Bis[bis­(3,5-dimethyl-1H-pyrazol-1-yl)­borato]cobalt(II)

Hossaini Sadr, M.; Soltani, B.; Engle, J.T.; Ziegler, C.J.; Taheri, M.

doi:10.1107/S1600536811020976

metal-organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page m866

doi:10.1107/S1600536811020976

Open

access

Bis[bis(3,5-dimethyl-1H-pyrazol-1-yl)borato]cobalt(II)

Moayad Hossaini Sadr,^a ^* Behzad Soltani,^a James T. Engle,^b Christopher J. Ziegler ^b and M. Taheri ^a

^aDepartment of Chemistry, Azarbaijan University of Tarbiat Moallem, Tabriz, Iran, and ^bDepartment of Chemistry, University of Akron, Akron, OH, USA
^*Correspondence e-mail: sadr@azaruniv.edu

(Received 19 May 2011; accepted 31 May 2011; online 11 June 2011)

The asymmetric unit of the title compound, [Co(C₁₀H₁₆BN₄)₂], comprises one unit of the complex. The geometry around the Co^II ion is a distorted tetrahedron. The dihedral angles between the pyrazole rings in the two ligands are 47.19 (15) and 47.20 (16)°, while that between the coordination planes is 79.77 (7)°.

Related literature

For standard values of bond lengths, see: Allen et al. (1987 ). For background on pyrazolates and their complexes, see, for example; Trofimenko (1967 ); Trofimenko (1999 ); Trofimenko (2004 ); Sadr et al. (2008 ); Ruman et al. (2003 ); Krzystek et al. (2010 ).

Experimental

Crystal data

[Co(C₁₀H₁₆BN₄)₂]
M_r = 465.09
Monoclinic, P 2₁ /c
a = 8.351 (5) Å
b = 14.012 (9) Å
c = 19.833 (13) Å
β = 93.281 (7)°
V = 2317 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.77 mm⁻¹
T = 100 K
0.25 × 0.15 × 0.12 mm

Data collection

Bruker APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2005 ) T_min = 0.832, T_max = 0.914
18648 measured reflections
5048 independent reflections
3947 reflections with I > 2σ(I)
R_int = 0.046

Refinement

R[F² > 2σ(F²)] = 0.050
wR(F²) = 0.122
S = 1.04
5048 reflections
288 parameters
H-atom parameters constrained
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.61 e Å⁻³

Data collection: APEX2 (Bruker, 2005 ); cell refinement: SAINT (Bruker, 2005); 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 and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811020976/bg2405sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811020976/bg2405Isup2.hkl

checkCIF report

Comment top

During the last 40 years anionic polypyrazolylborate ligands (or Trofimeko's scorpionates) have proven to be popular and versatile ligands, binding to a wide variety of transition-metal ions (Trofimenko, 1967; Trofimenko, 1999; Trofimenko, 2004). In addition to variation of the coordinated metal ion or replacing H atoms bonded to a B centre by alkyl moieties, variation of type and number of substituents on the pyrazolyl rings allows for the synthesis of a large number of scorpionate complexes (Ruman et al., 2003; Krzystek et al., 2010). Cobalt complexes with bis pyrazolylborate ligands are of inherent interest in terms of understanding the electronic structure of Co^II as a function of coordination environment, even though, Co^II complexes themselves are of specific, biological interest as models for the active sites of many metalloproteins. In continuation of our work on the synthesis and structure of pyrazolate complexes (Sadr et al., 2008), we determined the crystal structure of the title compound, [Co(C₁₀ H₁₆ B N₄)₂] (1).

The asymmetric unit of (1) (Fig. 1), comprises one unit of the complex. The bond lengths and angles are within the normal ranges (Allen, et al., 1987). The geometry around Co^II is a distorted tetrahedron defined by N1, N4, N5, and N8 in the coordinated pyrazolate ligands. (Co-N, N-Co-N' ranges: 1.990 (2)-1.996 (2)Å and 97.03 (9)-137.03 (10)°, respectively ). The dihedral angle between the coordination planes (N1–Co1–N4 and N5–Co1–N8) is 79.77 (7)°, and the ones between the pyrazolate rings in each ligand are 47.19 (15) and 47.20 (16)°.

