{2,2′-[6,6′-Dimethoxy­cyclo­hexane-1,2-diylbis(nitrilo­methyl­idyne)]diphenolato-κ4O1,N,N′,O1′}cobalt(II) monohydrate

Bao, Y.; Li, H.-F.; Yan, P.-F.; Li, G.-M.; Hou, G.-F.

doi:10.1107/S1600536809021540

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 7| July 2009| Page m770

doi:10.1107/S1600536809021540

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{2,2′-[6,6′-Dimethoxycyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato-κ⁴O¹,N,N′,O^1′}cobalt(II) monohydrate

Yan Bao,^a Hong-Feng Li,^a Peng-Fei Yan,^a Guang-Ming Li ^a ^* and Guang-Feng Hou ^a

^aKey Laboratory of Functional Inorganic Material Chemistry (Heilongjiang University), Ministry of Education, School of Chemistry and Materials Science, Heilongjiang University, Harbin 150080, People's Republic of China
^*Correspondence e-mail: gmli@hlju.edu.cn

(Received 23 December 2008; accepted 6 June 2009; online 13 June 2009)

In the title complex, [Co(C₂₂H₂₄N₂O₄)]·H₂O, the Co^II atom is in an almost square-planar coordination environment involving two O and two N atoms from the Schiff base ligand. A water molecule cocrystallizes with the coordination compound and may be held in the crystal by O—H⋯O hydrogen bonds. Heteroatomic π–π ring interactions may be present between symmetry-related complexes, with centroid–centroid distances of 3.5661 (8) Å.

Related literature

For related platinum complexes of a similar Schiff base, see: Lu et al. (2008 ).

Experimental

Crystal data

[Co(C₂₂H₂₄N₂O₄)]·H₂O
M_r = 457.38
Monoclinic, P 2₁ /n
a = 11.241 (3) Å
b = 10.605 (3) Å
c = 17.864 (7) Å
β = 107.158 (14)°
V = 2034.9 (12) Å³
Z = 4
Mo Kα radiation
μ = 0.88 mm⁻¹
T = 291 K
0.20 × 0.19 × 0.17 mm

Data collection

Rigaku R-AXIS RAPID diffractometer
Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ) T_min = 0.826, T_max = 0.851
19221 measured reflections
4647 independent reflections
3840 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.029
wR(F²) = 0.069
S = 1.04
4647 reflections
373 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.36 e Å⁻³
Δρ_min = −0.24 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H25⋯O2	0.90 (4)	2.11 (4)	2.916 (3)	149 (3)
O5—H25⋯O1	0.90 (4)	2.45 (4)	3.103 (2)	129 (3)
O5—H26⋯O4	0.89 (4)	2.05 (4)	2.895 (3)	159 (4)
O5—H26⋯O3	0.89 (4)	2.59 (4)	3.248 (2)	131 (3)

Data collection: RAPID-AUTO (Rigaku, 1998 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809021540/cs2106sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809021540/cs2106Isup2.hkl

checkCIF report

Comment top

As shown in Fig. 1, Co^II is four-coordinated in a square planar environment as the ligating Schiff base is a tetradentate ligand (Table 1). The co-crystallized water molecule does not coordinate to the Co ion. Its position is stabilized by bifurcated O—H···O hydrogen bonds (Table 2). It is also worth noting that stabilizing π–π ring interactions may occur between symmetry center related phenyl C1 -> C6 and C7 -> O1 heteroatomic rings, as show in Fig. 2. The π–π center to center distance is 3.5661 (8) Å. Together with an almost perfect rings-to-rings matching this may indicate appreciable interactions.

Related literature top

For related platinum complexes of a similar Schiff base, see: Lu et al. (2008).

Experimental top

The title complex was obtained by the treatment of cobalt(II) acetate tetrahydrate with the neutral Schiff base in methanol/acetone (1:2). The yellow clear mixture turned to salmon pink precipitation after stirred for 4 h; diethyl ether was allowed to diffuse slowly into the solution of the filtrate. Red single crystals were obtained after several days.Analysis calculated for C₂₂H₂₆Co_N2_O5: C, 57.77; H, 5.73; N, 6.12; Co, 12.88; found: C, 57.56; H, 5.23; N, 6.77; Co, 12.79%.

