Tris(3,5-dimethyl-1H-pyrazole-κN2)(pyridine-2,6-dicarboxyl­ato-κ3O2,N,O6)cobalt(II) monohydrate

Lin, K.-H.; Yu, Z.-Y.; Zhong, Y.-H.; Shao, M.

doi:10.1107/S1600536809010538

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m449

doi:10.1107/S1600536809010538

Open

access

Tris(3,5-dimethyl-1H-pyrazole-κN²)(pyridine-2,6-dicarboxylato-κ³O²,N,O⁶)cobalt(II) monohydrate

Kun-Hua Lin,^a Zhe-Yin Yu,^a ^* Yan-Hua Zhong ^a and Min Shao ^b

^aDepartment of Chemistry, College of Science, Shanghai University, Shanghai 200444, People's Republic of China, and ^bInstrumental Analysis and Research Center, Shanghai University, Shanghai 200444, People's Republic of China
^*Correspondence e-mail: yuzheyin@shu.edu.cn

(Received 16 February 2009; accepted 23 March 2009; online 28 March 2009)

The reaction of Co(NO₃)₂·3H₂O with pyridine-2,6-dicarboxylic acid and 3,5-dimethyl-1H-pyrazole in a 1:1:3 molar ratio affords the title complex, [Co(C₇H₃NO₄)(C₅H₈N₂)₃]·H₂O. The Co^II atom is coordinated by one pyridine-2,6-dicarboxylate chelating ligand and three 3,5-dimethyl-1H-pyrazole ligands in a distorted octahedral geometry. Hydrogen-bonding interactions involving the coordinated carboxylate group, 3,5-dimethyl-1H-pyrazole and water help to consolidate the crystal structure

Related literature

For the use of complexes with pyrazole-based ligands in studying the relationship between the structure and the activity of the active site of metalloproteins, see: Haanstra et al. (1990 ). For the coordination modes of pyrazole complexes, see: Grotjahn et al. (2003 ).

Experimental

Crystal data

[Co(C₇H₃NO₄)(C₅H₈N₂)₃]·H₂O
M_r = 530.45
Triclinic, $[P \overline 1]$
a = 8.4220 (8) Å
b = 11.9936 (12) Å
c = 13.1418 (13) Å
α = 75.1290 (10)°
β = 84.7720 (10)°
γ = 70.0940 (10)°
V = 1206.3 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.76 mm⁻¹
T = 296 K
0.30 × 0.30 × 0.25 mm

Data collection

Bruker SMART CCD area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.804, T_max = 0.833
6298 measured reflections
4183 independent reflections
3769 reflections with I > 2σ(I)
R_int = 0.014

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.077
S = 1.03
4183 reflections
331 parameters
2 restraints
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

Co1—N1	2.0407 (16)
Co1—N4	2.0798 (16)
Co1—O1	2.1453 (14)
Co1—O3	2.1522 (14)
Co1—N2	2.2336 (17)
Co1—N6	2.2477 (17)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3A⋯O1Wⁱ	0.86	2.22	2.926 (2)	139
N3—H3A⋯O1	0.86	2.61	3.048 (2)	113
N5—H5⋯O2ⁱⁱ	0.86	2.10	2.945 (2)	168
N7—H7⋯O2ⁱⁱ	0.86	2.08	2.838 (2)	146
N7—H7⋯O3	0.86	2.42	2.906 (2)	116
O1W—H1WA⋯O4ⁱⁱⁱ	0.844 (17)	1.967 (18)	2.797 (2)	168 (3)
O1W—H1WB⋯O3^iv	0.828 (17)	2.204 (19)	3.009 (2)	164 (3)
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) x-1, y, z; (iii) x, y+1, z; (iv) -x, -y+1, -z+1.

Data collection: SMART (Bruker, 2000 ); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809010538/bq2127sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809010538/bq2127Isup2.hkl

checkCIF report

Comment top

Complexes with pyrazole-based ligands are a frequent subject of chemical investigations giving an opportunity for a better understanding of the relationship between the structure and the activity of the active site of metalloproteins (Haanstra et al., 1990). Nowadays, attention is paid to the design of various pyrazole ligands, and some coordination modes of pyrazole complexes were reported (Grotjahn et al., 2003). In our systematic studies on transition metal comlexes with the pyrazole derivatives, the title compound was prepared and its X-ray structure is presented here.

