Crystal structure of trans-di­aqua­bis­(4-cyano­benzoato-κO)bis­(N,N-di­ethyl­nicotinamide-κN)cadmium

Akduran, N.; Sertçelik, M.; Aydoğdu, Ö.; Necefoğlu, H.; Hökelek, T.

doi:10.1107/S2056989016018247

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ISSN: 2056-9890

Volume 72| Part 12| December 2016| Pages 1827-1829

https://doi.org/10.1107/S2056989016018247

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Crystal structure of trans-diaquabis(4-cyanobenzoato-κO)bis(N,N-diethylnicotinamide-κN)cadmium

Nurcan Akduran,^a Mustafa Sertçelik,^b Ömer Aydoğdu,^c Hacali Necefoğlu ^c,^d and Tuncer Hökelek ^e ^*

^aSANAEM, Saray Mahallesi, Atom Caddesi, No:27, 06980 Saray-Kazan, Ankara, Turkey, ^bDepartment of Chemical Engineering, Kafkas University, 36100 Kars, Turkey, ^cDepartment of Chemistry, Kafkas University, 36100 Kars, Turkey, ^dInternational Scientific Research Centre, Baku State University, 1148 Baku, Azerbaijan, and ^eDepartment of Physics, Hacettepe University, 06800 Beytepe, Ankara, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

Edited by M. Weil, Vienna University of Technology, Austria (Received 8 November 2016; accepted 14 November 2016; online 18 November 2016)

The mononuclear title cadmium complex, [Cd(C₁₀H₁₄N₂O)₂(C₈H₄NO₂)₂(H₂O)₂], is centrosymmetric and contains two water molecules, two 4-cyanobenzoate (CB) ligands and two diethylnicotinamide (DENA) ligands. All the ligands are coordinated to the Cd^II atom in a monodentate mode. The four nearest O atoms around the Cd^II atom form a slightly distorted square-planar arrangement, with the distorted octahedral coordination sphere being completed by the two pyridine N atoms of the DENA ligands at distances of 2.3336 (13) Å. The dihedral angle between the carboxylate group and the adjacent benzene ring is 8.75 (16)°, while the benzene and pyridine rings are oriented at a dihedral angle of 57.83 (5)°. The water molecules exhibit both intramolecular [to the non-coordinating carboxylate O atom, enclosing an S(6) hydrogen-bonding motif, where O⋯O = 2.670 (2) Å] and intermolecular [to the amide carbonyl O atom, enclosing an R₂²(16) ring motif, where O⋯O = 2.781 (2) Å] O—H⋯O hydrogen bonds. The latter lead to the formation of supramolecular chains propagating along [110].

Keywords: crystal structure; cadmium; transition metal complexes of benzoic acid and nicotinamide derivatives.

CCDC reference: 1517222

1. Chemical context

Nicotinamide (NA) is one form of niacin. A deficiency of this vitamin leads to loss of copper from the body, known as pellagra disease. Pellagra patients show unusually high serum and urinary copper levels (Krishnamachari, 1974 ). The nicotinic acid derivative N,N′-diethylnicotinamide (DENA) is an important respiratory stimulant (Bigoli et al., 1972 ). The crystal structures of some complexes obtained from the reactions of transition metal(II) ions with NA or DENA as ligands, e.g. [Ni(NA)₂(C₇H₄ClO₂)₂(H₂O)₂] (Hökelek et al., 2009a ) and [Ni(DENA)₂(C₇H₄ClO₂)₂(H₂O)₂] (Hökelek et al., 2009b ), have been determined in our laboratory.

The structure–function–coordination relationships of the arylcarboxylate ion in Cd^II complexes of benzoic acid derivatives may change depending on the nature and position of the substituent groups on the benzene ring, the nature of the additional ligand molecule or solvent, and the pH and temperature of synthesis (Shnulin et al., 1981 ; Nadzhafov et al., 1981 ; Antsyshkina et al., 1980 ; Adiwidjaja et al., 1978 ). When pyridine and its derivatives are used instead of water molecules, the structure is completely different (Catterick et al., 1974 ). In this context, we synthesized a Cd^II-containing compound with 4-cyanobenzoate (CB) and DENA ligands, namely trans-diaquabis(4-cyanobenzoato-κO)bis(N,N′-diethylnicotinamide-κN)cadmium, [Cd(CB)₂(DENA)₂(H₂O)₂], and report herein its crystal structure.