The structure does not present any kind of H-bonding interactions.

Related literature top

For standard values of bond lengths, see: Allen et al., (1987). For background on pyrazolate and their complexes see, for examples; Trofimenko (1967); Trofimenko (1999); Trofimenko (2004); Sadr et al. (2008); Ruman et al. (2003); Krzystek et al. (2010).

Experimental top

Tetrahydrofurane (25 ml) solution of potassium pyrazolborate (2 mmol, 0.48 g) was added into the stock water solution of Co(NO₃)₂,6H₂O (50 ml, 0.1 M). The reaction mixture was stirred for 3 h and the resulting product was extracted with CH₂Cl₂ (50 ml). The organic phase was washed twice with water (100 ml) and CH2Cl2 was removed on a rotary evaporator. The solid residue was dissolved in THF and left for crystallization from THF/n-Hexane (3/1) mixture at ambient temperature by slow evaporation. After 3 days, block purple crystals were collected. Single crystals suitable for X-ray diffraction analysis were obtained after 4 days.

Computing details top

Data collection: APEX2 (Bruker, 2005); cell refinement: SAINT (Bruker, 2005); data reduction: SAINT (Bruker, 2005); 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) and PLATON (Spek, 2009).

Figures top

Fig. 1. The ORTEP plot of the title compound, showing 40% probability displacement ellipsoids and the atomic numbering. The H atoms were omitted for clarity.

Bis[bis(3,5-dimethyl-1H-pyrazol-1-yl)borato]cobalt(II) top

Crystal data top

[Co(C₁₀H₁₆BN₄)₂]	F(000) = 980
M_r = 465.09	D_x = 1.333 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5094 reflections
a = 8.351 (5) Å	θ = 2.5–28.1°
b = 14.012 (9) Å	µ = 0.77 mm⁻¹
c = 19.833 (13) Å	T = 100 K
β = 93.281 (7)°	Block, purple
V = 2317 (3) Å³	0.25 × 0.15 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII CCD diffractometer	5048 independent reflections
Radiation source: fine-focus sealed tube	3947 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.046
ϕ and ω scans	θ_max = 27.0°, θ_min = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	h = −10→10
T_min = 0.832, T_max = 0.914	k = −17→17
18648 measured reflections	l = −25→24

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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0516P)² + 2.3676P] where P = (F_o² + 2F_c²)/3
5048 reflections	(Δ/σ)_max < 0.001
288 parameters	Δρ_max = 0.60 e Å⁻³
0 restraints	Δρ_min = −0.61 e Å⁻³

Crystal data top

[Co(C₁₀H₁₆BN₄)₂]	V = 2317 (3) Å³
M_r = 465.09	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 8.351 (5) Å	µ = 0.77 mm⁻¹
b = 14.012 (9) Å	T = 100 K
c = 19.833 (13) Å	0.25 × 0.15 × 0.12 mm
β = 93.281 (7)°

Data collection top

Bruker APEXII CCD diffractometer	5048 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2008)	3947 reflections with I > 2σ(I)
T_min = 0.832, T_max = 0.914	R_int = 0.046
18648 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	0 restraints
wR(F²) = 0.122	H-atom parameters constrained
S = 1.04	Δρ_max = 0.60 e Å⁻³
5048 reflections	Δρ_min = −0.61 e Å⁻³
288 parameters

Special details top

Experimental. 'Ratio of minimum to maximum apparent transmission: 0.1661'