The molecular structure of the title compound is shown in Fig. 1. The compound assumes a distorted octahedron geometry, formed by three 3,5-Dimethyl-1-H-pyrazole molecules and a pyridine-2,6-dicarboxylate. Tridentate ligand pyridine-2,6-dicarboxylate dianion chelates to the Co atom by a N atom of pyridine ring and two O atoms of carboxyl groups with a meridional configuration. Monodentate ligand 3,5-Dimethyl-1-H-pyrazole coordinated to the Co atom by N atoms of pyrazole rings. The bond distances of Co1—N1 and Co1—N4 are 2.0407 (16)Å and 2.0798 (16)Å (Table 1), which are shorter than the the bond distances of Co1—N2 and Co1—N6 with 2.2336 (17)Å and 2.2477 (17)Å.

Related literature top

For the use of complexes with pyrazole-based ligands in studying the relationship between the structure and the activity of the active site of metalloproteins, see: Haanstra et al. (1990). For the coordination modes of pyrazole complexes, see: Grotjahn et al. (2003).

Experimental top

An ethanol solution (6 ml) containing 3,5-Dimethyl-1-H-pyrazole(0.1153 g, 1.2 mmol) and Co(NO₃)₂.3H₂O(0.0870 g, 0.3 mmol) was mixed with an aqueous solution (6 ml) of pyridine-2,6-dicarboxylic acid(0.0501 g, 0.3 mmol) and NaOH (0.0240 g, 0.6 mmol). The mixture was refluxed for 6 h. The solution was filtered after cooling to room temperature. Pink single crystals suitable for X-ray diffraction were obtained from the filtrate after 11 d.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of (I) with displacement ellipsoids drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I).

Tris(3,5-dimethyl-1H-pyrazole-κN²)(pyridine-2,6- dicarboxylato-κ³O²,N,O⁶)cobalt(II) monohydrate top

Crystal data top

[Co(C₇H₃NO₄)(C₅H₈N₂)₃]·H₂O	Z = 2
M_r = 530.45	F(000) = 554
Triclinic, P1	D_x = 1.460 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.4220 (8) Å	Cell parameters from 4060 reflections
b = 11.9936 (12) Å	θ = 2.7–27.5°
c = 13.1418 (13) Å	µ = 0.76 mm⁻¹
α = 75.129 (1)°	T = 296 K
β = 84.772 (1)°	Block, pink
γ = 70.094 (1)°	0.30 × 0.30 × 0.25 mm
V = 1206.3 (2) Å³

Data collection top

Bruker SMART CCD area-detector diffractometer	4183 independent reflections
Radiation source: fine-focus sealed tube	3769 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.014
ϕ and ω scans	θ_max = 25.1°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→9
T_min = 0.804, T_max = 0.833	k = −14→14
6298 measured reflections	l = −13→15

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)] = 0.030	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.077	w = 1/[σ²(F_o²) + (0.0334P)² + 0.7243P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.002
4183 reflections	Δρ_max = 0.25 e Å⁻³
331 parameters	Δρ_min = −0.25 e Å⁻³
2 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: 0.0176 (11)

Crystal data top

[Co(C₇H₃NO₄)(C₅H₈N₂)₃]·H₂O	γ = 70.094 (1)°
M_r = 530.45	V = 1206.3 (2) Å³
Triclinic, P1	Z = 2
a = 8.4220 (8) Å	Mo Kα radiation
b = 11.9936 (12) Å	µ = 0.76 mm⁻¹
c = 13.1418 (13) Å	T = 296 K
α = 75.129 (1)°	0.30 × 0.30 × 0.25 mm
β = 84.772 (1)°

