Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100003899/qb0173sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100003899/qb0173IIsup2.hkl |
CCDC reference: 144695
Analytically pure (II) (70 mg, 0.35 mmol) was dissolved in wet C6H5Cl (ca 0.5 ml) and layered with pentane (ca 3 ml). Colorless crystals of (II) formed after 3 d at 296 K.
Data collection: SMART (Bruker, 1996); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
(C8H19N2)[Ga(C6F5)4] | Dx = 1.743 Mg m−3 |
Mr = 881.21 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, Pbca | Cell parameters from 5204 reflections |
a = 21.4651 (12) Å | θ = 2–27° |
b = 13.3773 (8) Å | µ = 0.96 mm−1 |
c = 23.3868 (14) Å | T = 193 K |
V = 6715.4 (7) Å3 | Block, yellow |
Z = 8 | 0.35 × 0.32 × 0.10 mm |
F(000) = 3488 |
Bruker CCD area-detector diffractometer | 6850 independent reflections |
Radiation source: fine-focus sealed tube | 3685 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.084 |
ϕ scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | h = 0→26 |
Tmin = 0.730, Tmax = 0.910 | k = 0→16 |
31325 measured reflections | l = 0→29 |
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)] = 0.045 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.01 | w = 1/[σ2(Fo2) + (0.018P)2] where P = (Fo2 + 2Fc2)/3 |
6850 reflections | (Δ/σ)max < 0.001 |
501 parameters | Δρmax = 0.54 e Å−3 |
0 restraints | Δρmin = −0.62 e Å−3 |
(C8H19N2)[Ga(C6F5)4] | V = 6715.4 (7) Å3 |
Mr = 881.21 | Z = 8 |
Orthorhombic, Pbca | Mo Kα radiation |
a = 21.4651 (12) Å | µ = 0.96 mm−1 |
b = 13.3773 (8) Å | T = 193 K |
c = 23.3868 (14) Å | 0.35 × 0.32 × 0.10 mm |
Bruker CCD area-detector diffractometer | 6850 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | 3685 reflections with I > 2σ(I) |
Tmin = 0.730, Tmax = 0.910 | Rint = 0.084 |
31325 measured reflections |
R[F2 > 2σ(F2)] = 0.045 | 0 restraints |
wR(F2) = 0.075 | H-atom parameters constrained |
S = 1.01 | Δρmax = 0.54 e Å−3 |
6850 reflections | Δρmin = −0.62 e Å−3 |
501 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Ga | 0.194642 (15) | 0.51404 (3) | 0.085128 (15) | 0.02842 (10) | |
F2 | 0.15938 (8) | 0.35577 (13) | −0.00361 (8) | 0.0348 (5) | |
F3 | 0.09805 (9) | 0.18092 (14) | 0.00205 (8) | 0.0461 (6) | |
F4 | 0.04889 (9) | 0.11822 (15) | 0.10284 (9) | 0.0537 (6) | |
F5 | 0.06413 (9) | 0.23119 (16) | 0.19839 (9) | 0.0553 (6) | |
F6 | 0.12699 (9) | 0.40314 (15) | 0.19382 (8) | 0.0478 (6) | |
F8 | 0.25073 (8) | 0.70001 (14) | 0.02328 (9) | 0.0471 (6) | |
F9 | 0.21259 (9) | 0.80882 (15) | −0.06716 (9) | 0.0560 (6) | |
