Poly[[tris­(N,N-dimethyl­formamide)(μ4-5-nitro­isophthalato)(μ3-5-nitro­isophthalato)dicobalt(II)] N,N-dimethyl­formamide monosolvate]

Su, M.; Huang, Z.-D.; Sun, H.; Yang, G.; Ng, S.W.

doi:10.1107/S1600536810035270

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 66| Part 10| October 2010| Pages m1220-m1221

doi:10.1107/S1600536810035270

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Poly[[tris(N,N-dimethylformamide)(μ₄-5-nitroisophthalato)(μ₃-5-nitroisophthalato)dicobalt(II)] N,N-dimethylformamide monosolvate]

Meng Su,^a Zhan-Dong Huang,^a Huang Sun,^a Guang Yang ^a and Seik Weng Ng ^b ^*

^aDepartment of Chemistry, Zhengzhou University, Zhengzhou 450001, People's Republic of China, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: seikweng@um.edu.my

(Received 31 August 2010; accepted 1 September 2010; online 8 September 2010)

In the polymeric title compound, [Co₂(C₃H₇NO)₃(C₈H₃NO₆)₂]·C₃H₇NO, one 5-nitroisophthalate dianion has its two carboxylate groups chelating to one Co^II atom while simultaneously coordinating to another metal atom in a μ₄-bridging mode. The other 5-nitroisophthalte dianion has one carboxylate group chelating to a metal atom whereas the other bridges two metal atoms in a μ₃-bridging mode. Both metal atoms show an octahedral coordination. The polymer adopts a layer motif, with the lattice dimethylformamide molecules occupying the space between adjacent layers.

Related literature

For adducts of cobalt 5-nitroisophthalate, see: Chen et al. (2006 ); Du et al. (2008 ); Guo et al. (2006 ); Liu et al. (2008 ); Luo et al. (2003 ); Wang et al. (2008 , 2009 ); Xie et al. (2006 ); Ye et al. (2008a ,b ); Yuan et al. (2009 ); Zhou et al. (2004 ).

Experimental

Crystal data

[Co₂(C₃H₇NO)₃(C₈H₃NO₆)₂]·C₃H₇NO
M_r = 828.47
Monoclinic, P 2₁ /c
a = 10.0833 (12) Å
b = 17.0887 (19) Å
c = 21.074 (2) Å
β = 92.910 (2)°
V = 3626.7 (7) Å³
Z = 4
Mo Kα radiation
μ = 0.99 mm⁻¹
T = 293 K
0.40 × 0.30 × 0.30 mm

Data collection

Bruker SMART diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.796, T_max = 1
21143 measured reflections
7876 independent reflections
5128 reflections with I > 2σ(I)
R_int = 0.036

Refinement

R[F² > 2σ(F²)] = 0.048
wR(F²) = 0.132
S = 0.99
7876 reflections
477 parameters
54 restraints
H-atom parameters constrained
Δρ_max = 0.57 e Å⁻³
Δρ_min = −0.45 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—O1	2.001 (2)
Co1—O3ⁱ	2.247 (2)
Co1—O4ⁱ	2.058 (2)
Co1—O7	2.383 (3)
Co1—O8	2.082 (3)
Co1—O10ⁱⁱ	2.008 (2)
Co2—O2	2.042 (2)
Co2—O7	2.091 (2)
Co2—O9ⁱⁱ	2.082 (2)
Co2—O13	2.139 (3)
Co2—O14	2.100 (2)
Co2—O15	2.063 (2)
Symmetry codes: (i) x-1, y, z; (ii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Data collection: SMART (Bruker, 1999 ); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003 ) and X-SEED (Barbour, 2001 ); software used to prepare material for publication: publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810035270/bt5344sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536810035270/bt5344Isup2.hkl

checkCIF report

Comment top

Cobalt 5-nitroisophthalate forms a number of adducts with neutral ligands (Chen et al., 2006; Du et al., 2008; Guo et al., 2006; Liu et al., 2008; Luo et al., 2003; Wang et al., 2008; Wang et al., 2009; Xie et al., 2006; Ye et al., 2008a; Ye et al., 2008b; Yuan et al., 2009; Zhou et al., 2004). The structure of the parent coordination polymer has not been reported. The attempt to synthesize this compound by using DMF as the solvent gave instead the DMF-coordinated polymer, who crystallizes as a DMF solvate (Scheme I).

In polymeric Co₂(DFM)₃(C₈H₃NO₆)₂^.DMF, the 5-nitroisophthalate units show different binding modes. With one dianion, each carboxyl –CO₂ fragment chelate to one cobalt(II) atom while simultaneously coordinating to another metal atom, i.e., this dianion functions in a µ₄-bridging mode. With the other, one carboxyl fragment chelates to a metal atom whereas the other bridges two metal atoms, the dianion functioning in a µ₃-bridging mode. Both metal atoms show octahedral coordination. Of the two indepent metal atoms, one is coordinated by three DMF molecules. The bridging mode exercised by the dianion gives rise to a layer motif (Fig. 1). The lattice DMF molecules occupy the space between adjacent layers.

Related literature top

For adducts of cobalt 5-nitroisophthalate, see: Chen et al. (2006); Du et al. (2008); Guo et al. (2006); Liu et al. (2008); Luo et al. (2003); Wang et al. (2008, 2009); Xie et al. (2006); Ye et al. (2008a,b); Yuan et al. (2009); Zhou et al. (2004).

