(5-Amino­isophthalato-κN)triaqua­(1,10-phenanthroline-κ2N,N′)cobalt(II) trihydrate

Zhang, K.-L.; Diao, G.-W.; Ng, S.W.

doi:10.1107/S1600536810040560

metal-organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page m1421

https://doi.org/10.1107/S1600536810040560

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(5-Aminoisophthalato-κN)triaqua(1,10-phenanthroline-κ²N,N′)cobalt(II) trihydrate

Kou-Lin Zhang,^a Guo-Wang Diao ^a and Seik Weng Ng ^b ^*

^aCollege of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 7 October 2010; accepted 10 October 2010; online 20 October 2010)

The Co^II atom in the title compound, [Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O, is six-coordinated in a CoN₃O₃ octahedral geometry; the water-coordinated Co^II atom is chelated by the N-heterocycle. An intermolecular N—H⋯O hydrogen bond occurs. The carboxylate entity coordinates through the amino group. The carboxylate donor unit, coordinated and uncoordinated water molecules interact through O—H⋯O and N—H⋯O hydrogen bonds, generating a tightly-held three-dimensional cage-like network.

Related literature

For related structures, see: He et al. (2006 ); Wu et al. (2002a ,b ).

Experimental

Crystal data

[Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O
M_r = 526.36
Monoclinic, P 2₁ /n
a = 10.1182 (2) Å
b = 13.9659 (2) Å
c = 16.2850 (2) Å
β = 95.827 (1)°
V = 2289.34 (8) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 293 K
0.24 × 0.22 × 0.18 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.803, T_max = 1.000
18954 measured reflections
5683 independent reflections
5120 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.086
S = 1.04
5683 reflections
363 parameters
14 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1w—H1w1⋯O6wⁱ	0.83 (1)	1.90 (1)	2.734 (1)	175 (2)
O1w—H1w2⋯O2ⁱⁱ	0.84 (1)	1.81 (1)	2.646 (1)	173 (2)
O2w—H2w1⋯O5wⁱ	0.83 (1)	1.93 (1)	2.761 (1)	174 (2)
O2w—H2w2⋯O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.790 (1)	173 (2)
O3w—H3w1⋯O5w^iv	0.84 (1)	2.16 (2)	2.909 (2)	148 (2)
O3w—H3w2⋯O3ⁱⁱ	0.85 (1)	1.86 (1)	2.694 (1)	167 (2)
O4w—H4w1⋯O6w^v	0.85 (1)	1.98 (1)	2.811 (2)	169 (2)
O4w—H4w2⋯O2^iv	0.85 (1)	2.05 (1)	2.864 (2)	161 (3)
O5w—H5w1⋯O1	0.85 (1)	1.89 (1)	2.716 (2)	164 (2)
O5w—H5w2⋯O3^vi	0.85 (1)	1.90 (1)	2.719 (1)	161 (2)
O6w—H6w1⋯O1	0.85 (1)	1.82 (1)	2.665 (1)	174 (2)
O6w—H6w2⋯O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.784 (1)	174 (2)
N1—H1N1⋯O4w	0.85 (1)	2.06 (1)	2.906 (2)	169 (2)
N1—H1N2⋯O4ⁱⁱⁱ	0.84 (1)	2.30 (1)	3.110 (2)	161 (2)
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) $[x-{\script{1\over 2}}, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) x-1, y, z; (v) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (vi) $[-x+{\script{5\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2004 ); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536810040560/si2299sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810040560/si2299Isup2.hkl

checkCIF report

Comment top

The dianion of 5-aminoisophthalic acid binds to cobalt(II) in a bridging µ₄-manner in the monoaqua derivative (Wu et al., 2002a), and the carboxyl oxygen as well as the amino nitrogen atoms are all involved in bonding in the three-dimensional network structure. A diaqua dihydrate has also been reported; the compound has the monoanion in µ₂ bridging that gives rise to a chain motif (Wu et al., 2002b). The 4,4'-bipyridine spacer ligand lowers the dimensionality of cobalt 5-aminoisophthalate, and the diqua adduct, which crystallizes as a DMF solvate, exists as linear chains (He et al., 2006). The present 1,10-phenanthroline adduct is a triaqua trihydrate (Scheme I) in which the 5-aminosophthlate dianion binds only through the neutral amino donor site; the coordinated water molecules comprise the fac points of the octahedron around the metal atom (Fig. 1). The zwitterionic dianion, the coordinated and lattice water molecules interact through hydrogen bonds (Table 2) to furnish a tightly-held, three-dimensional network. Pairs of phenanthroline units show π···π interactions about a center-of-inversion at a distance of ca 3.5 Å (Fig. 2).

