Diazido­bis­(5,5′-dimethyl-2,2′-bipyridyl-κ2N,N′)cobalt(II) monohydrate

Phatchimkun, J.; Chaichit, N.

doi:10.1107/S1600536811011305

metal-organic compounds

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ISSN: 2056-9890

Volume 67| Part 4| April 2011| Pages m516-m517

doi:10.1107/S1600536811011305

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Diazidobis(5,5′-dimethyl-2,2′-bipyridyl-κ²N,N′)cobalt(II) monohydrate

Jaturong Phatchimkun ^a ^* and Narongsak Chaichit ^b

^aDepartment of Computer Science, Faculty of Engineering, Vongchavalitkul University, Nakhon Ratchasima 30000, Thailand, and ^bDepartment of Physics, Faculty of Science and Technology, Thammasat University, Rangsit, Pathumthani 12121, Thailand
^*Correspondence e-mail: jaturong_phat@hotmail.com

(Received 16 March 2011; accepted 27 March 2011; online 31 March 2011)

In the title compound, [Co(C₁₂H₁₂N₂)₂(N₃)₂]·H₂O, the Co(II) ion is situated on a crystallographic twofold axis and adopts a distorted octahedral geometry with the two dmbpy (dmbpy = 5,5′-dimethyl-2,2′-bipyridyl) and the two azido ligands in a cis arrangement. The solvent water molecule and one methyl group of the dmbpy ligand are disordered over two sets of sites in a 1:1 ratio. The crystal structure is stabilized by intramolecular C—H⋯N(dmbpy) and intermolecular O—H⋯N(azide) hydrogen bonds.

Related literature

For related structures with dmbpy ligands, see: Phatchimkun et al. (2009 ); van Albada et al. (2004 , 2005 ); Catalan et al. (1995 ); Kooijman et al. (2002 ). For azido complexes, see: Ribas et al. (1999 ) and references therein. For Co—N bond lengths in azido-containing mononuclear Co(II) complexes, see: Cheng & Hu (2003 ). For a description of the Cambridge Structural Database, see: Allen (2002 ).

Experimental

Crystal data

[Co(C₁₂H₁₂N₂)₂(N₃)₂]·H₂O
M_r = 529.46
Orthorhombic, P b c n
a = 17.1030 (3) Å
b = 8.5544 (2) Å
c = 16.7062 (5) Å
V = 2444.22 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.74 mm⁻¹
T = 298 K
0.30 × 0.25 × 0.06 mm

Data collection

Nonius KappaCCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.801, T_max = 0.957
13768 measured reflections
2606 independent reflections
2176 reflections with I > 2σ(I)
R_int = 0.022

Refinement

R[F² > 2σ(F²)] = 0.024
wR(F²) = 0.067
S = 1.03
2606 reflections
208 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.16 e Å⁻³
Δρ_min = −0.25 e Å⁻³

Table 1
Selected bond lengths (Å)

Co1—N1	2.0907 (11)
Co1—N2	2.0929 (10)
Co1—N3	2.1095 (11)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1O⋯N3ⁱ	1.05 (5)	1.99 (5)	2.926 (3)	141 (4)
C3—H3⋯O1ⁱⁱ	1.00 (2)	2.51 (2)	3.392 (4)	147.1 (14)
C1—H1⋯N3ⁱⁱⁱ	0.991 (15)	2.485 (15)	3.1241 (18)	121.9 (11)
Symmetry codes: (i) $[-x+1, y-1, -z+{\script{3\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (iii) $[-x+1, y, -z+{\script{3\over 2}}]$ .

Data collection: COLLECT (Nonius, 2002 ); cell refinement: COLLECT and DENZO/SCALEPACK (Otwinowski & Minor, 1997 ); data reduction: DENZO/SCALEPACK; 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 I, global. DOI: 10.1107/S1600536811011305/fj2407sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811011305/fj2407Isup2.hkl