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	0.10933 (4)	0.19693 (2)	0.197855 (17)	0.01815 (12)
N1	0.1543 (3)	0.15049 (15)	0.34192 (11)	0.0192 (5)
N2	0.0445 (3)	0.15101 (15)	0.28722 (11)	0.0193 (5)
N3	0.3688 (2)	0.25721 (15)	0.29484 (10)	0.0172 (5)
N4	0.2967 (3)	0.27492 (16)	0.23208 (11)	0.0192 (5)
N5	−0.0682 (3)	0.28065 (15)	0.16145 (11)	0.0194 (5)
N6	−0.1491 (3)	0.25825 (16)	0.10128 (11)	0.0196 (5)
N7	0.0520 (3)	0.14005 (16)	0.05685 (11)	0.0211 (5)
N8	0.1649 (3)	0.13899 (16)	0.11056 (11)	0.0201 (5)
C1	0.1616 (4)	0.1256 (2)	0.46705 (14)	0.0293 (7)
H1A	0.2306	0.0690	0.4695	0.044*
H1B	0.0816	0.1208	0.5012	0.044*
H1C	0.2270	0.1829	0.4755	0.044*
C2	0.0784 (3)	0.13186 (19)	0.39839 (14)	0.0219 (6)
C3	−0.0833 (3)	0.1208 (2)	0.38042 (14)	0.0242 (6)
H3	−0.1662	0.1071	0.4098	0.029*
C4	−0.1002 (3)	0.13375 (19)	0.31117 (14)	0.0228 (6)
C5	−0.2482 (3)	0.1303 (2)	0.26574 (15)	0.0274 (6)
H5A	−0.2726	0.1944	0.2483	0.041*
H5B	−0.3379	0.1072	0.2910	0.041*
H5C	−0.2315	0.0870	0.2280	0.041*
C6	0.5782 (3)	0.3276 (2)	0.37451 (14)	0.0246 (6)
H6A	0.5128	0.3126	0.4126	0.037*
H6B	0.6262	0.3910	0.3811	0.037*
H6C	0.6634	0.2798	0.3718	0.037*
C7	0.4748 (3)	0.32668 (18)	0.31042 (13)	0.0191 (5)
C8	0.4721 (3)	0.39084 (19)	0.25731 (13)	0.0206 (6)
H8	0.5346	0.4471	0.2543	0.025*
C9	0.3593 (3)	0.35616 (18)	0.20939 (13)	0.0195 (5)
C10	0.3077 (3)	0.3951 (2)	0.14138 (14)	0.0251 (6)
H10A	0.3101	0.3441	0.1077	0.038*
H10B	0.3808	0.4464	0.1295	0.038*
H10C	0.1985	0.4204	0.1424	0.038*
C11	−0.0646 (3)	0.4077 (2)	0.24764 (14)	0.0261 (6)
H11A	−0.0821	0.3625	0.2842	0.039*
H11B	−0.1234	0.4669	0.2554	0.039*
H11C	0.0502	0.4217	0.2465	0.039*
C12	−0.1234 (3)	0.36511 (18)	0.18175 (13)	0.0204 (6)
C13	−0.2387 (3)	0.39813 (19)	0.13439 (13)	0.0210 (6)
H13	−0.2965	0.4564	0.1357	0.025*
C14	−0.2524 (3)	0.32872 (19)	0.08469 (13)	0.0201 (5)
C15	−0.3648 (3)	0.3250 (2)	0.02312 (14)	0.0260 (6)
H15A	−0.3068	0.3027	−0.0155	0.039*
H15B	−0.4081	0.3889	0.0135	0.039*
H15C	−0.4529	0.2810	0.0310	0.039*
C16	0.0339 (4)	0.1101 (2)	−0.06737 (14)	0.0282 (6)
H16A	−0.0476	0.0599	−0.0666	0.042*
H16B	0.1094	0.0952	−0.1019	0.042*
H16C	−0.0181	0.1715	−0.0779	0.042*
C17	0.1225 (3)	0.11597 (19)	0.00018 (14)	0.0225 (6)
C18	0.2834 (3)	0.09960 (19)	0.01625 (14)	0.0248 (6)
H18	0.3625	0.0813	−0.0138	0.030*
C19	0.3061 (3)	0.11533 (19)	0.08547 (14)	0.0221 (6)
C20	0.4570 (3)	0.1113 (2)	0.12963 (15)	0.0282 (6)
H20A	0.5029	0.1755	0.1342	0.042*
H20B	0.5340	0.0688	0.1093	0.042*
H20C	0.4329	0.0871	0.1743	0.042*
B1	0.3357 (3)	0.1598 (2)	0.32884 (16)	0.0201 (6)
H1D	0.3987	0.1553	0.3713	0.024*