Related literature top

For related structures, see: He et al. (2006); Wu et al. (2002a,b).

Experimental top

Cobalt(II) nitrate hexahydrate (0.048 g, 0.165 mmol) dissolved in water (5 ml) was added to a mixture of 5-amino-isophthalic acid (0.030 g, 0.165 mmol) and sodium hydroxidie (0.013 g, 0.330 mmol) dissolved in water (5 ml). To this solution was added 1,10-phenanthroline (0.033 g, 0.165 mmol) dissolved in methanol (10 ml). The mixture was filtered and set aside for the growth of deep red crystals (35% yield based on the acid). CHN elemental analaysis. Calc. for C₂₀H₂₅C_ON₃O₁₀: C 45.63, H 4.79, N 7.98%. Found: C, 45.49; H, 4.89; N,7.91%.

Structure description top

For related structures, see: He et al. (2006); Wu et al. (2002a,b).

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

	Fig. 1. Thermal displacement ellipsoid plot of (I) at the 70% probability level; hydrogen atoms are shown as spheres of arbitrary radii.
	Fig. 2. Two formula units of (I) showing π···π interactions about a center-of-inversion.

(5-Aminoisophthalato-κN)triaqua(1,10-phenanthroline- κ²N,N')cobalt(II) trihydrate top

Crystal data top

[Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O	F(000) = 1092
M_r = 526.36	D_x = 1.527 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9790 reflections
a = 10.1182 (2) Å	θ = 2.5–28.5°
b = 13.9659 (2) Å	µ = 0.81 mm⁻¹
c = 16.2850 (2) Å	T = 293 K
β = 95.827 (1)°	Prism, red
V = 2289.34 (8) Å³	0.24 × 0.22 × 0.18 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	5683 independent reflections
Radiation source: fine-focus sealed tube	5120 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
φ and ω scans	θ_max = 28.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −13→13
T_min = 0.803, T_max = 1.000	k = −18→18
18954 measured reflections	l = −21→21

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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ²(F_o²) + (0.0539P)² + 0.5451P] where P = (F_o² + 2F_c²)/3
5683 reflections	(Δ/σ)_max = 0.001
363 parameters	Δρ_max = 0.47 e Å⁻³
14 restraints	Δρ_min = −0.46 e Å⁻³

Crystal data top

[Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O	V = 2289.34 (8) Å³
M_r = 526.36	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.1182 (2) Å	µ = 0.81 mm⁻¹
b = 13.9659 (2) Å	T = 293 K
c = 16.2850 (2) Å	0.24 × 0.22 × 0.18 mm
β = 95.827 (1)°

Data collection top

Bruker APEXII area-detector diffractometer	5683 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5120 reflections with I > 2σ(I)
T_min = 0.803, T_max = 1.000	R_int = 0.027
18954 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	14 restraints
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.47 e Å⁻³
5683 reflections	Δρ_min = −0.46 e Å⁻³
363 parameters

