Diaqua­bis­(N,N-diethyl­nicotinamide-κN1)bis[4-(dimethyl­amino)­benzoato-κO]cobalt(II)

Hökelek, T.; Dal, H.; Tercan, B.; Aybirdi, Ö.; Necefoğlu, H.

doi:10.1107/S1600536809030980

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 9| September 2009| Pages m1051-m1052

doi:10.1107/S1600536809030980

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Diaquabis(N,N-diethylnicotinamide-κN¹)bis[4-(dimethylamino)benzoato-κO]cobalt(II)

Tuncer Hökelek,^a ^* Hakan Dal,^b Barış Tercan,^c Özgür Aybirdi ^d and Hacali Necefoğlu ^d

^aHacettepe University, Department of Physics, 06800 Beytepe, Ankara, Turkey, ^bAnadolu University, Faculty of Science, Department of Chemistry, 26470 Yenibağlar, Eskişehir, Turkey, ^cKarabük University, Department of Physics, 78050, Karabük, Turkey, and ^dKafkas University, Department of Chemistry, 63100 Kars, Turkey
^*Correspondence e-mail: merzifon@hacettepe.edu.tr

(Received 4 August 2009; accepted 4 August 2009; online 8 August 2009)

The title Co^II complex, [Co(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂], is centrosymmetric. It contains two dimethylaminobenzoate (DMAB) and two diethylnicotinamide (DENA) ligands and two water molecules, all of them being monodentate. The four O atoms in the equatorial plane around the Co atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two pyridine N atoms of DENA ligands with the Co—N distance of 2.1519 (11) Å in the axial positions. The Co atom is displaced out of the least-squares plane of the carboxylate group by −0.781 (1) Å. The dihedral angle between the carboxylate group and the adjacent benzene ring is 5.05 (7)°, while the pyridine and benzene rings are oriented at a dihedral angle of 71.48 (5)°. In the crystal structure, intermolecular O—H⋯O and C—H⋯O hydrogen bonds link the molecules into a three-dimensional network. Two weak C—H⋯π interactions are also present.

Related literature

For general background, see: Bigoli et al. (1972 ); Krishnamachari (1974 ). For related structures, see: Hökelek & Necefoğlu (2007 ); Sertçelik et al. (2009 ).

Experimental

Crystal data

[Co(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r = 779.79
Monoclinic, P 2₁ /c
a = 6.5184 (1) Å
b = 20.4829 (3) Å
c = 14.6481 (2) Å
β = 98.492 (1)°
V = 1934.31 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 100 K
0.42 × 0.22 × 0.12 mm

Data collection

Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.817, T_max = 0.942
18749 measured reflections
4821 independent reflections
4137 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.081
S = 1.05
4821 reflections
251 parameters
3 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.40 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O4—H41⋯O2ⁱ	0.908 (16)	1.777 (15)	2.6621 (14)	164.0 (16)
O4—H42⋯O2ⁱⁱ	0.907 (16)	1.898 (15)	2.7802 (14)	163.4 (14)
C9—H9⋯O3ⁱⁱⁱ	0.95	2.41	3.3447 (17)	168
C19—H19A⋯O3^iv	0.98	2.47	3.403 (2)	160
C15—H15A⋯Cg2^v	0.98	2.86	3.734 (2)	148
C18—H18B⋯Cg1^vi	0.98	2.86	3.7907 (19)	158
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iv) x, y, z-1; (v) x+1, y, z; (vi) -x+1, -y+1, -z. Cg1 and Cg2 are the cetroids of the C2–C7 and N1/C8–C12 rings, respectively.

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2003 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809030980/xu2578sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809030980/xu2578Isup2.hkl

checkCIF report

Comment top

As a part of our ongoing investigation on transition metal complexes of nicotinamide (NA), one form of niacin (Krishnamachari, 1974), and/or the nicotinic acid derivative N,N-diethylnicotinamide (DENA), an important respiratory stimulant (Bigoli et al., 1972), the title compound was synthesized and its crystal structure is reported herein.

