Crystal structure of 4-[(3-meth­oxy-2-oxidobenzyl­idene)azaniumyl]­benzoic acid methanol monosolvate

Kamaal, S.; Faizi, M.S.H.; Ali, A.; Ahmad, M.; Iskenderov, T.

doi:10.1107/S2056989018016262

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Volume 74| Part 12| December 2018| Pages 1847-1850

https://doi.org/10.1107/S2056989018016262

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Crystal structure of 4-[(3-methoxy-2-oxidobenzylidene)azaniumyl]benzoic acid methanol monosolvate

Saima Kamaal,^a Md. Serajul Haque Faizi,^b ^* Akram Ali,^c Musheer Ahmad ^a and Turganbay Iskenderov ^d ^*

^aDepartment of Applied Chemistry, Faculty of Engineering & Technology, Aligarh, Muslim University, Aligarh UP 202002, India, ^bDepartment of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, Bihar 842 001, India, ^cCMP College Allahabad, a constitution college of Allahabad University, Allahabad, UP, India, and ^dNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str., 64, 01601 Kyiv, Ukraine
^*Correspondence e-mail: faizichemiitg@gmail.com, tiskenderov@ukr.net

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 29 October 2018; accepted 16 November 2018; online 22 November 2018)

In the crystal of the title compound, C₁₅H₁₃NO₄·CH₃OH, the Schiff base molecule exists in the zwitterionic form; an intramolecular N—H⋯O hydrogen bond stabilizes the molecular structure. The benzene rings are nearly co-planar, subtending a dihedral angle of 5.34 (2)°. In the crystal, classical O—H⋯O and weak C—H⋯O hydrogen bonds link the Schiff base molecules and methanol solvent molecules into a three-dimensional supramolecular architecture. The crystal studied was refined as an inversion twin.

Keywords: crystal structure; zwitterion; 2-hydroxy-3-methoxy-benzaldehyde; 4-aminobenzoic acid (PABA); Schiff base; hydrogen bonding; vanillin.

CCDC reference: 1879300

1. Chemical context

Vanillin and o-vanillin are natural compounds that have both a phenolic OH and an aldehyde group. They are positional isomers, in which o-vanillin shows contradictory effects. There are several reports indicating that o-vanillin induces mutations and it has also been found to enhance chromosomal aberrations in in vitro systems (Barik et al., 2004 ; Takahashi et al., 1989 ). Vanillin is also the primary component of the extract of the vanilla bean. Synthetic vanillin rather than natural vanilla extract is now more often used as a flavouring agent in foods, beverages and pharmaceuticals. Schiff bases containing o-vanillin possess antifungal and antibacterial properties (Thorat et al., 2012 ). 4-Aminobenzoic acid (PABA) is an important biological molecule, being an essential bacterial cofactor involved in the synthesis of folic acid (Robinson, 1966 ). PABA shows polymorphism and so far four polymorphs of PABA are known, all of which are centrosymmetric; a non-centrosymmetric polymorph of 4-aminobenzoic acid has also been reported (Benali-Cherif et al., 2014 ). Schiff bases derived from 2-hydroxy-3-methoxybenzaldehyde (o-vanillin) and PABA have not been investigated so thoroughly. Our research interest focuses on the study of Schiff bases derived from salicylaldehyde. It is well known that Schiff bases of salicylaldehyde derivatives may exhibit thermochromism or photochromism, depending on the planarity or non-planarity of the molecule (Cohen & Schmidt, 1964 ; Amimoto & Kawato, 2005 ). Schiff bases often exhibit various biological activities and in many cases have been shown to possess antibacterial, anticancer, anti-inflammatory and antitoxic properties (Lozier et al., 1975 ). They are used as anion sensors (Dalapati et al., 2011 ), as non-linear optical compounds (Sun et al., 2012 ) and as versatile polynuclear ligands for multinuclear magnetic exchange clusters (Moroz et al., 2012 ). New salicylaldehyde-based Schiff bases have also been synthesized and reported (Faizi et al., 2015a ,b ; 2016b ; 2017a ,b ,c ). The present work is a part of an ongoing structural study of Schiff bases and their utilization in the synthesis of new organic, excited state proton-transfer compounds and fluorescent chemosensors (Faizi et al., 2016a ; Faizi et al., 2018 ; Kumar et al., 2018 ; Mukherjee et al., 2018 ). We report herein the crystal structure of the title compound synthesized by the condensation reaction of 2-hydroxy-3-methoxybenzaldehyde and PABA.

