Synthesis, crystal structure and Hirshfeld surface analysis of tetra­aqua­bis­(isonicotinamide-κN1)cobalt(II) succinate

Kansiz, S.; Malinkin, S.; Dege, N.

doi:10.1107/S2056989018008861

research communications

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 74| Part 7| July 2018| Pages 1026-1029

https://doi.org/10.1107/S2056989018008861

Open

access

Synthesis, crystal structure and Hirshfeld surface analysis of tetraaquabis(isonicotinamide-κN¹)cobalt(II) succinate

Sevgi Kansiz,^a Sergey Malinkin ^b ^* and Necmi Dege ^a

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139 Samsun, Turkey, and ^bDepartment of Chemistry, National Taras Shevchenko University of Kiev, 64/13 Volodymyrska Street, City of Kyiv 01601, Ukraine
^*Correspondence e-mail: malinachem88@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 25 May 2018; accepted 17 June 2018; online 28 June 2018)

The reaction of CoCl₂ with succinic acid and isonicotinamide in basic solution produces the title complex [Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₄O₄). The cobalt(II) ion of the complex cation and the succinate anion are each located on an inversion centre. The Co^II ion is octahedrally coordinated by four O atoms of water molecules and two N atoms of isonicotinamide molecules. The two ions are linked via O_water—H⋯O_succinate hydrogen bonds, forming chains propagating along [001]. In the crystal, these hydrogen-bonded chains are linked into a three-dimensional framework by further O—H⋯O hydrogen bonds and N—H⋯O hydrogen bonds. The framework is reinforced by C—H⋯O hydrogen bonds. Hirshfeld surface analysis and two-dimensional fingerprint plots have been used to analyse the intermolecular interactions present in the crystal.

Keywords: crystal structure; succinic acid; isonicotinamide; cobalt(II); Hirshfeld surfaces; hydrogen bonding.

CCDC reference: 1842712

1. Chemical context

Metal carboxylates have attracted intense attention because of their interesting framework topologies. Among metal carboxylates, succinate dianions (succ) have good conformational freedom and they possess some desirable features such as being a versatile ligand because of the four electron-donor oxygen atoms they carry, and their ability to link inorganic moieties. Metal succinates are one of the best dicarboxylate-based moieties that display an interesting structural variety. Dicarboxylic acids such as succinic acid and amides have been particularly useful in creating many supramolecular structures between isonicotinamide and a variety of carboxylic acid molecules (Vishweshwar et al., 2003 ; Aakeröy et al., 2002 ). Dicarboxylic acid ligands have been utilized frequently in the synthesis of various metal carboxylates. For this reason they have been investigated widely, both experimentally and computationally. We describe herein the synthesis, structural features and Hirshfeld surface analysis of a new tetraaquabis(isonicotinamide-κN¹)cobalt(II) succinate complex.

2. Structural commentary

The molecular structure of the title complex is illustrated in Fig. 1. The cobalt(II) ion is coordinated octahedrally by four O atoms of water molecules and two N_pyridine atoms of isonicotinamide molecules. The values of the Co—O_water and Co—N_pyridine bond lengths and the bond angles involving atom Co1 (Table 1) are close to those reported for similar cobalt(II) complexes (Gao et al., 2006 ; Liu et al., 2012 ). The C—O bond lengths in the deprotonated carboxylic groups of the succinate dianion are almost the same, viz. 1.247 (3) Å for C7—O1 and 1.257 (3) Å for C7—O2, indicating delocalization of charge. Each O atom of the succinate dianion is linked to an H atom of a water molecule via O—H⋯O hydrogen bonds, so forming chains along the c-axis direction (Table 2 and Figs. 1 and 2).

