Bis(1,10-phenanthroline-κ2N,N′)(sulfato-κ2O,O′)cobalt(II) propane-1,3-diol solvate

Zhong, K.-L.

doi:10.1107/S1600536810003478

metal-organic compounds

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Volume 66| Part 3| March 2010| Page m247

doi:10.1107/S1600536810003478

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Bis(1,10-phenanthroline-κ²N,N′)(sulfato-κ²O,O′)cobalt(II) propane-1,3-diol solvate

Kai-Long Zhong ^a ^*

^aDepartment of Applied Chemistry, Nanjing College of Chemical Technology, Nanjing 210048, People's Republic of China
^*Correspondence e-mail: zklong@tom.com

(Received 16 December 2009; accepted 28 January 2010; online 3 February 2010)

The title compound, [Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂, was obtained unexpectedly as a by-product during an attempt to synthesize a mixed-ligand complex of Co^II with 1,10-phenanthroline (phen) and melamine via a solvothermal reaction. The Co^II metal ions are in a distorted octahedral coordination environment formed by four N atoms from two chelating phen ligands and two O atoms from a bidentate sulfate ligand. The two chelating N₂C₂ groups are almost perpendicular to each other [dihedral angle = 80.06 (8)°]. A twofold rotation axis passes through the Co and S atoms, and also through the central C atom of the propane-1,3-diol solvent molecule. Intermolecular O—H⋯O hydrogen bonds help to stabilize the structure.

Related literature

For related cobalt compounds with monodentate, bidentate-bridging sulfate ligands, see: Hennig et al. (1975 ); Li & Zhou (1987 ); Song et al. (2008 ); Zheng & Lin (2003 ). For related complexes with bidentate-chelating ligands, see: Lu et al. (2006 ); Paul et al. (2002 ); Wang et al. (2009 ). For an isostructural structure, see: Zhong et al. (2006 ). For a related structure, see: Chen et al. (2005 ). For applications of transition metal complexes of phen, see: Li et al. (2004 ); Wang et al. (2000 ).

Experimental

Crystal data

[Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂
M_r = 591.49
Monoclinic, C 2/c
a = 18.285 (4) Å
b = 12.422 (3) Å
c = 13.211 (3) Å
β = 121.82 (3)°
V = 2549.7 (13) Å³
Z = 4
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 223 K
0.60 × 0.40 × 0.34 mm

Data collection

Rigaku Mercury CCD diffractometer
Absorption correction: multi-scan (REQAB: Jacobson, 1998 ) T_min = 0.823, T_max = 1.000
7099 measured reflections
2898 independent reflections
2540 reflections with I > 2σ(I)
R_int = 0.021

Refinement

R[F² > 2σ(F²)] = 0.038
wR(F²) = 0.101
S = 1.06
2898 reflections
183 parameters
21 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.72 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3B⋯O2	0.82	1.92	2.737 (3)	179

Data collection: CrystalClear (Rigaku, 2007 ); 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: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810003478/zq2024sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810003478/zq2024Isup2.hkl

checkCIF report

Comment top

Metal-organic complexes have been widely applied in fields of research and production because of their capability of showing novel optical, electronical, magnetical properties. M-phen transition metal complexes (phen = phenantroline) possess important actions in the areas of extraction, plating, bio-inorganic chemistry, analytical chemistry and functional materials (Wang et al., 2000; Li et al., 2004).

Although many transtion metal complexes with sulfate ions as monodentate, bidentate and bidentate-bridging ligands have been structurally characterized (Hennig et al., 1975; Zheng & Lin, 2003; Song et al., 2008), as far as we know, the reports on complexes with bidentate-chelating sulfate ligands are few (Paul et al., 2002; Lu et al., 2006; Wang et al., 2009). Here, we report the crystal structure of the new complex [CoSO₄(C₁₂H₈N₂)₂].C₃H₈O₂unexpectedly obtained during an attempt to synthesize a mixed-ligand complex of cobalt with phen and melamine via a solvothermal reaction, which is analogue with a previously reported Co^II complex (Zhong et al., 2006).

