Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106014429/fg3012sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012Isup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IIsup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IIIsup4.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270106014429/fg3012IVsup5.hkl |
CCDC references: 612433; 612434; 612435; 612436
For the preparation of (I) and (III), to a solution of MnBr2 (215 mg) or HgCl2 (271.5 mg) (1 mmol), respectively, in acetonitrile (aqueous, 15 ml) was added btmgp (270 mg, 1 mmol); the mixture was stirred for 15 min at room temperature and then refluxed for a further 15 min. Colourless crystals were obtained using the vapor pressure equalization method with this solution in the presence of isopropylether. For the preparation of (II), a solution of PtCl2 (266 mg, 1 mmol) in acetonitrile (15 ml) was combined with btmgpg (270 mg, 1 mmol) and the mixture was stirred for 15 min at room temperature. NaBPh4 (342 mg, 1 mmol) was then added and the mixture was stirred for a further 15 min. Colourless crystals were obtained using the vapor pressure equalization method with this solution in the presence of isopropylether. For the preparation of (IV), to a solution of btmgp (270 mg, 1 mmol) in MeCN (10 ml) was added trifluoracetic acid (251 mg, 2.2 mmol) dropwise and the reaction mixture was then refluxed for 1 h. Crystals were grown by slow diffusion of diethylether into the colorless reaction solution.
H atoms were placed at idealized positions and treated as riding on their C atoms, with Uiso(H) values of 1.2Ueq(C) or 1.5Ueq(CH3). All CH3 groups were allowed to rotate but not to tip. The S—O bond geometry of the disordered triflat group in (IV) was been restrained with SADI (SHELXTL) [specify what this means in practice, for the benefit of readers who do not use this software]. Atoms O112–O132 of the minor part [occupation factor 0.081 (4)] were refined isotropically.
For all compounds, data collection: SMART (Bruker, 2002); cell refinement: SMART. Data reduction: SAINT (Bruker, 2002) for (I), (III), (IV); SAINT (Bruker, 2002 for (II). Program(s) used to solve structure: SHELXTL (Bruker, 2002) for (I), (III), (IV); SHELXTL (Bruker, 2002 for (II). For all compounds, program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
C13H32N62+·2Br− | Z = 4 |
Mr = 432.27 | F(000) = 888 |
Triclinic, P1 | Dx = 1.478 Mg m−3 |
a = 12.4256 (14) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.5254 (15) Å | Cell parameters from 3469 reflections |
c = 12.6935 (15) Å | θ = 2.3–24.0° |
α = 79.465 (3)° | µ = 4.18 mm−1 |
β = 89.731 (3)° | T = 120 K |
γ = 89.361 (2)° | Prism, colourless |
V = 1942.1 (4) Å3 | 0.42 × 0.22 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 9242 independent reflections |
Radiation source: sealed tube | 5769 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.065 |
ϕ and ω scans | θmax = 27.9°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −15→16 |
Tmin = 0.243, Tmax = 0.435 | k = −16→16 |
19556 measured reflections | l = −16→16 |
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)] = 0.058 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.044P)2] where P = (Fo2 + 2Fc2)/3 |
9242 reflections | (Δ/σ)max = 0.001 |
387 parameters | Δρmax = 0.95 e Å−3 |
0 restraints | Δρmin = −0.89 e Å−3 |
C13H32N62+·2Br− | γ = 89.361 (2)° |
Mr = 432.27 | V = 1942.1 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 12.4256 (14) Å | Mo Kα radiation |
b = 12.5254 (15) Å | µ = 4.18 mm−1 |
c = 12.6935 (15) Å | T = 120 K |
α = 79.465 (3)° | 0.42 × 0.22 × 0.20 mm |
β = 89.731 (3)° |
Bruker SMART CCD area-detector diffractometer | 9242 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 5769 reflections with I > 2σ(I) |
Tmin = 0.243, Tmax = 0.435 | Rint = 0.065 |
19556 measured reflections |
R[F2 > 2σ(F2)] = 0.058 | 0 restraints |
wR(F2) = 0.139 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.95 e Å−3 |
9242 reflections | Δρmin = −0.89 e Å−3 |
387 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 | ||
Br1 | 0.21776 (5) | 0.65444 (5) | 0.95708 (5) | 0.03482 (17) | |
Br2 | 0.72816 (5) | 0.80904 (4) | 0.70951 (4) | 0.03285 (16) | |
Br3 | 0.22558 (5) | 0.15980 (5) | 0.78783 (4) | 0.03379 (16) | |
Br4 | 0.71426 (4) | 0.33765 (4) | 0.57236 (5) | 0.03097 (15) | |
N11 | 0.3247 (3) | 0.4184 (3) | 0.9363 (3) | 0.0233 (10) | |
H11 | 0.2971 | 0.4842 | 0.9308 | 0.028* | |
N12 | 0.4455 (4) | 0.4830 (4) | 0.8021 (4) | 0.0292 (11) | |
N13 | 0.4859 (3) | 0.3269 (4) | 0.9222 (4) | 0.0271 (10) | |
N14 | 0.1088 (3) | 0.1451 (3) | 1.0304 (3) | 0.0229 (10) | |
H14 | 0.1314 | 0.1377 | 0.9663 | 0.027* | |
N15 | 0.0292 (3) | 0.0492 (3) | 1.1836 (3) | 0.0220 (9) | |
N16 | 0.1701 (3) | −0.0278 (3) | 1.1025 (3) | 0.0245 (10) | |
N21 | 0.8200 (3) | 0.5801 (3) | 0.5462 (4) | 0.0267 (10) | |
H21 | 0.7971 | 0.5132 | 0.5659 | 0.032* | |
N22 | 0.9398 (4) | 0.5614 (4) | 0.6873 (4) | 0.0307 (11) | |
N23 | 0.9751 (4) | 0.6806 (4) | 0.5286 (4) | 0.0307 (11) | |
N24 | 0.6106 (3) | 0.8538 (3) | 0.4642 (3) | 0.0237 (10) | |
H24 | 0.6359 | 0.8539 | 0.5288 | 0.028* | |
N25 | 0.6791 (4) | 1.0246 (3) | 0.4010 (3) | 0.0247 (10) | |
N26 | 0.5286 (3) | 0.9661 (3) | 0.3201 (3) | 0.0232 (10) | |
C11 | 0.0799 (4) | 0.2554 (4) | 1.0469 (4) | 0.0255 (12) | |
H10A | 0.0925 | 0.2609 | 1.1226 | 0.031* | |
H10B | 0.0024 | 0.2692 | 1.0315 | 0.031* | |
C12 | 0.1459 (4) | 0.3401 (4) | 0.9746 (4) | 0.0262 (12) | |
H10C | 0.1338 | 0.3336 | 0.8990 | 0.031* | |
H10D | 0.1212 | 0.4133 | 0.9836 | 0.031* | |
C13 | 0.2647 (4) | 0.3282 (4) | 0.9986 (4) | 0.0272 (12) | |
H10E | 0.2765 | 0.3264 | 1.0760 | 0.033* | |
H10F | 0.2916 | 0.2588 | 0.9813 | 0.033* | |
C14 | 0.4183 (4) | 0.4077 (4) | 0.8872 (4) | 0.0245 (12) | |
C15 | 0.3644 (5) | 0.5479 (5) | 0.7338 (5) | 0.0446 (17) | |
H10G | 0.2951 | 0.5106 | 0.7427 | 0.067* | |
H10H | 0.3872 | 0.5571 | 0.6587 | 0.067* | |
H10I | 0.3568 | 0.6193 | 0.7544 | 0.067* | |
C16 | 0.5574 (5) | 0.5129 (5) | 0.7790 (5) | 0.0397 (15) | |
H10J | 0.6015 | 0.4860 | 0.8422 | 0.060* | |
H10K | 0.5627 | 0.5921 | 0.7605 | 0.060* | |
H10L | 0.5831 | 0.4806 | 0.7187 | 0.060* | |
C17 | 0.5507 (5) | 0.2770 (5) | 0.8485 (5) | 0.0354 (14) | |
H10M | 0.5386 | 0.3157 | 0.7751 | 0.053* | |
H10N | 0.5302 | 0.2009 | 0.8541 | 0.053* | |
H10O | 0.6269 | 0.2808 | 0.8666 | 0.053* | |
C108 | 0.4936 (5) | 0.2740 (5) | 1.0319 (5) | 0.0413 (16) | |
H10P | 0.4668 | 0.3230 | 1.0783 | 0.062* | |
