Diaqua-bis(N,N-diethyl-nicotinamide-κN)bis-(4-formyl-benzoato-κO)cobalt(II).

In the crystal structure of the title Co(II) complex, [Co(C(8)H(5)O(3))(2)(C(10)H(14)N(2)O)(2)(H(2)O)(2)], the metal centre is located on an inversion center and is coordinated by two 4-formyl-benzoate (FOB), two diethyl-nicotinamide (DENA) ligands and two water mol-ecules in a slightly distorted CoO(4)N(2) octa-hedral geometry. In the crystal structure, O-H⋯O hydrogen bonds link the mol-ecules into infinite chains. π-π contacts between the parallel pyridine rings of neighboring DENA ligands [centroid-centroid distance = 3.652 (3) Å] further stabilize the crystal structure.

Related literature

For general background, see: Antolini et al. (1982 ▶); Bigoli et al. (1972 ▶); Nadzhafov et al. (1981 ▶); Shnulin et al. (1981 ▶). For related structures, see: Hökelek et al. (1995 ▶, 1997 ▶, 2007 ▶, 2008 ▶); Hökelek & Necefoğlu (1996 ▶, 1997 ▶, 2007 ▶); Sertçelik et al. (2009a ▶, 2009b ▶).

Experimental

Crystal data

[Co(C8H5O3)2(C10H14N2O)2(H2O)2]

M = 749.67

Triclinic,

a = 7.2962 (2) Å

b = 8.6863 (3) Å

c = 15.9453 (5) Å

α = 85.433 (2)°

β = 78.608 (3)°

γ = 68.022 (2)°

V = 918.64 (5) Å3

Z = 1

Mo Kα radiation

μ = 0.53 mm−1

T = 294 K

0.35 × 0.25 × 0.15 mm

Data collection

Rigaku R-AXIS RAPID-S diffractometer

Absorption correction: multi-scan (Blessing, 1995 ▶) T min = 0.853, T max = 0.926

19487 measured reflections

3755 independent reflections

3016 reflections with I > 2σ(I)

R int = 0.074

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.195

S = 1.07

3755 reflections

246 parameters

3 restraints

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 1.02 e Å−3

Δρmin = −0.33 e Å−3

Data collection: CrystalClear (Rigaku/MSC, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; 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 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809008265/xu2489sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809008265/xu2489Isup2.hkl

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

[Co(C8H5O3)2(C10H14N2O)2(H2O)2]	Z = 1
Mr = 749.67	F(000) = 393
Triclinic, P1	Dx = 1.355 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 7.2962 (2) Å	Cell parameters from 4172 reflections
b = 8.6863 (3) Å	θ = 2.5–26.4°
c = 15.9453 (5) Å	µ = 0.53 mm−1
α = 85.433 (2)°	T = 294 K
β = 78.608 (3)°	Prism, red
γ = 68.022 (2)°	0.35 × 0.25 × 0.15 mm
V = 918.64 (5) Å3