Experimental top

Cobalt(II) nitrate hexahydrate (0.5 mmol, 0.146 g) and 5-nitroisophthalic acid (0.5 mmol, 0.106 g) were dissolved in DMF (2 ml); triethylamine was allowed to diffuse into the solution. Purple crystals were obtained in 30% yield after one week.

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX (Dolomanov et al., 2003) and X-SEED (Barbour, 2001); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top

Fig. 1. Anisotropic displacement ellipsoid plot (Barbour, 2001) of a portion of the layer structure of Co₂(DMF)₃(C₈H₃NO₆)₂^.DMF at the 50% probability level; hydrogen atoms are drawn as spheres of arbitrary radius. Symmetry codes are given in Table 1.

Poly[[tris(N,N-dimethylformamide)(µ₄-5-nitroisophthalato)(µ₃-5-nitroisophthalato)dicobalt(II)] N,N-dimethylformamide monosolvate] top

Crystal data top

[Co₂(C₃H₇NO)₃(C₈H₃NO₆)₂]·C₃H₇NO	F(000) = 1704
M_r = 828.47	D_x = 1.517 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 1014 reflections
a = 10.0833 (12) Å	θ = 2.3–26.7°
b = 17.0887 (19) Å	µ = 0.99 mm⁻¹
c = 21.074 (2) Å	T = 293 K
β = 92.910 (2)°	Block, purple
V = 3626.7 (7) Å³	0.40 × 0.30 × 0.30 mm
Z = 4

Data collection top

Bruker SMART diffractometer	7876 independent reflections
Radiation source: fine-focus sealed tube	5128 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.036
ω scans	θ_max = 27.0°, θ_min = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −12→11
T_min = 0.796, T_max = 1	k = −21→20
21143 measured reflections	l = −24→26

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) = 0.132	H-atom parameters constrained
S = 0.99	w = 1/[σ²(F_o²) + (0.0741P)² + 0.1674P] where P = (F_o² + 2F_c²)/3
7876 reflections	(Δ/σ)_max = 0.001
477 parameters	Δρ_max = 0.57 e Å⁻³
54 restraints	Δρ_min = −0.45 e Å⁻³

Crystal data top

[Co₂(C₃H₇NO)₃(C₈H₃NO₆)₂]·C₃H₇NO	V = 3626.7 (7) Å³
M_r = 828.47	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.0833 (12) Å	µ = 0.99 mm⁻¹
b = 17.0887 (19) Å	T = 293 K
c = 21.074 (2) Å	0.40 × 0.30 × 0.30 mm
β = 92.910 (2)°

Data collection top

Bruker SMART diffractometer	7876 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	5128 reflections with I > 2σ(I)
T_min = 0.796, T_max = 1	R_int = 0.036
21143 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.048	54 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 0.99	Δρ_max = 0.57 e Å⁻³
7876 reflections	Δρ_min = −0.45 e Å⁻³
477 parameters