H1E	0.3674	0.1081	0.2999	0.024*
B2	−0.1278 (4)	0.1565 (2)	0.07122 (17)	0.0237 (7)
H2A	−0.1621	0.1089	0.1028	0.028*
H2B	−0.1937	0.1503	0.0296	0.028*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Co1	0.01670 (19)	0.01856 (19)	0.01875 (19)	−0.00036 (14)	−0.00268 (13)	−0.00079 (15)
N1	0.0196 (12)	0.0180 (11)	0.0196 (11)	0.0006 (9)	−0.0028 (9)	−0.0001 (9)
N2	0.0178 (11)	0.0188 (11)	0.0208 (11)	−0.0011 (9)	−0.0026 (9)	−0.0018 (9)
N3	0.0166 (11)	0.0174 (11)	0.0171 (11)	−0.0004 (8)	−0.0039 (9)	0.0019 (8)
N4	0.0178 (11)	0.0210 (11)	0.0183 (11)	−0.0002 (9)	−0.0035 (9)	0.0024 (9)
N5	0.0185 (11)	0.0190 (11)	0.0200 (11)	−0.0002 (9)	−0.0052 (9)	−0.0024 (9)
N6	0.0178 (12)	0.0201 (11)	0.0201 (11)	0.0012 (9)	−0.0040 (9)	−0.0023 (9)
N7	0.0217 (12)	0.0207 (12)	0.0203 (12)	0.0013 (9)	−0.0026 (9)	−0.0016 (9)
N8	0.0189 (11)	0.0208 (12)	0.0203 (11)	0.0003 (9)	−0.0026 (9)	−0.0009 (9)
C1	0.0339 (17)	0.0305 (16)	0.0232 (15)	−0.0030 (13)	−0.0002 (12)	0.0009 (12)
C2	0.0250 (14)	0.0173 (13)	0.0236 (14)	−0.0013 (11)	0.0034 (11)	−0.0012 (11)
C3	0.0229 (14)	0.0239 (14)	0.0265 (15)	−0.0034 (11)	0.0063 (11)	−0.0025 (12)
C4	0.0205 (14)	0.0184 (13)	0.0296 (15)	−0.0008 (11)	0.0030 (11)	−0.0027 (11)
C5	0.0161 (14)	0.0346 (16)	0.0315 (16)	−0.0024 (12)	0.0001 (11)	−0.0056 (13)
C6	0.0260 (15)	0.0248 (15)	0.0223 (14)	−0.0041 (11)	−0.0053 (11)	−0.0017 (11)
C7	0.0171 (13)	0.0185 (13)	0.0213 (13)	0.0010 (10)	−0.0016 (10)	−0.0013 (10)
C8	0.0209 (14)	0.0179 (13)	0.0229 (14)	−0.0027 (10)	0.0007 (11)	0.0008 (11)
C9	0.0196 (13)	0.0185 (13)	0.0205 (13)	0.0022 (10)	0.0019 (10)	0.0018 (10)
C10	0.0267 (15)	0.0263 (15)	0.0222 (14)	−0.0008 (11)	−0.0004 (11)	0.0046 (11)
C11	0.0287 (16)	0.0251 (15)	0.0241 (15)	−0.0003 (12)	−0.0012 (12)	−0.0043 (11)
C12	0.0208 (14)	0.0174 (13)	0.0230 (14)	−0.0015 (10)	0.0024 (11)	−0.0003 (10)
C13	0.0206 (14)	0.0195 (13)	0.0231 (14)	0.0029 (10)	0.0019 (11)	0.0022 (11)
C14	0.0186 (13)	0.0230 (14)	0.0187 (13)	0.0005 (10)	0.0020 (10)	0.0016 (10)
C15	0.0254 (15)	0.0299 (16)	0.0223 (14)	0.0035 (12)	−0.0038 (11)	−0.0006 (12)
C16	0.0355 (17)	0.0268 (15)	0.0218 (15)	0.0062 (13)	−0.0035 (12)	−0.0017 (12)
C17	0.0278 (15)	0.0172 (13)	0.0224 (14)	0.0013 (11)	0.0009 (11)	−0.0008 (11)
C18	0.0269 (15)	0.0218 (14)	0.0261 (15)	0.0035 (11)	0.0056 (11)	0.0017 (11)
C19	0.0212 (14)	0.0187 (13)	0.0265 (15)	0.0025 (10)	0.0028 (11)	0.0028 (11)
C20	0.0207 (15)	0.0330 (16)	0.0308 (16)	0.0017 (12)	−0.0001 (12)	0.0024 (13)
B1	0.0171 (15)	0.0193 (15)	0.0233 (15)	−0.0001 (11)	−0.0021 (11)	0.0039 (12)
B2	0.0194 (16)	0.0215 (15)	0.0296 (17)	−0.0016 (12)	−0.0029 (12)	−0.0053 (13)

