Mono-BBN (9-borabi­cyclo­[3.3.1]­nonane) adduct of bis­(diethyl­glyoximato)­nickel(II)

Krivokapić, A.; Faiz, J.A.; Anderson, H.L.

doi:10.1107/S160053680301729X

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Mono-BBN (9-borabicyclo[3.3.1]nonane) adduct of bis(diethylglyoximato)nickel(II)

A. Krivokapić, J. A. Faiz and H. L. Anderson

The mono-BBN adduct of bis(diethylglyoximato)nickel(II), [7-(cyclooctane-1,5-diyl)-2,3,11,12-tetraethyl-6,8-dioxa-5,9-diaza-7-boratridecane-1,13-dicarbaldehyde dioximato-κ⁴N]nickel(II), [Ni(C₂₀H₃₅BN₄O₄)], crystallizes with two molecules in the asymmetric unit and with a short Ni

Ni distance [3.5042 (3) Å].

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301729X/ci6243sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S160053680301729X/ci6243Isup2.hkl Contains datablock I

CCDC reference: 222806

checkCIF report

Key indicators

Single-crystal X-ray study
T = 150 K
Mean (C-C) = 0.003 Å
R factor = 0.030
wR factor = 0.038
Data-to-parameter ratio = 13.7

checkCIF/PLATON results

No syntax errors found



Alert level A
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .....       0.97

Alert level C
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) .       3.01 Ratio
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni1    -   N1     =       5.34 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni2    -   N6     =       6.48 su
PLAT232_ALERT_2_C Hirshfeld Test Diff (M-X)  Ni2    -   N8     =       6.01 su
PLAT410_ALERT_2_C Short Intra H...H Contact:H151    .. H192    =       1.91 Ang.
PLAT410_ALERT_2_C Short Intra H...H Contact:H352    .. H391    =       1.91 Ang.

   1 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   6 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

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

Comment top

Square-planar metal bis-glyoxime complexes have long attracted interest because of their ability to bind axial ligands (Chakavorty, 1974; Stephens & Vagg, 1980). We are interested in exploring the scope of these units for supramolecular self-assembly. These complexes can often be stabilized and solubilized by boronylation (Schrauzer, 1962; Bakac et al., 1986). We present here the synthesis and crystal structure of a bis(diethylglyoximato)nickel(II) complex, with one 9-borabicyclo[3.3.1]nonane (BBN) unit chelated to the O atoms, (I). To the best of our knowledge, BBN adducts of nickel glyoxime complexes have not been reported previously, although some related iron(II) complexes are known (Harshani de Silva et al., 1995). Compound (I) was prepared in good yield by treating bis(diethylglyoximato)nickel(II) with methoxy-BBN in toluene.

The geometry of (I) is similar to those of previously reported complexes of this type (Chakavorty, 1974) (Fig. 1 and Table 1). It is interesting that the mono-BBN adduct (I) exists as a dimer in the solid state, with a short Ni···Ni distance of 3.5042 (3) Å (Fig. 1). The asymmetric unit contains a dimer and the geometry of the 9BBN unit leads to short contacts between H151···H192 (1.91 Å) and H352···H391 (1.91 Å).

Experimental top

Methoxy-9-BBN (0.61 ml, 1.0 M in hexanes; 0.61 mmol) was added to a solution of bis(diethylglyoximato)nickel(II) (0.10 g, 0.29 mmol) in toluene (5 ml). After heating to reflux for 2 h, the product was chromatographed (SiO₂, 5:1 hexane/ethyl acetate) to yield (I) (0.105 g, 78%) as red crystals. M.p.: 464–466 K; δ_H (400 MHz, CDCl₃): 17.77 (1H, s), 2.64 (4H, q), 2.58 (4H, q), 1.84–1.76 (2H, m), 1.71–1.62 (10H, m), 1.78–1.43 (2H, m), 1.23 (6H, t), 1.18 (6H, t); δ_C (100 MHz, CDCl₃): 161.7, 155.7, 31.6, 24.8, 19.3, 19.0, 10.3, 9.9; m/z (APCI⁺) 465.18 [M+H]⁺. Crystals of (I) were grown from acetone by evaporation.

Computing details top

Data collection: COLLECT (Nonius, 1997-2001); cell refinement: DENZO/SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO/SCALEPACK; program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: CRYSTALS (Watkin et al., 2001); molecular graphics: CAMERON (Watkin et al., 1996); software used to prepare material for publication: CRYSTALS.

Figures top

Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level for non-H atoms.

[7-(cyclooctane-1,5-diyl)-2,3,11,12-tetraethyl-6,8-dioxa-5,9-diaza-7- boratridecane-1,13-dicarbaldehyde dioximato-κ⁴N]nickel(II) top

Crystal data top

[Ni(C₂₀H₃₅BN₄O₄)]	Z = 4
M_r = 465.04	F(000) = 992.000
Triclinic, P1	D_x = 1.373 Mg m⁻³
Hall symbol: -P 1	Melting point: 464-466 K K
a = 11.5210 (2) Å	Mo Kα radiation, λ = 0.71073 Å
b = 14.8794 (2) Å	Cell parameters from 8108 reflections
c = 14.9455 (3) Å	θ = 4–27°
α = 79.4462 (6)°	µ = 0.90 mm⁻¹
β = 70.0605 (7)°	T = 150 K
γ = 69.4812 (11)°	Plate, red
V = 2249.76 (7) Å³	0.30 × 0.20 × 0.19 mm

