Allyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxyl­ate

Krishnan, G.A.; Kumar, C.U.; Mohandas, T.; Pillai, M.V.; Sakthivel, P.

doi:10.1107/S2414314619000543

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 4| Part 1| January 2019| x190054

https://doi.org/10.1107/S2414314619000543

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Allyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate

G. Anantha Krishnan,^a C. Udhaya Kumar,^b ^* T. Mohandas,^c M. Velayutham Pillai ^b and P. Sakthivel ^d ^*

^aDepartment of Physics, Saranathan College of Engineering, Panjappur, Tiruchirappalli, Tamilnadu, India, ^bDepartment of Chemistry, School of Advanced Sciences, Kalasalingam Academy of Research and Education (Deemed to be University), Krishnankoil 626 126, Tamil Nadu, India, ^cDepartment of Physics, K. Ramakrishnan College of Engineering, Samayapuram, Tiruchirappalli, Tamil Nadu, India, and ^dDepartment of Physics, Urumu Dhanalakshmi College, Tiruchirappalli, Tamil Nadu, India
^*Correspondence e-mail: udkchemist@gmail.com, sakthi2udc@gmail.com

Edited by R. J. Butcher, Howard University, USA (Received 13 September 2018; accepted 10 January 2019; online 15 January 2019)

In the title compound, C₁₇H₁₆N₂O₃, the 4H-pyran ring adopts a boat conformation. In the crystal, N—H⋯N and N—H⋯O interactions link the molecules, forming an infinite ribbon running along the a-axis direction with N—H⋯N interactions forming centrosymmetric R²₂(12) graph-set motifs. The allyl side chain is disordered over two sets of sites with occupancies of 0.720 (7) and 0.280 (7).

Keywords: crystal structure; 4H-pyran derivatives.

CCDC reference: 1889948

Structure description

Pyran derivatives constitute a useful class of heterocyclic compounds, which are widely distributed in nature (Moriguchi et al., 1997 ). A number of 2-amino-4H-pyrans are used as photoactive materials (Armesto et al., 1989 ), pigments (Rideout et al., 1976 ) and potentially biodegradable agrochemicals (Kumar et al., 2009 ). Substituted allyl 6-amino-4H-pyran derivatives exhibit a wide range of biological properties including antiproliferative and antitubercular activities (Panda et al., 1997 ; Mungra et al., 2011 ) and 4H-pyran derivatives are widely used as organic intermediates (Liang et al., 2009 ).

The 4H-pyran ring in the title compound (Fig. 1) exhibits a boat conformation with puckering parameters Q = 0.230 (3) Å, θ = 79.8 (7)° and φ = 191.1 (7)°. In this ring, the atoms O1 and C7 make the largest deviations of 0.118 (2) and 0.139 (2) Å, respectively, from the mean plane. The C7—C8—C9—C13 and C7—C11—C10—N1 torsion angles are 179.3 (2) and 171.0 (2)°, respectively. The dihedral angle between 4H-pyran ring and the phenyl ring is 85.51 (15)°. The bond lengths in the 4H-pyran ring are similar to those in a related compound (Mohandas et al., 2015 ). An intramolecular C—H⋯O hydrogen bond occurs.

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 20% probability level (only the major disorder component of the allyl side chain is shown).

In the crystal, N—H⋯N and N—H⋯O interactions (Table 1) link the molecules, forming an infinite ribbon running along [100] (Fig. 2). The N—H⋯N interactions form an R₂²(12) graph-set motif.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N1⋯N2ⁱ	0.83 (2)	2.24 (2)	3.051 (2)	166.0 (19)
N1—H1N2⋯O2ⁱⁱ	0.88 (2)	2.04 (2)	2.919 (2)	171 (2)
C13—H13A⋯O3	0.96	2.27	2.868 (3)	120
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x-1, y, z.

Figure 2
The packing of the title compound (major disorder component only). N—H⋯N and N—H⋯O interactions (Table 1

) are shown as dashed lines.

Synthesis and crystallization

A mixture of benzaldehyde (1.0 mmol), malononitrile (1.0 mmol), allyl 3-oxobutanoate (1.0 mmol) and a few drops of piperidine was stirred magnetically in 30 ml of absolute ethanol at 80°C for 90 min. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was allowed to cool to room temperature and the solvent was evaporated. The resulting solid was collected and washed with cold water and recrystallized from ethanol to obtain the pure product (yield 86%).