Data collection top

Bruker SMART CCD area-detector diffractometer	4183 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	3769 reflections with I > 2σ(I)
T_min = 0.804, T_max = 0.833	R_int = 0.014
6298 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	2 restraints
wR(F²) = 0.077	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.25 e Å⁻³
4183 reflections	Δρ_min = −0.25 e Å⁻³
331 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	0.33263 (3)	0.28250 (2)	0.246751 (19)	0.02818 (10)
C1	0.5981 (2)	0.24913 (18)	0.39330 (15)	0.0295 (4)
C2	0.6852 (3)	0.2085 (2)	0.48700 (17)	0.0392 (5)
H2	0.7859	0.2228	0.4914	0.047*
C3	0.6195 (3)	0.1461 (2)	0.57368 (17)	0.0457 (6)
H3	0.6770	0.1171	0.6373	0.055*
C4	0.4680 (3)	0.1260 (2)	0.56719 (17)	0.0398 (5)
H4	0.4220	0.0853	0.6259	0.048*
C5	0.3884 (3)	0.16841 (17)	0.47115 (15)	0.0308 (4)
C6	0.6491 (2)	0.31692 (18)	0.28856 (16)	0.0310 (4)
C7	0.2218 (3)	0.15601 (18)	0.44770 (17)	0.0339 (5)
C8	0.7310 (3)	−0.0243 (2)	0.15919 (17)	0.0369 (5)
C9	0.5995 (3)	−0.0532 (2)	0.13323 (17)	0.0400 (5)
H9	0.6068	−0.1179	0.1042	0.048*
C10	0.4521 (3)	0.03249 (19)	0.15849 (15)	0.0330 (4)
C11	0.2751 (3)	0.0397 (2)	0.14480 (18)	0.0418 (5)
H11A	0.2067	0.0675	0.2017	0.063*
H11B	0.2726	−0.0397	0.1446	0.063*
H11C	0.2318	0.0960	0.0792	0.063*
C12	0.9178 (3)	−0.0810 (2)	0.1495 (2)	0.0549 (7)
H12A	0.9611	−0.0264	0.0971	0.082*
H12B	0.9424	−0.1565	0.1292	0.082*
H12C	0.9699	−0.0965	0.2160	0.082*
C13	0.2400 (2)	0.34373 (19)	0.00957 (15)	0.0327 (4)
C14	0.1089 (3)	0.3533 (2)	−0.05258 (16)	0.0361 (5)
H14	0.1106	0.3631	−0.1252	0.043*
C15	−0.0231 (3)	0.34544 (19)	0.01417 (16)	0.0340 (5)
C16	−0.1946 (3)	0.3455 (3)	−0.0043 (2)	0.0491 (6)
H16A	−0.1863	0.2693	−0.0190	0.074*
H16B	−0.2450	0.4114	−0.0632	0.074*
H16C	−0.2632	0.3558	0.0572	0.074*
C17	0.4138 (3)	0.3448 (3)	−0.02341 (18)	0.0479 (6)
H17A	0.4612	0.3677	0.0286	0.072*
H17B	0.4089	0.4027	−0.0899	0.072*
H17C	0.4832	0.2649	−0.0302	0.072*
C18	−0.0812 (3)	0.5490 (2)	0.36524 (17)	0.0381 (5)
C19	0.0209 (3)	0.6189 (2)	0.35379 (19)	0.0439 (5)
H19	−0.0057	0.6941	0.3704	0.053*
C20	0.1734 (3)	0.5549 (2)	0.31215 (17)	0.0375 (5)
C21	0.3282 (3)	0.5905 (2)	0.2884 (2)	0.0546 (6)
H21A	0.3927	0.5666	0.3516	0.082*
H21B	0.2966	0.6774	0.2615	0.082*
H21C	0.3950	0.5504	0.2368	0.082*
C22	−0.2576 (3)	0.5668 (3)	0.4048 (2)	0.0580 (7)
H22A	−0.3351	0.6281	0.3534	0.087*
H22B	−0.2709	0.5926	0.4694	0.087*
H22C	−0.2804	0.4913	0.4172	0.087*
N1	0.45453 (19)	0.22688 (14)	0.38745 (12)	0.0272 (3)
N2	0.4898 (2)	0.11200 (15)	0.19911 (13)	0.0322 (4)
N3	0.6621 (2)	0.07452 (16)	0.19804 (14)	0.0342 (4)
H3A	0.7201	0.1105	0.2200	0.041*
N4	0.1920 (2)	0.33111 (15)	0.11058 (13)	0.0309 (4)
N5	0.0297 (2)	0.33282 (16)	0.11091 (13)	0.0316 (4)
H5	−0.0318	0.3265	0.1666	0.038*
N6	0.1671 (2)	0.45011 (15)	0.29795 (13)	0.0330 (4)
N7	0.0095 (2)	0.44975 (16)	0.33138 (13)	0.0343 (4)
H7	−0.0280	0.3916	0.3308	0.041*
O1	0.55090 (18)	0.33974 (14)	0.21281 (11)	0.0362 (3)
O2	0.77947 (18)	0.34440 (15)	0.28302 (12)	0.0418 (4)