The title compound is a monomeric complex, with Co^II ion on a centre of symmetry, consisting of two DENA and two dimethylaminobenzoate (DMAB) ligands and two water molecules. The structures of similar DENA and/or NA complexes of Co^II ion, [Co(C₈H₅O₃)₂(C₁₀H₁₄N₂O)₂(H₂O)₂] (Sertçelik et al., 2009) and [Co(C₉H₁₀NO₂)₂(C₆H₆N₂O)₂(H₂O)₂] (Hökelek & Necefoğlu, 2007) have also been determined.

In the title compound, all ligands are monodentate. The four O atoms (O1, O4, and the symmetry-related atoms, O1', O4') in the equatorial plane around the Co atom form a slightly distorted square-planar arrangement, while the slightly distorted octahedral coordination is completed by the two pyridine N atoms (N1, N1') of the DENA ligands at 2.1519 (11) Å from the Co atom in the axial positions (Fig. 1). The average Co—O bond length is 2.0955 (10) Å and the Co atom is displaced out of the least-squares plane of the carboxylate group (O1/C1/O2) by -0.781 (1) Å. The dihedral angle between the planar carboxylate group and the benzene ring A (C2—C7) is 5.05 (7)°, while that between rings A and B (N1/C8—C12) is 71.48 (5)°.

In the crystal structure, intermolecular O—H···O and C—H···O hydrogen bonds (Table 1) link the molecules into a three-dimensional network, in which they may be effective in the stabilization of the structure. Two weak C—H···π interactions (Table 1) are also found.

Related literature top

For general background, see: Bigoli et al. (1972); Krishnamachari (1974). For related structures, see: Hökelek & Necefoğlu (2007); Sertçelik et al. (2009).

Experimental top

The title compound was prepared by the reaction of CoSO₄.7H₂O (1.41 g, 5 mmol) in H₂O (50 ml) and DENA (1.78 g, 10 mmol) in H₂O (50 ml) with sodium p-dimethylaminobenzoate (1.88 g, 10 mmol) in H₂O (100 ml). The mixture was filtered and set aside to crystallize at ambient temperature for one week, giving red single crystals.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2006); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Figures top

Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Primed atoms are generated by the symmetry operator:(') -x, -y, -z.

Diaquabis(N,N-diethylnicotinamide-κN¹)bis[4- (dimethylamino)benzoato-κO]cobalt(II) top

Crystal data top

[Co(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	F(000) = 826
M_r = 779.79	D_x = 1.339 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 9065 reflections
a = 6.5184 (1) Å	θ = 2.4–28.3°
b = 20.4829 (3) Å	µ = 0.50 mm⁻¹
c = 14.6481 (2) Å	T = 100 K
β = 98.492 (1)°	Block, red
V = 1934.31 (5) Å³	0.42 × 0.22 × 0.12 mm
Z = 2

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4821 independent reflections
Radiation source: fine-focus sealed tube	4137 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
ϕ and ω scans	θ_max = 28.3°, θ_min = 1.7°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.817, T_max = 0.942	k = −26→27
18749 measured reflections	l = −19→19

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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	w = 1/[σ²(F_o²) + (0.0382P)² + 0.7829P] where P = (F_o² + 2F_c²)/3
4821 reflections	(Δ/σ)_max < 0.001
251 parameters	Δρ_max = 0.40 e Å⁻³
3 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Co(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]	V = 1934.31 (5) Å³
M_r = 779.79	Z = 2
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.5184 (1) Å	µ = 0.50 mm⁻¹
b = 20.4829 (3) Å	T = 100 K
c = 14.6481 (2) Å	0.42 × 0.22 × 0.12 mm
β = 98.492 (1)°