Data collection top

Enraf-Nonius KappaCCD diffractometer	7437 reflections with I > 3σ(I)
Graphite monochromator	R_int = 0.01
ω scans	θ_max = 27.4°, θ_min = 4.1°
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	h = −14→14
T_min = 0.84, T_max = 0.84	k = −19→19
16886 measured reflections	l = −19→19
9767 independent reflections

Refinement top

Refinement on F	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.030	H-atom parameters not refined
wR(F²) = 0.038	Method = Prince modified Chebychev polynomial, (Watkin, 1994) W = [weight][1-(δF/6σF)²]², with 0.901, 0.532 and 0.614
S = 1.04	(Δ/σ)_max < 0.001
7437 reflections	Δρ_max = 0.30 e Å⁻³
541 parameters	Δρ_min = −0.35 e Å⁻³

Crystal data top

[Ni(C₂₀H₃₅BN₄O₄)]	γ = 69.4812 (11)°
M_r = 465.04	V = 2249.76 (7) Å³
Triclinic, P1	Z = 4
a = 11.5210 (2) Å	Mo Kα radiation
b = 14.8794 (2) Å	µ = 0.90 mm⁻¹
c = 14.9455 (3) Å	T = 150 K
α = 79.4462 (6)°	0.30 × 0.20 × 0.19 mm
β = 70.0605 (7)°

Data collection top

Enraf-Nonius KappaCCD diffractometer	9767 independent reflections
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)	7437 reflections with I > 3σ(I)
T_min = 0.84, T_max = 0.84	R_int = 0.01
16886 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	541 parameters
wR(F²) = 0.038	H-atom parameters not refined
S = 1.04	Δρ_max = 0.30 e Å⁻³
7437 reflections	Δρ_min = −0.35 e Å⁻³