Table 1
Selected geometric parameters (Å, °)

Co1—O3	2.1134 (15)	Co1—N2	2.1540 (16)
Co1—O4	2.0795 (16)

O4—Co1—N2ⁱ	92.15 (7)	O3—Co1—N2ⁱ	88.85 (6)
O4—Co1—N2	87.85 (6)	O4ⁱ—Co1—O3	88.82 (7)
O3—Co1—N2	91.15 (6)	O4—Co1—O3	91.18 (7)
Symmetry code: (i) -x+1, -y+1, -z+2.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O1	0.79 (4)	1.97 (4)	2.756 (3)	176 (3)
O4—H4A⋯O2	0.77 (3)	1.88 (3)	2.651 (2)	174 (3)
O3—H3A⋯O2ⁱⁱ	0.81 (3)	1.92 (3)	2.729 (2)	175 (3)
O4—H4B⋯O5ⁱⁱⁱ	0.83 (4)	1.97 (4)	2.801 (2)	174 (3)
N1—H1A⋯O5^iv	0.92 (4)	2.34 (4)	3.227 (3)	160 (3)
N1—H1B⋯O1^v	0.87 (4)	2.14 (4)	2.966 (3)	160 (3)
C5—H5⋯O2ⁱⁱ	0.93	2.41	3.307 (3)	161
C6—H6⋯O5^iv	0.93	2.31	3.223 (3)	167
Symmetry codes: (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (iii) x-1, y, z; (iv) $[-x+2, y+{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (v) x+1, y, z.

Figure 1
The molecular structure of the title complex, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. [Symmetry codes: (v) −x + 1, −y + 1, −z + 2; (vi) −x + 1, −y + 1, − z + 1.]

Figure 2
A view along the b axis of the crystal packing of the title complex. Dashed lines indicate the hydrogen bonds (see Table 2

3. Supramolecular features

In the crystal, the chains formed by O—H⋯O hydrogen bonds involving the succinate anions and the complex cations are linked by further O—H⋯O and N—H⋯O hydrogen bonds, forming a three-dimensional supramolecular architecture (Table 2 and Fig. 2). Within the framework, C—H⋯O hydrogen bonds are also present (Table 2).

4. Hirshfeld surface analysis

CrystalExplorer17.5 (Turner et al., 2017 ) was used to analyse the interactions in the crystal. The molecular Hirshfeld surfaces were obtained using a standard (high) surface resolution with the three-dimensional d_norm surfaces mapped over a fixed colour scale of −0.728 (red) to 1.428 (blue). The red spots in the d_norm surface (Fig. 3), indicate the regions of donor–acceptor interactions given in Table 2.

Figure 3
d_norm mapped on the Hirshfeld surfaces to visualize the intramolecular and intermolecular interactions of the title complex.

The view of the three-dimensional Hirshfeld surface of the title compound plotted over electrostatic potential energy in the range −0.366 to 0.236 a.u. using the STO-3G basis set at the Hartree–Fock level of theory is given in Fig. 4. The C—H⋯O, N—H⋯O and O—H⋯O hydrogen-bond donors and acceptors are shown as blue and red areas around the related atoms with positive (hydrogen-bond donors) and negative (hydrogen-bond acceptors) electrostatic potentials, respectively.

Figure 4
A view of the three-dimensional Hirshfeld surface of the title complex, plotted over the electrostatic potential energy.

The fingerprint plot for the title complex is presented in Fig. 5. The contribution from the O⋯H/H⋯O contacts, corresponding to C—H⋯O, N—H⋯O and O—H⋯O interactions, is represented by a pair of sharp spikes characteristic of a strong hydrogen-bonding interaction (43%) (Fig. 6a). The H⋯H interactions appear in the middle of the scattered points in the two-dimensional fingerprint plots with an overall Hirshfeld surface of 39.8% (Fig. 6b). The contribution of the other intermolecular contacts to the Hirshfeld surfaces is C⋯H/H⋯C (8.4%) (Fig. 6c). The C⋯C/C⋯C contacts with 3.8% contribution appear as points of low density (Fig. 6d).

Figure 5
The fingerprint plot of the title compound.

