(Ethyl­enediamine-κ2N,N)bis[2-(pyridin-2-yl-κN)-1,3-imidazol-1-ido-κN1]cobalt(III) nitrate monohydrate

Feng, X.-L.; Zhang, Y.-P.

doi:10.1107/S1600536812032692

(Ethylenediamine-κ²N,N)bis[2-(pyridin-2-yl-κN)-1,3-imidazol-1-ido-κN¹]cobalt(III) nitrate monohydrate

In the title compound, [Co(C₈H₆N₃)₂(C₂H₈N₂)]NO₃·H₂O, the Co^III ion is coordinated by four N atoms from two 2-(pyridin-2-yl)-1,3-imidazol-1-ide ligands and two N atoms of ethylenediamine in a distorted octahedral geometry. In the crystal, classical N—H

N(O) and O—H

N(O) hydrogen bonds connect all the isolated components together to yield a three-dimensional structure.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536812032692/cv5321sup1.cif Contains datablocks I, global
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536812032692/cv5321Isup2.hkl Contains datablock I

CCDC reference: 891205

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
R factor = 0.037
wR factor = 0.110
Data-to-parameter ratio = 12.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT244_ALERT_4_C Low   'Solvent' Ueq as Compared to Neighbors of          N9
PLAT905_ALERT_3_C Negative K value in the Analysis of Variance ...     -1.713
PLAT910_ALERT_3_C Missing # of FCF Reflections Below Th(Min) .....          3
PLAT911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L=  0.595         68
PLAT976_ALERT_2_C Negative Residual Density at 0.97A from O4     .      -0.41 eA-3
PLAT976_ALERT_2_C Negative Residual Density at 0.87A from O4     .      -0.40 eA-3

Alert level G
PLAT005_ALERT_5_G No _iucr_refine_instructions_details in CIF ....          ?
PLAT007_ALERT_5_G Note: Number of Unrefined D-H Atoms ............          6
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          1
            N4  -CO1 -N1  -C1     39.50  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #          6
            N4  -CO1 -N1  -C3   -137.40  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         13
            N8  -CO1 -N3  -C8   -167.70  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         18
            N8  -CO1 -N3  -C4     16.10  1.70   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         21
            N1  -CO1 -N4  -C9     43.20  1.00   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         26
            N1  -CO1 -N4  -C11  -131.40  0.80   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         34
            N7  -CO1 -N6  -C16  -142.20  1.50   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         39
            N7  -CO1 -N6  -C12    40.50  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         45
            N6  -CO1 -N7  -C17    71.90  1.60   1.555   1.555   1.555   1.555
PLAT710_ALERT_4_G Delete 1-2-3 or 2-3-4 Linear Torsion Angle ... #         49
            N3  -CO1 -N8  -C18    86.70  1.60   1.555   1.555   1.555   1.555
PLAT909_ALERT_3_G Percentage of Observed Data at Theta(Max) still          60 Perc.

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   6 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  14 ALERT level G = General information/check it is not something unexpected

   1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   4 ALERT type 3 Indicator that the structure quality may be low
  11 ALERT type 4 Improvement, methodology, query or suggestion
   2 ALERT type 5 Informative message, check

Comment top

Organometallic complexes with the 2-(2-pyridyl)imidazole ligand (Dosser & Underhill, 1972; Lan et al., 2008) are intensively studied due to their magnetic properties (Carranza et al., 2009; Schott et al., 2011). Herewith we report the crystal structure of the title compound, (I) - a Co(III) complex with 2-(2-pyridyl)imidazolato ligands.

In (I) (Fig. 1), Co(III) ion is chelated by one ethylenediamine and two 2-(2-pyridyl)imidazolato ligands being coordinated by six N atoms in a distorted octahedral geometry. The bite angles of ethylenediamine and 2-(2-pyridyl)imidazolato chelate ligands to the cobalt atom are ca 84.72 (11)° and 89.02 (11)°, respectively. An extensive hydrogen-bonding network (Table 1) involving the N atoms of the ethylenediamine and 2-(2-pyridyl)imidazolato ligands, the water molecule and O atoms of nitrate anion interconnect all the isolated moieties together to yield a three-dimensional structure (Fig. 2).