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Ni2	0.82768 (2)	0.154400 (15)	0.186240 (14)	0.0168
Ni1	0.62744 (2)	0.290778 (15)	0.381870 (15)	0.0181
O2	0.69532 (12)	0.42516 (9)	0.22749 (8)	0.0232
O6	0.62957 (12)	0.16389 (9)	0.10866 (8)	0.0208
O1	0.83346 (12)	0.37323 (9)	0.33423 (9)	0.0230
O7	0.88510 (13)	0.0484 (1)	0.35124 (9)	0.0264
O5	0.77390 (12)	0.26067 (8)	0.01671 (8)	0.0211
O8	1.01845 (13)	0.1527 (1)	0.26685 (9)	0.0270
O4	0.55745 (13)	0.1590 (1)	0.53723 (9)	0.0282
N7	0.80814 (14)	0.0711 (1)	0.2959 (1)	0.0202
N2	0.61485 (14)	0.3716 (1)	0.2724 (1)	0.0208
N5	0.84553 (14)	0.2391 (1)	0.0776 (1)	0.0195
O3	0.42657 (14)	0.2069 (1)	0.4280 (1)	0.0321
N1	0.77108 (14)	0.3124 (1)	0.3942 (1)	0.0205
N4	0.64320 (15)	0.2065 (1)	0.4887 (1)	0.0221
N3	0.48927 (15)	0.26433 (11)	0.36647 (11)	0.0230
N6	0.68868 (14)	0.1242 (1)	0.1777 (1)	0.0181
N8	0.96283 (14)	0.1891 (1)	0.1971 (1)	0.0212
C21	0.64047 (17)	0.06820 (12)	0.24642 (12)	0.0212
C2	0.45210 (18)	0.30743 (13)	0.29240 (13)	0.0252
C16	0.52409 (18)	0.59805 (13)	0.33978 (14)	0.0274
C14	0.7175 (2)	0.62121 (14)	0.19610 (14)	0.0316
C37	0.84283 (17)	0.08253 (12)	−0.02190 (12)	0.0227
C24	0.93123 (17)	0.28217 (12)	0.06129 (13)	0.0220
C33	0.64866 (17)	0.21324 (12)	−0.06560 (13)	0.0231
C34	0.74256 (19)	0.23540 (14)	−0.16253 (13)	0.0295
C40	0.5900 (2)	0.13490 (14)	−0.06669 (15)	0.0315
C38	0.7859 (2)	0.00399 (13)	−0.02518 (14)	0.0302
C27	0.68475 (19)	−0.03326 (14)	0.40220 (13)	0.0275
C15	0.5854 (2)	0.66885 (14)	0.26780 (16)	0.0342
C5	0.5189 (2)	0.41819 (15)	0.13969 (13)	0.0305
C23	0.99886 (17)	0.25473 (12)	0.13432 (13)	0.0229
C32	0.8619 (2)	0.44817 (15)	−0.02188 (16)	0.0386
C1	0.53149 (17)	0.36840 (12)	0.23382 (12)	0.0225
C25	0.5245 (2)	0.04020 (16)	0.25434 (15)	0.0328
C17	0.61955 (16)	0.51620 (12)	0.38224 (12)	0.0208
C36	0.93601 (19)	0.10578 (14)	−0.11795 (13)	0.0294
C4	0.82135 (18)	0.25716 (13)	0.45814 (13)	0.0231
C3	0.74068 (18)	0.19660 (13)	0.51774 (12)	0.0242
C35	0.8708 (2)	0.15339 (16)	−0.19585 (13)	0.0343
C28	0.7894 (2)	−0.13187 (15)	0.39198 (17)	0.0407
C22	0.71293 (17)	0.03516 (12)	0.31692 (12)	0.0215
C13	0.81317 (18)	0.53609 (13)	0.23699 (13)	0.0271
C7	0.3352 (2)	0.30142 (16)	0.27477 (16)	0.0353
C20	0.8694 (2)	0.56661 (16)	0.30151 (16)	0.0350
C26	0.5588 (3)	−0.06400 (19)	0.23357 (17)	0.0481
C29	1.09991 (19)	0.29500 (14)	0.13550 (14)	0.0292
C11	0.9451 (2)	0.25422 (15)	0.47156 (15)	0.0318
C10	0.8091 (2)	0.02830 (15)	0.59672 (15)	0.0368
C9	0.7632 (2)	0.13635 (15)	0.60581 (13)	0.0306
C31	0.96219 (19)	0.34874 (14)	−0.02537 (14)	0.0292
C12	0.9246 (2)	0.32466 (18)	0.54265 (19)	0.0443
C18	0.67329 (19)	0.55068 (14)	0.44603 (14)	0.0291
C39	0.6870 (2)	0.03333 (15)	−0.08190 (17)	0.0384
C30	1.2366 (2)	0.23783 (17)	0.07921 (17)	0.0383
C19	0.7691 (2)	0.60779 (16)	0.39467 (16)	0.0364
B2	0.72544 (18)	0.17896 (13)	0.01118 (13)	0.0192
B1	0.73891 (19)	0.46123 (14)	0.29648 (14)	0.0210
C6	0.4224 (3)	0.51715 (18)	0.14532 (18)	0.0628
C8	0.2125 (2)	0.3738 (2)	0.3295 (2)	0.0573
H161	0.4524	0.6346	0.3933	0.0313*
H162	0.4844	0.5690	0.3062	0.0313*
H141	0.7610	0.6714	0.1655	0.0343*
H142	0.6990	0.5966	0.1453	0.0343*
H371	0.8952	0.0569	0.0243	0.0258*
H331	0.5736	0.2742	−0.0495	0.0273*
H341	0.7649	0.2935	−0.1577	0.0317*
H342	0.6965	0.2512	−0.2124	0.0317*
H401	0.5471	0.1546	−0.1185	0.0403*
