catena-Poly[[(dipyrido[3,2-a:2′,3′-c]phenazine)cobalt(II)]-μ-biphenyl-2,2′-dicarboxyl­ato]

Wei, F.; Wang, W.-J.; Jin, X.-J.; Mei, Z.-M.; Li, X.-P.

doi:10.1107/S1600536808001827

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 64| Part 2| February 2008| Page m379

doi:10.1107/S1600536808001827

Open

access

catena-Poly[[(dipyrido[3,2-a:2′,3′-c]phenazine)cobalt(II)]-μ-biphenyl-2,2′-dicarboxylato]

Fang Wei,^a Wen-Ju Wang,^a Xiang-Jun Jin,^a Ze-Min Mei ^a ^* and Xiao-Ping Li ^a

^aDepartment of Chemistry, Baicheng Normal College, Baicheng 137000, People's Republic of China
^*Correspondence e-mail: fangwei1026@yahoo.com.cn

(Received 15 January 2008; accepted 17 January 2008; online 23 January 2008)

In the title compound, [Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]_n, the Co^II atom is six-coordinated by four O atoms from two different biphenyl-2,2′-dicarboxylate ligands and two N atoms from the bidentate dipyrido[3,2-a:2′,3′-c]phenazine ligand in a distorted octahedral geometry. The Co^II atoms are bridged by the biphenyl-2,2′-dicarboxylate ligands to form a one-dimensional chain structure. π–π interactions between neighbouring chains result in a two-dimensional supramolecular network (centroid-to-centroid separation = 3.381 Å).

Related literature

For related literature, see: Hao et al. (2004 ); Li et al. (2006 ); Noveron et al. (2002 ); Dickeson & Summers (1970 ); Li et al. (2007 ); Zhang et al. (2001 ).

Experimental

Crystal data

[Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]
M_r = 581.43
Monoclinic, P 2₁ /c
a = 9.311 (4) Å
b = 12.521 (5) Å
c = 21.831 (10) Å
β = 102.31°
V = 2486.5 (19) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 293 (2) K
0.43 × 0.11 × 0.07 mm

Data collection

Bruker APEXII diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2002 ) T_min = 0.904, T_max = 0.951
13141 measured reflections
5022 independent reflections
1796 reflections with I > 2σ(I)
R_int = 0.085

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.085
S = 0.87
5022 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.92 e Å⁻³
Δρ_min = −0.30 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—O3ⁱ	2.087 (3)
Co1—N2	2.093 (4)
Co1—O1	2.105 (3)
Co1—N1	2.115 (4)
Co1—O2	2.151 (3)
Co1—O4ⁱ	2.185 (3)

N2—Co1—O1	95.31 (15)
N2—Co1—N1	78.05 (16)
O1—Co1—N1	159.78 (13)
N2—Co1—O2	97.96 (13)
O1—Co1—O2	61.86 (10)
N1—Co1—O2	99.79 (13)
Symmetry code: (i) $[-x, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: APEX2 (Bruker, 2006 ); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808001827/at2538sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808001827/at2538Isup2.hkl

checkCIF report

Comment top

Metal-organic hybrid compounds have attracted considerable interest and importance in recent years, not only due to their intriguing structural motifs but also their potential applications in areas such as catalysis, medicine and host–guest chemistry (Hao et al., 2004). The chelating ligand 1,10-phenanthroline (phen) and its derivatives have been widely used in the construction of metal-organic coordination polymers (Li et al., 2006). On the other hand, carboxylate ligands have already been proven to be efficient for the generation of a helical coordination polymer (Li et al., 2007), so we reacted dipydo[3,2 - a:2',3'-c]phenazine with cobalt and biphenyl-2,2'-dicarboxylate, resulting in the title molecular complex, [Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]_n, (I)

Compound (I) is a one-dimensional chain structure, which is constructed from one Co^II atom, one L ligand and two biphenyl-2,2'-dicarboxylate dianion (Fig. 1). The Co^II center is six-coordinated by two N atoms from the bidentate L ligand and four O atoms from two different 2,6'-biphenyl dicarboxylic acid ligands to result in a substantially distorted cis-CoN₂O₄ octahedron. The mean Co—O and Co—N distances are 2.112 (3) and 2.104 (4) Å, respectively. The C—O bond lengths of the 2,6'-biphenyl dicarboxylic acid groups imply electronic delocalizations of the negative charges.