In the crystal structure of the title complex, the Co^II metal ion is six-coordinated in a distorted octahedral environement by four N atoms from two chelating phen ligands and two O atoms from a bidentate-chelating sulfate ligand (Fig. 1). The Co—O bond distance [2.1323 (15) Å], the O—Co—O bite angle [66.54 (8)°], the Co—N bond distances [2.1295 (16)–2.1341 (17) Å] and the N—Co—N bite angle [77.99 (6)°] are very similar to those seen in the previously reported cobalt complex [CoSO₄(C₁₂H₈N₂)₂].C₂H₆O₂(II)[Zhong et al., 2006]. The dihedral angle between the two chelating N₂C₂ groups is 80.06 (8)°, this is larger than that found in (II) [70.16 (6)°]. A twofold rotation axis (symmetry code: -x + 1, y, - z + 1/2) passes through the Co and S atoms, and also through the mid-carbon of the propane-1,3-diol solvent molecule. The crystal structure is further stabilized by intermolecular O3—H3B···O2 hydrogen bonds (Fig. 1 and Table 1).

Related literature top

For related cobalt compounds with monodentate, bidentate-bridging sulfate ligands, see: Hennig et al. (1975); Li et al. (1987); Song et al. (2008); Zheng & Lin (2003). For related complexes with bidentate-chelating ligands, see: Lu et al. (2006); Paul et al. (2002); Wang et al. (2009). For an isostructural structure, see: Zhong et al. (2006). For a related structure, see: Chen et al. (2005). For applications of transition metal complexes of phen, see: Li et al. (2004); Wang et al. (2000).

Experimental top

Red prism-shaped crystals of the title compound was unexpectedly obtained as a by-product during an attempt to synthesize a mixed-ligand cobalt complex with phen and melamine via a propane-1,3-diol/water solvothermal reaction. 0.2 mmol phen, 0.1 mmol melamine, 0.1 mmol CoSO₄.7H₂O, 2.0 ml 1,3-propanediol and 1.0 ml water were mixed and placed in a thick Pyrex tube, which was sealed and heated to 413 K for 96 h, whereupon red-prisms of the title complex were obtained.

Computing details top

Data collection: CrystalClear (Rigaku, 2007); cell refinement: CrystalClear (Rigaku, 2007); data reduction: CrystalClear (Rigaku, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title complex showing the atom-numbering scheme and with displacement ellipsoids drawn at the 50% probability level. The dashed lines represent O—H···O interactions. Unlabeled atoms are related to the labelled atoms by the symmetry operator (-x + 1, y, - z + 1/2).

Bis(1,10-phenanthroline-κ²N,N')(sulfato- κ²O,O')cobalt(II) propane-1,3-diol solvate top

Crystal data top

[Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	F(000) = 1220
M_r = 591.49	D_x = 1.541 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3592 reflections
a = 18.285 (4) Å	θ = 3.2–27.5°
b = 12.422 (3) Å	µ = 0.81 mm⁻¹
c = 13.211 (3) Å	T = 223 K
β = 121.82 (3)°	Prism, red
V = 2549.7 (13) Å³	0.60 × 0.40 × 0.34 mm
Z = 4

Data collection top

Rigaku Mercury CCD diffractometer	2898 independent reflections
Radiation source: fine-focus sealed tube	2540 reflections with I > 2σ(I)
Graphite Monochromator monochromator	R_int = 0.021
Detector resolution: 28.5714 pixels mm^-1	θ_max = 27.5°, θ_min = 3.2°
ω scans	h = −23→23
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	k = −16→13
T_min = 0.823, T_max = 1.000	l = −17→14
7099 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.101	w = 1/[σ²(F_o²) + (0.0616P)² + 1.0504P] where P = (F_o² + 2F_c²)/3
S = 1.06	(Δ/σ)_max < 0.001
2898 reflections	Δρ_max = 0.72 e Å⁻³
183 parameters	Δρ_min = −0.45 e Å⁻³
21 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (6)

Crystal data top

[Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂	V = 2549.7 (13) Å³
M_r = 591.49	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 18.285 (4) Å	µ = 0.81 mm⁻¹
b = 12.422 (3) Å	T = 223 K
c = 13.211 (3) Å	0.60 × 0.40 × 0.34 mm
β = 121.82 (3)°