H10Q | 0.5689 | 0.2548 | 1.0493 | 0.062* | |
H10R | 0.4503 | 0.2080 | 1.0431 | 0.062* | |
C19 | 0.1032 (4) | 0.0557 (4) | 1.1058 (4) | 0.0227 (11) | |
C110 | 0.0514 (5) | −0.0090 (4) | 1.2927 (4) | 0.0314 (13) | |
H11A | 0.1266 | −0.0336 | 1.2975 | 0.047* | |
H11B | 0.0041 | −0.0719 | 1.3095 | 0.047* | |
H11C | 0.0383 | 0.0397 | 1.3438 | 0.047* | |
C111 | −0.0762 (4) | 0.1003 (4) | 1.1676 (4) | 0.0276 (12) | |
H11D | −0.0761 | 0.1691 | 1.1940 | 0.041* | |
H11E | −0.1302 | 0.0521 | 1.2070 | 0.041* | |
H11F | −0.0936 | 0.1142 | 1.0911 | 0.041* | |
C112 | 0.2772 (4) | −0.0107 (5) | 1.0539 (5) | 0.0366 (15) | |
H11G | 0.2755 | −0.0261 | 0.9809 | 0.055* | |
H11H | 0.3293 | −0.0594 | 1.0968 | 0.055* | |
H11I | 0.2985 | 0.0649 | 1.0514 | 0.055* | |
C113 | 0.1397 (5) | −0.1404 (4) | 1.1414 (5) | 0.0348 (14) | |
H11J | 0.1747 | −0.1671 | 1.2103 | 0.052* | |
H11K | 0.1626 | −0.1851 | 1.0894 | 0.052* | |
H11L | 0.0614 | −0.1446 | 1.1505 | 0.052* | |
C21 | 0.5752 (4) | 0.7498 (4) | 0.4374 (4) | 0.0249 (12) | |
H20A | 0.5870 | 0.7504 | 0.3601 | 0.030* | |
H20B | 0.4973 | 0.7402 | 0.4526 | 0.030* | |
C22 | 0.6390 (4) | 0.6555 (4) | 0.5040 (4) | 0.0247 (12) | |
H20C | 0.6353 | 0.6617 | 0.5806 | 0.030* | |
H20D | 0.6058 | 0.5859 | 0.4963 | 0.030* | |
C23 | 0.7563 (4) | 0.6550 (4) | 0.4692 (4) | 0.0238 (12) | |
H20E | 0.7612 | 0.6334 | 0.3981 | 0.029* | |
H20F | 0.7856 | 0.7291 | 0.4626 | 0.029* | |
C24 | 0.9108 (4) | 0.6078 (4) | 0.5882 (4) | 0.0261 (12) | |
C25 | 0.8597 (5) | 0.5110 (5) | 0.7638 (5) | 0.0446 (16) | |
H20G | 0.7877 | 0.5249 | 0.7326 | 0.067* | |
H20H | 0.8641 | 0.5416 | 0.8293 | 0.067* | |
H20I | 0.8732 | 0.4325 | 0.7809 | 0.067* | |
C26 | 1.0505 (5) | 0.5475 (5) | 0.7224 (5) | 0.0466 (17) | |
H20J | 1.0980 | 0.5842 | 0.6656 | 0.070* | |
H20K | 1.0688 | 0.4699 | 0.7384 | 0.070* | |
H20L | 1.0598 | 0.5789 | 0.7870 | 0.070* | |
C27 | 1.0312 (5) | 0.7613 (5) | 0.5755 (6) | 0.0486 (18) | |
H20M | 1.0178 | 0.7487 | 0.6529 | 0.073* | |
H20N | 1.0050 | 0.8340 | 0.5431 | 0.073* | |
H20O | 1.1086 | 0.7559 | 0.5621 | 0.073* | |
C28 | 0.9859 (4) | 0.6868 (5) | 0.4150 (4) | 0.0323 (13) | |
H20P | 0.9447 | 0.6285 | 0.3929 | 0.048* | |
H20Q | 1.0620 | 0.6790 | 0.3968 | 0.048* | |
H20R | 0.9585 | 0.7573 | 0.3778 | 0.048* | |
C29 | 0.6058 (4) | 0.9482 (4) | 0.3946 (4) | 0.0204 (11) | |
C210 | 0.7843 (4) | 0.9973 (5) | 0.4470 (4) | 0.0317 (13) | |
H21B | 0.7926 | 0.9182 | 0.4649 | 0.048* | |
H21C | 0.7917 | 1.0282 | 0.5121 | 0.048* | |
H21D | 0.8398 | 1.0271 | 0.3951 | 0.048* | |
C211 | 0.6541 (5) | 1.1411 (4) | 0.3695 (4) | 0.0325 (14) | |
H21E | 0.5813 | 1.1504 | 0.3396 | 0.049* | |
H21F | 0.7060 | 1.1745 | 0.3154 | 0.049* | |
H21G | 0.6583 | 1.1759 | 0.4324 | 0.049* | |
C212 | 0.5470 (5) | 1.0306 (4) | 0.2144 (4) | 0.0304 (13) | |
H21H | 0.6216 | 1.0556 | 0.2090 | 0.046* | |
H21I | 0.4980 | 1.0935 | 0.2032 | 0.046* | |
H21J | 0.5338 | 0.9862 | 0.1598 | 0.046* | |
C213 | 0.4196 (4) | 0.9226 (4) | 0.3411 (4) | 0.0266 (12) | |
H21K | 0.4159 | 0.8807 | 0.4142 | 0.040* | |
H21L | 0.4030 | 0.8753 | 0.2899 | 0.040* | |
H21M | 0.3674 | 0.9827 | 0.3331 | 0.040* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0295 (3) | 0.0298 (3) | 0.0484 (4) | 0.0070 (2) | 0.0001 (3) | −0.0160 (3) |
Br2 | 0.0485 (4) | 0.0283 (3) | 0.0206 (3) | 0.0009 (3) | −0.0074 (3) | −0.0012 (2) |
Br3 | 0.0485 (4) | 0.0341 (3) | 0.0176 (3) | 0.0001 (3) | 0.0074 (3) | −0.0018 (2) |
Br4 | 0.0281 (3) | 0.0258 (3) | 0.0399 (4) | −0.0061 (2) | 0.0014 (3) | −0.0080 (2) |
N11 | 0.028 (2) | 0.015 (2) | 0.025 (2) | 0.0011 (19) | 0.007 (2) | −0.0010 (18) |
N12 | 0.028 (3) | 0.031 (3) | 0.025 (3) | 0.005 (2) | 0.009 (2) | 0.003 (2) |
N13 | 0.024 (2) | 0.028 (2) | 0.026 (3) | 0.003 (2) | 0.003 (2) | 0.002 (2) |
N14 | 0.026 (2) | 0.022 (2) | 0.018 (2) | 0.0038 (19) | 0.0036 (19) | 0.0019 (18) |
N15 | 0.028 (2) | 0.022 (2) | 0.015 (2) | −0.0006 (19) | 0.0037 (19) | −0.0007 (18) |
N16 | 0.028 (2) | 0.022 (2) | 0.022 (2) | 0.0019 (19) | 0.004 (2) | 0.0031 (19) |
N21 | 0.025 (2) | 0.018 (2) | 0.034 (3) | −0.0013 (19) | −0.004 (2) | 0.003 (2) |
N22 | 0.030 (3) | 0.033 (3) | 0.030 (3) | 0.001 (2) | −0.009 (2) | −0.009 (2) |
N23 | 0.026 (3) | 0.028 (3) | 0.041 (3) | −0.005 (2) | 0.000 (2) | −0.016 (2) |
N24 | 0.026 (2) | 0.028 (2) | 0.016 (2) | 0.000 (2) | −0.0003 (19) | 0.0012 (19) |
N25 | 0.031 (3) | 0.020 (2) | 0.020 (2) | −0.003 (2) | −0.002 (2) | 0.0021 (19) |
N26 | 0.026 (2) | 0.026 (2) | 0.016 (2) | −0.0003 (19) | −0.0019 (19) | 0.0007 (18) |
C11 | 0.023 (3) | 0.021 (3) | 0.032 (3) | 0.001 (2) | 0.003 (2) | −0.004 (2) |
C12 | 0.026 (3) | 0.020 (3) | 0.029 (3) | 0.003 (2) | 0.000 (2) | 0.005 (2) |
C13 | 0.025 (3) | 0.027 (3) | 0.028 (3) | −0.003 (2) | 0.003 (2) | 0.002 (2) |
C14 | 0.028 (3) | 0.023 (3) | 0.023 (3) | −0.002 (2) | 0.000 (2) | −0.005 (2) |
C15 | 0.053 (4) | 0.039 (4) | 0.034 (4) | 0.014 (3) | 0.008 (3) | 0.014 (3) |
C16 | 0.047 (4) | 0.037 (3) | 0.035 (4) | −0.011 (3) | 0.015 (3) | −0.007 (3) |
C17 | 0.038 (3) | 0.034 (3) | 0.037 (4) | 0.010 (3) | −0.001 (3) | −0.015 (3) |
C108 | 0.031 (3) | 0.059 (4) | 0.027 (3) | 0.003 (3) | −0.008 (3) | 0.009 (3) |
C19 | 0.022 (3) | 0.029 (3) | 0.016 (3) | −0.004 (2) | −0.002 (2) | 0.000 (2) |
C110 | 0.043 (4) | 0.025 (3) | 0.024 (3) | 0.000 (3) | 0.001 (3) | −0.001 (2) |
C111 | 0.025 (3) | 0.032 (3) | 0.025 (3) | −0.004 (2) | 0.000 (2) | −0.001 (2) |
C112 | 0.033 (3) | 0.044 (4) | 0.029 (3) | 0.014 (3) | 0.001 (3) | 0.004 (3) |
C113 | 0.052 (4) | 0.021 (3) | 0.031 (3) | 0.001 (3) | 0.002 (3) | −0.005 (2) |
C21 | 0.022 (3) | 0.024 (3) | 0.027 (3) | −0.004 (2) | −0.003 (2) | −0.001 (2) |
C22 | 0.025 (3) | 0.027 (3) | 0.021 (3) | −0.003 (2) | −0.002 (2) | 0.001 (2) |
C23 | 0.028 (3) | 0.021 (3) | 0.019 (3) | 0.002 (2) | −0.004 (2) | 0.008 (2) |
C24 | 0.029 (3) | 0.021 (3) | 0.030 (3) | 0.006 (2) | −0.007 (3) | −0.010 (2) |
C25 | 0.056 (4) | 0.044 (4) | 0.030 (4) | 0.004 (3) | −0.003 (3) | 0.002 (3) |
C26 | 0.045 (4) | 0.045 (4) | 0.052 (4) | 0.012 (3) | −0.027 (3) | −0.015 (3) |
C27 | 0.038 (4) | 0.042 (4) | 0.072 (5) | −0.008 (3) | −0.002 (3) | −0.026 (4) |
C28 | 0.026 (3) | 0.039 (3) | 0.031 (3) | −0.001 (3) | 0.001 (3) | −0.003 (3) |
C29 | 0.025 (3) | 0.023 (3) | 0.013 (3) | 0.002 (2) | 0.003 (2) | −0.003 (2) |
C210 | 0.036 (3) | 0.031 (3) | 0.029 (3) | −0.010 (3) | 0.003 (3) | −0.004 (3) |
C211 | 0.045 (4) | 0.019 (3) | 0.033 (3) | −0.007 (3) | 0.005 (3) | −0.001 (2) |
C212 | 0.038 (3) | 0.028 (3) | 0.022 (3) | 0.001 (3) | −0.004 (3) | 0.004 (2) |