Related literature top

For examples of metal–organic compounds containing the 2-(2-pyridyl)imidazole ligand, see: Dosser & Underhill (1972); Lan et al. (2008). For applications of these compounds, see: Carranza et al. (2009); Schott et al.(2011).

Experimental top

An ethanol solution (7 ml) of 2-(2-pyridyl)imidazole (0.5 mmol) was slowly added to an aqueous solution (8 ml) of Co(NO₃)₂.6H₂O (0.5 mmol) and ethylenediamine (2 mmol). Red block crystals were obtained after two months.

Computing details top

Data collection: SMART (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. View of (I) showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms have been omitted for clarity.
	Fig. 2. A portion of the crystal packing showing hydrogen bonds by dashed lines.

(Ethylenediamine-κ²N,N)bis[2-(pyridin-2-yl-κN)- 1,3-imidazol-1-ido-κN¹]cobalt(III) nitrate monohydrate top

Crystal data top

[Co(C₈H₆N₃)₂(C₂H₈N₂)]NO₃·H₂O	Z = 2
M_r = 487.38	F(000) = 504
Triclinic, P1	D_x = 1.513 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6669 (5) Å	Cell parameters from 2876 reflections
b = 11.0574 (8) Å	θ = 2.6–28.0°
c = 12.5304 (10) Å	µ = 0.85 mm⁻¹
α = 76.133 (2)°	T = 298 K
β = 75.672 (2)°	Block, red
γ = 68.797 (1)°	0.45 × 0.38 × 0.30 mm
V = 1069.62 (13) Å³

Data collection top

Bruker SMART 1000 CCD diffractometer	3714 independent reflections
Radiation source: fine-focus sealed tube	2907 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.021
ϕ and ω scans	θ_max = 25.0°, θ_min = 2.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −7→10
T_min = 0.699, T_max = 0.783	k = −13→13
5376 measured reflections	l = −10→14

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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	w = 1/[σ²(F_o²) + (0.0517P)² + 0.5557P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3714 reflections	Δρ_max = 0.32 e Å⁻³
289 parameters	Δρ_min = −0.42 e Å⁻³
0 restraints

Crystal data top

[Co(C₈H₆N₃)₂(C₂H₈N₂)]NO₃·H₂O	γ = 68.797 (1)°
M_r = 487.38	V = 1069.62 (13) Å³
Triclinic, P1	Z = 2
a = 8.6669 (5) Å	Mo Kα radiation
b = 11.0574 (8) Å	µ = 0.85 mm⁻¹
c = 12.5304 (10) Å	T = 298 K
α = 76.133 (2)°	0.45 × 0.38 × 0.30 mm
β = 75.672 (2)°

Data collection top

Bruker SMART 1000 CCD diffractometer	3714 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2907 reflections with I > 2σ(I)
T_min = 0.699, T_max = 0.783	R_int = 0.021
5376 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.037	289 parameters
wR(F²) = 0.110	0 restraints
S = 1.05	Δρ_max = 0.32 e Å⁻³
3714 reflections	Δρ_min = −0.42 e Å⁻³