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

	x	y	z	U_iso*/U_eq
Co1	0.54070 (4)	0.62850 (2)	0.36883 (2)	0.03535 (14)
Co2	0.75875 (4)	0.69413 (2)	0.25276 (2)	0.03577 (14)
O1	0.7161 (2)	0.61369 (15)	0.41609 (12)	0.0509 (6)
O2	0.8391 (2)	0.65261 (16)	0.33703 (12)	0.0536 (7)
O3	1.3188 (2)	0.63449 (18)	0.35333 (13)	0.0615 (8)
O4	1.4234 (2)	0.60440 (14)	0.44350 (11)	0.0452 (6)
O5	1.1571 (3)	0.5635 (2)	0.63158 (14)	0.0841 (10)
O6	0.9466 (3)	0.5792 (2)	0.62357 (14)	0.0890 (11)
O7	0.5916 (2)	0.62286 (13)	0.25975 (14)	0.0584 (7)
O8	0.5266 (3)	0.52567 (16)	0.31596 (14)	0.0641 (8)
O9	0.3476 (2)	0.28716 (13)	0.21118 (12)	0.0447 (6)
O10	0.4601 (3)	0.24599 (14)	0.12880 (13)	0.0548 (7)
O11	0.6418 (4)	0.4515 (2)	−0.00474 (17)	0.0982 (12)
O12	0.7008 (6)	0.5587 (3)	0.0369 (2)	0.160 (2)
O13	0.8704 (3)	0.60593 (15)	0.20713 (13)	0.0634 (8)
O14	0.9230 (3)	0.76957 (15)	0.25177 (13)	0.0619 (7)
O15	0.6900 (3)	0.72766 (15)	0.16294 (12)	0.0599 (7)
O16	1.0622 (10)	0.7746 (4)	0.5743 (4)	0.236 (4)
N1	1.0547 (3)	0.5774 (2)	0.60062 (15)	0.0565 (8)
N2	0.6509 (4)	0.4948 (3)	0.03991 (19)	0.0781 (11)
N3	1.0517 (3)	0.53017 (18)	0.20161 (17)	0.0715 (11)
N4	1.1460 (3)	0.7832 (2)	0.24308 (18)	0.0788 (11)
N5	0.6043 (3)	0.82156 (18)	0.09718 (13)	0.0572 (9)
N6	0.9621 (7)	0.8134 (3)	0.4885 (3)	0.1170 (18)
C1	0.8239 (3)	0.62893 (19)	0.39168 (17)	0.0385 (8)
C2	0.9490 (3)	0.61717 (18)	0.43297 (16)	0.0361 (7)
C3	1.0713 (3)	0.62258 (19)	0.40590 (16)	0.0390 (8)
H3	1.0752	0.6346	0.3630	0.047*
C4	1.1879 (3)	0.6102 (2)	0.44235 (16)	0.0381 (8)
C5	1.1835 (3)	0.5940 (2)	0.50582 (16)	0.0411 (8)
H5	1.2612	0.5851	0.5305	0.049*
C6	1.0611 (3)	0.5913 (2)	0.53248 (16)	0.0399 (8)
C7	0.9434 (3)	0.60096 (19)	0.49684 (16)	0.0394 (8)
H7	0.8621	0.5966	0.5155	0.047*
C8	1.3176 (3)	0.6162 (2)	0.41043 (18)	0.0411 (8)
C9	0.5582 (3)	0.5522 (2)	0.2641 (2)	0.0454 (9)
C10	0.5511 (3)	0.50093 (19)	0.20667 (17)	0.0400 (8)
C11	0.4916 (3)	0.42749 (18)	0.21119 (16)	0.0389 (8)
H11	0.4562	0.4127	0.2493	0.047*
C12	0.4843 (3)	0.37624 (18)	0.16031 (16)	0.0374 (7)
C13	0.5376 (3)	0.3984 (2)	0.10396 (17)	0.0458 (9)
H13	0.5358	0.3646	0.0694	0.055*
C14	0.5937 (4)	0.4717 (2)	0.10006 (18)	0.0525 (10)
C15	0.6007 (4)	0.5237 (2)	0.15018 (18)	0.0509 (9)
H15	0.6382	0.5730	0.1458	0.061*
C16	0.4250 (3)	0.29629 (19)	0.16771 (17)	0.0391 (8)
C17	0.9538 (4)	0.5620 (2)	0.2306 (2)	0.0616 (11)
H17	0.9474	0.5499	0.2734	0.074*
C18	1.0674 (8)	0.5465 (4)	0.1361 (3)	0.180 (4)
H18A	1.0040	0.5855	0.1219	0.269*
H18B	1.0532	0.4996	0.1117	0.269*
H18C	1.1556	0.5656	0.1306	0.269*
C19	1.1493 (5)	0.4793 (3)	0.2333 (3)	0.132 (3)
H19A	1.1219	0.4670	0.2751	0.198*
H19B	1.2337	0.5054	0.2365	0.198*
H19C	1.1569	0.4319	0.2092	0.198*
C20	1.0260 (4)	0.7575 (2)	0.2246 (2)	0.0653 (11)
H20	1.0193	0.7276	0.1877	0.078*
C21	1.1625 (6)	0.8289 (5)	0.2992 (3)	0.167 (4)
H21A	1.0866	0.8224	0.3244	0.250*
H21B	1.1710	0.8831	0.2880	0.250*
H21C	1.2409	0.8123	0.3232	0.250*
C22	1.2638 (5)	0.7666 (4)	0.2097 (3)	0.123 (2)
H22A	1.2399	0.7391	0.1711	0.184*
H22B	1.3228	0.7349	0.2360	0.184*
H22C	1.3071	0.8148	0.1999	0.184*
C23	0.6784 (3)	0.7969 (2)	0.14649 (15)	0.0503 (9)
H23	0.7252	0.8342	0.1707	0.060*
C24	0.5276 (6)	0.7661 (3)	0.0572 (2)	0.099 (2)
H24A	0.5459	0.7138	0.0716	0.149*
H24B	0.5520	0.7713	0.0139	0.149*
H24C	0.4346	0.7769	0.0597	0.149*
C25	0.5940 (4)	0.9038 (2)	0.08090 (19)	0.0641 (11)
H25A	0.6564	0.9332	0.1073	0.096*
H25B	0.5056	0.9218	0.0875	0.096*
H25C	0.6132	0.9108	0.0371	0.096*
C26	0.9403 (11)	0.7817 (4)	0.5443 (5)	0.175 (4)
H26	0.8589	0.7673	0.5596	0.210*
C27	1.0928 (11)	0.8320 (7)	0.4728 (6)	0.267 (6)
H27A	1.1542	0.8143	0.5061	0.400*
H27B	1.1009	0.8876	0.4680	0.400*
H27C	1.1123	0.8066	0.4337	0.400*
C28	0.8669 (10)	0.8325 (5)	0.4374 (4)	0.176 (4)
H28A	0.7826	0.8096	0.4456	0.265*
H28B	0.8972	0.8124	0.3981	0.265*