F10 | 0.09778 (9) | 0.77666 (16) | −0.11313 (9) | 0.0596 (6) | |
F11 | 0.02450 (9) | 0.62906 (15) | −0.07094 (9) | 0.0551 (6) | |
F12 | 0.06397 (7) | 0.51537 (14) | 0.01590 (8) | 0.0369 (5) | |
F14 | 0.28221 (8) | 0.52247 (15) | −0.02924 (7) | 0.0407 (5) | |
F15 | 0.40159 (8) | 0.47103 (16) | −0.04396 (8) | 0.0490 (6) | |
F16 | 0.46641 (8) | 0.38543 (16) | 0.04193 (9) | 0.0535 (6) | |
F17 | 0.41078 (8) | 0.35012 (16) | 0.14407 (9) | 0.0562 (6) | |
F18 | 0.29093 (8) | 0.40436 (16) | 0.16059 (8) | 0.0477 (6) | |
F20 | 0.30374 (9) | 0.61860 (15) | 0.16117 (8) | 0.0481 (6) | |
F21 | 0.29733 (9) | 0.73682 (16) | 0.25227 (9) | 0.0567 (6) | |
F22 | 0.18592 (10) | 0.78659 (16) | 0.29804 (9) | 0.0627 (6) | |
F23 | 0.07862 (9) | 0.71443 (16) | 0.25009 (9) | 0.0575 (6) | |
F24 | 0.08438 (8) | 0.59526 (16) | 0.15837 (8) | 0.0473 (6) | |
N1 | 0.10520 (13) | 0.1598 (2) | 0.34098 (13) | 0.0443 (9) | |
H1 | 0.1268 | 0.1933 | 0.3154 | 0.053* | |
N2 | 0.06356 (12) | 0.3095 (2) | 0.36789 (11) | 0.0353 (8) | |
H2 | 0.0390 | 0.3405 | 0.3923 | 0.042* | |
C1 | 0.14550 (13) | 0.3887 (2) | 0.09427 (14) | 0.0246 (8) | |
C2 | 0.13612 (14) | 0.3262 (3) | 0.04815 (14) | 0.0261 (8) | |
C3 | 0.10512 (15) | 0.2380 (3) | 0.04932 (16) | 0.0312 (9) | |
C4 | 0.07973 (15) | 0.2051 (3) | 0.10053 (17) | 0.0345 (9) | |
C5 | 0.08773 (15) | 0.2631 (3) | 0.14805 (16) | 0.0348 (9) | |
C6 | 0.12003 (15) | 0.3503 (3) | 0.14421 (16) | 0.0332 (9) | |
C7 | 0.15985 (14) | 0.6018 (2) | 0.02255 (13) | 0.0245 (8) | |
C8 | 0.19417 (15) | 0.6787 (3) | −0.00017 (15) | 0.0325 (8) | |
C9 | 0.17551 (16) | 0.7371 (3) | −0.04587 (16) | 0.0355 (9) | |
C10 | 0.11813 (18) | 0.7199 (3) | −0.06934 (15) | 0.0381 (10) | |
C11 | 0.08108 (15) | 0.6460 (3) | −0.04808 (15) | 0.0339 (9) | |
C12 | 0.10297 (14) | 0.5890 (2) | −0.00337 (15) | 0.0275 (8) | |
C13 | 0.28143 (14) | 0.4686 (2) | 0.06705 (14) | 0.0272 (8) | |
C14 | 0.31246 (14) | 0.4811 (2) | 0.01558 (14) | 0.0296 (8) | |
C15 | 0.37327 (16) | 0.4547 (3) | 0.00641 (15) | 0.0337 (9) | |
C16 | 0.40629 (15) | 0.4110 (3) | 0.04970 (16) | 0.0355 (9) | |
C17 | 0.37742 (16) | 0.3936 (3) | 0.10135 (16) | 0.0374 (10) | |
C18 | 0.31714 (15) | 0.4224 (3) | 0.10847 (15) | 0.0338 (9) | |
C19 | 0.19403 (15) | 0.6001 (2) | 0.15608 (13) | 0.0270 (8) | |
C20 | 0.24636 (16) | 0.6388 (3) | 0.18202 (15) | 0.0320 (9) | |
C21 | 0.24403 (17) | 0.7003 (3) | 0.22903 (16) | 0.0366 (10) | |
C22 | 0.18813 (18) | 0.7250 (3) | 0.25261 (15) | 0.0382 (9) | |
C23 | 0.13452 (17) | 0.6891 (3) | 0.22837 (16) | 0.0365 (10) | |
C24 | 0.13890 (15) | 0.6280 (3) | 0.18137 (15) | 0.0316 (9) | |
C25 | 0.18166 (17) | 0.0279 (3) | 0.35101 (19) | 0.0734 (14) | |