2. Structural commentary

The asymmetric unit of the mononuclear title complex contains one Cd^II atom located on an inversion centre, one CB ligand, one DENA ligand as well as one water molecule, all ligands coordinating to the Cd^II atom in a monodentate mode (Fig. 1).

Figure 1
The molecular structure of the title complex with the atom-numbering scheme for the asymmetric unit. Unlabelled atoms are generated by symmetry operation (−x, −y, −z). Displacement ellipsoids are drawn at the 50% probability level. Intramolecular O—H_w⋯O_c (w = water, c = non-coordinating carboxylate O atom) hydrogen bonds, enclosing S(6) hydrogen-bonding motifs, are shown as dashed lines.

The two carboxylate O atoms (O2 and O2ⁱ) [symmetry code: (i) −x, −y, −z] of the two symmetry-related monodentate CB anions and water O atoms (O4 and O4ⁱ) form a slightly distorted square-planar arrangement around the Cd1 atom, while the slightly distorted octahedral coordination sphere is completed by the two pyridine N atoms (N1 and N1ⁱ) of two DENA ligands (Fig. 1). The Cd—O bond lengths involving the water O atoms [2.3192 (14) Å] are ca 0.06 Å longer than those involving the benzoate oxygen atoms [2.2588 (12) Å]; the Cd—N bond length is the longest with 2.3336 (13) Å in the CdO₄N₂ octahedron. The Cd1 atom lies 0.7558 (1) Å below the planar (O1/O2/C1) carboxylate group. The O—Cd—O and O—Cd—N bond angles range from 87.54 (5) to 92.46 (5)°. In the carboxylate groups, the C—O bonds of the coordinating O atoms [C1—O1 = 1.244 (2) Å and C1—O2 = 1.259 (2) Å] are 0.015 (2) Å longer than those of the non-coordinating ones, indicating delocalized bonding arrangements rather than localized single and double bonds. The dihedral angle between the carboxylate group (O1/O2/C1) and the adjacent benzene (C2–C7) ring is 8.75 (16)°, while the benzene and pyridine (N1/C9–C13) rings are oriented at a dihedral angle of 57.83 (5)°.

3. Supramolecular features

Intramolecular O—H_w⋯O_c (w = water, c = non-coordinating carboxylate O atom) hydrogen bonds (Table 1) link the water molecules by one of their H atoms to the CB anions, enclosing S(6) hydrogen-bonding motifs (Fig. 1). The other water H atom is involved in intermolecular O—H_w⋯O_DENA (O_DENA = carbonyl O atom of N,N′-diethylnicotinamide) hydrogen bonds (Table 1), enclosing R₂²(16) ring motifs, leading to the formation of infinite chains (Fig. 2) propagating along the [110] direction (Fig. 3).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O3ⁱ	0.78 (3)	2.01 (3)	2.781 (2)	169 (3)
O4—H42⋯O1ⁱⁱ	0.87 (3)	1.84 (3)	2.670 (2)	159 (3)
Symmetry codes: (i) x+1, y-1, z; (ii) -x, -y, -z.

Figure 2
Part of the supramolecular chain of the title compound. Intermolecular O—H_w ⋯ O_DENA (O_DENA = carbonyl O atom of N,N′-diethylnicotinamide) hydrogen bonds, enclosing R₂²(16) ring motifs, are shown as dashed lines. Non-bonding H atoms have been omitted for clarity.

Figure 3
Part of the crystal structure. Intra- and intermolecular [O–H_w ⋯ O_c and O—H_w ⋯ O_DENA, respectively] hydrogen bonds are shown as dashed lines (see Table 1

). Non-bonding H atoms have been omitted for clarity.

4. Synthesis and crystallization

The title compound was prepared by the reaction of CdSO₄·8/3H₂O (0.64 g, 2.5 mmol) in H₂O (50 ml) and diethylnicotinamide (0.89 g, 5 mmol) in H₂O (10 ml) with sodium 4-cyanobenzoate (0.85 g, 5 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for several days, giving colourless single crystals.