2. Structural commentary

The asymmetric unit of the title compound contains a Schiff base molecule and a methanol molecule of crystallization. In the solid state, the Schiff base molecule (Fig. 1) exists in the zwitterionic form. An intramolecular N—H⋯O hydrogen bond stabilizes the molecular structure (Table 1). The imine group, which displays a C9—C8—N1—C5 torsion angle of 177.6 (3)°, contributes to the general planarity of the molecule. The Schiff base molecule displays a trans configuration with respect to the C=N and C–N bonds. The vanillin ring (C9–C14) is inclined to the central benzene ring (C2–C7) by 5.34 (2)°. A similar value of 5.3 (2)° is observed in 4-chloro-N′-(2-hydroxy-4-methoxybenzylidene)benzohydrazide methanol monosolvate (Zhi et al., 2011 ). All bond lengths are in normal ranges. The O4—C15 bond length is 1.432 (2) Å and similar value of 1.432 (2) Å is observed in (E)-2-hydroxy-3-methoxy-5-[(3-methoxyphenyl)diazenyl]benzaldehyde (Karadayı et al., 2006 ). The methoxy group of the 2-hydroxy-3-methoxyphenyl is almost coplanar with its bound benzene ring, as seen by the C_methyl—O—C—C torsion angle of 178.1 (2)°.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O3	0.86	1.87	2.568 (4)	138
O2—H2⋯O5ⁱ	0.82	1.80	2.598 (4)	164
O5—H5O⋯O3ⁱⁱ	0.96 (5)	1.77 (5)	2.690 (4)	159 (4)
C7—H7⋯O2ⁱ	0.93	2.56	3.233 (5)	130
C8—H8⋯O1ⁱⁱⁱ	0.93	2.41	3.281 (5)	155
Symmetry codes: (i) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) x+1, y+1, z; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling and the intramolecular N—H⋯O hydrogen bond as a dashed line. Displacement ellipsoids are drawn at the 40% probability level.

3. Supramolecular features

In the crystal, the hydroxyl group of the methanol solvent molecule is linked to the carboxylate group of the neighboring Schiff base molecule and the deprotonated hydroxyl group of the other Schiff base molecule via classical O—H⋯O hydrogen bonds, forming supramolecular chains propagating along the b-axis direction (Fig. 2). Weak C—H⋯O hydrogen bonds further link the chains into a three-dimensional supramolecular architecture.

Figure 2
A view of the hydrogen-bonded chain extending along the b-axis direction. Hydrogen bonds are shown as dashed lines.