H402	0.5211	0.1326	−0.0034	0.0403*
H381	0.8598	−0.0535	−0.0537	0.0381*
H382	0.7410	−0.0160	0.0425	0.0381*
H271	0.6795	−0.0051	0.4602	0.0315*
H272	0.5987	−0.0419	0.4114	0.0315*
H151	0.5995	0.7128	0.3044	0.0376*
H152	0.5239	0.7091	0.2312	0.0376*
H51	0.6065	0.4235	0.0988	0.0347*
H52	0.4929	0.3776	0.1080	0.0347*
H321	0.8879	0.4888	−0.0816	0.0442*
H322	0.8540	0.4803	0.0344	0.0442*
H323	0.7749	0.4421	−0.0148	0.0442*
H251	0.4631	0.0501	0.3210	0.0424*
H252	0.4792	0.0836	0.2082	0.0424*
H171	0.5700	0.4720	0.4238	0.0241*
H361	0.9777	0.1508	−0.1073	0.0310*
H362	1.0063	0.0446	−0.1405	0.0310*
H351	0.9332	0.1798	−0.2507	0.0363*
H352	0.8522	0.1026	−0.2202	0.0363*
H281	0.7680	−0.1758	0.4501	0.0441*
H282	0.8760	−0.1244	0.3834	0.0441*
H283	0.7952	−0.1612	0.3346	0.0441*
H131	0.8886	0.5066	0.1811	0.0301*
H71	0.3446	0.3131	0.2047	0.0471*
H72	0.3281	0.2341	0.2959	0.0471*
H201	0.9114	0.6165	0.2649	0.0418*
H202	0.9376	0.5089	0.3192	0.0418*
H261	0.4784	−0.0796	0.2395	0.0640*
H262	0.6031	−0.1085	0.2796	0.0640*
H263	0.6192	−0.0750	0.1668	0.0640*
H291	1.0975	0.2948	0.2033	0.0376*
H292	1.0798	0.3633	0.1071	0.0376*
H111	0.9889	0.1873	0.4946	0.0403*
H112	1.0041	0.2710	0.4080	0.0403*
H101	0.8218	−0.0076	0.6580	0.0427*
H102	0.8936	0.0097	0.5443	0.0427*
H103	0.7428	0.0098	0.5808	0.0427*
H91	0.8300	0.1529	0.6228	0.0393*
H92	0.6793	0.1530	0.6592	0.0393*
H311	1.0486	0.3563	−0.0335	0.0337*
H312	0.9695	0.3182	−0.0827	0.0337*
H121	1.0088	0.3210	0.5502	0.0583*
H122	0.8660	0.3085	0.6069	0.0583*
H123	0.8812	0.3923	0.5203	0.0583*
H181	0.5984	0.5918	0.4943	0.0374*
H182	0.7203	0.4922	0.4813	0.0374*
H391	0.7370	0.0297	−0.1518	0.0513*
H392	0.6374	−0.0144	−0.0635	0.0513*
H301	1.3019	0.2666	0.0810	0.0476*
H302	1.2584	0.1693	0.1070	0.0476*
H303	1.2407	0.2378	0.0107	0.0476*
H191	0.8165	0.6104	0.4389	0.0473*
H192	0.7172	0.6757	0.3787	0.0473*
H61	0.4179	0.5468	0.0803	0.0693*
H62	0.4465	0.5598	0.1762	0.0693*
H63	0.3330	0.5139	0.1853	0.0693*
H81	0.1340	0.3693	0.3179	0.0716*
H82	0.2181	0.4407	0.3088	0.0716*
H83	0.2016	0.3618	0.4000	0.0716*
H1	0.9622	0.0981	0.3067	0.0500*
H2	0.4983	0.1708	0.4944	0.0500*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Ni2	0.01822 (11)	0.01651 (11)	0.01600 (11)	−0.00675 (8)	−0.00407 (8)	−0.00139 (8)
Ni1	0.02002 (11)	0.01686 (11)	0.01714 (11)	−0.00500 (8)	−0.00632 (8)	−0.00045 (8)
O2	0.0267 (6)	0.0210 (6)	0.0184 (6)	−0.0084 (5)	−0.0017 (5)	−0.0009 (5)
O6	0.0202 (6)	0.0235 (6)	0.0186 (6)	−0.0058 (5)	−0.0071 (5)	−0.0011 (5)
O1	0.0195 (6)	0.0218 (6)	0.0240 (6)	−0.0070 (5)	−0.0035 (5)	0.0019 (5)
O7	0.0278 (7)	0.0324 (7)	0.0219 (6)	−0.0096 (5)	−0.0127 (5)	0.0021 (5)
O5	0.0237 (6)	0.0202 (6)	0.0199 (6)	−0.0068 (5)	−0.0082 (5)	0.0006 (5)
O8	0.0284 (7)	0.0303 (7)	0.0285 (7)	−0.0104 (5)	−0.0150 (5)	−0.0017 (5)
O4	0.0326 (7)	0.0283 (7)	0.0260 (7)	−0.0165 (6)	−0.0079 (5)	0.0052 (5)
N7	0.0233 (7)	0.0193 (7)	0.0173 (7)	−0.0060 (6)	−0.0056 (5)	−0.0020 (5)
N2	0.0227 (7)	0.0168 (7)	0.0192 (7)	−0.0033 (6)	−0.0043 (6)	−0.0025 (5)
N5	0.0214 (7)	0.0179 (7)	0.0183 (7)	−0.0056 (5)	−0.0047 (5)	−0.0026 (5)
O3	0.0357 (8)	0.0327 (7)	0.0352 (8)	−0.0212 (6)	−0.0129 (6)	0.0059 (6)
N1	0.0214 (7)	0.0186 (7)	0.0194 (7)	−0.0047 (6)	−0.0042 (6)	−0.0033 (5)
N4	0.0273 (8)	0.0191 (7)	0.0185 (7)	−0.0079 (6)	−0.0050 (6)	−0.0006 (5)
