Crystal structure of 4-[(2-hy­droxy-3-meth­oxy­benz­yl)amino]­benzoic acid hemihydrate

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

doi:10.1107/S2056989018018455

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Volume 75| Part 2| February 2019| Pages 159-162

https://doi.org/10.1107/S2056989018018455

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Crystal structure of 4-[(2-hydroxy-3-methoxybenzyl)amino]benzoic acid hemihydrate

Saima Kamaal,^a Md. Serajul Haque Faizi,^b ^* Arif Ali,^a Musheer Ahmad,^a Mayank Gupta,^c Necmi Dege ^d and Turganbay Iskenderov ^e ^*

^aDepartment of Applied Chemistry, Faculty of Engineering & Technology, Aligarh Muslim University, Aligarh UP 202 002, India, ^bDepartment of Chemistry, Langat Singh College, B. R. A. Bihar University, Muzaffarpur, Bihar 842 001, India, ^cDepartment of Chemistry, Indian Institute of Technology Kanpur 208016 UP, India, ^dOndokuz Mayıs University, Arts and Sciences Faculty, Department of Physics, 55139 Samsun, Turkey, and ^eNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str., 64, 01601 Kyiv, Ukraine
^*Correspondence e-mail: faizichemiitg@gmail.com, tiskenderov@ukr.net

Edited by S. V. Lindeman, Marquette University, USA (Received 29 November 2018; accepted 29 December 2018; online 8 January 2019)

In the crystal of the title vanilline derivative, 2C₁₅H₁₅NO₄·H₂O, the secondary amine molecule is accompanied by half equivalent of water. The molecule is non-planar, with torsion angle C_aryl—CH₂—NH—C_aryl of −83.9 (2)°. In the crystal, the system of O—H⋯O hydrogen bonds, including bridging water molecules residing on crystallographic twofold axes, results in a two-dimensional layered structure. Within the layers, there are also weak N—H⋯π interactions involving the vanilline benzene ring.

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

CCDC reference: 1888072

1. Chemical context

The title compound is obtained by reduction of reported (Kamaal et al., 2018 ) (E)-4-(2-hydroxy-3-methoxybenzylideneamino)benzoic acid with sodiumborohydride. The Schiff base is formed by condensation of 4-aminobenzoic acid with o-vanilline. Both p-aminobenzoic acid and o-vanilline have biological importance, for example as a bacterial cofactor involved in the synthesis of folic acid (Robinson, 1966 ). Another example is benzocaine, the ethyl ester of p-aminobenzoic acid, which is a local anaesthetic. The mechanism includes inhibiting voltage-dependent sodium channels on the nerve membrane, which results in stopping the signal propagation (Neumcke et al., 1981 ). The present work is also a part of an ongoing structural study of Schiff bases and secondary amines for their utilization in the synthesis of new organic compounds and application of excited-state proton transfer and fluorescent chemosensor (Faizi et al., 2016a ,b , 2018a ,b ; Kumar et al., 2018 ; Mukherjee et al., 2018 ).

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The title compound has two substituted aromatic rings at either end of the –CH₂-NH– linkage [C_aryl—CH₂—NH—C_aryl torsion angle = −83.9 (2)°]. The water solvent stabilizes the crystal structure through hydrogen bonding. The secondary amine N atom has a practically planar trigonal configuration deviating by just 0.03 (1) Å from the mean plane of the adjacent atoms, and it is apparently conjugated with the adjacent benzene ring [the C—N bond length is 1.368 (2) Å]. For comparison, the reported C—N distance in crystal structure of the ethyl 4-[(E)-(4-hydroxy-3-methoxybenzylidene)amino]benzoate Schiff base is 1.274 (2) Å (Ling et al., 2016 ) and in the zwitterion it is 1.312 Å (Kamaal et al., 2018). The C6—O2 bond of the hydroxyl group [1.371 (2)Å] and those of the acid moiety [O3—C15 = 1.224 (2) and O4—C15 = 1.317 (2) Å] are in the expected ranges. The C5—O1 bond length to the methoxy group is 1.372 (2) Å.

Figure 1
The molecular structure of the title compound, showing the atom labelling. The intermolecular O—H⋯O hydrogen bond involving the water molecule is shown as a dashed line (see Table 1

for details). Displacement ellipsoids are drawn at the 40% probability level.