Geometric parameters (Å, º) top

Co1—N2	1.990 (2)	C6—H6C	0.9800
Co1—N8	1.991 (2)	C7—C8	1.384 (4)
Co1—N5	1.993 (2)	C8—C9	1.387 (4)
Co1—N4	1.996 (2)	C8—H8	0.9500
N1—C2	1.344 (3)	C9—C10	1.495 (4)
N1—N2	1.380 (3)	C10—H10A	0.9800
N1—B1	1.557 (4)	C10—H10B	0.9800
N2—C4	1.345 (3)	C10—H10C	0.9800
N3—C7	1.340 (3)	C11—C12	1.494 (4)
N3—N4	1.374 (3)	C11—H11A	0.9800
N3—B1	1.554 (4)	C11—H11B	0.9800
N4—C9	1.341 (3)	C11—H11C	0.9800
N5—C12	1.340 (3)	C12—C13	1.385 (4)
N5—N6	1.374 (3)	C13—C14	1.385 (4)
N6—C14	1.340 (3)	C13—H13	0.9500
N6—B2	1.560 (4)	C14—C15	1.498 (4)
N7—C17	1.341 (3)	C15—H15A	0.9800
N7—N8	1.381 (3)	C15—H15B	0.9800
N7—B2	1.561 (4)	C15—H15C	0.9800
N8—C19	1.347 (3)	C16—C17	1.495 (4)
C1—C2	1.496 (4)	C16—H16A	0.9800
C1—H1A	0.9800	C16—H16B	0.9800
C1—H1B	0.9800	C16—H16C	0.9800
C1—H1C	0.9800	C17—C18	1.382 (4)
C2—C3	1.385 (4)	C18—C19	1.393 (4)
C3—C4	1.385 (4)	C18—H18	0.9500
C3—H3	0.9500	C19—C20	1.494 (4)
C4—C5	1.488 (4)	C20—H20A	0.9800
C5—H5A	0.9800	C20—H20B	0.9800
C5—H5B	0.9800	C20—H20C	0.9800
C5—H5C	0.9800	B1—H1D	0.9691
C6—C7	1.495 (4)	B1—H1E	0.9704
C6—H6A	0.9800	B2—H2A	0.9695
C6—H6B	0.9800	B2—H2B	0.9693

