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

Kansiz, S.; Almarhoon, Z.M.; Dege, N.

doi:10.1107/S205698901800107X

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ISSN: 2056-9890

Volume 74| Part 2| February 2018| Pages 217-220

https://doi.org/10.1107/S205698901800107X

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

Sevgi Kansiz,^a ^* Zainab M Almarhoon ^b and Necmi Dege ^a

^aOndokuz Mayıs University, Faculty of Arts and Sciences, Department of Physics, 55139, Samsun, Turkey, and ^bKing Saud University, Faculty of Science, Department of Chemistry, Riyadh, Saudi Arabia
^*Correspondence e-mail: sevgi.koroglu@omu.edu.tr

Edited by D.-J. Xu, Zhejiang University (Yuquan Campus), China (Received 7 January 2018; accepted 17 January 2018; online 26 January 2018)

The reaction of cobalt(II) with fumaric acid (H₂fum) and isonicotinamide in a basic solution produces the title salt, [Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄). In the complex cation, the Co^II atom, located on an inversion centre, is coordinated by two isonicotinamide and four water molecules in a distorted N₂O₄ octahedral geometry. The fumarate anion is located on another inversion centre and is linked to neighbouring complex cations via O—H⋯O and N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds. In the crystal, the complex cations are further linked by O—H⋯O, N—H⋯O and weak C—H⋯O hydrogen bonds, forming a three-dimensional supramolecular architectecture. Hirshfeld surface analyses (d_norm surfaces and two-dimensional fingerprint plots) for the title compound are presented and discussed.

Keywords: crystal structure; fumaric acid; isonicotinamide; cobalt(II); Hirshfeld surfaces.

CCDC reference: 1561543

1. Chemical context

Metal carboxylates have attracted intense attention because of their interesting framework topologies (Rao et al., 2004 ). Among metal carboxylates, fumarate dianions (fum) have good conformational freedom and they possess some desirable features such as being versatile ligands because of the four electron-donor oxygen atoms they carry, and their ability to link inorganic moieties (Zheng et al., 2003 ). Moreover, metal fumarates exhibit interesting structural varieties.

Dicarboxylic acids such as fumaric acid and amides have been particularly useful in creating many supramolecular structures involving isonicotinamide and a variety of carboxylic acid molecules (Vishweshwar et al., 2003 ; Aakeröy et al., 2002 ). Dicarboxylic acid ligands are utilized in the synthesis of a wide variety of metal carboxylates. For this reason they have been investigated extensively, both experimentally and computationally. We describe herein the synthesis, structural features and Hirshfeld surface analysis of the title salt.

2. Structural commentary

The molecular structure of the title compound is illustrated in Fig. 1. The Co^II cation and midpoint of the C=C bond of the fumarate anion are each located on an inversion centre. In the complex cation, the Co^II atom is coordinated to two isonicotinamide ligands and four water molecules in a distorted N₂O₄ octahedral geometry. The fumarate anion interacts with neighboring complex cations via O—H⋯O and N—H⋯O hydrogen bonds and weak C—H⋯O hydrogen bonds (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯O5ⁱ	0.86	1.96	2.814 (2)	171
O2—H2B⋯O4ⁱⁱ	0.86	1.88	2.7165 (19)	165
O3—H3A⋯O1ⁱⁱⁱ	0.86	1.95	2.792 (2)	168
O3—H3B⋯O4	0.86	1.82	2.6652 (19)	172
N2—H2C⋯O5^iv	0.86	2.13	2.955 (2)	160
N2—H2D⋯O1^v	0.86	2.47	3.288 (3)	159
C1—H1⋯O4^vi	0.93	2.41	3.322 (2)	168
C2—H2⋯O1^v	0.93	2.30	3.225 (3)	173
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (iii) x+1, y, z; (iv) x-1, y, z; (v) $[-x, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ ; (vi) $[-x+1, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Figure 1
The molecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 50% probability level. [Symmetry codes: (i) –x + 1, −y + 1, −z + 1; (vii) –x + 1, −y + 1, −z + 2.]