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

	x	y	z	U_iso*/U_eq
Co1	0.742889 (15)	0.684399 (12)	0.466367 (10)	0.01480 (6)
O1	1.15673 (10)	0.53092 (8)	0.26398 (8)	0.0313 (2)
O2	1.22644 (9)	0.64316 (8)	0.18340 (7)	0.0283 (2)
O3	0.92170 (9)	0.91482 (7)	0.09694 (6)	0.02231 (19)
O4	0.72213 (9)	0.92307 (7)	0.14075 (6)	0.0237 (2)
O1W	0.76586 (10)	0.70374 (8)	0.59335 (6)	0.0228 (2)
H1W1	0.8296 (15)	0.6766 (13)	0.6202 (12)	0.036 (6)*
H1W2	0.749 (2)	0.7538 (11)	0.6187 (13)	0.052 (7)*
O2W	0.79629 (9)	0.54265 (7)	0.49718 (6)	0.01971 (18)
H2W1	0.7468 (16)	0.5247 (15)	0.5321 (10)	0.037 (6)*
H2W2	0.784 (2)	0.5056 (14)	0.4555 (10)	0.049 (6)*
O3W	0.53714 (9)	0.66780 (8)	0.47286 (6)	0.0235 (2)
H3W1	0.486 (2)	0.6450 (17)	0.4334 (11)	0.057 (7)*
H3W2	0.509 (2)	0.6474 (15)	0.5168 (9)	0.042 (6)*
O4W	0.44314 (12)	0.71848 (11)	0.29095 (9)	0.0424 (3)
H4W1	0.451 (2)	0.7710 (11)	0.2661 (14)	0.056 (7)*
H4W2	0.390 (2)	0.6844 (17)	0.2600 (15)	0.067 (9)*
O5W	1.35918 (11)	0.52866 (8)	0.38701 (7)	0.0276 (2)
H5W1	1.3070 (18)	0.5252 (16)	0.3431 (9)	0.041 (6)*
H5W2	1.4231 (15)	0.4911 (13)	0.3801 (13)	0.040 (6)*
O6W	1.02652 (9)	0.37775 (7)	0.31095 (7)	0.0248 (2)
H6W1	1.063 (2)	0.4287 (10)	0.2960 (13)	0.044 (6)*
H6W2	0.9517 (13)	0.3885 (15)	0.3285 (13)	0.045 (6)*
N1	0.70534 (10)	0.63853 (8)	0.33691 (6)	0.0168 (2)
H1N1	0.6259 (11)	0.6547 (13)	0.3202 (11)	0.023 (4)*
H1N2	0.7054 (19)	0.5782 (7)	0.3384 (12)	0.031 (5)*
N2	0.71726 (11)	0.83333 (8)	0.43935 (7)	0.0198 (2)
N3	0.94173 (10)	0.73017 (8)	0.45306 (7)	0.0186 (2)
C1	0.79644 (12)	0.67271 (9)	0.28227 (7)	0.0155 (2)
C2	0.91651 (12)	0.62476 (9)	0.27734 (7)	0.0166 (2)
H2	0.9344	0.5688	0.3074	0.020*
C3	1.00960 (11)	0.66020 (9)	0.22771 (7)	0.0160 (2)
C4	0.98255 (12)	0.74438 (9)	0.18275 (8)	0.0170 (2)
H4	1.0446	0.7686	0.1498	0.020*
C5	0.86219 (11)	0.79214 (9)	0.18732 (7)	0.0158 (2)
C6	0.76966 (12)	0.75642 (9)	0.23778 (7)	0.0168 (2)
H6	0.6902	0.7888	0.2415	0.020*
C7	1.14016 (11)	0.60753 (9)	0.22423 (8)	0.0180 (2)
C8	0.83353 (12)	0.88295 (9)	0.13858 (7)	0.0164 (2)
C9	0.60574 (14)	0.88414 (11)	0.43592 (9)	0.0264 (3)
H9	0.5278	0.8534	0.4466	0.032*
C10	0.60072 (16)	0.98217 (12)	0.41679 (10)	0.0316 (3)
H10	0.5210	1.0156	0.4157	0.038*
C11	0.71446 (17)	1.02817 (11)	0.39974 (9)	0.0307 (3)
H11	0.7127	1.0932	0.3875	0.037*
C12	0.83406 (15)	0.97630 (10)	0.40083 (9)	0.0259 (3)
C13	0.83020 (13)	0.87881 (10)	0.42259 (8)	0.0195 (2)
C14	0.95735 (17)	1.01683 (12)	0.38069 (11)	0.0365 (4)
H14	0.9602	1.0810	0.3657	0.044*
C15	1.06906 (17)	0.96363 (13)	0.38306 (12)	0.0379 (4)
H15	1.1469	0.9912	0.3682	0.045*
C16	1.06940 (14)	0.86486 (12)	0.40818 (10)	0.0280 (3)
C17	0.95058 (13)	0.82265 (10)	0.42820 (8)	0.0198 (2)
