Crystal structure and Hirshfeld surface analysis of tetra­aqua­bis­(isonicotinamide-κN1)nickel(II) fumarate

Kansiz, S.; Golenya, I.A.; Dege, N.

doi:10.1107/S2056989018013580

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ISSN: 2056-9890

Volume 74| Part 11| November 2018| Pages 1536-1539

https://doi.org/10.1107/S2056989018013580

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Crystal structure and Hirshfeld surface analysis of tetraaquabis(isonicotinamide-κN¹)nickel(II) fumarate

Sevgi Kansiz,^a Irina A. Golenya ^b ^* and Necmi Dege ^a

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Kurupelit, Samsun, Turkey, and ^bTaras Shevchenko National University of Kyiv, Department of Chemistry, 64, Vladimirska Str., Kiev 01601, Ukraine
^*Correspondence e-mail: igolenya@ua.fm

Edited by P. McArdle, National University of Ireland, Ireland (Received 6 July 2018; accepted 24 September 2018; online 2 October 2018)

The reaction of NiCl₂ with fumaric acid and isonicotinamide in a basic solution produces the title complex, [Ni(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄). The nickel(II) ion of the complex cation and the fumarate anion are each located on an inversion centre. The Ni^II ion is coordinated octahedrally by four water O atoms and two N atoms of isonicotinamide molecules. The fumarate anion is linked to neighbouring complex cations via O_water—H⋯O_fumarate hydrogen bonds. In the crystal, the complex cations are further linked by O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular architecture. Hirshfeld surface analysis and two-dimensional fingerprint plots were used to analyse the intermolecular interactions present in the crystal and indicate that the most important contributions for the crystal packing are from H⋯O/O⋯H (41.8%), H⋯H (35.3%) and H⋯C/C⋯H (10.2%) interactions.

Keywords: crystal structure; fumaric acid; isonicotinamide; nickel(II); Hirshfeld surface.

CCDC reference: 1579677

1. Chemical context

Metal complexes of biologically important ligands are sometimes more effective than the free ligands. Many transition and heavy metal cations play an important role in the biological processes involved in the formation of vitamins and drug components. An important element for biological systems is nickel and nickel complexes have biological activities including antiepileptic, antimicrobial, antibacterial and anticancer activities (Bombicz et al., 2001 ). Dicarboxylic acid ligands have been utilized primarily in the synthesis of a range of metal complexes. Dicarboxylic acids such as fumaric acid and amides have been particularly useful in creating many supramolecular structures (Pavlishchuk et al., 2011 ; Ostrowska et al., 2016 ), in particular isonicotinamide with a variety of carboxylic acids (Vishweshwar et al., 2003 ; Aakeröy et al., 2002 ).

We have prepared a new Ni^II complex, tetraaquabis(isonicotinamide-κN¹)nickel(II) fumarate, and determined its structure by single crystal X-ray diffraction. In addition, Hirshfeld surface analysis and fingerprint plots were used to understand the intermolecular interactions in the crystal structure.

2. Structural commentary

The molecular structure of the title complex is illustrated in Fig. 1. The nickel(II) ion is octahedrally coordinated to four water O atoms and two N_pyridine atoms of isonicotinamide molecules. The values of the Ni—O_water and Ni—N_pyridine bond lengths and the bond angles involving atom Ni1 (Table 1) are close to those reported for similar nickel(II) complexes (Krämer et al., 2002 ; Bora & Das, 2011 ; Moroz et al., 2012 ).

Table 1
Selected geometric parameters (Å, °)

Ni1—O3	2.0537 (16)	Ni1—N1	2.1075 (18)
Ni1—O2	2.0812 (15)

O3—Ni1—O2	92.00 (7)	O3—Ni1—N1	86.97 (7)
O3—Ni1—O2ⁱ	88.00 (7)	O2—Ni1—N1	92.05 (6)
O3ⁱ—Ni1—N1	93.03 (7)	O2ⁱ—Ni1—N1	87.95 (7)
Symmetry code: (i) -x+1, -y+1, -z+1.

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 20% probability level. [Symmetry codes: (i) −x + 1, −y + 1, −z + 1; (ii) −x + 1, −y + 1, −z.]

3. Supramolecular features

In the crystal, each O atom of the fumarate dianion is linked to a water H atom via O—H⋯O hydrogen bonds, forming chains along the c-axis direction (Table 2, Fig. 2).