Neighboring Co^II atoms are bridged by the biphenyl-2,2'-dicarboxylate ligands, forming a one-dimensional chain structure as shown in (Fig. 2). Then, neighbouring chains are connected by π-π interactions, generating a two-dimensional supramolecular structure (Fig. 3). The π-π stacking distances are 3.381Å between L ligands. Similar values are seen in related structures (Noveron et al., 2002).

Related literature top

For related literature, see: Hao et al. (2004); Li et al. (2006); Noveron et al. (2002); Dickeson & Summers (1970); Li et al. (2007); Zhang et al. (2001).

Experimental top

The L ligand was synthesized by the literature method of Dickeson & Summers (1970). A mixture of CoCl₂.2H₂O (0.3 mmol), L (0.1 mmol) and 2,6'-biphenyl dicarboxylic acid (0.3 mmol) in 30 ml of distilled water was stirred thoroughly for 1 h at ambient temperature. The pH value was adjusted to about 7.5 with NaOH aqueous solution. The suspension was sealed in a Teflon-lined stainless reaction vessel (40 ml) and heated at 443 K for 5 days. The vessel was cooled slowly to room temperature at a rate of 10 K h^-1 before opening and yellow crystals of (I) were collected.

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: SAINT (Bruker, 2002); data reduction: SAINT (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL-Plus (Sheldrick, 2008); software used to prepare material for publication: SHELXTL-Plus (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit of (I), together with additional atoms to complete the coordination of Co1 with displacement ellipsoids drawn at the 30% probability level (arbitrary spheres for the H atoms). Symmetry codes: (i) -x, -y + 1/2, -z + 1/2; (ii) -x, y - 1/2, -z + 1/2.
	Fig. 2. A view of the one-chain structure of (I). H atoms have been omitted for clarity.
	Fig. 3. View of the two-dimensional supramolecular structure of (I) generated by π-π interations. H atoms have been omitted for clarity.

catena-Poly[[(dipyrido[3,2 - a:2',3'-c]phenazine)cobalt(II)]-µ-biphenyl-2,2'- dicarboxylato] top

Crystal data top

[Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]	F(000) = 1188.0
M_r = 581.43	D_x = 1.553 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 2096 reflections
a = 9.311 (4) Å	θ = 2.3–26.0°
b = 12.521 (5) Å	µ = 0.74 mm⁻¹
c = 21.831 (10) Å	T = 293 K
β = 102.31°	Block, amethyst
V = 2486.5 (19) Å³	0.44 × 0.11 × 0.07 mm
Z = 4

Data collection top

Bruker APEXII diffractometer	5022 independent reflections
Radiation source: fine-focus sealed tube	1796 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.085
Detector resolution: 0 pixels mm^-1	θ_max = 26.2°, θ_min = 1.9°
not measured scans	h = −9→11
Absorption correction: multi-scan (SADABS; Bruker, 2002)	k = −15→15
T_min = 0.904, T_max = 0.951	l = −27→18
13141 measured reflections

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)] = 0.048	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	w = 1/[σ²(F_o²) + (0.002P)²] where P = (F_o² + 2F_c²)/3
5022 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.92 e Å⁻³
0 restraints	Δρ_min = −0.30 e Å⁻³

Crystal data top

[Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]	V = 2486.5 (19) Å³
M_r = 581.43	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 9.311 (4) Å	µ = 0.74 mm⁻¹
b = 12.521 (5) Å	T = 293 K
c = 21.831 (10) Å	0.44 × 0.11 × 0.07 mm
β = 102.31°