4. Database survey

A search of the Cambridge Structural Database (CSD version 5.39, February 2018 update; Groom et al., 2016 ) for similar systems (benzylidene-phenyl-amine) yielded 285 hits of which ten are similar substituted benzylidene-phenyl-amines: N-salicylidene-p-chloroaniline (I) (BADDAL01; Kamwaya & Khoo, 1985 ), 5-{[(1E)-(2-hydroxyphenyl)methylene]amino}-2-hydroxybenzoic acid (II) (CAWJOA; Bourque et al., 2005 ), 2-(2-hydroxy-5-methylbenzylideneammonio)benzoate (III) (CEXNEZ; Gayathri et al., 2007 ), N,N′-bis(2-hydroxy-1-naphthaldimine)-o-phenylenediamine methanol solvate (IV) (GETXEJ; Eltayeb et al., 2007 ), o-(salicylideneaminium)phenol chloride (V) (HALGUW; Ondrácek et al., 1993 ), N-(2-carboxyphenyl)salicylidenimine (VI) (JUTKAK; Ligtenbarg et al., 1999 ), diisothiocyantotriphenyltin bis[1-(salicyclideneimino)-2-methoxybenzene] (VII) (KIDYOL; Charland et al., 1989 ), N-(2-oxyphenyl)-3-methoxysalicylaldimine (VIII) (NEDMUF; Kannappan et al., 2006 ), N-(5-chloro-2-oxidobenzylidene)-2-hydroxy-5-methylanilinium (IX) (QIKHEX; Elmali et al., 2001 ) and N-(5-chloro-2-hydroxybenzylidene)-4-hydroxyaniline (X) (SAQTOT; Ogawa et al., 1998 ), 2-[(E)-(2-[{(E)-2,3-dihydroxybenzylidene]amino}-5-methylphenyl)iminiomethyl]-6-hydroxyphenolate (XI) (HUCQEC; Eltayeb et al., 2009 ) (see Fig. 3). The dihedral angle between the benzene rings in the title compound [5.34 (2)°] is smaller than those in compounds (III) [5.6 (1)°] (IV [5.84 (9)°], (V) [7.3 (1)°] and (IX) [9.51 (6)°] and (XI) [17.36 (12)°]. In compound (VII), cationic protonated pairs co-crystallize with five-coordinate organotin anions. In the title compound, they form an intramolecular S6 ring motif and stabilized by N—H⋯O hydrogen bonds.

Figure 3
Zwitterionic forms of some closely related compounds.

5. Synthesis and crystallization

To a hot stirred solution of 4-aminobenzoic acid (PABA) (1.00 g, 7.2 mmol) in methanol (15 ml) was added vanillin (1.11 g, 7.2 mmol)). The resulting mixture was then heated under reflux. After an hour, a precipitate formed. The reaction mixture was heated for about another 30 min until the completion of the reaction, which was monitored by TLC. The reaction mixture was cooled to room temperature, filtered and washed with hot methanol. It was then dried under vacuum to give the pure compound in 78% yield. Prismatic colourless single crystals of the title compound suitable for X-ray analysis were obtained by slow evaporation of a methanol solution.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N—H and O–H atoms were located in a difference-Fourier map. Their positional and isotropic thermal parameters were included in further stages of the refinement. All C-bound H atoms were positioned geometrically and refined using a riding model with C—H = 0.93–0.97 Å and with U_iso(H) = 1.2–1.5U_eq(C).

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₃NO₄·CH₄O
M_r	303.30
Crystal system, space group	Orthorhombic, P2₁2₁2₁
Temperature (K)	296
a, b, c (Å)	4.6993 (5), 10.038 (1), 30.155 (3)
V (Å³)	1422.5 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.61 × 0.36 × 0.17

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.963, 0.988
No. of measured, independent and observed [I > 2σ(I)] reflections	17046, 2526, 2117
R_int	0.095
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.112, 1.08
No. of reflections	2526
No. of parameters	206
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.26
Absolute structure	Refined as a perfect inversion twin.
Absolute structure parameter	0.5
Computer programs: X-AREA and X-RED (Stoe & Cie, 2002), SHELXT2014 (Sheldrick, 2015a ), SHELXL2017 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1879300

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989018016262/xu5950sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018016262/xu5950Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED (Stoe & Cie, 2002); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015b); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

4-[(3-Methoxy-2-oxidobenzylidene)azaniumyl]benzoic acid methanol monosolvate top

Crystal data top

C₁₅H₁₃NO₄·CH₄O	D_x = 1.416 Mg m⁻³
M_r = 303.30	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, P2₁2₁2₁	Cell parameters from 8708 reflections
a = 4.6993 (5) Å	θ = 2.4–29.9°
b = 10.038 (1) Å	µ = 0.11 mm⁻¹
c = 30.155 (3) Å	T = 296 K
V = 1422.5 (3) Å³	Prism, colorless
Z = 4	0.61 × 0.36 × 0.17 mm
F(000) = 640