5. Refinement

Experimental details including the crystal data, data collection and refinement are summarized in Table 2. Atoms H41 and H42 (for H₂O) were located in a difference Fourier map and were refined freely. The C-bound H atoms were positioned geometrically with C—H = 0.93, 0.97 and 0.96 Å, for aromatic, methylene and methyl H atoms, respectively, and constrained to ride on their parent atoms, with U_iso(H) = k × U_eq(C), where k = 1.5 for methyl H atoms and k = 1.2 for aromatic and methylene H-atoms.

Table 2
Experimental details

Crystal data
Chemical formula	[Cd(C₁₀H₁₄N₂O)₂(C₈H₄NO₂)₂(H₂O)₂]
M_r	797.16
Crystal system, space group	Triclinic, P $[\overline{1}]$
Temperature (K)	296
a, b, c (Å)	7.5125 (2), 8.6671 (3), 15.3079 (5)
α, β, γ (°)	86.198 (3), 76.249 (4), 74.730 (3)
V (Å³)	933.97 (5)
Z	1
Radiation type	Mo Kα
μ (mm⁻¹)	0.64
Crystal size (mm)	0.15 × 0.11 × 0.10

Data collection
Diffractometer	Bruker APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2012 )
T_min, T_max	0.595, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections	46611, 4638, 4538
R_int	0.044
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.027, 0.068, 1.09
No. of reflections	4638
No. of parameters	243
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.42, −1.02
Computer programs: APEX2 and SAINT (Bruker, 2012), SHELXS97 and SHELXL97 (Sheldrick, 2008 ), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ) and PLATON (Spek, 2009 ).

Supporting information

CCDC reference: 1517222

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S2056989016018247/wm5339sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016018247/wm5339Isup2.hkl

checkCIF report

Computing details top

Data collection: APEX2 (Bruker, 2012); cell refinement: SAINT (Bruker, 2012); data reduction: SAINT (Bruker, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

trans-Diaquabis(4-cyanobenzoato-κO)bis(N,N-diethylnicotinamide-κN)cadmium top

Crystal data top

[Cd(C₁₀H₁₄N₂O)₂(C₈H₄NO₂)₂(H₂O)₂]	Z = 1
M_r = 797.16	F(000) = 410
Triclinic, P1	D_x = 1.417 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.5125 (2) Å	Cell parameters from 9549 reflections
b = 8.6671 (3) Å	θ = 3.3–28.4°
c = 15.3079 (5) Å	µ = 0.64 mm⁻¹
α = 86.198 (3)°	T = 296 K
β = 76.249 (4)°	Block, colourless
γ = 74.730 (3)°	0.15 × 0.11 × 0.10 mm
V = 933.97 (5) Å³

Data collection top

Bruker APEXII CCD diffractometer	4638 independent reflections
Radiation source: fine-focus sealed tube	4538 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.044
φ and ω scans	θ_max = 28.4°, θ_min = 3.3°
Absorption correction: multi-scan (SADABS; Bruker, 2012)	h = −10→10
T_min = 0.595, T_max = 0.746	k = −11→11
46611 measured reflections	l = −20→20

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.027	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.068	w = 1/[σ²(F_o²) + (0.0332P)² + 0.4012P] where P = (F_o² + 2F_c²)/3
S = 1.09	(Δ/σ)_max = 0.001
4638 reflections	Δρ_max = 0.42 e Å⁻³
243 parameters	Δρ_min = −1.02 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.063 (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. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