Data collection top

Bruker APEXII diffractometer	5022 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2002)	1796 reflections with I > 2σ(I)
T_min = 0.904, T_max = 0.951	R_int = 0.085
13141 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	0 restraints
wR(F²) = 0.085	H-atom parameters constrained
S = 0.87	Δρ_max = 0.92 e Å⁻³
5022 reflections	Δρ_min = −0.30 e Å⁻³
370 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	0.02037 (7)	0.27680 (5)	0.19183 (3)	0.0511 (2)
O1	0.1414 (3)	0.2191 (3)	0.27808 (13)	0.0644 (10)
O2	−0.0977 (3)	0.2343 (2)	0.26292 (13)	0.0526 (9)
N2	0.0064 (4)	0.1293 (3)	0.14589 (18)	0.0486 (11)
C5	−0.3420 (5)	0.1185 (4)	−0.0118 (2)	0.0458 (13)
N1	−0.1583 (4)	0.3017 (3)	0.11521 (17)	0.0496 (11)
C4	−0.3106 (5)	0.2151 (4)	0.0256 (2)	0.0455 (13)
C12	−0.2475 (5)	0.0282 (4)	0.0016 (2)	0.0449 (13)
N4	−0.4625 (4)	0.1169 (3)	−0.05836 (18)	0.0521 (12)
C13	−0.1245 (5)	0.0309 (4)	0.0561 (2)	0.0454 (13)
N3	−0.2692 (4)	−0.0605 (3)	−0.03208 (19)	0.0512 (11)
C18	−0.1927 (5)	0.2156 (4)	0.0769 (2)	0.0436 (12)
C17	−0.1001 (5)	0.1222 (4)	0.0925 (2)	0.0422 (13)
C19	0.0254 (5)	0.2107 (4)	0.2984 (2)	0.0457 (13)
C6	−0.4883 (5)	0.0253 (5)	−0.0920 (2)	0.0519 (14)
C20	0.0350 (5)	0.1783 (3)	0.3653 (2)	0.0395 (12)
C31	−0.2806 (5)	0.0171 (4)	0.3290 (2)	0.0454 (13)
C26	−0.2356 (5)	0.1185 (4)	0.3516 (2)	0.0461 (13)
C11	−0.3907 (6)	−0.0624 (4)	−0.0800 (2)	0.0526 (14)
C23	0.0737 (5)	0.1393 (4)	0.4925 (2)	0.0661 (16)
H23A	0.0846	0.1279	0.5354	0.079*
C21	0.1700 (5)	0.1932 (3)	0.4056 (2)	0.0498 (14)
H21A	0.2490	0.2170	0.3894	0.060*
C3	−0.3955 (5)	0.3080 (4)	0.0141 (2)	0.0569 (15)
H3B	−0.4744	0.3108	−0.0201	0.068*
C25	−0.0827 (5)	0.1402 (4)	0.3883 (2)	0.0454 (13)
C24	−0.0610 (5)	0.1215 (4)	0.4522 (2)	0.0587 (15)
H24A	−0.1390	0.0963	0.4686	0.070*
C30	−0.4302 (6)	−0.0057 (4)	0.3079 (2)	0.0628 (16)
H30A	−0.4597	−0.0743	0.2944	0.075*
C7	−0.6179 (5)	0.0173 (4)	−0.1408 (2)	0.0602 (16)
H7A	−0.6833	0.0743	−0.1490	0.072*
C14	−0.0337 (5)	−0.0574 (4)	0.0756 (2)	0.0569 (15)
H14A	−0.0458	−0.1199	0.0520	0.068*
C27	−0.3441 (6)	0.1970 (4)	0.3493 (2)	0.0624 (15)
H27A	−0.3163	0.2656	0.3634	0.075*
C2	−0.3632 (5)	0.3954 (4)	0.0528 (2)	0.0692 (17)
H2B	−0.4201	0.4570	0.0460	0.083*
C16	0.0876 (5)	0.0434 (5)	0.1629 (2)	0.0578 (15)
H16A	0.1594	0.0471	0.1997	0.069*
C1	−0.2411 (5)	0.3880 (4)	0.1032 (2)	0.0574 (15)
H1B	−0.2174	0.4469	0.1294	0.069*
C10	−0.4203 (6)	−0.1538 (4)	−0.1182 (3)	0.0649 (16)
H10A	−0.3551	−0.2110	−0.1123	0.078*
C15	0.0737 (5)	−0.0517 (4)	0.1299 (3)	0.0635 (16)
H15A	0.1344	−0.1097	0.1438	0.076*
C22	0.1907 (5)	0.1739 (4)	0.4688 (2)	0.0571 (15)
H22A	0.2823	0.1840	0.4951	0.069*
C29	−0.5345 (6)	0.0734 (5)	0.3071 (2)	0.0678 (16)
H29A	−0.6337	0.0578	0.2932	0.081*
C28	−0.4916 (6)	0.1750 (5)	0.3267 (2)	0.0697 (17)
H28A	−0.5613	0.2287	0.3248	0.084*
C8	−0.6444 (6)	−0.0731 (5)	−0.1747 (2)	0.0716 (18)
H8A	−0.7299	−0.0790	−0.2055	0.086*
C9	−0.5458 (7)	−0.1579 (5)	−0.1642 (2)	0.0695 (17)