checkCIF report

Comment top

Over the last decades, much attention has been paid on azido bridging complexes in the molecule-based magnet research field because azide anion is not only a good bridging ligand for metal ions (such as Cu(II), Ni(II), Mn(II), Co(II) etc) but also an efficient magnetic coupler (Ribas, et al., 1999). On the other hand, azide can act as a monomeric ligand. More than 100 structures of compounds containing the azide anion and cobalt(II) have been reported in the Cambridge Structural Database (CSD; Version 5.29, November 2008 update; Allen, 2002). However, X-ray structures of monomeric compounds with Co^II and azide are very rare. Only 16 crystal structures of cobalt(II) azido monomeric complexes have been reported (CSD code: BAWSIC, FURHEF, GURLEK, HIWDOH, HOVVIX, KAVSIJ, LEXXIW, MIRYAO, MONMAE, OHITTEE, PUBXEQ, RAKFUE, RARHAU, RAZHOP, RETDIE, and RUPTIG). Currently, there is no one report of crystal structure containing Co^II and 5,5'-dimethyl-2,2'-bipyridyl. Here we report on another monomeric compound, namely [Co(dmbpy)₂(N₃)₂]. H₂O, where dmbpy is 5,5'-dimethyl-2,2'-bipyridyl.

It is found that Co ion is coordinated by four nitrogen atoms from dmbpy and two azido nitrogen atoms, taking a distorted octahedral geometry. The two bidentate ligands have a cis disposition around the metal ion, forming practically perpendicular planes [N1–Co–N1ⁱ 89.81 (6), N2–Co–N2ⁱ 175.94 (6)°]. The rigidity of these ligands causes the bond angles N1–Co–N2, 78.12 (4) to deviate significantly from orthogonality. This causes the geometry about the Co^II ion to deviate slightly from that of an ideal octahedron. The Co–N(dmbpy) bond distances in a complex [2.0916 (12) and 2.1091 (13) Å] are almost the same as those found in the Co(II) compound of [Co^II(phen)₂(N₃)₂] (2.067 (2)–2.114 (2) Å) (Cheng & Hu, 2003). Good agreement is observed between the Co–N(azido) bond distance of 2.1091 (13) Å and those reported (Cheng & Hu, 2003) for azido containing mononuclear cobalt(II) complexes. The crystal structure is stabilized by intramolecular C—H···N and intermolecular O—H···N hydrogen bonds (Table 1).

Related literature top

For related dmbpy structures, see: Phatchimkun et al. (2009); van Albada et al. (2004, 2005); Catalan et al. (1995); Kooijman et al. (2002). For azido complexes, see: Ribas et al. (1999) and references therein. For Co—N bond lengths in azido-containing mononuclear Co(II) complexes, see: Cheng & Hu (2003). For a description of the Cambridge Structural Database, see: Allen (2002).

Experimental top

Preparation of [Co(dmbpy)₂(N₃)₂]. H₂O. A warm solution of dmbpy (0.181 g, 1.0 mmol) in methanol (15 cm³) was added to a hot aqueous solution (10 cm³) of Co(CH₃COO)₂ (0.123 g, 0.5 mmol). An aqueous solution (10 cm³) of NaN₃ (0.081 g, 1.0 mmol) was then added to the reaction mixture. The pink solution was slowly evaporated at room temperature. Slightly red crystals of [Co(dmbpy)(N₃)₂] were deposited. The crystals were filtered off, washed with mother liquor and air-dried. Yield ca 75%. (Anal. Calc. for C₂₄H₂₆CoN₁₀O (%): C, 54.44; H, 4.95; N, 26.45. Found: C, 54.08; H, 4.72; N, 26.27). IR (in cm^-1): n_as(N₃) 2009 s, n(C—N) 1605 m, n(C—C) 1584 m.

Computing details top

Data collection: COLLECT (Nonius, 2002); cell refinement: COLLECT (Nonius, 2002) and DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK (Otwinowski & Minor, 1997); 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. A view of the title structure with the atom-numbering scheme and displacement ellipsoids drawn at the 30% probability level. H atoms have been omitted for clarity.

Diazidobis(5,5'-dimethyl-2,2'-bipyridyl-κ²N,N')cobalt(II) monohydrate top

Crystal data top

[Co(C₁₂H₁₂N₂)₂(N₃)₂]·H₂O	F(000) = 1096
M_r = 529.46	D_x = 1.439 Mg m⁻³
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 7908 reflections
a = 17.1030 (3) Å	θ = 0.5–0.6°
b = 8.5544 (2) Å	µ = 0.74 mm⁻¹
c = 16.7062 (5) Å	T = 298 K
V = 2444.22 (10) Å³	Plate, red
Z = 4	0.30 × 0.25 × 0.06 mm