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O4	0.80 (3)	1.89 (3)	2.678 (2)	169 (3)
O2—H2A⋯O5	0.78 (3)	2.01 (3)	2.791 (3)	175 (3)
C6—H6⋯O1ⁱⁱⁱ	0.93	2.31	3.230 (3)	172
N2—H2D⋯O1ⁱⁱⁱ	0.93 (5)	2.31 (5)	3.230 (3)	172 (4)
C5—H5⋯O4^iv	0.93	2.38	3.282 (3)	165
O2—H2B⋯O4^iv	0.73 (3)	2.02 (3)	2.739 (2)	172 (3)
O3—H3A⋯O1^v	0.73 (3)	2.07 (3)	2.798 (3)	175 (3)
Symmetry codes: (iii) $[-x+2, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) $[-x+1, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (v) x-1, y, z.

Figure 2
A view of the crystal packing of the title compound. Dashed lines indicate hydrogen bonds.

The fumarate anions and complex cations are linked by O—H⋯O hydrogen bonds; the complex cations also interact with each other through O—H⋯O, N—H⋯O and C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular architecture.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 5.39, update of May 2018; Groom et al., 2016 ) revealed the structures of four similar tetraaquabis(isonicotinamide-κN¹)nickel(II) complexes with different counter-anions viz. bis(4-formylbenzoate) dihydrate (HUCLAT; Hökelek et al., 2009 ), bis(3-hydroxybenzoate) tetrahydrate (GANZAY; Zaman et al., 2012 ), bis(thiophene-2,5-dicarboxylate) dihydrate (NETQIO; Liu et al., 2012 ) and naphthalene-1,5-disulfonate tetrahydrate (TESDEC; Lian, 2012 ). In all four complexes, the cation possesses inversion symmetry with the nickel ion being located on a centre of symmetry. The Ni—O_water bond lengths vary from 2.044 to 2.086 Å, while the Ni—N_pyridine bond lengths vary from 2.075 to 2.098 Å. In the title complex, the cation also possesses inversion symmetry and the Ni—O_water bond lengths [2.0812 (15) and 2.0537 (16) Å] and the Ni—N_pyridine bond length [2.1075 (18) Å] fall within these limits.

5. Hirshfeld surface analysis

Crystal Explorer17.5 (Turner et al., 2017 ) was used to investigate the Hirshfeld surfaces and to analyse the interactions in the crystal. The Hirshfeld surfaces mapped over d_norm, d_i and d_e are shown in Fig. 3. Red spots indicate the contacts involved in strong hydrogen bonds and interatomic contacts (Gümüş et al., 2018 ; Sen et al., 2018 ; Kansız & Dege, 2018 ); those in Fig. 3 correspond to the near-type H⋯O contacts resulting from C—H⋯O, O—H⋯O and N—H⋯O hydrogen bonds. The Hirshfeld surfaces were obtained using a standard surface (high) resolution with the three-dimensional d_norm surfaces mapped over a fixed colour scale of −0.701 (red) to 1.286 (blue) a.u. The red spots in Fig. 4 correspond to the near-type H⋯O contacts resulting from O—H⋯O and N—H⋯O hydrogen bonds. Fig. 5 shows the two-dimensional fingerprint plot of the sum of the contacts contributing to the Hirshfeld surface represented in normal mode. In Fig. 6a. the two symmetrical points at the top, bottom left and right with d_e + d_i = 1.7 Å indicate the presence of H⋯O/O⋯H (41.8%) contacts. Fig. 6b shows the two-dimensional fingerprint plot of the (d_i, d_e) points associated with hydrogen atoms and is characterized by an end point that points to the origin and corresponds to d_i = d_e = 1.08 Å, which indicates the presence of the H⋯H contacts (35.3%). Fig. 6c shows the contacts between the carbon atoms inside the surface and the hydrogen atoms outside the surface of Hirshfeld and vice versa (H⋯C/C⋯H) and has two symmetrical wings on the left and right sides (10.2%). C⋯C (4.2%), C⋯O/O⋯C (2.9%) and H⋯N/N⋯H (2.7%) contacts also contribute to the Hirshfeld surface.

Figure 3
The Hirshfeld surface of the title compound mapped over d_norm, d_i and d_e.

Figure 4
The Hirshfeld surface mapped over d_norm to visualize the intramolecular and intermolecular interactions in the title compound.

Figure 5
A fingerprint plot of the title compound.