H28C	0.8577	0.8884	0.4344	0.265*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0234 (2)	0.0368 (2)	0.0459 (3)	−0.00044 (18)	0.00267 (17)	0.0023 (2)
Co2	0.0301 (2)	0.0324 (2)	0.0445 (3)	0.00062 (18)	−0.00140 (18)	0.00308 (19)
O1	0.0218 (12)	0.0657 (16)	0.0653 (17)	−0.0010 (11)	0.0021 (11)	0.0089 (13)
O2	0.0333 (14)	0.0776 (18)	0.0495 (16)	0.0072 (13)	−0.0015 (11)	0.0134 (14)
O3	0.0308 (14)	0.105 (2)	0.0496 (17)	−0.0015 (14)	0.0063 (11)	0.0135 (15)
O4	0.0236 (12)	0.0602 (15)	0.0515 (15)	0.0024 (11)	0.0001 (10)	0.0052 (12)
O5	0.073 (2)	0.128 (3)	0.0500 (18)	0.019 (2)	−0.0080 (15)	0.0166 (18)
O6	0.066 (2)	0.144 (3)	0.059 (2)	0.004 (2)	0.0244 (16)	0.0161 (19)
O7	0.0414 (15)	0.0348 (13)	0.098 (2)	−0.0069 (11)	−0.0058 (14)	−0.0051 (13)
O8	0.075 (2)	0.0554 (17)	0.0625 (19)	−0.0133 (15)	0.0114 (15)	−0.0148 (14)
O9	0.0435 (14)	0.0315 (12)	0.0598 (16)	−0.0068 (10)	0.0106 (12)	−0.0034 (11)
O10	0.0599 (17)	0.0379 (14)	0.0683 (18)	−0.0077 (12)	0.0183 (13)	−0.0083 (13)
O11	0.128 (3)	0.104 (3)	0.066 (2)	−0.006 (2)	0.035 (2)	0.008 (2)
O12	0.243 (6)	0.148 (4)	0.096 (3)	−0.123 (4)	0.055 (3)	0.006 (3)
O13	0.0591 (18)	0.0579 (16)	0.0722 (19)	0.0208 (14)	−0.0057 (14)	−0.0053 (14)
O14	0.0412 (15)	0.0610 (17)	0.085 (2)	−0.0156 (13)	0.0186 (14)	−0.0011 (15)
O15	0.080 (2)	0.0464 (15)	0.0516 (16)	0.0092 (14)	−0.0116 (14)	0.0047 (13)
O16	0.329 (8)	0.147 (5)	0.223 (6)	0.002 (6)	−0.068 (6)	−0.057 (5)
N1	0.054 (2)	0.070 (2)	0.046 (2)	0.0064 (17)	0.0045 (17)	0.0046 (16)
N2	0.087 (3)	0.089 (3)	0.059 (3)	−0.026 (2)	0.013 (2)	0.011 (2)
N3	0.072 (3)	0.068 (2)	0.077 (3)	0.031 (2)	0.028 (2)	0.009 (2)
N4	0.045 (2)	0.097 (3)	0.095 (3)	−0.014 (2)	0.008 (2)	0.003 (2)
N5	0.067 (2)	0.0534 (19)	0.0494 (19)	0.0082 (17)	−0.0100 (16)	0.0036 (15)
N6	0.134 (5)	0.098 (4)	0.120 (4)	−0.012 (3)	0.020 (4)	−0.034 (3)
C1	0.0256 (17)	0.0405 (18)	0.049 (2)	0.0047 (14)	0.0006 (14)	0.0002 (16)
C2	0.0226 (15)	0.0384 (17)	0.047 (2)	0.0009 (13)	0.0020 (13)	0.0032 (15)
C3	0.0296 (17)	0.0478 (19)	0.0393 (19)	−0.0016 (15)	0.0001 (14)	0.0044 (15)
C4	0.0255 (16)	0.0474 (19)	0.041 (2)	−0.0011 (14)	0.0003 (13)	0.0005 (15)
C5	0.0293 (17)	0.0479 (19)	0.046 (2)	0.0005 (15)	−0.0047 (14)	−0.0006 (16)
C6	0.0349 (18)	0.0449 (19)	0.0397 (19)	0.0038 (15)	0.0018 (14)	0.0041 (15)
C7	0.0262 (17)	0.0438 (18)	0.049 (2)	0.0032 (14)	0.0089 (14)	0.0034 (16)
C8	0.0228 (17)	0.049 (2)	0.052 (2)	−0.0035 (14)	0.0025 (15)	0.0001 (17)
C9	0.0286 (18)	0.038 (2)	0.069 (3)	−0.0006 (15)	−0.0030 (17)	−0.0078 (18)
C10	0.0320 (18)	0.0347 (17)	0.053 (2)	−0.0024 (14)	0.0014 (15)	0.0011 (16)
C11	0.0298 (17)	0.0367 (18)	0.050 (2)	−0.0007 (14)	0.0031 (14)	0.0028 (15)
C12	0.0287 (16)	0.0349 (17)	0.048 (2)	0.0004 (14)	−0.0018 (14)	−0.0023 (15)
C13	0.043 (2)	0.047 (2)	0.047 (2)	−0.0009 (17)	−0.0013 (16)	−0.0033 (17)
C14	0.050 (2)	0.057 (2)	0.051 (2)	−0.0101 (19)	0.0047 (18)	0.0104 (19)
C15	0.049 (2)	0.0386 (19)	0.065 (3)	−0.0122 (17)	−0.0025 (18)	0.0105 (18)
C16	0.0316 (18)	0.0357 (18)	0.049 (2)	−0.0005 (14)	−0.0046 (15)	−0.0023 (16)
C17	0.062 (3)	0.062 (3)	0.061 (3)	0.009 (2)	0.009 (2)	0.006 (2)
C18	0.281 (11)	0.150 (7)	0.117 (6)	0.123 (7)	0.099 (6)	0.046 (5)
C19	0.105 (5)	0.165 (6)	0.128 (5)	0.084 (5)	0.029 (4)	0.041 (5)
C20	0.051 (3)	0.071 (3)	0.073 (3)	−0.015 (2)	0.001 (2)	−0.007 (2)
C21	0.084 (5)	0.256 (10)	0.159 (7)	−0.058 (6)	−0.004 (4)	−0.110 (7)
C22	0.049 (3)	0.177 (7)	0.146 (6)	−0.008 (4)	0.026 (3)	−0.008 (5)
C23	0.054 (2)	0.054 (2)	0.043 (2)	0.0032 (19)	0.0003 (17)	0.0010 (18)
C24	0.136 (5)	0.072 (3)	0.085 (4)	0.001 (3)	−0.055 (3)	−0.002 (3)
C25	0.076 (3)	0.059 (3)	0.057 (3)	0.015 (2)	−0.005 (2)	0.009 (2)
C26	0.238 (9)	0.122 (6)	0.169 (7)	−0.015 (6)	0.044 (7)	−0.062 (6)
C27	0.241 (10)	0.278 (10)	0.282 (10)	−0.034 (8)	0.011 (8)	−0.061 (8)
C28	0.197 (8)	0.158 (6)	0.171 (7)	0.023 (6)	−0.014 (6)	−0.016 (6)

