Poly[aqua­{μ3-5-[(pyridin-2-ylmeth­yl)amino]­isophthalato-κ5N,N′:O1,O1′:O3}cobalt(II)]

Zhu, X.-H.; Cheng, X.-C.

doi:10.1107/S1600536811050318

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 12| December 2011| Page m1862

https://doi.org/10.1107/S1600536811050318

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Poly[aqua{μ₃-5-[(pyridin-2-ylmethyl)amino]isophthalato-κ⁵N,N′:O¹,O^1′:O³}cobalt(II)]

Xiao-Hong Zhu ^a ^* and Xiao-Chun Cheng ^a

^aFaculty of Life Science and Chemical Engineering, Huaiyin Institute of Technology, Huaian 223003, People's Republic of China
^*Correspondence e-mail: hgzhuxh@yeah.net

(Received 29 October 2011; accepted 23 November 2011; online 30 November 2011)

In the title polymer, {[Co(C₁₄H₁₀N₂O₄)(H₂O)]·3.5H₂O}_n, the Co²⁺ ion is coordinated by three carboxylate O atoms from two 5-[(pyridin-2-ylmethyl)amino]isophthalate anions, two N atoms from a (pyridin-2-ylmethyl)amino group and an O atom from a water molecule, furnishing a distorted CoO₄N₂ octahedral geometry. Each anion acts as a μ₃-bridge, linking cobalt ions into a two-dimensional layer parallel to (100). The asymmetric unit also contains three and a half solvent water molecules, which could not be modeled. Therefore, the diffraction contribution of the solvent water molecules was removed by the subroutine SQUEEZE in PLATON [Spek (2009). Acta Cryst. D65, 148–155]. The crystal structure is stabilized by O—H⋯O hydrogen bonds in which the coordinated water molecule acts as donor and the carboxylate O atoms as acceptors.

Related literature

For related structures, see: Kuai et al. (2011 ).

Experimental

Crystal data

[Co(C₁₄H₁₀N₂O₄)(H₂O)]·3.5H₂O
M_r = 410.24
Monoclinic, P 2₁ /c
a = 11.0926 (11) Å
b = 9.8735 (10) Å
c = 17.4317 (15) Å
β = 116.533 (5)°
V = 1708.1 (3) Å³
Z = 4
Mo Kα radiation
μ = 1.05 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.20 mm

Data collection

Bruker SMART APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.821, T_max = 0.821
11993 measured reflections
4259 independent reflections
3809 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.124
S = 1.11
4259 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.81 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O3ⁱ	1.9999 (19)
Co1—N2ⁱⁱ	2.090 (2)
Co1—O5	2.110 (2)
Co1—O1	2.132 (2)
Co1—O2	2.195 (2)
Co1—N1ⁱⁱ	2.275 (2)
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (ii) -x+2, -y+1, -z+1.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O5—H5WA⋯O4ⁱ	0.87	2.25	2.946 (3)	137
O5—H5WA⋯O1ⁱⁱⁱ	0.87	2.42	3.047 (3)	130
O5—H5W⋯O4^iv	0.93	1.90	2.819 (3)	168
Symmetry codes: (i) $[x, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ ; (iii) -x+2, -y, -z+1; (iv) $[-x+2, y-{\script{1\over 2}}, -z+{\script{3\over 2}}]$ .

Data collection: APEX2 (Bruker, 2008 ); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536811050318/pv2477sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811050318/pv2477Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536811050318/pv2477Isup3.cdx

checkCIF report

Comment top

5-(Pyridin-2-ylmethyl)aminoisophthalic acid possesses some peculiar features in the assembly of coordination compounds due to its unique molecular structure. Herein, we report the crystal structure of the title complex. The asymmetric unit consists of one cobalt ion, one 5-(pyridin-2-ylmethyl)aminoisophthalate anion, one coordinated water molecule, and 3.5 lattice water molecules. However, the solvent water molecules could not be modeled as discrete atomic sites. We employed SQUEEZE subroutine in PLATON (Spek, 2009) to exclude the diffraction contribution of the solvent water molecules.