3. Supramolecular features

In the crystal, the fumarate anions and complex cations are linked by O—H⋯O, N—H⋯O and C—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 (Table 1, Fig. 2).

Figure 2
Packing of the title compound in the unit cell. Dashed lines indicate hydrogen bonds.

4. Hirshfeld surface analysis

Crystal Explorer 17.5 (Turner et al., 2017 ) was used to analyse the interactions in the crystal and fingerprint plots mapped over d_norm (Figs. 3 and 4) were generated. The contact distances to the closest atom inside (d_i) and outside (d_e) of the Hirshfeld surface are used to analyse the intermolecular interactions via the mapping of d_norm. 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 −1.227 (red) to 1.279 (blue). Many studies on Hirshfeld surfaces can be found in the literature (see, for example, Şen et al., 2018 ; Yaman et al., 2018 ).

Figure 3
The Hirshfeld surface of the title compound mapped with d_norm. The red spots indicate the regions of the donor–acceptor interactions.

Figure 4
d_norm mapped on the Hirshfeld surfaces for the title structure.

In a d_norm surface, any intermolecular interactions will appear as red spots. The red spots indicate the regions of donor–acceptor interactions. There are many red spots in the d_norm surface (Fig. 3), which are usually on the O-acceptor atoms involved in the interactions listed in Table 1. Strong hydrogen-bond interactions, such as O—H⋯O, are seen as a bright-red areas on the Hirshfeld surfaces (Şen et al., 2017 ).

The fingerprint plot for the title complex is presented in Fig. 5. The H⋯H interactions appear in the middle of the scattered points in the two-dimensional fingerprint plots with an overall contribution to the Hirshfeld surface of 35.5% (Fig. 6b). 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-bond interaction (35.9%) (Fig. 6a). The C⋯C/C⋯C contacts have a sharp spike between the O⋯H and H⋯O spikes (5.7%) (Fig. 6d). The contribution of the other intermolecular contacts to the Hirshfeld surfaces is C⋯H/H⋯C (10.3%) (Fig. 6c).

Figure 5
A fingerprint plot of the title complex.

Figure 6
(a) O⋯H/H⋯O, (b) H⋯H/H⋯H, (c) C⋯H/H⋯C 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 for fumaric acid and isonicotinamide revealed the presence of seven structures: isonicotinohyrazide nicotinamide fumaric acid (Aitipamula et al., 2013 ), catena-poly[[aquabis[N-(pyridin-3-yl)isonicotinamide-κN¹)copper(II)]-(μ₂-fumarato-κO,O′)-(Qiblawi & LaDuca, 2012 ), bis(isonicotinamide) fumaric acid (Aakeröy et al., 2002), catena-[bis(μ₂-fumarato)bis(μ₂-3-pyridylisonicotinamide)dizinctrihydrate] (Uebler et al., 2013 ) and catena-[bis(μ-but-2-enedioato)bis(μ-pyridine-4-carbohydrazide)dizinc(II)] (Naskar et al., 2017 ). In these compounds, the C—H⋯O hydrogen bonds have H⋯O distances ranging from 2.56 to 3.59 Å and C⋯O distances ranging from 3.27 to 3.96 Å. The N—H⋯O hydrogen bonds have H⋯O distances ranging from 1.86 to 2.33 Å and N⋯O distances ranging from 2.82 to 3.15 Å.

6. Synthesis and crystallization

An aqueous solution of fumaric acid (26 mmol, 3 g) in water was added to a solution of NaOH (52 mmol, 2.07 g) while stirring. A solution of CoCl₂·6H₂O (25 mmol, 6.19 g) in water was added. The reaction mixture was stirred for an hour at room temperature. The pink mixture was filtered and left to dry. The pink crystals (0.88 mmol, 0.20 g) were dissolved in water and added to an aqueous solution of isonicotinamide (1.75 mmol, 0.21 g). The resulting suspension was filtered and allowed to crystallize for five weeks at room temperature yielding orange block-shaped crystals suitable for X-ray diffraction analysis.