Data collection top

Bruker Kappa APEXII CCD area-detector diffractometer	4821 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	4137 reflections with I > 2σ(I)
T_min = 0.817, T_max = 0.942	R_int = 0.024
18749 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	3 restraints
wR(F²) = 0.081	H atoms treated by a mixture of independent and constrained refinement
S = 1.05	Δρ_max = 0.40 e Å⁻³
4821 reflections	Δρ_min = −0.30 e Å⁻³
251 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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
Co1	0.5000	0.5000	0.5000	0.01335 (8)
O1	0.54021 (15)	0.50614 (5)	0.36270 (6)	0.0169 (2)
O2	0.87853 (15)	0.52883 (5)	0.37060 (7)	0.0196 (2)
O3	0.76748 (16)	0.28543 (5)	0.75280 (7)	0.0219 (2)
O4	0.20770 (15)	0.45517 (5)	0.45875 (7)	0.0182 (2)
H41	0.162 (3)	0.4543 (8)	0.5144 (10)	0.023*
H42	0.114 (3)	0.4789 (9)	0.4204 (11)	0.023*
N1	0.63544 (17)	0.40399 (6)	0.51022 (8)	0.0155 (2)
N2	1.09307 (19)	0.27891 (6)	0.71639 (8)	0.0191 (2)
N3	0.6955 (2)	0.39432 (7)	−0.02756 (9)	0.0301 (3)
C1	0.7089 (2)	0.50704 (6)	0.32932 (9)	0.0151 (3)
C2	0.7037 (2)	0.47929 (7)	0.23444 (9)	0.0163 (3)
C3	0.5191 (2)	0.45744 (7)	0.18361 (10)	0.0208 (3)
H3	0.3938	0.4610	0.2092	0.025*
C4	0.5143 (2)	0.43063 (8)	0.09649 (10)	0.0241 (3)
H4	0.3857	0.4170	0.0628	0.029*
C5	0.6975 (2)	0.42340 (7)	0.05741 (10)	0.0224 (3)
C6	0.8826 (2)	0.44567 (8)	0.10906 (10)	0.0235 (3)
H6	1.0089	0.4418	0.0844	0.028*
C7	0.8845 (2)	0.47324 (7)	0.19537 (10)	0.0206 (3)
H7	1.0118	0.4883	0.2286	0.025*
C8	0.6312 (2)	0.36554 (7)	0.43557 (9)	0.0172 (3)
H8	0.5692	0.3820	0.3774	0.021*
C9	0.7131 (2)	0.30305 (7)	0.43964 (9)	0.0192 (3)
H9	0.7071	0.2772	0.3855	0.023*
C10	0.8040 (2)	0.27915 (7)	0.52449 (10)	0.0186 (3)
H10	0.8615	0.2365	0.5295	0.022*
C11	0.8101 (2)	0.31852 (7)	0.60242 (9)	0.0153 (3)
C12	0.7227 (2)	0.38028 (7)	0.59202 (9)	0.0150 (3)
H12	0.7248	0.4069	0.6452	0.018*
C13	0.8903 (2)	0.29329 (6)	0.69730 (9)	0.0160 (3)
C14	1.2464 (2)	0.29630 (8)	0.65634 (11)	0.0251 (3)
H14A	1.3649	0.3187	0.6937	0.030*
H14B	1.1825	0.3273	0.6086	0.030*
C15	1.3266 (3)	0.23750 (10)	0.60918 (14)	0.0388 (4)
H15A	1.4134	0.2523	0.5640	0.058*
H15B	1.2091	0.2124	0.5776	0.058*
H15C	1.4089	0.2099	0.6555	0.058*
C16	1.1660 (2)	0.24446 (8)	0.80324 (11)	0.0248 (3)
H16A	1.1023	0.2647	0.8537	0.030*
H16B	1.3183	0.2495	0.8183	0.030*
C17	1.1129 (3)	0.17229 (8)	0.79793 (12)	0.0311 (4)