In the title polymer, each Co ion is coordinated by three carboxylate O atoms from two different 5-(pyridin-2-ylmethyl)aminoisophthalate anions, two N atoms from (pyridin-2-ylmethyl)amino group and one O atom from a coordinated water molecule, to furnish a distorted CoO₄N₂ octahedral geometry (Fig. 1). Each anion acts as a µ₃-bridge, linking cobalt ions to form a two-dimensional layer. In the crystal structure, there exist O—H···O hydrogen bonds (Table 1). Coordinated water molecule and carboxylate oxygen atoms act as donors or acceptors in the formation of these hydrogen bonding interactions.

Related literature top

For related structures, see: Kuai et al. (2011).

Experimental top

A mixture of cobalt nitrate hexahydrate (58.2 mg, 0.2 mmol), 5-(pyridin-2-ylmethyl)aminoisophthalic acid (54.4 mg, 0.2 mmol), and 3 ml N,N-dimethylformamide in H₂O (12 ml) was sealed in a 16 ml Teflon-lined stainless steel container and heated to 373 K for 3 days. After cooling the container to the room temperature, red block crystals of the title complex were obtained.

Structure description top

For related structures, see: Kuai et al. (2011).

Computing details top

Data collection: APEX2 (Bruker, 2008); cell refinement: SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg, 2000); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. : The coordination environment of Co ion in the title complex with the ellipsoids drawn at the 30% probability level. The hydrogen atoms have been omitted for clarity. Symmetry codes: A = -x + 2, -y + 1, -z + 1; B = x, -y + 1/2, z - 1/2; C = x, -y + 1/2, z + 1/2.

Poly[aqua{µ₃-5-[(pyridin-2-ylmethyl)amino]isophthalato- κ⁵N,N':O¹,O^1':O³}cobalt(II)] top

Crystal data top

[Co(C₁₄H₁₀N₂O₄)(H₂O)]·3.5H₂O	F(000) = 846
M_r = 410.24	D_x = 1.593 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 6314 reflections
a = 11.0926 (11) Å	θ = 2.4–28.4°
b = 9.8735 (10) Å	µ = 1.05 mm⁻¹
c = 17.4317 (15) Å	T = 293 K
β = 116.533 (5)°	Block, red
V = 1708.1 (3) Å³	0.20 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker SMART APEXII CCD diffractometer	4259 independent reflections
Radiation source: fine-focus sealed tube	3809 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
φ and ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −14→12
T_min = 0.821, T_max = 0.821	k = −13→10
11993 measured reflections	l = −22→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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.124	H-atom parameters constrained
S = 1.11	w = 1/[σ²(F_o²) + (0.0407P)² + 3.8921P] where P = (F_o² + 2F_c²)/3
4259 reflections	(Δ/σ)_max = 0.001
199 parameters	Δρ_max = 0.81 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

[Co(C₁₄H₁₀N₂O₄)(H₂O)]·3.5H₂O	V = 1708.1 (3) Å³
M_r = 410.24	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 11.0926 (11) Å	µ = 1.05 mm⁻¹
b = 9.8735 (10) Å	T = 293 K
c = 17.4317 (15) Å	0.20 × 0.20 × 0.20 mm
β = 116.533 (5)°