C213 | 0.023 (3) | 0.027 (3) | 0.028 (3) | 0.007 (2) | −0.004 (2) | −0.002 (2) |
N11—C14 | 1.333 (6) | C17—H10M | 0.9800 |
N11—C13 | 1.465 (6) | C17—H10N | 0.9800 |
N11—H11 | 0.8800 | C17—H10O | 0.9800 |
N12—C14 | 1.342 (6) | C108—H10P | 0.9800 |
N12—C16 | 1.459 (7) | C108—H10Q | 0.9800 |
N12—C15 | 1.470 (7) | C108—H10R | 0.9800 |
N13—C14 | 1.322 (6) | C110—H11A | 0.9800 |
N13—C108 | 1.432 (7) | C110—H11B | 0.9800 |
N13—C17 | 1.452 (6) | C110—H11C | 0.9800 |
N14—C19 | 1.336 (6) | C111—H11D | 0.9800 |
N14—C11 | 1.475 (6) | C111—H11E | 0.9800 |
N14—H14 | 0.8800 | C111—H11F | 0.9800 |
N15—C19 | 1.339 (6) | C112—H11G | 0.9800 |
N15—C111 | 1.449 (6) | C112—H11H | 0.9800 |
N15—C110 | 1.468 (7) | C112—H11I | 0.9800 |
N16—C19 | 1.335 (6) | C113—H11J | 0.9800 |
N16—C113 | 1.460 (6) | C113—H11K | 0.9800 |
N16—C112 | 1.466 (7) | C113—H11L | 0.9800 |
N21—C24 | 1.326 (7) | C21—C22 | 1.536 (7) |
N21—C23 | 1.455 (6) | C21—H20A | 0.9900 |
N21—H21 | 0.8800 | C21—H20B | 0.9900 |
N22—C24 | 1.335 (7) | C22—C23 | 1.521 (7) |
N22—C26 | 1.447 (7) | C22—H20C | 0.9900 |
N22—C25 | 1.454 (7) | C22—H20D | 0.9900 |
N23—C24 | 1.342 (7) | C23—H20E | 0.9900 |
N23—C28 | 1.435 (7) | C23—H20F | 0.9900 |
N23—C27 | 1.450 (7) | C25—H20G | 0.9800 |
N24—C29 | 1.341 (6) | C25—H20H | 0.9800 |
N24—C21 | 1.477 (6) | C25—H20I | 0.9800 |
N24—H24 | 0.8800 | C26—H20J | 0.9800 |
N25—C29 | 1.341 (6) | C26—H20K | 0.9800 |
N25—C210 | 1.446 (7) | C26—H20L | 0.9800 |
N25—C211 | 1.471 (6) | C27—H20M | 0.9800 |
N26—C29 | 1.339 (6) | C27—H20N | 0.9800 |
N26—C212 | 1.451 (6) | C27—H20O | 0.9800 |
N26—C213 | 1.470 (6) | C28—H20P | 0.9800 |
C11—C12 | 1.516 (7) | C28—H20Q | 0.9800 |
C11—H10A | 0.9900 | C28—H20R | 0.9800 |
C11—H10B | 0.9900 | C210—H21B | 0.9800 |
C12—C13 | 1.509 (7) | C210—H21C | 0.9800 |
C12—H10C | 0.9900 | C210—H21D | 0.9800 |
C12—H10D | 0.9900 | C211—H21E | 0.9800 |
C13—H10E | 0.9900 | C211—H21F | 0.9800 |
C13—H10F | 0.9900 | C211—H21G | 0.9800 |
C15—H10G | 0.9800 | C212—H21H | 0.9800 |
C15—H10H | 0.9800 | C212—H21I | 0.9800 |
C15—H10I | 0.9800 | C212—H21J | 0.9800 |
C16—H10J | 0.9800 | C213—H21K | 0.9800 |
C16—H10K | 0.9800 | C213—H21L | 0.9800 |
C16—H10L | 0.9800 | C213—H21M | 0.9800 |
C14—N11—C13 | 124.5 (4) | N15—C111—H11D | 109.5 |
C14—N11—H11 | 117.7 | N15—C111—H11E | 109.5 |
C13—N11—H11 | 117.7 | H11D—C111—H11E | 109.5 |
C14—N12—C16 | 121.5 (5) | N15—C111—H11F | 109.5 |
C14—N12—C15 | 122.1 (5) | H11D—C111—H11F | 109.5 |
C16—N12—C15 | 116.0 (5) | H11E—C111—H11F | 109.5 |
C14—N13—C108 | 123.9 (5) | N16—C112—H11G | 109.5 |
C14—N13—C17 | 121.4 (4) | N16—C112—H11H | 109.5 |
C108—N13—C17 | 114.4 (4) | H11G—C112—H11H | 109.5 |
C19—N14—C11 | 124.7 (4) | N16—C112—H11I | 109.5 |
C19—N14—H14 | 117.7 | H11G—C112—H11I | 109.5 |
C11—N14—H14 | 117.7 | H11H—C112—H11I | 109.5 |
C19—N15—C111 | 123.1 (4) | N16—C113—H11J | 109.5 |
C19—N15—C110 | 121.4 (4) | N16—C113—H11K | 109.5 |
C111—N15—C110 | 115.5 (4) | H11J—C113—H11K | 109.5 |
C19—N16—C113 | 122.6 (4) | N16—C113—H11L | 109.5 |
C19—N16—C112 | 121.0 (4) | H11J—C113—H11L | 109.5 |
C113—N16—C112 | 116.3 (4) | H11K—C113—H11L | 109.5 |
C24—N21—C23 | 123.2 (4) | N24—C21—C22 | 109.7 (4) |
C24—N21—H21 | 118.4 | N24—C21—H20A | 109.7 |
C23—N21—H21 | 118.4 | C22—C21—H20A | 109.7 |
C24—N22—C26 | 123.7 (5) | N24—C21—H20B | 109.7 |
C24—N22—C25 | 120.3 (5) | C22—C21—H20B | 109.7 |
C26—N22—C25 | 115.7 (5) | H20A—C21—H20B | 108.2 |
C24—N23—C28 | 121.8 (5) | C23—C22—C21 | 111.8 (4) |
C24—N23—C27 | 121.1 (5) | C23—C22—H20C | 109.2 |
C28—N23—C27 | 117.0 (5) | C21—C22—H20C | 109.2 |
C29—N24—C21 | 123.0 (4) | C23—C22—H20D | 109.2 |
C29—N24—H24 | 118.5 | C21—C22—H20D | 109.2 |
C21—N24—H24 | 118.5 | H20C—C22—H20D | 107.9 |
C29—N25—C210 | 121.8 (4) | N21—C23—C22 | 111.0 (4) |
C29—N25—C211 | 121.9 (4) | N21—C23—H20E | 109.4 |
C210—N25—C211 | 116.1 (4) | C22—C23—H20E | 109.4 |
C29—N26—C212 | 122.1 (4) | N21—C23—H20F | 109.4 |
C29—N26—C213 | 121.8 (4) | C22—C23—H20F | 109.4 |
C212—N26—C213 | 116.1 (4) | H20E—C23—H20F | 108.0 |
N14—C11—C12 | 110.9 (4) | N21—C24—N22 | 120.6 (5) |
N14—C11—H10A | 109.5 | N21—C24—N23 | 119.2 (5) |
C12—C11—H10A | 109.5 | N22—C24—N23 | 120.2 (5) |
N14—C11—H10B | 109.5 | N22—C25—H20G | 109.5 |
C12—C11—H10B | 109.5 | N22—C25—H20H | 109.5 |
H10A—C11—H10B | 108.0 | H20G—C25—H20H | 109.5 |
C13—C12—C11 | 112.3 (4) | N22—C25—H20I | 109.5 |
C13—C12—H10C | 109.1 | H20G—C25—H20I | 109.5 |
C11—C12—H10C | 109.1 | H20H—C25—H20I | 109.5 |
C13—C12—H10D | 109.1 | N22—C26—H20J | 109.5 |
C11—C12—H10D | 109.1 | N22—C26—H20K | 109.5 |
H10C—C12—H10D | 107.9 | H20J—C26—H20K | 109.5 |
N11—C13—C12 | 110.9 (4) | N22—C26—H20L | 109.5 |
N11—C13—H10E | 109.5 | H20J—C26—H20L | 109.5 |
C12—C13—H10E | 109.5 | H20K—C26—H20L | 109.5 |
N11—C13—H10F | 109.5 | N23—C27—H20M | 109.5 |
C12—C13—H10F | 109.5 | N23—C27—H20N | 109.5 |
H10E—C13—H10F | 108.0 | H20M—C27—H20N | 109.5 |
N13—C14—N11 | 121.7 (5) | N23—C27—H20O | 109.5 |
N13—C14—N12 | 119.4 (5) | H20M—C27—H20O | 109.5 |
N11—C14—N12 | 118.8 (5) | H20N—C27—H20O | 109.5 |
N12—C15—H10G | 109.5 | N23—C28—H20P | 109.5 |
N12—C15—H10H | 109.5 | N23—C28—H20Q | 109.5 |
H10G—C15—H10H | 109.5 | H20P—C28—H20Q | 109.5 |
N12—C15—H10I | 109.5 | N23—C28—H20R | 109.5 |
H10G—C15—H10I | 109.5 | H20P—C28—H20R | 109.5 |
H10H—C15—H10I | 109.5 | H20Q—C28—H20R | 109.5 |
N12—C16—H10J | 109.5 | N26—C29—N25 | 120.4 (4) |
N12—C16—H10K | 109.5 | N26—C29—N24 | 120.4 (5) |
H10J—C16—H10K | 109.5 | N25—C29—N24 | 119.1 (5) |
N12—C16—H10L | 109.5 | N25—C210—H21B | 109.5 |
H10J—C16—H10L | 109.5 | N25—C210—H21C | 109.5 |
H10K—C16—H10L | 109.5 | H21B—C210—H21C | 109.5 |
N13—C17—H10M | 109.5 | N25—C210—H21D | 109.5 |
N13—C17—H10N | 109.5 | H21B—C210—H21D | 109.5 |
H10M—C17—H10N | 109.5 | H21C—C210—H21D | 109.5 |
N13—C17—H10O | 109.5 | N25—C211—H21E | 109.5 |
H10M—C17—H10O | 109.5 | N25—C211—H21F | 109.5 |
H10N—C17—H10O | 109.5 | H21E—C211—H21F | 109.5 |
N13—C108—H10P | 109.5 | N25—C211—H21G | 109.5 |
N13—C108—H10Q | 109.5 | H21E—C211—H21G | 109.5 |
H10P—C108—H10Q | 109.5 | H21F—C211—H21G | 109.5 |
N13—C108—H10R | 109.5 | N26—C212—H21H | 109.5 |
H10P—C108—H10R | 109.5 | N26—C212—H21I | 109.5 |
H10Q—C108—H10R | 109.5 | H21H—C212—H21I | 109.5 |
N16—C19—N14 | 120.0 (5) | N26—C212—H21J | 109.5 |
N16—C19—N15 | 120.0 (5) | H21H—C212—H21J | 109.5 |
N14—C19—N15 | 119.9 (5) | H21I—C212—H21J | 109.5 |
N15—C110—H11A | 109.5 | N26—C213—H21K | 109.5 |
N15—C110—H11B | 109.5 | N26—C213—H21L | 109.5 |
H11A—C110—H11B | 109.5 | H21K—C213—H21L | 109.5 |