Geometric parameters (Å, º) top

Co1—O1	2.001 (2)	C2—C3	1.388 (4)
Co1—O3ⁱ	2.247 (2)	C3—C4	1.387 (4)
Co1—O4ⁱ	2.058 (2)	C3—H3	0.9300
Co1—O7	2.383 (3)	C4—C5	1.369 (5)
Co1—C8ⁱ	2.465 (3)	C4—C8	1.504 (4)
Co1—O8	2.082 (3)	C5—C6	1.383 (5)
Co1—O10ⁱⁱ	2.008 (2)	C5—H5	0.9300
Co2—O2	2.042 (2)	C6—C7	1.382 (4)
Co2—O7	2.091 (2)	C7—H7	0.9300
Co2—O9ⁱⁱ	2.082 (2)	C8—Co1ⁱⁱⁱ	2.465 (3)
Co2—O13	2.139 (3)	C9—C10	1.493 (5)
Co2—O14	2.100 (2)	C10—C15	1.371 (5)
Co2—O15	2.063 (2)	C10—C11	1.396 (4)
O1—C1	1.253 (4)	C11—C12	1.383 (5)
O2—C1	1.238 (4)	C11—H11	0.9300
O3—C8	1.244 (4)	C12—C13	1.381 (5)
O3—Co1ⁱⁱⁱ	2.247 (2)	C12—C16	1.503 (4)
O4—C8	1.260 (4)	C13—C14	1.379 (5)
O4—Co1ⁱⁱⁱ	2.058 (2)	C13—H13	0.9300
O5—N1	1.216 (4)	C14—C15	1.379 (5)
O6—N1	1.215 (4)	C15—H15	0.9300
O7—C9	1.259 (4)	C17—H17	0.9300
O8—C9	1.240 (4)	C18—H18A	0.9600
O9—C16	1.243 (4)	C18—H18B	0.9600
O9—Co2^iv	2.082 (2)	C18—H18C	0.9600
O10—C16	1.251 (4)	C19—H19A	0.9600
O10—Co1^iv	2.008 (2)	C19—H19B	0.9600
O11—N2	1.196 (5)	C19—H19C	0.9600
O12—N2	1.206 (5)	C20—H20	0.9300
O13—C17	1.214 (4)	C21—H21A	0.9600
O14—C20	1.229 (4)	C21—H21B	0.9600
O15—C23	1.237 (4)	C21—H21C	0.9600
O16—C26	1.359 (8)	C22—H22A	0.9600
N1—C6	1.460 (5)	C22—H22B	0.9600
N2—C14	1.473 (5)	C22—H22C	0.9600
N3—C17	1.305 (5)	C23—H23	0.9300
N3—C18	1.426 (6)	C24—H24A	0.9600
N3—C19	1.450 (5)	C24—H24B	0.9600
N4—C20	1.326 (5)	C24—H24C	0.9600
N4—C21	1.421 (6)	C25—H25A	0.9600
N4—C22	1.439 (5)	C25—H25B	0.9600
N5—C23	1.318 (4)	C25—H25C	0.9600
N5—C25	1.449 (4)	C26—H26	0.9300
N5—C24	1.463 (5)	C27—H27A	0.9600
N6—C26	1.322 (8)	C27—H27B	0.9600
N6—C27	1.411 (8)	C27—H27C	0.9600
N6—C28	1.444 (7)	C28—H28A	0.9600
C1—C2	1.509 (4)	C28—H28B	0.9600
C2—C7	1.378 (5)	C28—H28C	0.9600