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

	x	y	z	U_iso*/U_eq
Cd1	0.0000	0.0000	0.0000	0.03023 (7)
O1	0.1214 (2)	0.0630 (2)	−0.22948 (11)	0.0618 (4)
O2	0.25363 (17)	0.01600 (17)	−0.11090 (8)	0.0414 (3)
O3	−0.5079 (2)	0.6289 (2)	0.12687 (10)	0.0600 (4)
O4	0.1904 (2)	−0.1246 (2)	0.09660 (10)	0.0536 (4)
H41	0.281 (4)	−0.194 (3)	0.0977 (17)	0.054 (7)*
H42	0.106 (4)	−0.123 (3)	0.147 (2)	0.064 (8)*
N1	−0.01528 (19)	0.24366 (16)	0.06156 (9)	0.0312 (3)
N2	−0.4728 (2)	0.58766 (18)	0.27019 (10)	0.0400 (3)
N3	1.1521 (3)	−0.2028 (3)	−0.46792 (15)	0.0799 (7)
C1	0.2592 (2)	0.0188 (2)	−0.19381 (12)	0.0349 (3)
C2	0.4546 (2)	−0.03711 (19)	−0.25493 (11)	0.0324 (3)
C3	0.6144 (2)	−0.0663 (2)	−0.21992 (12)	0.0388 (4)
H3	0.6008	−0.0560	−0.1584	0.047*
C4	0.7941 (3)	−0.1105 (2)	−0.27535 (13)	0.0431 (4)
H4	0.9008	−0.1289	−0.2515	0.052*
C5	0.8134 (3)	−0.1272 (2)	−0.36706 (12)	0.0412 (4)
C6	0.6546 (3)	−0.1021 (3)	−0.40264 (13)	0.0498 (5)
H6	0.6684	−0.1152	−0.4639	0.060*
C7	0.4760 (3)	−0.0575 (3)	−0.34684 (13)	0.0449 (4)
H7	0.3694	−0.0409	−0.3706	0.054*
C8	1.0022 (3)	−0.1694 (3)	−0.42433 (14)	0.0546 (5)
C9	−0.1852 (2)	0.33349 (19)	0.10302 (11)	0.0317 (3)
H9	−0.2919	0.2972	0.1045	0.038*
C10	−0.2092 (2)	0.47761 (19)	0.14372 (11)	0.0322 (3)
C11	−0.0502 (3)	0.5326 (2)	0.13986 (13)	0.0410 (4)
H11	−0.0611	0.6289	0.1666	0.049*
C12	0.1253 (3)	0.4418 (2)	0.09551 (13)	0.0413 (4)
H12	0.2339	0.4768	0.0916	0.050*
C13	0.1368 (2)	0.2986 (2)	0.05715 (11)	0.0347 (3)
H13	0.2549	0.2382	0.0272	0.042*
C14	−0.4097 (2)	0.57261 (19)	0.18114 (11)	0.0357 (3)
C15	−0.3659 (3)	0.5045 (3)	0.33602 (13)	0.0504 (5)
H15A	−0.2440	0.4405	0.3041	0.060*
H15B	−0.4343	0.4325	0.3716	0.060*
C16	−0.3345 (4)	0.6172 (4)	0.39795 (18)	0.0699 (7)
H16A	−0.2536	0.5578	0.4353	0.105*
H16B	−0.4540	0.6715	0.4351	0.105*
H16C	−0.2757	0.6942	0.3630	0.105*
C17	−0.6711 (3)	0.6737 (3)	0.30629 (14)	0.0497 (5)
H17A	−0.7148	0.7492	0.2615	0.060*
H17B	−0.6784	0.7340	0.3588	0.060*
C18	−0.7992 (4)	0.5630 (5)	0.3320 (3)	0.0889 (9)
H18A	−0.9278	0.6245	0.3520	0.133*
H18B	−0.7624	0.4932	0.3796	0.133*
H18C	−0.7892	0.5003	0.2808	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cd1	0.02713 (10)	0.02936 (10)	0.03006 (10)	−0.00088 (6)	−0.00360 (6)	−0.00758 (6)
O1	0.0332 (7)	0.0956 (13)	0.0485 (8)	−0.0023 (7)	−0.0093 (6)	−0.0017 (8)
O2	0.0319 (6)	0.0535 (7)	0.0368 (6)	−0.0134 (5)	0.0008 (5)	−0.0081 (5)
O3	0.0519 (8)	0.0668 (10)	0.0434 (7)	0.0231 (7)	−0.0171 (6)	−0.0088 (7)
O4	0.0356 (7)	0.0698 (10)	0.0435 (8)	0.0135 (7)	−0.0154 (6)	−0.0032 (7)
N1	0.0306 (6)	0.0294 (6)	0.0299 (6)	−0.0027 (5)	−0.0043 (5)	−0.0043 (5)
N2	0.0396 (8)	0.0360 (7)	0.0348 (7)	0.0049 (6)	−0.0053 (6)	−0.0024 (6)
N3	0.0532 (12)	0.0997 (18)	0.0569 (12)	0.0069 (12)	0.0145 (10)	0.0032 (12)
C1	0.0303 (8)	0.0347 (8)	0.0379 (8)	−0.0093 (6)	−0.0026 (6)	−0.0019 (6)
C2	0.0316 (8)	0.0321 (7)	0.0316 (7)	−0.0088 (6)	−0.0025 (6)	−0.0002 (6)
C3	0.0349 (8)	0.0493 (10)	0.0304 (8)	−0.0102 (7)	−0.0034 (6)	−0.0040 (7)
C4	0.0319 (8)	0.0531 (11)	0.0403 (9)	−0.0068 (7)	−0.0045 (7)	−0.0029 (8)
C5	0.0382 (9)	0.0396 (9)	0.0366 (9)	−0.0040 (7)	0.0030 (7)	−0.0005 (7)
C6	0.0509 (11)	0.0634 (13)	0.0281 (8)	−0.0073 (9)	−0.0025 (7)	−0.0041 (8)
C7	0.0399 (9)	0.0581 (11)	0.0353 (9)	−0.0084 (8)	−0.0102 (7)	−0.0019 (8)
C8	0.0476 (11)	0.0586 (12)	0.0410 (10)	0.0007 (9)	0.0049 (9)	0.0023 (9)
C9	0.0305 (7)	0.0277 (7)	0.0343 (8)	−0.0040 (6)	−0.0053 (6)	−0.0027 (6)
C10	0.0369 (8)	0.0266 (7)	0.0286 (7)	0.0011 (6)	−0.0087 (6)	−0.0012 (6)
C11	0.0485 (10)	0.0296 (8)	0.0475 (10)	−0.0071 (7)	−0.0173 (8)	−0.0066 (7)
C12	0.0383 (9)	0.0404 (9)	0.0499 (10)	−0.0132 (7)	−0.0154 (8)	0.0004 (8)
C13	0.0309 (8)	0.0366 (8)	0.0330 (8)	−0.0033 (6)	−0.0065 (6)	−0.0001 (6)
C14	0.0382 (8)	0.0266 (7)	0.0358 (8)	0.0039 (6)	−0.0086 (7)	−0.0048 (6)
C15	0.0534 (11)	0.0517 (11)	0.0361 (9)	0.0024 (9)	−0.0098 (8)	0.0041 (8)
C16	0.0641 (15)	0.0883 (19)	0.0550 (13)	−0.0054 (13)	−0.0218 (12)	−0.0106 (13)
C17	0.0414 (10)	0.0518 (11)	0.0422 (10)	0.0050 (8)	−0.0007 (8)	−0.0062 (8)
C18	0.0602 (16)	0.111 (3)	0.097 (2)	−0.0325 (17)	−0.0083 (16)	−0.003 (2)