Data collection top

Nonius KappaCCD diffractometer	2606 independent reflections
Radiation source: fine-focus sealed tube	2176 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.022
ω scans	θ_max = 26.7°, θ_min = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −21→20
T_min = 0.801, T_max = 0.957	k = −9→10
13768 measured reflections	l = −18→21

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)] = 0.024	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	w = 1/[σ²(F_o²) + (0.0369P)² + 0.4953P] where P = (F_o² + 2F_c²)/3
2606 reflections	(Δ/σ)_max = 0.001
208 parameters	Δρ_max = 0.16 e Å⁻³
0 restraints	Δρ_min = −0.25 e Å⁻³

Crystal data top

[Co(C₁₂H₁₂N₂)₂(N₃)₂]·H₂O	V = 2444.22 (10) Å³
M_r = 529.46	Z = 4
Orthorhombic, Pbcn	Mo Kα radiation
a = 17.1030 (3) Å	µ = 0.74 mm⁻¹
b = 8.5544 (2) Å	T = 298 K
c = 16.7062 (5) Å	0.30 × 0.25 × 0.06 mm

Data collection top

Nonius KappaCCD diffractometer	2606 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2176 reflections with I > 2σ(I)
T_min = 0.801, T_max = 0.957	R_int = 0.022
13768 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.024	0 restraints
wR(F²) = 0.067	H atoms treated by a mixture of independent and constrained refinement
S = 1.03	Δρ_max = 0.16 e Å⁻³
2606 reflections	Δρ_min = −0.25 e Å⁻³
208 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	Occ. (<1)
Co1	0.5000	0.74215 (2)	0.7500	0.02599 (9)
O1	0.4695 (2)	0.2010 (3)	0.7390 (2)	0.0867 (12)	0.50
N1	0.38268 (6)	0.73352 (12)	0.71511 (7)	0.0331 (2)
N2	0.45546 (6)	0.56878 (12)	0.82573 (6)	0.0324 (2)
N3	0.47390 (7)	0.91391 (14)	0.83657 (7)	0.0418 (3)
N4	0.41325 (7)	0.92089 (14)	0.87142 (7)	0.0386 (3)
N5	0.35504 (8)	0.9289 (2)	0.90686 (9)	0.0648 (4)
C1	0.35034 (8)	0.81583 (17)	0.65500 (8)	0.0376 (3)
C2	0.27051 (8)	0.81862 (18)	0.63952 (9)	0.0417 (3)
C3	0.22267 (9)	0.73661 (18)	0.69218 (10)	0.0473 (4)
C4	0.25489 (9)	0.65180 (19)	0.75451 (9)	0.0437 (3)
C5	0.33587 (7)	0.64967 (16)	0.76406 (7)	0.0338 (3)
C6	0.37688 (7)	0.55243 (15)	0.82431 (7)	0.0331 (3)
C7	0.33975 (9)	0.44448 (18)	0.87336 (9)	0.0443 (3)
C8	0.38418 (9)	0.34791 (18)	0.92141 (9)	0.0468 (4)
C9	0.46490 (9)	0.35865 (16)	0.92140 (8)	0.0394 (3)
C10	0.49719 (8)	0.47402 (16)	0.87300 (8)	0.0369 (3)
C11	0.51626 (11)	0.24943 (17)	0.96857 (11)	0.0527 (4)
C12	0.23851 (11)	0.9052 (2)	0.56797 (11)	0.0560 (4)
H1	0.3877 (9)	0.8771 (18)	0.6223 (9)	0.045 (4)*
H3	0.1649 (12)	0.7387 (19)	0.6823 (11)	0.064 (5)*
H4	0.2211 (9)	0.5925 (19)	0.7907 (9)	0.050 (4)*
H7	0.2847 (10)	0.434 (2)	0.8706 (10)	0.055 (5)*
H8	0.3590 (10)	0.2688 (19)	0.9545 (11)	0.057 (5)*
H10	0.5560 (9)	0.4903 (17)	0.8720 (8)	0.041 (4)*
H11A	0.4975	0.2431	1.0226	0.079*	0.50
H11B	0.5689	0.2881	0.9685	0.079*	0.50
H11C	0.5150	0.1474	0.9446	0.079*	0.50
H11D	0.4887	0.1705	0.9986	0.079*	0.50
H11E	0.5459	0.3090	1.0125	0.079*	0.50
H11F	0.5566	0.1983	0.9373	0.079*	0.50
H12A	0.2140 (13)	0.826 (3)	0.5282 (14)	0.093 (7)*
H12B	0.1962 (13)	0.974 (3)	0.5817 (13)	0.087 (7)*
H12C	0.2796 (13)	0.967 (3)	0.5389 (13)	0.086 (6)*
H1O	0.514 (3)	0.125 (6)	0.712 (3)	0.106 (16)*	0.50