N3	0.0238 (7)	0.0209 (7)	0.0249 (7)	−0.0076 (6)	−0.0071 (6)	−0.0021 (6)
N6	0.0210 (7)	0.0173 (6)	0.0156 (6)	−0.0052 (5)	−0.0050 (5)	−0.0028 (5)
N8	0.0223 (7)	0.0212 (7)	0.0211 (7)	−0.0059 (6)	−0.0070 (6)	−0.0044 (6)
C21	0.0237 (8)	0.0202 (8)	0.0189 (8)	−0.0074 (7)	−0.0036 (6)	−0.0039 (6)
C2	0.0242 (9)	0.0244 (9)	0.0277 (9)	−0.0035 (7)	−0.0104 (7)	−0.0069 (7)
C16	0.0200 (8)	0.0248 (9)	0.0316 (9)	−0.0022 (7)	−0.0031 (7)	−0.0065 (7)
C14	0.033 (1)	0.0225 (9)	0.031 (1)	−0.0088 (8)	−0.0028 (8)	0.0051 (7)
C37	0.0237 (8)	0.0206 (8)	0.0195 (8)	0.0009 (7)	−0.0092 (7)	−0.0018 (6)
C24	0.0189 (8)	0.0187 (8)	0.0228 (8)	−0.0042 (6)	0.0001 (6)	−0.0038 (6)
C33	0.0208 (8)	0.0207 (8)	0.0239 (8)	−0.0005 (6)	−0.0079 (7)	−0.0021 (6)
C34	0.031 (1)	0.029 (1)	0.0213 (8)	0.0011 (8)	−0.0125 (7)	0.0030 (7)
C40	0.034 (1)	0.028 (1)	0.0376 (11)	−0.0054 (8)	−0.0218 (9)	−0.0028 (8)
C38	0.0363 (11)	0.0182 (8)	0.033 (1)	−0.0003 (7)	−0.0131 (8)	−0.0064 (7)
C27	0.0297 (9)	0.0295 (9)	0.0202 (8)	−0.0117 (8)	−0.0035 (7)	0.0026 (7)
C15	0.031 (1)	0.0235 (9)	0.0394 (11)	−0.0027 (8)	−0.0066 (9)	−0.0008 (8)
C5	0.032 (1)	0.033 (1)	0.0224 (9)	−0.0022 (8)	−0.0113 (8)	−0.0020 (7)
C23	0.0201 (8)	0.0208 (8)	0.0268 (9)	−0.0064 (7)	−0.0024 (7)	−0.0082 (7)
C32	0.0423 (12)	0.029 (1)	0.0387 (11)	−0.0146 (9)	−0.0061 (9)	0.0081 (8)
C1	0.0243 (8)	0.0190 (8)	0.0205 (8)	0.0012 (7)	−0.0085 (7)	−0.0054 (6)
C25	0.033 (1)	0.0417 (11)	0.031 (1)	−0.0241 (9)	−0.0109 (8)	0.0058 (8)
C17	0.0186 (8)	0.0208 (8)	0.0205 (8)	−0.0066 (6)	−0.0007 (6)	−0.0045 (6)
C36	0.0252 (9)	0.032 (1)	0.0186 (8)	0.0038 (7)	−0.0048 (7)	−0.0020 (7)
C4	0.0253 (9)	0.0218 (8)	0.0213 (8)	−0.0047 (7)	−0.0078 (7)	−0.0030 (6)
C3	0.0306 (9)	0.0225 (8)	0.0190 (8)	−0.0065 (7)	−0.0084 (7)	−0.0019 (6)
C35	0.030 (1)	0.0412 (11)	0.0182 (8)	0.0032 (8)	−0.0060 (7)	−0.0013 (8)
C28	0.0384 (12)	0.029 (1)	0.0422 (12)	−0.0106 (9)	−0.0036 (9)	0.0096 (9)
C22	0.0236 (8)	0.0204 (8)	0.0189 (8)	−0.0074 (7)	−0.0028 (6)	−0.0032 (6)
C13	0.0223 (9)	0.0229 (9)	0.0271 (9)	−0.0053 (7)	0.0020 (7)	−0.0017 (7)
C7	0.0382 (11)	0.0389 (11)	0.0387 (11)	−0.0140 (9)	−0.0222 (9)	−0.0021 (9)
C20	0.027 (1)	0.0361 (11)	0.0415 (11)	−0.0158 (8)	−0.0048 (8)	0.0007 (9)
C26	0.0697 (17)	0.0526 (14)	0.0381 (12)	−0.0453 (13)	−0.0086 (11)	−0.004 (1)
C29	0.0277 (9)	0.0284 (9)	0.035 (1)	−0.0143 (8)	−0.0051 (8)	−0.0078 (8)
C11	0.030 (1)	0.035 (1)	0.034 (1)	−0.0101 (8)	−0.0166 (8)	0.0017 (8)
C10	0.0443 (12)	0.032 (1)	0.030 (1)	−0.0061 (9)	−0.0171 (9)	0.0086 (8)
C9	0.0423 (11)	0.033 (1)	0.0212 (9)	−0.0145 (9)	−0.0155 (8)	0.0044 (7)
C31	0.0282 (9)	0.031 (1)	0.0254 (9)	−0.0150 (8)	−0.0005 (7)	0.0021 (7)
C12	0.0496 (14)	0.0425 (12)	0.0559 (14)	−0.016 (1)	−0.0323 (12)	−0.0037 (11)
C18	0.030 (1)	0.032 (1)	0.0269 (9)	−0.0137 (8)	−0.0033 (8)	−0.0077 (7)
C39	0.0488 (13)	0.029 (1)	0.0442 (12)	−0.0075 (9)	−0.023 (1)	−0.0098 (9)
C30	0.0227 (9)	0.0453 (12)	0.0504 (13)	−0.0122 (9)	−0.0082 (9)	−0.014 (1)
C19	0.0372 (11)	0.0415 (12)	0.0392 (11)	−0.023 (1)	−0.0079 (9)	−0.0092 (9)
B2	0.0197 (9)	0.0174 (8)	0.0181 (8)	−0.0035 (7)	−0.0044 (7)	−0.0029 (7)
B1	0.0197 (9)	0.0191 (9)	0.0205 (9)	−0.0038 (7)	−0.0038 (7)	−0.0018 (7)
C6	0.099 (2)	0.0326 (12)	0.0368 (13)	0.0152 (13)	−0.0340 (14)	−0.001 (1)
C8	0.0279 (11)	0.0723 (18)	0.0782 (19)	−0.0171 (12)	−0.0166 (12)	−0.0168 (15)