H25A | 0.2058 | 0.0495 | 0.3177 | 0.110* | |
H25B | 0.1865 | −0.0444 | 0.3562 | 0.110* | |
H25C | 0.1967 | 0.0627 | 0.3852 | 0.110* | |
C26 | 0.0887 (2) | 0.0053 (4) | 0.2896 (2) | 0.140 (3) | |
H26A | 0.0458 | 0.0281 | 0.2838 | 0.211* | |
H26B | 0.0892 | −0.0675 | 0.2939 | 0.211* | |
H26C | 0.1142 | 0.0245 | 0.2566 | 0.211* | |
C27 | 0.11424 (18) | 0.0521 (3) | 0.34183 (19) | 0.0545 (12) | |
H27 | 0.0905 | 0.0250 | 0.3752 | 0.065* | |
C28 | 0.06865 (14) | 0.2125 (3) | 0.37394 (15) | 0.0314 (9) | |
C29 | 0.03027 (15) | 0.1627 (3) | 0.41896 (15) | 0.0425 (10) | |
H29A | 0.0577 | 0.1289 | 0.4463 | 0.064* | |
H29B | 0.0025 | 0.1136 | 0.4011 | 0.064* | |
H29C | 0.0053 | 0.2131 | 0.4391 | 0.064* | |
C30 | 0.09452 (15) | 0.3723 (3) | 0.32468 (15) | 0.0385 (10) | |
H30 | 0.0968 | 0.3337 | 0.2881 | 0.046* | |
C31 | 0.05455 (18) | 0.4639 (3) | 0.31482 (16) | 0.0602 (12) | |
H31A | 0.0143 | 0.4436 | 0.2989 | 0.090* | |
H31B | 0.0756 | 0.5089 | 0.2880 | 0.090* | |
H31C | 0.0479 | 0.4986 | 0.3512 | 0.090* | |
C32 | 0.16051 (16) | 0.3991 (3) | 0.34296 (16) | 0.0565 (12) | |
H32A | 0.1589 | 0.4440 | 0.3760 | 0.085* | |
H32B | 0.1820 | 0.4324 | 0.3113 | 0.085* | |
H32C | 0.1831 | 0.3380 | 0.3533 | 0.085* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Ga | 0.02855 (19) | 0.0353 (2) | 0.0215 (2) | −0.00341 (19) | −0.00270 (19) | −0.0001 (2) |
F2 | 0.0441 (11) | 0.0412 (13) | 0.0192 (12) | 0.0017 (10) | 0.0035 (9) | 0.0004 (10) |
F3 | 0.0650 (13) | 0.0368 (13) | 0.0365 (14) | −0.0004 (11) | −0.0078 (11) | −0.0077 (12) |
F4 | 0.0639 (14) | 0.0374 (14) | 0.0598 (17) | −0.0148 (11) | 0.0033 (12) | 0.0044 (11) |
F5 | 0.0729 (15) | 0.0562 (15) | 0.0367 (15) | −0.0159 (12) | 0.0161 (12) | 0.0129 (12) |
F6 | 0.0746 (15) | 0.0482 (14) | 0.0207 (13) | −0.0152 (12) | 0.0067 (11) | −0.0014 (11) |
F8 | 0.0386 (12) | 0.0477 (14) | 0.0551 (15) | −0.0156 (11) | −0.0083 (10) | 0.0052 (11) |
F9 | 0.0713 (15) | 0.0441 (14) | 0.0526 (16) | −0.0087 (12) | 0.0116 (11) | 0.0165 (12) |
F10 | 0.0836 (16) | 0.0567 (15) | 0.0384 (15) | 0.0198 (13) | −0.0078 (12) | 0.0157 (12) |
F11 | 0.0432 (13) | 0.0697 (17) | 0.0525 (16) | 0.0084 (12) | −0.0239 (11) | 0.0044 (12) |
F12 | 0.0273 (10) | 0.0403 (12) | 0.0430 (13) | −0.0038 (10) | −0.0039 (9) | 0.0014 (11) |
F14 | 0.0405 (11) | 0.0615 (14) | 0.0202 (11) | 0.0146 (10) | −0.0046 (9) | 0.0056 (11) |
F15 | 0.0476 (12) | 0.0705 (16) | 0.0288 (13) | 0.0137 (12) | 0.0067 (10) | 0.0039 (12) |
F16 | 0.0357 (12) | 0.0720 (17) | 0.0529 (16) | 0.0166 (11) | −0.0003 (11) | 0.0083 (13) |