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The N-bound and C-bound hydrogen atoms were positioned geometrically and treated as riding: N—H = 0.86 Å and C—H = 0.93 Å with U_iso(H) = 1.2U_eq(C,N). Water H atoms were found in a difference-Fourier map, restrained with O—H = 0.85 Å and refined with U_iso(H) = 1.5U_eq(O).

Table 2
Experimental details

Crystal data
Chemical formula	[Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄)
M_r	489.30
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	296
a, b, c (Å)	9.6914 (10), 10.0106 (11), 11.3811 (12)
β (°)	113.416 (3)
V (Å³)	1013.22 (19)
Z	2
Radiation type	Mo Kα
μ (mm⁻¹)	0.91
Crystal size (mm)	0.25 × 0.19 × 0.16

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Analytical (X-RED32; Stoe & Cie, 2002 )
T_min, T_max	0.394, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	19963, 1962, 1830
R_int	0.032
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.077, 1.14
No. of reflections	1962
No. of parameters	144
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.35, −0.35
Computer programs: APEX2 and SAINT (Bruker, 2007 ), SHELXT2014 (Sheldrick, 2015a ), SHELXL2016 (Sheldrick, 2015b ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1561543

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S205698901800107X/xu5915sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S205698901800107X/xu5915Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXT2014 (Sheldrick, 2015a); program(s) used to refine structure: SHELXL2016 (Sheldrick, 2015b); 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)cobalt(II) fumarate top

Crystal data top

[Co(C₆H₆N₂O)₂(H₂O)₄](C₄H₂O₄)	F(000) = 506
M_r = 489.30	D_x = 1.604 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.6914 (10) Å	Cell parameters from 9553 reflections
b = 10.0106 (11) Å	θ = 3.1–28.3°
c = 11.3811 (12) Å	µ = 0.91 mm⁻¹
β = 113.416 (3)°	T = 296 K
V = 1013.22 (19) Å³	Block, orange
Z = 2	0.25 × 0.19 × 0.16 mm

Data collection top

Bruker APEXII CCD diffractometer	1830 reflections with I > 2σ(I)
φ and ω scans	R_int = 0.032
Absorption correction: analytical (X-RED32; Stoe & Cie, 2002)	θ_max = 26.0°, θ_min = 3.1°
T_min = 0.394, T_max = 0.746	h = −11→11
19963 measured reflections	k = −12→12
1962 independent reflections	l = −14→13