Computing details top

Data collection: RAPID-AUTO (Rigaku, 1998); cell refinement: RAPID-AUTO (Rigaku, 1998); data reduction: RAPID-AUTO (Rigaku, 1998); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, showing 30% probability displacement ellipsoids for non-H atoms. Dashed lines indicate the hydrogen-bonding interactions between the water and the host.
	Fig. 2. Heteroatomic π–π ring interactions across an inversion center, indicated by broken lines.

{2,2'-[6,6'-Dimethoxycyclohexane-1,2-diylbis(nitrilomethylidyne)]diphenolato- κ⁴O¹,N,N',O^1'}cobalt(II) monohydrate top

Crystal data top

[Co(C₂₂H₂₄N₂O₄)]·H₂O	F(000) = 956
M_r = 457.38	D_x = 1.493 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 15295 reflections
a = 11.241 (3) Å	θ = 3.1–27.5°
b = 10.605 (3) Å	µ = 0.88 mm⁻¹
c = 17.864 (7) Å	T = 291 K
β = 107.158 (14)°	Block, red
V = 2034.9 (12) Å³	0.20 × 0.19 × 0.17 mm
Z = 4

Data collection top

Rigaku R-AXIS RAPID diffractometer	4647 independent reflections
Radiation source: fine-focus sealed tube	3840 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
ω scans	θ_max = 27.5°, θ_min = 3.1°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −14→14
T_min = 0.826, T_max = 0.851	k = −11→13
19221 measured reflections	l = −23→23

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)] = 0.029	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0317P)² + 0.4P] where P = (F_o² + 2F_c²)/3
4647 reflections	(Δ/σ)_max = 0.001
373 parameters	Δρ_max = 0.36 e Å⁻³
0 restraints	Δρ_min = −0.24 e Å⁻³

Crystal data top

[Co(C₂₂H₂₄N₂O₄)]·H₂O	V = 2034.9 (12) Å³
M_r = 457.38	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.241 (3) Å	µ = 0.88 mm⁻¹
b = 10.605 (3) Å	T = 291 K
c = 17.864 (7) Å	0.20 × 0.19 × 0.17 mm
β = 107.158 (14)°

Data collection top

Rigaku R-AXIS RAPID diffractometer	4647 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3840 reflections with I > 2σ(I)
T_min = 0.826, T_max = 0.851	R_int = 0.034
19221 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.029	0 restraints
wR(F²) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.36 e Å⁻³
4647 reflections	Δρ_min = −0.24 e Å⁻³
373 parameters