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.02194 (13)	0.02914 (14)	0.02690 (14)	0.000	0.00172 (8)	0.000
O1	0.135 (4)	0.0515 (13)	0.074 (2)	0.0214 (17)	0.026 (2)	0.0093 (15)
N1	0.0284 (5)	0.0368 (6)	0.0340 (6)	0.0012 (4)	0.0010 (4)	−0.0002 (4)
N2	0.0306 (6)	0.0345 (6)	0.0320 (5)	−0.0013 (4)	0.0014 (4)	−0.0006 (4)
N3	0.0409 (6)	0.0431 (7)	0.0414 (6)	−0.0021 (5)	0.0078 (5)	−0.0071 (5)
N4	0.0370 (6)	0.0434 (6)	0.0354 (6)	0.0076 (5)	−0.0039 (5)	−0.0028 (5)
N5	0.0394 (7)	0.0930 (12)	0.0621 (9)	0.0146 (7)	0.0087 (7)	−0.0108 (8)
C1	0.0353 (7)	0.0410 (7)	0.0364 (7)	0.0038 (6)	0.0008 (6)	0.0008 (6)
C2	0.0362 (7)	0.0451 (8)	0.0440 (8)	0.0079 (6)	−0.0047 (6)	−0.0027 (6)
C3	0.0291 (7)	0.0580 (10)	0.0548 (9)	0.0023 (6)	−0.0041 (6)	−0.0017 (7)
C4	0.0307 (7)	0.0520 (8)	0.0483 (8)	−0.0034 (6)	0.0019 (6)	0.0018 (7)
C5	0.0302 (6)	0.0368 (7)	0.0345 (6)	−0.0006 (5)	0.0017 (5)	−0.0041 (5)
C6	0.0297 (6)	0.0373 (7)	0.0323 (6)	−0.0021 (5)	0.0027 (5)	−0.0033 (5)
C7	0.0352 (7)	0.0524 (9)	0.0453 (8)	−0.0074 (6)	0.0037 (6)	0.0057 (7)
C8	0.0505 (9)	0.0481 (9)	0.0418 (8)	−0.0096 (7)	0.0055 (6)	0.0096 (7)
C9	0.0478 (8)	0.0387 (7)	0.0316 (7)	0.0000 (6)	−0.0007 (6)	0.0006 (6)
C10	0.0353 (7)	0.0390 (7)	0.0365 (7)	0.0003 (6)	−0.0009 (5)	0.0017 (6)
C11	0.0652 (11)	0.0488 (9)	0.0441 (9)	0.0043 (7)	−0.0062 (8)	0.0107 (7)
C12	0.0451 (9)	0.0679 (12)	0.0551 (10)	0.0106 (8)	−0.0099 (8)	0.0100 (9)

Geometric parameters (Å, º) top

O1—O1ⁱ	1.108 (8)	C5—C4	1.3943 (19)
O1—H1O	1.10 (5)	C2—C3	1.391 (2)
Co1—N1ⁱ	2.0907 (11)	C2—C12	1.509 (2)
Co1—N1	2.0907 (11)	C8—C9	1.383 (2)
Co1—N2ⁱ	2.0929 (10)	C8—H8	0.974 (18)
Co1—N2	2.0929 (10)	C10—C9	1.3903 (19)
Co1—N3	2.1095 (11)	C10—H10	1.016 (16)
Co1—N3ⁱ	2.1095 (12)	C9—C11	1.505 (2)
N2—C10	1.3379 (17)	C4—C3	1.384 (2)
N2—C6	1.3515 (16)	C4—H4	0.978 (16)
N1—C1	1.3454 (17)	C11—H11A	0.9600
N1—C5	1.3505 (17)	C11—H11B	0.9600
N4—N5	1.1604 (17)	C11—H11C	0.9600
N4—N3	1.1909 (16)	C11—H11D	0.9650
C1—C2	1.3898 (19)	C11—H11E	1.0271
C1—H1	0.990 (15)	C11—H11F	0.9703
C6—C7	1.3884 (19)	C12—H12B	0.96 (2)
C6—C5	1.4822 (18)	C12—H12C	1.01 (2)
C7—C8	1.380 (2)	C12—H12A	1.04 (2)
C7—H7	0.946 (17)	C3—H3	1.00 (2)