Refinement top

Refinement on F²	0 restraints
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.032	H-atom parameters constrained
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0211P)² + 1.1735P] where P = (F_o² + 2F_c²)/3
S = 1.14	(Δ/σ)_max < 0.001
1962 reflections	Δρ_max = 0.35 e Å⁻³
144 parameters	Δρ_min = −0.35 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	0.500000	0.01658 (12)
O3	0.60307 (15)	0.65750 (13)	0.62150 (13)	0.0237 (3)
H3A	0.696404	0.660264	0.635017	0.035*
H3B	0.594575	0.646860	0.692916	0.035*
O2	0.39661 (15)	0.64187 (13)	0.35319 (13)	0.0240 (3)
H2A	0.368923	0.604165	0.279836	0.036*
H2B	0.458953	0.704445	0.358200	0.036*
O4	0.55105 (17)	0.63859 (14)	0.83392 (14)	0.0283 (3)
O1	−0.09235 (17)	0.70328 (16)	0.68073 (17)	0.0365 (4)
O5	0.72605 (18)	0.48025 (16)	0.88934 (16)	0.0356 (4)
N1	0.31337 (18)	0.52596 (16)	0.55744 (16)	0.0208 (3)
C7	0.6189 (2)	0.54056 (19)	0.90123 (18)	0.0221 (4)
C3	0.1007 (2)	0.5713 (2)	0.66124 (18)	0.0216 (4)
C8	0.5656 (2)	0.48648 (19)	0.99864 (19)	0.0239 (4)
H8	0.629871	0.429951	1.061428	0.029*
N2	−0.0347 (3)	0.5112 (2)	0.7922 (2)	0.0491 (6)
H2C	−0.102155	0.523521	0.822413	0.059*
H2D	0.020826	0.440936	0.812861	0.059*
C4	0.1453 (2)	0.6727 (2)	0.6015 (2)	0.0268 (4)
H4	0.103978	0.757665	0.594549	0.032*
C2	0.1627 (2)	0.4464 (2)	0.6655 (2)	0.0297 (5)
H2	0.134441	0.375248	0.703564	0.036*
C6	−0.0163 (2)	0.6003 (2)	0.7141 (2)	0.0279 (4)
C5	0.2516 (2)	0.64642 (19)	0.5523 (2)	0.0263 (4)
H5	0.281757	0.715892	0.513627	0.032*
C1	0.2671 (2)	0.4283 (2)	0.6126 (2)	0.0275 (4)
H1	0.307396	0.343382	0.615691	0.033*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01724 (19)	0.01624 (19)	0.0214 (2)	−0.00028 (12)	0.01310 (14)	0.00056 (13)
O3	0.0239 (7)	0.0251 (7)	0.0276 (7)	−0.0036 (6)	0.0162 (6)	−0.0033 (6)
O2	0.0259 (7)	0.0220 (7)	0.0258 (7)	−0.0015 (5)	0.0121 (6)	0.0031 (5)
O4	0.0421 (8)	0.0219 (7)	0.0319 (7)	0.0059 (6)	0.0264 (7)	0.0046 (6)
O1	0.0332 (8)	0.0303 (8)	0.0602 (11)	−0.0001 (7)	0.0334 (8)	−0.0075 (7)
O5	0.0354 (8)	0.0430 (9)	0.0409 (9)	0.0129 (7)	0.0284 (7)	0.0091 (7)
N1	0.0207 (8)	0.0199 (8)	0.0274 (8)	−0.0003 (6)	0.0154 (7)	−0.0003 (6)
C7	0.0262 (9)	0.0217 (9)	0.0234 (9)	−0.0018 (8)	0.0151 (8)	−0.0023 (8)
C3	0.0178 (9)	0.0268 (10)	0.0247 (9)	−0.0017 (7)	0.0134 (7)	−0.0023 (8)
C8	0.0282 (10)	0.0240 (10)	0.0243 (10)	0.0033 (8)	0.0155 (8)	0.0037 (7)
N2	0.0411 (12)	0.0675 (15)	0.0591 (14)	0.0163 (11)	0.0416 (11)	0.0225 (11)
C4	0.0285 (10)	0.0182 (9)	0.0425 (12)	0.0012 (8)	0.0234 (9)	−0.0016 (8)
C2	0.0303 (10)	0.0270 (10)	0.0428 (12)	0.0024 (9)	0.0261 (10)	0.0110 (9)
C6	0.0208 (9)	0.0359 (12)	0.0330 (11)	−0.0056 (9)	0.0170 (8)	−0.0089 (9)
C5	0.0300 (10)	0.0191 (9)	0.0397 (11)	−0.0005 (8)	0.0245 (9)	0.0032 (8)
C1	0.0274 (10)	0.0204 (10)	0.0432 (12)	0.0039 (8)	0.0229 (9)	0.0058 (8)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.0731 (13)	C7—C8	1.498 (3)
Co1—O3	2.0731 (13)	C3—C2	1.380 (3)
Co1—O2ⁱ	2.1171 (13)	C3—C4	1.383 (3)
Co1—O2	2.1171 (13)	C3—C6	1.509 (3)
Co1—N1	2.1694 (16)	C8—C8ⁱⁱ	1.313 (4)
Co1—N1ⁱ	2.1694 (16)	C8—H8	0.9300
O3—H3A	0.8556	N2—C6	1.320 (3)
O3—H3B	0.8555	N2—H2C	0.8600
O2—H2A	0.8564	N2—H2D	0.8600
O2—H2B	0.8564	C4—C5	1.380 (3)
O4—C7	1.258 (2)	C4—H4	0.9300
O1—C6	1.236 (3)	C2—C1	1.379 (3)
O5—C7	1.254 (2)	C2—H2	0.9300
N1—C1	1.332 (3)	C5—H5	0.9300
N1—C5	1.337 (2)	C1—H1	0.9300