Data collection top

Bruker SMART APEXII CCD diffractometer	4259 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3809 reflections with I > 2σ(I)
T_min = 0.821, T_max = 0.821	R_int = 0.021
11993 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.124	H-atom parameters constrained
S = 1.11	Δρ_max = 0.81 e Å⁻³
4259 reflections	Δρ_min = −0.43 e Å⁻³
199 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
C1	0.8386 (3)	0.5358 (3)	0.59337 (16)	0.0210 (5)
C2	0.8790 (3)	0.5330 (3)	0.68135 (17)	0.0225 (5)
H2	0.8344	0.5858	0.7048	0.027*
C3	0.9868 (3)	0.4503 (3)	0.73445 (16)	0.0217 (5)
C4	1.0543 (3)	0.3722 (3)	0.70059 (16)	0.0214 (5)
H4	1.1273	0.3195	0.7364	0.026*
C5	1.0122 (3)	0.3726 (3)	0.61166 (16)	0.0216 (5)
C6	0.9043 (3)	0.4529 (3)	0.55925 (17)	0.0231 (5)
H6	0.8752	0.4514	0.5003	0.028*
C7	1.0840 (3)	0.2913 (3)	0.57301 (17)	0.0232 (5)
C8	1.0286 (3)	0.4465 (3)	0.82983 (17)	0.0242 (5)
C9	0.6291 (3)	0.6616 (3)	0.55952 (19)	0.0291 (6)
H9A	0.6685	0.7056	0.6151	0.035*
H9B	0.5806	0.5819	0.5630	0.035*
C10	0.5346 (3)	0.7568 (3)	0.49261 (18)	0.0261 (5)
C11	0.3962 (3)	0.7546 (3)	0.4660 (2)	0.0375 (7)
H11	0.3587	0.6926	0.4894	0.045*
C12	0.3154 (3)	0.8459 (4)	0.4045 (3)	0.0453 (9)
H12	0.2226	0.8456	0.3856	0.054*
C13	0.3740 (3)	0.9382 (4)	0.3709 (2)	0.0419 (8)
H13	0.3216	1.0010	0.3297	0.050*
C14	0.5124 (3)	0.9341 (3)	0.4002 (2)	0.0333 (6)
H14	0.5523	0.9954	0.3781	0.040*
Co1	1.20146 (4)	0.17514 (4)	0.49770 (2)	0.02074 (11)
N1	0.7352 (2)	0.6226 (2)	0.53540 (15)	0.0239 (5)
H1N	0.6876	0.5862	0.4822	0.029*
N2	0.5908 (2)	0.8448 (2)	0.45967 (15)	0.0243 (5)
O1	1.0210 (2)	0.2537 (2)	0.49556 (13)	0.0298 (4)
O2	1.2068 (2)	0.2644 (2)	0.61450 (14)	0.0318 (5)
O3	1.1274 (2)	0.3701 (2)	0.87308 (12)	0.0270 (4)
O4	0.9694 (3)	0.5200 (3)	0.86000 (15)	0.0454 (6)
O5	1.1716 (2)	−0.0155 (2)	0.54116 (15)	0.0337 (5)
H5WA	1.1069	−0.0587	0.4995	0.040*
H5W	1.1367	−0.0012	0.5799	0.040*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0250 (12)	0.0200 (12)	0.0202 (12)	0.0001 (10)	0.0119 (10)	0.0011 (9)
C2	0.0271 (13)	0.0227 (12)	0.0222 (12)	0.0027 (10)	0.0151 (10)	0.0014 (10)
C3	0.0277 (13)	0.0225 (12)	0.0175 (11)	−0.0013 (10)	0.0123 (10)	−0.0010 (9)
C4	0.0258 (12)	0.0208 (12)	0.0190 (11)	0.0020 (10)	0.0113 (10)	0.0015 (9)
C5	0.0289 (13)	0.0210 (12)	0.0196 (12)	−0.0015 (10)	0.0150 (10)	−0.0012 (9)
C6	0.0297 (13)	0.0236 (12)	0.0182 (11)	−0.0003 (10)	0.0127 (10)	−0.0004 (10)
C7	0.0330 (14)	0.0202 (12)	0.0232 (12)	0.0004 (10)	0.0187 (11)	0.0002 (10)
C8	0.0338 (14)	0.0241 (13)	0.0202 (12)	−0.0003 (11)	0.0170 (11)	0.0002 (10)
C9	0.0282 (14)	0.0330 (15)	0.0322 (15)	0.0032 (12)	0.0188 (12)	0.0063 (12)
C10	0.0263 (13)	0.0258 (13)	0.0275 (13)	0.0020 (11)	0.0133 (11)	−0.0011 (11)
C11	0.0260 (14)	0.0339 (16)	0.051 (2)	−0.0013 (12)	0.0157 (14)	0.0028 (14)
C12	0.0244 (15)	0.0425 (19)	0.064 (2)	0.0062 (14)	0.0155 (15)	0.0073 (17)
C13	0.0323 (16)	0.0419 (18)	0.0445 (19)	0.0135 (14)	0.0110 (14)	0.0100 (15)
C14	0.0347 (15)	0.0333 (15)	0.0318 (15)	0.0097 (13)	0.0149 (13)	0.0072 (12)
Co1	0.02195 (19)	0.0267 (2)	0.01563 (17)	0.00285 (14)	0.01024 (13)	0.00087 (13)
N1	0.0257 (11)	0.0274 (11)	0.0203 (10)	0.0046 (9)	0.0117 (9)	0.0020 (9)
N2	0.0241 (11)	0.0259 (11)	0.0234 (11)	0.0032 (9)	0.0110 (9)	0.0016 (9)
O1	0.0366 (11)	0.0365 (11)	0.0191 (9)	0.0087 (9)	0.0150 (8)	−0.0012 (8)
O2	0.0298 (10)	0.0399 (12)	0.0307 (11)	−0.0009 (9)	0.0179 (9)	−0.0085 (9)
O3	0.0306 (10)	0.0348 (11)	0.0181 (9)	0.0023 (9)	0.0131 (8)	0.0022 (8)
O4	0.0668 (16)	0.0505 (15)	0.0279 (11)	0.0300 (13)	0.0293 (12)	0.0095 (10)
O5	0.0338 (11)	0.0296 (11)	0.0398 (12)	−0.0010 (9)	0.0183 (10)	0.0026 (9)