C18	1.18338 (15)	0.80580 (13)	0.41512 (11)	0.0353 (4)
H18	1.2640	0.8297	0.4013	0.042*
C19	1.17504 (14)	0.71351 (13)	0.44210 (11)	0.0326 (3)
H19	1.2503	0.6749	0.4482	0.039*
C20	1.05169 (13)	0.67760 (10)	0.46052 (9)	0.0245 (3)
H20	1.0469	0.6147	0.4786	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01501 (9)	0.01376 (10)	0.01610 (10)	0.00058 (5)	0.00396 (6)	0.00020 (6)
O1	0.0198 (4)	0.0260 (5)	0.0490 (7)	0.0059 (4)	0.0081 (4)	0.0196 (5)
O2	0.0216 (4)	0.0249 (5)	0.0407 (6)	0.0061 (4)	0.0137 (4)	0.0139 (5)
O3	0.0215 (4)	0.0204 (5)	0.0265 (5)	0.0018 (4)	0.0095 (3)	0.0082 (4)
O4	0.0216 (4)	0.0192 (5)	0.0320 (5)	0.0066 (4)	0.0109 (4)	0.0087 (4)
O1W	0.0260 (5)	0.0237 (5)	0.0185 (4)	0.0059 (4)	0.0009 (4)	−0.0061 (4)
O2W	0.0266 (4)	0.0146 (4)	0.0182 (4)	−0.0006 (4)	0.0031 (3)	−0.0010 (4)
O3W	0.0170 (4)	0.0344 (5)	0.0198 (5)	−0.0033 (4)	0.0045 (3)	−0.0009 (4)
O4W	0.0265 (5)	0.0461 (8)	0.0526 (8)	−0.0063 (5)	−0.0051 (5)	0.0224 (7)
O5W	0.0306 (5)	0.0256 (5)	0.0269 (5)	0.0060 (4)	0.0045 (4)	0.0030 (4)
O6W	0.0206 (4)	0.0192 (5)	0.0354 (5)	0.0003 (4)	0.0073 (4)	0.0018 (4)
N1	0.0181 (4)	0.0166 (5)	0.0165 (5)	−0.0001 (4)	0.0058 (4)	0.0032 (4)
N2	0.0202 (5)	0.0180 (5)	0.0214 (5)	0.0022 (4)	0.0036 (4)	0.0007 (4)
N3	0.0171 (5)	0.0184 (5)	0.0205 (5)	−0.0001 (4)	0.0025 (4)	−0.0015 (4)
C1	0.0175 (5)	0.0165 (5)	0.0132 (5)	−0.0008 (4)	0.0041 (4)	0.0009 (4)
C2	0.0192 (5)	0.0147 (5)	0.0161 (5)	0.0009 (4)	0.0024 (4)	0.0027 (4)
C3	0.0157 (5)	0.0152 (5)	0.0172 (5)	0.0011 (4)	0.0022 (4)	0.0005 (4)
C4	0.0171 (5)	0.0167 (6)	0.0180 (5)	0.0000 (4)	0.0051 (4)	0.0024 (5)
C5	0.0175 (5)	0.0139 (5)	0.0166 (5)	0.0008 (4)	0.0041 (4)	0.0022 (4)
C6	0.0168 (5)	0.0172 (6)	0.0171 (5)	0.0020 (4)	0.0051 (4)	0.0006 (5)
C7	0.0152 (5)	0.0166 (6)	0.0222 (6)	0.0011 (4)	0.0020 (4)	0.0028 (5)
C8	0.0194 (5)	0.0136 (5)	0.0164 (5)	0.0008 (4)	0.0035 (4)	0.0018 (4)
C9	0.0251 (6)	0.0243 (7)	0.0308 (7)	0.0063 (5)	0.0066 (5)	0.0030 (6)
C10	0.0378 (8)	0.0258 (7)	0.0313 (7)	0.0149 (6)	0.0044 (6)	0.0046 (6)
C11	0.0465 (8)	0.0180 (6)	0.0267 (7)	0.0059 (6)	−0.0005 (6)	0.0034 (6)
C12	0.0349 (7)	0.0185 (6)	0.0236 (6)	−0.0026 (5)	−0.0004 (5)	0.0037 (5)
C13	0.0234 (6)	0.0172 (6)	0.0178 (5)	−0.0011 (5)	0.0019 (4)	0.0006 (5)
C14	0.0441 (9)	0.0232 (7)	0.0416 (9)	−0.0111 (6)	0.0012 (7)	0.0102 (7)
C15	0.0344 (8)	0.0343 (9)	0.0454 (9)	−0.0156 (7)	0.0063 (7)	0.0089 (7)
C16	0.0239 (6)	0.0296 (7)	0.0309 (7)	−0.0085 (6)	0.0050 (5)	0.0024 (6)
C17	0.0196 (6)	0.0199 (6)	0.0201 (6)	−0.0025 (5)	0.0026 (4)	−0.0012 (5)
C18	0.0186 (6)	0.0439 (10)	0.0441 (9)	−0.0075 (6)	0.0068 (6)	−0.0006 (7)
C19	0.0166 (6)	0.0376 (8)	0.0436 (9)	0.0031 (6)	0.0034 (6)	−0.0033 (7)
C20	0.0202 (6)	0.0229 (7)	0.0302 (7)	0.0027 (5)	0.0011 (5)	−0.0025 (5)

