Chloridobis(dimethyl­glyoximato-κ2N,N′)(ethyl pyridine-3-carboxyl­ate-κN)cobalt(III)

Wang, N.; Sun, X.; Wan, D.; Chen, J.; Li, B.

doi:10.1107/S1600536811051397

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 1| January 2012| Page m20

doi:10.1107/S1600536811051397

Open

access

Chloridobis(dimethylglyoximato-κ²N,N′)(ethyl pyridine-3-carboxylate-κN)cobalt(III)

Ning Wang,^a ^* Xuzhuo Sun,^a Dongjin Wan,^a Jing Chen ^a and Bo Li ^a

^aHenan University of Technology, School of Chemistry and Chemical Engineering, Zhengzhou 450001, People's Republic of China
^*Correspondence e-mail: ssdyok@yahoo.com.cn

(Received 7 November 2011; accepted 29 November 2011; online 7 December 2011)

In the title compound, [Co(C₄H₇N₂O₂)₂Cl(C₈H₉NO₂)], which was prepared as a model complex of vitamin B₁₂, the Co^III atom, which is linked to four N atoms of the pseudo-macrocyclic (dmgH)₂ ligand (dmgH is dimethylglyoximate) in the equatorial plane and one Cl⁻ anion and one N atom of ethyl nicotinate in apical positions, displays an approximately octahedral coordination. The Co atom is 0.0187 (8) Å out of the mean plane of the four equatorial N atoms. The structure has an O⋯H⋯O bridge, which is very common in cobaloxime derivatives, with O⋯H distances of 1.24 (2) and 1.25 (2) Å.

Related literature

For background to the chemistry of cobaloximes, see: Schrayzer (1968 ); Zangrando et al. (2003 ). For applications of cobaloximes in proton reduction, see: Razavet et al. (2005 ). For related structures, see: Mandal & Gupta (2005 , 2007 ); Bhuyan et al. (2007 ); Dutta et al. (2009 ). For NMR research on O⋯H⋯O bridges, see: Bakac & Espenson (1984 ). For deprotonation of O⋯H⋯O bridges by BF₃·Et₂O, see: Magnuson & Weber (1974 ).

Experimental

Crystal data

[Co(C₄H₇N₂O₂)₂Cl(C₈H₉NO₂)]
M_r = 475.77
Monoclinic, P 2₁ /c
a = 8.1961 (11) Å
b = 14.2224 (19) Å
c = 17.365 (2) Å
β = 98.340 (2)°
V = 2002.8 (5) Å³
Z = 4
Mo Kα radiation
μ = 1.03 mm⁻¹
T = 293 K
0.32 × 0.15 × 0.06 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2001 ) T_min = 0.830, T_max = 0.940
9364 measured reflections
3532 independent reflections
3104 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.028
wR(F²) = 0.076
S = 1.10
3532 reflections
272 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.27 e Å⁻³
Δρ_min = −0.28 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—Cl1	2.2326 (6)
Co1—N1	1.8925 (16)
Co1—N2	1.8872 (16)
Co1—N3	1.8970 (16)
Co1—N4	1.9020 (16)
Co1—N5	1.9701 (15)

Data collection: APEX2 (Bruker, 2007 ); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811051397/vn2023sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811051397/vn2023Isup2.hkl

checkCIF report

Comment top

Cobaloximes have been extensively used to mimic the vitamin B₁₂ coenzyme (Schrayzer, 1968). Recently they have been also used to catalyze the proton reduction as a function model of hydrogenase (Razavet et al., 2005). The cobalt atom in the title compound, [Co(dmgH)₂(3-(COOEt)C₅H₄N)Cl], is in a distorted octahedral geometry by four nitrogen atoms of the pseudomacrocyclic (dmgH)₂ ligand in the equatorial plane and by one chlorine atom and a nitrogen atom of ethyl nicotinate, respectively, in mutually trans positions (N5—Co—Cl1 = 179.88° (5)). The mean Co—N bond length is 1.8944 Å (16). The mean O—O distance is 2.513 Å (3). The Co atom is 0.0187 Å (8) out of the mean plane of the four nitrogen atoms. The plane of the four nitrogen atoms is practically planar. The O2···H2···O4 bridge in the structure is very common in cobaloxime derivatives (Mandal & Gupta, 2005, 2007; Bhuyan et al., 2007; Dutta et al., 2009). The presence of the O···H···O bridging moieties in cobaloxime derivatives ensures co-planarity of the two molecules of ligand and promotes the stability of the cobaloxime molecule (Zangrando et al., 2003). The existence of O···H···O bridging is supported by NMR data and further substantiated by their chemical behavior with BF₃.Et₂O in readily forming an O—BF₂—O system by deprotonation of an O···H···O bridge (Magnuson & Weber, 1974; Bakac & Espenson, 1984). The other O···H···O (O1···H1···O3) group is less bridging than the O2···H2···O4 group since H1 is substantially close to O3 than to O1 (O3—H1 = 1.03 (3) Å)

