Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680301729X/ci6243sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S160053680301729X/ci6243Isup2.hkl |
CCDC reference: 222806
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; δH (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); δC (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.
H atoms were located from a difference Fourier map and their positional and isotropic displacement parameters were not refined. Owing to the poor quality of the crystal, the data are only 95.3% complete to θmax of 27.4°.
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.
Fig. 1. The asymmetric unit of (I). Displacement ellipsoids are drawn at the 50% probability level for non-H atoms. |
[Ni(C20H35BN4O4)] | Z = 4 |
Mr = 465.04 | F(000) = 992.000 |
Triclinic, P1 | Dx = 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 |
Enraf-Nonius KappaCCD diffractometer | 7437 reflections with I > 3σ(I) |
Graphite monochromator | Rint = 0.01 |
ω scans | θmax = 27.4°, θmin = 4.1° |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | h = −14→14 |
Tmin = 0.84, Tmax = 0.84 | k = −19→19 |
16886 measured reflections | l = −19→19 |
9767 independent reflections |
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 | Δρmax = 0.30 e Å−3 |
541 parameters | Δρmin = −0.35 e Å−3 |
[Ni(C20H35BN4O4)] | γ = 69.4812 (11)° |
Mr = 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)° |
Enraf-Nonius KappaCCD diffractometer | 9767 independent reflections |
Absorption correction: multi-scan (DENZO/SCALEPACK; Otwinowski & Minor, 1997) | 7437 reflections with I > 3σ(I) |
Tmin = 0.84, Tmax = 0.84 | Rint = 0.01 |
16886 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 541 parameters |
wR(F2) = 0.038 | H-atom parameters not refined |
S = 1.04 | Δρmax = 0.30 e Å−3 |
7437 reflections | Δρmin = −0.35 e Å−3 |
x | y | z | Uiso*/Ueq | ||
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* |
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) |
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)] |
Mr | 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) |
Tmin, Tmax | 0.84, 0.84 |
No. of measured, independent and observed [I > 3σ(I)] reflections | 16886, 9767, 7437 |
Rint | 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 |
Δρmax, Δρmin (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.
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) |
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).