3. Supramolecular features

In the crystal, molecules are connected via O—H⋯O interactions forming layers in the ab plane (Table 1, Fig. 2). While the N—H group is not involved in traditional hydrogen-bonding interactions, there are intermolecular N—H⋯π interactions within the layers (Table 1, Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5⋯O2ⁱ	0.82 (2)	2.06 (2)	2.8640 (19)	164 (3)
O2—H2A⋯O3ⁱⁱ	0.93 (3)	1.82 (3)	2.6844 (17)	154 (2)
O4—H4A⋯O5	0.94 (3)	1.81 (3)	2.6776 (15)	153 (3)
N1—H1⋯Cg1ⁱⁱⁱ	0.96 (2)	2.40 (2)	3.3008 (18)	157 (2)
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) x, y-1, z.

Figure 2
A view of the crystal packing of the title compound.

Figure 3
A view along the c axis of the zigzag chain in the crystal of the title compound. The N—H⋯π interactions are shown as dashed lines (see Table 1

for details).

4. Database survey

A search through the Cambridge Structural Database (CSD, Version 5.39, update Aug 2018; Groom et al., 2016 ) gave nine hits for the secondary amine. There are only two examples of similar compounds in the literature: ethyl 4-{[(2-hydroxyphenyl)methyl]amino}benzoate, (I) (WEFQEG; Salman et al., 2017 ), and ethyl 4-[(3,5-di-tert-butyl-2-hydroxybenzyl)amino]benzoate, (II) (VABTAV;. Shakir et al., 2010 ). Other related structures based on benzylidene-phenyl-amine are reported as n-propyl 4-[2-(4,6-dimethoxypyrimidin-2-yloxy)benzylamino]benzoate, (III) (ILAGIL; Wu et al., 2003 ), and [4-(2-hydroxybenzylamino)benzoato-κO]triphenyltin(IV), (IV) (WENXAP; Jiang et al., 2006 ), There is also one very similar compound, viz. ethyl 4-[(2-hydroxybenzyl)amino]benzoate (Salman et al., 2017), in which the 3-methoxy group in the title compound is replaced by a hydrogen atom and the carboxylic acid is replaced by an ester. The torsion angle C_aryl—CH₂—NH—C_aryl in the title compound [−83.9 (2)°] compares well to those in I (73.68°), II (77.38°) and IV (−87.28°) despite the difference in substituent groups.

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 resultant mixture was then heated under reflux. After an hour, precipitates were formed. The reaction mixture was heated for about a further 30 minutes for the completion of the reaction, which was monitored through TLC. The reaction mixture was cooled to room temperature, filtered and washed with hot methanol. It was then dried in a vacuum to give (E)-4-(2-hydroxy-3-methoxybenzylideneamino)benzoic acid (1) in 78% yield.

Compound (1) (1.00 g, 3.7 mmol) was dissolved in 25 mL of methanol and reduced by addition of excess sodium borohydride (0.28 g, 7.4 mmol). The solution was stirred until the yellow colour disappeared. Then the solution was diluted with 8–10 times the volume of water and the pH was adjusted to 6 by addition of 12% HCl. The white precipitate was collected and dried in air. 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 H atoms were located in difference-Fourier maps and freely refined, while the C-bound H atoms were included in calculated positions and treated as riding, with fixed C—H = 0.93 Å, and U_iso(H) = 1.2U_eq(C,N).

Table 2
Experimental details

Crystal data
Chemical formula	2C₁₅H₁₅NO₄·H₂O
M_r	564.57
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	296
a, b, c (Å)	24.742 (3), 5.5002 (6), 19.387 (2)
β (°)	98.292 (6)
V (Å³)	2610.8 (5)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.11
Crystal size (mm)	0.45 × 0.34 × 0.14

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2014 )
No. of measured, independent and observed [I > 2σ(I)] reflections	16146, 2570, 2138
R_int	0.065
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.107, 1.05
No. of reflections	2570
No. of parameters	203
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.22
Computer programs: APEX2 and SAINT (Bruker, 2014), SHELXT2014 (Sheldrick, 2015a ), SHELXL2018 (Sheldrick, 2015b ) and SHELXTL (Sheldrick, 2008 ).