N2—Co1—N8	137.03 (10)	N4—C9—C8	109.3 (2)
N2—Co1—N5	106.14 (10)	N4—C9—C10	121.0 (2)
N8—Co1—N5	97.50 (10)	C8—C9—C10	129.8 (2)
N2—Co1—N4	97.03 (9)	C9—C10—H10A	109.5
N8—Co1—N4	107.57 (10)	C9—C10—H10B	109.5
N5—Co1—N4	110.71 (10)	H10A—C10—H10B	109.5
C2—N1—N2	109.4 (2)	C9—C10—H10C	109.5
C2—N1—B1	131.7 (2)	H10A—C10—H10C	109.5
N2—N1—B1	118.5 (2)	H10B—C10—H10C	109.5
C4—N2—N1	106.9 (2)	C12—C11—H11A	109.5
C4—N2—Co1	131.96 (19)	C12—C11—H11B	109.5
N1—N2—Co1	119.96 (17)	H11A—C11—H11B	109.5
C7—N3—N4	109.1 (2)	C12—C11—H11C	109.5
C7—N3—B1	132.0 (2)	H11A—C11—H11C	109.5
N4—N3—B1	118.2 (2)	H11B—C11—H11C	109.5
C9—N4—N3	107.4 (2)	N5—C12—C13	109.2 (2)
C9—N4—Co1	131.58 (18)	N5—C12—C11	120.9 (2)
N3—N4—Co1	120.24 (16)	C13—C12—C11	129.8 (2)
C12—N5—N6	107.6 (2)	C14—C13—C12	105.9 (2)
C12—N5—Co1	132.25 (18)	C14—C13—H13	127.0
N6—N5—Co1	119.92 (16)	C12—C13—H13	127.0
C14—N6—N5	108.8 (2)	N6—C14—C13	108.5 (2)
C14—N6—B2	131.8 (2)	N6—C14—C15	122.6 (2)
N5—N6—B2	118.7 (2)	C13—C14—C15	128.8 (2)
C17—N7—N8	109.3 (2)	C14—C15—H15A	109.5
C17—N7—B2	131.5 (2)	C14—C15—H15B	109.5
N8—N7—B2	118.8 (2)	H15A—C15—H15B	109.5
C19—N8—N7	106.9 (2)	C14—C15—H15C	109.5
C19—N8—Co1	132.37 (19)	H15A—C15—H15C	109.5
N7—N8—Co1	118.93 (17)	H15B—C15—H15C	109.5
C2—C1—H1A	109.5	C17—C16—H16A	109.5
C2—C1—H1B	109.5	C17—C16—H16B	109.5
H1A—C1—H1B	109.5	H16A—C16—H16B	109.5
C2—C1—H1C	109.5	C17—C16—H16C	109.5
H1A—C1—H1C	109.5	H16A—C16—H16C	109.5
H1B—C1—H1C	109.5	H16B—C16—H16C	109.5
N1—C2—C3	107.9 (2)	N7—C17—C18	108.4 (2)
N1—C2—C1	123.6 (3)	N7—C17—C16	123.1 (3)
C3—C2—C1	128.5 (3)	C18—C17—C16	128.5 (3)
C4—C3—C2	106.5 (2)	C17—C18—C19	106.0 (2)
C4—C3—H3	126.8	C17—C18—H18	127.0
C2—C3—H3	126.8	C19—C18—H18	127.0
N2—C4—C3	109.3 (2)	N8—C19—C18	109.3 (2)
N2—C4—C5	121.6 (3)	N8—C19—C20	121.3 (2)
C3—C4—C5	129.1 (3)	C18—C19—C20	129.4 (3)
C4—C5—H5A	109.5	C19—C20—H20A	109.5
C4—C5—H5B	109.5	C19—C20—H20B	109.5
H5A—C5—H5B	109.5	H20A—C20—H20B	109.5
C4—C5—H5C	109.5	C19—C20—H20C	109.5
H5A—C5—H5C	109.5	H20A—C20—H20C	109.5
H5B—C5—H5C	109.5	H20B—C20—H20C	109.5
C7—C6—H6A	109.5	N3—B1—N1	110.2 (2)
C7—C6—H6B	109.5	N3—B1—H1D	109.4
H6A—C6—H6B	109.5	N1—B1—H1D	109.6
C7—C6—H6C	109.5	N3—B1—H1E	109.7
H6A—C6—H6C	109.5	N1—B1—H1E	109.7
H6B—C6—H6C	109.5	H1D—B1—H1E	108.2
N3—C7—C8	108.3 (2)	N6—B2—N7	109.7 (2)
N3—C7—C6	123.0 (2)	N6—B2—H2A	109.7
C8—C7—C6	128.7 (2)	N7—B2—H2A	109.8
C7—C8—C9	106.0 (2)	N6—B2—H2B	109.6
C7—C8—H8	127.0	N7—B2—H2B	109.7
C9—C8—H8	127.0	H2A—B2—H2B	108.3