Figure 6
(a) H⋯O/O⋯H, (b) H⋯H, (c) H⋯C/C⋯H, (d) C⋯C, (e) C⋯O/O⋯C and (f) H⋯N/N⋯H contacts in the title complex, showing their percentage contributions to the Hirshfeld surface.

6. Synthesis and crystallization

A solution of NaOH (52 mmol, 2.07 g) was added to an aqueous solution of fumaric acid (26 mmol, 3 g) under stirring. A solution of NiCl₂·6H₂O (25 mmol, 6.14 g) in methanol was then added. The mixture was heated at 353 K for 30 min. and then the blue mixture was filtered and left to dry at room temperature. The reaction mixture (0.88 mmol, 0.20 g) was dissolved in methanol and added to a ethanol solution of isonicotinamide (1.76 mmol, 0.21 g). The mixture was heated at 353 K for 60 min. under stirring and the resulting suspension was filtered and left to crystallize for three weeks at room temperature. The title compound was obtained as a blue solid and contained crystals suitable for X-ray diffraction analysis.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The water and NH₂ hydrogen atoms were located from difference-Fourier maps and freely refined. The C-bound H atoms were positioned geometrically and refined using a riding model: C—H = 0.93–0.97 Å with U_iso(H) = 1.2U_eq(C).

Table 3
Experimental details

Crystal data
Chemical formula	[Ni(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄)
M_r	489.08
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6140 (8), 9.9819 (9), 11.3874 (10)
β (°)	113.157 (7)
V (Å³)	1004.76 (16)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	1.03
Crystal size (mm)	0.58 × 0.50 × 0.39

Data collection
Diffractometer	STOE IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.527, 0.593
No. of measured, independent and observed [I > 2σ(I)] reflections	5175, 2075, 1777
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.104, 1.05
No. of reflections	2075
No. of parameters	171
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.39, −0.83
Computer programs: X-AREA (Stoe & Cie, 2002), X-RED (Stoe & Cie, 2002), SHELXL2017 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), WinGX (Farrugia, 2012) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1579677

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989018013580/qm2126sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018013580/qm2126Isup2.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: WinGX (Farrugia, 2012); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Tetraaquabis(isonicotinamide-κN¹)nickel(II) fumarate top

Crystal data top

[Ni(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄)	F(000) = 508
M_r = 489.08	D_x = 1.617 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6140 (8) Å	Cell parameters from 8294 reflections
b = 9.9819 (9) Å	θ = 2.0–28.5°
c = 11.3874 (10) Å	µ = 1.03 mm⁻¹
β = 113.157 (7)°	T = 296 K
V = 1004.76 (16) Å³	Prism, blue
Z = 2	0.58 × 0.50 × 0.39 mm

Data collection top

STOE IPDS 2 diffractometer	2075 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1777 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.045
rotation method scans	θ_max = 26.5°, θ_min = 2.8°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −12→10
T_min = 0.527, T_max = 0.593	k = −12→12
5175 measured reflections	l = −14→14

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.104	w = 1/[σ²(F_o²) + (0.073P)² + 0.0362P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2075 reflections	Δρ_max = 0.39 e Å⁻³
171 parameters	Δρ_min = −0.82 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. Refined as a 2-component inversion twin.