Geometric parameters (Å, º) top

Co1—O1W	2.0750 (10)	C1—C2	1.3967 (16)
Co1—O2W	2.0995 (9)	C2—C3	1.3927 (16)
Co1—O3W	2.1080 (9)	C2—H2	0.9300
Co1—N2	2.1364 (12)	C3—C4	1.3974 (17)
Co1—N3	2.1429 (10)	C3—C7	1.5181 (16)
Co1—N1	2.1992 (11)	C4—C5	1.3971 (16)
O1—C7	1.2530 (16)	C4—H4	0.9300
O2—C7	1.2530 (15)	C5—C6	1.3989 (16)
O3—C8	1.2556 (14)	C5—C8	1.5086 (17)
O4—C8	1.2624 (15)	C6—H6	0.9300
O1W—H1W1	0.83 (1)	C9—C10	1.404 (2)
O1W—H1W2	0.84 (1)	C9—H9	0.9300
O2W—H2W1	0.83 (1)	C10—C11	1.371 (2)
O2W—H2W2	0.85 (1)	C10—H10	0.9300
O3W—H3W1	0.84 (1)	C11—C12	1.409 (2)
O3W—H3W2	0.85 (1)	C11—H11	0.9300
O4W—H4W1	0.85 (1)	C12—C13	1.4085 (19)
O4W—H4W2	0.85 (1)	C12—C14	1.438 (2)
O5W—H5W1	0.85 (1)	C13—C17	1.4437 (18)
O5W—H5W2	0.85 (1)	C14—C15	1.350 (3)
O6W—H6W1	0.85 (1)	C14—H14	0.9300
O6W—H6W2	0.85 (1)	C15—C16	1.439 (2)
N1—C1	1.4269 (15)	C15—H15	0.9300
N1—H1N1	0.85 (1)	C16—C17	1.4066 (18)
N1—H1N2	0.84 (1)	C16—C18	1.413 (2)
N2—C9	1.3293 (17)	C18—C19	1.367 (2)
N2—C13	1.3590 (17)	C18—H18	0.9300
N3—C20	1.3282 (17)	C19—C20	1.405 (2)
N3—C17	1.3593 (17)	C19—H19	0.9300
C1—C6	1.3876 (17)	C20—H20	0.9300

