—C1—C8	116.30 (9)	C12—C11—H11A	109.5
C2—C1—C8	125.62 (9)	C10—C11—H11B	109.5
C2—O2—C7	118.99 (9)	C12—C11—H11B	109.5
O2—C2—C3	122.44 (10)	H11A—C11—H11B	108.1
O2—C2—C1	117.30 (9)	C13—C12—C11	111.31 (10)
C3—C2—C1	120.26 (10)	C13—C12—H12A	109.4
C4—C3—C2	119.98 (10)	C11—C12—H12A	109.4
C4—C3—H3A	120.0	C13—C12—H12B	109.4
C2—C3—H3A	120.0	C11—C12—H12B	109.4
C5—C4—C3	120.68 (10)	H12A—C12—H12B	108.0
C5—C4—H4A	119.7	C14—C13—C12	111.14 (10)
C3—C4—H4A	119.7	C14—C13—H13A	109.4
C4—C5—C6	119.07 (11)	C12—C13—H13A	109.4
C4—C5—H5A	120.5	C14—C13—H13B	109.4
C6—C5—H5A	120.5	C12—C13—H13B	109.4
C5—C6—C1	121.91 (10)	H13A—C13—H13B	108.0
C5—C6—H6A	119.0	C13—C14—C15	110.73 (11)
C1—C6—H6A	119.0	C13—C14—H14A	109.5
O2—C7—H7A	109.5	C15—C14—H14A	109.5
O2—C7—H7B	109.5	C13—C14—H14B	109.5
H7A—C7—H7B	109.5	C15—C14—H14B	109.5
O2—C7—H7C	109.5	H14A—C14—H14B	108.1
H7A—C7—H7C	109.5	C10—C15—C14	111.37 (10)
H7B—C7—H7C	109.5	C10—C15—H15A	109.4
O1—C8—N1	120.62 (9)	C14—C15—H15A	109.4
O1—C8—C1	121.60 (9)	C10—C15—H15B	109.4
N1—C8—C1	117.78 (9)	C14—C15—H15B	109.4
N3—C9—N2	113.15 (9)	H15A—C15—H15B	108.0

C8—N1—N2—C9	155.21 (10)	C2—C1—C8—O1	175.77 (10)
C7—O2—C2—C3	0.13 (16)	C6—C1—C8—N1	176.75 (9)
C7—O2—C2—C1	−179.76 (10)	C2—C1—C8—N1	−3.91 (15)
C6—C1—C2—O2	−178.77 (9)	C10—N3—C9—N2	−173.24 (11)
C8—C1—C2—O2	1.90 (15)	C10—N3—C9—S1	6.15 (17)
C6—C1—C2—C3	1.33 (15)	N1—N2—C9—N3	−165.32 (10)
C8—C1—C2—C3	−178.00 (10)	N1—N2—C9—S1	15.26 (14)
O2—C2—C3—C4	179.74 (10)	C9—N3—C10—C11	−147.21 (11)
C1—C2—C3—C4	−0.37 (16)	C9—N3—C10—C15	89.66 (13)
C2—C3—C4—C5	−0.45 (17)	N3—C10—C11—C12	−177.45 (9)
C3—C4—C5—C6	0.27 (17)	C15—C10—C11—C12	−54.71 (12)
C4—C5—C6—C1	0.76 (16)	C10—C11—C12—C13	55.32 (13)
C2—C1—C6—C5	−1.54 (15)	C11—C12—C13—C14	−56.40 (14)
C8—C1—C6—C5	177.85 (9)	C12—C13—C14—C15	56.28 (14)
N2—N1—C8—O1	4.70 (15)	N3—C10—C15—C14	176.78 (10)
N2—N1—C8—C1	−175.62 (9)	C11—C10—C15—C14	55.22 (13)
C6—C1—C8—O1	−3.58 (14)	C13—C14—C15—C10	−55.65 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O2	0.88	1.90	2.5907 (12)	135
N2—H2A···O1ⁱ	0.88	2.11	2.8523 (12)	142
N3—H3B···O1ⁱ	0.88	2.04	2.8607 (12)	155

Symmetry code: (i) −x+1, −y+1, −z+1.

Funding information

AB is grateful to the UGC, New Delhi, India for the award of a Project UGC-Start-up Grant 2015–16 (No. F.30–109/2015, BSR).

References

Bharti, A., Bharati, P., Singh, N. K. & Bharty, M. K. (2016). J. Coord. Chem. 69, 1258–1271. Web of Science CSD CrossRef CAS Google Scholar
Castiñeiras, A., Fernández-Hermida, N., García-Santos, I. & Gómez-Rodríguez, L. (2012). Dalton Trans. 41, 13486–13495. Google Scholar
Dulare, R., Bharty, M. K., Kushawaha, S. K., Singh, S. & Singh, N. K. (2011). Polyhedron, 30, 1960–1967. Web of Science CSD CrossRef CAS Google Scholar
Hovsepian, T. R., Dilanian, E. R., Engoyan, A. P. & Melik-Ohanjanian, R. G. (2004). Chem. Heterocycl. Compd. 40, 1194–1198. CrossRef CAS Google Scholar
Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466–470. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Nath, P., Bharty, M. K., Chaurasia, R., Kumari, S. & Gupta, S. K. (2015). Acta Cryst. E71, o967–o968. Web of Science CSD CrossRef IUCr Journals Google Scholar
Paswan, S., Bharty, M. K., Kumari, S., Gupta, S. K. & Singh, N. K. (2015). Acta Cryst. E71, o880–o881. Web of Science CSD CrossRef IUCr Journals Google Scholar
Plech, T., Wujec, M., Siwek, A., Kosikowska, U. & Malm, A. (2011). Eur. J. Med. Chem. 46, 241–248. Web of Science CrossRef CAS PubMed Google Scholar
Rigaku OD (2015). CrysAlis PRO. Rigaku Oxford Diffraction, Yarnton, England. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals 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
Siddiqui, N. & Singh, O. (2003). Indian J. Pharm. Sci. 65, 423–425. CAS Google Scholar
Singh, A., Bharty, M. K., Dani, R. K., Singh, S., Kushawaha, S. K. & Singh, N. K. (2014). Polyhedron, 73, 98–109. Web of Science CSD CrossRef Google Scholar
Siwek, A., Stączek, P. & Stefańska, J. (2011). Eur. J. Med. Chem. 46, 5717–5726. Web of Science CrossRef CAS Google Scholar
Spek, A. L. (2015). Acta Cryst. C71, 9–18. Web of Science CrossRef IUCr Journals Google Scholar

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