Rigaku R-AXIS RAPID-S diffractometer	3755 independent reflections
Radiation source: fine-focus sealed tube	3016 reflections with I > 2σ(I)
graphite	Rint = 0.074
ω scans	θmax = 26.4°, θmin = 2.5°
Absorption correction: multi-scan (Blessing, 1995)	h = −9→9
Tmin = 0.853, Tmax = 0.926	k = −10→10
19487 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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.195	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0999P)2 + 0.5936P] where P = (Fo2 + 2Fc2)/3
3755 reflections	(Δ/σ)max < 0.001
246 parameters	Δρmax = 1.02 e Å−3
3 restraints	Δρmin = −0.33 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	0.0000	0.0000	0.0386 (3)
O1	0.4778 (5)	−0.1144 (4)	−0.10591 (18)	0.0473 (7)
O2	0.7579 (5)	−0.1290 (4)	−0.1979 (2)	0.0555 (8)
O3	0.0578 (8)	−0.1907 (7)	−0.4559 (3)	0.0958 (15)
O4	−0.2309 (5)	0.3315 (4)	−0.1246 (2)	0.0585 (9)
O5	0.2256 (5)	−0.0208 (4)	0.0630 (2)	0.0506 (8)
H51	0.224 (10)	−0.126 (4)	0.080 (3)	0.09 (2)*
H52	0.214 (9)	0.033 (5)	0.113 (2)	0.075 (18)*
N1	0.3188 (5)	0.2363 (4)	−0.0485 (2)	0.0419 (8)
N2	−0.1116 (7)	0.4197 (6)	−0.2512 (3)	0.0609 (11)
C1	0.5813 (6)	−0.1268 (5)	−0.1802 (3)	0.0422 (9)
C2	0.4825 (6)	−0.1361 (5)	−0.2530 (3)	0.0418 (9)
C3	0.5824 (7)	−0.1374 (6)	−0.3370 (3)	0.0496 (11)
H3	0.7097	−0.1317	−0.3480	0.060*
C4	0.4938 (8)	−0.1471 (7)	−0.4037 (3)	0.0570 (12)
H4	0.5613	−0.1474	−0.4596	0.068*
C5	0.3035 (8)	−0.1566 (6)	−0.3882 (3)	0.0546 (11)
C6	0.2016 (7)	−0.1530 (6)	−0.3045 (3)	0.0510 (11)
H6	0.0741	−0.1583	−0.2934	0.061*
C7	0.2906 (7)	−0.1417 (6)	−0.2383 (3)	0.0463 (10)
H7	0.2213	−0.1377	−0.1824	0.056*
C8	0.2121 (10)	−0.1698 (9)	−0.4608 (4)	0.0750 (16)
H81	0.294 (9)	−0.169 (7)	−0.522 (4)	0.086 (19)*
C9	0.3415 (6)	0.3797 (5)	−0.0385 (3)	0.0439 (10)
H9	0.4366	0.3784	−0.0070	0.053*
C10	0.2310 (7)	0.5285 (6)	−0.0724 (3)	0.0494 (10)
H10	0.2502	0.6255	−0.0636	0.059*
C11	0.0905 (7)	0.5306 (5)	−0.1200 (3)	0.0478 (10)
H11	0.0157	0.6287	−0.1449	0.057*
C12	0.0637 (6)	0.3839 (5)	−0.1299 (3)	0.0426 (9)
C13	0.1798 (6)	0.2402 (5)	−0.0936 (3)	0.0419 (9)
H13	0.1613	0.1421	−0.1005	0.050*
C14	−0.1028 (7)	0.3743 (6)	−0.1700 (3)	0.0468 (10)
C15	0.0391 (10)	0.4689 (8)	−0.3107 (3)	0.0732 (16)
H15A	0.1301	0.4851	−0.2785	0.088*
H15B	−0.0288	0.5745	−0.3370	0.088*
C16	0.1577 (13)	0.3470 (13)	−0.3789 (6)	0.136 (4)
H16A	0.2601	0.3820	−0.4123	0.203*
H16B	0.0709	0.3392	−0.4151	0.203*
H16C	0.2193	0.2404	−0.3536	0.203*
C17	−0.2911 (10)	0.4212 (8)	−0.2844 (4)	0.0754 (16)
H17A	−0.4114	0.4706	−0.2420	0.090*
H17B	−0.3049	0.4888	−0.3359	0.090*
C18	−0.2719 (12)	0.2533 (8)	−0.3035 (5)	0.097 (2)
H18A	−0.3828	0.2589	−0.3290	0.146*
H18B	−0.2721	0.1894	−0.2515	0.146*
H18C	−0.1483	0.2014	−0.3424	0.146*