Data collection top

STOE IPDS 2 diffractometer	2526 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	2117 reflections with I > 2σ(I)
Plane graphite monochromator	R_int = 0.095
Detector resolution: 6.67 pixels mm^-1	θ_max = 25.1°, θ_min = 2.7°
rotation method scans	h = −5→5
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	k = −11→11
T_min = 0.963, T_max = 0.988	l = −35→35
17046 measured reflections

Refinement top

Refinement on F²	Hydrogen site location: mixed
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F² > 2σ(F²)] = 0.046	w = 1/[σ²(F_o²) + (0.0401P)² + 0.7153P] where P = (F_o² + 2F_c²)/3
wR(F²) = 0.112	(Δ/σ)_max < 0.001
S = 1.08	Δρ_max = 0.25 e Å⁻³
2526 reflections	Δρ_min = −0.26 e Å⁻³
206 parameters	Absolute structure: Refined as a perfect inversion twin.
0 restraints	Absolute structure parameter: 0.5

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 two-component inversion twin

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

	x	y	z	U_iso*/U_eq
C1	0.9825 (8)	0.5743 (4)	0.20579 (12)	0.0150 (8)
C2	0.8025 (8)	0.5849 (4)	0.24609 (12)	0.0135 (8)
C3	0.6780 (8)	0.7039 (4)	0.25889 (12)	0.0156 (9)
H3	0.723443	0.781513	0.243631	0.019*
C4	0.4888 (8)	0.7099 (4)	0.29364 (12)	0.0168 (9)
H4	0.407880	0.790869	0.301780	0.020*
C5	0.4194 (8)	0.5940 (4)	0.31650 (11)	0.0117 (8)
C6	0.5553 (8)	0.4750 (4)	0.30576 (12)	0.0161 (8)
H6	0.519516	0.398578	0.322296	0.019*
C7	0.7427 (8)	0.4703 (4)	0.27069 (12)	0.0163 (9)
H7	0.830172	0.390229	0.263318	0.020*
C8	0.0577 (8)	0.6914 (4)	0.36404 (12)	0.0137 (8)
H8	0.082942	0.774555	0.351007	0.016*
C9	−0.1484 (8)	0.6767 (4)	0.39755 (12)	0.0133 (8)
C10	−0.1987 (8)	0.5486 (4)	0.41710 (12)	0.0134 (8)
C11	−0.4107 (8)	0.5431 (4)	0.45140 (12)	0.0149 (9)
C12	−0.5604 (9)	0.6534 (4)	0.46335 (12)	0.0162 (8)
H12	−0.697197	0.646746	0.485520	0.019*
C13	−0.5121 (8)	0.7778 (4)	0.44273 (12)	0.0175 (9)
H13	−0.618318	0.851778	0.451168	0.021*
C14	−0.3108 (8)	0.7897 (4)	0.41061 (12)	0.0162 (9)
H14	−0.279196	0.871695	0.397153	0.019*
C15	−0.6548 (9)	0.4036 (4)	0.50242 (13)	0.0216 (10)
H15A	−0.838233	0.422645	0.489935	0.032*
H15B	−0.617086	0.464455	0.526284	0.032*
H15C	−0.652337	0.313983	0.513495	0.032*
C16	0.4392 (9)	1.1681 (4)	0.40083 (13)	0.0226 (9)
H16A	0.377953	1.093074	0.383559	0.034*
H16B	0.323804	1.244117	0.393731	0.034*
H16C	0.420226	1.147815	0.431800	0.034*
N1	0.2152 (6)	0.5912 (3)	0.35065 (10)	0.0128 (7)
H1	0.191331	0.516474	0.364068	0.015*