H9A	−0.5655	−0.2188	−0.1890	0.083*
C32	−0.1725 (6)	−0.0692 (4)	0.3244 (2)	0.0483 (14)
O3	−0.1965 (3)	−0.1613 (3)	0.34207 (15)	0.0616 (10)
O4	−0.0650 (3)	−0.0519 (2)	0.30026 (15)	0.0594 (10)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0506 (4)	0.0622 (5)	0.0386 (4)	−0.0010 (4)	0.0055 (3)	0.0012 (4)
O1	0.0366 (19)	0.114 (3)	0.044 (2)	0.004 (2)	0.0134 (17)	0.015 (2)
O2	0.0424 (19)	0.076 (2)	0.038 (2)	0.0024 (18)	0.0062 (16)	0.0077 (18)
N2	0.050 (3)	0.051 (3)	0.043 (3)	0.000 (2)	0.004 (2)	0.005 (2)
C5	0.039 (3)	0.064 (4)	0.036 (3)	−0.006 (3)	0.013 (3)	0.007 (3)
N1	0.048 (3)	0.059 (3)	0.040 (3)	0.005 (2)	0.006 (2)	0.000 (2)
C4	0.036 (3)	0.060 (4)	0.040 (3)	−0.003 (3)	0.006 (2)	0.002 (3)
C12	0.043 (3)	0.056 (4)	0.038 (3)	−0.008 (3)	0.013 (3)	0.004 (3)
N4	0.046 (3)	0.072 (3)	0.039 (3)	−0.008 (2)	0.009 (2)	0.001 (2)
C13	0.042 (3)	0.054 (4)	0.042 (3)	−0.003 (3)	0.014 (3)	0.006 (3)
N3	0.051 (3)	0.060 (3)	0.045 (3)	−0.013 (2)	0.015 (2)	−0.006 (2)
C18	0.040 (3)	0.056 (4)	0.036 (3)	−0.005 (3)	0.012 (2)	0.001 (3)
C17	0.039 (3)	0.051 (4)	0.039 (3)	−0.005 (3)	0.014 (3)	0.007 (3)
C19	0.047 (3)	0.046 (3)	0.043 (3)	−0.002 (3)	0.007 (3)	−0.005 (3)
C6	0.051 (4)	0.066 (4)	0.040 (4)	−0.015 (3)	0.014 (3)	−0.002 (3)
C20	0.038 (3)	0.047 (3)	0.031 (3)	0.001 (3)	0.001 (2)	0.000 (2)
C31	0.039 (3)	0.062 (4)	0.035 (3)	−0.001 (3)	0.008 (3)	0.002 (3)
C26	0.039 (3)	0.066 (4)	0.037 (3)	0.003 (3)	0.014 (3)	0.009 (3)
C11	0.060 (4)	0.063 (4)	0.041 (4)	−0.022 (3)	0.025 (3)	−0.004 (3)
C23	0.063 (4)	0.097 (5)	0.035 (3)	0.011 (4)	0.003 (3)	0.007 (3)
C21	0.049 (3)	0.060 (4)	0.041 (3)	−0.003 (3)	0.012 (3)	−0.005 (3)
C3	0.042 (3)	0.072 (4)	0.052 (4)	0.004 (3)	0.001 (3)	0.004 (3)
C25	0.040 (3)	0.055 (3)	0.041 (3)	0.003 (3)	0.005 (3)	0.001 (3)
C24	0.049 (3)	0.084 (4)	0.043 (4)	−0.005 (3)	0.011 (3)	0.004 (3)
C30	0.056 (4)	0.076 (4)	0.056 (4)	−0.003 (3)	0.010 (3)	0.004 (3)
C7	0.052 (4)	0.084 (5)	0.043 (4)	−0.016 (3)	0.009 (3)	0.004 (3)
C14	0.053 (3)	0.062 (4)	0.060 (4)	−0.010 (3)	0.022 (3)	−0.002 (3)
C27	0.053 (4)	0.069 (4)	0.067 (4)	0.003 (3)	0.018 (3)	0.002 (3)
C2	0.066 (4)	0.069 (4)	0.065 (4)	−0.002 (3)	−0.003 (3)	−0.011 (4)
C16	0.051 (3)	0.072 (4)	0.048 (4)	0.005 (3)	0.007 (3)	0.008 (4)
C1	0.058 (4)	0.057 (4)	0.055 (4)	0.011 (3)	0.009 (3)	−0.014 (3)
C10	0.076 (4)	0.068 (4)	0.058 (4)	−0.015 (3)	0.029 (3)	−0.010 (3)
C15	0.062 (4)	0.061 (4)	0.068 (4)	0.001 (3)	0.016 (3)	0.001 (4)
C22	0.047 (3)	0.074 (4)	0.046 (4)	0.002 (3)	−0.001 (3)	−0.002 (3)
C29	0.037 (3)	0.103 (5)	0.062 (4)	−0.004 (4)	0.006 (3)	0.006 (4)
C28	0.048 (4)	0.091 (5)	0.073 (4)	0.011 (4)	0.019 (3)	0.007 (4)
C8	0.074 (5)	0.097 (5)	0.044 (4)	−0.028 (4)	0.011 (3)	0.004 (4)
C9	0.090 (5)	0.079 (5)	0.042 (4)	−0.034 (4)	0.019 (4)	−0.016 (3)
C32	0.052 (4)	0.056 (4)	0.032 (3)	−0.001 (4)	−0.002 (3)	−0.007 (3)
O3	0.066 (2)	0.057 (2)	0.070 (3)	0.004 (2)	0.032 (2)	0.006 (2)
O4	0.050 (2)	0.068 (3)	0.063 (2)	0.003 (2)	0.019 (2)	0.004 (2)