Supporting information

CCDC reference: 1888072

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018018455/ld2147sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018018455/ld2147Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989018018455/ld2147Isup3.cml

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015b); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

4-[(2-Hydroxy-3-methoxybenzyl)amino]benzoic acid hemihydrate top

Crystal data top

2C₁₅H₁₅NO₄·H₂O	F(000) = 1192
M_r = 564.57	D_x = 1.436 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 24.742 (3) Å	Cell parameters from 6409 reflections
b = 5.5002 (6) Å	θ = 2.5–28.2°
c = 19.387 (2) Å	µ = 0.11 mm⁻¹
β = 98.292 (6)°	T = 296 K
V = 2610.8 (5) Å³	Prism, colorless
Z = 4	0.45 × 0.34 × 0.14 mm

Data collection top

Bruker APEXII CCD diffractometer	2138 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.065
Absorption correction: multi-scan (SADABS; Bruker, 2014)	θ_max = 26.0°, θ_min = 2.9°
	h = −30→30
16146 measured reflections	k = −6→6
2570 independent reflections	l = −23→23

Refinement top

Refinement on F²	1 restraint
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.042	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.107	w = 1/[σ²(F_o²) + (0.0366P)² + 3.8398P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2570 reflections	Δρ_max = 0.26 e Å⁻³
203 parameters	Δρ_min = −0.22 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.

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

	x	y	z	U_iso*/U_eq
O2	0.95635 (5)	0.7070 (2)	0.67260 (6)	0.0206 (3)
O5	0.500000	0.7903 (3)	0.750000	0.0222 (4)
O1	0.97314 (5)	1.0831 (2)	0.59182 (6)	0.0238 (3)
O3	0.56242 (5)	0.2504 (2)	0.65933 (7)	0.0271 (3)
O4	0.58989 (5)	0.6076 (3)	0.70737 (8)	0.0347 (4)
N1	0.81774 (6)	0.2583 (3)	0.63512 (8)	0.0197 (3)
C14	0.74975 (6)	0.5056 (3)	0.68083 (8)	0.0168 (3)
H14	0.775566	0.623501	0.696467	0.020*
C9	0.76511 (6)	0.2985 (3)	0.64627 (8)	0.0158 (3)
C12	0.65625 (6)	0.3621 (3)	0.66873 (8)	0.0174 (4)
C15	0.59858 (7)	0.3981 (3)	0.67792 (9)	0.0194 (4)
C7	0.86973 (6)	0.6259 (3)	0.60621 (9)	0.0177 (4)
C10	0.72476 (7)	0.1239 (3)	0.62307 (9)	0.0181 (4)
H10	0.734254	−0.014204	0.599877	0.022*
C13	0.69600 (7)	0.5340 (3)	0.69160 (8)	0.0174 (3)
H13	0.686232	0.671711	0.714756	0.021*
C5	0.92543 (7)	0.9565 (3)	0.57298 (9)	0.0187 (4)
C6	0.91728 (6)	0.7641 (3)	0.61739 (8)	0.0175 (4)
C2	0.83105 (7)	0.6781 (3)	0.54820 (9)	0.0206 (4)
H2	0.799081	0.587223	0.539822	0.025*
C8	0.86335 (6)	0.4187 (3)	0.65624 (9)	0.0184 (4)
H8A	0.896629	0.323016	0.662065	0.022*
H8B	0.859392	0.487346	0.701326	0.022*
C4	0.88690 (7)	1.0051 (3)	0.51542 (9)	0.0220 (4)
H4	0.892432	1.131150	0.485232	0.026*
C11	0.67166 (7)	0.1554 (3)	0.63432 (9)	0.0182 (4)
H11	0.645659	0.037923	0.618889	0.022*
C3	0.83997 (7)	0.8641 (3)	0.50316 (9)	0.0236 (4)
H3	0.814245	0.895045	0.464242	0.028*
C1	0.98495 (8)	1.2765 (3)	0.54726 (10)	0.0262 (4)
H1A	0.986748	1.213811	0.501435	0.039*
H1B	1.019360	1.348797	0.565539	0.039*
H1C	0.956674	1.397043	0.544826	0.039*
H5	0.5159 (12)	0.891 (5)	0.7772 (13)	0.076 (10)*
H1	0.8246 (9)	0.120 (4)	0.6076 (12)	0.038 (6)*
H2A	0.9900 (10)	0.771 (5)	0.6651 (13)	0.050 (7)*
H4A	0.5536 (12)	0.630 (6)	0.7145 (15)	0.073 (9)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O2	0.0122 (6)	0.0235 (7)	0.0262 (6)	−0.0025 (5)	0.0029 (5)	0.0043 (5)
O5	0.0150 (8)	0.0244 (10)	0.0277 (10)	0.000	0.0043 (7)	0.000
O1	0.0199 (6)	0.0212 (7)	0.0313 (7)	−0.0052 (5)	0.0067 (5)	0.0063 (5)
O3	0.0136 (6)	0.0270 (7)	0.0411 (8)	−0.0032 (5)	0.0055 (5)	−0.0011 (6)
O4	0.0173 (7)	0.0366 (8)	0.0524 (9)	0.0000 (6)	0.0127 (6)	−0.0187 (7)
N1	0.0137 (7)	0.0186 (7)	0.0280 (8)	−0.0020 (6)	0.0071 (6)	−0.0034 (6)
C14	0.0150 (8)	0.0163 (8)	0.0191 (8)	−0.0038 (6)	0.0020 (6)	−0.0007 (6)
C9	0.0132 (7)	0.0169 (8)	0.0173 (8)	0.0001 (6)	0.0025 (6)	0.0030 (6)
C12	0.0148 (8)	0.0192 (8)	0.0184 (8)	0.0004 (7)	0.0037 (6)	0.0024 (7)
C15	0.0166 (8)	0.0220 (9)	0.0201 (8)	0.0010 (7)	0.0042 (6)	0.0013 (7)
C7	0.0156 (8)	0.0184 (8)	0.0207 (8)	0.0012 (7)	0.0084 (6)	−0.0023 (7)
C10	0.0176 (8)	0.0145 (8)	0.0224 (8)	0.0004 (7)	0.0035 (7)	−0.0002 (7)
C13	0.0176 (8)	0.0172 (8)	0.0178 (8)	0.0012 (7)	0.0039 (6)	−0.0011 (7)
C5	0.0161 (8)	0.0180 (8)	0.0236 (9)	0.0000 (7)	0.0083 (7)	−0.0010 (7)
C6	0.0149 (8)	0.0187 (8)	0.0198 (8)	0.0030 (7)	0.0057 (6)	−0.0020 (7)
C2	0.0159 (8)	0.0232 (9)	0.0230 (9)	−0.0007 (7)	0.0038 (7)	−0.0033 (7)
C8	0.0116 (7)	0.0196 (9)	0.0246 (9)	−0.0012 (7)	0.0043 (6)	0.0003 (7)
C4	0.0249 (9)	0.0215 (9)	0.0211 (9)	0.0028 (7)	0.0082 (7)	0.0034 (7)
C11	0.0157 (8)	0.0150 (8)	0.0239 (9)	−0.0040 (6)	0.0026 (6)	0.0009 (7)
C3	0.0217 (9)	0.0287 (10)	0.0202 (9)	0.0018 (8)	0.0025 (7)	−0.0001 (7)
C1	0.0290 (10)	0.0180 (9)	0.0351 (10)	−0.0029 (8)	0.0159 (8)	0.0043 (8)

