Diaqua-bis-(N,N-diethyl-nicotinamide-κN)bis[4-(dimethyl-amino)-benzoato-κO]cobalt(II).

The title Co(II) complex, [Co(C(9)H(10)NO(2))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], is centrosymmetric. It contains two dimethyl-amino-benzoate (DMAB) and two diethyl-nicotinamide (DENA) ligands and two water mol-ecules, 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 octa-hedral 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 carboxyl-ate group by -0.781 (1) Å. The dihedral angle between the carboxyl-ate 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, inter-molecular O-H⋯O and C-H⋯O hydrogen bonds link the mol-ecules into a three-dimensional network. Two weak C-H⋯π inter-actions 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 = 779.79

Monoclinic,

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[F 2 > 2σ(F 2)] = 0.031

wR(F 2) = 0.081

S = 1.05

4821 reflections

251 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.40 e Å−3

Δρmin = −0.30 e Å−3

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 ▶).

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

[Co(C9H10NO2)2(C10H14N2O)2(H2O)2]	F(000) = 826
Mr = 779.79	Dx = 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

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

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(Fo2) + (0.0382P)2 + 0.7829P] where P = (Fo2 + 2Fc2)/3
4821 reflections	(Δ/σ)max < 0.001
251 parameters	Δρmax = 0.40 e Å−3
3 restraints	Δρmin = −0.30 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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

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···O3iv	0.98	2.47	3.403 (2)	160
C15—H15A···Cg2v	0.98	2.86	3.734 (2)	148
C18—H18B···Cg1vi	0.98	2.86	3.7907 (19)	158

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⋯O3iv	0.98	2.47	3.403 (2)	160
C15—H15A⋯Cg2v	0.98	2.86	3.734 (2)	148
C18—H18B⋯Cg1vi	0.98	2.86	3.7907 (19)	158

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) . Cg1 and Cg2 are the cetroids of the C2–C7 and N1/C8–C12 rings, respectively.