O1	1.0635 (6)	0.4688 (3)	0.19035 (9)	0.0244 (7)
O2	1.0413 (6)	0.6916 (2)	0.18743 (8)	0.0185 (6)
H2	1.128598	0.680031	0.164203	0.028*
O3	−0.0617 (6)	0.4431 (2)	0.40503 (8)	0.0159 (6)
O4	−0.4410 (6)	0.4183 (3)	0.46896 (8)	0.0185 (6)
O5	0.7301 (6)	1.1970 (3)	0.39101 (9)	0.0192 (6)
H5O	0.795 (11)	1.280 (5)	0.4034 (16)	0.049 (15)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.014 (2)	0.016 (2)	0.0152 (19)	−0.0037 (18)	−0.0028 (17)	0.0022 (16)
C2	0.0111 (19)	0.014 (2)	0.0151 (19)	0.0001 (18)	−0.0019 (16)	−0.0005 (16)
C3	0.016 (2)	0.012 (2)	0.0190 (19)	−0.0024 (18)	0.0022 (17)	0.0026 (16)
C4	0.016 (2)	0.0114 (19)	0.022 (2)	0.0007 (18)	0.0053 (18)	−0.0034 (16)
C5	0.0084 (17)	0.016 (2)	0.0110 (18)	−0.0041 (17)	−0.0013 (16)	−0.0014 (15)
C6	0.0147 (19)	0.015 (2)	0.018 (2)	0.0004 (17)	0.0007 (18)	0.0051 (16)
C7	0.017 (2)	0.014 (2)	0.018 (2)	0.0037 (18)	−0.0006 (18)	−0.0011 (16)
C8	0.0125 (18)	0.0132 (19)	0.0155 (19)	−0.0008 (18)	−0.0037 (16)	−0.0013 (15)
C9	0.0106 (18)	0.015 (2)	0.0145 (19)	0.0034 (16)	−0.0026 (16)	−0.0007 (16)
C10	0.0091 (18)	0.018 (2)	0.0132 (18)	−0.0011 (16)	−0.0057 (16)	−0.0018 (16)
C11	0.012 (2)	0.018 (2)	0.0147 (19)	−0.0022 (17)	−0.0030 (16)	−0.0003 (16)
C12	0.0139 (19)	0.022 (2)	0.0125 (19)	−0.0008 (18)	0.0011 (17)	−0.0004 (16)
C13	0.013 (2)	0.019 (2)	0.021 (2)	0.0011 (17)	−0.0017 (18)	−0.0046 (16)
C14	0.015 (2)	0.016 (2)	0.0175 (19)	−0.0052 (17)	−0.0032 (17)	−0.0011 (17)
C15	0.019 (2)	0.024 (2)	0.021 (2)	0.000 (2)	0.0052 (18)	0.0036 (18)
C16	0.016 (2)	0.026 (2)	0.025 (2)	0.0012 (19)	−0.0024 (19)	0.0013 (18)
N1	0.0126 (16)	0.0129 (17)	0.0130 (16)	−0.0029 (15)	−0.0009 (14)	0.0015 (13)
O1	0.0321 (17)	0.0155 (15)	0.0256 (15)	0.0024 (13)	0.0129 (14)	−0.0001 (12)
O2	0.0237 (15)	0.0145 (14)	0.0174 (14)	−0.0034 (13)	0.0081 (13)	0.0000 (11)
O3	0.0147 (13)	0.0149 (14)	0.0182 (13)	0.0010 (12)	0.0029 (12)	−0.0012 (11)
O4	0.0172 (13)	0.0185 (14)	0.0197 (14)	0.0012 (13)	0.0071 (12)	0.0053 (12)
O5	0.0163 (14)	0.0205 (15)	0.0209 (14)	−0.0015 (14)	0.0047 (12)	−0.0042 (13)

Geometric parameters (Å, º) top

C1—O1	1.217 (4)	C8—C9	1.408 (5)
C1—O2	1.331 (4)	C9—C14	1.422 (5)
C1—C2	1.484 (5)	C9—C10	1.434 (5)
C2—C3	1.384 (5)	C10—O3	1.292 (4)
C2—C7	1.397 (5)	C10—C11	1.437 (5)
C3—C4	1.376 (5)	C11—C12	1.360 (5)
C4—C5	1.392 (5)	C11—O4	1.367 (4)
C5—C6	1.393 (5)	C12—C13	1.414 (5)
C5—N1	1.408 (4)	C13—C14	1.359 (5)
C6—C7	1.377 (5)	C15—O4	1.432 (4)
C8—N1	1.312 (5)	C16—O5	1.429 (5)