Data collection top

Rigaku Mercury CCD diffractometer	2898 independent reflections
Absorption correction: multi-scan (REQAB: Jacobson, 1998)	2540 reflections with I > 2σ(I)
T_min = 0.823, T_max = 1.000	R_int = 0.021
7099 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	21 restraints
wR(F²) = 0.101	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.72 e Å⁻³
2898 reflections	Δρ_min = −0.45 e Å⁻³
183 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
Co1	0.5000	0.81835 (3)	0.2500	0.02201 (14)
S1	0.5000	1.03618 (5)	0.2500	0.02331 (17)
O1	0.44793 (9)	0.96187 (12)	0.14805 (12)	0.0329 (3)
C11	0.34382 (12)	0.68292 (14)	0.14757 (16)	0.0224 (4)
N2	0.40420 (10)	0.71189 (13)	0.12195 (14)	0.0238 (3)
C10	0.39507 (13)	0.67410 (16)	0.02169 (18)	0.0284 (4)
H10A	0.4356	0.6935	0.0028	0.034*
C8	0.26687 (13)	0.57717 (16)	−0.03144 (17)	0.0304 (4)
H8A	0.2213	0.5328	−0.0832	0.036*
O2	0.55612 (10)	1.10269 (14)	0.22920 (16)	0.0446 (4)
C6	0.21399 (13)	0.58852 (17)	0.10868 (18)	0.0310 (4)
H6A	0.1679	0.5434	0.0604	0.037*
C12	0.35267 (11)	0.72718 (15)	0.25388 (16)	0.0223 (4)
C7	0.27424 (12)	0.61511 (16)	0.07446 (17)	0.0264 (4)
C4	0.29234 (12)	0.69936 (16)	0.28497 (17)	0.0270 (4)
C9	0.32726 (14)	0.60646 (18)	−0.05671 (18)	0.0331 (4)
H9A	0.3235	0.5817	−0.1257	0.040*
C5	0.22322 (12)	0.62810 (18)	0.21042 (18)	0.0322 (5)
H5A	0.1841	0.6086	0.2319	0.039*
N1	0.41806 (10)	0.79727 (13)	0.31789 (14)	0.0250 (3)
C1	0.42581 (13)	0.84107 (17)	0.41526 (18)	0.0291 (4)
H1A	0.4706	0.8892	0.4597	0.035*
C2	0.36899 (14)	0.81726 (18)	0.45310 (19)	0.0335 (5)
H2A	0.3762	0.8491	0.5215	0.040*
C3	0.30319 (13)	0.74709 (18)	0.38888 (18)	0.0335 (5)
H3A	0.2653	0.7306	0.4135	0.040*
O3	0.56334 (16)	1.31539 (16)	0.1809 (2)	0.0659 (6)
H3B	0.5610	1.2514	0.1944	0.099*
C14	0.5000	1.4456 (3)	0.2500	0.0562 (10)
C13	0.5774 (2)	1.3764 (3)	0.2780 (3)	0.0723 (9)
H13A	0.6268	1.4227	0.3033	0.087*
H13B	0.5907	1.3286	0.3436	0.087*
H14	0.496 (3)	1.442 (4)	0.174 (2)	0.143 (19)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0211 (2)	0.0208 (2)	0.0239 (2)	0.000	0.01172 (16)	0.000
S1	0.0212 (3)	0.0200 (3)	0.0303 (3)	0.000	0.0146 (3)	0.000
O1	0.0315 (7)	0.0277 (8)	0.0270 (7)	0.0012 (6)	0.0068 (6)	0.0011 (6)
C11	0.0222 (9)	0.0193 (9)	0.0227 (9)	0.0027 (7)	0.0098 (7)	0.0026 (7)
N2	0.0253 (8)	0.0218 (8)	0.0254 (8)	0.0006 (6)	0.0141 (7)	0.0004 (6)
C10	0.0334 (10)	0.0272 (11)	0.0284 (10)	−0.0004 (8)	0.0189 (9)	−0.0014 (8)
C8	0.0306 (10)	0.0278 (11)	0.0241 (9)	−0.0033 (8)	0.0085 (8)	−0.0045 (8)
O2	0.0435 (9)	0.0362 (9)	0.0676 (12)	−0.0093 (8)	0.0386 (9)	0.0028 (8)
C6	0.0243 (9)	0.0314 (11)	0.0298 (10)	−0.0075 (8)	0.0092 (8)	0.0014 (8)
C12	0.0202 (8)	0.0222 (9)	0.0218 (8)	0.0026 (7)	0.0092 (7)	0.0028 (7)
C7	0.0251 (9)	0.0245 (10)	0.0247 (9)	0.0007 (8)	0.0098 (8)	0.0020 (7)
C4	0.0251 (9)	0.0291 (10)	0.0271 (9)	0.0023 (8)	0.0139 (8)	0.0045 (8)
C9	0.0397 (11)	0.0332 (11)	0.0252 (9)	0.0002 (9)	0.0162 (9)	−0.0043 (8)
C5	0.0259 (9)	0.0382 (12)	0.0328 (10)	−0.0041 (9)	0.0157 (8)	0.0046 (9)
N1	0.0249 (8)	0.0252 (8)	0.0253 (8)	0.0004 (6)	0.0135 (7)	−0.0008 (6)
C1	0.0304 (10)	0.0283 (11)	0.0270 (9)	−0.0003 (8)	0.0140 (8)	−0.0050 (8)
C2	0.0409 (12)	0.0361 (12)	0.0282 (10)	0.0029 (9)	0.0213 (10)	−0.0025 (8)
C3	0.0347 (10)	0.0419 (13)	0.0318 (10)	0.0004 (9)	0.0229 (9)	0.0030 (9)
O3	0.1116 (18)	0.0412 (11)	0.0867 (15)	−0.0012 (11)	0.0808 (15)	0.0034 (10)
C14	0.085 (3)	0.0301 (18)	0.068 (3)	0.000	0.050 (2)	0.000
C13	0.077 (2)	0.072 (2)	0.069 (2)	−0.0252 (18)	0.0392 (17)	−0.0071 (17)