Geometric parameters (Å, º) top

Co1—O3ⁱ	2.087 (3)	C23—C22	1.372 (5)
Co1—N2	2.093 (4)	C23—C24	1.388 (5)
Co1—O1	2.105 (3)	C23—H23A	0.9300
Co1—N1	2.115 (4)	C21—C22	1.374 (5)
Co1—O2	2.151 (3)	C21—H21A	0.9300
Co1—O4ⁱ	2.185 (3)	C3—C2	1.376 (5)
Co1—C19	2.460 (5)	C3—H3B	0.9300
Co1—C32ⁱ	2.463 (6)	C25—C24	1.386 (5)
O1—C19	1.256 (4)	C24—H24A	0.9300
O2—C19	1.274 (4)	C30—C29	1.384 (6)
N2—C16	1.322 (5)	C30—H30A	0.9300
N2—C17	1.363 (5)	C7—C8	1.346 (6)
C5—N4	1.344 (5)	C7—H7A	0.9300
C5—C12	1.424 (6)	C14—C15	1.381 (6)
C5—C4	1.454 (6)	C14—H14A	0.9300
N1—C1	1.322 (5)	C27—C28	1.384 (6)
N1—C18	1.360 (5)	C27—H27A	0.9300
C4—C18	1.391 (5)	C2—C1	1.406 (5)
C4—C3	1.398 (5)	C2—H2B	0.9300
C12—N3	1.323 (5)	C16—C15	1.383 (5)
C12—C13	1.465 (5)	C16—H16A	0.9300
N4—C6	1.355 (5)	C1—H1B	0.9300
C13—C17	1.384 (6)	C10—C9	1.369 (6)
C13—C14	1.402 (6)	C10—H10A	0.9300
N3—C11	1.367 (5)	C15—H15A	0.9300
C18—C17	1.450 (6)	C22—H22A	0.9300
C19—C20	1.501 (6)	C29—C28	1.374 (6)
C6—C11	1.414 (6)	C29—H29A	0.9300
C6—C7	1.432 (6)	C28—H28A	0.9300
C20—C25	1.384 (5)	C8—C9	1.390 (6)
C20—C21	1.385 (5)	C8—H8A	0.9300
C31—C26	1.394 (6)	C9—H9A	0.9300
C31—C30	1.400 (5)	C32—O4	1.246 (5)
C31—C32	1.494 (6)	C32—O3	1.252 (5)
C26—C27	1.403 (5)	C32—Co1ⁱⁱ	2.463 (6)
C26—C25	1.502 (5)	O3—Co1ⁱⁱ	2.087 (3)
C11—C10	1.409 (6)	O4—Co1ⁱⁱ	2.185 (3)