	U11	U22	U33	U12	U13	U23
Co1	0.0376 (5)	0.0409 (5)	0.0385 (5)	−0.0145 (3)	−0.0104 (3)	0.0022 (3)
O1	0.0497 (17)	0.0557 (18)	0.0396 (16)	−0.0214 (15)	−0.0118 (13)	0.0004 (13)
O2	0.0445 (18)	0.069 (2)	0.0525 (18)	−0.0191 (16)	−0.0098 (14)	−0.0061 (16)
O3	0.100 (3)	0.148 (5)	0.068 (3)	−0.070 (3)	−0.032 (2)	0.002 (3)
O4	0.0547 (19)	0.070 (2)	0.062 (2)	−0.0353 (18)	−0.0136 (16)	0.0081 (17)
O5	0.0472 (18)	0.059 (2)	0.0508 (18)	−0.0255 (16)	−0.0102 (14)	0.0031 (15)
N1	0.0381 (18)	0.0404 (19)	0.049 (2)	−0.0148 (15)	−0.0127 (15)	0.0019 (15)
N2	0.065 (3)	0.077 (3)	0.054 (2)	−0.036 (2)	−0.023 (2)	0.010 (2)
C1	0.043 (2)	0.038 (2)	0.044 (2)	−0.0119 (18)	−0.0106 (18)	−0.0002 (17)
C2	0.044 (2)	0.039 (2)	0.041 (2)	−0.0131 (18)	−0.0086 (17)	0.0002 (17)
C3	0.044 (2)	0.055 (3)	0.049 (2)	−0.018 (2)	−0.0040 (19)	−0.001 (2)
C4	0.065 (3)	0.071 (3)	0.037 (2)	−0.028 (3)	−0.006 (2)	−0.001 (2)
C5	0.061 (3)	0.062 (3)	0.045 (2)	−0.026 (2)	−0.014 (2)	0.000 (2)
C6	0.049 (3)	0.061 (3)	0.048 (3)	−0.025 (2)	−0.012 (2)	0.001 (2)
C7	0.047 (2)	0.050 (2)	0.041 (2)	−0.020 (2)	−0.0047 (18)	0.0025 (18)
C8	0.083 (4)	0.106 (5)	0.050 (3)	−0.046 (4)	−0.017 (3)	−0.003 (3)
C9	0.041 (2)	0.047 (2)	0.048 (2)	−0.0174 (19)	−0.0145 (18)	0.0010 (18)
C10	0.054 (3)	0.044 (2)	0.056 (3)	−0.023 (2)	−0.013 (2)	0.003 (2)
C11	0.049 (2)	0.041 (2)	0.051 (3)	−0.016 (2)	−0.011 (2)	0.0079 (19)
C12	0.041 (2)	0.049 (2)	0.038 (2)	−0.0166 (19)	−0.0089 (17)	0.0038 (18)
C13	0.042 (2)	0.041 (2)	0.044 (2)	−0.0156 (18)	−0.0107 (17)	0.0020 (17)
C14	0.044 (2)	0.049 (3)	0.049 (2)	−0.018 (2)	−0.0126 (19)	0.0054 (19)
C15	0.087 (4)	0.084 (4)	0.057 (3)	−0.040 (3)	−0.015 (3)	0.005 (3)
C16	0.109 (6)	0.178 (9)	0.122 (7)	−0.066 (7)	0.029 (5)	−0.069 (7)
C17	0.082 (4)	0.075 (4)	0.080 (4)	−0.032 (3)	−0.040 (3)	0.017 (3)
C18	0.134 (7)	0.086 (5)	0.088 (5)	−0.046 (5)	−0.049 (5)	−0.001 (4)