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The allyl side chain is disordered and was refined as having two equivalent conformations with occupancies of 0.720 (7) and 0.280 (7).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₆N₂O₃
M_r	296.32
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	293
a, b, c (Å)	8.2151 (5), 9.2850 (5), 11.6086 (7)
α, β, γ (°)	108.184 (4), 103.004 (4), 105.089 (2)
V (Å³)	765.64 (8)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.09
Crystal size (mm)	0.20 × 0.20 × 0.15

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2008 )
T_min, T_max	0.956, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	3789, 3789, 2207
R_int	0.053
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.160, 1.02
No. of reflections	3789
No. of parameters	237
No. of restraints	79
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.21, −0.28
Computer programs: APEX2, SAINT and XPREP (Bruker, 2008), SHELXS and SHELXL97 (Sheldrick, 2008 ), SHELXL2018/3 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Structural data

CCDC reference: 1889948

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314619000543/bv4022sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314619000543/bv4022Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314619000543/bv4022Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: APEX2 and SAINT (Bruker, 2008); data reduction: SAINT and XPREP (Bruker, 2008); program(s) used to solve structure: SHELXS (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018/3 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Allyl 6-amino-5-cyano-2-methyl-4-phenyl-4H-pyran-3-carboxylate top

Crystal data top

C₁₇H₁₆N₂O₃	Z = 2
M_r = 296.32	F(000) = 312
Triclinic, P1	D_x = 1.285 Mg m⁻³
a = 8.2151 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 9.2850 (5) Å	Cell parameters from 4207 reflections
c = 11.6086 (7) Å	θ = 2.5–23.4°
α = 108.184 (4)°	µ = 0.09 mm⁻¹
β = 103.004 (4)°	T = 293 K
γ = 105.089 (2)°	BLOCK, orange
V = 765.64 (8) Å³	0.20 × 0.20 × 0.15 mm

Data collection top

Bruker Kappa APEXII CCD diffractometer	2207 reflections with I > 2σ(I)
ω and φ scan	R_int = 0.053
Absorption correction: multi-scan (SADABS; Bruker, 2008)	θ_max = 28.3°, θ_min = 2.5°
T_min = 0.956, T_max = 0.960	h = −10→10
3789 measured reflections	k = −12→12
3789 independent reflections	l = −15→15

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.052	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.160	w = 1/[σ²(F_o²) + (0.071P)² + 0.1156P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max < 0.001
3789 reflections	Δρ_max = 0.21 e Å⁻³
237 parameters	Δρ_min = −0.28 e Å⁻³
79 restraints	Extinction correction: SHELXL-2018/3 (Sheldrick 2018), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.028 (6)