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

	x	y	z	U_iso*/U_eq
C1	0.55207 (14)	0.17711 (15)	0.02619 (9)	0.0336 (3)
C2	0.47583 (15)	0.27964 (16)	−0.01173 (10)	0.0397 (4)
C3	0.46233 (17)	0.30829 (18)	−0.08877 (11)	0.0450 (4)
C4	0.52295 (17)	0.23721 (19)	−0.13239 (11)	0.0476 (4)
C5	0.59830 (16)	0.13964 (19)	−0.09779 (10)	0.0427 (4)
C6	0.61536 (14)	0.10945 (15)	−0.01824 (9)	0.0336 (3)
C7	0.69932 (14)	0.00941 (16)	0.01550 (10)	0.0346 (3)
C8	0.81705 (14)	−0.13254 (16)	0.11525 (10)	0.0349 (3)
C9	0.91820 (16)	−0.1510 (2)	0.07467 (11)	0.0448 (4)
C10	1.01669 (18)	−0.0482 (2)	0.09542 (13)	0.0548 (5)
C11	1.07198 (18)	−0.0338 (3)	0.18328 (13)	0.0588 (6)
C12	0.97012 (17)	−0.0087 (2)	0.22218 (12)	0.0462 (4)
C13	0.87250 (15)	−0.11292 (17)	0.20283 (10)	0.0364 (4)
C14	0.75527 (16)	−0.12574 (16)	0.29443 (10)	0.0385 (4)
C15	0.65495 (15)	−0.09883 (17)	0.32630 (10)	0.0386 (4)
C16	0.6452 (2)	−0.1711 (2)	0.39057 (12)	0.0509 (5)
C17	0.5519 (2)	−0.1499 (2)	0.42283 (13)	0.0629 (6)
C18	0.4652 (2)	−0.0550 (2)	0.39271 (13)	0.0602 (6)
C19	0.47299 (17)	0.01755 (19)	0.33093 (11)	0.0447 (4)
C20	0.56884 (15)	−0.00204 (16)	0.29425 (10)	0.0365 (4)
C21	0.2944 (2)	0.1401 (3)	0.33174 (16)	0.0633 (6)
C22	0.3317 (2)	0.4392 (2)	0.00145 (17)	0.0610 (6)
N1	0.73023 (11)	−0.02450 (13)	0.08792 (8)	0.0322 (3)
N2	0.76520 (12)	−0.07817 (13)	0.23028 (8)	0.0351 (3)
Co1	0.656300 (17)	0.030194 (19)	0.162807 (12)	0.02751 (7)
O1	0.55821 (10)	0.15217 (11)	0.09913 (7)	0.0371 (3)
O2	0.42054 (14)	0.34365 (13)	0.03579 (9)	0.0586 (4)
O3	0.57104 (11)	0.06922 (11)	0.23491 (7)	0.0400 (3)
O4	0.39176 (12)	0.11321 (15)	0.29806 (8)	0.0559 (4)
O5	0.30979 (18)	0.1993 (3)	0.13719 (12)	0.0994 (7)
H25	0.370 (4)	0.239 (4)	0.122 (2)	0.149*
H26	0.354 (4)	0.176 (4)	0.185 (2)	0.149*
H5	0.7650 (15)	−0.2112 (17)	0.1078 (10)	0.034 (4)*
H4	0.7370 (17)	−0.0353 (16)	−0.0216 (11)	0.042 (5)*
H15	0.8198 (16)	−0.1865 (17)	0.3229 (10)	0.038 (5)*
H14	0.9086 (16)	−0.1919 (17)	0.2269 (11)	0.039 (5)*
H6	0.8798 (17)	−0.1612 (17)	0.0162 (12)	0.047 (5)*
H1	0.4088 (17)	0.3782 (18)	−0.1147 (11)	0.047 (5)*
H13	0.9278 (18)	0.077 (2)	0.2029 (12)	0.053 (6)*
H12	1.0042 (19)	−0.0036 (18)	0.2804 (13)	0.051 (6)*
H2	0.5101 (18)	0.2573 (19)	−0.1860 (13)	0.057 (6)*
H23	0.261 (2)	0.402 (2)	−0.0407 (14)	0.062 (6)*
H16	0.704 (2)	−0.237 (2)	0.4099 (13)	0.060 (6)*
H3	0.6401 (19)	0.087 (2)	−0.1280 (12)	0.058 (6)*
H7	0.9564 (18)	−0.235 (2)	0.0946 (12)	0.054 (6)*
H9	0.978 (2)	0.038 (2)	0.0714 (14)	0.065 (7)*
H19	0.329 (2)	0.168 (2)	0.3868 (16)	0.077 (7)*
H18	0.396 (2)	−0.039 (2)	0.4151 (15)	0.079 (8)*
H11	1.132 (2)	0.044 (2)	0.1943 (14)	0.071 (7)*