Geometric parameters (Å, º) top

Co1—N1ⁱ	2.1295 (16)	C6—C7	1.432 (3)
Co1—N1	2.1295 (16)	C6—H6A	0.9300
Co1—O1ⁱ	2.1323 (15)	C12—N1	1.355 (3)
Co1—O1	2.1323 (15)	C12—C4	1.408 (3)
Co1—N2	2.1341 (17)	C4—C3	1.410 (3)
Co1—N2ⁱ	2.1341 (17)	C4—C5	1.428 (3)
Co1—S1	2.7058 (9)	C9—H9A	0.9300
S1—O2	1.4519 (15)	C5—H5A	0.9300
S1—O2ⁱ	1.4519 (15)	N1—C1	1.334 (3)
S1—O1	1.4901 (15)	C1—C2	1.401 (3)
S1—O1ⁱ	1.4901 (15)	C1—H1A	0.9300
C11—N2	1.363 (2)	C2—C3	1.360 (3)
C11—C7	1.402 (3)	C2—H2A	0.9300
C11—C12	1.436 (3)	C3—H3A	0.9300
N2—C10	1.330 (2)	O3—C13	1.392 (3)
C10—C9	1.401 (3)	O3—H3B	0.8200
C10—H10A	0.9300	C14—C13ⁱ	1.525 (4)
C8—C9	1.361 (3)	C14—C13	1.525 (4)
C8—C7	1.414 (3)	C14—H14	0.97 (3)
C8—H8A	0.9300	C13—H13A	0.9700
C6—C5	1.356 (3)	C13—H13B	0.9700