H17A	1.1568	0.1520	0.8582	0.047*
H17B	1.1848	0.1513	0.7515	0.047*
H17C	0.9628	0.1670	0.7806	0.047*
C18	0.5005 (3)	0.37807 (9)	−0.08350 (11)	0.0334 (4)
H18A	0.5267	0.3611	−0.1432	0.050*
H18B	0.4139	0.4173	−0.0933	0.050*
H18C	0.4287	0.3448	−0.0519	0.050*
C19	0.8816 (3)	0.39299 (9)	−0.06991 (12)	0.0361 (4)
H19A	0.8523	0.3719	−0.1305	0.054*
H19B	0.9896	0.3685	−0.0305	0.054*
H19C	0.9295	0.4378	−0.0775	0.054*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01466 (13)	0.01570 (13)	0.00949 (12)	0.00226 (9)	0.00115 (9)	−0.00087 (9)
O1	0.0169 (5)	0.0216 (5)	0.0122 (4)	0.0031 (4)	0.0019 (4)	−0.0006 (4)
O2	0.0188 (5)	0.0258 (5)	0.0138 (5)	−0.0010 (4)	0.0015 (4)	−0.0012 (4)
O3	0.0251 (5)	0.0259 (5)	0.0155 (5)	0.0055 (4)	0.0056 (4)	0.0033 (4)
O4	0.0183 (5)	0.0221 (5)	0.0137 (5)	0.0017 (4)	0.0008 (4)	−0.0024 (4)
N1	0.0156 (5)	0.0179 (6)	0.0130 (5)	0.0010 (4)	0.0020 (4)	−0.0005 (4)
N2	0.0193 (6)	0.0192 (6)	0.0179 (6)	0.0021 (5)	0.0001 (5)	0.0018 (5)
N3	0.0372 (8)	0.0363 (8)	0.0173 (6)	0.0003 (6)	0.0056 (6)	−0.0098 (6)
C1	0.0194 (6)	0.0140 (6)	0.0118 (6)	0.0035 (5)	0.0016 (5)	0.0023 (5)
C2	0.0200 (7)	0.0168 (6)	0.0121 (6)	0.0016 (5)	0.0028 (5)	0.0014 (5)
C3	0.0207 (7)	0.0245 (7)	0.0180 (7)	−0.0003 (6)	0.0050 (6)	−0.0027 (6)
C4	0.0243 (8)	0.0290 (8)	0.0180 (7)	−0.0020 (6)	0.0000 (6)	−0.0041 (6)
C5	0.0319 (8)	0.0204 (7)	0.0153 (7)	0.0009 (6)	0.0052 (6)	−0.0018 (5)
C6	0.0248 (7)	0.0281 (8)	0.0193 (7)	0.0007 (6)	0.0091 (6)	−0.0032 (6)
C7	0.0205 (7)	0.0250 (7)	0.0164 (7)	0.0002 (6)	0.0034 (5)	−0.0010 (6)
C8	0.0185 (7)	0.0204 (7)	0.0126 (6)	−0.0010 (5)	0.0017 (5)	−0.0007 (5)
C9	0.0235 (7)	0.0194 (7)	0.0148 (6)	−0.0003 (5)	0.0035 (5)	−0.0048 (5)
C10	0.0213 (7)	0.0162 (6)	0.0186 (7)	0.0025 (5)	0.0038 (5)	−0.0021 (5)
C11	0.0150 (6)	0.0184 (6)	0.0128 (6)	0.0001 (5)	0.0030 (5)	0.0003 (5)
C12	0.0153 (6)	0.0171 (6)	0.0128 (6)	−0.0001 (5)	0.0022 (5)	−0.0019 (5)
C13	0.0204 (7)	0.0121 (6)	0.0150 (6)	0.0019 (5)	0.0008 (5)	−0.0017 (5)
C14	0.0182 (7)	0.0306 (8)	0.0264 (8)	−0.0030 (6)	0.0027 (6)	−0.0001 (6)
C15	0.0240 (8)	0.0493 (11)	0.0455 (11)	−0.0045 (8)	0.0126 (8)	−0.0178 (9)
C16	0.0257 (8)	0.0248 (8)	0.0210 (7)	0.0051 (6)	−0.0058 (6)	0.0027 (6)
C17	0.0355 (9)	0.0238 (8)	0.0331 (9)	0.0070 (7)	0.0016 (7)	0.0064 (7)
C18	0.0487 (11)	0.0339 (9)	0.0168 (7)	−0.0074 (8)	0.0026 (7)	−0.0067 (6)
C19	0.0560 (12)	0.0315 (9)	0.0251 (8)	−0.0078 (8)	0.0200 (8)	−0.0086 (7)