O3	0.18031 (17)	0.18992 (13)	0.35129 (11)	0.0353 (3)
O4	0.1395 (2)	0.11702 (16)	0.52179 (13)	0.0552 (5)
O1W	0.0578 (2)	0.93763 (17)	0.67852 (14)	0.0487 (4)
H1WA	0.073 (4)	0.989 (2)	0.6251 (17)	0.063 (9)*
H1WB	0.006 (4)	0.898 (3)	0.661 (2)	0.071 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02400 (16)	0.03763 (17)	0.02563 (15)	−0.01357 (12)	−0.00029 (10)	−0.00758 (11)
C1	0.0247 (10)	0.0335 (11)	0.0329 (10)	−0.0085 (8)	−0.0003 (8)	−0.0137 (8)
C2	0.0330 (12)	0.0478 (13)	0.0395 (12)	−0.0118 (10)	−0.0058 (9)	−0.0153 (10)
C3	0.0481 (14)	0.0498 (14)	0.0333 (12)	−0.0075 (11)	−0.0119 (10)	−0.0076 (10)
C4	0.0483 (13)	0.0369 (12)	0.0299 (11)	−0.0115 (10)	0.0013 (9)	−0.0046 (9)
C5	0.0355 (11)	0.0271 (10)	0.0296 (10)	−0.0097 (8)	0.0037 (8)	−0.0086 (8)
C6	0.0268 (11)	0.0354 (11)	0.0362 (11)	−0.0132 (9)	0.0039 (8)	−0.0153 (9)
C7	0.0353 (11)	0.0289 (10)	0.0399 (12)	−0.0137 (9)	0.0074 (9)	−0.0110 (9)
C8	0.0319 (11)	0.0424 (12)	0.0374 (11)	−0.0109 (9)	0.0036 (9)	−0.0145 (9)
C9	0.0385 (12)	0.0447 (13)	0.0433 (12)	−0.0144 (10)	0.0036 (10)	−0.0225 (10)
C10	0.0330 (11)	0.0400 (11)	0.0289 (10)	−0.0154 (9)	0.0009 (8)	−0.0092 (9)
C11	0.0355 (12)	0.0514 (14)	0.0454 (13)	−0.0200 (10)	0.0013 (10)	−0.0161 (11)
C12	0.0348 (13)	0.0628 (16)	0.0710 (17)	−0.0104 (12)	0.0068 (12)	−0.0330 (14)
C13	0.0281 (11)	0.0414 (12)	0.0303 (10)	−0.0142 (9)	0.0014 (8)	−0.0083 (9)
C14	0.0319 (11)	0.0495 (13)	0.0277 (10)	−0.0148 (10)	−0.0011 (8)	−0.0086 (9)
C15	0.0268 (11)	0.0412 (12)	0.0344 (11)	−0.0106 (9)	−0.0042 (8)	−0.0090 (9)
C16	0.0282 (12)	0.0743 (17)	0.0508 (14)	−0.0197 (12)	−0.0037 (10)	−0.0206 (12)
C17	0.0347 (12)	0.0744 (17)	0.0414 (13)	−0.0274 (12)	0.0070 (10)	−0.0151 (12)
C18	0.0337 (11)	0.0404 (12)	0.0400 (12)	−0.0073 (9)	−0.0020 (9)	−0.0155 (10)
C19	0.0463 (14)	0.0381 (12)	0.0518 (14)	−0.0129 (10)	0.0001 (11)	−0.0203 (10)
C20	0.0400 (12)	0.0408 (12)	0.0369 (11)	−0.0180 (10)	−0.0015 (9)	−0.0113 (9)
C21	0.0520 (15)	0.0570 (16)	0.0689 (17)	−0.0317 (13)	0.0074 (13)	−0.0232 (13)
C22	0.0368 (13)	0.0637 (17)	0.0790 (19)	−0.0108 (12)	0.0106 (13)	−0.0379 (15)
N1	0.0257 (8)	0.0297 (8)	0.0276 (8)	−0.0098 (7)	0.0012 (7)	−0.0090 (7)
N2	0.0254 (9)	0.0382 (9)	0.0344 (9)	−0.0105 (7)	0.0008 (7)	−0.0113 (7)
N3	0.0262 (9)	0.0398 (10)	0.0410 (10)	−0.0130 (8)	0.0003 (7)	−0.0147 (8)
N4	0.0228 (8)	0.0404 (10)	0.0309 (9)	−0.0122 (7)	−0.0008 (7)	−0.0083 (7)
N5	0.0230 (8)	0.0447 (10)	0.0288 (9)	−0.0138 (7)	0.0028 (7)	−0.0090 (7)
N6	0.0285 (9)	0.0383 (10)	0.0350 (9)	−0.0130 (7)	0.0016 (7)	−0.0117 (7)
N7	0.0284 (9)	0.0369 (10)	0.0430 (10)	−0.0132 (8)	0.0024 (7)	−0.0167 (8)
O1	0.0334 (8)	0.0495 (9)	0.0309 (7)	−0.0221 (7)	0.0011 (6)	−0.0073 (6)
O2	0.0316 (8)	0.0559 (10)	0.0486 (9)	−0.0259 (7)	0.0041 (7)	−0.0168 (7)
O3	0.0315 (8)	0.0417 (8)	0.0382 (8)	−0.0186 (6)	0.0023 (6)	−0.0108 (6)
O4	0.0571 (11)	0.0660 (11)	0.0486 (10)	−0.0381 (9)	0.0155 (8)	−0.0056 (8)
O1W	0.0543 (11)	0.0579 (11)	0.0447 (10)	−0.0330 (9)	0.0035 (8)	−0.0123 (9)