C2—N1—N2—C4	0.8 (3)	N1—N2—C4—C5	179.3 (2)
B1—N1—N2—C4	174.7 (2)	Co1—N2—C4—C5	11.9 (4)
C2—N1—N2—Co1	170.05 (17)	C2—C3—C4—N2	0.6 (3)
B1—N1—N2—Co1	−16.1 (3)	C2—C3—C4—C5	−179.6 (3)
N8—Co1—N2—C4	−90.4 (3)	N4—N3—C7—C8	0.1 (3)
N5—Co1—N2—C4	30.3 (3)	B1—N3—C7—C8	170.1 (3)
N4—Co1—N2—C4	144.3 (2)	N4—N3—C7—C6	−178.0 (2)
N8—Co1—N2—N1	103.6 (2)	B1—N3—C7—C6	−8.0 (4)
N5—Co1—N2—N1	−135.75 (18)	N3—C7—C8—C9	0.0 (3)
N4—Co1—N2—N1	−21.76 (19)	C6—C7—C8—C9	178.0 (3)
C7—N3—N4—C9	−0.2 (3)	N3—N4—C9—C8	0.2 (3)
B1—N3—N4—C9	−171.7 (2)	Co1—N4—C9—C8	169.59 (19)
C7—N3—N4—Co1	−171.03 (17)	N3—N4—C9—C10	179.1 (2)
B1—N3—N4—Co1	17.4 (3)	Co1—N4—C9—C10	−11.5 (4)
N2—Co1—N4—C9	−147.1 (2)	C7—C8—C9—N4	−0.1 (3)
N8—Co1—N4—C9	68.6 (3)	C7—C8—C9—C10	−178.9 (3)
N5—Co1—N4—C9	−36.9 (3)	N6—N5—C12—C13	−0.7 (3)
N2—Co1—N4—N3	21.2 (2)	Co1—N5—C12—C13	173.49 (19)
N8—Co1—N4—N3	−123.16 (19)	N6—N5—C12—C11	177.2 (2)
N5—Co1—N4—N3	131.42 (18)	Co1—N5—C12—C11	−8.6 (4)
N2—Co1—N5—C12	66.4 (3)	N5—C12—C13—C14	0.8 (3)
N8—Co1—N5—C12	−149.9 (2)	C11—C12—C13—C14	−176.8 (3)
N4—Co1—N5—C12	−37.8 (3)	N5—N6—C14—C13	0.2 (3)
N2—Co1—N5—N6	−119.98 (19)	B2—N6—C14—C13	169.9 (3)
N8—Co1—N5—N6	23.8 (2)	N5—N6—C14—C15	−177.4 (2)
N4—Co1—N5—N6	135.80 (18)	B2—N6—C14—C15	−7.7 (4)
C12—N5—N6—C14	0.3 (3)	C12—C13—C14—N6	−0.6 (3)
Co1—N5—N6—C14	−174.73 (17)	C12—C13—C14—C15	176.8 (3)
C12—N5—N6—B2	−170.9 (2)	N8—N7—C17—C18	−0.5 (3)
Co1—N5—N6—B2	14.0 (3)	B2—N7—C17—C18	−173.1 (3)
C17—N7—N8—C19	1.0 (3)	N8—N7—C17—C16	180.0 (2)
B2—N7—N8—C19	174.6 (2)	B2—N7—C17—C16	7.4 (5)
C17—N7—N8—Co1	167.53 (18)	N7—C17—C18—C19	−0.1 (3)
B2—N7—N8—Co1	−18.8 (3)	C16—C17—C18—C19	179.4 (3)
N2—Co1—N8—C19	−95.1 (3)	N7—N8—C19—C18	−1.1 (3)
N5—Co1—N8—C19	141.3 (2)	Co1—N8—C19—C18	−165.08 (19)
N4—Co1—N8—C19	26.8 (3)	N7—N8—C19—C20	177.5 (2)
N2—Co1—N8—N7	102.4 (2)	Co1—N8—C19—C20	13.5 (4)
N5—Co1—N8—N7	−21.16 (19)	C17—C18—C19—N8	0.8 (3)
N4—Co1—N8—N7	−135.73 (18)	C17—C18—C19—C20	−177.6 (3)
N2—N1—C2—C3	−0.5 (3)	C7—N3—B1—N1	127.9 (3)
B1—N1—C2—C3	−173.3 (3)	N4—N3—B1—N1	−62.9 (3)
N2—N1—C2—C1	179.7 (2)	C2—N1—B1—N3	−125.5 (3)
B1—N1—C2—C1	7.0 (4)	N2—N1—B1—N3	62.3 (3)
N1—C2—C3—C4	−0.1 (3)	C14—N6—B2—N7	130.1 (3)
C1—C2—C3—C4	179.7 (3)	N5—N6—B2—N7	−61.1 (3)
N1—N2—C4—C3	−0.9 (3)	C17—N7—B2—N6	−123.8 (3)
Co1—N2—C4—C3	−168.27 (19)	N8—N7—B2—N6	64.2 (3)