O1ⁱ—O1—H1O	58 (3)	C9—C8—H8	119.1 (10)
N1ⁱ—Co1—N1	175.95 (6)	N2—C10—C9	124.16 (13)
N1ⁱ—Co1—N2ⁱ	78.13 (4)	N2—C10—H10	115.8 (8)
N1—Co1—N2ⁱ	98.96 (4)	C9—C10—H10	120.0 (8)
N1ⁱ—Co1—N2	98.96 (4)	C8—C9—C10	116.33 (13)
N1—Co1—N2	78.13 (4)	C8—C9—C11	122.76 (14)
N2ⁱ—Co1—N2	89.76 (6)	C10—C9—C11	120.88 (14)
N1ⁱ—Co1—N3	92.09 (5)	C3—C4—C5	119.25 (14)
N1—Co1—N3	90.72 (5)	C3—C4—H4	120.1 (9)
N2ⁱ—Co1—N3	170.08 (4)	C5—C4—H4	120.6 (9)
N2—Co1—N3	90.12 (4)	C9—C11—H11A	109.5
N1ⁱ—Co1—N3ⁱ	90.72 (5)	C9—C11—H11B	109.5
N1—Co1—N3ⁱ	92.09 (5)	H11A—C11—H11B	109.5
N2ⁱ—Co1—N3ⁱ	90.12 (4)	C9—C11—H11C	109.5
N2—Co1—N3ⁱ	170.08 (4)	H11A—C11—H11C	109.5
N3—Co1—N3ⁱ	91.70 (7)	H11B—C11—H11C	109.5
C10—N2—C6	118.56 (11)	C9—C11—H11D	114.9
C10—N2—Co1	126.30 (9)	H11A—C11—H11D	46.2
C6—N2—Co1	115.13 (8)	H11B—C11—H11D	134.5
C1—N1—C5	119.08 (11)	H11C—C11—H11D	64.5
C1—N1—Co1	125.75 (9)	C9—C11—H11E	110.7
C5—N1—Co1	114.76 (9)	H11A—C11—H11E	61.3
N5—N4—N3	178.48 (15)	H11B—C11—H11E	50.7
N1—C1—C2	123.49 (13)	H11C—C11—H11E	139.4
N1—C1—H1	115.0 (9)	H11D—C11—H11E	102.5
C2—C1—H1	121.5 (9)	C9—C11—H11F	114.4
N2—C6—C7	120.89 (12)	H11A—C11—H11F	136.0
N2—C6—C5	115.11 (11)	H11B—C11—H11F	59.1
C7—C6—C5	123.89 (12)	H11C—C11—H11F	51.8
C8—C7—C6	119.32 (13)	H11D—C11—H11F	108.3
C8—C7—H7	121.3 (10)	H11E—C11—H11F	104.9
C6—C7—H7	119.2 (10)	C2—C12—H12B	112.6 (13)
N4—N3—Co1	123.67 (10)	C2—C12—H12C	112.9 (13)
N1—C5—C4	120.84 (12)	H12B—C12—H12C	108.6 (18)
N1—C5—C6	115.39 (11)	C2—C12—H12A	109.6 (13)
C4—C5—C6	123.71 (12)	H12B—C12—H12A	104.3 (18)
C1—C2—C3	116.83 (13)	H12C—C12—H12A	108.5 (17)
C1—C2—C12	120.81 (14)	C4—C3—C2	120.40 (14)
C3—C2—C12	122.36 (14)	C4—C3—H3	121.7 (10)
C7—C8—C9	120.64 (13)	C2—C3—H3	117.8 (10)
C7—C8—H8	120.2 (11)