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	0.49327 (4)	0.24908 (3)	0.25014 (3)	0.03109 (14)
N1	0.3734 (3)	0.3487 (2)	0.13063 (18)	0.0349 (5)
N2	0.2556 (3)	0.5498 (2)	0.03542 (19)	0.0427 (6)
N3	0.4925 (3)	0.4242 (2)	0.26227 (18)	0.0334 (5)
N4	0.5997 (3)	0.1632 (2)	0.37782 (17)	0.0318 (5)
N5	0.5660 (3)	0.1121 (2)	0.56550 (18)	0.0413 (6)
N6	0.2860 (3)	0.2713 (2)	0.36447 (19)	0.0353 (5)
N7	0.7032 (3)	0.2170 (2)	0.14273 (18)	0.0373 (5)
H7A	0.7057	0.2916	0.0949	0.045*
H7B	0.7911	0.1895	0.1785	0.045*
N8	0.4899 (3)	0.0816 (2)	0.23036 (18)	0.0364 (5)
H8A	0.4718	0.0319	0.2975	0.044*
H8B	0.4055	0.0949	0.1946	0.044*
N9	0.1402 (4)	0.0294 (3)	0.1721 (2)	0.0530 (7)
O1	0.2907 (3)	−0.0084 (3)	0.1286 (2)	0.0716 (7)
O2	0.0499 (4)	−0.0394 (3)	0.1852 (3)	0.1010 (11)
O3	0.0786 (4)	0.1364 (3)	0.2036 (3)	0.1008 (11)
O4	0.9518 (6)	0.7421 (6)	0.1433 (6)	0.251 (4)
H4C	0.9804	0.8031	0.1547	0.301*
H4D	1.0388	0.6873	0.1124	0.301*
C1	0.3419 (3)	0.4799 (3)	0.1174 (2)	0.0342 (6)
C2	0.2299 (4)	0.4556 (3)	−0.0051 (2)	0.0454 (7)
H2	0.1728	0.4724	−0.0636	0.054*
C3	0.3003 (4)	0.3323 (3)	0.0528 (2)	0.0431 (7)
H3	0.2983	0.2531	0.0409	0.052*
C4	0.4052 (3)	0.5251 (3)	0.1918 (2)	0.0353 (6)
C5	0.3797 (4)	0.6549 (3)	0.1971 (2)	0.0454 (7)
H5	0.3159	0.7230	0.1502	0.055*
C6	0.4492 (5)	0.6817 (3)	0.2719 (3)	0.0553 (9)
H6	0.4346	0.7682	0.2757	0.066*
C7	0.5412 (5)	0.5790 (3)	0.3417 (3)	0.0585 (9)
H7	0.5901	0.5955	0.3926	0.070*
C8	0.5597 (4)	0.4522 (3)	0.3350 (3)	0.0476 (8)
H8	0.6210	0.3834	0.3826	0.057*
C9	0.4922 (3)	0.1662 (3)	0.4763 (2)	0.0336 (6)
C10	0.7323 (4)	0.0724 (3)	0.5200 (2)	0.0457 (7)
H10	0.8187	0.0298	0.5609	0.055*
C11	0.7555 (4)	0.1034 (3)	0.4057 (2)	0.0416 (7)
H11	0.8578	0.0869	0.3566	0.050*
C12	0.3150 (4)	0.2280 (3)	0.4713 (2)	0.0363 (6)
C13	0.1848 (4)	0.2462 (3)	0.5620 (3)	0.0535 (8)
H13	0.2072	0.2190	0.6344	0.064*
C14	0.0221 (5)	0.3050 (4)	0.5436 (3)	0.0677 (10)
H14	−0.0673	0.3173	0.6034	0.081*
C15	−0.0066 (4)	0.3452 (4)	0.4357 (3)	0.0690 (11)
H15	−0.1162	0.3845	0.4222	0.083*
C16	0.1268 (4)	0.3275 (3)	0.3472 (3)	0.0518 (8)
H16	0.1058	0.3550	0.2745	0.062*
C17	0.7132 (4)	0.1148 (3)	0.0810 (2)	0.0495 (8)
H17A	0.8282	0.0759	0.0453	0.059*
H17B	0.6434	0.1531	0.0239	0.059*
C18	0.6521 (4)	0.0123 (3)	0.1648 (3)	0.0520 (8)
H18A	0.6369	−0.0485	0.1269	0.062*
H18B	0.7332	−0.0371	0.2136	0.062*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.0394 (2)	0.0299 (2)	0.0266 (2)	−0.01405 (16)	−0.01009 (15)	−0.00071 (14)