Related literature top

For background to the chemistry of cobaloximes, see: Schrayzer (1968); Zangrando et al. (2003). For applications of cobaloximes in proton reduction, see: Razavet et al. (2005). For related structures, see: Mandal & Gupta (2005, 2007); Bhuyan et al. (2007); Dutta et al. (2009). For NMR research on O···H···O bridges, see: Bakac & Espenson (1984). For deprotonation of O···H···O bridges by BF₃.Et₂O, see: Magnuson & Weber (1974).

Experimental top

Co(dmgH)(dmgH₂)Cl, (3.6 g, 0.01 mol) and ethyl nicotinate (3.0 g, 0.02 mol) were added to chloroform (90 ml). The suspension was stirred for 20 minutes. Water (30 ml) was then added to the flask and the mixture was vigorously stirred for 2 h. The aqueous layer was discarded and the chloroform layer filtered and extracted with water until the washings were nearly colorless. The solution was reduced in volume and the product precipitated by addition of ethanol (95%); yield 69%. Brown single crystals of [Co(dmgH)₂(3-(COOEt)C₅H₄N)Cl] were recrystallized from the solution CHCl₃/acetone (v:v = 1:1). ¹H NMR(400 MHz, CDCl₃): δ 8.85 (s, 1 H, Ha), 8.44 (d, 5.6 Hz, 1 H, Hb), 8.30 (d, 8 Hz, 1 H, Hc), 7.26 (dd, 6 Hz, 8.4 Hz, 1 H, Hd), 4.42 (q, 7.2 Hz, 2 H, CH₂), 2.40 (s, 12 H, N=CCH₃), 1.42 (t, 7.2 Hz, 3 H, CH₃).

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT-Plus (Bruker, 2007); data reduction: SAINT-Plus (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level.

Chloridobis(dimethylglyoximato-κ²N,N')(ethyl pyridine-3-carboxylate-κN)cobalt(III) top

Crystal data top

[Co(C₄H₇N₂O₂)₂Cl(C₈H₉NO₂)]	F(000) = 984
M_r = 475.77	D_x = 1.578 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 4611 reflections
a = 8.1961 (11) Å	θ = 2.4–27.8°
b = 14.2224 (19) Å	µ = 1.03 mm⁻¹
c = 17.365 (2) Å	T = 293 K
β = 98.340 (2)°	Needle, brown
V = 2002.8 (5) Å³	0.32 × 0.15 × 0.06 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	3532 independent reflections
Radiation source: fine-focus sealed tube	3104 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
phi and ω scans	θ_max = 25.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2001)	h = −9→9
T_min = 0.830, T_max = 0.940	k = −16→12
9364 measured reflections	l = −20→20

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) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ²(F_o²) + (0.0374P)² + 0.6155P] where P = (F_o² + 2F_c²)/3
3532 reflections	(Δ/σ)_max = 0.005
272 parameters	Δρ_max = 0.27 e Å⁻³
0 restraints	Δρ_min = −0.28 e Å⁻³

Crystal data top

[Co(C₄H₇N₂O₂)₂Cl(C₈H₉NO₂)]	V = 2002.8 (5) Å³
M_r = 475.77	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.1961 (11) Å	µ = 1.03 mm⁻¹
b = 14.2224 (19) Å	T = 293 K
c = 17.365 (2) Å	0.32 × 0.15 × 0.06 mm
β = 98.340 (2)°

Data collection top

Bruker APEXII area-detector diffractometer	3532 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2001)	3104 reflections with I > 2σ(I)
T_min = 0.830, T_max = 0.940	R_int = 0.020
9364 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.076	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	Δρ_max = 0.27 e Å⁻³
3532 reflections	Δρ_min = −0.28 e Å⁻³
272 parameters