Geometric parameters (Å, º) top

Ni1—N1	1.8651 (15)	C5—C1	1.494 (2)
Ni1—N2	1.8612 (14)	C5—C6	1.498 (3)
Ni1—N3	1.8612 (15)	C5—H51	1.008
Ni1—N4	1.8598 (15)	C5—H52	1.004
Ni2—N5	1.8626 (14)	C23—C29	1.491 (2)
Ni2—N6	1.8570 (14)	C32—C31	1.521 (3)
Ni2—N7	1.8630 (14)	C32—H321	0.999
Ni2—N8	1.8666 (15)	C32—H322	1.004
O1—N1	1.3630 (18)	C32—H323	1.006
O1—B1	1.539 (2)	C25—C26	1.523 (3)
O2—N2	1.3571 (19)	C25—H251	1.007
O2—B1	1.532 (2)	C25—H252	1.006
O3—N3	1.338 (2)	C17—B1	1.611 (2)
O4—N4	1.3468 (19)	C17—H171	1.008
O4—H2	1.038	C36—C35	1.530 (3)
O5—N5	1.3539 (19)	C36—H361	1.011
O5—B2	1.530 (2)	C36—H362	1.004
O6—N6	1.3601 (18)	C4—C11	1.490 (3)
O6—B2	1.533 (2)	C3—C9	1.497 (2)
O7—N7	1.3318 (19)	C35—H351	1.011
O7—H1	1.287	C35—H352	1.009
O8—N8	1.3405 (19)	C28—H281	1.000
O8—H1	1.167	C28—H282	1.005
N1—C4	1.297 (2)	C28—H283	1.004
N2—C1	1.295 (2)	C13—C20	1.532 (3)
N3—C2	1.300 (2)	C13—B1	1.597 (3)
N4—C3	1.291 (2)	C13—H131	1.009
N5—C24	1.291 (2)	C7—C8	1.514 (4)
N6—C21	1.296 (2)	C7—H71	1.004
N7—C22	1.305 (2)	C7—H72	1.016
N8—C23	1.299 (2)	C20—C19	1.539 (3)
C1—C2	1.473 (3)	C20—H201	1.004
C3—C4	1.482 (3)	C20—H202	1.006
C17—C18	1.536 (3)	C26—H261	1.003
C21—C22	1.473 (2)	C26—H262	1.003
C24—C23	1.469 (3)	C26—H263	1.007
C21—C25	1.495 (3)	C29—C30	1.527 (3)
C2—C7	1.493 (3)	C29—H291	1.004
C16—C15	1.534 (3)	C29—H292	1.005
C16—C17	1.533 (3)	C11—C12	1.532 (3)
C16—H161	1.005	C11—H111	1.003
C16—H162	1.011	C11—H112	1.010
C14—C15	1.542 (3)	C10—C9	1.523 (3)
C14—C13	1.546 (3)	C10—H101	1.001
C14—H141	1.000	C10—H102	1.004
C14—H142	1.011	C10—H103	1.005
C37—C38	1.543 (3)	C9—H91	1.002
C37—C36	1.536 (2)	C9—H92	1.006
C37—B2	1.605 (2)	C31—H311	1.005
C37—H371	1.006	C31—H312	1.008
C24—C31	1.500 (2)	C12—H121	0.996
C33—C34	1.544 (3)	C12—H122	1.012
C33—C40	1.544 (3)	C12—H123	1.006
C33—B2	1.588 (3)	C18—C19	1.540 (3)
C33—H331	1.008	C18—H181	1.003
C34—C35	1.542 (3)	C18—H182	1.012
C34—H341	1.006	C39—H391	1.007
C34—H342	1.006	C39—H392	1.007
C40—C39	1.534 (3)	C30—H301	0.997
C40—H401	1.003	C30—H302	1.006
C40—H402	1.010	C30—H303	1.008
C38—C39	1.543 (3)	C19—H191	1.004
C38—H381	1.006	C19—H192	1.010
C38—H382	1.010	C6—H61	1.002
C27—C28	1.532 (3)	C6—H62	1.005
C27—C22	1.497 (2)	C6—H63	1.013
C27—H271	1.006	C8—H81	1.004
C27—H272	1.004	C8—H82	1.004
C15—H151	1.010	C8—H83	1.007
C15—H152	1.003