N1	0.0443 (13)	0.0330 (12)	0.0328 (12)	−0.0181 (11)	−0.0128 (10)	−0.0003 (10)
N2	0.0461 (14)	0.0413 (14)	0.0389 (13)	−0.0121 (11)	−0.0145 (11)	0.0003 (11)
N3	0.0393 (12)	0.0316 (12)	0.0321 (12)	−0.0134 (10)	−0.0094 (10)	−0.0037 (10)
N4	0.0398 (12)	0.0306 (12)	0.0274 (11)	−0.0154 (10)	−0.0070 (9)	−0.0015 (9)
N5	0.0557 (16)	0.0416 (14)	0.0306 (12)	−0.0203 (12)	−0.0124 (11)	−0.0010 (10)
N6	0.0393 (13)	0.0341 (12)	0.0354 (12)	−0.0137 (10)	−0.0096 (10)	−0.0052 (10)
N7	0.0456 (13)	0.0338 (12)	0.0305 (12)	−0.0138 (10)	−0.0078 (10)	0.0009 (10)
N8	0.0496 (14)	0.0357 (13)	0.0281 (12)	−0.0188 (11)	−0.0104 (10)	−0.0013 (10)
N9	0.0548 (18)	0.0607 (18)	0.0509 (16)	−0.0207 (15)	−0.0092 (13)	−0.0194 (14)
O1	0.0454 (14)	0.0897 (19)	0.0888 (19)	−0.0163 (13)	−0.0105 (13)	−0.0415 (16)
O2	0.077 (2)	0.112 (3)	0.142 (3)	−0.0543 (19)	0.0104 (19)	−0.064 (2)
O3	0.100 (2)	0.074 (2)	0.128 (3)	−0.0427 (18)	0.038 (2)	−0.052 (2)
O4	0.126 (4)	0.214 (6)	0.389 (10)	−0.007 (4)	0.033 (5)	−0.164 (7)
C1	0.0381 (15)	0.0319 (14)	0.0311 (14)	−0.0121 (12)	−0.0071 (11)	−0.0001 (11)
C2	0.0497 (17)	0.0535 (19)	0.0367 (16)	−0.0185 (15)	−0.0190 (13)	0.0005 (14)
C3	0.0534 (18)	0.0451 (17)	0.0393 (16)	−0.0229 (15)	−0.0169 (14)	−0.0026 (13)
C4	0.0375 (15)	0.0346 (15)	0.0324 (14)	−0.0123 (12)	−0.0041 (11)	−0.0039 (12)
C5	0.0570 (19)	0.0350 (16)	0.0419 (17)	−0.0139 (14)	−0.0082 (14)	−0.0041 (13)
C6	0.080 (2)	0.0385 (18)	0.054 (2)	−0.0238 (17)	−0.0104 (18)	−0.0120 (15)
C7	0.085 (3)	0.052 (2)	0.058 (2)	−0.0348 (19)	−0.0285 (19)	−0.0100 (17)
C8	0.0576 (19)	0.0460 (18)	0.0496 (18)	−0.0215 (15)	−0.0234 (15)	−0.0052 (14)
C9	0.0472 (16)	0.0294 (14)	0.0289 (14)	−0.0177 (12)	−0.0074 (12)	−0.0043 (11)
C10	0.0543 (19)	0.0497 (18)	0.0370 (16)	−0.0187 (15)	−0.0223 (14)	0.0038 (14)
C11	0.0404 (16)	0.0447 (17)	0.0398 (16)	−0.0138 (13)	−0.0132 (13)	−0.0004 (13)
C12	0.0458 (16)	0.0331 (15)	0.0338 (15)	−0.0177 (13)	−0.0056 (12)	−0.0064 (12)
C13	0.056 (2)	0.056 (2)	0.0438 (18)	−0.0184 (16)	−0.0002 (15)	−0.0083 (15)
C14	0.052 (2)	0.079 (3)	0.063 (2)	−0.0199 (19)	0.0076 (18)	−0.016 (2)
C15	0.0379 (18)	0.086 (3)	0.080 (3)	−0.0145 (18)	−0.0102 (18)	−0.016 (2)
C16	0.0452 (18)	0.059 (2)	0.055 (2)	−0.0163 (16)	−0.0173 (15)	−0.0084 (16)
C17	0.061 (2)	0.0477 (18)	0.0366 (16)	−0.0160 (16)	−0.0009 (14)	−0.0126 (14)
C18	0.069 (2)	0.0374 (17)	0.0482 (19)	−0.0168 (15)	−0.0047 (16)	−0.0100 (14)