N1ⁱ—Co1—N1	165.87 (9)	C9—C8—H8A	120.4
N1ⁱ—Co1—O1ⁱ	100.94 (6)	C7—C8—H8A	120.4
N1—Co1—O1ⁱ	90.91 (6)	C5—C6—C7	120.98 (18)
N1ⁱ—Co1—O1	90.91 (6)	C5—C6—H6A	119.5
N1—Co1—O1	100.94 (6)	C7—C6—H6A	119.5
O1ⁱ—Co1—O1	66.54 (8)	N1—C12—C4	123.01 (17)
N1ⁱ—Co1—N2	93.19 (6)	N1—C12—C11	117.63 (16)
N1—Co1—N2	77.99 (6)	C4—C12—C11	119.33 (17)
O1ⁱ—Co1—N2	157.72 (6)	C11—C7—C8	117.41 (18)
O1—Co1—N2	96.36 (6)	C11—C7—C6	119.39 (18)
N1ⁱ—Co1—N2ⁱ	77.99 (6)	C8—C7—C6	123.19 (18)
N1—Co1—N2ⁱ	93.19 (6)	C12—C4—C3	116.81 (18)
O1ⁱ—Co1—N2ⁱ	96.36 (6)	C12—C4—C5	119.71 (18)
O1—Co1—N2ⁱ	157.72 (6)	C3—C4—C5	123.45 (18)
N2—Co1—N2ⁱ	103.42 (9)	C8—C9—C10	119.69 (19)
N1ⁱ—Co1—S1	97.06 (5)	C8—C9—H9A	120.2
N1—Co1—S1	97.06 (5)	C10—C9—H9A	120.2
O1ⁱ—Co1—S1	33.27 (4)	C6—C5—C4	120.73 (18)
O1—Co1—S1	33.27 (4)	C6—C5—H5A	119.6
N2—Co1—S1	128.29 (5)	C4—C5—H5A	119.6
N2ⁱ—Co1—S1	128.29 (5)	C1—N1—C12	118.30 (16)
O2—S1—O2ⁱ	110.64 (15)	C1—N1—Co1	127.99 (14)
O2—S1—O1	111.10 (9)	C12—N1—Co1	113.67 (12)
O2ⁱ—S1—O1	110.18 (9)	N1—C1—C2	122.42 (19)
O2—S1—O1ⁱ	110.18 (9)	N1—C1—H1A	118.8
O2ⁱ—S1—O1ⁱ	111.10 (9)	C2—C1—H1A	118.8
O1—S1—O1ⁱ	103.45 (12)	C3—C2—C1	119.41 (19)
O2—S1—Co1	124.68 (7)	C3—C2—H2A	120.3
O2ⁱ—S1—Co1	124.68 (7)	C1—C2—H2A	120.3
O1—S1—Co1	51.72 (6)	C2—C3—C4	120.05 (18)
O1ⁱ—S1—Co1	51.72 (6)	C2—C3—H3A	120.0
S1—O1—Co1	95.01 (7)	C4—C3—H3A	120.0
N2—C11—C7	123.19 (17)	C13—O3—H3B	109.5
N2—C11—C12	116.97 (16)	C13ⁱ—C14—C13	111.4 (3)
C7—C11—C12	119.82 (17)	C13ⁱ—C14—H14	100 (3)
C10—N2—C11	117.47 (17)	C13—C14—H14	77 (3)
C10—N2—Co1	128.88 (13)	O3—C13—C14	112.8 (2)
C11—N2—Co1	113.62 (12)	O3—C13—H13A	109.0
N2—C10—C9	123.06 (18)	C14—C13—H13A	109.0
N2—C10—H10A	118.5	O3—C13—H13B	109.0
C9—C10—H10A	118.5	C14—C13—H13B	109.0
C9—C8—C7	119.17 (19)	H13A—C13—H13B	107.8