N1ⁱ—Co1—N2—C10	−7.07 (11)	N1—Co1—N3—N4	32.12 (12)
N1—Co1—N2—C10	170.07 (11)	N2—Co1—N3—N4	−46.01 (12)
N2ⁱ—Co1—N2—C10	70.87 (10)	N3ⁱ—Co1—N3—N4	124.24 (13)
N3—Co1—N2—C10	−99.21 (11)	C1—N1—C5—C4	−2.10 (19)
N1ⁱ—Co1—N2—C6	174.06 (9)	Co1—N1—C5—C4	170.99 (11)
N1—Co1—N2—C6	−8.79 (9)	C1—N1—C5—C6	175.16 (11)
N2ⁱ—Co1—N2—C6	−108.00 (9)	Co1—N1—C5—C6	−11.75 (14)
N3—Co1—N2—C6	81.92 (9)	N2—C6—C5—N1	4.27 (16)
N2ⁱ—Co1—N1—C1	−88.45 (11)	C7—C6—C5—N1	−172.02 (13)
N2—Co1—N1—C1	−176.30 (11)	N2—C6—C5—C4	−178.57 (13)
N3—Co1—N1—C1	93.73 (11)	C7—C6—C5—C4	5.1 (2)
N3ⁱ—Co1—N1—C1	2.00 (11)	N1—C1—C2—C3	3.0 (2)
N2ⁱ—Co1—N1—C5	98.99 (9)	N1—C1—C2—C12	−176.10 (14)
N2—Co1—N1—C5	11.14 (9)	C6—C7—C8—C9	0.4 (2)
N3—Co1—N1—C5	−78.82 (9)	C6—N2—C10—C9	−0.1 (2)
N3ⁱ—Co1—N1—C5	−170.56 (9)	Co1—N2—C10—C9	−178.91 (10)
C5—N1—C1—C2	−0.7 (2)	C7—C8—C9—C10	2.1 (2)
Co1—N1—C1—C2	−172.92 (10)	C7—C8—C9—C11	−175.95 (15)
C10—N2—C6—C7	2.80 (19)	N2—C10—C9—C8	−2.3 (2)
Co1—N2—C6—C7	−178.24 (10)	N2—C10—C9—C11	175.74 (13)
C10—N2—C6—C5	−173.61 (11)	N1—C5—C4—C3	2.4 (2)
Co1—N2—C6—C5	5.35 (14)	C6—C5—C4—C3	−174.66 (13)
N2—C6—C7—C8	−3.0 (2)	C5—C4—C3—C2	0.1 (2)
C5—C6—C7—C8	173.09 (13)	C1—C2—C3—C4	−2.7 (2)
N1ⁱ—Co1—N3—N4	−144.98 (12)	C12—C2—C3—C4	176.44 (16)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N3ⁱⁱ	1.05 (5)	1.99 (5)	2.926 (3)	141 (4)
C3—H3···O1ⁱⁱⁱ	1.00 (2)	2.51 (2)	3.392 (4)	147.1 (14)
C1—H1···N3ⁱ	0.991 (15)	2.485 (15)	3.1241 (18)	121.9 (11)

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, y−1, −z+3/2; (iii) −x+1/2, y+1/2, z.

Experimental details

Crystal data
Chemical formula	[Co(C₁₂H₁₂N₂)₂(N₃)₂]·H₂O
M_r	529.46
Crystal system, space group	Orthorhombic, Pbcn
Temperature (K)	298
a, b, c (Å)	17.1030 (3), 8.5544 (2), 16.7062 (5)
V (Å³)	2444.22 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.74
Crystal size (mm)	0.30 × 0.25 × 0.06

Data collection
Diffractometer	Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.801, 0.957
No. of measured, independent and observed [I > 2σ(I)] reflections	13768, 2606, 2176
R_int	0.022
(sin θ/λ)_max (Å⁻¹)	0.633

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.024, 0.067, 1.03
No. of reflections	2606
No. of parameters	208
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.16, −0.25

Computer programs: , COLLECT (Nonius, 2002) and DENZO/SCALEPACK (Otwinowski & Minor, 1997), DENZO/SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected bond lengths (Å) top

Co1—N1	2.0907 (11)	Co1—N3	2.1095 (11)
Co1—N2	2.0929 (10)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···N3ⁱ	1.05 (5)	1.99 (5)	2.926 (3)	141 (4)
C3—H3···O1ⁱⁱ	1.00 (2)	2.51 (2)	3.392 (4)	147.1 (14)
C1—H1···N3ⁱⁱⁱ	0.991 (15)	2.485 (15)	3.1241 (18)	121.9 (11)

Symmetry codes: (i) −x+1, y−1, −z+3/2; (ii) −x+1/2, y+1/2, z; (iii) −x+1, y, −z+3/2.

Acknowledgements

The authors would like to thank Vongchavalitkul University for financial support [grant 2/52 (7)] and also gratefully acknowledge Rajamangala University of Technology Isan for support.

References

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