Geometric parameters (Å, º) top

Co1—N4	1.919 (2)	C1—C4	1.447 (4)
Co1—N1	1.920 (2)	C2—C3	1.378 (4)
Co1—N8	1.938 (2)	C2—H2	0.9300
Co1—N7	1.949 (2)	C3—H3	0.9300
Co1—N3	1.976 (2)	C4—C5	1.387 (4)
Co1—N6	1.979 (2)	C5—C6	1.369 (4)
N1—C1	1.352 (3)	C5—H5	0.9300
N1—C3	1.364 (3)	C6—C7	1.380 (5)
N2—C1	1.339 (3)	C6—H6	0.9300
N2—C2	1.367 (4)	C7—C8	1.373 (4)
N3—C8	1.340 (4)	C7—H7	0.9300
N3—C4	1.358 (3)	C8—H8	0.9300
N4—C9	1.349 (3)	C9—C12	1.448 (4)
N4—C11	1.363 (3)	C10—C11	1.372 (4)
N5—C9	1.331 (3)	C10—H10	0.9300
N5—C10	1.361 (4)	C11—H11	0.9300
N6—C16	1.341 (4)	C12—C13	1.384 (4)
N6—C12	1.363 (3)	C13—C14	1.375 (5)
N7—C17	1.482 (4)	C13—H13	0.9300
N7—H7A	0.9000	C14—C15	1.373 (5)
N7—H7B	0.9000	C14—H14	0.9300
N8—C18	1.480 (4)	C15—C16	1.383 (5)
N8—H8A	0.9000	C15—H15	0.9300
N8—H8B	0.9000	C16—H16	0.9300
N9—O3	1.227 (4)	C17—C18	1.502 (4)
N9—O2	1.235 (4)	C17—H17A	0.9700
N9—O1	1.239 (3)	C17—H17B	0.9700
O4—H4C	0.8500	C18—H18A	0.9700
O4—H4D	0.8500	C18—H18B	0.9700

N4—Co1—N1	174.33 (9)	C2—C3—H3	126.5
N4—Co1—N8	89.92 (9)	N3—C4—C5	121.3 (3)
N1—Co1—N8	94.32 (9)	N3—C4—C1	112.4 (2)
N4—Co1—N7	94.58 (9)	C5—C4—C1	126.3 (3)
N1—Co1—N7	89.45 (10)	C6—C5—C4	119.3 (3)
N8—Co1—N7	86.37 (9)	C6—C5—H5	120.3
N4—Co1—N3	93.23 (9)	C4—C5—H5	120.3
N1—Co1—N3	82.56 (9)	C5—C6—C7	119.3 (3)
N8—Co1—N3	176.82 (9)	C5—C6—H6	120.3
N7—Co1—N3	92.92 (9)	C7—C6—H6	120.3
N4—Co1—N6	82.67 (9)	C8—C7—C6	119.1 (3)
N1—Co1—N6	93.44 (9)	C8—C7—H7	120.4
N8—Co1—N6	91.62 (9)	C6—C7—H7	120.4
N7—Co1—N6	176.60 (9)	N3—C8—C7	122.3 (3)
N3—Co1—N6	89.24 (9)	N3—C8—H8	118.8
C1—N1—C3	105.2 (2)	C7—C8—H8	118.8
C1—N1—Co1	113.99 (18)	N5—C9—N4	114.4 (2)
C3—N1—Co1	140.8 (2)	N5—C9—C12	129.0 (2)
C1—N2—C2	103.1 (2)	N4—C9—C12	116.6 (2)
C8—N3—C4	118.6 (2)	N5—C10—C11	110.9 (3)
C8—N3—Co1	127.1 (2)	N5—C10—H10	124.5
C4—N3—Co1	114.23 (18)	C11—C10—H10	124.5
C9—N4—C11	104.8 (2)	N4—C11—C10	106.8 (3)
C9—N4—Co1	114.15 (18)	N4—C11—H11	126.6
C11—N4—Co1	140.85 (19)	C10—C11—H11	126.6
C9—N5—C10	103.0 (2)	N6—C12—C13	121.5 (3)
C16—N6—C12	119.0 (3)	N6—C12—C9	112.5 (2)
C16—N6—Co1	127.1 (2)	C13—C12—C9	126.0 (3)
C12—N6—Co1	113.85 (18)	C14—C13—C12	119.1 (3)
C17—N7—Co1	108.11 (18)	C14—C13—H13	120.4
C17—N7—H7A	110.1	C12—C13—H13	120.4
Co1—N7—H7A	110.1	C15—C14—C13	119.0 (3)
C17—N7—H7B	110.1	C15—C14—H14	120.5
Co1—N7—H7B	110.1	C13—C14—H14	120.5
H7A—N7—H7B	108.4	C14—C15—C16	120.2 (3)
C18—N8—Co1	109.97 (18)	C14—C15—H15	119.9
C18—N8—H8A	109.7	C16—C15—H15	119.9
Co1—N8—H8A	109.7	N6—C16—C15	121.1 (3)
C18—N8—H8B	109.7	N6—C16—H16	119.5
Co1—N8—H8B	109.7	C15—C16—H16	119.5
H8A—N8—H8B	108.2	N7—C17—C18	107.1 (2)
O3—N9—O2	118.7 (3)	N7—C17—H17A	110.3
O3—N9—O1	120.1 (3)	C18—C17—H17A	110.3
O2—N9—O1	121.2 (3)	N7—C17—H17B	110.3
H4C—O4—H4D	108.4	C18—C17—H17B	110.3
N2—C1—N1	114.1 (2)	H17A—C17—H17B	108.5
N2—C1—C4	129.3 (2)	N8—C18—C17	107.4 (2)
N1—C1—C4	116.6 (2)	N8—C18—H18A	110.2
N2—C2—C3	110.6 (3)	C17—C18—H18A	110.2
N2—C2—H2	124.7	N8—C18—H18B	110.2
C3—C2—H2	124.7	C17—C18—H18B	110.2
N1—C3—C2	107.0 (3)	H18A—C18—H18B	108.5
N1—C3—H3	126.5