Geometric parameters (Å, º) top

Cd1—O2	2.2588 (12)	C6—H6	0.9300
Cd1—O2ⁱ	2.2588 (12)	C7—H7	0.9300
Cd1—O4	2.3192 (14)	C8—N3	1.138 (3)
Cd1—O4ⁱ	2.3192 (14)	C9—C10	1.383 (2)
Cd1—N1	2.3336 (13)	C9—H9	0.9300
Cd1—N1ⁱ	2.3336 (13)	C10—C11	1.386 (3)
O2—C1	1.259 (2)	C10—C14	1.508 (2)
O3—C14	1.233 (2)	C11—C12	1.384 (3)
O4—H41	0.78 (3)	C11—H11	0.9300
O4—H42	0.87 (3)	C12—H12	0.9300
N1—C9	1.340 (2)	C13—C12	1.382 (3)
N1—C13	1.335 (2)	C13—H13	0.9300
N2—C15	1.471 (2)	C14—N2	1.336 (2)
N2—C17	1.469 (2)	C15—C16	1.503 (3)
C1—O1	1.244 (2)	C15—H15A	0.9700
C2—C1	1.516 (2)	C15—H15B	0.9700
C2—C3	1.386 (2)	C16—H16A	0.9600
C2—C7	1.395 (2)	C16—H16B	0.9600
C3—C4	1.384 (2)	C16—H16C	0.9600
C3—H3	0.9300	C17—C18	1.503 (4)
C4—H4	0.9300	C17—H17A	0.9700
C5—C4	1.390 (3)	C17—H17B	0.9700
C5—C6	1.387 (3)	C18—H18A	0.9600
C5—C8	1.446 (3)	C18—H18B	0.9600
C6—C7	1.380 (3)	C18—H18C	0.9600