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

	x	y	z	U_iso*/U_eq
Ni1	0.500000	0.500000	0.500000	0.02691 (15)
O2	0.39639 (19)	0.36038 (17)	0.35626 (16)	0.0352 (3)
O3	0.3976 (2)	0.65707 (16)	0.38085 (15)	0.0345 (3)
O4	0.45031 (18)	0.63766 (14)	0.16741 (14)	0.0399 (4)
O5	0.2761 (2)	0.47778 (18)	0.11437 (18)	0.0473 (4)
O1	1.0888 (2)	0.70001 (16)	0.31656 (18)	0.0506 (4)
N1	0.6822 (2)	0.52490 (16)	0.44312 (18)	0.0315 (4)
C7	0.3828 (2)	0.5393 (2)	0.10101 (19)	0.0328 (4)
C8	0.4341 (3)	0.4863 (2)	0.0015 (2)	0.0357 (5)
N2	1.0342 (3)	0.5042 (3)	0.2095 (3)	0.0605 (7)
C2	0.8968 (2)	0.5673 (2)	0.33931 (19)	0.0344 (4)
C3	0.8503 (3)	0.6699 (2)	0.3963 (2)	0.0402 (5)
H3	0.891089	0.755195	0.401464	0.048*
C4	0.7431 (3)	0.6452 (2)	0.4456 (2)	0.0392 (5)
H4	0.711583	0.715976	0.482316	0.047*
C6	0.8353 (3)	0.4416 (2)	0.3374 (2)	0.0423 (5)
H6	0.864249	0.369442	0.300562	0.051*
C1	1.0136 (3)	0.5951 (2)	0.2856 (2)	0.0402 (5)
C5	0.7303 (3)	0.4249 (2)	0.3910 (2)	0.0401 (5)
H5	0.691168	0.339653	0.390746	0.048*
H3B	0.402 (3)	0.655 (3)	0.312 (3)	0.048 (8)*
H3A	0.318 (3)	0.670 (3)	0.369 (2)	0.038 (7)*
H2B	0.434 (4)	0.297 (3)	0.354 (3)	0.051 (9)*
H2A	0.364 (4)	0.389 (3)	0.287 (3)	0.056 (9)*
H2C	1.030 (6)	0.554 (6)	0.139 (5)	0.133 (17)*
H2D	0.989 (5)	0.420 (5)	0.199 (4)	0.104 (14)*
H8	0.367 (3)	0.424 (3)	−0.058 (3)	0.053 (7)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni1	0.0289 (2)	0.0249 (2)	0.0340 (2)	0.00018 (13)	0.01994 (16)	−0.00068 (12)
O2	0.0414 (9)	0.0306 (8)	0.0386 (8)	0.0005 (7)	0.0210 (7)	−0.0031 (6)
O3	0.0366 (9)	0.0352 (8)	0.0389 (8)	0.0044 (7)	0.0226 (7)	0.0032 (6)
O4	0.0537 (10)	0.0327 (8)	0.0455 (8)	−0.0069 (7)	0.0328 (7)	−0.0049 (6)
O5	0.0479 (10)	0.0543 (10)	0.0529 (10)	−0.0138 (8)	0.0341 (8)	−0.0076 (7)
O1	0.0464 (10)	0.0421 (9)	0.0781 (12)	−0.0012 (7)	0.0405 (9)	0.0097 (8)
N1	0.0330 (9)	0.0291 (8)	0.0412 (9)	−0.0003 (7)	0.0241 (8)	0.0002 (7)
C7	0.0389 (11)	0.0291 (9)	0.0366 (9)	0.0038 (9)	0.0216 (9)	0.0031 (8)
C8	0.0425 (13)	0.0329 (11)	0.0393 (11)	−0.0024 (9)	0.0244 (10)	−0.0040 (8)
N2	0.0581 (16)	0.0683 (18)	0.0789 (18)	−0.0089 (12)	0.0526 (15)	−0.0146 (12)
C2	0.0274 (10)	0.0407 (12)	0.0397 (9)	0.0013 (9)	0.0182 (8)	0.0042 (9)
C3	0.0419 (12)	0.0314 (10)	0.0578 (12)	−0.0019 (9)	0.0309 (11)	0.0025 (9)
C4	0.0429 (12)	0.0305 (10)	0.0544 (12)	−0.0005 (9)	0.0302 (10)	−0.0024 (9)
C6	0.0422 (13)	0.0372 (12)	0.0592 (13)	−0.0031 (10)	0.0325 (11)	−0.0112 (10)
C1	0.0333 (11)	0.0469 (13)	0.0485 (11)	0.0040 (9)	0.0245 (10)	0.0086 (10)
C5	0.0424 (12)	0.0313 (11)	0.0584 (12)	−0.0042 (9)	0.0325 (11)	−0.0069 (9)

Geometric parameters (Å, º) top

Ni1—O3ⁱ	2.0536 (15)	C7—C8	1.499 (3)
Ni1—O3	2.0537 (16)	C8—C8ⁱⁱ	1.309 (5)
Ni1—O2	2.0812 (15)	C8—H8	0.95 (3)
Ni1—O2ⁱ	2.0812 (15)	N2—C1	1.322 (4)
Ni1—N1	2.1075 (18)	N2—H2C	0.93 (6)
Ni1—N1ⁱ	2.1075 (18)	N2—H2D	0.93 (5)
O2—H2B	0.73 (3)	C2—C3	1.378 (3)
O2—H2A	0.78 (3)	C2—C6	1.384 (3)
O3—H3B	0.80 (3)	C2—C1	1.501 (3)
O3—H3A	0.73 (3)	C3—C4	1.376 (3)
O4—C7	1.253 (3)	C3—H3	0.9300
O5—C7	1.255 (3)	C4—H4	0.9300
O1—C1	1.242 (3)	C6—C5	1.379 (3)
N1—C4	1.332 (3)	C6—H6	0.9300
N1—C5	1.334 (3)	C5—H5	0.9300