Co1—O1	2.088 (3)	C7—C6	1.370 (6)
Co1—O1i	2.088 (3)	C7—H7	0.9300
Co1—O5	2.121 (3)	C8—H81	1.04 (6)
Co1—O5i	2.121 (3)	C9—H9	0.9300
Co1—N1	2.163 (3)	C10—C9	1.377 (6)
Co1—N1i	2.163 (3)	C10—C11	1.385 (6)
O1—C1	1.262 (5)	C10—H10	0.9300
O2—C1	1.257 (5)	C11—H11	0.9300
O3—C8	1.193 (7)	C12—C11	1.385 (6)
O4—C14	1.219 (5)	C12—C13	1.378 (6)
O5—H51	0.94 (4)	C13—H13	0.9300
O5—H52	0.92 (2)	C14—N2	1.330 (6)
N1—C9	1.341 (5)	C14—C12	1.511 (6)
N1—C13	1.343 (5)	C15—C16	1.476 (9)
N2—C15	1.473 (7)	C15—H15A	0.9700
N2—C17	1.501 (7)	C15—H15B	0.9700
C2—C1	1.504 (6)	C16—H16A	0.9600
C2—C3	1.391 (6)	C16—H16B	0.9600
C2—C7	1.392 (6)	C16—H16C	0.9600
C3—C4	1.371 (6)	C17—C18	1.463 (8)
C3—H3	0.9300	C17—H17A	0.9700
C4—C5	1.394 (7)	C17—H17B	0.9700
C4—H4	0.9300	C18—H18A	0.9600
C5—C6	1.391 (6)	C18—H18B	0.9600
C5—C8	1.477 (7)	C18—H18C	0.9600
C6—H6	0.9300
O1i—Co1—O1	180.00 (17)	O3—C8—C5	126.1 (6)
O1i—Co1—O5i	88.16 (12)	O3—C8—H81	116 (3)
O1—Co1—O5i	91.84 (12)	C5—C8—H81	117 (3)
O1i—Co1—O5	91.84 (12)	N1—C9—C10	123.3 (4)
O1—Co1—O5	88.16 (12)	N1—C9—H9	118.3
O1i—Co1—N1	91.25 (12)	C10—C9—H9	118.3
O1—Co1—N1	88.75 (12)	C9—C10—C11	118.5 (4)
O1i—Co1—N1i	88.75 (12)	C9—C10—H10	120.7
O1—Co1—N1i	91.25 (12)	C11—C10—H10	120.7
O5i—Co1—O5	180.00 (18)	C10—C11—H11	120.6
O5i—Co1—N1	93.36 (12)	C12—C11—C10	118.8 (4)
O5—Co1—N1	86.64 (12)	C12—C11—H11	120.6
O5i—Co1—N1i	86.64 (12)	C11—C12—C14	123.6 (4)
O5—Co1—N1i	93.36 (12)	C13—C12—C11	119.1 (4)
N1—Co1—N1i	180.0 (2)	C13—C12—C14	116.9 (4)
C1—O1—Co1	127.5 (3)	N1—C13—C12	122.6 (4)
Co1—O5—H51	119 (4)	N1—C13—H13	118.7
Co1—O5—H52	97 (3)	C12—C13—H13	118.7
H52—O5—H51	105 (3)	O4—C14—N2	122.1 (4)
C9—N1—Co1	123.6 (3)	O4—C14—C12	117.9 (4)
C9—N1—C13	117.7 (4)	N2—C14—C12	120.0 (4)
C13—N1—Co1	118.6 (3)	N2—C15—C16	113.8 (6)
C14—N2—C15	125.4 (4)	N2—C15—H15A	108.8
C14—N2—C17	116.9 (4)	N2—C15—H15B	108.8
C15—N2—C17	117.6 (4)	C16—C15—H15A	108.8
O1—C1—C2	116.9 (4)	C16—C15—H15B	108.8
O2—C1—O1	125.1 (4)	H15A—C15—H15B	107.7
O2—C1—C2	118.0 (4)	C15—C16—H16A	109.5
C3—C2—C1	120.0 (4)	C15—C16—H16B	109.5
C3—C2—C7	118.7 (4)	C15—C16—H16C	109.5
C7—C2—C1	121.3 (4)	H16A—C16—H16B	109.5
C2—C3—H3	119.9	H16A—C16—H16C	109.5