Experimental details

Crystal data
Chemical formula	[Co(C₁₀H₁₆BN₄)₂]
M_r	465.09
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	8.351 (5), 14.012 (9), 19.833 (13)
β (°)	93.281 (7)
V (Å³)	2317 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.77
Crystal size (mm)	0.25 × 0.15 × 0.12

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2008)
T_min, T_max	0.832, 0.914
No. of measured, independent and observed [I > 2σ(I)] reflections	18648, 5048, 3947
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.639

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.122, 1.04
No. of reflections	5048
No. of parameters	288
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.61

Computer programs: APEX2 (Bruker, 2005), SAINT (Bruker, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Acknowledgements

This research has been supported by a research fund (No. 403/313) from Azarbaijan University of Tarbiat Moallem (MHS and BS). CJZ and JTE thank the University of Akron for providing the X-ray facility.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Bruker (2005). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Krzystek, J., Swenson, D. C., Zvyagin, S. A., Smirnov, D., Ozarowski, A. & Telser, J. (2010). J. Am. Chem. Soc. 132, 5241–5253. Web of Science CrossRef CAS PubMed Google Scholar
Ruman, T., Ciunik, Z. & Wolowiec, S. (2003). Polyhedron, 22, 581–586. CrossRef CAS Google Scholar
Sadr, M. H., Niaz, S. A., Gorbani, S., Gao, S. & Ng, S. W. (2008). Acta Cryst. E64, m158. Web of Science CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Trofimenko, S. (1967). J. Am. Chem. Soc. 89, 6288–6294. CrossRef CAS Web of Science Google Scholar
Trofimenko, S. (1999). Scorpionates: The Coordination Chemistry of Polypyrazolylborate Ligands, pp. 292–292. London: Imperial College Press. Google Scholar
Trofimenko, S. (2004). Polyhedron, 23, 197–203. Web of Science CrossRef CAS Google Scholar