H17	0.541 (2)	−0.207 (2)	0.4636 (15)	0.078 (7)*
H20	0.247 (2)	0.060 (2)	0.3337 (14)	0.068 (7)*
H22	0.301 (2)	0.471 (2)	0.0463 (17)	0.087 (9)*
H8	1.082 (2)	−0.065 (2)	0.0701 (13)	0.063 (6)*
H10	1.116 (2)	−0.111 (2)	0.2077 (14)	0.064 (7)*
H24	0.368 (2)	0.504 (3)	−0.0252 (16)	0.087 (9)*
H21	0.245 (2)	0.210 (2)	0.2927 (16)	0.083 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0289 (7)	0.0366 (8)	0.0335 (9)	−0.0053 (6)	0.0065 (6)	0.0020 (7)
C2	0.0366 (8)	0.0387 (9)	0.0430 (10)	−0.0011 (7)	0.0104 (7)	0.0043 (8)
C3	0.0400 (9)	0.0438 (10)	0.0466 (11)	−0.0021 (8)	0.0054 (8)	0.0121 (8)
C4	0.0482 (10)	0.0565 (12)	0.0349 (10)	−0.0083 (9)	0.0072 (8)	0.0100 (9)
C5	0.0422 (9)	0.0514 (11)	0.0341 (9)	−0.0054 (8)	0.0105 (8)	−0.0002 (8)
C6	0.0292 (7)	0.0386 (9)	0.0319 (8)	−0.0049 (7)	0.0074 (6)	0.0008 (7)
C7	0.0323 (7)	0.0409 (9)	0.0315 (8)	−0.0029 (7)	0.0110 (7)	−0.0045 (7)
C8	0.0307 (7)	0.0358 (9)	0.0381 (9)	0.0020 (7)	0.0099 (7)	−0.0035 (7)
C9	0.0385 (9)	0.0572 (12)	0.0393 (10)	0.0107 (8)	0.0125 (8)	−0.0032 (9)
C10	0.0384 (9)	0.0813 (16)	0.0489 (12)	−0.0047 (10)	0.0194 (9)	0.0004 (11)
C11	0.0355 (9)	0.0888 (17)	0.0521 (13)	−0.0097 (11)	0.0130 (9)	−0.0079 (12)
C12	0.0381 (9)	0.0593 (12)	0.0386 (10)	−0.0060 (8)	0.0075 (8)	−0.0066 (9)
C13	0.0319 (8)	0.0415 (9)	0.0360 (9)	0.0060 (7)	0.0105 (7)	0.0040 (7)
C14	0.0409 (9)	0.0395 (9)	0.0337 (9)	0.0009 (7)	0.0092 (7)	0.0034 (7)
C15	0.0404 (8)	0.0454 (10)	0.0303 (8)	−0.0045 (8)	0.0111 (7)	−0.0004 (7)
C16	0.0575 (11)	0.0561 (12)	0.0401 (11)	−0.0021 (10)	0.0162 (9)	0.0087 (9)
C17	0.0711 (14)	0.0784 (16)	0.0467 (12)	−0.0038 (12)	0.0292 (11)	0.0157 (11)
C18	0.0566 (12)	0.0860 (17)	0.0480 (12)	−0.0035 (11)	0.0309 (10)	0.0033 (11)
C19	0.0411 (9)	0.0589 (11)	0.0367 (9)	−0.0019 (8)	0.0157 (8)	−0.0045 (8)
C20	0.0385 (8)	0.0438 (9)	0.0280 (8)	−0.0046 (7)	0.0109 (7)	−0.0039 (7)
C21	0.0442 (11)	0.0938 (19)	0.0601 (15)	−0.0018 (13)	0.0281 (11)	−0.0154 (14)
C22	0.0524 (12)	0.0483 (12)	0.0757 (17)	0.0146 (10)	0.0088 (12)	0.0001 (12)
N1	0.0286 (6)	0.0357 (7)	0.0324 (7)	−0.0002 (6)	0.0091 (5)	−0.0018 (6)
N2	0.0345 (7)	0.0380 (7)	0.0335 (7)	0.0013 (6)	0.0112 (6)	0.0013 (6)
Co1	0.02730 (10)	0.03082 (12)	0.02579 (11)	0.00243 (8)	0.00995 (8)	0.00088 (8)
O1	0.0373 (6)	0.0411 (6)	0.0344 (6)	0.0063 (5)	0.0128 (5)	0.0035 (5)
O2	0.0652 (8)	0.0561 (8)	0.0584 (9)	0.0267 (7)	0.0244 (7)	0.0140 (7)
O3	0.0448 (6)	0.0445 (7)	0.0350 (6)	0.0063 (5)	0.0186 (5)	0.0036 (5)
O4	0.0476 (7)	0.0772 (10)	0.0513 (8)	0.0127 (7)	0.0277 (6)	0.0003 (7)
O5	0.0700 (12)	0.161 (2)	0.0736 (13)	0.0206 (13)	0.0315 (10)	0.0263 (14)