O3ⁱ—Co1—N2	97.50 (14)	C31—C26—C27	117.8 (5)
O3ⁱ—Co1—O1	97.66 (12)	C31—C26—C25	122.2 (5)
N2—Co1—O1	95.31 (15)	C27—C26—C25	119.0 (5)
O3ⁱ—Co1—N1	102.12 (13)	N3—C11—C10	119.5 (6)
N2—Co1—N1	78.05 (16)	N3—C11—C6	121.5 (5)
O1—Co1—N1	159.78 (13)	C10—C11—C6	119.0 (5)
O3ⁱ—Co1—O2	155.35 (12)	C22—C23—C24	119.6 (5)
N2—Co1—O2	97.96 (13)	C22—C23—H23A	120.2
O1—Co1—O2	61.86 (10)	C24—C23—H23A	120.2
N1—Co1—O2	99.79 (13)	C22—C21—C20	121.8 (5)
O3ⁱ—Co1—O4ⁱ	60.87 (12)	C22—C21—H21A	119.1
N2—Co1—O4ⁱ	153.61 (14)	C20—C21—H21A	119.1
O1—Co1—O4ⁱ	102.11 (12)	C2—C3—C4	120.6 (5)
N1—Co1—O4ⁱ	91.27 (14)	C2—C3—H3B	119.7
O2—Co1—O4ⁱ	107.67 (12)	C4—C3—H3B	119.7
O3ⁱ—Co1—C19	127.04 (14)	C20—C25—C24	117.8 (4)
N2—Co1—C19	98.21 (15)	C20—C25—C26	127.0 (4)
O1—Co1—C19	30.71 (11)	C24—C25—C26	115.1 (4)
N1—Co1—C19	130.56 (15)	C25—C24—C23	121.9 (5)
O2—Co1—C19	31.16 (11)	C25—C24—H24A	119.0
O4ⁱ—Co1—C19	106.91 (14)	C23—C24—H24A	119.0
O3ⁱ—Co1—C32ⁱ	30.54 (13)	C29—C30—C31	120.3 (5)
N2—Co1—C32ⁱ	126.93 (16)	C29—C30—H30A	119.9
O1—Co1—C32ⁱ	100.54 (13)	C31—C30—H30A	119.9
N1—Co1—C32ⁱ	98.65 (15)	C8—C7—C6	119.6 (5)
O2—Co1—C32ⁱ	134.08 (15)	C8—C7—H7A	120.2
O4ⁱ—Co1—C32ⁱ	30.36 (12)	C6—C7—H7A	120.2
C19—Co1—C32ⁱ	120.29 (15)	C15—C14—C13	120.0 (5)
C19—O1—Co1	90.5 (3)	C15—C14—H14A	120.0
C19—O2—Co1	87.9 (3)	C13—C14—H14A	120.0
C16—N2—C17	117.1 (4)	C28—C27—C26	121.7 (5)
C16—N2—Co1	127.6 (4)	C28—C27—H27A	119.2
C17—N2—Co1	115.3 (3)	C26—C27—H27A	119.2
N4—C5—C12	121.5 (5)	C3—C2—C1	117.6 (5)
N4—C5—C4	118.2 (5)	C3—C2—H2B	121.2
C12—C5—C4	120.3 (5)	C1—C2—H2B	121.2
C1—N1—C18	118.4 (4)	N2—C16—C15	124.8 (5)
C1—N1—Co1	127.2 (4)	N2—C16—H16A	117.6
C18—N1—Co1	114.3 (3)	C15—C16—H16A	117.6
C18—C4—C3	117.4 (5)	N1—C1—C2	123.3 (5)
C18—C4—C5	119.0 (5)	N1—C1—H1B	118.3
C3—C4—C5	123.5 (4)	C2—C1—H1B	118.3
N3—C12—C5	122.5 (5)	C9—C10—C11	119.5 (5)
N3—C12—C13	118.1 (5)	C9—C10—H10A	120.2
C5—C12—C13	119.3 (5)	C11—C10—H10A	120.2
C5—N4—C6	116.5 (4)	C14—C15—C16	117.5 (5)
C17—C13—C14	117.5 (5)	C14—C15—H15A	121.2
C17—C13—C12	119.3 (5)	C16—C15—H15A	121.2
C14—C13—C12	123.0 (5)	C23—C22—C21	118.9 (4)
C12—N3—C11	116.3 (4)	C23—C22—H22A	120.6
N1—C18—C4	122.7 (5)	C21—C22—H22A	120.6
N1—C18—C17	116.4 (4)	C28—C29—C30	120.1 (5)
C4—C18—C17	120.9 (5)	C28—C29—H29A	119.9
N2—C17—C13	123.1 (5)	C30—C29—H29A	119.9
N2—C17—C18	115.9 (5)	C29—C28—C27	119.7 (5)
C13—C17—C18	121.0 (5)	C29—C28—H28A	120.1
O1—C19—O2	119.7 (4)	C27—C28—H28A	120.1
O1—C19—C20	119.3 (4)	C7—C8—C9	121.0 (6)
O2—C19—C20	120.9 (4)	C7—C8—H8A	119.5
O1—C19—Co1	58.8 (2)	C9—C8—H8A	119.5
O2—C19—Co1	60.9 (2)	C10—C9—C8	121.5 (6)
C20—C19—Co1	175.4 (3)	C10—C9—H9A	119.2
N4—C6—C11	121.6 (5)	C8—C9—H9A	119.2
N4—C6—C7	119.1 (5)	O4—C32—O3	120.2 (5)
C11—C6—C7	119.3 (5)	O4—C32—C31	121.1 (5)
C25—C20—C21	119.9 (4)	O3—C32—C31	118.6 (5)
C25—C20—C19	124.0 (4)	O4—C32—Co1ⁱⁱ	62.4 (3)
C21—C20—C19	116.0 (4)	O3—C32—Co1ⁱⁱ	57.9 (3)
C26—C31—C30	120.3 (5)	C31—C32—Co1ⁱⁱ	172.7 (3)
C26—C31—C32	121.8 (5)	C32—O3—Co1ⁱⁱ	91.6 (3)
C30—C31—C32	117.9 (5)	C32—O4—Co1ⁱⁱ	87.3 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₁₄H₈O₄)(C₁₈H₁₀N₄)]
M_r	581.43
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	9.311 (4), 12.521 (5), 21.831 (10)
β (°)	102.31
V (Å³)	2486.5 (19)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.44 × 0.11 × 0.07