O1—Co1—O10ⁱⁱ	96.82 (11)	O3—C8—C4	120.1 (3)
O1—Co1—O4ⁱ	97.00 (10)	O4—C8—C4	118.2 (3)
O10ⁱⁱ—Co1—O4ⁱ	100.24 (10)	O3—C8—Co1ⁱⁱⁱ	65.20 (18)
O1—Co1—O8	101.20 (11)	O4—C8—Co1ⁱⁱⁱ	56.52 (16)
O10ⁱⁱ—Co1—O8	148.98 (12)	C4—C8—Co1ⁱⁱⁱ	174.2 (3)
O4ⁱ—Co1—O8	102.36 (11)	O8—C9—O7	119.8 (4)
O1—Co1—O3ⁱ	157.87 (10)	O8—C9—C10	119.8 (3)
O10ⁱⁱ—Co1—O3ⁱ	87.29 (11)	O7—C9—C10	120.4 (4)
O4ⁱ—Co1—O3ⁱ	60.88 (9)	C15—C10—C11	119.5 (3)
O8—Co1—O3ⁱ	85.42 (12)	C15—C10—C9	122.2 (3)
O1—Co1—O7	104.29 (10)	C11—C10—C9	118.4 (3)
O10ⁱⁱ—Co1—O7	93.78 (9)	C12—C11—C10	121.5 (3)
O4ⁱ—Co1—O7	152.88 (9)	C12—C11—H11	119.3
O8—Co1—O7	57.43 (10)	C10—C11—H11	119.3
O3ⁱ—Co1—O7	97.09 (9)	C13—C12—C11	119.0 (3)
O1—Co1—C8ⁱ	127.71 (11)	C13—C12—C16	120.9 (3)
O10ⁱⁱ—Co1—C8ⁱ	94.08 (11)	C11—C12—C16	120.1 (3)
O4ⁱ—Co1—C8ⁱ	30.72 (10)	C14—C13—C12	118.6 (3)
O8—Co1—C8ⁱ	94.58 (11)	C14—C13—H13	120.7
O3ⁱ—Co1—C8ⁱ	30.16 (10)	C12—C13—H13	120.7
O7—Co1—C8ⁱ	125.81 (10)	C13—C14—C15	123.0 (3)
O2—Co2—O15	173.94 (11)	C13—C14—N2	118.3 (4)
O2—Co2—O9ⁱⁱ	97.87 (10)	C15—C14—N2	118.7 (4)
O15—Co2—O9ⁱⁱ	88.15 (10)	C10—C15—C14	118.3 (3)
O2—Co2—O7	91.26 (11)	C10—C15—H15	120.8
O15—Co2—O7	89.54 (11)	C14—C15—H15	120.8
O9ⁱⁱ—Co2—O7	89.27 (10)	O9—C16—O10	127.3 (3)
O2—Co2—O14	86.77 (11)	O9—C16—C12	117.3 (3)
O15—Co2—O14	92.79 (11)	O10—C16—C12	115.4 (3)
O9ⁱⁱ—Co2—O14	87.47 (10)	O13—C17—N3	126.3 (4)
O7—Co2—O14	175.92 (11)	O13—C17—H17	116.9
O2—Co2—O13	87.22 (11)	N3—C17—H17	116.9
O15—Co2—O13	86.74 (10)	N3—C18—H18A	109.5
O9ⁱⁱ—Co2—O13	174.03 (10)	N3—C18—H18B	109.5
O7—Co2—O13	93.76 (11)	H18A—C18—H18B	109.5
O14—Co2—O13	89.71 (11)	N3—C18—H18C	109.5
C1—O1—Co1	122.2 (2)	H18A—C18—H18C	109.5
C1—O2—Co2	149.4 (2)	H18B—C18—H18C	109.5
C8—O3—Co1ⁱⁱⁱ	84.64 (19)	N3—C19—H19A	109.5
C8—O4—Co1ⁱⁱⁱ	92.8 (2)	N3—C19—H19B	109.5
C9—O7—Co2	141.6 (2)	H19A—C19—H19B	109.5
C9—O7—Co1	84.1 (2)	N3—C19—H19C	109.5
Co2—O7—Co1	104.97 (11)	H19A—C19—H19C	109.5
C9—O8—Co1	98.6 (2)	H19B—C19—H19C	109.5
C16—O9—Co2^iv	136.0 (2)	O14—C20—N4	126.0 (4)
C16—O10—Co1^iv	132.0 (2)	O14—C20—H20	117.0
C17—O13—Co2	128.5 (3)	N4—C20—H20	117.0
C20—O14—Co2	126.0 (3)	N4—C21—H21A	109.5
C23—O15—Co2	123.1 (2)	N4—C21—H21B	109.5
O6—N1—O5	123.1 (4)	H21A—C21—H21B	109.5
O6—N1—C6	118.2 (3)	N4—C21—H21C	109.5
O5—N1—C6	118.7 (3)	H21A—C21—H21C	109.5
O11—N2—O12	122.3 (4)	H21B—C21—H21C	109.5
O11—N2—C14	119.6 (4)	N4—C22—H22A	109.5
O12—N2—C14	118.1 (4)	N4—C22—H22B	109.5
C17—N3—C18	119.7 (4)	H22A—C22—H22B	109.5
C17—N3—C19	123.1 (4)	N4—C22—H22C	109.5
C18—N3—C19	117.2 (4)	H22A—C22—H22C	109.5
C20—N4—C21	119.5 (4)	H22B—C22—H22C	109.5
C20—N4—C22	123.7 (4)	O15—C23—N5	124.7 (4)
C21—N4—C22	116.8 (5)	O15—C23—H23	117.6
C23—N5—C25	121.9 (3)	N5—C23—H23	117.6
C23—N5—C24	120.6 (3)	N5—C24—H24A	109.5
C25—N5—C24	117.5 (3)	N5—C24—H24B	109.5
C26—N6—C27	120.0 (9)	H24A—C24—H24B	109.5
C26—N6—C28	128.5 (9)	N5—C24—H24C	109.5
C27—N6—C28	111.6 (9)	H24A—C24—H24C	109.5
O2—C1—O1	126.9 (3)	H24B—C24—H24C	109.5
O2—C1—C2	116.1 (3)	N5—C25—H25A	109.5
O1—C1—C2	116.9 (3)	N5—C25—H25B	109.5
C7—C2—C3	119.8 (3)	H25A—C25—H25B	109.5
C7—C2—C1	121.0 (3)	N5—C25—H25C	109.5
C3—C2—C1	119.2 (3)	H25A—C25—H25C	109.5
C4—C3—C2	120.5 (3)	H25B—C25—H25C	109.5
C4—C3—H3	119.7	N6—C26—O16	105.3 (9)
C2—C3—H3	119.7	N6—C26—H26	127.4
C5—C4—C3	120.2 (3)	O16—C26—H26	127.4
C5—C4—C8	121.5 (3)	N6—C27—H27A	109.5
C3—C4—C8	118.3 (3)	N6—C27—H27B	109.5
C4—C5—C6	118.5 (3)	H27A—C27—H27B	109.5
C4—C5—H5	120.7	N6—C27—H27C	109.5
C6—C5—H5	120.7	H27A—C27—H27C	109.5
C7—C6—C5	122.4 (3)	H27B—C27—H27C	109.5
C7—C6—N1	118.3 (3)	N6—C28—H28A	109.5
C5—C6—N1	119.3 (3)	N6—C28—H28B	109.5
C2—C7—C6	118.5 (3)	H28A—C28—H28B	109.5
C2—C7—H7	120.7	N6—C28—H28C	109.5
C6—C7—H7	120.7	H28A—C28—H28C	109.5
O3—C8—O4	121.7 (3)	H28B—C28—H28C	109.5