Geometric parameters (Å, º) top

C1—O1	1.3112 (19)	C13—N2	1.477 (2)
C1—C6	1.409 (2)	C13—H14	0.974 (18)
C1—C2	1.426 (2)	C14—N2	1.287 (2)
C2—O2	1.371 (2)	C14—C15	1.434 (2)
C2—C3	1.373 (3)	C14—H15	0.991 (18)
C3—C4	1.398 (3)	C15—C20	1.411 (2)
C3—H1	0.980 (19)	C15—C16	1.411 (2)
C4—C5	1.364 (3)	C16—C17	1.356 (3)
C4—H2	0.95 (2)	C16—H16	0.96 (2)
C5—C6	1.413 (2)	C17—C18	1.394 (3)
C5—H3	0.99 (2)	C17—H17	0.98 (2)
C6—C7	1.430 (2)	C18—C19	1.369 (3)
C7—N1	1.288 (2)	C18—H18	0.99 (3)
C7—H4	1.005 (19)	C19—O4	1.375 (2)
C8—N1	1.491 (2)	C19—C20	1.432 (2)
C8—C13	1.518 (2)	C20—O3	1.308 (2)
C8—C9	1.531 (2)	C21—O4	1.425 (2)
C8—H5	1.005 (17)	C21—H19	0.99 (3)
C9—C10	1.519 (3)	C21—H20	1.01 (2)
C9—H6	1.01 (2)	C21—H21	1.06 (3)
C9—H7	1.01 (2)	C22—O2	1.427 (2)
C10—C11	1.516 (3)	C22—H23	1.00 (2)
C10—H9	1.05 (2)	C22—H22	1.02 (3)
C10—H8	0.98 (2)	C22—H24	0.99 (3)
C11—C12	1.528 (3)	N1—Co1	1.8635 (14)
C11—H11	1.04 (2)	N2—Co1	1.8443 (14)
C11—H10	0.99 (2)	Co1—O1	1.8556 (12)
C12—C13	1.524 (3)	Co1—O3	1.8647 (12)
C12—H13	1.04 (2)	O5—H25	0.90 (4)
C12—H12	1.00 (2)	O5—H26	0.89 (4)