F17 | 0.0456 (13) | 0.0722 (17) | 0.0510 (15) | 0.0111 (12) | −0.0134 (11) | 0.0272 (13) |
F18 | 0.0469 (13) | 0.0615 (15) | 0.0347 (14) | 0.0001 (11) | −0.0018 (10) | 0.0216 (12) |
F20 | 0.0323 (11) | 0.0612 (14) | 0.0507 (15) | −0.0125 (11) | 0.0018 (11) | −0.0187 (11) |
F21 | 0.0583 (14) | 0.0657 (15) | 0.0461 (15) | −0.0196 (12) | −0.0180 (12) | −0.0166 (12) |
F22 | 0.0892 (17) | 0.0581 (15) | 0.0409 (15) | −0.0047 (13) | 0.0041 (13) | −0.0250 (13) |
F23 | 0.0539 (14) | 0.0663 (16) | 0.0523 (16) | 0.0087 (12) | 0.0162 (12) | −0.0125 (13) |
F24 | 0.0310 (11) | 0.0682 (16) | 0.0429 (15) | −0.0006 (11) | −0.0062 (10) | −0.0089 (12) |
N1 | 0.047 (2) | 0.042 (2) | 0.044 (2) | 0.0021 (16) | 0.0150 (16) | 0.0001 (18) |
N2 | 0.0419 (18) | 0.046 (2) | 0.0176 (18) | 0.0134 (16) | 0.0093 (14) | 0.0043 (16) |
C1 | 0.0191 (17) | 0.035 (2) | 0.020 (2) | 0.0005 (15) | −0.0020 (15) | 0.0023 (17) |
C2 | 0.0266 (19) | 0.035 (2) | 0.017 (2) | 0.0007 (17) | 0.0000 (16) | 0.0055 (18) |
C3 | 0.032 (2) | 0.032 (2) | 0.030 (2) | 0.0047 (18) | −0.0056 (18) | −0.0045 (19) |
C4 | 0.034 (2) | 0.025 (2) | 0.044 (3) | −0.0038 (17) | −0.0009 (18) | 0.006 (2) |
C5 | 0.042 (2) | 0.034 (2) | 0.028 (3) | −0.0037 (19) | 0.0051 (18) | 0.012 (2) |
C6 | 0.038 (2) | 0.037 (2) | 0.025 (2) | 0.0009 (18) | −0.0041 (18) | −0.0023 (19) |
C7 | 0.0246 (19) | 0.027 (2) | 0.021 (2) | 0.0039 (16) | −0.0016 (16) | −0.0028 (17) |
C8 | 0.0275 (19) | 0.035 (2) | 0.034 (2) | 0.0007 (19) | −0.0009 (19) | −0.0039 (19) |
C9 | 0.047 (3) | 0.029 (2) | 0.031 (2) | 0.0001 (18) | 0.0085 (19) | −0.0010 (19) |
C10 | 0.056 (3) | 0.031 (2) | 0.027 (3) | 0.014 (2) | −0.003 (2) | 0.0014 (19) |
C11 | 0.032 (2) | 0.039 (2) | 0.031 (2) | 0.0108 (19) | −0.0066 (18) | −0.0054 (19) |
C12 | 0.027 (2) | 0.027 (2) | 0.028 (2) | 0.0009 (17) | 0.0071 (17) | −0.0044 (18) |
C13 | 0.0329 (19) | 0.028 (2) | 0.021 (2) | −0.0019 (16) | −0.0076 (15) | −0.0021 (17) |
C14 | 0.0286 (19) | 0.035 (2) | 0.025 (2) | 0.0035 (18) | −0.0113 (17) | 0.0035 (18) |
C15 | 0.037 (2) | 0.037 (2) | 0.027 (2) | 0.0017 (17) | 0.0014 (18) | −0.0022 (18) |
C16 | 0.025 (2) | 0.043 (2) | 0.039 (3) | 0.0063 (18) | −0.0034 (19) | 0.002 (2) |
C17 | 0.035 (2) | 0.040 (2) | 0.037 (3) | 0.0035 (18) | −0.0162 (19) | 0.015 (2) |
C18 | 0.038 (2) | 0.036 (2) | 0.027 (2) | −0.0065 (18) | 0.0007 (18) | 0.0082 (18) |
C19 | 0.0309 (19) | 0.031 (2) | 0.019 (2) | −0.0047 (18) | −0.0028 (18) | 0.0002 (16) |
C20 | 0.029 (2) | 0.035 (2) | 0.031 (3) | −0.0040 (18) | −0.0006 (18) | 0.0006 (19) |
C21 | 0.045 (2) | 0.037 (2) | 0.027 (3) | −0.008 (2) | −0.0090 (19) | −0.0009 (19) |