Geometric parameters (Å, º) top

C1—C2	1.393 (4)	C10—C11	1.391 (4)
C1—C6	1.394 (4)	C11—C12	1.381 (5)
C1—N1	1.427 (3)	C11—H11	0.9300
C2—C3	1.402 (4)	C12—C13	1.392 (5)
C2—H2	0.9300	C12—H12	0.9300
C3—C4	1.377 (4)	C13—C14	1.384 (5)
C3—C8	1.514 (3)	C13—H13	0.9300
C4—C5	1.405 (3)	C14—N2	1.343 (4)
C4—H4	0.9300	C14—H14	0.9300
C5—C6	1.385 (4)	Co1—O3ⁱ	1.9999 (19)
C5—C7	1.488 (3)	Co1—N2ⁱⁱ	2.090 (2)
C6—H6	0.9300	Co1—O5	2.110 (2)
C7—O2	1.252 (4)	Co1—O1	2.132 (2)
C7—O1	1.267 (3)	Co1—O2	2.195 (2)
C8—O4	1.242 (3)	Co1—N1ⁱⁱ	2.275 (2)
C8—O3	1.265 (3)	N1—Co1ⁱⁱ	2.275 (2)
C9—N1	1.468 (3)	N1—H1N	0.9118
C9—C10	1.500 (4)	N2—Co1ⁱⁱ	2.090 (2)
C9—H9A	0.9700	O3—Co1ⁱⁱⁱ	1.9999 (19)
C9—H9B	0.9700	O5—H5WA	0.8710
C10—N2	1.339 (4)	O5—H5W	0.9279