N15—C110—H11C | 109.5 | N26—C213—H21M | 109.5 |
H11A—C110—H11C | 109.5 | H21K—C213—H21M | 109.5 |
H11B—C110—H11C | 109.5 | H21L—C213—H21M | 109.5 |
C19—N14—C11—C12 | 149.9 (5) | C29—N24—C21—C22 | 151.6 (5) |
N14—C11—C12—C13 | −62.8 (6) | N24—C21—C22—C23 | −69.7 (5) |
C14—N11—C13—C12 | −137.5 (5) | C24—N21—C23—C22 | −128.9 (5) |
C11—C12—C13—N11 | −173.4 (4) | C21—C22—C23—N21 | 168.3 (4) |
C108—N13—C14—N11 | −28.2 (8) | C23—N21—C24—N22 | 148.8 (5) |
C17—N13—C14—N11 | 144.8 (5) | C23—N21—C24—N23 | −33.4 (7) |
C108—N13—C14—N12 | 149.7 (5) | C26—N22—C24—N21 | 151.5 (5) |
C17—N13—C14—N12 | −37.3 (8) | C25—N22—C24—N21 | −21.9 (8) |
C13—N11—C14—N13 | −27.4 (8) | C26—N22—C24—N23 | −26.3 (8) |
C13—N11—C14—N12 | 154.7 (5) | C25—N22—C24—N23 | 160.3 (5) |
C16—N12—C14—N13 | −30.8 (8) | C28—N23—C24—N21 | −34.2 (7) |
C15—N12—C14—N13 | 155.8 (5) | C27—N23—C24—N21 | 141.5 (5) |
C16—N12—C14—N11 | 147.2 (5) | C28—N23—C24—N22 | 143.7 (5) |
C15—N12—C14—N11 | −26.3 (8) | C27—N23—C24—N22 | −40.6 (7) |
C113—N16—C19—N14 | −148.1 (5) | C212—N26—C29—N25 | 34.1 (7) |
C112—N16—C19—N14 | 28.6 (7) | C213—N26—C29—N25 | −145.2 (5) |
C113—N16—C19—N15 | 30.6 (8) | C212—N26—C29—N24 | −146.3 (5) |
C112—N16—C19—N15 | −152.6 (5) | C213—N26—C29—N24 | 34.4 (7) |
C11—N14—C19—N16 | −150.9 (5) | C210—N25—C29—N26 | −155.0 (5) |
C11—N14—C19—N15 | 30.4 (7) | C211—N25—C29—N26 | 29.9 (7) |
C111—N15—C19—N16 | −146.1 (5) | C210—N25—C29—N24 | 25.4 (7) |
C110—N15—C19—N16 | 35.4 (7) | C211—N25—C29—N24 | −149.7 (5) |
C111—N15—C19—N14 | 32.7 (7) | C21—N24—C29—N26 | 31.1 (7) |
C110—N15—C19—N14 | −145.8 (5) | C21—N24—C29—N25 | −149.2 (5) |
C13H32N62+·BC24H20−·Cl− | F(000) = 1352 |
Mr = 627.11 | Dx = 1.175 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 17.5770 (8) Å | Cell parameters from 2888 reflections |
b = 9.3797 (4) Å | θ = 2.4–18.6° |
c = 22.4953 (10) Å | µ = 0.14 mm−1 |
β = 107.034 (1)° | T = 150 K |
V = 3546.0 (3) Å3 | Prism, colourless |
Z = 4 | 0.20 × 0.20 × 0.15 mm |
Bruker SMART CCD area-detector diffractometer | 7800 independent reflections |
Radiation source: sealed tube | 4307 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.100 |
ϕ and ω scans | θmax = 27.1°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −22→22 |
Tmin = 0.962, Tmax = 0.975 | k = −11→12 |
39279 measured reflections | l = −28→28 |
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)] = 0.044 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.91 | w = 1/[σ2(Fo2) + (0.014P)2] where P = (Fo2 + 2Fc2)/3 |
7800 reflections | (Δ/σ)max < 0.001 |
414 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.24 e Å−3 |
C13H32N62+·BC24H20−·Cl− | V = 3546.0 (3) Å3 |
Mr = 627.11 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 17.5770 (8) Å | µ = 0.14 mm−1 |
b = 9.3797 (4) Å | T = 150 K |
c = 22.4953 (10) Å | 0.20 × 0.20 × 0.15 mm |
β = 107.034 (1)° |
Bruker SMART CCD area-detector diffractometer | 7800 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4307 reflections with I > 2σ(I) |
Tmin = 0.962, Tmax = 0.975 | Rint = 0.100 |
39279 measured reflections |
R[F2 > 2σ(F2)] = 0.044 | 0 restraints |
wR(F2) = 0.072 | H-atom parameters constrained |
S = 0.91 | Δρmax = 0.21 e Å−3 |
7800 reflections | Δρmin = −0.24 e Å−3 |
414 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 | ||
N1 | 0.42981 (10) | 0.28118 (18) | 0.46007 (8) | 0.0351 (5) | |
H1 | 0.4663 | 0.2682 | 0.4959 | 0.042* | |
N2 | 0.39148 (10) | 0.46334 (18) | 0.38800 (8) | 0.0324 (5) | |
N3 | 0.51865 (11) | 0.3681 (2) | 0.41167 (8) | 0.0349 (5) | |
N4 | 0.27589 (10) | −0.08128 (17) | 0.44950 (8) | 0.0310 (5) | |
H4 | 0.3199 | −0.1098 | 0.4420 | 0.037* | |
N5 | 0.19748 (10) | −0.17014 (19) | 0.35619 (8) | 0.0359 (5) | |
N6 | 0.14914 (10) | −0.16326 (19) | 0.44150 (8) | 0.0385 (5) | |
C1 | 0.28268 (12) | 0.0262 (2) | 0.49847 (10) | 0.0373 (6) | |
H1A | 0.2862 | −0.0219 | 0.5384 | 0.045* | |
H1B | 0.2348 | 0.0876 | 0.4876 | 0.045* | |
C2 | 0.35624 (12) | 0.1168 (2) | 0.50548 (9) | 0.0365 (6) | |
H2A | 0.3624 | 0.1826 | 0.5410 | 0.044* | |
H2B | 0.4035 | 0.0538 | 0.5155 | 0.044* | |
C3 | 0.35448 (12) | 0.2030 (2) | 0.44868 (10) | 0.0389 (6) | |
H3A | 0.3471 | 0.1390 | 0.4124 | 0.047* | |
H3B | 0.3094 | 0.2709 | 0.4395 | 0.047* | |
C4 | 0.44636 (14) | 0.3709 (2) | 0.41930 (10) | 0.0310 (6) | |
C5 | 0.33170 (12) | 0.5223 (2) | 0.41415 (10) | 0.0433 (7) | |
H5A | 0.2796 | 0.4811 | 0.3928 | 0.065* | |
H5B | 0.3295 | 0.6260 | 0.4087 | 0.065* | |
H5C | 0.3457 | 0.4993 | 0.4585 | 0.065* | |
C6 | 0.38698 (12) | 0.5152 (2) | 0.32517 (9) | 0.0406 (6) | |
H6A | 0.4052 | 0.6143 | 0.3277 | 0.061* | |
H6B | 0.3318 | 0.5097 | 0.2986 | 0.061* | |
H6C | 0.4209 | 0.4560 | 0.3075 | 0.061* | |
C7 | 0.55731 (13) | 0.4953 (2) | 0.39588 (10) | 0.0481 (7) | |
H7A | 0.5585 | 0.4885 | 0.3527 | 0.072* | |
H7B | 0.6118 | 0.5018 | 0.4236 | 0.072* | |
H7C | 0.5275 | 0.5804 | 0.4009 | 0.072* | |
C8 | 0.56775 (12) | 0.2378 (2) | 0.42332 (10) | 0.0455 (7) | |
H8A | 0.6072 | 0.2441 | 0.4643 | 0.068* | |
H8B | 0.5951 | 0.2282 | 0.3913 | 0.068* | |
H8C | 0.5336 | 0.1546 | 0.4221 | 0.068* | |
C9 | 0.20744 (13) | −0.1379 (2) | 0.41590 (10) | 0.0313 (6) | |
C10 | 0.14601 (13) | −0.2857 (2) | 0.32397 (10) | 0.0537 (7) | |
H10A | 0.1311 | −0.3457 | 0.3544 | 0.080* | |
H10B | 0.1745 | −0.3433 | 0.3010 | 0.080* | |
H10C | 0.0980 | −0.2454 | 0.2948 | 0.080* | |
C11 | 0.24061 (12) | −0.0948 (2) | 0.31912 (9) | 0.0435 (7) | |
H11A | 0.2597 | −0.0031 | 0.3387 | 0.065* | |
H11B | 0.2050 | −0.0784 | 0.2772 | 0.065* | |
H11C | 0.2861 | −0.1525 | 0.3166 | 0.065* | |
C12 | 0.06523 (12) | −0.1435 (3) | 0.40782 (10) | 0.0612 (8) | |
H12A | 0.0604 | −0.1053 | 0.3663 | 0.092* | |
H12B | 0.0413 | −0.0765 | 0.4306 | 0.092* | |
H12C | 0.0376 | −0.2353 | 0.4039 | 0.092* | |
C13 | 0.16501 (13) | −0.1997 (2) | 0.50729 (10) | 0.0464 (7) | |
H13A | 0.2201 | −0.2327 | 0.5239 | 0.070* | |
H13B | 0.1286 | −0.2755 | 0.5116 | 0.070* | |
H13C | 0.1569 | −0.1153 | 0.5304 | 0.070* | |
B1 | 0.21730 (15) | 0.3271 (3) | 0.16740 (11) | 0.0309 (7) | |
C21 | 0.18802 (13) | 0.2673 (2) | 0.09559 (10) | 0.0330 (6) | |
C22 | 0.12074 (13) | 0.3196 (2) | 0.05074 (11) | 0.0403 (6) | |
H22A | 0.0948 | 0.4008 | 0.0610 | 0.048* | |
C23 | 0.08974 (15) | 0.2601 (3) | −0.00755 (11) | 0.0541 (8) | |
H23A | 0.0433 | 0.2993 | −0.0358 | 0.065* | |
C24 | 0.12665 (17) | 0.1432 (3) | −0.02460 (12) | 0.0575 (8) | |
H24A | 0.1056 | 0.1005 | −0.0643 | 0.069* | |
C25 | 0.19407 (16) | 0.0902 (3) | 0.01685 (12) | 0.0520 (7) | |