N4—Co1—N1—C1	39.5 (10)	C3—N1—C1—N2	−0.9 (3)
N8—Co1—N1—C1	177.82 (19)	Co1—N1—C1—N2	−178.86 (18)
N7—Co1—N1—C1	−95.86 (19)	C3—N1—C1—C4	179.4 (2)
N3—Co1—N1—C1	−2.85 (18)	Co1—N1—C1—C4	1.4 (3)
N6—Co1—N1—C1	85.94 (19)	C1—N2—C2—C3	0.0 (3)
N4—Co1—N1—C3	−137.4 (8)	C1—N1—C3—C2	0.9 (3)
N8—Co1—N1—C3	0.9 (3)	Co1—N1—C3—C2	177.9 (2)
N7—Co1—N1—C3	87.3 (3)	N2—C2—C3—N1	−0.6 (3)
N3—Co1—N1—C3	−179.7 (3)	C8—N3—C4—C5	−2.5 (4)
N6—Co1—N1—C3	−91.0 (3)	Co1—N3—C4—C5	174.0 (2)
N4—Co1—N3—C8	4.0 (3)	C8—N3—C4—C1	179.3 (2)
N1—Co1—N3—C8	−179.9 (3)	Co1—N3—C4—C1	−4.2 (3)
N8—Co1—N3—C8	−167.7 (15)	N2—C1—C4—N3	−177.8 (3)
N7—Co1—N3—C8	−90.8 (3)	N1—C1—C4—N3	1.9 (3)
N6—Co1—N3—C8	86.6 (2)	N2—C1—C4—C5	4.1 (5)
N4—Co1—N3—C4	−172.22 (19)	N1—C1—C4—C5	−176.2 (3)
N1—Co1—N3—C4	3.96 (18)	N3—C4—C5—C6	2.5 (4)
N8—Co1—N3—C4	16.1 (17)	C1—C4—C5—C6	−179.6 (3)
N7—Co1—N3—C4	93.02 (19)	C4—C5—C6—C7	−1.0 (5)
N6—Co1—N3—C4	−89.61 (19)	C5—C6—C7—C8	−0.5 (5)
N1—Co1—N4—C9	43.2 (10)	C4—N3—C8—C7	1.0 (5)
N8—Co1—N4—C9	−95.29 (19)	Co1—N3—C8—C7	−175.1 (2)
N7—Co1—N4—C9	178.36 (18)	C6—C7—C8—N3	0.5 (5)
N3—Co1—N4—C9	85.17 (19)	C10—N5—C9—N4	0.2 (3)
N6—Co1—N4—C9	−3.64 (18)	C10—N5—C9—C12	−179.1 (3)
N1—Co1—N4—C11	−131.4 (8)	C11—N4—C9—N5	−0.6 (3)
N8—Co1—N4—C11	90.1 (3)	Co1—N4—C9—N5	−177.08 (17)
N7—Co1—N4—C11	3.8 (3)	C11—N4—C9—C12	178.8 (2)
N3—Co1—N4—C11	−89.4 (3)	Co1—N4—C9—C12	2.3 (3)
N6—Co1—N4—C11	−178.3 (3)	C9—N5—C10—C11	0.3 (3)
N4—Co1—N6—C16	−178.3 (3)	C9—N4—C11—C10	0.7 (3)
N1—Co1—N6—C16	5.8 (3)	Co1—N4—C11—C10	175.6 (2)
N8—Co1—N6—C16	−88.6 (3)	N5—C10—C11—N4	−0.6 (3)
N7—Co1—N6—C16	−142.2 (15)	C16—N6—C12—C13	−3.0 (4)
N3—Co1—N6—C16	88.3 (3)	Co1—N6—C12—C13	174.4 (2)
N4—Co1—N6—C12	4.48 (18)	C16—N6—C12—C9	178.2 (2)
N1—Co1—N6—C12	−171.38 (19)	Co1—N6—C12—C9	−4.3 (3)
N8—Co1—N6—C12	94.19 (19)	N5—C9—C12—N6	−179.3 (2)