C22 | 0.059 (3) | 0.033 (2) | 0.023 (2) | −0.002 (2) | −0.003 (2) | −0.0058 (18) |
C23 | 0.045 (2) | 0.036 (2) | 0.028 (3) | 0.007 (2) | 0.0063 (19) | −0.0006 (19) |
C24 | 0.029 (2) | 0.037 (2) | 0.028 (2) | −0.0035 (18) | −0.0066 (17) | 0.0021 (19) |
C25 | 0.076 (3) | 0.049 (3) | 0.095 (4) | 0.011 (3) | −0.025 (3) | −0.004 (3) |
C26 | 0.148 (5) | 0.077 (4) | 0.196 (7) | 0.034 (4) | −0.113 (5) | −0.075 (4) |
C27 | 0.068 (3) | 0.028 (2) | 0.067 (3) | 0.000 (2) | 0.014 (2) | −0.005 (2) |
C28 | 0.026 (2) | 0.047 (3) | 0.022 (2) | 0.0060 (18) | −0.0050 (16) | 0.007 (2) |
C29 | 0.038 (2) | 0.057 (3) | 0.032 (2) | −0.0038 (19) | 0.0003 (18) | 0.011 (2) |
C30 | 0.048 (2) | 0.044 (3) | 0.024 (2) | 0.000 (2) | 0.0097 (18) | −0.0002 (19) |
C31 | 0.079 (3) | 0.055 (3) | 0.046 (3) | 0.011 (2) | 0.012 (2) | 0.017 (2) |
C32 | 0.054 (3) | 0.063 (3) | 0.052 (3) | −0.007 (2) | 0.014 (2) | −0.023 (2) |
Ga—C1 | 1.993 (3) | C1—C6 | 1.388 (4) |
Ga—C13 | 2.005 (3) | C2—C3 | 1.355 (4) |
Ga—C7 | 2.019 (3) | C3—C4 | 1.387 (5) |
Ga—C19 | 2.020 (3) | C4—C5 | 1.366 (5) |
F2—C2 | 1.368 (3) | C5—C6 | 1.360 (4) |
F3—C3 | 1.352 (4) | C7—C8 | 1.373 (4) |
F4—C4 | 1.338 (4) | C7—C12 | 1.374 (4) |
F5—C5 | 1.351 (4) | C8—C9 | 1.383 (5) |
F6—C6 | 1.367 (4) | C9—C10 | 1.368 (4) |
F8—C8 | 1.362 (3) | C10—C11 | 1.363 (5) |
F9—C9 | 1.342 (4) | C11—C12 | 1.377 (4) |
F10—C10 | 1.347 (4) | C13—C18 | 1.381 (4) |
F11—C11 | 1.346 (3) | C13—C14 | 1.386 (4) |
F12—C12 | 1.369 (3) | C14—C15 | 1.369 (4) |
F14—C14 | 1.351 (3) | C15—C16 | 1.367 (4) |
F15—C15 | 1.344 (4) | C16—C17 | 1.377 (5) |
F16—C16 | 1.347 (3) | C17—C18 | 1.360 (4) |
F17—C17 | 1.360 (3) | C19—C24 | 1.375 (4) |
F18—C18 | 1.364 (4) | C19—C20 | 1.378 (4) |
F20—C20 | 1.352 (3) | C20—C21 | 1.374 (4) |
F21—C21 | 1.358 (3) | C21—C22 | 1.361 (4) |
F22—C22 | 1.346 (4) | C22—C23 | 1.369 (4) |
F23—C23 | 1.346 (4) | C23—C24 | 1.373 (5) |
F24—C24 | 1.360 (3) | C25—C27 | 1.498 (4) |
N1—C28 | 1.306 (4) | C26—C27 | 1.477 (5) |
N1—C27 | 1.454 (4) | C28—C29 | 1.493 (4) |
N2—C28 | 1.311 (4) | C30—C31 | 1.514 (5) |
N2—C30 | 1.472 (4) | C30—C32 | 1.522 (4) |
C1—C2 | 1.380 (4) | ||
C1—Ga—C13 | 105.03 (12) | C18—C13—Ga | 120.2 (3) |
C1—Ga—C7 | 111.78 (13) | C14—C13—Ga | 126.4 (2) |
C13—Ga—C7 | 111.54 (13) | F14—C14—C15 | 116.2 (3) |
C1—Ga—C19 | 112.84 (13) | F14—C14—C13 | 119.5 (3) |
C13—Ga—C19 | 110.62 (13) | C15—C14—C13 | 124.3 (3) |
C7—Ga—C19 | 105.18 (13) | F15—C15—C16 | 119.0 (3) |
C28—N1—C27 | 127.3 (3) | F15—C15—C14 | 121.8 (3) |
C28—N2—C30 | 126.9 (3) | C16—C15—C14 | 119.3 (3) |
C2—C1—C6 | 112.1 (3) | F16—C16—C15 | 120.3 (3) |
C2—C1—Ga | 120.2 (3) | F16—C16—C17 | 120.4 (3) |