H25A | 0.2210 | 0.0119 | 0.0053 | 0.062* | |
C26 | 0.22329 (13) | 0.1497 (2) | 0.07537 (11) | 0.0427 (6) | |
H26A | 0.2695 | 0.1089 | 0.1033 | 0.051* | |
C31 | 0.30882 (13) | 0.2744 (2) | 0.20032 (10) | 0.0316 (6) | |
C32 | 0.33150 (14) | 0.1843 (2) | 0.25210 (10) | 0.0405 (6) | |
H32A | 0.2914 | 0.1518 | 0.2694 | 0.049* | |
C33 | 0.40888 (14) | 0.1395 (2) | 0.27968 (10) | 0.0439 (7) | |
H33A | 0.4205 | 0.0771 | 0.3144 | 0.053* | |
C34 | 0.46928 (14) | 0.1862 (2) | 0.25633 (11) | 0.0442 (7) | |
H34A | 0.5228 | 0.1575 | 0.2753 | 0.053* | |
C35 | 0.45049 (13) | 0.2747 (2) | 0.20524 (11) | 0.0404 (6) | |
H35A | 0.4912 | 0.3087 | 0.1889 | 0.049* | |
C36 | 0.37226 (13) | 0.3142 (2) | 0.17769 (10) | 0.0362 (6) | |
H36A | 0.3607 | 0.3717 | 0.1413 | 0.043* | |
C41 | 0.20919 (13) | 0.5022 (2) | 0.16739 (9) | 0.0320 (6) | |
C42 | 0.13468 (14) | 0.5671 (3) | 0.15916 (9) | 0.0394 (6) | |
H42A | 0.0899 | 0.5081 | 0.1567 | 0.047* | |
C43 | 0.12370 (15) | 0.7132 (3) | 0.15444 (10) | 0.0481 (7) | |
H43A | 0.0720 | 0.7517 | 0.1483 | 0.058* | |
C44 | 0.18657 (17) | 0.8031 (3) | 0.15854 (10) | 0.0511 (8) | |
H44A | 0.1786 | 0.9032 | 0.1542 | 0.061* | |
C45 | 0.26113 (16) | 0.7457 (3) | 0.16905 (10) | 0.0462 (7) | |
H45A | 0.3058 | 0.8063 | 0.1736 | 0.055* | |
C46 | 0.27127 (14) | 0.5986 (2) | 0.17307 (9) | 0.0369 (6) | |
H46A | 0.3235 | 0.5617 | 0.1801 | 0.044* | |
C51 | 0.15780 (13) | 0.2591 (2) | 0.20472 (11) | 0.0367 (6) | |
C52 | 0.16064 (15) | 0.3079 (3) | 0.26397 (11) | 0.0567 (8) | |
H52A | 0.1963 | 0.3830 | 0.2817 | 0.068* | |
C53 | 0.11353 (18) | 0.2513 (3) | 0.29831 (13) | 0.0728 (10) | |
H53A | 0.1172 | 0.2881 | 0.3384 | 0.087* | |
C54 | 0.06193 (17) | 0.1428 (3) | 0.27406 (15) | 0.0679 (10) | |
H54A | 0.0295 | 0.1037 | 0.2971 | 0.081* | |
C55 | 0.05733 (14) | 0.0907 (3) | 0.21622 (13) | 0.0559 (8) | |
H55A | 0.0220 | 0.0146 | 0.1991 | 0.067* | |
C56 | 0.10453 (13) | 0.1495 (2) | 0.18263 (11) | 0.0416 (6) | |
H56A | 0.0999 | 0.1125 | 0.1424 | 0.050* | |
Cl1 | 0.43748 (3) | −0.14939 (6) | 0.41987 (2) | 0.03828 (16) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0331 (12) | 0.0424 (13) | 0.0266 (12) | −0.0070 (10) | 0.0040 (9) | 0.0067 (10) |
N2 | 0.0349 (12) | 0.0325 (12) | 0.0293 (12) | 0.0054 (10) | 0.0086 (10) | 0.0055 (10) |
N3 | 0.0331 (12) | 0.0399 (13) | 0.0330 (12) | −0.0017 (11) | 0.0115 (10) | 0.0043 (10) |
N4 | 0.0251 (11) | 0.0365 (12) | 0.0317 (12) | −0.0012 (9) | 0.0090 (9) | −0.0074 (10) |
N5 | 0.0339 (12) | 0.0427 (13) | 0.0296 (12) | −0.0061 (10) | 0.0070 (10) | −0.0037 (11) |
N6 | 0.0310 (12) | 0.0521 (14) | 0.0332 (12) | −0.0070 (11) | 0.0106 (10) | 0.0006 (11) |
C1 | 0.0415 (15) | 0.0382 (16) | 0.0370 (15) | −0.0089 (12) | 0.0188 (13) | −0.0103 (12) |
C2 | 0.0404 (15) | 0.0395 (16) | 0.0315 (14) | −0.0093 (12) | 0.0134 (12) | −0.0048 (12) |
C3 | 0.0333 (15) | 0.0384 (16) | 0.0424 (16) | −0.0044 (12) | 0.0070 (13) | 0.0076 (13) |
C4 | 0.0352 (15) | 0.0315 (15) | 0.0259 (14) | −0.0031 (13) | 0.0084 (12) | −0.0015 (12) |
C5 | 0.0495 (17) | 0.0375 (16) | 0.0471 (17) | 0.0114 (13) | 0.0208 (14) | 0.0047 (13) |
C6 | 0.0488 (16) | 0.0448 (16) | 0.0268 (14) | 0.0024 (13) | 0.0088 (12) | 0.0095 (12) |
C7 | 0.0416 (16) | 0.0597 (18) | 0.0417 (16) | −0.0103 (14) | 0.0101 (13) | 0.0095 (14) |
C8 | 0.0397 (16) | 0.0541 (18) | 0.0447 (17) | 0.0131 (14) | 0.0154 (13) | 0.0088 (14) |
C9 | 0.0272 (14) | 0.0334 (15) | 0.0333 (15) | 0.0005 (12) | 0.0087 (12) | 0.0005 (12) |
C10 | 0.0561 (18) | 0.0546 (18) | 0.0435 (17) | −0.0175 (15) | 0.0040 (14) | −0.0110 (14) |
C11 | 0.0447 (16) | 0.0575 (18) | 0.0282 (14) | −0.0009 (13) | 0.0104 (13) | 0.0031 (13) |
C12 | 0.0311 (16) | 0.091 (2) | 0.0625 (19) | −0.0051 (16) | 0.0146 (14) | −0.0030 (17) |
C13 | 0.0542 (17) | 0.0488 (17) | 0.0421 (17) | −0.0106 (13) | 0.0234 (14) | 0.0011 (13) |
B1 | 0.0339 (16) | 0.0346 (18) | 0.0266 (16) | 0.0028 (14) | 0.0123 (13) | 0.0014 (13) |
C21 | 0.0336 (15) | 0.0344 (15) | 0.0359 (15) | −0.0024 (12) | 0.0180 (12) | 0.0048 (12) |
C22 | 0.0403 (16) | 0.0444 (17) | 0.0387 (16) | −0.0044 (13) | 0.0154 (13) | −0.0041 (14) |
C23 | 0.0554 (19) | 0.066 (2) | 0.0382 (18) | −0.0106 (16) | 0.0090 (15) | 0.0011 (15) |
C24 | 0.076 (2) | 0.064 (2) | 0.0350 (17) | −0.0249 (18) | 0.0209 (16) | −0.0140 (16) |
C25 | 0.065 (2) | 0.0458 (18) | 0.055 (2) | −0.0095 (15) | 0.0320 (17) | −0.0142 (16) |
C26 | 0.0469 (17) | 0.0423 (17) | 0.0424 (17) | 0.0001 (14) | 0.0186 (14) | 0.0000 (14) |
C31 | 0.0407 (15) | 0.0311 (15) | 0.0268 (14) | 0.0004 (12) | 0.0157 (12) | −0.0028 (11) |
C32 | 0.0416 (16) | 0.0446 (17) | 0.0383 (16) | 0.0015 (13) | 0.0165 (13) | 0.0055 (13) |
C33 | 0.0522 (17) | 0.0429 (17) | 0.0347 (15) | 0.0121 (15) | 0.0095 (14) | 0.0081 (13) |
C34 | 0.0402 (16) | 0.0481 (18) | 0.0419 (17) | 0.0142 (14) | 0.0083 (14) | −0.0044 (14) |
C35 | 0.0371 (16) | 0.0465 (17) | 0.0411 (16) | 0.0012 (13) | 0.0167 (13) | −0.0042 (13) |
C36 | 0.0410 (15) | 0.0415 (16) | 0.0269 (14) | 0.0047 (13) | 0.0111 (12) | −0.0011 (12) |
C41 | 0.0346 (15) | 0.0415 (16) | 0.0205 (13) | 0.0044 (13) | 0.0090 (11) | 0.0032 (12) |
C42 | 0.0424 (17) | 0.0472 (17) | 0.0308 (15) | 0.0032 (14) | 0.0140 (13) | −0.0051 (13) |
C43 | 0.0549 (19) | 0.054 (2) | 0.0373 (16) | 0.0226 (16) | 0.0172 (14) | −0.0001 (15) |
C44 | 0.082 (2) | 0.0392 (18) | 0.0376 (16) | 0.0151 (17) | 0.0263 (17) | 0.0029 (13) |
C45 | 0.0633 (19) | 0.0419 (18) | 0.0390 (17) | −0.0021 (15) | 0.0235 (15) | −0.0019 (14) |
C46 | 0.0439 (16) | 0.0381 (16) | 0.0303 (15) | 0.0051 (13) | 0.0135 (12) | −0.0005 (12) |
C51 | 0.0366 (15) | 0.0393 (16) | 0.0367 (16) | 0.0102 (13) | 0.0146 (13) | 0.0082 (13) |
C52 | 0.064 (2) | 0.066 (2) | 0.0505 (19) | 0.0014 (16) | 0.0328 (16) | 0.0018 (16) |
C53 | 0.092 (3) | 0.081 (3) | 0.067 (2) | 0.025 (2) | 0.056 (2) | 0.016 (2) |
C54 | 0.061 (2) | 0.077 (3) | 0.085 (3) | 0.0296 (19) | 0.051 (2) | 0.045 (2) |
C55 | 0.0409 (17) | 0.053 (2) | 0.077 (2) | 0.0099 (14) | 0.0228 (17) | 0.0283 (17) |
C56 | 0.0352 (15) | 0.0437 (17) | 0.0503 (17) | 0.0119 (14) | 0.0194 (13) | 0.0151 (14) |
Cl1 | 0.0310 (3) | 0.0503 (4) | 0.0335 (3) | 0.0043 (3) | 0.0093 (3) | 0.0010 (3) |
N1—C4 | 1.338 (2) | C13—H13C | 0.9800 |
N1—C3 | 1.469 (2) | B1—C31 | 1.638 (3) |
N1—H1 | 0.8800 | B1—C21 | 1.644 (3) |
N2—C4 | 1.334 (2) | B1—C41 | 1.649 (3) |
N2—C5 | 1.455 (2) | B1—C51 | 1.649 (3) |
N2—C6 | 1.475 (2) | C21—C22 | 1.399 (3) |
N3—C4 | 1.331 (2) | C21—C26 | 1.405 (3) |
N3—C7 | 1.467 (2) | C22—C23 | 1.382 (3) |