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.35812 (3)	0.472077 (17)	0.212009 (14)	0.02362 (10)
Cl1	0.21204 (7)	0.50607 (5)	0.09665 (3)	0.04574 (16)
N3	0.2327 (2)	0.56109 (11)	0.25989 (9)	0.0296 (4)
N1	0.5278 (2)	0.55203 (11)	0.18744 (9)	0.0291 (4)
N4	0.1851 (2)	0.39228 (11)	0.23476 (9)	0.0288 (4)
O1	0.53203 (19)	0.64264 (10)	0.20602 (9)	0.0436 (4)
N5	0.48695 (18)	0.44181 (11)	0.31377 (9)	0.0240 (3)
C1	0.6351 (2)	0.51383 (15)	0.14900 (11)	0.0316 (5)
N2	0.4780 (2)	0.38275 (11)	0.16259 (9)	0.0296 (4)
O3	0.2744 (2)	0.65352 (10)	0.26840 (10)	0.0438 (4)
H1	0.381 (3)	0.6557 (17)	0.2433 (14)	0.053*
O4	0.17824 (19)	0.30074 (10)	0.21648 (9)	0.0418 (4)
O2	0.4320 (2)	0.29203 (10)	0.15452 (9)	0.0431 (4)
H2	0.298 (3)	0.2881 (17)	0.1809 (14)	0.052*
C7	0.0736 (2)	0.43004 (15)	0.27068 (11)	0.0300 (4)
C5	0.1010 (2)	0.53125 (14)	0.28465 (11)	0.0302 (5)
C3	0.6056 (2)	0.41350 (15)	0.13459 (11)	0.0332 (5)
C10	0.6455 (2)	0.48779 (14)	0.43410 (11)	0.0298 (4)
C13	0.5055 (2)	0.35154 (13)	0.33651 (12)	0.0304 (4)
H13A	0.4576	0.3047	0.3032	0.036*
C2	0.7698 (3)	0.56681 (18)	0.11945 (14)	0.0479 (6)
H2A	0.7457	0.5722	0.0639	0.072*
H2B	0.8722	0.5340	0.1332	0.072*
H2C	0.7783	0.6284	0.1422	0.072*
C9	0.5572 (2)	0.50894 (13)	0.36194 (11)	0.0264 (4)
H9A	0.5463	0.5715	0.3464	0.032*
O6	0.6991 (2)	0.64724 (10)	0.45873 (8)	0.0423 (4)
O5	0.7992 (3)	0.54489 (13)	0.55052 (10)	0.0663 (6)
C11	0.6623 (3)	0.39457 (15)	0.45707 (12)	0.0365 (5)
H11A	0.7198	0.3789	0.5055	0.044*
C14	0.7245 (3)	0.56221 (16)	0.48794 (12)	0.0360 (5)
C12	0.5929 (3)	0.32574 (15)	0.40745 (12)	0.0366 (5)
H12A	0.6045	0.2627	0.4213	0.044*
C6	−0.0121 (3)	0.59176 (18)	0.32237 (14)	0.0481 (6)
H6A	−0.0050	0.5750	0.3763	0.072*
H6B	−0.1231	0.5830	0.2970	0.072*
H6C	0.0189	0.6565	0.3181	0.072*
C8	−0.0657 (3)	0.37698 (18)	0.29583 (14)	0.0450 (6)
H8A	−0.0690	0.3147	0.2743	0.068*
H8B	−0.1674	0.4088	0.2778	0.068*
H8C	−0.0506	0.3732	0.3516	0.068*
C15	0.7661 (3)	0.72628 (16)	0.50703 (13)	0.0447 (6)
H15A	0.7672	0.7105	0.5615	0.054*
H15B	0.6954	0.7807	0.4954	0.054*
C4	0.7100 (3)	0.35388 (19)	0.09048 (15)	0.0545 (7)
H4A	0.6836	0.2888	0.0968	0.082*
H4B	0.8242	0.3643	0.1100	0.082*
H4C	0.6893	0.3702	0.0363	0.082*
C16	0.9359 (3)	0.74998 (19)	0.49341 (15)	0.0545 (7)
H16A	0.9764	0.8019	0.5260	0.082*