Ni1—N1—O1	124.48 (11)	C16—C17—B1	108.91 (14)
Ni1—N1—C4	116.06 (12)	C18—C17—B1	109.03 (14)
Ni1—N2—O2	123.71 (11)	C16—C17—H171	107.028
Ni1—N2—C1	116.45 (13)	C18—C17—H171	107.043
Ni1—N3—O3	123.62 (12)	B1—C17—H171	111.488
Ni1—N3—C2	116.31 (13)	C37—C36—C35	114.29 (16)
Ni1—N4—O4	123.67 (12)	C37—C36—H361	108.220
Ni1—N4—C3	116.57 (12)	C35—C36—H361	108.195
Ni2—N5—O5	125.35 (11)	C37—C36—H362	108.618
Ni2—N5—C24	116.65 (12)	C35—C36—H362	109.153
Ni2—N6—O6	123.6 (1)	H361—C36—H362	108.206
Ni2—N6—C21	116.79 (12)	N1—C4—C11	124.69 (17)
Ni2—N7—O7	123.22 (11)	C3—C4—C11	123.31 (16)
Ni2—N7—C22	116.26 (12)	N4—C3—C9	123.45 (17)
Ni2—N8—O8	123.44 (11)	C4—C3—C9	124.18 (17)
Ni2—N8—C23	116.23 (12)	C34—C35—C36	114.27 (15)
O1—N1—C4	119.01 (15)	C34—C35—H351	108.704
O2—N2—C1	119.53 (15)	C36—C35—H351	108.971
O2—B1—O1	106.97 (13)	C34—C35—H352	108.378
O3—N3—C2	120.04 (16)	C36—C35—H352	108.413
O4—N4—C3	119.72 (15)	H351—C35—H352	107.931
O5—N5—C24	117.97 (14)	C27—C28—H281	110.413
O6—N6—C21	119.36 (14)	C27—C28—H282	109.747
O6—B2—O5	107.78 (13)	H281—C28—H282	109.061
O7—N7—C22	120.52 (14)	C27—C28—H283	109.718
O8—N8—C23	120.28 (15)	H281—C28—H283	109.126
N1—Ni1—N3	177.37 (6)	H282—C28—H283	108.745
N1—Ni1—N4	82.60 (6)	N7—C22—C27	122.83 (16)
N1—O1—B1	111.77 (12)	C21—C22—C27	125.01 (16)
N1—C4—C3	112.00 (16)	C14—C13—C20	113.40 (16)
N2—Ni1—N1	97.62 (6)	C14—C13—B1	108.54 (15)
N2—Ni1—N3	82.54 (7)	C20—C13—B1	109.07 (15)
N2—Ni1—N4	178.05 (6)	C14—C13—H131	107.153
N2—O2—B1	112.95 (12)	C20—C13—H131	106.876
N2—C1—C2	112.15 (15)	B1—C13—H131	111.846
N2—C1—C5	124.35 (17)	C2—C7—C8	111.08 (18)
N3—C2—C1	112.22 (16)	C2—C7—H71	109.881
N4—Ni1—N3	97.14 (7)	C8—C7—H71	109.718
N4—C3—C4	112.23 (15)	C2—C7—H72	109.104
N5—Ni2—N6	97.40 (6)	C8—C7—H72	109.094
N5—Ni2—N8	82.29 (6)	H71—C7—H72	107.894
N5—O5—B2	113.58 (12)	C13—C20—C19	114.56 (16)
N5—C24—C23	112.42 (15)	C13—C20—H201	108.692
N6—Ni2—N8	177.77 (6)	C19—C20—H201	108.467
N6—O6—B2	112.79 (12)	C13—C20—H202	108.604
N6—C21—C22	112.16 (15)	C19—C20—H202	107.693
N7—Ni2—N5	179.21 (6)	H201—C20—H202	108.697
N7—Ni2—N6	82.56 (6)	C25—C26—H261	110.529
N7—Ni2—N8	97.72 (6)	C25—C26—H262	110.131
N7—C22—C21	112.14 (15)	H261—C26—H262	108.935
N8—C23—C24	112.19 (15)	C25—C26—H263	109.876
C2—C1—C5	123.48 (16)	H261—C26—H263	108.658
N7—O7—H1	100.552	H262—C26—H263	108.669
N8—O8—H1	99.992	C23—C29—C30	112.55 (15)
N4—O4—H2	104.270	C23—C29—H291	109.142
N6—C21—C25	124.39 (16)	C30—C29—H291	108.748
C25—C21—C22	123.45 (15)	C23—C29—H292	108.850
N3—C2—C7	122.97 (18)	C30—C29—H292	108.779
C1—C2—C7	124.62 (17)	H291—C29—H292	108.701
C15—C16—C17	114.44 (15)	C4—C11—C12	112.91 (18)
C15—C16—H161	108.823	C4—C11—H111	109.103
C17—C16—H161	108.719	C12—C11—H111	109.070
C15—C16—H162	108.007	C4—C11—H112	108.781
C17—C16—H162	108.512	C12—C11—H112	108.443
H161—C16—H162	108.181	H111—C11—H112	108.441
C15—C14—C13	116.27 (16)	C9—C10—H101	110.430
C15—C14—H141	108.565	C9—C10—H102	109.803
C13—C14—H141	108.225	H101—C10—H102	109.018
C15—C14—H142	107.188	C9—C10—H103	109.906
C13—C14—H142	107.756	H101—C10—H103	108.932
H141—C14—H142	108.629	H102—C10—H103	108.718
C38—C37—C36	113.64 (15)	C3—C9—C10	114.55 (16)
C38—C37—B2	108.76 (15)	C3—C9—H91	108.629
C36—C37—B2	108.74 (14)	C10—C9—H91	108.398
C38—C37—H371	106.915	C3—C9—H92	108.159
C36—C37—H371	106.716	C10—C9—H92	108.194
B2—C37—H371	112.124	H91—C9—H92	108.790
N5—C24—C31	123.34 (17)	C24—C31—C32	114.47 (16)
C23—C24—C31	124.17 (16)	C24—C31—H311	108.597
C34—C33—C40	114.17 (16)	C32—C31—H311	108.521
C34—C33—B2	108.40 (14)	C24—C31—H312	108.213
C40—C33—B2	108.44 (14)	C32—C31—H312	108.433
C34—C33—H331	106.837	H311—C31—H312	108.469
C40—C33—H331	106.528	C11—C12—H121	111.029
B2—C33—H331	112.550	C11—C12—H122	109.432
C33—C34—C35	114.99 (15)	H121—C12—H122	108.843
C33—C34—H341	108.415	C11—C12—H123	110.057
C35—C34—H341	107.862	H121—C12—H123	109.331
C33—C34—H342	108.427	H122—C12—H123	108.089
C35—C34—H342	108.470	C17—C18—C19	116.17 (16)
H341—C34—H342	108.523	C17—C18—H181	108.556
C33—C40—C39	115.28 (17)	C19—C18—H181	108.259
C33—C40—H401	108.162	C17—C18—H182	108.171
C39—C40—H401	108.867	C19—C18—H182	107.169
C33—C40—H402	107.886	H181—C18—H182	108.275
C39—C40—H402	108.078	C40—C39—C38	114.55 (16)
H401—C40—H402	108.381	C40—C39—H391	108.335
C37—C38—C39	115.68 (16)	C38—C39—H391	107.927
C37—C38—H381	108.375	C40—C39—H392	108.917
C39—C38—H381	108.485	C38—C39—H392	108.594
C37—C38—H382	108.131	H391—C39—H392	108.357
C39—C38—H382	107.766	C29—C30—H301	110.704
H381—C38—H382	108.183	C29—C30—H302	109.765
C28—C27—C22	112.33 (15)	H301—C30—H302	109.262
C28—C27—H271	108.811	C29—C30—H303	109.654
C22—C27—H271	108.845	H301—C30—H303	109.045
C28—C27—H272	108.895	H302—C30—H303	108.369
C22—C27—H272	109.196	C20—C19—C18	114.25 (17)
H271—C27—H272	108.695	C20—C19—H191	108.801
C16—C15—C14	114.57 (15)	C18—C19—H191	109.231
C16—C15—H151	108.257	C20—C19—H192	108.013
C14—C15—H151	107.521	C18—C19—H192	108.058
C16—C15—H152	109.365	H191—C19—H192	108.330
C14—C15—H152	108.583	O6—B2—C37	112.65 (14)
H151—C15—H152	108.378	O5—B2—C37	112.07 (14)
C1—C5—C6	114.59 (17)	O6—B2—C33	108.22 (14)
C1—C5—H51	108.260	O5—B2—C33	107.66 (14)
C6—C5—H51	108.133	C37—B2—C33	108.28 (14)
C1—C5—H52	108.446	O2—B1—C17	113.18 (14)
C6—C5—H52	108.702	O1—B1—C17	111.62 (14)
H51—C5—H52	108.571	O2—B1—C13	107.58 (14)
N8—C23—C29	123.46 (17)	O1—B1—C13	109.81 (14)
C24—C23—C29	124.33 (16)	C17—B1—C13	107.59 (14)
C31—C32—H321	110.540	C5—C6—H61	111.033
C31—C32—H322	109.692	C5—C6—H62	110.498
H321—C32—H322	109.206	H61—C6—H62	108.976
C31—C32—H323	109.684	C5—C6—H63	109.835
H321—C32—H323	109.041	H61—C6—H63	108.336
H322—C32—H323	108.645	H62—C6—H63	108.086
C21—C25—C26	113.21 (19)	C7—C8—H81	110.884
C21—C25—H251	108.632	C7—C8—H82	109.819
C26—C25—H251	108.830	H81—C8—H82	108.835
C21—C25—H252	108.598	C7—C8—H83	110.122
C26—C25—H252	109.033	H81—C8—H83	108.563
H251—C25—H252	108.434	H82—C8—H83	108.565
C16—C17—C18	113.35 (15)	O7—H1—O8	171.661