N3—C8 | 1.474 (2) | C22—H22A | 0.9500 |
N4—C9 | 1.330 (2) | C23—C24 | 1.385 (3) |
N4—C1 | 1.472 (2) | C23—H23A | 0.9500 |
N4—H4 | 0.8800 | C24—C25 | 1.369 (3) |
N5—C9 | 1.338 (2) | C24—H24A | 0.9500 |
N5—C10 | 1.461 (2) | C25—C26 | 1.383 (3) |
N5—C11 | 1.463 (2) | C25—H25A | 0.9500 |
N6—C9 | 1.336 (2) | C26—H26A | 0.9500 |
N6—C12 | 1.459 (2) | C31—C32 | 1.399 (3) |
N6—C13 | 1.464 (2) | C31—C36 | 1.405 (3) |
C1—C2 | 1.517 (2) | C32—C33 | 1.384 (3) |
C1—H1A | 0.9900 | C32—H32A | 0.9500 |
C1—H1B | 0.9900 | C33—C34 | 1.386 (3) |
C2—C3 | 1.504 (2) | C33—H33A | 0.9500 |
C2—H2A | 0.9900 | C34—C35 | 1.378 (3) |
C2—H2B | 0.9900 | C34—H34A | 0.9500 |
C3—H3A | 0.9900 | C35—C36 | 1.383 (3) |
C3—H3B | 0.9900 | C35—H35A | 0.9500 |
C5—H5A | 0.9800 | C36—H36A | 0.9500 |
C5—H5B | 0.9800 | C41—C46 | 1.394 (3) |
C5—H5C | 0.9800 | C41—C42 | 1.406 (3) |
C6—H6A | 0.9800 | C42—C43 | 1.384 (3) |
C6—H6B | 0.9800 | C42—H42A | 0.9500 |
C6—H6C | 0.9800 | C43—C44 | 1.372 (3) |
C7—H7A | 0.9800 | C43—H43A | 0.9500 |
C7—H7B | 0.9800 | C44—C45 | 1.372 (3) |
C7—H7C | 0.9800 | C44—H44A | 0.9500 |
C8—H8A | 0.9800 | C45—C46 | 1.391 (3) |
C8—H8B | 0.9800 | C45—H45A | 0.9500 |
C8—H8C | 0.9800 | C46—H46A | 0.9500 |
C10—H10A | 0.9800 | C51—C56 | 1.381 (3) |
C10—H10B | 0.9800 | C51—C52 | 1.396 (3) |
C10—H10C | 0.9800 | C52—C53 | 1.392 (3) |
C11—H11A | 0.9800 | C52—H52A | 0.9500 |
C11—H11B | 0.9800 | C53—C54 | 1.367 (3) |
C11—H11C | 0.9800 | C53—H53A | 0.9500 |
C12—H12A | 0.9800 | C54—C55 | 1.370 (3) |
C12—H12B | 0.9800 | C54—H54A | 0.9500 |
C12—H12C | 0.9800 | C55—C56 | 1.390 (3) |
C13—H13A | 0.9800 | C55—H55A | 0.9500 |
C13—H13B | 0.9800 | C56—H56A | 0.9500 |
C4—N1—C3 | 124.07 (18) | N6—C13—H13A | 109.5 |
C4—N1—H1 | 118.0 | N6—C13—H13B | 109.5 |
C3—N1—H1 | 118.0 | H13A—C13—H13B | 109.5 |
C4—N2—C5 | 121.97 (18) | N6—C13—H13C | 109.5 |
C4—N2—C6 | 123.20 (19) | H13A—C13—H13C | 109.5 |
C5—N2—C6 | 114.82 (17) | H13B—C13—H13C | 109.5 |
C4—N3—C7 | 122.9 (2) | C31—B1—C21 | 108.95 (18) |
C4—N3—C8 | 121.63 (19) | C31—B1—C41 | 111.97 (19) |
C7—N3—C8 | 115.36 (17) | C21—B1—C41 | 109.74 (18) |
C9—N4—C1 | 124.08 (18) | C31—B1—C51 | 109.79 (18) |
C9—N4—H4 | 118.0 | C21—B1—C51 | 107.79 (18) |
C1—N4—H4 | 118.0 | C41—B1—C51 | 108.51 (18) |
C9—N5—C10 | 123.09 (19) | C22—C21—C26 | 113.7 (2) |
C9—N5—C11 | 121.74 (19) | C22—C21—B1 | 123.0 (2) |
C10—N5—C11 | 115.12 (17) | C26—C21—B1 | 123.0 (2) |
C9—N6—C12 | 122.68 (19) | C23—C22—C21 | 123.9 (2) |
C9—N6—C13 | 122.30 (19) | C23—C22—H22A | 118.0 |
C12—N6—C13 | 114.77 (17) | C21—C22—H22A | 118.0 |
N4—C1—C2 | 109.97 (17) | C22—C23—C24 | 119.7 (2) |
N4—C1—H1A | 109.7 | C22—C23—H23A | 120.1 |
C2—C1—H1A | 109.7 | C24—C23—H23A | 120.1 |
N4—C1—H1B | 109.7 | C25—C24—C23 | 118.8 (2) |
C2—C1—H1B | 109.7 | C25—C24—H24A | 120.6 |
H1A—C1—H1B | 108.2 | C23—C24—H24A | 120.6 |
C3—C2—C1 | 114.08 (18) | C24—C25—C26 | 120.5 (2) |
C3—C2—H2A | 108.7 | C24—C25—H25A | 119.7 |
C1—C2—H2A | 108.7 | C26—C25—H25A | 119.7 |
C3—C2—H2B | 108.7 | C25—C26—C21 | 123.3 (2) |
C1—C2—H2B | 108.7 | C25—C26—H26A | 118.3 |
H2A—C2—H2B | 107.6 | C21—C26—H26A | 118.3 |
N1—C3—C2 | 109.07 (17) | C32—C31—C36 | 113.5 (2) |
N1—C3—H3A | 109.9 | C32—C31—B1 | 124.1 (2) |
C2—C3—H3A | 109.9 | C36—C31—B1 | 122.3 (2) |
N1—C3—H3B | 109.9 | C33—C32—C31 | 124.0 (2) |
C2—C3—H3B | 109.9 | C33—C32—H32A | 118.0 |
H3A—C3—H3B | 108.3 | C31—C32—H32A | 118.0 |
N3—C4—N2 | 121.0 (2) | C32—C33—C34 | 119.7 (2) |
N3—C4—N1 | 118.9 (2) | C32—C33—H33A | 120.2 |
N2—C4—N1 | 120.1 (2) | C34—C33—H33A | 120.2 |
N2—C5—H5A | 109.5 | C35—C34—C33 | 118.9 (2) |
N2—C5—H5B | 109.5 | C35—C34—H34A | 120.5 |
H5A—C5—H5B | 109.5 | C33—C34—H34A | 120.5 |
N2—C5—H5C | 109.5 | C34—C35—C36 | 120.0 (2) |
H5A—C5—H5C | 109.5 | C34—C35—H35A | 120.0 |
H5B—C5—H5C | 109.5 | C36—C35—H35A | 120.0 |
N2—C6—H6A | 109.5 | C35—C36—C31 | 123.8 (2) |
N2—C6—H6B | 109.5 | C35—C36—H36A | 118.1 |
H6A—C6—H6B | 109.5 | C31—C36—H36A | 118.1 |
N2—C6—H6C | 109.5 | C46—C41—C42 | 113.9 (2) |
H6A—C6—H6C | 109.5 | C46—C41—B1 | 125.5 (2) |
H6B—C6—H6C | 109.5 | C42—C41—B1 | 120.6 (2) |
N3—C7—H7A | 109.5 | C43—C42—C41 | 122.8 (2) |
N3—C7—H7B | 109.5 | C43—C42—H42A | 118.6 |
H7A—C7—H7B | 109.5 | C41—C42—H42A | 118.6 |
N3—C7—H7C | 109.5 | C44—C43—C42 | 120.8 (2) |
H7A—C7—H7C | 109.5 | C44—C43—H43A | 119.6 |
H7B—C7—H7C | 109.5 | C42—C43—H43A | 119.6 |
N3—C8—H8A | 109.5 | C43—C44—C45 | 118.7 (2) |
N3—C8—H8B | 109.5 | C43—C44—H44A | 120.7 |
H8A—C8—H8B | 109.5 | C45—C44—H44A | 120.7 |
N3—C8—H8C | 109.5 | C44—C45—C46 | 119.9 (2) |
H8A—C8—H8C | 109.5 | C44—C45—H45A | 120.0 |
H8B—C8—H8C | 109.5 | C46—C45—H45A | 120.0 |
N4—C9—N6 | 120.5 (2) | C45—C46—C41 | 123.7 (2) |
N4—C9—N5 | 119.4 (2) | C45—C46—H46A | 118.1 |
N6—C9—N5 | 120.1 (2) | C41—C46—H46A | 118.1 |
N5—C10—H10A | 109.5 | C56—C51—C52 | 114.7 (2) |
N5—C10—H10B | 109.5 | C56—C51—B1 | 124.7 (2) |
H10A—C10—H10B | 109.5 | C52—C51—B1 | 120.6 (2) |
N5—C10—H10C | 109.5 | C53—C52—C51 | 123.0 (3) |
H10A—C10—H10C | 109.5 | C53—C52—H52A | 118.5 |
H10B—C10—H10C | 109.5 | C51—C52—H52A | 118.5 |
N5—C11—H11A | 109.5 | C54—C53—C52 | 119.7 (3) |
N5—C11—H11B | 109.5 | C54—C53—H53A | 120.1 |
H11A—C11—H11B | 109.5 | C52—C53—H53A | 120.1 |
N5—C11—H11C | 109.5 | C53—C54—C55 | 119.5 (3) |
H11A—C11—H11C | 109.5 | C53—C54—H54A | 120.3 |
H11B—C11—H11C | 109.5 | C55—C54—H54A | 120.3 |
N6—C12—H12A | 109.5 | C54—C55—C56 | 119.8 (3) |
N6—C12—H12B | 109.5 | C54—C55—H55A | 120.1 |
H12A—C12—H12B | 109.5 | C56—C55—H55A | 120.1 |
N6—C12—H12C | 109.5 | C51—C56—C55 | 123.4 (2) |
H12A—C12—H12C | 109.5 | C51—C56—H56A | 118.3 |
H12B—C12—H12C | 109.5 | C55—C56—H56A | 118.3 |
C9—N4—C1—C2 | −153.0 (2) | C51—B1—C31—C32 | 0.4 (3) |
N4—C1—C2—C3 | 63.4 (2) | C21—B1—C31—C36 | 61.2 (3) |
C4—N1—C3—C2 | −178.05 (19) | C41—B1—C31—C36 | −60.4 (3) |
C1—C2—C3—N1 | −177.63 (17) | C51—B1—C31—C36 | 179.01 (19) |
C7—N3—C4—N2 | 30.5 (3) | C36—C31—C32—C33 | 1.1 (3) |
C8—N3—C4—N2 | −154.25 (19) | B1—C31—C32—C33 | 179.7 (2) |
C7—N3—C4—N1 | −148.08 (19) | C31—C32—C33—C34 | 0.9 (4) |
C8—N3—C4—N1 | 27.2 (3) | C32—C33—C34—C35 | −1.1 (3) |
C5—N2—C4—N3 | −148.0 (2) | C33—C34—C35—C36 | −0.8 (3) |
C6—N2—C4—N3 | 31.2 (3) | C34—C35—C36—C31 | 3.0 (3) |
C5—N2—C4—N1 | 30.6 (3) | C32—C31—C36—C35 | −3.0 (3) |
C6—N2—C4—N1 | −150.21 (19) | B1—C31—C36—C35 | 178.3 (2) |
C3—N1—C4—N3 | −138.4 (2) | C31—B1—C41—C46 | 21.6 (3) |
C3—N1—C4—N2 | 43.0 (3) | C21—B1—C41—C46 | −99.5 (2) |
C1—N4—C9—N6 | −35.6 (3) | C51—B1—C41—C46 | 142.9 (2) |
C1—N4—C9—N5 | 144.8 (2) | C31—B1—C41—C42 | −160.61 (19) |