O1W—Co1—O2W	83.37 (4)	C3—C4—H4	120.0
O1W—Co1—O3W	88.60 (4)	C4—C5—C6	120.00 (11)
O2W—Co1—O3W	96.65 (4)	C4—C5—C8	119.70 (10)
O1W—Co1—N2	94.45 (4)	C6—C5—C8	120.29 (11)
O2W—Co1—N2	171.97 (4)	C1—C6—C5	120.02 (11)
O3W—Co1—N2	91.01 (4)	C1—C6—H6	120.0
O1W—Co1—N3	92.90 (4)	C5—C6—H6	120.0
O2W—Co1—N3	94.82 (4)	O2—C7—O1	123.33 (11)
O3W—Co1—N3	168.53 (4)	O2—C7—C3	118.90 (11)
N2—Co1—N3	77.54 (4)	O1—C7—C3	117.76 (11)
O1W—Co1—N1	169.81 (4)	O3—C8—O4	122.90 (11)
O2W—Co1—N1	88.26 (4)	O3—C8—C5	118.22 (11)
O3W—Co1—N1	86.60 (4)	O4—C8—C5	118.88 (10)
N2—Co1—N1	94.62 (4)	N2—C9—C10	122.77 (14)
N3—Co1—N1	93.59 (4)	N2—C9—H9	118.6
Co1—O1W—H1W1	117.8 (15)	C10—C9—H9	118.6
Co1—O1W—H1W2	126.2 (16)	C11—C10—C9	119.33 (14)
H1W1—O1W—H1W2	108 (2)	C11—C10—H10	120.3
Co1—O2W—H2W1	106.8 (15)	C9—C10—H10	120.3
Co1—O2W—H2W2	111.5 (16)	C10—C11—C12	119.61 (14)
H2W1—O2W—H2W2	108 (2)	C10—C11—H11	120.2
Co1—O3W—H3W1	122.1 (17)	C12—C11—H11	120.2
Co1—O3W—H3W2	120.1 (15)	C13—C12—C11	117.03 (13)
H3W1—O3W—H3W2	106 (2)	C13—C12—C14	119.00 (14)
H4W1—O4W—H4W2	107 (2)	C11—C12—C14	123.96 (14)
H5W1—O5W—H5W2	106 (2)	N2—C13—C12	123.20 (12)
H6W1—O6W—H6W2	112 (2)	N2—C13—C17	117.04 (12)
C1—N1—Co1	116.15 (8)	C12—C13—C17	119.75 (12)
C1—N1—H1N1	111.1 (12)	C15—C14—C12	121.35 (14)
Co1—N1—H1N1	107.1 (12)	C15—C14—H14	119.3
C1—N1—H1N2	110.7 (13)	C12—C14—H14	119.3
Co1—N1—H1N2	105.3 (13)	C14—C15—C16	120.90 (14)
H1N1—N1—H1N2	105.8 (18)	C14—C15—H15	119.5
C9—N2—C13	118.01 (12)	C16—C15—H15	119.5
C9—N2—Co1	127.81 (10)	C17—C16—C18	116.54 (14)
C13—N2—Co1	114.17 (9)	C17—C16—C15	119.36 (14)
C20—N3—C17	118.20 (11)	C18—C16—C15	124.11 (14)
C20—N3—Co1	127.75 (10)	N3—C17—C16	123.43 (13)
C17—N3—Co1	113.86 (8)	N3—C17—C13	117.02 (11)
C6—C1—C2	119.92 (11)	C16—C17—C13	119.55 (13)
C6—C1—N1	120.22 (11)	C19—C18—C16	119.97 (14)
C2—C1—N1	119.75 (11)	C19—C18—H18	120.0
C3—C2—C1	120.43 (11)	C16—C18—H18	120.0
C3—C2—H2	119.8	C18—C19—C20	119.35 (14)
C1—C2—H2	119.8	C18—C19—H19	120.3
C2—C3—C4	119.67 (11)	C20—C19—H19	120.3
C2—C3—C7	119.46 (11)	N3—C20—C19	122.48 (14)
C4—C3—C7	120.86 (11)	N3—C20—H20	118.8
C5—C4—C3	119.95 (11)	C19—C20—H20	118.8
C5—C4—H4	120.0