O3ⁱ—Ni1—O3	180.0	O5—C7—C8	116.5 (2)
O3ⁱ—Ni1—O2	88.00 (7)	C8ⁱⁱ—C8—C7	123.7 (3)
O3—Ni1—O2	92.00 (7)	C8ⁱⁱ—C8—H8	120.6 (17)
O3ⁱ—Ni1—O2ⁱ	92.00 (7)	C7—C8—H8	115.6 (16)
O3—Ni1—O2ⁱ	88.00 (7)	C1—N2—H2C	104 (4)
O2—Ni1—O2ⁱ	180.0	C1—N2—H2D	121 (3)
O3ⁱ—Ni1—N1	93.03 (7)	H2C—N2—H2D	121 (4)
O3—Ni1—N1	86.97 (7)	C3—C2—C6	117.72 (19)
O2—Ni1—N1	92.05 (6)	C3—C2—C1	119.23 (19)
O2ⁱ—Ni1—N1	87.95 (7)	C6—C2—C1	123.0 (2)
O3ⁱ—Ni1—N1ⁱ	86.97 (7)	C4—C3—C2	119.6 (2)
O3—Ni1—N1ⁱ	93.03 (7)	C4—C3—H3	120.2
O2—Ni1—N1ⁱ	87.95 (7)	C2—C3—H3	120.2
O2ⁱ—Ni1—N1ⁱ	92.05 (6)	N1—C4—C3	123.1 (2)
N1—Ni1—N1ⁱ	180.0	N1—C4—H4	118.4
Ni1—O2—H2B	121 (2)	C3—C4—H4	118.4
Ni1—O2—H2A	115 (2)	C5—C6—C2	119.0 (2)
H2B—O2—H2A	107 (3)	C5—C6—H6	120.5
Ni1—O3—H3B	116 (2)	C2—C6—H6	120.5
Ni1—O3—H3A	117 (2)	O1—C1—N2	122.9 (2)
H3B—O3—H3A	106 (3)	O1—C1—C2	119.0 (2)
C4—N1—C5	117.25 (18)	N2—C1—C2	118.0 (2)
C4—N1—Ni1	120.76 (14)	N1—C5—C6	123.3 (2)
C5—N1—Ni1	121.62 (14)	N1—C5—H5	118.4
O4—C7—O5	124.33 (18)	C6—C5—H5	118.4
O4—C7—C8	119.12 (18)

O4—C7—C8—C8ⁱⁱ	17.1 (4)	C1—C2—C6—C5	178.9 (2)
O5—C7—C8—C8ⁱⁱ	−160.8 (3)	C3—C2—C1—O1	15.0 (3)
C6—C2—C3—C4	−1.7 (3)	C6—C2—C1—O1	−163.2 (2)
C1—C2—C3—C4	179.9 (2)	C3—C2—C1—N2	−166.6 (3)
C5—N1—C4—C3	0.6 (4)	C6—C2—C1—N2	15.1 (4)
Ni1—N1—C4—C3	−172.50 (19)	C4—N1—C5—C6	−1.9 (4)
C2—C3—C4—N1	1.2 (4)	Ni1—N1—C5—C6	171.21 (19)
C3—C2—C6—C5	0.6 (3)	C2—C6—C5—N1	1.3 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O4	0.80 (3)	1.89 (3)	2.678 (2)	169 (3)
O2—H2A···O5	0.78 (3)	2.01 (3)	2.791 (3)	175 (3)
C6—H6···O1ⁱⁱⁱ	0.93	2.31	3.230 (3)	172
N2—H2D···O1ⁱⁱⁱ	0.93 (5)	2.31 (5)	3.230 (3)	172 (4)
C5—H5···O4^iv	0.93	2.38	3.282 (3)	165
O2—H2B···O4^iv	0.73 (3)	2.02 (3)	2.739 (2)	172 (3)
O3—H3A···O1^v	0.73 (3)	2.07 (3)	2.798 (3)	175 (3)

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

Acknowledgements

The authors acknowledge the Faculty of Arts and Sciences, Ondokuz Mayıs University, Turkey, for the use of the Stoe IPDS 2 diffractometer (purchased under grant F.279 of the University Research Fund).

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