C12—N6—C9—N4 | 143.0 (2) | C21—B1—C41—C42 | 78.3 (2) |
C13—N6—C9—N4 | −30.9 (3) | C51—B1—C41—C42 | −39.3 (3) |
C12—N6—C9—N5 | −37.4 (3) | C46—C41—C42—C43 | 2.7 (3) |
C13—N6—C9—N5 | 148.7 (2) | B1—C41—C42—C43 | −175.4 (2) |
C10—N5—C9—N4 | 150.6 (2) | C41—C42—C43—C44 | −0.9 (4) |
C11—N5—C9—N4 | −26.8 (3) | C42—C43—C44—C45 | −1.7 (4) |
C10—N5—C9—N6 | −29.0 (3) | C43—C44—C45—C46 | 2.3 (3) |
C11—N5—C9—N6 | 153.6 (2) | C44—C45—C46—C41 | −0.4 (4) |
C31—B1—C21—C22 | −164.8 (2) | C42—C41—C46—C45 | −2.0 (3) |
C41—B1—C21—C22 | −41.9 (3) | B1—C41—C46—C45 | 175.9 (2) |
C51—B1—C21—C22 | 76.1 (3) | C31—B1—C51—C56 | −106.4 (2) |
C31—B1—C21—C26 | 21.9 (3) | C21—B1—C51—C56 | 12.2 (3) |
C41—B1—C21—C26 | 144.8 (2) | C41—B1—C51—C56 | 131.0 (2) |
C51—B1—C21—C26 | −97.2 (2) | C31—B1—C51—C52 | 71.2 (3) |
C26—C21—C22—C23 | 1.7 (3) | C21—B1—C51—C52 | −170.2 (2) |
B1—C21—C22—C23 | −172.2 (2) | C41—B1—C51—C52 | −51.4 (3) |
C21—C22—C23—C24 | −1.1 (4) | C56—C51—C52—C53 | −0.2 (4) |
C22—C23—C24—C25 | −0.8 (4) | B1—C51—C52—C53 | −178.0 (2) |
C23—C24—C25—C26 | 2.0 (4) | C51—C52—C53—C54 | 0.3 (4) |
C24—C25—C26—C21 | −1.4 (4) | C52—C53—C54—C55 | 0.1 (4) |
C22—C21—C26—C25 | −0.5 (3) | C53—C54—C55—C56 | −0.6 (4) |
B1—C21—C26—C25 | 173.4 (2) | C52—C51—C56—C55 | −0.3 (3) |
C21—B1—C31—C32 | −117.4 (2) | B1—C51—C56—C55 | 177.4 (2) |
C41—B1—C31—C32 | 121.0 (2) | C54—C55—C56—C51 | 0.7 (4) |
(C13H32N6)[HgCl4] | F(000) = 1200 |
Mr = 614.84 | Dx = 1.772 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.3199 (4) Å | Cell parameters from 6011 reflections |
b = 18.0809 (9) Å | θ = 2.5–28.2° |
c = 15.8086 (8) Å | µ = 7.15 mm−1 |
β = 104.291 (1)° | T = 120 K |
V = 2304.5 (2) Å3 | Plate, colourless |
Z = 4 | 0.45 × 0.20 × 0.08 mm |
Bruker SMART CCD area-detector diffractometer | 5049 independent reflections |
Radiation source: sealed tube | 4421 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
ϕ and ω scans | θmax = 27.1°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.133, Tmax = 0.563 | k = −23→23 |
23407 measured reflections | l = −20→20 |
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)] = 0.028 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.0523P)2 + 4.0796P] where P = (Fo2 + 2Fc2)/3 |
5049 reflections | (Δ/σ)max = 0.001 |
225 parameters | Δρmax = 0.92 e Å−3 |
0 restraints | Δρmin = −0.55 e Å−3 |
(C13H32N6)[HgCl4] | V = 2304.5 (2) Å3 |
Mr = 614.84 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.3199 (4) Å | µ = 7.15 mm−1 |
b = 18.0809 (9) Å | T = 120 K |
c = 15.8086 (8) Å | 0.45 × 0.20 × 0.08 mm |
β = 104.291 (1)° |
Bruker SMART CCD area-detector diffractometer | 5049 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4421 reflections with I > 2σ(I) |
Tmin = 0.133, Tmax = 0.563 | Rint = 0.025 |
23407 measured reflections |
R[F2 > 2σ(F2)] = 0.028 | 0 restraints |
wR(F2) = 0.087 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.92 e Å−3 |
5049 reflections | Δρmin = −0.55 e Å−3 |
225 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 | ||
Hg1 | 1.036601 (19) | 0.373597 (8) | 0.214262 (10) | 0.02617 (7) | |
Cl1 | 0.86299 (14) | 0.48923 (6) | 0.18001 (7) | 0.0339 (2) | |
Cl2 | 1.14518 (12) | 0.37532 (5) | 0.37664 (6) | 0.0248 (2) | |
Cl3 | 1.22766 (13) | 0.37896 (5) | 0.11823 (7) | 0.0261 (2) | |
Cl4 | 0.86451 (13) | 0.25760 (5) | 0.17265 (7) | 0.0289 (2) | |
N1 | 0.6484 (4) | 0.23573 (17) | 0.3237 (2) | 0.0248 (7) | |
H1 | 0.7073 | 0.2313 | 0.2848 | 0.030* | |
N2 | 0.5293 (5) | 0.1627 (2) | 0.4125 (3) | 0.0300 (8) | |
N3 | 0.8064 (4) | 0.1476 (2) | 0.4122 (2) | 0.0262 (7) | |
N4 | 0.6288 (4) | 0.50641 (18) | 0.3130 (2) | 0.0266 (7) | |
H4 | 0.7061 | 0.5076 | 0.2838 | 0.032* | |
N5 | 0.7383 (5) | 0.61109 (19) | 0.3881 (2) | 0.0285 (8) | |
N6 | 0.4587 (4) | 0.58261 (19) | 0.3707 (2) | 0.0263 (7) | |
C1 | 0.5328 (5) | 0.4381 (2) | 0.3095 (3) | 0.0265 (8) | |
H1A | 0.4512 | 0.4344 | 0.2523 | 0.032* | |
H1B | 0.4712 | 0.4390 | 0.3556 | 0.032* | |
C2 | 0.6468 (5) | 0.37128 (19) | 0.3224 (3) | 0.0273 (9) | |
H2A | 0.7282 | 0.3745 | 0.3797 | 0.033* | |
H2B | 0.7084 | 0.3700 | 0.2763 | 0.033* | |
C3 | 0.5433 (5) | 0.3014 (2) | 0.3184 (3) | 0.0273 (9) | |
H3A | 0.4886 | 0.3012 | 0.3674 | 0.033* | |
H3B | 0.4559 | 0.3005 | 0.2631 | 0.033* | |
C4 | 0.6616 (5) | 0.1820 (2) | 0.3832 (3) | 0.0212 (7) | |
C5 | 0.3603 (5) | 0.1678 (3) | 0.3563 (4) | 0.0410 (12) | |
H5A | 0.3047 | 0.2113 | 0.3728 | 0.061* | |
H5B | 0.2981 | 0.1231 | 0.3633 | 0.061* | |
H5C | 0.3654 | 0.1724 | 0.2952 | 0.061* | |
C6 | 0.5423 (8) | 0.1371 (3) | 0.5008 (4) | 0.0486 (14) | |
H6A | 0.5147 | 0.0843 | 0.4997 | 0.073* | |
H6B | 0.4650 | 0.1650 | 0.5264 | 0.073* | |
H6C | 0.6558 | 0.1446 | 0.5359 | 0.073* | |
C7 | 0.9620 (5) | 0.1810 (3) | 0.4051 (3) | 0.0385 (11) | |
H7A | 0.9885 | 0.1642 | 0.3511 | 0.058* | |
H7B | 1.0511 | 0.1663 | 0.4553 | 0.058* | |
H7C | 0.9510 | 0.2350 | 0.4040 | 0.058* | |
C8 | 0.8199 (6) | 0.0695 (2) | 0.4390 (3) | 0.0366 (10) | |
H8A | 0.8619 | 0.0664 | 0.5025 | 0.055* | |
H8B | 0.8964 | 0.0439 | 0.4107 | 0.055* | |
H8C | 0.7103 | 0.0462 | 0.4217 | 0.055* | |
C9 | 0.6074 (5) | 0.5668 (2) | 0.3570 (3) | 0.0229 (8) | |
C10 | 0.9072 (6) | 0.5854 (3) | 0.4011 (4) | 0.0406 (11) | |
H10A | 0.9102 | 0.5314 | 0.4075 | 0.061* | |
H10B | 0.9765 | 0.6080 | 0.4540 | 0.061* | |
H10C | 0.9495 | 0.5992 | 0.3507 | 0.061* | |
C11 | 0.7193 (7) | 0.6914 (2) | 0.3980 (3) | 0.0404 (11) | |
H11A | 0.6041 | 0.7056 | 0.3716 | 0.061* | |
H11B | 0.7933 | 0.7178 | 0.3688 | 0.061* | |
H11C | 0.7477 | 0.7041 | 0.4602 | 0.061* | |
C12 | 0.3039 (5) | 0.5650 (2) | 0.3066 (3) | 0.0306 (9) | |
H12A | 0.3286 | 0.5499 | 0.2516 | 0.046* | |
H12B | 0.2322 | 0.6088 | 0.2966 | 0.046* | |
H12C | 0.2474 | 0.5246 | 0.3288 | 0.046* | |
C13 | 0.4409 (7) | 0.6150 (3) | 0.4525 (3) | 0.0385 (11) | |
H13A | 0.5488 | 0.6150 | 0.4951 | 0.058* | |
H13B | 0.3616 | 0.5858 | 0.4752 | 0.058* | |
H13C | 0.4005 | 0.6659 | 0.4421 | 0.058* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Hg1 | 0.02870 (11) | 0.02320 (10) | 0.02870 (11) | 0.00034 (5) | 0.01107 (7) | 0.00050 (6) |
Cl1 | 0.0446 (6) | 0.0258 (5) | 0.0391 (6) | 0.0137 (4) | 0.0256 (5) | 0.0080 (4) |
Cl2 | 0.0216 (4) | 0.0353 (5) | 0.0152 (4) | −0.0062 (3) | 0.0005 (3) | 0.0059 (3) |
Cl3 | 0.0270 (5) | 0.0277 (5) | 0.0267 (5) | 0.0012 (4) | 0.0124 (4) | −0.0012 (4) |
Cl4 | 0.0346 (5) | 0.0182 (4) | 0.0397 (6) | −0.0100 (4) | 0.0201 (4) | −0.0065 (4) |
N1 | 0.0264 (17) | 0.0196 (15) | 0.0316 (18) | 0.0034 (13) | 0.0133 (14) | 0.0028 (14) |