Figure 6
(a) H⋯O/O⋯H, (b) H⋯H/H⋯H, (c) H⋯C/C⋯H and (d) C⋯C/C⋯C contacts in the title complex, showing the percentages of contacts contributing to the total Hirshfeld surface area.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 5.39, update May 2018; Groom et al., 2016 ) revealed the structures of five similar tetraaquabis(isonicotinamide-κN¹)cobalt(II) complexes with different counter-anions. They include p-formylbenzoate dihydrate (HUCPIF; Hökelek et al., 2009 ), bis(3-hydroxybenzoate) tetrahydrate (LAMMOD; Zaman et al., 2012 ), disaccharinate sesquihydrate (LEHHUC; Uçar et al., 2006 ), bis(thiophene-2,5-dicarboxylate) dihydrate (NETQOU; Liu et al., 2012) and terephthalate dihydrate (SETHIJ; Gao et al., 2006). In all five complexes the cation possesses inversion symmetry with the cobalt ion being located on a centre of symmetry. The Co—O_water bond lengths vary from ca 2.057 to 2.115 Å, while the Co—Npyridine bond lengths vary from ca 2.131 to 2.169 Å. In the title complex, the cation also possesses inversion symmetry and the Co—O_water bond lengths [2.079 (2) and 2.113 (2) Å] and the Co—N_pyridine bond length [2.154 (2) Å] fall within these limits. In addition, there are several precedents for succinic acid and isonicotinamides, including the structures of bis(isonicotinamide) succinic acid (Aakeröy et al., 2002), succinic acid N,N′-octane-1,8-diyldiisonicotinamide (Aakeröy et al., 2014 ), succinic acid bis(isonicotinamide) (Vishweshwar et al., 2003) and catena-[(μ₄-succinato)(μ₂-succinato)bis(μ₂-4-pyridylisonicotinamide)dizinc] (Uebler et al., 2013 ).

6. Synthesis and crystallization

An aqueous solution of succinic acid (25 mmol, 3 g) was added to a solution of NaOH (50 mmol, 2 g) under stirring. An aqueous solution of CoCl₂·6H₂O (25 mmol, 5.95 g) was added and the reaction mixture stirred for 30 min at room temperature. The pink mixture obtained was filtered and left to dry. The pink crystalline material (0.86 mmol, 0.20 g) obtained was dissolved in water and added to a aqueous solution of isonicotinamide (1.71 mmol, 0.21 g). The resulting suspension was filtered and the filtrate allowed to stand. Red prismatic crystals were obtained from the filtrate in five weeks.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3. The water and NH₂ H 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	[Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₄O₄)
M_r	491.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6757 (8), 10.0381 (8), 11.4947 (10)
β (°)	112.489 (6)
V (Å³)	1031.53 (15)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.89
Crystal size (mm)	0.68 × 0.49 × 0.37

Data collection
Diffractometer	Stoe IPDS 2
Absorption correction	Integration (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.664, 0.770
No. of measured, independent and observed [I > 2σ(I)] reflections	5748, 2125, 1709
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.087, 1.02
No. of reflections	2125
No. of parameters	166
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.38
Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002), SHELXS97 (Sheldrick, 2008 ), SHELXL2017 (Sheldrick, 2015 ), ORTEP-3 for Windows (Farrugia, 2012 ), Mercury (Macrae et al., 2008 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1842712

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989018008861/su5446sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989018008861/su5446Isup2.hkl

checkCIF report

Computing details top

Data collection: X-AREA (Stoe & Cie, 2002); cell refinement: X-AREA (Stoe & Cie, 2002); data reduction: X-RED32 (Stoe & Cie, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2017 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2017 (Sheldrick, 2015) and PLATON (Spek, 2009).

Tetraaquabis(isonicotinamide-κN¹)cobalt(II) butanedioate top

Crystal data top

[Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₄O₄)	F(000) = 510
M_r = 491.32	D_x = 1.582 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6757 (8) Å	Cell parameters from 8789 reflections
b = 10.0381 (8) Å	θ = 3.1–30.2°
c = 11.4947 (10) Å	µ = 0.89 mm⁻¹
β = 112.489 (6)°	T = 296 K
V = 1031.53 (15) Å³	Prism, red
Z = 2	0.68 × 0.49 × 0.37 mm

Data collection top

Stoe IPDS 2 diffractometer	2125 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus	1709 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm^-1	R_int = 0.033
rotation method scans	θ_max = 26.5°, θ_min = 4.0°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)	h = −12→12
T_min = 0.664, T_max = 0.770	k = −12→12
5748 measured reflections	l = −14→10