O3ⁱ—Co1—O3	180.0	O4—C7—C8	118.86 (17)
O3ⁱ—Co1—O2ⁱ	88.15 (6)	C2—C3—C4	117.75 (17)
O3—Co1—O2ⁱ	91.85 (6)	C2—C3—C6	123.14 (18)
O3ⁱ—Co1—O2	91.85 (6)	C4—C3—C6	119.07 (18)
O3—Co1—O2	88.15 (6)	C8ⁱⁱ—C8—C7	124.4 (2)
O2ⁱ—Co1—O2	180.0	C8ⁱⁱ—C8—H8	117.8
O3ⁱ—Co1—N1	93.08 (6)	C7—C8—H8	117.8
O3—Co1—N1	86.92 (6)	C6—N2—H2C	120.0
O2ⁱ—Co1—N1	91.85 (6)	C6—N2—H2D	120.0
O2—Co1—N1	88.15 (6)	H2C—N2—H2D	120.0
O3ⁱ—Co1—N1ⁱ	86.92 (6)	C5—C4—C3	119.29 (18)
O3—Co1—N1ⁱ	93.08 (6)	C5—C4—H4	120.4
O2ⁱ—Co1—N1ⁱ	88.14 (6)	C3—C4—H4	120.4
O2—Co1—N1ⁱ	91.85 (6)	C1—C2—C3	119.26 (18)
N1—Co1—N1ⁱ	180.0	C1—C2—H2	120.4
Co1—O3—H3A	109.8	C3—C2—H2	120.4
Co1—O3—H3B	109.6	O1—C6—N2	123.2 (2)
H3A—O3—H3B	109.1	O1—C6—C3	119.28 (19)
Co1—O2—H2A	109.9	N2—C6—C3	117.5 (2)
Co1—O2—H2B	109.8	N1—C5—C4	123.21 (18)
H2A—O2—H2B	109.1	N1—C5—H5	118.4
C1—N1—C5	117.00 (16)	C4—C5—H5	118.4
C1—N1—Co1	122.07 (13)	N1—C1—C2	123.47 (19)
C5—N1—Co1	120.48 (13)	N1—C1—H1	118.3
O5—C7—O4	124.37 (18)	C2—C1—H1	118.3
O5—C7—C8	116.71 (18)

O5—C7—C8—C8ⁱⁱ	−161.6 (3)	C2—C3—C6—N2	15.6 (3)
O4—C7—C8—C8ⁱⁱ	15.7 (4)	C4—C3—C6—N2	−166.7 (2)
C2—C3—C4—C5	−1.8 (3)	C1—N1—C5—C4	0.4 (3)
C6—C3—C4—C5	−179.59 (19)	Co1—N1—C5—C4	−172.01 (17)
C4—C3—C2—C1	1.1 (3)	C3—C4—C5—N1	1.1 (3)
C6—C3—C2—C1	178.8 (2)	C5—N1—C1—C2	−1.2 (3)
C2—C3—C6—O1	−162.7 (2)	Co1—N1—C1—C2	171.10 (17)
C4—C3—C6—O1	14.9 (3)	C3—C2—C1—N1	0.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···O5ⁱ	0.86	1.96	2.814 (2)	171
O2—H2B···O4ⁱⁱⁱ	0.86	1.88	2.7165 (19)	165
O3—H3A···O1^iv	0.86	1.95	2.792 (2)	168
O3—H3B···O4	0.86	1.82	2.6652 (19)	172
N2—H2C···O5^v	0.86	2.13	2.955 (2)	160
N2—H2D···O1^vi	0.86	2.47	3.288 (3)	159
C1—H1···O4^vii	0.93	2.41	3.322 (2)	168
C2—H2···O1^vi	0.93	2.30	3.225 (3)	173

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

Funding information

This research project was supported by a grant from the `Research Center of the Female Scientific and Medical Colleges', Deanship of Scientific Research, King Saud University.

References

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