O10ⁱⁱ—Co1—O1—C1	−72.3 (3)	C4—C5—C6—C7	2.9 (5)
O4ⁱ—Co1—O1—C1	−173.5 (3)	C4—C5—C6—N1	−177.5 (3)
O8—Co1—O1—C1	82.4 (3)	O6—N1—C6—C7	−4.0 (5)
O3ⁱ—Co1—O1—C1	−171.9 (3)	O5—N1—C6—C7	175.0 (4)
O7—Co1—O1—C1	23.4 (3)	O6—N1—C6—C5	176.3 (4)
C8ⁱ—Co1—O1—C1	−172.8 (2)	O5—N1—C6—C5	−4.7 (5)
O9ⁱⁱ—Co2—O2—C1	53.7 (5)	C3—C2—C7—C6	0.7 (5)
O7—Co2—O2—C1	−35.7 (5)	C1—C2—C7—C6	−179.5 (3)
O14—Co2—O2—C1	140.7 (5)	C5—C6—C7—C2	−2.8 (5)
O13—Co2—O2—C1	−129.4 (5)	N1—C6—C7—C2	177.5 (3)
O2—Co2—O7—C9	−59.1 (5)	Co1ⁱⁱⁱ—O3—C8—O4	−0.7 (3)
O15—Co2—O7—C9	114.8 (5)	Co1ⁱⁱⁱ—O3—C8—C4	177.4 (3)
O9ⁱⁱ—Co2—O7—C9	−157.0 (5)	Co1ⁱⁱⁱ—O4—C8—O3	0.7 (4)
O13—Co2—O7—C9	28.1 (5)	Co1ⁱⁱⁱ—O4—C8—C4	−177.4 (3)
O2—Co2—O7—Co1	40.41 (11)	C5—C4—C8—O3	−176.8 (3)
O15—Co2—O7—Co1	−145.60 (11)	C3—C4—C8—O3	2.4 (5)
O9ⁱⁱ—Co2—O7—Co1	−57.44 (10)	C5—C4—C8—O4	1.4 (5)
O13—Co2—O7—Co1	127.70 (10)	C3—C4—C8—O4	−179.5 (3)
O1—Co1—O7—C9	96.0 (2)	Co1—O8—C9—O7	3.2 (4)
O10ⁱⁱ—Co1—O7—C9	−166.0 (2)	Co1—O8—C9—C10	−174.3 (3)
O4ⁱ—Co1—O7—C9	−44.6 (3)	Co2—O7—C9—O8	103.9 (5)
O8—Co1—O7—C9	1.7 (2)	Co1—O7—C9—O8	−2.8 (3)
O3ⁱ—Co1—O7—C9	−78.2 (2)	Co2—O7—C9—C10	−78.5 (5)
C8ⁱ—Co1—O7—C9	−68.2 (2)	Co1—O7—C9—C10	174.8 (3)
O1—Co1—O7—Co2	−46.01 (12)	O8—C9—C10—C15	−171.4 (3)
O10ⁱⁱ—Co1—O7—Co2	52.01 (12)	O7—C9—C10—C15	11.1 (5)
O4ⁱ—Co1—O7—Co2	173.32 (15)	O8—C9—C10—C11	8.6 (5)
O8—Co1—O7—Co2	−140.32 (15)	O7—C9—C10—C11	−168.9 (3)
O3ⁱ—Co1—O7—Co2	139.75 (11)	C15—C10—C11—C12	1.5 (5)
C8ⁱ—Co1—O7—Co2	149.80 (11)	C9—C10—C11—C12	−178.5 (3)
O1—Co1—O8—C9	−101.7 (2)	C10—C11—C12—C13	0.3 (5)
O10ⁱⁱ—Co1—O8—C9	22.7 (4)	C10—C11—C12—C16	177.3 (3)
O4ⁱ—Co1—O8—C9	158.5 (2)	C11—C12—C13—C14	−1.5 (5)
O3ⁱ—Co1—O8—C9	99.7 (2)	C16—C12—C13—C14	−178.5 (3)
O7—Co1—O8—C9	−1.7 (2)	C12—C13—C14—C15	0.9 (6)
C8ⁱ—Co1—O8—C9	128.4 (2)	C12—C13—C14—N2	179.7 (3)
O2—Co2—O13—C17	−7.4 (3)	O11—N2—C14—C13	3.7 (7)
O15—Co2—O13—C17	172.2 (3)	O12—N2—C14—C13	−179.4 (5)
O7—Co2—O13—C17	−98.5 (3)	O11—N2—C14—C15	−177.5 (4)
O14—Co2—O13—C17	79.4 (3)	O12—N2—C14—C15	−0.6 (7)
O2—Co2—O14—C20	95.1 (3)	C11—C10—C15—C14	−2.0 (5)
O15—Co2—O14—C20	−78.8 (3)	C9—C10—C15—C14	178.0 (3)
O9ⁱⁱ—Co2—O14—C20	−166.9 (3)	C13—C14—C15—C10	0.8 (6)
O13—Co2—O14—C20	7.9 (3)	N2—C14—C15—C10	−177.9 (4)
O9ⁱⁱ—Co2—O15—C23	38.7 (2)	Co2^iv—O9—C16—O10	2.3 (6)
O7—Co2—O15—C23	128.0 (2)	Co2^iv—O9—C16—C12	−177.6 (2)
O14—Co2—O15—C23	−48.7 (2)	C13—C12—C16—O9	−160.5 (3)
O13—Co2—O15—C23	−138.2 (2)	C11—C12—C16—O9	22.5 (5)
Co2—O2—C1—O1	8.8 (8)	C13—C12—C16—O10	19.6 (5)
Co2—O2—C1—C2	−171.4 (4)	C11—C12—C16—O10	−157.4 (3)
Co1—O1—C1—O2	−1.7 (5)	Co2—O13—C17—N3	−153.3 (3)
Co1—O1—C1—C2	178.5 (2)	C18—N3—C17—O13	0.2 (4)
O2—C1—C2—C7	171.4 (3)	C19—N3—C17—O13	178.7 (3)
O1—C1—C2—C7	−8.7 (5)	Co2—O14—C20—N4	−149.3 (3)
O2—C1—C2—C3	−8.8 (5)	C21—N4—C20—O14	0.2 (3)
O1—C1—C2—C3	171.1 (3)	C22—N4—C20—O14	179.4 (3)
C7—C2—C3—C4	1.3 (5)	Co2—O15—C23—N5	−161.2 (2)
C1—C2—C3—C4	−178.5 (3)	C25—N5—C23—O15	179.4 (3)
C2—C3—C4—C5	−1.3 (5)	C24—N5—C23—O15	0.2 (3)
C2—C3—C4—C8	179.6 (3)	C27—N6—C26—O16	−0.3 (3)
C3—C4—C5—C6	−0.7 (5)	C28—N6—C26—O16	179.0 (3)
C8—C4—C5—C6	178.4 (3)