Geometric parameters (Å, º) top

Co1—N1	2.0407 (16)	C13—N4	1.337 (3)
Co1—N4	2.0798 (16)	C13—C14	1.389 (3)
Co1—O1	2.1453 (14)	C13—C17	1.492 (3)
Co1—O3	2.1522 (14)	C14—C15	1.366 (3)
Co1—N2	2.2336 (17)	C14—H14	0.9300
Co1—N6	2.2477 (17)	C15—N5	1.340 (3)
C1—N1	1.337 (2)	C15—C16	1.486 (3)
C1—C2	1.380 (3)	C16—H16A	0.9600
C1—C6	1.515 (3)	C16—H16B	0.9600
C2—C3	1.376 (3)	C16—H16C	0.9600
C2—H2	0.9300	C17—H17A	0.9600
C3—C4	1.390 (3)	C17—H17B	0.9600
C3—H3	0.9300	C17—H17C	0.9600
C4—C5	1.376 (3)	C18—N7	1.337 (3)
C4—H4	0.9300	C18—C19	1.367 (3)
C5—N1	1.331 (2)	C18—C22	1.491 (3)
C5—C7	1.526 (3)	C19—C20	1.398 (3)
C6—O2	1.241 (2)	C19—H19	0.9300
C6—O1	1.267 (2)	C20—N6	1.336 (3)
C7—O4	1.229 (2)	C20—C21	1.489 (3)
C7—O3	1.270 (2)	C21—H21A	0.9600
C8—N3	1.338 (3)	C21—H21B	0.9600
C8—C9	1.362 (3)	C21—H21C	0.9600
C8—C12	1.494 (3)	C22—H22A	0.9600
C9—C10	1.393 (3)	C22—H22B	0.9600
C9—H9	0.9300	C22—H22C	0.9600
C10—N2	1.339 (3)	N2—N3	1.365 (2)
C10—C11	1.488 (3)	N3—H3A	0.8600
C11—H11A	0.9600	N4—N5	1.359 (2)
C11—H11B	0.9600	N5—H5	0.8600
C11—H11C	0.9600	N6—N7	1.361 (2)
C12—H12A	0.9600	N7—H7	0.8600
C12—H12B	0.9600	O1W—H1WA	0.844 (17)
C12—H12C	0.9600	O1W—H1WB	0.828 (17)