Data collection
Diffractometer	Bruker APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2002)
T_min, T_max	0.904, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	13141, 5022, 1796
R_int	0.085
(sin θ/λ)_max (Å⁻¹)	0.622

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.085, 0.87
No. of reflections	5022
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.92, −0.30

Computer programs: APEX2 (Bruker, 2006), SAINT (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL-Plus (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—O3ⁱ	2.087 (3)	Co1—N1	2.115 (4)
Co1—N2	2.093 (4)	Co1—O2	2.151 (3)
Co1—O1	2.105 (3)	Co1—O4ⁱ	2.185 (3)

N2—Co1—O1	95.31 (15)	N2—Co1—O2	97.96 (13)
N2—Co1—N1	78.05 (16)	O1—Co1—O2	61.86 (10)
O1—Co1—N1	159.78 (13)	N1—Co1—O2	99.79 (13)

Symmetry code: (i) −x, y+1/2, −z+1/2.

Acknowledgements

The authors thank Baicheng Normal College for supporting this work.

References

Bruker (2002). SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2006). APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dickeson, J. E. & Summers, L. A. (1970). Aust. J. Chem. 23, 1023–1027. CrossRef CAS Web of Science Google Scholar
Hao, N., Shen, E.-H., Li, Y.-G., Wang, E.-B., Hu, C.-W. & Xu, L. (2004). Inorg. Chem. Commun. 7, 510–512. Web of Science CSD CrossRef CAS Google Scholar
Li, C.-B., Fang, W., Dong, E.-J., Liu, B. & Li, Y.-W. (2007). Acta Cryst. E63, m150–m152. Web of Science CSD CrossRef IUCr Journals Google Scholar
Li, C.-B., Fang, W., Gao, G.-G. & Liu, B. (2006). Acta Cryst. E62, m1312–m1314. Web of Science CSD CrossRef IUCr Journals Google Scholar
Noveron, J. C., Lah, M. S., Sesto, R. E. D., Arif, A. M., Miller, J. S. & Stang, P. J. (2002). J. Am. Chem. Soc. 124, 6613–6625. Web of Science CSD CrossRef PubMed CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zhang, H. X., Kang, B. S., Xu, A. W., Chen, Z. N., Zhou, Z. Y., Yu, K. B. & Ren, C. (2001). J. Chem. Soc. Dalton Trans. pp. 2559–2566. Web of Science CSD CrossRef Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.