H16B	0.9347	0.7668	0.4398	0.082*
H16C	1.0064	0.6965	0.5057	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02584 (16)	0.02073 (15)	0.02457 (15)	0.00085 (10)	0.00463 (11)	−0.00105 (10)
Cl1	0.0416 (3)	0.0654 (4)	0.0287 (3)	0.0097 (3)	−0.0002 (2)	0.0059 (3)
N3	0.0331 (9)	0.0236 (9)	0.0318 (9)	0.0045 (7)	0.0038 (7)	0.0002 (7)
N1	0.0338 (9)	0.0213 (8)	0.0328 (9)	0.0000 (7)	0.0068 (7)	0.0037 (7)
N4	0.0295 (9)	0.0256 (9)	0.0302 (9)	−0.0030 (7)	0.0007 (7)	−0.0022 (7)
O1	0.0527 (10)	0.0208 (8)	0.0608 (10)	−0.0049 (7)	0.0199 (8)	0.0019 (7)
N5	0.0252 (8)	0.0215 (8)	0.0260 (8)	0.0002 (6)	0.0064 (6)	−0.0001 (6)
C1	0.0310 (11)	0.0358 (12)	0.0284 (10)	0.0015 (9)	0.0057 (9)	0.0075 (9)
N2	0.0364 (10)	0.0243 (9)	0.0286 (8)	0.0022 (7)	0.0059 (7)	−0.0035 (7)
O3	0.0500 (10)	0.0216 (7)	0.0626 (10)	0.0031 (7)	0.0173 (8)	−0.0051 (7)
O4	0.0425 (9)	0.0280 (8)	0.0559 (10)	−0.0114 (7)	0.0100 (8)	−0.0108 (7)
O2	0.0538 (10)	0.0254 (8)	0.0521 (9)	−0.0034 (7)	0.0148 (8)	−0.0141 (7)
C7	0.0255 (10)	0.0378 (12)	0.0261 (10)	−0.0003 (9)	0.0016 (8)	0.0005 (8)
C5	0.0286 (10)	0.0358 (12)	0.0260 (10)	0.0082 (8)	0.0035 (8)	0.0020 (8)
C3	0.0347 (11)	0.0372 (12)	0.0289 (10)	0.0070 (9)	0.0088 (9)	0.0004 (9)
C10	0.0282 (10)	0.0330 (11)	0.0285 (10)	0.0002 (8)	0.0047 (8)	−0.0006 (8)
C13	0.0333 (11)	0.0223 (10)	0.0359 (11)	0.0002 (8)	0.0063 (9)	0.0005 (8)
C2	0.0439 (13)	0.0537 (15)	0.0499 (14)	−0.0018 (11)	0.0197 (11)	0.0134 (12)
C9	0.0271 (10)	0.0242 (10)	0.0284 (10)	0.0008 (8)	0.0058 (8)	0.0005 (8)
O6	0.0549 (10)	0.0320 (8)	0.0364 (8)	−0.0040 (7)	−0.0056 (7)	−0.0065 (7)
O5	0.0923 (15)	0.0546 (11)	0.0409 (10)	−0.0077 (10)	−0.0283 (10)	0.0029 (8)
C11	0.0361 (12)	0.0410 (13)	0.0313 (11)	0.0038 (9)	0.0012 (9)	0.0082 (9)
C14	0.0354 (12)	0.0421 (13)	0.0294 (11)	−0.0024 (10)	0.0014 (9)	−0.0033 (9)
C12	0.0402 (12)	0.0271 (11)	0.0420 (12)	0.0036 (9)	0.0043 (10)	0.0091 (9)
C6	0.0463 (14)	0.0515 (15)	0.0493 (14)	0.0159 (11)	0.0158 (11)	−0.0007 (11)
C8	0.0324 (12)	0.0562 (15)	0.0472 (13)	−0.0083 (11)	0.0084 (10)	0.0013 (11)
C15	0.0485 (14)	0.0396 (13)	0.0434 (13)	−0.0036 (11)	−0.0016 (11)	−0.0170 (10)
C4	0.0595 (16)	0.0564 (16)	0.0530 (15)	0.0150 (13)	0.0271 (13)	−0.0061 (12)
C16	0.0541 (15)	0.0545 (16)	0.0559 (15)	−0.0110 (12)	0.0109 (12)	−0.0137 (13)