O1W—Co1—N1—C1	−145.0 (2)	C4—C5—C8—O3	−2.25 (18)
O2W—Co1—N1—C1	−110.28 (9)	C6—C5—C8—O3	176.88 (12)
O3W—Co1—N1—C1	152.95 (9)	C4—C5—C8—O4	177.14 (12)
N2—Co1—N1—C1	62.21 (9)	C6—C5—C8—O4	−3.73 (18)
N3—Co1—N1—C1	−15.56 (9)	C13—N2—C9—C10	−0.8 (2)
O1W—Co1—N2—C9	−85.16 (12)	Co1—N2—C9—C10	−179.49 (11)
O3W—Co1—N2—C9	3.51 (12)	N2—C9—C10—C11	0.9 (2)
N3—Co1—N2—C9	−177.16 (13)	C9—C10—C11—C12	0.7 (2)
N1—Co1—N2—C9	90.18 (12)	C10—C11—C12—C13	−2.1 (2)
O1W—Co1—N2—C13	96.06 (9)	C10—C11—C12—C14	177.43 (16)
O3W—Co1—N2—C13	−175.26 (9)	C9—N2—C13—C12	−0.9 (2)
N3—Co1—N2—C13	4.07 (9)	Co1—N2—C13—C12	178.02 (10)
N1—Co1—N2—C13	−88.59 (9)	C9—N2—C13—C17	178.87 (12)
O1W—Co1—N3—C20	85.77 (12)	Co1—N2—C13—C17	−2.23 (15)
O2W—Co1—N3—C20	2.19 (12)	C11—C12—C13—N2	2.3 (2)
O3W—Co1—N3—C20	−176.94 (17)	C14—C12—C13—N2	−177.27 (14)
N2—Co1—N3—C20	179.69 (12)	C11—C12—C13—C17	−177.44 (13)
N1—Co1—N3—C20	−86.36 (12)	C14—C12—C13—C17	3.0 (2)
O1W—Co1—N3—C17	−99.37 (9)	C13—C12—C14—C15	−0.7 (2)
O2W—Co1—N3—C17	177.06 (9)	C11—C12—C14—C15	179.79 (16)
O3W—Co1—N3—C17	−2.1 (3)	C12—C14—C15—C16	−1.8 (3)
N2—Co1—N3—C17	−5.45 (9)	C14—C15—C16—C17	1.9 (3)
N1—Co1—N3—C17	88.50 (9)	C14—C15—C16—C18	−177.55 (17)
Co1—N1—C1—C6	−92.87 (12)	C20—N3—C17—C16	1.5 (2)
Co1—N1—C1—C2	83.33 (13)	Co1—N3—C17—C16	−173.89 (11)
C6—C1—C2—C3	−0.27 (19)	C20—N3—C17—C13	−178.51 (12)
N1—C1—C2—C3	−176.48 (11)	Co1—N3—C17—C13	6.10 (15)
C1—C2—C3—C4	0.13 (19)	C18—C16—C17—N3	−0.1 (2)
C1—C2—C3—C7	179.20 (11)	C15—C16—C17—N3	−179.52 (14)
C2—C3—C4—C5	−0.45 (19)	C18—C16—C17—C13	179.94 (14)
C7—C3—C4—C5	−179.51 (11)	C15—C16—C17—C13	0.5 (2)
C3—C4—C5—C6	0.91 (19)	N2—C13—C17—N3	−2.64 (18)
C3—C4—C5—C8	−179.95 (11)	C12—C13—C17—N3	177.12 (12)
C2—C1—C6—C5	0.73 (19)	N2—C13—C17—C16	177.35 (12)
N1—C1—C6—C5	176.92 (11)	C12—C13—C17—C16	−2.9 (2)
C4—C5—C6—C1	−1.06 (19)	C17—C16—C18—C19	−1.6 (2)
C8—C5—C6—C1	179.81 (11)	C15—C16—C18—C19	177.86 (17)
C2—C3—C7—O2	−175.69 (12)	C16—C18—C19—C20	1.7 (3)
C4—C3—C7—O2	3.38 (19)	C17—N3—C20—C19	−1.3 (2)
C2—C3—C7—O1	3.05 (18)	Co1—N3—C20—C19	173.33 (11)
C4—C3—C7—O1	−177.88 (13)	C18—C19—C20—N3	−0.3 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O6wⁱ	0.83 (1)	1.90 (1)	2.734 (1)	175 (2)
O1w—H1w2···O2ⁱⁱ	0.84 (1)	1.81 (1)	2.646 (1)	173 (2)
O2w—H2w1···O5wⁱ	0.83 (1)	1.93 (1)	2.761 (1)	174 (2)
O2w—H2w2···O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.790 (1)	173 (2)
O3w—H3w1···O5w^iv	0.84 (1)	2.16 (2)	2.909 (2)	148 (2)
O3w—H3w2···O3ⁱⁱ	0.85 (1)	1.86 (1)	2.694 (1)	167 (2)
O4w—H4w1···O6w^v	0.85 (1)	1.98 (1)	2.811 (2)	169 (2)
O4w—H4w2···O2^iv	0.85 (1)	2.05 (1)	2.864 (2)	161 (3)
O5w—H5w1···O1	0.85 (1)	1.89 (1)	2.716 (2)	164 (2)
O5w—H5w2···O3^vi	0.85 (1)	1.90 (1)	2.719 (1)	161 (2)
O6w—H6w1···O1	0.85 (1)	1.82 (1)	2.665 (1)	174 (2)
O6w—H6w2···O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.784 (1)	174 (2)
N1—H1N1···O4w	0.85 (1)	2.06 (1)	2.906 (2)	169 (2)
N1—H1N2···O4ⁱⁱⁱ	0.84 (1)	2.30 (1)	3.110 (2)	161 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	[Co(C₈H₅NO₄)(C₁₂H₈N₂)(H₂O)₃]·3H₂O
M_r	526.36
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.1182 (2), 13.9659 (2), 16.2850 (2)
β (°)	95.827 (1)
V (Å³)	2289.34 (8)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.24 × 0.22 × 0.18