Geometric parameters (Å, º) top

Co1—O1	2.0701 (9)	C7—H7	0.9500
Co1—O1ⁱ	2.0701 (9)	C8—H8	0.9500
Co1—O4	2.1209 (10)	C9—C8	1.385 (2)
Co1—O4ⁱ	2.1209 (10)	C9—C10	1.385 (2)
Co1—N1	2.1519 (11)	C9—H9	0.9500
Co1—N1ⁱ	2.1519 (11)	C10—C11	1.3934 (18)
O1—C1	1.2676 (16)	C10—H10	0.9500
O2—C1	1.2611 (17)	C11—C12	1.3863 (19)
O3—C13	1.2332 (17)	C12—H12	0.9500
O4—H41	0.908 (13)	C13—C11	1.5026 (18)
O4—H42	0.907 (14)	C14—H14A	0.9900
N1—C8	1.3445 (17)	C14—H14B	0.9900
N1—C12	1.3393 (17)	C15—C14	1.519 (2)
N2—C13	1.3423 (18)	C15—H15A	0.9800
N2—C14	1.4696 (19)	C15—H15B	0.9800
N2—C16	1.4710 (18)	C15—H15C	0.9800
N3—C5	1.3782 (18)	C16—H16A	0.9900
N3—C18	1.446 (2)	C16—H16B	0.9900
N3—C19	1.442 (2)	C17—C16	1.518 (2)
C2—C1	1.4973 (18)	C17—H17A	0.9800
C3—C2	1.392 (2)	C17—H17B	0.9800
C3—H3	0.9500	C17—H17C	0.9800
C4—C3	1.385 (2)	C18—H18A	0.9800
C4—C5	1.406 (2)	C18—H18B	0.9800
C4—H4	0.9500	C18—H18C	0.9800
C6—C7	1.383 (2)	C19—H19A	0.9800
C6—C5	1.403 (2)	C19—H19B	0.9800
C6—H6	0.9500	C19—H19C	0.9800
C7—C2	1.3896 (19)

O1ⁱ—Co1—O1	180.0	C8—C9—C10	118.46 (13)
O1—Co1—O4	89.24 (4)	C8—C9—H9	120.8
O1ⁱ—Co1—O4	90.76 (4)	C10—C9—H9	120.8
O1—Co1—O4ⁱ	90.76 (4)	C9—C10—C11	119.15 (13)
O1ⁱ—Co1—O4ⁱ	89.24 (4)	C9—C10—H10	120.4
O1—Co1—N1	90.78 (4)	C11—C10—H10	120.4
O1ⁱ—Co1—N1	89.22 (4)	C10—C11—C13	121.49 (12)
O1—Co1—N1ⁱ	89.22 (4)	C12—C11—C10	118.47 (12)
O1ⁱ—Co1—N1ⁱ	90.78 (4)	C12—C11—C13	119.79 (12)
O4—Co1—O4ⁱ	180.00 (5)	N1—C12—C11	122.85 (12)
O4—Co1—N1	88.07 (4)	N1—C12—H12	118.6
O4ⁱ—Co1—N1	91.93 (4)	C11—C12—H12	118.6
O4—Co1—N1ⁱ	91.93 (4)	O3—C13—N2	123.31 (13)
O4ⁱ—Co1—N1ⁱ	88.07 (4)	O3—C13—C11	118.90 (12)
N1—Co1—N1ⁱ	180.0	N2—C13—C11	117.76 (12)
C1—O1—Co1	128.10 (9)	N2—C14—C15	112.96 (14)
Co1—O4—H41	98.7 (11)	N2—C14—H14A	109.0
Co1—O4—H42	116.0 (11)	N2—C14—H14B	109.0
H42—O4—H41	106.6 (14)	C15—C14—H14A	109.0
C8—N1—Co1	121.32 (9)	C15—C14—H14B	109.0
C12—N1—Co1	120.62 (9)	H14A—C14—H14B	107.8
C12—N1—C8	118.05 (12)	C14—C15—H15A	109.5
C13—N2—C14	123.91 (12)	C14—C15—H15B	109.5
C13—N2—C16	117.90 (12)	C14—C15—H15C	109.5
C14—N2—C16	118.19 (12)	H15A—C15—H15B	109.5
C5—N3—C18	120.12 (14)	H15A—C15—H15C	109.5
C5—N3—C19	120.00 (14)	H15B—C15—H15C	109.5
C19—N3—C18	118.49 (13)	N2—C16—C17	112.39 (13)
O1—C1—C2	116.77 (12)	N2—C16—H16A	109.1
O2—C1—O1	124.70 (12)	N2—C16—H16B	109.1
O2—C1—C2	118.53 (12)	C17—C16—H16A	109.1
C3—C2—C1	121.19 (12)	C17—C16—H16B	109.1
C7—C2—C1	120.78 (13)	H16A—C16—H16B	107.9
C7—C2—C3	118.01 (13)	C16—C17—H17A	109.5
C2—C3—H3	119.3	C16—C17—H17B	109.5
C4—C3—C2	121.36 (14)	C16—C17—H17C	109.5
C4—C3—H3	119.3	H17A—C17—H17B	109.5
C3—C4—C5	120.77 (14)	H17A—C17—H17C	109.5
C3—C4—H4	119.6	H17B—C17—H17C	109.5
C5—C4—H4	119.6	N3—C18—H18A	109.5
N3—C5—C4	121.18 (14)	N3—C18—H18B	109.5
N3—C5—C6	121.37 (14)	N3—C18—H18C	109.5
C6—C5—C4	117.44 (13)	H18A—C18—H18B	109.5
C5—C6—H6	119.5	H18A—C18—H18C	109.5
C7—C6—C5	121.10 (14)	H18B—C18—H18C	109.5
C7—C6—H6	119.5	N3—C19—H19A	109.5
C2—C7—H7	119.3	N3—C19—H19B	109.5
C6—C7—C2	121.30 (14)	N3—C19—H19C	109.5
C6—C7—H7	119.4	H19A—C19—H19B	109.5
N1—C8—C9	123.02 (13)	H19A—C19—H19C	109.5
N1—C8—H8	118.5	H19B—C19—H19C	109.5
C9—C8—H8	118.5