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)] = 0.034	Hydrogen site location: mixed
wR(F²) = 0.087	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ²(F_o²) + (0.0544P)² + 0.0723P] where P = (F_o² + 2F_c²)/3
2125 reflections	(Δ/σ)_max < 0.001
166 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.38 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
Co1	0.500000	0.500000	1.000000	0.02416 (13)
O3	0.40225 (19)	0.64528 (17)	0.85930 (16)	0.0323 (3)
O4	0.39411 (19)	0.34772 (15)	0.87503 (16)	0.0314 (3)
O2	0.44508 (19)	0.36520 (15)	0.66478 (15)	0.0372 (4)
O5	1.08679 (19)	0.30825 (16)	0.80841 (18)	0.0450 (4)
O1	0.2865 (2)	0.53407 (16)	0.62211 (16)	0.0413 (4)
N2	0.68645 (19)	0.47784 (15)	0.94294 (17)	0.0284 (4)
N1	1.0405 (3)	0.5081 (3)	0.7144 (3)	0.0523 (6)
C1	1.0166 (2)	0.4142 (2)	0.7847 (2)	0.0340 (5)
C2	0.9000 (2)	0.4398 (2)	0.8388 (2)	0.0291 (4)
C5	0.7381 (2)	0.5790 (2)	0.8958 (2)	0.0336 (5)
H5	0.700517	0.663743	0.898389	0.040*
C7	0.3809 (2)	0.4648 (2)	0.6004 (2)	0.0296 (4)
C3	0.8494 (3)	0.3354 (2)	0.8895 (2)	0.0348 (5)
H3	0.886482	0.249919	0.889455	0.042*
C6	0.8434 (2)	0.5649 (2)	0.8438 (2)	0.0343 (5)
H6	0.876190	0.638596	0.812443	0.041*
C4	0.7441 (3)	0.3579 (2)	0.9399 (2)	0.0353 (5)
H4	0.711309	0.286121	0.973646	0.042*
C8	0.4207 (3)	0.5013 (3)	0.4888 (3)	0.0535 (7)
H8A	0.368960	0.440472	0.420345	0.064*
H8B	0.382876	0.590118	0.461003	0.064*
H1A	0.982 (4)	0.584 (4)	0.697 (4)	0.083 (12)*
H1B	1.107 (4)	0.495 (3)	0.683 (4)	0.076 (11)*
H4A	0.403 (3)	0.355 (3)	0.812 (3)	0.035 (7)*
H3A	0.449 (3)	0.711 (3)	0.857 (3)	0.049 (8)*
H3B	0.373 (4)	0.612 (3)	0.792 (3)	0.055 (9)*
H4B	0.304 (4)	0.330 (3)	0.858 (3)	0.065 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0267 (2)	0.02335 (19)	0.0296 (2)	−0.00065 (15)	0.01885 (15)	0.00042 (15)
O3	0.0388 (9)	0.0293 (8)	0.0331 (9)	−0.0031 (7)	0.0184 (7)	0.0019 (7)
O4	0.0343 (9)	0.0338 (8)	0.0335 (9)	−0.0035 (6)	0.0211 (7)	−0.0022 (6)
O2	0.0519 (10)	0.0311 (7)	0.0413 (9)	0.0079 (7)	0.0319 (8)	0.0046 (6)
O5	0.0432 (9)	0.0380 (9)	0.0700 (12)	−0.0002 (7)	0.0399 (9)	−0.0086 (8)
O1	0.0469 (9)	0.0431 (9)	0.0443 (10)	0.0117 (7)	0.0291 (8)	0.0043 (7)
N2	0.0296 (8)	0.0264 (9)	0.0373 (9)	−0.0010 (6)	0.0217 (7)	−0.0014 (7)
N1	0.0506 (12)	0.0602 (14)	0.0686 (15)	0.0086 (12)	0.0479 (12)	0.0121 (12)
C1	0.0285 (11)	0.0403 (12)	0.0406 (12)	−0.0040 (9)	0.0214 (10)	−0.0073 (9)
C2	0.0257 (10)	0.0333 (10)	0.0336 (11)	−0.0011 (8)	0.0174 (9)	−0.0032 (8)
C5	0.0368 (12)	0.0252 (10)	0.0475 (13)	0.0038 (8)	0.0260 (10)	0.0045 (9)
C7	0.0323 (10)	0.0304 (10)	0.0309 (11)	−0.0036 (8)	0.0175 (9)	−0.0010 (8)
C3	0.0368 (12)	0.0258 (10)	0.0515 (13)	−0.0003 (8)	0.0276 (10)	−0.0027 (9)
C6	0.0349 (11)	0.0320 (11)	0.0450 (13)	0.0004 (9)	0.0253 (10)	0.0076 (9)
C4	0.0400 (12)	0.0262 (10)	0.0516 (14)	−0.0018 (9)	0.0307 (11)	0.0014 (9)
C8	0.0439 (14)	0.0825 (19)	0.0455 (14)	0.0135 (14)	0.0298 (12)	0.0250 (14)