Data collection
Diffractometer	Bruker APEXII area-detector
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.803, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	18954, 5683, 5120
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.672

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.086, 1.04
No. of reflections	5683
No. of parameters	363
No. of restraints	14
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.46

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1w—H1w1···O6wⁱ	0.83 (1)	1.90 (1)	2.734 (1)	175 (2)
O1w—H1w2···O2ⁱⁱ	0.84 (1)	1.81 (1)	2.646 (1)	173 (2)
O2w—H2w1···O5wⁱ	0.83 (1)	1.93 (1)	2.761 (1)	174 (2)
O2w—H2w2···O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.790 (1)	173 (2)
O3w—H3w1···O5w^iv	0.84 (1)	2.16 (2)	2.909 (2)	148 (2)
O3w—H3w2···O3ⁱⁱ	0.85 (1)	1.86 (1)	2.694 (1)	167 (2)
O4w—H4w1···O6w^v	0.85 (1)	1.98 (1)	2.811 (2)	169 (2)
O4w—H4w2···O2^iv	0.85 (1)	2.05 (1)	2.864 (2)	161 (3)
O5w—H5w1···O1	0.85 (1)	1.89 (1)	2.716 (2)	164 (2)
O5w—H5w2···O3^vi	0.85 (1)	1.90 (1)	2.719 (1)	161 (2)
O6w—H6w1···O1	0.85 (1)	1.82 (1)	2.665 (1)	174 (2)
O6w—H6w2···O4ⁱⁱⁱ	0.85 (1)	1.94 (1)	2.784 (1)	174 (2)
N1—H1N1···O4w	0.85 (1)	2.06 (1)	2.906 (2)	169 (2)
N1—H1N2···O4ⁱⁱⁱ	0.84 (1)	2.30 (1)	3.110 (2)	161 (2)

Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) x−1/2, −y+3/2, z+1/2; (iii) −x+3/2, y−1/2, −z+1/2; (iv) x−1, y, z; (v) −x+3/2, y+1/2, −z+1/2; (vi) −x+5/2, y−1/2, −z+1/2.

Acknowledgements

We thank the Key Laboratory of Environmental Material and Environmental Engineering of Jiangsu Province, the National Natural Science Foundation of China (grant No. 20773107), Yangzhou University and the University of Malaya for supporting this study.

References

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