O1—C1—C6	124.74 (15)	N2—C13—H14	110.1 (10)
O1—C1—C2	118.30 (15)	C8—C13—H14	109.1 (11)
C6—C1—C2	116.96 (15)	C12—C13—H14	110.2 (10)
O2—C2—C3	125.08 (16)	N2—C14—C15	124.09 (16)
O2—C2—C1	113.72 (15)	N2—C14—H15	118.0 (10)
C3—C2—C1	121.20 (16)	C15—C14—H15	117.9 (10)
C2—C3—C4	120.77 (17)	C20—C15—C16	121.09 (16)
C2—C3—H1	120.7 (11)	C20—C15—C14	120.62 (15)
C4—C3—H1	118.5 (11)	C16—C15—C14	118.29 (17)
C5—C4—C3	119.74 (18)	C17—C16—C15	120.7 (2)
C5—C4—H2	121.1 (12)	C17—C16—H16	120.3 (13)
C3—C4—H2	119.2 (12)	C15—C16—H16	118.9 (13)
C4—C5—C6	120.62 (17)	C16—C17—C18	119.7 (2)
C4—C5—H3	121.0 (12)	C16—C17—H17	119.7 (14)
C6—C5—H3	118.3 (12)	C18—C17—H17	120.3 (14)
C1—C6—C5	120.65 (16)	C19—C18—C17	120.92 (18)
C1—C6—C7	121.38 (15)	C19—C18—H18	118.5 (15)
C5—C6—C7	117.96 (15)	C17—C18—H18	120.6 (14)
N1—C7—C6	125.43 (15)	C18—C19—O4	124.51 (17)
N1—C7—H4	119.3 (11)	C18—C19—C20	121.53 (19)
C6—C7—H4	115.2 (11)	O4—C19—C20	113.96 (16)
N1—C8—C13	105.21 (13)	O3—C20—C15	125.06 (14)
N1—C8—C9	116.68 (14)	O3—C20—C19	118.93 (16)
C13—C8—C9	111.66 (14)	C15—C20—C19	116.01 (15)
N1—C8—H5	107.2 (9)	O4—C21—H19	110.8 (14)
C13—C8—H5	107.2 (10)	O4—C21—H20	108.8 (13)
C9—C8—H5	108.5 (9)	H19—C21—H20	105.9 (19)
C10—C9—C8	112.49 (16)	O4—C21—H21	100.6 (14)
C10—C9—H6	112.8 (11)	H19—C21—H21	115 (2)
C8—C9—H6	110.6 (10)	H20—C21—H21	115.9 (19)
C10—C9—H7	110.1 (11)	O2—C22—H23	109.8 (13)
C8—C9—H7	104.1 (11)	O2—C22—H22	104.5 (15)
H6—C9—H7	106.1 (16)	H23—C22—H22	110.4 (19)
C11—C10—C9	111.82 (18)	O2—C22—H24	111.5 (15)
C11—C10—H9	109.3 (13)	H23—C22—H24	105 (2)
C9—C10—H9	110.1 (12)	H22—C22—H24	116 (2)
C11—C10—H8	111.3 (13)	C7—N1—C8	120.01 (13)
C9—C10—H8	110.0 (13)	C7—N1—Co1	126.08 (11)
H9—C10—H8	104.2 (17)	C8—N1—Co1	113.06 (10)
C10—C11—C12	110.80 (17)	C14—N2—C13	119.46 (14)
C10—C11—H11	108.6 (13)	C14—N2—Co1	127.67 (12)
C12—C11—H11	108.0 (13)	C13—N2—Co1	112.85 (11)
C10—C11—H10	111.9 (14)	N2—Co1—O1	174.19 (6)
C12—C11—H10	106.9 (13)	N2—Co1—N1	85.67 (6)
H11—C11—H10	110.6 (18)	O1—Co1—N1	95.00 (6)
C13—C12—C11	110.88 (17)	N2—Co1—O3	93.68 (6)
C13—C12—H13	109.3 (11)	O1—Co1—O3	86.28 (5)
C11—C12—H13	109.5 (11)	N1—Co1—O3	173.66 (5)
C13—C12—H12	107.7 (11)	C1—O1—Co1	126.68 (10)
C11—C12—H12	112.0 (12)	C2—O2—C22	118.21 (17)
H13—C12—H12	107.3 (16)	C20—O3—Co1	124.61 (11)
N2—C13—C8	104.42 (13)	C19—O4—C21	117.60 (18)
N2—C13—C12	110.35 (14)	H25—O5—H26	99 (3)
C8—C13—C12	112.49 (15)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H25···O2	0.90 (4)	2.11 (4)	2.916 (3)	149 (3)
O5—H25···O1	0.90 (4)	2.45 (4)	3.103 (2)	129 (3)
O5—H26···O4	0.89 (4)	2.05 (4)	2.895 (3)	159 (4)
O5—H26···O3	0.89 (4)	2.59 (4)	3.248 (2)	131 (3)

Experimental details

Crystal data
Chemical formula	[Co(C₂₂H₂₄N₂O₄)]·H₂O
M_r	457.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	291
a, b, c (Å)	11.241 (3), 10.605 (3), 17.864 (7)
β (°)	107.158 (14)
V (Å³)	2034.9 (12)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.88
Crystal size (mm)	0.20 × 0.19 × 0.17

Data collection
Diffractometer	Rigaku R-AXIS RAPID diffractometer
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.826, 0.851
No. of measured, independent and observed [I > 2σ(I)] reflections	19221, 4647, 3840
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.069, 1.04
No. of reflections	4647
No. of parameters	373
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.24

Computer programs: RAPID-AUTO (Rigaku, 1998), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H25···O2	0.90 (4)	2.11 (4)	2.916 (3)	149 (3)
O5—H25···O1	0.90 (4)	2.45 (4)	3.103 (2)	129 (3)
O5—H26···O4	0.89 (4)	2.05 (4)	2.895 (3)	159 (4)
O5—H26···O3	0.89 (4)	2.59 (4)	3.248 (2)	131 (3)

Acknowledgements

The authors gratefully acknowledge financial support from the National Natural Science Foundation of China (grant Nos. 20572018 and 20672032), Heilongjiang Province (grant Nos. 1055HZ001, ZJG0504 and JC200605) and Heilongjiang University.

References

Higashi, T. (1995). ABSCOR. Rigaku Corporation, Tokyo, Japan. Google Scholar
Lu, X. P., Wong, W. Y. & Wong, W. K. (2008). J. Eur. Inorg. Chem. pp. 523-–528. Google Scholar
Rigaku (1998). RAPID-AUTO. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar

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