C2—C1—C6	119.1 (2)	C13—C12—H12	120.3
C2—C1—N1	123.6 (2)	C14—C13—C12	118.3 (3)
C6—C1—N1	117.3 (2)	C14—C13—H13	120.8
C1—C2—C3	119.9 (2)	C12—C13—H13	120.8
C1—C2—H2	120.1	N2—C14—C13	122.3 (3)
C3—C2—H2	120.1	N2—C14—H14	118.9
C4—C3—C2	120.7 (2)	C13—C14—H14	118.9
C4—C3—C8	119.9 (2)	O3ⁱ—Co1—N2ⁱⁱ	102.58 (9)
C2—C3—C8	119.4 (2)	O3ⁱ—Co1—O5	97.84 (9)
C3—C4—C5	119.6 (2)	N2ⁱⁱ—Co1—O5	96.50 (9)
C3—C4—H4	120.2	O3ⁱ—Co1—O1	97.79 (8)
C5—C4—H4	120.2	N2ⁱⁱ—Co1—O1	156.61 (9)
C6—C5—C4	119.5 (2)	O5—Co1—O1	91.96 (8)
C6—C5—C7	119.3 (2)	O3ⁱ—Co1—O2	157.69 (8)
C4—C5—C7	121.1 (2)	N2ⁱⁱ—Co1—O2	98.01 (9)
C5—C6—C1	121.1 (2)	O5—Co1—O2	88.21 (9)
C5—C6—H6	119.4	O1—Co1—O2	60.40 (8)
C1—C6—H6	119.4	O3ⁱ—Co1—N1ⁱⁱ	86.81 (8)
O2—C7—O1	119.6 (2)	N2ⁱⁱ—Co1—N1ⁱⁱ	75.91 (9)
O2—C7—C5	121.1 (2)	O5—Co1—N1ⁱⁱ	171.88 (9)
O1—C7—C5	119.2 (2)	O1—Co1—N1ⁱⁱ	94.02 (8)
O4—C8—O3	125.3 (3)	O2—Co1—N1ⁱⁱ	89.96 (8)
O4—C8—C3	119.4 (3)	C1—N1—C9	116.7 (2)
O3—C8—C3	115.3 (2)	C1—N1—Co1ⁱⁱ	117.72 (17)
N1—C9—C10	108.2 (2)	C9—N1—Co1ⁱⁱ	102.74 (17)
N1—C9—H9A	110.1	C1—N1—H1N	113.6
C10—C9—H9A	110.1	C9—N1—H1N	102.8
N1—C9—H9B	110.1	Co1ⁱⁱ—N1—H1N	101.1
C10—C9—H9B	110.1	C10—N2—C14	119.4 (3)
H9A—C9—H9B	108.4	C10—N2—Co1ⁱⁱ	115.93 (18)
N2—C10—C11	121.6 (3)	C14—N2—Co1ⁱⁱ	124.6 (2)
N2—C10—C9	116.2 (2)	C7—O1—Co1	91.19 (17)
C11—C10—C9	122.2 (3)	C7—O2—Co1	88.71 (16)
C12—C11—C10	119.0 (3)	C8—O3—Co1ⁱⁱⁱ	127.34 (17)
C12—C11—H11	120.5	Co1—O5—H5WA	110.0
C10—C11—H11	120.5	Co1—O5—H5W	108.0
C11—C12—C13	119.4 (3)	H5WA—O5—H5W	103.0
C11—C12—H12	120.3