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 positions of the hydrogen atoms bound to the O and C atoms are identified from the difference electron density maps and their distances are geometrically optimized. The hydrogen atoms bound to the C atoms are treated as riding atoms, with d(C—H) = 0.93 Å and U_iso(H) = 1.2U_eq(C) for aromatic, d(C—H) = 0.97 Å and U_iso(H) = 1.2U_eq(C) for methylene and d(C—H) = 0.96 Å and U_iso(H) = 1.5U_eq(C) for methyl groups. The amine protons were refined isotropically.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
O1	0.13227 (16)	0.88787 (15)	0.32279 (13)	0.0513 (4)
O2	0.72395 (18)	0.92452 (18)	0.36162 (17)	0.0742 (5)
O3	0.62148 (18)	1.06948 (19)	0.26548 (15)	0.0728 (5)
N1	−0.0492 (2)	0.7331 (2)	0.38698 (18)	0.0580 (5)
H1N1	−0.080 (3)	0.663 (3)	0.4157 (19)	0.057 (6)*
H1N2	−0.109 (3)	0.797 (3)	0.376 (2)	0.068 (6)*
N2	0.1936 (2)	0.4855 (2)	0.48236 (19)	0.0700 (6)
C1	0.3644 (2)	0.5954 (2)	0.21556 (18)	0.0474 (4)
C2	0.4475 (3)	0.4852 (3)	0.2186 (2)	0.0693 (6)
H2A	0.523004	0.495812	0.296026	0.083*
C3	0.4174 (4)	0.3571 (3)	0.1044 (3)	0.0938 (9)
H3A	0.472222	0.281595	0.106231	0.113*
C4	0.3083 (5)	0.3415 (3)	−0.0102 (3)	0.0942 (9)
H4A	0.290072	0.256420	−0.085936	0.113*
C5	0.2271 (4)	0.4499 (3)	−0.0129 (2)	0.0881 (8)
H5A	0.152576	0.439516	−0.090676	0.106*
C6	0.2543 (3)	0.5753 (3)	0.0988 (2)	0.0700 (6)
H6A	0.196780	0.648748	0.095559	0.084*
C7	0.3897 (2)	0.7335 (2)	0.33875 (16)	0.0424 (4)
H7A	0.494936	0.744799	0.405599	0.051*
C8	0.4222 (2)	0.8932 (2)	0.32389 (16)	0.0421 (4)
C9	0.2989 (2)	0.9618 (2)	0.31696 (17)	0.0454 (4)
C10	0.1074 (2)	0.7670 (2)	0.36705 (16)	0.0437 (4)
C11	0.2308 (2)	0.6973 (2)	0.38400 (16)	0.0426 (4)
C12	0.2067 (2)	0.5791 (2)	0.43693 (18)	0.0488 (4)
C13	0.3033 (3)	1.1169 (3)	0.3039 (2)	0.0652 (6)
H13A	0.425021	1.184266	0.324493	0.098*
H13B	0.251375	1.171848	0.361704	0.098*
H13C	0.236508	1.094610	0.217107	0.098*
C14	0.6031 (2)	0.9636 (2)	0.31985 (18)	0.0484 (4)
C15A	0.814 (5)	1.136 (3)	0.2707 (18)	0.084 (3)	0.280 (7)
H15A	0.885611	1.222435	0.354245	0.101*	0.280 (7)
H15B	0.864085	1.051113	0.257234	0.101*	0.280 (7)
C16A	0.8150 (18)	1.1965 (15)	0.1739 (11)	0.098 (3)	0.280 (7)
H16A	0.885497	1.304306	0.198254	0.117*	0.280 (7)
C17A	0.728 (2)	1.1155 (18)	0.0576 (11)	0.149 (5)	0.280 (7)
H17A	0.656193	1.007380	0.029871	0.179*	0.280 (7)
H17B	0.734994	1.163255	−0.001548	0.179*	0.280 (7)
C15B	0.7942 (19)	1.1526 (13)	0.2641 (6)	0.093 (2)	0.720 (7)
H15C	0.824470	1.268629	0.307193	0.111*	0.720 (7)
H15D	0.882796	1.122081	0.311836	0.111*	0.720 (7)
C16B	0.8014 (7)	1.1178 (6)	0.1398 (4)	0.1014 (17)	0.720 (7)
H16B	0.721066	1.016544	0.079943	0.122*	0.720 (7)
C17B	0.8942 (6)	1.1959 (7)	0.0949 (5)	0.1199 (19)	0.720 (7)
H17C	0.978344	1.298620	0.147859	0.144*	0.720 (7)
H17D	0.880257	1.152447	0.007964	0.144*	0.720 (7)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0444 (7)	0.0617 (8)	0.0695 (9)	0.0266 (6)	0.0260 (6)	0.0421 (7)
O2	0.0458 (8)	0.0656 (9)	0.1176 (13)	0.0250 (7)	0.0311 (8)	0.0375 (9)
O3	0.0517 (8)	0.0913 (11)	0.0830 (10)	0.0102 (7)	0.0273 (7)	0.0531 (9)
N1	0.0509 (10)	0.0682 (12)	0.0831 (13)	0.0301 (9)	0.0369 (9)	0.0483 (10)
N2	0.0740 (12)	0.0741 (12)	0.0988 (15)	0.0377 (10)	0.0476 (11)	0.0585 (12)
C1	0.0468 (10)	0.0454 (10)	0.0596 (11)	0.0179 (8)	0.0293 (9)	0.0237 (9)
C2	0.0816 (15)	0.0599 (13)	0.0913 (16)	0.0384 (12)	0.0465 (13)	0.0384 (12)
C3	0.127 (2)	0.0589 (15)	0.127 (3)	0.0528 (16)	0.078 (2)	0.0362 (16)
C4	0.123 (2)	0.0610 (16)	0.090 (2)	0.0183 (16)	0.0658 (19)	0.0093 (14)
C5	0.0939 (19)	0.0846 (18)	0.0627 (15)	0.0207 (15)	0.0283 (13)	0.0073 (13)
C6	0.0752 (14)	0.0731 (15)	0.0587 (13)	0.0329 (12)	0.0226 (11)	0.0165 (11)
C7	0.0400 (9)	0.0474 (10)	0.0465 (10)	0.0199 (7)	0.0155 (7)	0.0228 (8)
C8	0.0421 (9)	0.0431 (9)	0.0429 (9)	0.0140 (7)	0.0165 (7)	0.0185 (8)
C9	0.0454 (10)	0.0489 (10)	0.0490 (10)	0.0179 (8)	0.0190 (8)	0.0252 (8)
C10	0.0441 (10)	0.0476 (10)	0.0464 (10)	0.0174 (8)	0.0192 (8)	0.0236 (8)
C11	0.0473 (10)	0.0440 (9)	0.0460 (10)	0.0201 (8)	0.0208 (8)	0.0229 (8)
C12	0.0496 (10)	0.0516 (11)	0.0595 (11)	0.0246 (8)	0.0273 (9)	0.0285 (9)
C13	0.0675 (13)	0.0634 (13)	0.0876 (16)	0.0319 (11)	0.0333 (12)	0.0467 (12)
C14	0.0458 (10)	0.0440 (10)	0.0512 (10)	0.0131 (8)	0.0194 (8)	0.0135 (8)
C15A	0.057 (5)	0.109 (5)	0.094 (5)	0.010 (4)	0.030 (4)	0.061 (4)
C16A	0.076 (4)	0.110 (5)	0.105 (5)	0.001 (5)	0.027 (4)	0.069 (4)
C17A	0.191 (10)	0.144 (8)	0.111 (6)	0.050 (8)	0.035 (8)	0.067 (7)
C15B	0.060 (4)	0.118 (3)	0.084 (2)	−0.006 (3)	0.029 (2)	0.047 (2)
C16B	0.093 (3)	0.098 (3)	0.096 (3)	0.007 (3)	0.049 (2)	0.027 (3)
C17B	0.095 (3)	0.175 (5)	0.099 (3)	0.018 (3)	0.042 (2)	0.085 (3)