Geometric parameters (Å, º) top

Co1—Cl1	2.2326 (6)	C13—C12	1.382 (3)
Co1—N1	1.8925 (16)	C13—H13A	0.9300
Co1—N2	1.8872 (16)	C2—H2A	0.9600
Co1—N3	1.8970 (16)	C2—H2B	0.9600
Co1—N4	1.9020 (16)	C2—H2C	0.9600
Co1—N5	1.9701 (15)	C9—H9A	0.9300
N3—C5	1.291 (3)	O6—C14	1.316 (3)
N3—O3	1.361 (2)	O6—C15	1.461 (2)
N1—C1	1.298 (3)	O5—C14	1.193 (3)
N1—O1	1.328 (2)	C11—C12	1.372 (3)
N4—C7	1.296 (3)	C11—H11A	0.9300
N4—O4	1.339 (2)	C12—H12A	0.9300
N5—C9	1.343 (2)	C6—H6A	0.9600
N5—C13	1.345 (2)	C6—H6B	0.9600
C1—C3	1.463 (3)	C6—H6C	0.9600
C1—C2	1.488 (3)	C8—H8A	0.9600
N2—C3	1.292 (3)	C8—H8B	0.9600
N2—O2	1.346 (2)	C8—H8C	0.9600
O3—H1	1.03 (3)	C15—C16	1.484 (3)
O4—H2	1.24 (2)	C15—H15A	0.9700
O2—H2	1.25 (2)	C15—H15B	0.9700
C7—C5	1.472 (3)	C4—H4A	0.9600
C7—C8	1.486 (3)	C4—H4B	0.9600
C5—C6	1.485 (3)	C4—H4C	0.9600
C3—C4	1.493 (3)	C16—H16A	0.9600
C10—C9	1.386 (3)	C16—H16B	0.9600
C10—C11	1.386 (3)	C16—H16C	0.9600
C10—C14	1.496 (3)

N2—Co1—N1	81.59 (7)	C12—C13—H13A	118.8
N2—Co1—N3	178.54 (7)	C1—C2—H2A	109.5
N1—Co1—N3	99.23 (7)	C1—C2—H2B	109.5
N2—Co1—N4	98.39 (7)	H2A—C2—H2B	109.5
N1—Co1—N4	178.87 (7)	C1—C2—H2C	109.5
N3—Co1—N4	80.76 (7)	H2A—C2—H2C	109.5
N2—Co1—N5	90.80 (7)	H2B—C2—H2C	109.5
N1—Co1—N5	91.01 (7)	N5—C9—C10	121.97 (18)
N3—Co1—N5	90.38 (7)	N5—C9—H9A	119.0
N4—Co1—N5	90.12 (6)	C10—C9—H9A	119.0
N2—Co1—Cl1	89.12 (5)	C14—O6—C15	117.41 (17)
N1—Co1—Cl1	89.06 (5)	C12—C11—C10	119.16 (19)
N3—Co1—Cl1	89.69 (5)	C12—C11—H11A	120.4
N4—Co1—Cl1	89.81 (5)	C10—C11—H11A	120.4
N5—Co1—Cl1	179.89 (5)	O5—C14—O6	124.9 (2)
C5—N3—O3	119.37 (16)	O5—C14—C10	122.8 (2)
C5—N3—Co1	117.34 (14)	O6—C14—C10	112.29 (17)
O3—N3—Co1	123.28 (13)	C11—C12—C13	118.99 (19)
C1—N1—O1	122.39 (17)	C11—C12—H12A	120.5
C1—N1—Co1	116.07 (13)	C13—C12—H12A	120.5
O1—N1—Co1	121.49 (12)	C5—C6—H6A	109.5
C7—N4—O4	120.58 (17)	C5—C6—H6B	109.5
C7—N4—Co1	116.87 (14)	H6A—C6—H6B	109.5
O4—N4—Co1	122.54 (12)	C5—C6—H6C	109.5
N1—O1—H1	103.4 (10)	H6A—C6—H6C	109.5
C9—N5—C13	118.40 (17)	H6B—C6—H6C	109.5
C9—N5—Co1	121.94 (13)	C7—C8—H8A	109.5
C13—N5—Co1	119.66 (13)	C7—C8—H8B	109.5
N1—C1—C3	112.86 (17)	H8A—C8—H8B	109.5
N1—C1—C2	123.9 (2)	C7—C8—H8C	109.5
C3—C1—C2	123.21 (19)	H8A—C8—H8C	109.5
C3—N2—O2	121.02 (16)	H8B—C8—H8C	109.5
C3—N2—Co1	116.53 (14)	O6—C15—C16	111.49 (19)
O2—N2—Co1	122.42 (12)	O6—C15—H15A	109.3
N3—O3—H1	101.4 (14)	C16—C15—H15A	109.3
N4—O4—H2	104.4 (11)	O6—C15—H15B	109.3
N2—O2—H2	104.6 (11)	C16—C15—H15B	109.3
N4—C7—C5	112.56 (17)	H15A—C15—H15B	108.0
N4—C7—C8	123.8 (2)	C3—C4—H4A	109.5
C5—C7—C8	123.62 (18)	C3—C4—H4B	109.5
N3—C5—C7	112.44 (16)	H4A—C4—H4B	109.5
N3—C5—C6	124.2 (2)	C3—C4—H4C	109.5
C7—C5—C6	123.35 (19)	H4A—C4—H4C	109.5
N2—C3—C1	112.88 (17)	H4B—C4—H4C	109.5
N2—C3—C4	123.8 (2)	C15—C16—H16A	109.5
C1—C3—C4	123.29 (19)	C15—C16—H16B	109.5
C9—C10—C11	119.00 (19)	H16A—C16—H16B	109.5
C9—C10—C14	122.23 (19)	C15—C16—H16C	109.5
C11—C10—C14	118.77 (19)	H16A—C16—H16C	109.5
N5—C13—C12	122.48 (19)	H16B—C16—H16C	109.5
N5—C13—H13A	118.8