Experimental details

Crystal data
Chemical formula	[Ni(C₂₀H₃₅BN₄O₄)]
M_r	465.04
Crystal system, space group	Triclinic, P1
Temperature (K)	150
a, b, c (Å)	11.5210 (2), 14.8794 (2), 14.9455 (3)
α, β, γ (°)	79.4462 (6), 70.0605 (7), 69.4812 (11)
V (Å³)	2249.76 (7)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.90
Crystal size (mm)	0.30 × 0.20 × 0.19

Data collection
Diffractometer	Enraf-Nonius KappaCCD diffractometer
Absorption correction	Multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997)
T_min, T_max	0.84, 0.84
No. of measured, independent and observed [I > 3σ(I)] reflections	16886, 9767, 7437
R_int	0.01
(sin θ/λ)_max (Å⁻¹)	0.648

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.038, 1.04
No. of reflections	7437
No. of parameters	541
No. of restraints	?
H-atom treatment	H-atom parameters not refined
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.35

Computer programs: COLLECT (Nonius, 1997-2001), DENZO/SCALEPACK (Otwinowski & Minor, 1997), DENZO/SCALEPACK, SIR92 (Altomare et al., 1994), CRYSTALS (Watkin et al., 2001), CAMERON (Watkin et al., 1996), CRYSTALS.

Selected geometric parameters (Å, º) top

Ni1—N1	1.8651 (15)	O6—N6	1.3601 (18)
Ni1—N2	1.8612 (14)	O6—B2	1.533 (2)
Ni1—N3	1.8612 (15)	O7—N7	1.3318 (19)
Ni1—N4	1.8598 (15)	O8—N8	1.3405 (19)
Ni2—N5	1.8626 (14)	N1—C4	1.297 (2)
Ni2—N6	1.8570 (14)	N2—C1	1.295 (2)
Ni2—N7	1.8630 (14)	N3—C2	1.300 (2)
Ni2—N8	1.8666 (15)	N4—C3	1.291 (2)
O1—N1	1.3630 (18)	N5—C24	1.291 (2)
O1—B1	1.539 (2)	N6—C21	1.296 (2)
O2—N2	1.3571 (19)	N7—C22	1.305 (2)
O2—B1	1.532 (2)	N8—C23	1.299 (2)
O3—N3	1.338 (2)	C1—C2	1.473 (3)
O4—N4	1.3468 (19)	C3—C4	1.482 (3)
O5—N5	1.3539 (19)	C21—C22	1.473 (2)
O5—B2	1.530 (2)	C24—C23	1.469 (3)

Ni1—N1—O1	124.48 (11)	N1—Ni1—N3	177.37 (6)
Ni1—N1—C4	116.06 (12)	N1—Ni1—N4	82.60 (6)
Ni1—N2—O2	123.71 (11)	N1—O1—B1	111.77 (12)
Ni1—N2—C1	116.45 (13)	N1—C4—C3	112.00 (16)
Ni1—N3—O3	123.62 (12)	N2—Ni1—N1	97.62 (6)
Ni1—N3—C2	116.31 (13)	N2—Ni1—N3	82.54 (7)
Ni1—N4—O4	123.67 (12)	N2—Ni1—N4	178.05 (6)
Ni1—N4—C3	116.57 (12)	N2—O2—B1	112.95 (12)
Ni2—N5—O5	125.35 (11)	N2—C1—C2	112.15 (15)
Ni2—N5—C24	116.65 (12)	N2—C1—C5	124.35 (17)
Ni2—N6—O6	123.6 (1)	N3—C2—C1	112.22 (16)
Ni2—N6—C21	116.79 (12)	N4—Ni1—N3	97.14 (7)
Ni2—N7—O7	123.22 (11)	N4—C3—C4	112.23 (15)
Ni2—N7—C22	116.26 (12)	N5—Ni2—N6	97.40 (6)
Ni2—N8—O8	123.44 (11)	N5—Ni2—N8	82.29 (6)
Ni2—N8—C23	116.23 (12)	N5—O5—B2	113.58 (12)
O1—N1—C4	119.01 (15)	N5—C24—C23	112.42 (15)
O2—N2—C1	119.53 (15)	N6—Ni2—N8	177.77 (6)
O2—B1—O1	106.97 (13)	N6—O6—B2	112.79 (12)
O3—N3—C2	120.04 (16)	N6—C21—C22	112.16 (15)
O4—N4—C3	119.72 (15)	N7—Ni2—N5	179.21 (6)
O5—N5—C24	117.97 (14)	N7—Ni2—N6	82.56 (6)
O6—N6—C21	119.36 (14)	N7—Ni2—N8	97.72 (6)
O6—B2—O5	107.78 (13)	N7—C22—C21	112.14 (15)
O7—N7—C22	120.52 (14)	N8—C23—C24	112.19 (15)
O8—N8—C23	120.28 (15)

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