O1—C1—O2	123.1 (3)	C8—C9—C14	119.0 (3)
O1—C1—C2	123.6 (3)	C8—C9—C10	120.2 (3)
O2—C1—C2	113.3 (3)	C14—C9—C10	120.8 (3)
C3—C2—C7	118.5 (3)	O3—C10—C9	122.5 (3)
C3—C2—C1	122.1 (3)	O3—C10—C11	121.1 (3)
C7—C2—C1	119.4 (3)	C9—C10—C11	116.4 (3)
C4—C3—C2	121.6 (4)	C12—C11—O4	126.1 (3)
C3—C4—C5	119.4 (3)	C12—C11—C10	121.2 (3)
C4—C5—C6	119.7 (3)	O4—C11—C10	112.7 (3)
C4—C5—N1	122.6 (3)	C11—C12—C13	121.3 (4)
C6—C5—N1	117.8 (3)	C14—C13—C12	120.1 (4)
C7—C6—C5	120.1 (3)	C13—C14—C9	120.1 (4)
C6—C7—C2	120.6 (3)	C8—N1—C5	126.5 (3)
N1—C8—C9	121.9 (3)	C11—O4—C15	116.1 (3)

O1—C1—C2—C3	−169.8 (4)	C8—C9—C10—C11	179.3 (3)
O2—C1—C2—C3	8.6 (5)	C14—C9—C10—C11	−2.6 (5)
O1—C1—C2—C7	6.5 (5)	O3—C10—C11—C12	−178.3 (3)
O2—C1—C2—C7	−175.1 (3)	C9—C10—C11—C12	2.0 (5)
C7—C2—C3—C4	−3.0 (6)	O3—C10—C11—O4	1.1 (5)
C1—C2—C3—C4	173.3 (3)	C9—C10—C11—O4	−178.6 (3)
C2—C3—C4—C5	−0.2 (6)	O4—C11—C12—C13	−179.7 (3)
C3—C4—C5—C6	4.0 (6)	C10—C11—C12—C13	−0.4 (6)
C3—C4—C5—N1	−176.2 (3)	C11—C12—C13—C14	−0.7 (6)
C4—C5—C6—C7	−4.5 (6)	C12—C13—C14—C9	0.2 (5)
N1—C5—C6—C7	175.7 (3)	C8—C9—C14—C13	179.7 (3)
C5—C6—C7—C2	1.2 (6)	C10—C9—C14—C13	1.6 (5)
C3—C2—C7—C6	2.5 (6)	C9—C8—N1—C5	177.6 (3)
C1—C2—C7—C6	−173.9 (3)	C4—C5—N1—C8	3.2 (6)
N1—C8—C9—C14	179.7 (3)	C6—C5—N1—C8	−176.9 (3)
N1—C8—C9—C10	−2.2 (5)	C12—C11—O4—C15	1.2 (5)
C8—C9—C10—O3	−0.4 (5)	C10—C11—O4—C15	−178.1 (3)
C14—C9—C10—O3	177.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3	0.86	1.87	2.568 (4)	138
O2—H2···O5ⁱ	0.82	1.80	2.598 (4)	164
O5—H5O···O3ⁱⁱ	0.96 (5)	1.77 (5)	2.690 (4)	159 (4)
C7—H7···O2ⁱ	0.93	2.56	3.233 (5)	130
C8—H8···O1ⁱⁱⁱ	0.93	2.41	3.281 (5)	155

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

Acknowledgements

The Department of Chemistry, Langat Singh College and the Department of Applied Chemistry, Aligarh Muslim University, Aligarh, are thanked for providing laboratory facilities.

Funding information

The authors are grateful to the National Taras Shevchenko University, Department of Chemistry, and the University Grants Commission, New Delhi, for financial support.

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