Experimental details

Crystal data
Chemical formula	[Co(C₄H₇N₂O₂)₂Cl(C₈H₉NO₂)]
M_r	475.77
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	8.1961 (11), 14.2224 (19), 17.365 (2)
β (°)	98.340 (2)
V (Å³)	2002.8 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.03
Crystal size (mm)	0.32 × 0.15 × 0.06

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2001)
T_min, T_max	0.830, 0.940
No. of measured, independent and observed [I > 2σ(I)] reflections	9364, 3532, 3104
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.076, 1.10
No. of reflections	3532
No. of parameters	272
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.28

Computer programs: APEX2 (Bruker, 2007), SAINT-Plus (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—Cl1	2.2326 (6)	Co1—N3	1.8970 (16)
Co1—N1	1.8925 (16)	Co1—N4	1.9020 (16)
Co1—N2	1.8872 (16)	Co1—N5	1.9701 (15)

Acknowledgements

We are grateful to the Chinese National Natural Science Foundation (grant No. 21101057) and the Doctoral Fund of Henan University of Technology (No. 150389).

References

Bakac, A. & Espenson, J. H. (1984). J. Am. Chem. Soc. 106, 5197–5202. CrossRef CAS Web of Science Google Scholar
Bhuyan, M., Laskar, M., Mandal, D. & Gupta, B. D. (2007). Organometallics, 26, 3559–3567. Web of Science CSD CrossRef CAS Google Scholar
Bruker (2001). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Bruker (2007). SAINT-Plus and APEX2. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Dutta, G., Kumar, K. & Gupta, B. D. (2009). Organometallics, 28, 3485–3491. Web of Science CSD CrossRef CAS Google Scholar
Magnuson, V. E. & Weber, J. H. (1974). J. Organomet. Chem. 74, 135–141. CrossRef CAS Web of Science Google Scholar
Mandal, D. & Gupta, B. D. (2005). Organometallics, 24, 1501–1510. Web of Science CSD CrossRef CAS Google Scholar
Mandal, D. & Gupta, B. D. (2007). Organometallics, 26, 658–670. Web of Science CSD CrossRef CAS Google Scholar
Razavet, M., Artero, V. & Fontecave, M. (2005). Inorg. Chem. 44, 4786–4795. Web of Science CrossRef PubMed CAS Google Scholar
Schrayzer, G. N. (1968). Acc. Chem. Res. 1, 97–103. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Zangrando, E., Trani, M., Stabon, E., Carfagna, C., Milani, B. & Mestroni, G. (2003). Eur. J. Inorg. Chem. pp. 2683–2692. 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.