N7—Co1—N6—C12	40.5 (16)	N4—C9—C12—N6	1.4 (3)
N3—Co1—N6—C12	−88.87 (19)	N5—C9—C12—C13	2.0 (5)
N4—Co1—N7—C17	107.72 (18)	N4—C9—C12—C13	−177.3 (3)
N1—Co1—N7—C17	−76.28 (19)	N6—C12—C13—C14	2.4 (5)
N8—Co1—N7—C17	18.09 (18)	C9—C12—C13—C14	−179.0 (3)
N3—Co1—N7—C17	−158.80 (18)	C12—C13—C14—C15	−0.6 (6)
N6—Co1—N7—C17	71.9 (16)	C13—C14—C15—C16	−0.5 (6)
N4—Co1—N8—C18	−85.02 (19)	C12—N6—C16—C15	1.9 (5)
N1—Co1—N8—C18	98.7 (2)	Co1—N6—C16—C15	−175.2 (3)
N7—Co1—N8—C18	9.57 (19)	C14—C15—C16—N6	−0.2 (6)
N3—Co1—N8—C18	86.7 (16)	Co1—N7—C17—C18	−41.4 (3)
N6—Co1—N8—C18	−167.69 (19)	Co1—N8—C18—C17	−34.7 (3)
C2—N2—C1—N1	0.5 (3)	N7—C17—C18—N8	49.6 (3)
C2—N2—C1—C4	−179.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8B···O1	0.90	2.16	2.922 (4)	142
N8—H8A···N5ⁱ	0.90	2.09	2.979 (3)	168
N7—H7A···N2ⁱⁱ	0.90	2.15	3.045 (3)	171
N7—H7B···O3ⁱⁱⁱ	0.90	2.43	3.281 (5)	158
O4—H4D···N2ⁱⁱⁱ	0.85	2.12	2.974 (7)	180
O4—H4C···O2^iv	0.85	2.18	3.026 (7)	179

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

Experimental details

Crystal data
Chemical formula	[Co(C₈H₆N₃)₂(C₂H₈N₂)]NO₃·H₂O
M_r	487.38
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	8.6669 (5), 11.0574 (8), 12.5304 (10)
α, β, γ (°)	76.133 (2), 75.672 (2), 68.797 (1)
V (Å³)	1069.62 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.85
Crystal size (mm)	0.45 × 0.38 × 0.30

Data collection
Diffractometer	Bruker SMART 1000 CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.699, 0.783
No. of measured, independent and observed [I > 2σ(I)] reflections	5376, 3714, 2907
R_int	0.021
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.037, 0.110, 1.05
No. of reflections	3714
No. of parameters	289
Δρ_max, Δρ_min (e Å⁻³)	0.32, −0.42

Computer programs: SMART (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).