N1—Co1—N4	174.52 (6)	C13—C14—H14	126.9
N1—Co1—O1	75.49 (6)	N5—C15—C14	106.49 (17)
N4—Co1—O1	109.98 (6)	N5—C15—C16	121.66 (19)
N1—Co1—O3	76.60 (6)	C14—C15—C16	131.8 (2)
N4—Co1—O3	97.92 (6)	C15—C16—H16A	109.5
O1—Co1—O3	152.00 (5)	C15—C16—H16B	109.5
N1—Co1—N2	91.87 (6)	H16A—C16—H16B	109.5
N4—Co1—N2	88.21 (6)	C15—C16—H16C	109.5
O1—Co1—N2	86.36 (6)	H16A—C16—H16C	109.5
O3—Co1—N2	92.37 (6)	H16B—C16—H16C	109.5
N1—Co1—N6	88.03 (6)	C13—C17—H17A	109.5
N4—Co1—N6	91.67 (6)	C13—C17—H17B	109.5
O1—Co1—N6	95.87 (6)	H17A—C17—H17B	109.5
O3—Co1—N6	85.33 (6)	C13—C17—H17C	109.5
N2—Co1—N6	177.66 (6)	H17A—C17—H17C	109.5
N1—C1—C2	120.37 (19)	H17B—C17—H17C	109.5
N1—C1—C6	112.56 (16)	N7—C18—C19	105.87 (19)
C2—C1—C6	127.04 (18)	N7—C18—C22	121.8 (2)
C3—C2—C1	118.3 (2)	C19—C18—C22	132.4 (2)
C3—C2—H2	120.8	C18—C19—C20	106.28 (19)
C1—C2—H2	120.8	C18—C19—H19	126.9
C2—C3—C4	120.7 (2)	C20—C19—H19	126.9
C2—C3—H3	119.6	N6—C20—C19	110.63 (19)
C4—C3—H3	119.6	N6—C20—C21	122.0 (2)
C5—C4—C3	117.9 (2)	C19—C20—C21	127.3 (2)
C5—C4—H4	121.1	C20—C21—H21A	109.5
C3—C4—H4	121.1	C20—C21—H21B	109.5
N1—C5—C4	120.88 (19)	H21A—C21—H21B	109.5
N1—C5—C7	113.15 (17)	C20—C21—H21C	109.5
C4—C5—C7	125.96 (19)	H21A—C21—H21C	109.5
O2—C6—O1	125.78 (19)	H21B—C21—H21C	109.5
O2—C6—C1	119.27 (18)	C18—C22—H22A	109.5
O1—C6—C1	114.94 (16)	C18—C22—H22B	109.5
O4—C7—O3	126.1 (2)	H22A—C22—H22B	109.5
O4—C7—C5	118.49 (19)	C18—C22—H22C	109.5
O3—C7—C5	115.42 (17)	H22A—C22—H22C	109.5
N3—C8—C9	106.06 (18)	H22B—C22—H22C	109.5
N3—C8—C12	122.1 (2)	C5—N1—C1	121.79 (17)
C9—C8—C12	131.8 (2)	C5—N1—Co1	118.58 (13)
C8—C9—C10	106.82 (19)	C1—N1—Co1	119.63 (13)
C8—C9—H9	126.6	C10—N2—N3	104.33 (16)
C10—C9—H9	126.6	C10—N2—Co1	133.05 (14)
N2—C10—C9	110.16 (18)	N3—N2—Co1	122.35 (12)
N2—C10—C11	122.52 (19)	C8—N3—N2	112.62 (16)
C9—C10—C11	127.32 (19)	C8—N3—H3A	123.7
C10—C11—H11A	109.5	N2—N3—H3A	123.7
C10—C11—H11B	109.5	C13—N4—N5	104.78 (15)
H11A—C11—H11B	109.5	C13—N4—Co1	130.69 (13)
C10—C11—H11C	109.5	N5—N4—Co1	123.41 (12)
H11A—C11—H11C	109.5	C15—N5—N4	112.05 (16)
H11B—C11—H11C	109.5	C15—N5—H5	124.0
C8—C12—H12A	109.5	N4—N5—H5	124.0
C8—C12—H12B	109.5	C20—N6—N7	104.03 (16)
H12A—C12—H12B	109.5	C20—N6—Co1	140.31 (14)
C8—C12—H12C	109.5	N7—N6—Co1	115.57 (12)
H12A—C12—H12C	109.5	C18—N7—N6	113.19 (17)
H12B—C12—H12C	109.5	C18—N7—H7	123.4
N4—C13—C14	110.39 (17)	N6—N7—H7	123.4
N4—C13—C17	121.13 (18)	C6—O1—Co1	117.38 (12)
C14—C13—C17	128.48 (19)	C7—O3—Co1	115.59 (12)
C15—C14—C13	106.29 (18)	H1WA—O1W—H1WB	110 (3)
C15—C14—H14	126.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Wⁱ	0.86	2.22	2.926 (2)	139
N3—H3A···O1	0.86	2.61	3.048 (2)	113
N5—H5···O2ⁱⁱ	0.86	2.10	2.945 (2)	168
N7—H7···O2ⁱⁱ	0.86	2.08	2.838 (2)	146
N7—H7···O3	0.86	2.42	2.906 (2)	116
O1W—H1WA···O4ⁱⁱⁱ	0.84 (2)	1.97 (2)	2.797 (2)	168 (3)
O1W—H1WB···O3^iv	0.83 (2)	2.20 (2)	3.009 (2)	164 (3)