N1ⁱ—Co1—S1—O2	−9.86 (10)	C11—N2—C10—C9	−0.4 (3)
N1—Co1—S1—O2	170.14 (10)	Co1—N2—C10—C9	−178.16 (15)
O1ⁱ—Co1—S1—O2	89.33 (12)	N2—C11—C12—N1	2.5 (3)
O1—Co1—S1—O2	−90.67 (12)	C7—C11—C12—N1	−176.19 (17)
N2—Co1—S1—O2	−109.61 (10)	N2—C11—C12—C4	−179.60 (17)
N2ⁱ—Co1—S1—O2	70.39 (10)	C7—C11—C12—C4	1.7 (3)
N1ⁱ—Co1—S1—O2ⁱ	170.14 (10)	N2—C11—C7—C8	−1.0 (3)
N1—Co1—S1—O2ⁱ	−9.86 (10)	C12—C11—C7—C8	177.62 (17)
O1ⁱ—Co1—S1—O2ⁱ	−90.67 (12)	N2—C11—C7—C6	179.73 (18)
O1—Co1—S1—O2ⁱ	89.33 (12)	C12—C11—C7—C6	−1.7 (3)
N2—Co1—S1—O2ⁱ	70.39 (10)	C9—C8—C7—C11	0.8 (3)
N2ⁱ—Co1—S1—O2ⁱ	−109.61 (10)	C9—C8—C7—C6	−179.9 (2)
N1ⁱ—Co1—S1—O1	80.81 (9)	C5—C6—C7—C11	0.1 (3)
N1—Co1—S1—O1	−99.19 (9)	C5—C6—C7—C8	−179.1 (2)
O1ⁱ—Co1—S1—O1	180.0	N1—C12—C4—C3	−0.9 (3)
N2—Co1—S1—O1	−18.94 (9)	C11—C12—C4—C3	−178.66 (17)
N2ⁱ—Co1—S1—O1	161.06 (9)	N1—C12—C4—C5	177.55 (18)
N1ⁱ—Co1—S1—O1ⁱ	−99.19 (9)	C11—C12—C4—C5	−0.2 (3)
N1—Co1—S1—O1ⁱ	80.81 (9)	C7—C8—C9—C10	−0.5 (3)
O1—Co1—S1—O1ⁱ	180.0	N2—C10—C9—C8	0.3 (3)
N2—Co1—S1—O1ⁱ	161.06 (9)	C7—C6—C5—C4	1.4 (3)
N2ⁱ—Co1—S1—O1ⁱ	−18.94 (9)	C12—C4—C5—C6	−1.3 (3)
O2—S1—O1—Co1	118.19 (9)	C3—C4—C5—C6	177.0 (2)
O2ⁱ—S1—O1—Co1	−118.83 (9)	C4—C12—N1—C1	0.6 (3)
O1ⁱ—S1—O1—Co1	0.0	C11—C12—N1—C1	178.38 (17)
N1ⁱ—Co1—O1—S1	−101.54 (8)	C4—C12—N1—Co1	178.28 (14)
N1—Co1—O1—S1	86.20 (8)	C11—C12—N1—Co1	−3.9 (2)
O1ⁱ—Co1—O1—S1	0.0	N1ⁱ—Co1—N1—C1	128.19 (17)
N2—Co1—O1—S1	165.15 (7)	O1ⁱ—Co1—N1—C1	−19.01 (17)
N2ⁱ—Co1—O1—S1	−42.22 (19)	O1—Co1—N1—C1	−85.28 (18)
C7—C11—N2—C10	0.7 (3)	N2—Co1—N1—C1	−179.54 (18)
C12—C11—N2—C10	−177.90 (17)	N2ⁱ—Co1—N1—C1	77.41 (18)
C7—C11—N2—Co1	178.87 (14)	S1—Co1—N1—C1	−51.81 (17)
C12—C11—N2—Co1	0.2 (2)	N1ⁱ—Co1—N1—C12	−49.27 (13)
N1ⁱ—Co1—N2—C10	−14.97 (17)	O1ⁱ—Co1—N1—C12	163.52 (13)
N1—Co1—N2—C10	176.18 (18)	O1—Co1—N1—C12	97.25 (14)
O1ⁱ—Co1—N2—C10	114.64 (19)	N2—Co1—N1—C12	2.99 (13)
O1—Co1—N2—C10	76.30 (17)	N2ⁱ—Co1—N1—C12	−100.06 (14)
N2ⁱ—Co1—N2—C10	−93.38 (17)	S1—Co1—N1—C12	130.73 (13)
S1—Co1—N2—C10	86.62 (17)	C12—N1—C1—C2	−0.1 (3)
N1ⁱ—Co1—N2—C11	167.15 (13)	Co1—N1—C1—C2	−177.43 (15)
N1—Co1—N2—C11	−1.71 (12)	N1—C1—C2—C3	−0.1 (3)
O1ⁱ—Co1—N2—C11	−63.2 (2)	C1—C2—C3—C4	−0.3 (3)
O1—Co1—N2—C11	−101.58 (13)	C12—C4—C3—C2	0.7 (3)
N2ⁱ—Co1—N2—C11	88.74 (13)	C5—C4—C3—C2	−177.6 (2)
S1—Co1—N2—C11	−91.26 (13)	C13ⁱ—C14—C13—O3	64.6 (2)

Symmetry code: (i) −x+1, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2	0.82	1.92	2.737 (3)	179

Experimental details

Crystal data
Chemical formula	[Co(SO₄)(C₁₂H₈N₂)₂]·C₃H₈O₂
M_r	591.49
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	223
a, b, c (Å)	18.285 (4), 12.422 (3), 13.211 (3)
β (°)	121.82 (3)
V (Å³)	2549.7 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.60 × 0.40 × 0.34

Data collection
Diffractometer	Rigaku Mercury CCD diffractometer
Absorption correction	Multi-scan (REQAB: Jacobson, 1998)
T_min, T_max	0.823, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7099, 2898, 2540
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.101, 1.06
No. of reflections	2898
No. of parameters	183
No. of restraints	21
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.72, −0.45

Computer programs: CrystalClear (Rigaku, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3B···O2	0.82	1.92	2.737 (3)	178.8

Acknowledgements

The work was supported by the Scientific Research Foundation of Nanjing College of Chemical Technology (grant No. NHKY-2010-17).

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