O2ⁱ—Cd1—O2	180.00 (6)	C6—C7—H7	119.9
O2—Cd1—O4	92.15 (5)	N3—C8—C5	178.6 (3)
O2ⁱ—Cd1—O4	87.85 (5)	N1—C9—C10	123.03 (15)
O2—Cd1—O4ⁱ	87.85 (5)	N1—C9—H9	118.5
O2ⁱ—Cd1—O4ⁱ	92.15 (5)	C10—C9—H9	118.5
O2—Cd1—N1	92.46 (5)	C9—C10—C11	118.26 (15)
O2ⁱ—Cd1—N1	87.54 (5)	C9—C10—C14	117.30 (15)
O2—Cd1—N1ⁱ	87.54 (5)	C11—C10—C14	124.12 (15)
O2ⁱ—Cd1—N1ⁱ	92.46 (5)	C10—C11—H11	120.5
O4—Cd1—O4ⁱ	180.00 (5)	C12—C11—C10	118.93 (16)
O4—Cd1—N1	87.91 (6)	C12—C11—H11	120.5
O4ⁱ—Cd1—N1	92.09 (6)	C11—C12—H12	120.5
O4—Cd1—N1ⁱ	92.09 (6)	C13—C12—C11	119.07 (16)
O4ⁱ—Cd1—N1ⁱ	87.91 (6)	C13—C12—H12	120.5
N1ⁱ—Cd1—N1	180.00 (11)	N1—C13—C12	122.42 (16)
C1—O2—Cd1	125.35 (11)	N1—C13—H13	118.8
Cd1—O4—H41	141.0 (19)	C12—C13—H13	118.8
Cd1—O4—H42	101.5 (18)	O3—C14—N2	123.71 (16)
H41—O4—H42	110 (3)	O3—C14—C10	117.33 (15)
C9—N1—Cd1	118.45 (11)	N2—C14—C10	118.94 (14)
C13—N1—Cd1	123.28 (11)	N2—C15—C16	112.93 (19)
C13—N1—C9	118.27 (14)	N2—C15—H15A	109.0
C14—N2—C15	124.30 (15)	N2—C15—H15B	109.0
C14—N2—C17	118.61 (15)	C16—C15—H15A	109.0
C17—N2—C15	116.50 (16)	C16—C15—H15B	109.0
O1—C1—O2	126.45 (16)	H15A—C15—H15B	107.8
O1—C1—C2	117.84 (16)	C15—C16—H16A	109.5
O2—C1—C2	115.71 (15)	C15—C16—H16B	109.5
C3—C2—C1	120.04 (15)	C15—C16—H16C	109.5
C3—C2—C7	119.33 (16)	H16A—C16—H16B	109.5
C7—C2—C1	120.63 (16)	H16A—C16—H16C	109.5
C2—C3—H3	119.6	H16B—C16—H16C	109.5
C4—C3—C2	120.80 (16)	N2—C17—C18	112.4 (2)
C4—C3—H3	119.6	N2—C17—H17A	109.1
C3—C4—C5	119.28 (17)	N2—C17—H17B	109.1
C3—C4—H4	120.4	C18—C17—H17A	109.1
C5—C4—H4	120.4	C18—C17—H17B	109.1
C4—C5—C8	118.55 (19)	H17A—C17—H17B	107.9
C6—C5—C4	120.48 (17)	C17—C18—H18A	109.5
C6—C5—C8	120.97 (18)	C17—C18—H18B	109.5
C5—C6—H6	120.1	C17—C18—H18C	109.5
C7—C6—C5	119.80 (17)	H18A—C18—H18B	109.5
C7—C6—H6	120.1	H18A—C18—H18C	109.5
C2—C7—H7	119.9	H18B—C18—H18C	109.5
C6—C7—C2	120.28 (17)