C6—C1—Ga | 127.6 (3) | C15—C16—C17 | 119.2 (3) |
C3—C2—F2 | 116.7 (3) | F17—C17—C18 | 122.1 (3) |
C3—C2—C1 | 125.7 (3) | F17—C17—C16 | 118.7 (3) |
F2—C2—C1 | 117.6 (3) | C18—C17—C16 | 119.2 (3) |
F3—C3—C2 | 122.0 (3) | C17—C18—F18 | 116.9 (3) |
F3—C3—C4 | 118.9 (3) | C17—C18—C13 | 124.7 (3) |
C2—C3—C4 | 119.1 (3) | F18—C18—C13 | 118.5 (3) |
F4—C4—C5 | 121.5 (3) | C24—C19—C20 | 114.2 (3) |
F4—C4—C3 | 120.3 (3) | C24—C19—Ga | 120.9 (2) |
C5—C4—C3 | 118.2 (3) | C20—C19—Ga | 124.8 (3) |
F5—C5—C6 | 121.3 (3) | F20—C20—C21 | 116.2 (3) |
F5—C5—C4 | 118.8 (3) | F20—C20—C19 | 120.6 (3) |
C6—C5—C4 | 119.8 (3) | C21—C20—C19 | 123.2 (3) |
C5—C6—F6 | 116.3 (3) | F21—C21—C22 | 119.6 (3) |
C5—C6—C1 | 125.0 (3) | F21—C21—C20 | 120.3 (3) |
F6—C6—C1 | 118.7 (3) | C22—C21—C20 | 120.1 (3) |
C8—C7—C12 | 113.5 (3) | F22—C22—C21 | 120.0 (3) |
C8—C7—Ga | 121.2 (2) | F22—C22—C23 | 120.8 (3) |
C12—C7—Ga | 125.2 (3) | C21—C22—C23 | 119.2 (3) |
F8—C8—C7 | 118.6 (3) | F23—C23—C22 | 120.3 (3) |
F8—C8—C9 | 116.8 (3) | F23—C23—C24 | 120.8 (3) |
C7—C8—C9 | 124.6 (3) | C22—C23—C24 | 118.8 (3) |
F9—C9—C10 | 120.3 (3) | F24—C24—C23 | 116.7 (3) |
F9—C9—C8 | 121.2 (3) | F24—C24—C19 | 118.9 (3) |
C10—C9—C8 | 118.4 (3) | C23—C24—C19 | 124.4 (3) |
F10—C10—C11 | 119.8 (3) | N1—C27—C26 | 111.0 (4) |
F10—C10—C9 | 120.2 (4) | N1—C27—C25 | 110.2 (3) |
C11—C10—C9 | 120.1 (4) | C26—C27—C25 | 112.7 (4) |
F11—C11—C10 | 120.2 (3) | N1—C28—N2 | 121.4 (3) |
F11—C11—C12 | 121.1 (3) | N1—C28—C29 | 120.5 (3) |
C10—C11—C12 | 118.7 (3) | N2—C28—C29 | 118.1 (3) |
F12—C12—C7 | 119.2 (3) | N2—C30—C31 | 108.1 (3) |
F12—C12—C11 | 116.1 (3) | N2—C30—C32 | 111.2 (3) |
C7—C12—C11 | 124.7 (3) | C31—C30—C32 | 112.3 (3) |
C18—C13—C14 | 113.4 (3) |
Experimental details
Crystal data | |
Chemical formula | (C8H19N2)[Ga(C6F5)4] |
Mr | 881.21 |
Crystal system, space group | Orthorhombic, Pbca |
Temperature (K) | 193 |
a, b, c (Å) | 21.4651 (12), 13.3773 (8), 23.3868 (14) |
V (Å3) | 6715.4 (7) |
Z | 8 |
Radiation type | Mo Kα |
µ (mm−1) | 0.96 |
Crystal size (mm) | 0.35 × 0.32 × 0.10 |
Data collection | |
Diffractometer | Bruker CCD area-detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.730, 0.910 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 31325, 6850, 3685 |
Rint | 0.084 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.045, 0.075, 1.01 |
No. of reflections | 6850 |
No. of parameters | 501 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.54, −0.62 |
Computer programs: SMART (Bruker, 1996), SMART, SHELXTL (Sheldrick, 1997), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL.