Geometric parameters (Å, º) top

O2—C6	1.371 (2)	C7—C6	1.391 (2)
O2—H2A	0.93 (3)	C7—C2	1.398 (2)
O5—H5	0.823 (17)	C7—C8	1.519 (2)
O5—H5ⁱ	0.823 (17)	C10—C11	1.374 (2)
O1—C5	1.374 (2)	C10—H10	0.9300
O1—C1	1.427 (2)	C13—H13	0.9300
O3—C15	1.224 (2)	C5—C4	1.385 (2)
O4—C15	1.317 (2)	C5—C6	1.397 (2)
O4—H4A	0.94 (3)	C2—C3	1.383 (3)
N1—C9	1.368 (2)	C2—H2	0.9300
N1—C8	1.445 (2)	C8—H8A	0.9700
N1—H1	0.96 (2)	C8—H8B	0.9700
C14—C13	1.384 (2)	C4—C3	1.388 (3)
C14—C9	1.401 (2)	C4—H4	0.9300
C14—H14	0.9300	C11—H11	0.9300
C9—C10	1.411 (2)	C3—H3	0.9300
C12—C13	1.390 (2)	C1—H1A	0.9600
C12—C11	1.399 (2)	C1—H1B	0.9600
C12—C15	1.477 (2)	C1—H1C	0.9600