Geometric parameters (Å, º) top

O1—C10	1.361 (2)	C7—H7A	0.9800
O1—C9	1.389 (2)	C8—C9	1.331 (2)
O2—C14	1.197 (2)	C8—C14	1.477 (2)
O3—C14	1.319 (2)	C9—C13	1.486 (2)
O3—C15B	1.434 (13)	C10—C11	1.348 (2)
O3—C15A	1.52 (4)	C11—C12	1.409 (2)
N1—C10	1.333 (2)	C13—H13A	0.9600
N1—H1N1	0.83 (2)	C13—H13B	0.9600
N1—H1N2	0.88 (2)	C13—H13C	0.9600
N2—C12	1.143 (2)	C15A—C16A	1.404 (4)
C1—C2	1.375 (3)	C15A—H15A	0.9700
C1—C6	1.376 (3)	C15A—H15B	0.9700
C1—C7	1.521 (2)	C16A—C17A	1.245 (4)
C2—C3	1.396 (4)	C16A—H16A	0.9300
C2—H2A	0.9300	C17A—H17A	0.9300
C3—C4	1.367 (4)	C17A—H17B	0.9300
C3—H3A	0.9300	C15B—C16B	1.395 (4)
C4—C5	1.349 (4)	C15B—H15C	0.9700
C4—H4A	0.9300	C15B—H15D	0.9700
C5—C6	1.371 (3)	C16B—C17B	1.227 (3)
C5—H5A	0.9300	C16B—H16B	0.9300
C6—H6A	0.9300	C17B—H17C	0.9300
C7—C8	1.508 (2)	C17B—H17D	0.9300
C7—C11	1.511 (2)