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

Experimental details

Crystal data
Chemical formula	[Co₂(C₃H₇NO)₃(C₈H₃NO₆)₂]·C₃H₇NO
M_r	828.47
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.0833 (12), 17.0887 (19), 21.074 (2)
β (°)	92.910 (2)
V (Å³)	3626.7 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.99
Crystal size (mm)	0.40 × 0.30 × 0.30

Data collection
Diffractometer	Bruker SMART diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.796, 1
No. of measured, independent and observed [I > 2σ(I)] reflections	21143, 7876, 5128
R_int	0.036
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.048, 0.132, 0.99
No. of reflections	7876
No. of parameters	477
No. of restraints	54
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.57, −0.45

Computer programs: SMART (Bruker, 1999), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX (Dolomanov et al., 2003) and X-SEED (Barbour, 2001), publCIF (Westrip, 2010).

Selected bond lengths (Å) top

Co1—O1	2.001 (2)	Co2—O2	2.042 (2)
Co1—O3ⁱ	2.247 (2)	Co2—O7	2.091 (2)
Co1—O4ⁱ	2.058 (2)	Co2—O9ⁱⁱ	2.082 (2)
Co1—O7	2.383 (3)	Co2—O13	2.139 (3)
Co1—C8ⁱ	2.465 (3)	Co2—O14	2.100 (2)
Co1—O8	2.082 (3)	Co2—O15	2.063 (2)
Co1—O10ⁱⁱ	2.008 (2)

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

Acknowledgements

We thank the National Science Foundation of China (No. J0830412) and the University of Malaya for supporting this study.

References

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