C4—C3—C2	120.3 (4)	H16B—C16—H16C	109.5
C4—C3—H3	119.9	N2—C17—H17A	109.4
C3—C4—C5	120.5 (4)	N2—C17—H17B	109.4
C3—C4—H4	119.7	C18—C17—N2	111.3 (5)
C5—C4—H4	119.7	C18—C17—H17A	109.4
C4—C5—C8	119.7 (5)	C18—C17—H17B	109.4
C6—C5—C4	119.5 (4)	H17A—C17—H17B	108.0
C6—C5—C8	120.7 (5)	C17—C18—H18A	109.5
C5—C6—H6	120.2	C17—C18—H18B	109.5
C7—C6—C5	119.5 (4)	C17—C18—H18C	109.5
C7—C6—H6	120.2	H18A—C18—H18B	109.5
C2—C7—H7	119.3	H18A—C18—H18C	109.5
C6—C7—C2	121.4 (4)	H18B—C18—H18C	109.5
C6—C7—H7	119.3
O5i—Co1—O1—C1	−11.3 (4)	C1—C2—C3—C4	179.5 (4)
O5—Co1—O1—C1	168.7 (4)	C7—C2—C3—C4	−1.1 (7)
N1—Co1—O1—C1	82.0 (4)	C1—C2—C7—C6	−178.9 (4)
N1i—Co1—O1—C1	−98.0 (4)	C3—C2—C7—C6	1.8 (7)
O1i—Co1—N1—C9	33.5 (3)	C2—C3—C4—C5	−0.3 (7)
O1—Co1—N1—C9	−146.5 (3)	C3—C4—C5—C6	1.2 (8)
O1i—Co1—N1—C13	−148.7 (3)	C3—C4—C5—C8	−179.0 (5)
O1—Co1—N1—C13	31.3 (3)	C4—C5—C6—C7	−0.6 (8)
O5i—Co1—N1—C9	−54.7 (3)	C8—C5—C6—C7	179.6 (5)
O5—Co1—N1—C9	125.3 (3)	C4—C5—C8—O3	174.2 (7)
O5i—Co1—N1—C13	123.0 (3)	C6—C5—C8—O3	−6.0 (10)
O5—Co1—N1—C13	−57.0 (3)	C2—C7—C6—C5	−1.0 (7)
Co1—O1—C1—O2	27.6 (6)	C11—C10—C9—N1	−0.6 (7)
Co1—O1—C1—C2	−151.1 (3)	C9—C10—C11—C12	1.5 (7)
Co1—N1—C9—C10	177.3 (3)	C13—C12—C11—C10	−1.2 (6)
C13—N1—C9—C10	−0.5 (6)	C14—C12—C11—C10	171.5 (4)
Co1—N1—C13—C12	−177.2 (3)	C11—C12—C13—N1	0.1 (6)
C9—N1—C13—C12	0.7 (6)	C14—C12—C13—N1	−173.1 (4)
C14—N2—C15—C16	109.8 (7)	O4—C14—C12—C11	−114.3 (5)
C17—N2—C15—C16	−70.5 (8)	O4—C14—C12—C13	58.6 (6)
C14—N2—C17—C18	−77.7 (7)	N2—C14—C12—C11	62.5 (6)
C15—N2—C17—C18	102.6 (6)	N2—C14—C12—C13	−124.6 (5)
C3—C2—C1—O1	175.2 (4)	O4—C14—N2—C15	−178.4 (5)
C3—C2—C1—O2	−3.6 (6)	O4—C14—N2—C17	1.9 (7)
C7—C2—C1—O1	−4.1 (6)	C12—C14—N2—C15	5.0 (8)
C7—C2—C1—O2	177.1 (4)	C12—C14—N2—C17	−174.7 (4)

D—H···A	D—H	H···A	D···A	D—H···A
O5—H51···O4ii	0.94 (4)	1.86 (4)	2.787 (5)	174 (6)
O5—H52···O2i	0.92 (2)	1.73 (4)	2.646 (5)	168 (6)

Table 1

Selected bond lengths (Å)

Co1—O1	2.088 (3)
Co1—O5	2.121 (3)
Co1—N1	2.163 (3)

Table 2

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H51⋯O4i	0.94 (4)	1.86 (4)	2.787 (5)	174 (6)
O5—H52⋯O2ii	0.92 (2)	1.73 (4)	2.646 (5)	168 (6)

Symmetry codes: (i) ; (ii) .