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

Experimental details

Crystal data
Chemical formula	[Co(C₇H₃NO₄)(C₅H₈N₂)₃]·H₂O
M_r	530.45
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.4220 (8), 11.9936 (12), 13.1418 (13)
α, β, γ (°)	75.129 (1), 84.772 (1), 70.094 (1)
V (Å³)	1206.3 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.76
Crystal size (mm)	0.30 × 0.30 × 0.25

Data collection
Diffractometer	Bruker SMART CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.804, 0.833
No. of measured, independent and observed [I > 2σ(I)] reflections	6298, 4183, 3769
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.077, 1.03
No. of reflections	4183
No. of parameters	331
No. of restraints	2
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.25

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Co1—N1	2.0407 (16)	Co1—O3	2.1522 (14)
Co1—N4	2.0798 (16)	Co1—N2	2.2336 (17)
Co1—O1	2.1453 (14)	Co1—N6	2.2477 (17)

N1—Co1—N4	174.52 (6)	N4—Co1—N2	88.21 (6)
N1—Co1—O1	75.49 (6)	N4—Co1—N6	91.67 (6)
N1—Co1—O3	76.60 (6)	N2—Co1—N6	177.66 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3A···O1Wⁱ	0.86	2.22	2.926 (2)	138.9
N3—H3A···O1	0.86	2.61	3.048 (2)	112.6
N5—H5···O2ⁱⁱ	0.86	2.10	2.945 (2)	167.6
N7—H7···O2ⁱⁱ	0.86	2.08	2.838 (2)	146.3
N7—H7···O3	0.86	2.42	2.906 (2)	116.3
O1W—H1WA···O4ⁱⁱⁱ	0.844 (17)	1.967 (18)	2.797 (2)	168 (3)
O1W—H1WB···O3^iv	0.828 (17)	2.204 (19)	3.009 (2)	164 (3)

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

References

Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Grotjahn, D. B., Van, S., Combs, D., Daniel, A., Schneider, C., Incarvito, C. D., Lam, K.-C., Rossi, G., Rheingold, A. L., Rideout, M., Meyer, C., Hernandez, G. & Mejorado, L. (2003). Inorg. Chem. 42, 3347–3355. Web of Science CSD CrossRef PubMed CAS Google Scholar
Haanstra, W. G., Van der Donk, W. A. J. W., Driessen, W. L., Reedijk, J., Wood, J. S. & Drew, M. G. B. (1990). J. Chem. Soc. Dalton Trans. 10, 3123–3128. CSD CrossRef Web of Science 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

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.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page m449

doi:10.1107/S1600536809010538

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

metal-organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)