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2ⁱ	0.91 (2)	1.78 (2)	2.6621 (14)	164 (2)
O4—H42···O2ⁱⁱ	0.91 (2)	1.90 (2)	2.7802 (14)	163 (1)
C9—H9···O3ⁱⁱⁱ	0.95	2.41	3.3447 (17)	168
C19—H19A···O3^iv	0.98	2.47	3.403 (2)	160
C15—H15A···Cg2^v	0.98	2.86	3.734 (2)	148
C18—H18B···Cg1^vi	0.98	2.86	3.7907 (19)	158

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

Experimental details

Crystal data
Chemical formula	[Co(C₉H₁₀NO₂)₂(C₁₀H₁₄N₂O)₂(H₂O)₂]
M_r	779.79
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	6.5184 (1), 20.4829 (3), 14.6481 (2)
β (°)	98.492 (1)
V (Å³)	1934.31 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.50
Crystal size (mm)	0.42 × 0.22 × 0.12

Data collection
Diffractometer	Bruker Kappa APEXII CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.817, 0.942
No. of measured, independent and observed [I > 2σ(I)] reflections	18749, 4821, 4137
R_int	0.024
(sin θ/λ)_max (Å⁻¹)	0.667

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.081, 1.05
No. of reflections	4821
No. of parameters	251
No. of restraints	3
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.40, −0.30

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2006), WinGX (Farrugia, 1999) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O4—H41···O2ⁱ	0.908 (16)	1.777 (15)	2.6621 (14)	164.0 (16)
O4—H42···O2ⁱⁱ	0.907 (16)	1.898 (15)	2.7802 (14)	163.4 (14)
C9—H9···O3ⁱⁱⁱ	0.95	2.41	3.3447 (17)	168
C19—H19A···O3^iv	0.98	2.47	3.403 (2)	160
C15—H15A···Cg2^v	0.98	2.86	3.734 (2)	148
C18—H18B···Cg1^vi	0.98	2.86	3.7907 (19)	158

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

Acknowledgements

The authors are indebted to Anadolu University and the Medicinal Plants and Medicine Research Centre of Anadolu University, Eskişehir, Turkey, for the use of the X-ray diffractometer. This work was supported financially by the Scientific and Technological Research Council of Turkey (grant No. 108 T657).

References

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