Ga—C1 | 1.993 (3) | N1—C28 | 1.306 (4) |
Ga—C13 | 2.005 (3) | N1—C27 | 1.454 (4) |
Ga—C7 | 2.019 (3) | N2—C28 | 1.311 (4) |
Ga—C19 | 2.020 (3) | N2—C30 | 1.472 (4) |
C1—Ga—C13 | 105.03 (12) | C13—Ga—C19 | 110.62 (13) |
C1—Ga—C7 | 111.78 (13) | C7—Ga—C19 | 105.18 (13) |
C13—Ga—C7 | 111.54 (13) | C28—N1—C27 | 127.3 (3) |
C1—Ga—C19 | 112.84 (13) | C28—N2—C30 | 126.9 (3) |
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As part of our reactivity studies of cationic Group 13 metal complexes (Coles & Jordan, 1997; Ihara et al., 1998; Radzewich et al., 1998, 1999), the reaction of the Ga amidinate salt [{MeC(NiPr)2}2Ga2Me3][B(C6F5)4], (I), with H2O was investigated. Compound (I) reacts readily with H2O to yield the title compound, (II).
Complex (II) crystallizes as discrete acetamidinium cations {MeC(NHiPr)2}+ and Ga(C6F5)4- anions that form interionic hydrogen bonds. There are two likely hydrogen-bonding interactions N1—H1···F21(1/2 - x, -1/2 + y, z) and N2—H2···F16(-1/2 + x, y, 1/2 - z), with N···F separations of 3.121 (4) and 3.135 (3) Å, and N—H···F angles of 162 and 167°, respectively.
The bond distances and angles in the cation (Table 1) are very similar to those in the closely related acetamidinium cations in [MeC(NH2)2]Cl (Cannon et al., 1975) and [{MeC(NH2)2}2]CO3 (Norrestam, 1984). The bond angles about the central C28 atom [average 120.0 (6)°] are very similar and their sum is ca 360°, as expected for an sp2-carbon. The bond distances C28—N1 [1.306 (4) Å] and C28—N2 [1.311 (4) Å] are statistically equivalent. These bond distances are intermediate between normal Csp2—N single (1.458 Å; Sutton, 1965) and C═N double [1.271 (2) Å; Levine, 1963] bond distances and are similar to those in [{MeC(NH2)2}2]CO3 (Norrestam, 1984). Thus, the π electrons are delocalized over the NCN unit. The NiPr units are normal and the C27 and C30 iPr groups are oriented syn and anti with respect to the C29 Me group [torsion angles: C30—N2—C28—C20 - 176.8 (3)°; C27—N1—C28—C29 0.3 (5)°].
The Ga(C6F5)4- anion adopts a nearly ideal tetrahedral structure. The angles about the Ga atom range between 105.0 (1) (C1—Ga—C13) and 112.8 (1)° (C1—Ga—C19), and thus remain close to the ideal tetrahedral angle of 109.47°. The Ga—C bond lengths [average 2.009 (13) Å] are in excellent agreement with the Ga—C distances in [(Ph3P)2N][Ga(C6F5)4] [average 2.01 (2) Å; Tebbe et al., 1996] and are slightly longer than those in GaPh3 [average 1.957 (16) Å; Malone & McDonald, 1970], probably due to a less electrophilic Ga center in Ga(C6F5)4-.