C6—O2—H2A	109.7 (15)	O1—C5—C6	114.50 (15)
H5—O5—H5ⁱ	96 (4)	C4—C5—C6	119.92 (16)
C5—O1—C1	117.37 (14)	O2—C6—C7	118.78 (15)
C15—O4—H4A	113.6 (19)	O2—C6—C5	120.42 (15)
C9—N1—C8	125.37 (15)	C7—C6—C5	120.79 (15)
C9—N1—H1	117.7 (13)	C3—C2—C7	120.46 (16)
C8—N1—H1	116.7 (13)	C3—C2—H2	119.8
C13—C14—C9	119.78 (15)	C7—C2—H2	119.8
C13—C14—H14	120.1	N1—C8—C7	115.22 (14)
C9—C14—H14	120.1	N1—C8—H8A	108.5
N1—C9—C14	122.47 (15)	C7—C8—H8A	108.5
N1—C9—C10	119.03 (15)	N1—C8—H8B	108.5
C14—C9—C10	118.50 (14)	C7—C8—H8B	108.5
C13—C12—C11	118.44 (15)	H8A—C8—H8B	107.5
C13—C12—C15	121.46 (15)	C5—C4—C3	119.45 (16)
C11—C12—C15	120.06 (15)	C5—C4—H4	120.3
O3—C15—O4	123.39 (15)	C3—C4—H4	120.3
O3—C15—C12	123.62 (16)	C10—C11—C12	120.71 (15)
O4—C15—C12	112.98 (15)	C10—C11—H11	119.6
C6—C7—C2	118.60 (16)	C12—C11—H11	119.6
C6—C7—C8	118.28 (15)	C2—C3—C4	120.72 (16)
C2—C7—C8	123.08 (15)	C2—C3—H3	119.6
C11—C10—C9	120.84 (15)	C4—C3—H3	119.6
C11—C10—H10	119.6	O1—C1—H1A	109.5
C9—C10—H10	119.6	O1—C1—H1B	109.5
C14—C13—C12	121.73 (15)	H1A—C1—H1B	109.5
C14—C13—H13	119.1	O1—C1—H1C	109.5
C12—C13—H13	119.1	H1A—C1—H1C	109.5
O1—C5—C4	125.57 (16)	H1B—C1—H1C	109.5

C8—N1—C9—C14	−0.4 (3)	C8—C7—C6—C5	179.87 (15)
C8—N1—C9—C10	−179.51 (15)	O1—C5—C6—O2	−3.0 (2)
C13—C14—C9—N1	−178.88 (15)	C4—C5—C6—O2	176.85 (15)
C13—C14—C9—C10	0.2 (2)	O1—C5—C6—C7	177.53 (14)
C13—C12—C15—O3	−179.11 (16)	C4—C5—C6—C7	−2.7 (2)
C11—C12—C15—O3	3.0 (3)	C6—C7—C2—C3	−0.2 (2)
C13—C12—C15—O4	1.8 (2)	C8—C7—C2—C3	−177.81 (16)
C11—C12—C15—O4	−176.06 (15)	C9—N1—C8—C7	−83.9 (2)
N1—C9—C10—C11	178.86 (15)	C6—C7—C8—N1	−170.01 (14)
C14—C9—C10—C11	−0.3 (2)	C2—C7—C8—N1	7.6 (2)
C9—C14—C13—C12	−0.3 (2)	O1—C5—C4—C3	−179.06 (16)
C11—C12—C13—C14	0.3 (2)	C6—C5—C4—C3	1.2 (2)
C15—C12—C13—C14	−177.56 (15)	C9—C10—C11—C12	0.4 (3)
C1—O1—C5—C4	−2.0 (2)	C13—C12—C11—C10	−0.4 (2)
C1—O1—C5—C6	177.78 (14)	C15—C12—C11—C10	177.54 (15)
C2—C7—C6—O2	−177.34 (14)	C7—C2—C3—C4	−1.3 (3)
C8—C7—C6—O2	0.3 (2)	C5—C4—C3—C2	0.8 (3)
C2—C7—C6—C5	2.2 (2)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5···O2ⁱⁱ	0.82 (2)	2.06 (2)	2.8640 (19)	164 (3)
O2—H2A···O3ⁱⁱⁱ	0.93 (3)	1.82 (3)	2.6844 (17)	154 (2)
O4—H4A···O5	0.94 (3)	1.81 (3)	2.6776 (15)	153 (3)
N1—H1···Cg1^iv	0.96 (2)	2.40 (2)	3.3008 (18)	157 (2)

Symmetry codes: (ii) −x+3/2, y+1/2, −z+3/2; (iii) x+1/2, y+1/2, z; (iv) x, y−1, z.

Acknowledgements

The authors thank the Department of Chemistry, L. S. College, B. R. A. Bihar University, and the Department of Applied Chemistry, Faculty of Engineering & Technology, Aligarh Muslim University, for providing laboratory facilities.

Funding information

The authors are grateful to the Department of Chemistry, National Taras Shevchenko University, for financial support.

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