O2—Cd1—N1—C9	148.84 (12)	C7—C2—C1—O2	172.21 (17)
O2ⁱ—Cd1—N1—C9	−31.16 (12)	C1—C2—C3—C4	−177.11 (17)
O2—Cd1—N1—C13	−30.80 (13)	C7—C2—C3—C4	2.0 (3)
O2ⁱ—Cd1—N1—C13	149.20 (13)	C1—C2—C7—C6	177.33 (19)
O4—Cd1—N1—C9	−119.09 (12)	C3—C2—C7—C6	−1.7 (3)
O4ⁱ—Cd1—N1—C9	60.91 (12)	C2—C3—C4—C5	−0.6 (3)
O4—Cd1—N1—C13	61.26 (13)	C6—C5—C4—C3	−0.9 (3)
O4ⁱ—Cd1—N1—C13	−118.74 (13)	C8—C5—C4—C3	178.4 (2)
O4—Cd1—O2—C1	152.29 (15)	C4—C5—C6—C7	1.2 (3)
O4ⁱ—Cd1—O2—C1	−27.71 (15)	C8—C5—C6—C7	−178.2 (2)
N1—Cd1—O2—C1	−119.71 (14)	C5—C6—C7—C2	0.2 (3)
N1ⁱ—Cd1—O2—C1	60.29 (14)	N1—C9—C10—C11	1.2 (2)
Cd1—O2—C1—O1	24.2 (3)	N1—C9—C10—C14	175.06 (15)
Cd1—O2—C1—C2	−156.03 (11)	C9—C10—C11—C12	0.1 (3)
Cd1—N1—C9—C10	178.26 (12)	C14—C10—C11—C12	−173.25 (17)
C13—N1—C9—C10	−2.1 (2)	C9—C10—C14—O3	−67.2 (2)
Cd1—N1—C13—C12	−178.75 (13)	C9—C10—C14—N2	111.03 (19)
C9—N1—C13—C12	1.6 (2)	C11—C10—C14—O3	106.3 (2)
C14—N2—C15—C16	122.5 (2)	C11—C10—C14—N2	−75.5 (2)
C17—N2—C15—C16	−66.5 (3)	C10—C11—C12—C13	−0.6 (3)
C14—N2—C17—C18	95.2 (3)	N1—C13—C12—C11	−0.3 (3)
C15—N2—C17—C18	−76.3 (3)	O3—C14—N2—C17	1.0 (3)
C3—C2—C1—O1	171.04 (18)	O3—C14—N2—C15	171.9 (2)
C3—C2—C1—O2	−8.7 (2)	C10—C14—N2—C17	−177.05 (17)
C7—C2—C1—O1	−8.0 (3)	C10—C14—N2—C15	−6.2 (3)

Symmetry code: (i) −x, −y, −z.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O3ⁱⁱ	0.78 (3)	2.01 (3)	2.781 (2)	169 (3)
O4—H42···O1ⁱ	0.87 (3)	1.84 (3)	2.670 (2)	159 (3)

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

Acknowledgements

The authors acknowledge the Scientific and Technological Research Application and Research Center, Sinop University, Turkey, for the use of the Bruker D8 QUEST diffractometer. This work was supported financially by Kafkas University, Scientific Research Projects Coordinator (project No. 2016-FM-49).

References

Adiwidjaja, G., Rossmanith, E. & Küppers, H. (1978). Acta Cryst. B34, 3079–3083. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Antsyshkina, A. S., Chiragov, F. M. & Poray-Koshits, M. A. (1980). Koord. Khim. 15, 1098–1103. Google Scholar
Bigoli, F., Braibanti, A., Pellinghelli, M. A. & Tiripicchio, A. (1972). Acta Cryst. B28, 962–966. CSD CrossRef CAS IUCr Journals Web of Science Google Scholar
Bruker (2012). APEX2, SAINT and SADABS. Bruker AXS Inc. Madison, Wisconsin, USA. Google Scholar
Catterick (neé Drew), J., Hursthouse, M. B., New, D. B. & Thornton, P. (1974). J. Chem. Soc. Chem. Commun. pp. 843–844. Google Scholar
Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849–854. Web of Science CrossRef CAS IUCr Journals Google Scholar
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009a). Acta Cryst. E65, m466–m467. Web of Science CSD CrossRef IUCr Journals Google Scholar
Hökelek, T., Dal, H., Tercan, B., Özbek, F. E. & Necefoğlu, H. (2009b). Acta Cryst. E65, m545–m546. Web of Science CSD CrossRef IUCr Journals Google Scholar
Krishnamachari, K. A. V. R. (1974). Am. J. Clin. Nutr. 27, 108–111. CAS PubMed Web of Science Google Scholar
Nadzhafov, G. N., Shnulin, A. N. & Mamedov, Kh. S. (1981). Zh. Strukt. Khim. 22, 124–128. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shnulin, A. N., Nadzhafov, G. N., Amiraslanov, I. R., Usubaliev, B. T. & Mamedov, Kh. S. (1981). Koord. Khim. 7, 1409–1416. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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