C10—O1—C9	119.93 (13)	C11—C10—O1	121.05 (15)
C14—O3—C15B	120.1 (4)	C10—C11—C12	119.89 (15)
C14—O3—C15A	110.7 (7)	C10—C11—C7	121.69 (15)
C10—N1—H1N1	120.4 (14)	C12—C11—C7	118.27 (14)
C10—N1—H1N2	116.0 (14)	N2—C12—C11	177.5 (2)
H1N1—N1—H1N2	123 (2)	C9—C13—H13A	109.5
C2—C1—C6	118.3 (2)	C9—C13—H13B	109.5
C2—C1—C7	120.80 (19)	H13A—C13—H13B	109.5
C6—C1—C7	120.86 (16)	C9—C13—H13C	109.5
C1—C2—C3	119.4 (2)	H13A—C13—H13C	109.5
C1—C2—H2A	120.3	H13B—C13—H13C	109.5
C3—C2—H2A	120.3	O2—C14—O3	122.49 (17)
C4—C3—C2	120.8 (2)	O2—C14—C8	121.74 (17)
C4—C3—H3A	119.6	O3—C14—C8	115.75 (16)
C2—C3—H3A	119.6	C16A—C15A—O3	108 (2)
C5—C4—C3	119.7 (2)	C16A—C15A—H15A	110.1
C5—C4—H4A	120.1	O3—C15A—H15A	110.1
C3—C4—H4A	120.1	C16A—C15A—H15B	110.1
C4—C5—C6	120.1 (3)	O3—C15A—H15B	110.1
C4—C5—H5A	120.0	H15A—C15A—H15B	108.4
C6—C5—H5A	120.0	C17A—C16A—C15A	124.5 (11)
C5—C6—C1	121.7 (2)	C17A—C16A—H16A	117.7
C5—C6—H6A	119.1	C15A—C16A—H16A	117.7
C1—C6—H6A	119.1	C16A—C17A—H17A	120.0
C8—C7—C11	109.31 (13)	C16A—C17A—H17B	120.0
C8—C7—C1	112.26 (14)	H17A—C17A—H17B	120.0
C11—C7—C1	111.41 (14)	C16B—C15B—O3	112.7 (8)
C8—C7—H7A	107.9	C16B—C15B—H15C	109.1
C11—C7—H7A	107.9	O3—C15B—H15C	109.1
C1—C7—H7A	107.9	C16B—C15B—H15D	109.1
C9—C8—C14	124.63 (16)	O3—C15B—H15D	109.1
C9—C8—C7	122.28 (15)	H15C—C15B—H15D	107.8
C14—C8—C7	113.08 (15)	C17B—C16B—C15B	131.9 (8)
C8—C9—O1	120.91 (15)	C17B—C16B—H16B	114.0
C8—C9—C13	131.04 (17)	C15B—C16B—H16B	114.0
O1—C9—C13	108.05 (15)	C16B—C17B—H17C	120.0
N1—C10—C11	128.55 (17)	C16B—C17B—H17D	120.0
N1—C10—O1	110.40 (15)	H17C—C17B—H17D	120.0

C6—C1—C2—C3	−0.2 (3)	C9—O1—C10—N1	168.74 (16)
C7—C1—C2—C3	178.11 (18)	C9—O1—C10—C11	−11.9 (2)
C1—C2—C3—C4	0.8 (4)	N1—C10—C11—C12	−4.5 (3)
C2—C3—C4—C5	−0.7 (4)	O1—C10—C11—C12	176.32 (16)
C3—C4—C5—C6	0.1 (4)	N1—C10—C11—C7	171.01 (18)
C4—C5—C6—C1	0.4 (4)	O1—C10—C11—C7	−8.2 (3)
C2—C1—C6—C5	−0.4 (3)	C8—C7—C11—C10	21.4 (2)
C7—C1—C6—C5	−178.71 (19)	C1—C7—C11—C10	−103.26 (19)
C2—C1—C7—C8	135.66 (18)	C8—C7—C11—C12	−163.08 (15)
C6—C1—C7—C8	−46.0 (2)	C1—C7—C11—C12	72.3 (2)
C2—C1—C7—C11	−101.37 (19)	C15B—O3—C14—O2	−5.2 (5)
C6—C1—C7—C11	76.9 (2)	C15A—O3—C14—O2	−2.7 (9)
C11—C7—C8—C9	−17.1 (2)	C15B—O3—C14—C8	176.0 (4)
C1—C7—C8—C9	106.99 (19)	C15A—O3—C14—C8	178.4 (9)
C11—C7—C8—C14	162.07 (14)	C9—C8—C14—O2	158.52 (19)
C1—C7—C8—C14	−73.79 (18)	C7—C8—C14—O2	−20.7 (2)
C14—C8—C9—O1	−179.35 (15)	C9—C8—C14—O3	−22.6 (3)
C7—C8—C9—O1	−0.2 (3)	C7—C8—C14—O3	158.17 (15)
C14—C8—C9—C13	0.1 (3)	C14—O3—C15A—C16A	158.0 (12)
C7—C8—C9—C13	179.25 (19)	O3—C15A—C16A—C17A	−56 (3)
C10—O1—C9—C8	16.3 (2)	C14—O3—C15B—C16B	117.5 (6)
C10—O1—C9—C13	−163.28 (16)	O3—C15B—C16B—C17B	152.6 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N1···N2ⁱ	0.83 (2)	2.24 (2)	3.051 (2)	166.0 (19)
N1—H1N2···O2ⁱⁱ	0.88 (2)	2.04 (2)	2.919 (2)	171 (2)
C13—H13A···O3	0.96	2.27	2.868 (3)	120

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

Acknowledgements

The authors thank Dr D. Srinivasan, Principal of K. Ramakrishnan College of Engineering, Trichy, for making the work successful.

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