C6—C1—C2—C3	1.8 (4)	C6—C1—N1—C9	153.4 (3)
N1—C1—C2—C3	−176.3 (2)	C2—C1—N1—Co1ⁱⁱ	94.4 (3)
C1—C2—C3—C4	0.4 (4)	C6—C1—N1—Co1ⁱⁱ	−83.8 (3)
C1—C2—C3—C8	−179.2 (2)	C10—C9—N1—C1	177.6 (2)
C2—C3—C4—C5	−1.7 (4)	C10—C9—N1—Co1ⁱⁱ	47.3 (3)
C8—C3—C4—C5	177.9 (2)	C11—C10—N2—C14	0.7 (4)
C3—C4—C5—C6	0.7 (4)	C9—C10—N2—C14	−179.2 (3)
C3—C4—C5—C7	179.0 (2)	C11—C10—N2—Co1ⁱⁱ	−176.5 (2)
C4—C5—C6—C1	1.6 (4)	C9—C10—N2—Co1ⁱⁱ	3.6 (3)
C7—C5—C6—C1	−176.7 (2)	C13—C14—N2—C10	−0.5 (5)
C2—C1—C6—C5	−2.8 (4)	C13—C14—N2—Co1ⁱⁱ	176.4 (3)
N1—C1—C6—C5	175.4 (2)	O2—C7—O1—Co1	−3.4 (3)
C6—C5—C7—O2	149.9 (3)	C5—C7—O1—Co1	173.6 (2)
C4—C5—C7—O2	−28.4 (4)	O3ⁱ—Co1—O1—C7	−173.06 (16)
C6—C5—C7—O1	−27.1 (4)	N2ⁱⁱ—Co1—O1—C7	−22.6 (3)
C4—C5—C7—O1	154.7 (3)	O5—Co1—O1—C7	88.75 (17)
C4—C3—C8—O4	178.1 (3)	O2—Co1—O1—C7	1.93 (15)
C2—C3—C8—O4	−2.3 (4)	N1ⁱⁱ—Co1—O1—C7	−85.74 (17)
C4—C3—C8—O3	0.9 (4)	O1—C7—O2—Co1	3.3 (3)
C2—C3—C8—O3	−179.5 (2)	C5—C7—O2—Co1	−173.6 (2)
N1—C9—C10—N2	−37.2 (4)	O3ⁱ—Co1—O2—C7	11.2 (3)
N1—C9—C10—C11	142.9 (3)	N2ⁱⁱ—Co1—O2—C7	168.46 (17)
N2—C10—C11—C12	−0.3 (5)	O5—Co1—O2—C7	−95.23 (17)
C9—C10—C11—C12	179.6 (3)	O1—Co1—O2—C7	−1.95 (16)
C10—C11—C12—C13	−0.4 (6)	N1ⁱⁱ—Co1—O2—C7	92.69 (17)
C11—C12—C13—C14	0.5 (6)	O4—C8—O3—Co1ⁱⁱⁱ	9.0 (4)
C12—C13—C14—N2	−0.1 (5)	C3—C8—O3—Co1ⁱⁱⁱ	−174.00 (17)
C2—C1—N1—C9	−28.5 (4)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5WA···O4ⁱ	0.87	2.25	2.946 (3)	137
O5—H5WA···O1^iv	0.87	2.42	3.047 (3)	130
O5—H5W···O4^v	0.93	1.90	2.819 (3)	168

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₄H₁₀N₂O₄)(H₂O)]·3.5H₂O
M_r	410.24
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	11.0926 (11), 9.8735 (10), 17.4317 (15)
β (°)	116.533 (5)
V (Å³)	1708.1 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.05
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.821, 0.821
No. of measured, independent and observed [I > 2σ(I)] reflections	11993, 4259, 3809
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.669

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.124, 1.11
No. of reflections	4259
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.81, −0.43

Computer programs: APEX2 (Bruker, 2008), SAINT (Bruker, 2008), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg, 2000), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—O3ⁱ	1.9999 (19)	Co1—O1	2.132 (2)
Co1—N2ⁱⁱ	2.090 (2)	Co1—O2	2.195 (2)
Co1—O5	2.110 (2)	Co1—N1ⁱⁱ	2.275 (2)

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

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O5—H5WA···O4ⁱ	0.87	2.25	2.946 (3)	136.5
O5—H5WA···O1ⁱⁱⁱ	0.87	2.42	3.047 (3)	129.8
O5—H5W···O4^iv	0.93	1.90	2.819 (3)	168.3

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

References

Brandenburg, K. (2000). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2008). APEX2 and SAINT. Bruker AXS Inc., Madison, wisconsin, USA. Google Scholar
Kuai, H.-W., Cheng, X.-C., Feng, L.-D. & Zhu, X.-H. (2011). Z. Anorg. Allg. Chem. 637, 1560–1565. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (1996). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar

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