Geometric parameters (Å, º) top

Co1—O4ⁱ	2.0794 (16)	N1—H1A	0.92 (4)
Co1—O3	2.1134 (15)	N1—H1B	0.87 (4)
Co1—O4	2.0795 (16)	C1—C2	1.504 (3)
Co1—N2ⁱ	2.1540 (16)	C2—C3	1.377 (3)
Co1—O3ⁱ	2.1134 (15)	C2—C6	1.381 (3)
Co1—N2	2.1540 (16)	C5—C6	1.372 (3)
O3—H3A	0.81 (3)	C5—H5	0.9300
O3—H3B	0.79 (4)	C7—C8	1.519 (3)
O4—H4A	0.77 (3)	C3—C4	1.370 (3)
O4—H4B	0.83 (4)	C3—H3	0.9300
O2—C7	1.257 (3)	C6—H6	0.9300
O5—C1	1.235 (3)	C4—H4	0.9300
O1—C7	1.247 (3)	C8—C8ⁱⁱ	1.456 (5)
N2—C4	1.333 (3)	C8—H8A	0.9700
N2—C5	1.334 (3)	C8—H8B	0.9700
N1—C1	1.317 (3)

O3—Co1—O3ⁱ	180	O5—C1—N1	122.8 (2)
O4ⁱ—Co1—O4	180	O5—C1—C2	119.4 (2)
N2ⁱ—Co1—N2	180	N1—C1—C2	117.8 (2)
O4ⁱ—Co1—O3	88.82 (7)	C3—C2—C6	117.62 (18)
O4—Co1—O3	91.18 (7)	C3—C2—C1	119.32 (18)
O4ⁱ—Co1—O3ⁱ	91.18 (7)	C6—C2—C1	123.03 (19)
O4—Co1—O3ⁱ	88.82 (7)	N2—C5—C6	123.66 (19)
O4ⁱ—Co1—N2ⁱ	87.85 (6)	N2—C5—H5	118.2
O4—Co1—N2ⁱ	92.15 (7)	C6—C5—H5	118.2
O3—Co1—N2ⁱ	88.85 (6)	O1—C7—O2	124.09 (19)
O3ⁱ—Co1—N2ⁱ	91.15 (6)	O1—C7—C8	118.4 (2)
O4ⁱ—Co1—N2	92.15 (7)	O2—C7—C8	117.47 (19)
O4—Co1—N2	87.85 (6)	C4—C3—C2	119.73 (19)
O3—Co1—N2	91.15 (6)	C4—C3—H3	120.1
O3ⁱ—Co1—N2	88.85 (6)	C2—C3—H3	120.1
Co1—O3—H3A	120 (2)	C5—C6—C2	118.99 (19)
Co1—O3—H3B	110 (2)	C5—C6—H6	120.5
H3A—O3—H3B	108 (3)	C2—C6—H6	120.5
Co1—O4—H4A	112 (2)	N2—C4—C3	123.14 (19)
Co1—O4—H4B	121 (2)	N2—C4—H4	118.4
H4A—O4—H4B	106 (3)	C3—C4—H4	118.4
C4—N2—C5	116.83 (17)	C8ⁱⁱ—C8—C7	115.9 (3)
C4—N2—Co1	120.60 (13)	C8ⁱⁱ—C8—H8A	108.3
C5—N2—Co1	122.14 (13)	C7—C8—H8A	108.3
C1—N1—H1A	119 (3)	C8ⁱⁱ—C8—H8B	108.3
C1—N1—H1B	119 (2)	C7—C8—H8B	108.3
H1A—N1—H1B	122 (3)	H8A—C8—H8B	107.4

O5—C1—C2—C3	−14.5 (3)	N2—C5—C6—C2	0.2 (4)
N1—C1—C2—C3	166.3 (2)	C3—C2—C6—C5	−1.4 (3)
O5—C1—C2—C6	163.5 (2)	C1—C2—C6—C5	−179.5 (2)
N1—C1—C2—C6	−15.7 (3)	C5—N2—C4—C3	−1.2 (4)
C4—N2—C5—C6	1.1 (4)	Co1—N2—C4—C3	171.39 (19)
Co1—N2—C5—C6	−171.37 (19)	C2—C3—C4—N2	0.0 (4)
C6—C2—C3—C4	1.4 (4)	O1—C7—C8—C8ⁱⁱ	136.1 (3)
C1—C2—C3—C4	179.5 (2)	O2—C7—C8—C8ⁱⁱ	−44.5 (5)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O1	0.79 (4)	1.97 (4)	2.756 (3)	176 (3)
O4—H4A···O2	0.77 (3)	1.88 (3)	2.651 (2)	174 (3)
O3—H3A···O2ⁱⁱⁱ	0.81 (3)	1.92 (3)	2.729 (2)	175 (3)
O4—H4B···O5^iv	0.83 (4)	1.97 (4)	2.801 (2)	174 (3)
N1—H1A···O5^v	0.92 (4)	2.34 (4)	3.227 (3)	160 (3)
N1—H1B···O1^vi	0.87 (4)	2.14 (4)	2.966 (3)	160 (3)
C5—H5···O2ⁱⁱⁱ	0.93	2.41	3.307 (3)	161
C6—H6···O5^v	0.93	2.31	3.223 (3)	167

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

References

Aakeröy, C. B., Beatty, A. M. & Helfrich, B. A. (2002). J. Am. Chem. Soc. 124, 14425–14432. Web of Science PubMed Google Scholar
Aakeröy, C. B., Forbes, S. & Desper, J. (2014). CrystEngComm, 16, 5870–5877. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Gao, G.-G., Liu, B., Li, C.-B. & Che, G.-B. (2006). Acta Cryst. E62, m3357–m3358. Web of Science CSD CrossRef IUCr Journals Google Scholar
Groom, C. R., Bruno, I. J., Lightfoot, M. P. & Ward, S. C. (2016). Acta Cryst. B72, 171–179. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hökelek, T., Yılmaz, F., Tercan, B., Sertçelik, M. & Necefoğlu, H. (2009). Acta Cryst. E65, m1130–m1131. Web of Science CSD CrossRef IUCr Journals Google Scholar
Liu, B., Li, X.-M., Zhou, S., Wang, Q.-W. & Li, C.-B. (2012). Chin. J. Inorg. Chem. 28, 1019–1026. 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2015). Acta Cryst. A71, 3–8. Web of Science CrossRef IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stoe & Cie (2002). X-AREA and X-RED32. Stoe & Cie GmbH, Darmstadt, Germany. Google Scholar
Turner, M. J., MacKinnon, J. J., Wolff, S. K., Grimwood, D. J., Spackman, P. R., Jayatilaka, D. & Spackman, M. A. (2017). Crystal Explorer17.5. University of Western Australia. Google Scholar
Uçar, İ., Karabulut, B., Paşaoğlu, H., Büyükgüngör, O. & Bulut, A. (2006). J. Mol. Struct. 787, 38–44. Google Scholar
Uebler, J. W., Wilson, J. A. & LaDuca, R. L. (2013). CrystEngComm, 15, 1586–1596. Web of Science CSD CrossRef CAS Google Scholar
Vishweshwar, P., Nangia, A. & Lynch, V. M. (2003). CrystEngComm, 3, 783–790. Google Scholar
Zaman, İ. G., Çaylak Delibaş, N., Necefoğlu, H. & Hökelek, T. (2012). Acta Cryst. E68, m249–m250. CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.