N2 | 0.0288 (18) | 0.0281 (18) | 0.038 (2) | −0.0035 (14) | 0.0182 (16) | −0.0002 (15) |
N3 | 0.0267 (18) | 0.0230 (15) | 0.0297 (18) | 0.0013 (14) | 0.0084 (14) | 0.0049 (14) |
N4 | 0.0312 (18) | 0.0185 (15) | 0.0354 (19) | −0.0042 (13) | 0.0182 (15) | −0.0038 (14) |
N5 | 0.033 (2) | 0.0211 (16) | 0.0322 (19) | −0.0057 (14) | 0.0096 (16) | −0.0048 (14) |
N6 | 0.0275 (18) | 0.0264 (17) | 0.0249 (17) | 0.0045 (14) | 0.0063 (14) | −0.0031 (14) |
C1 | 0.025 (2) | 0.0179 (18) | 0.036 (2) | −0.0026 (15) | 0.0076 (17) | −0.0002 (16) |
C2 | 0.024 (2) | 0.0205 (19) | 0.039 (2) | −0.0010 (14) | 0.0113 (18) | −0.0018 (16) |
C3 | 0.022 (2) | 0.0161 (17) | 0.044 (2) | 0.0026 (14) | 0.0095 (17) | 0.0015 (17) |
C4 | 0.0253 (19) | 0.0159 (16) | 0.0242 (19) | −0.0034 (14) | 0.0094 (15) | −0.0046 (14) |
C5 | 0.024 (2) | 0.030 (2) | 0.071 (4) | −0.0076 (17) | 0.015 (2) | −0.006 (2) |
C6 | 0.061 (4) | 0.049 (3) | 0.048 (3) | −0.002 (2) | 0.037 (3) | 0.005 (2) |
C7 | 0.023 (2) | 0.044 (3) | 0.046 (3) | 0.0007 (19) | 0.0041 (19) | 0.012 (2) |
C8 | 0.046 (3) | 0.029 (2) | 0.036 (2) | 0.0087 (19) | 0.013 (2) | 0.0085 (19) |
C9 | 0.029 (2) | 0.0195 (17) | 0.0208 (18) | −0.0003 (15) | 0.0083 (15) | 0.0020 (15) |
C10 | 0.030 (2) | 0.040 (3) | 0.053 (3) | −0.006 (2) | 0.012 (2) | −0.008 (2) |
C11 | 0.057 (3) | 0.021 (2) | 0.041 (3) | −0.006 (2) | 0.009 (2) | −0.0041 (19) |
C12 | 0.029 (2) | 0.028 (2) | 0.032 (2) | 0.0060 (17) | 0.0023 (18) | −0.0005 (18) |
C13 | 0.039 (3) | 0.048 (3) | 0.029 (2) | 0.011 (2) | 0.010 (2) | −0.008 (2) |
Hg1—Cl3 | 2.4561 (10) | C2—H2B | 0.9900 |
Hg1—Cl2 | 2.5023 (9) | C3—H3A | 0.9900 |
Hg1—Cl1 | 2.5228 (10) | C3—H3B | 0.9900 |
Hg1—Cl4 | 2.5331 (9) | C5—H5A | 0.9800 |
N1—C4 | 1.338 (5) | C5—H5B | 0.9800 |
N1—C3 | 1.464 (5) | C5—H5C | 0.9800 |
N1—H1 | 0.8800 | C6—H6A | 0.9800 |
N2—C4 | 1.341 (5) | C6—H6B | 0.9800 |
N2—C6 | 1.449 (7) | C6—H6C | 0.9800 |
N2—C5 | 1.469 (6) | C7—H7A | 0.9800 |
N3—C4 | 1.333 (5) | C7—H7B | 0.9800 |
N3—C7 | 1.458 (6) | C7—H7C | 0.9800 |
N3—C8 | 1.470 (5) | C8—H8A | 0.9800 |
N4—C9 | 1.330 (5) | C8—H8B | 0.9800 |
N4—C1 | 1.465 (5) | C8—H8C | 0.9800 |
N4—H4 | 0.8800 | C10—H10A | 0.9800 |
N5—C9 | 1.344 (5) | C10—H10B | 0.9800 |
N5—C10 | 1.446 (6) | C10—H10C | 0.9800 |
N5—C11 | 1.473 (5) | C11—H11A | 0.9800 |
N6—C9 | 1.338 (5) | C11—H11B | 0.9800 |
N6—C13 | 1.460 (6) | C11—H11C | 0.9800 |
N6—C12 | 1.463 (5) | C12—H12A | 0.9800 |
C1—C2 | 1.517 (5) | C12—H12B | 0.9800 |
C1—H1A | 0.9900 | C12—H12C | 0.9800 |
C1—H1B | 0.9900 | C13—H13A | 0.9800 |
C2—C3 | 1.522 (5) | C13—H13B | 0.9800 |
C2—H2A | 0.9900 | C13—H13C | 0.9800 |
Cl3—Hg1—Cl2 | 120.58 (3) | N2—C5—H5C | 109.5 |
Cl3—Hg1—Cl1 | 104.96 (3) | H5A—C5—H5C | 109.5 |
Cl2—Hg1—Cl1 | 104.62 (3) | H5B—C5—H5C | 109.5 |
Cl3—Hg1—Cl4 | 106.43 (3) | N2—C6—H6A | 109.5 |
Cl2—Hg1—Cl4 | 108.33 (3) | N2—C6—H6B | 109.5 |
Cl1—Hg1—Cl4 | 111.93 (4) | H6A—C6—H6B | 109.5 |
C4—N1—C3 | 125.0 (3) | N2—C6—H6C | 109.5 |
C4—N1—H1 | 117.5 | H6A—C6—H6C | 109.5 |
C3—N1—H1 | 117.5 | H6B—C6—H6C | 109.5 |
C4—N2—C6 | 122.9 (4) | N3—C7—H7A | 109.5 |
C4—N2—C5 | 121.3 (4) | N3—C7—H7B | 109.5 |
C6—N2—C5 | 115.8 (4) | H7A—C7—H7B | 109.5 |
C4—N3—C7 | 121.7 (3) | N3—C7—H7C | 109.5 |
C4—N3—C8 | 123.0 (4) | H7A—C7—H7C | 109.5 |
C7—N3—C8 | 114.5 (4) | H7B—C7—H7C | 109.5 |
C9—N4—C1 | 124.7 (3) | N3—C8—H8A | 109.5 |
C9—N4—H4 | 117.6 | N3—C8—H8B | 109.5 |
C1—N4—H4 | 117.6 | H8A—C8—H8B | 109.5 |
C9—N5—C10 | 122.1 (4) | N3—C8—H8C | 109.5 |
C9—N5—C11 | 121.8 (4) | H8A—C8—H8C | 109.5 |
C10—N5—C11 | 115.4 (4) | H8B—C8—H8C | 109.5 |
C9—N6—C13 | 121.9 (4) | N4—C9—N6 | 120.5 (4) |
C9—N6—C12 | 122.2 (4) | N4—C9—N5 | 118.7 (4) |
C13—N6—C12 | 115.8 (4) | N6—C9—N5 | 120.8 (4) |
N4—C1—C2 | 110.5 (3) | N5—C10—H10A | 109.5 |
N4—C1—H1A | 109.6 | N5—C10—H10B | 109.5 |
C2—C1—H1A | 109.6 | H10A—C10—H10B | 109.5 |
N4—C1—H1B | 109.6 | N5—C10—H10C | 109.5 |
C2—C1—H1B | 109.6 | H10A—C10—H10C | 109.5 |
H1A—C1—H1B | 108.1 | H10B—C10—H10C | 109.5 |
C1—C2—C3 | 109.1 (3) | N5—C11—H11A | 109.5 |
C1—C2—H2A | 109.9 | N5—C11—H11B | 109.5 |
C3—C2—H2A | 109.9 | H11A—C11—H11B | 109.5 |
C1—C2—H2B | 109.9 | N5—C11—H11C | 109.5 |
C3—C2—H2B | 109.9 | H11A—C11—H11C | 109.5 |
H2A—C2—H2B | 108.3 | H11B—C11—H11C | 109.5 |
N1—C3—C2 | 110.3 (3) | N6—C12—H12A | 109.5 |
N1—C3—H3A | 109.6 | N6—C12—H12B | 109.5 |
C2—C3—H3A | 109.6 | H12A—C12—H12B | 109.5 |
N1—C3—H3B | 109.6 | N6—C12—H12C | 109.5 |
C2—C3—H3B | 109.6 | H12A—C12—H12C | 109.5 |
H3A—C3—H3B | 108.1 | H12B—C12—H12C | 109.5 |
N3—C4—N1 | 119.4 (3) | N6—C13—H13A | 109.5 |
N3—C4—N2 | 120.6 (4) | N6—C13—H13B | 109.5 |
N1—C4—N2 | 120.0 (4) | H13A—C13—H13B | 109.5 |
N2—C5—H5A | 109.5 | N6—C13—H13C | 109.5 |
N2—C5—H5B | 109.5 | H13A—C13—H13C | 109.5 |
H5A—C5—H5B | 109.5 | H13B—C13—H13C | 109.5 |
C9—N4—C1—C2 | −134.8 (4) | C6—N2—C4—N1 | −147.2 (4) |
N4—C1—C2—C3 | −180.0 (3) | C5—N2—C4—N1 | 31.7 (6) |
C4—N1—C3—C2 | 123.8 (4) | C1—N4—C9—N6 | −28.8 (6) |
C1—C2—C3—N1 | 175.5 (3) | C1—N4—C9—N5 | 150.6 (4) |
C7—N3—C4—N1 | 21.0 (6) | C13—N6—C9—N4 | 142.5 (4) |
C8—N3—C4—N1 | −148.1 (4) | C12—N6—C9—N4 | −34.2 (6) |
C7—N3—C4—N2 | −159.7 (4) | C13—N6—C9—N5 | −36.9 (6) |
C8—N3—C4—N2 | 31.3 (6) | C12—N6—C9—N5 | 146.4 (4) |
C3—N1—C4—N3 | −146.2 (4) | C10—N5—C9—N4 | −20.6 (6) |
C3—N1—C4—N2 | 34.5 (6) | C11—N5—C9—N4 | 149.7 (4) |
C6—N2—C4—N3 | 33.4 (6) | C10—N5—C9—N6 | 158.8 (4) |
C5—N2—C4—N3 | −147.7 (4) | C11—N5—C9—N6 | −30.9 (6) |
C13H32N62+·2CF3O3S− | Z = 2 |
Mr = 570.59 | F(000) = 596 |
Triclinic, P1 | Dx = 1.468 Mg m−3 |
a = 8.8771 (7) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 12.3802 (10) Å | Cell parameters from 3136 reflections |
c = 12.5704 (10) Å | θ = 2.7–28.2° |
α = 108.939 (2)° | µ = 0.29 mm−1 |
β = 91.478 (2)° | T = 120 K |
γ = 97.775 (2)° | Prism, colourless |
V = 1291.10 (18) Å3 | 0.40 × 0.20 × 0.20 mm |
Bruker SMART CCD area-detector diffractometer | 5165 independent reflections |
Radiation source: sealed tube | 4404 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.012 |
ϕ and ω scans | θmax = 26.4°, θmin = 1.7° |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | h = −10→10 |
Tmin = 0.893, Tmax = 0.944 | k = −15→13 |
7636 measured reflections | l = −15→15 |
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)] = 0.046 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0574P)2 + 0.8973P] where P = (Fo2 + 2Fc2)/3 |
5165 reflections | (Δ/σ)max = 0.001 |
337 parameters | Δρmax = 0.76 e Å−3 |
30 restraints | Δρmin = −0.51 e Å−3 |
C13H32N62+·2CF3O3S− | γ = 97.775 (2)° |
Mr = 570.59 | V = 1291.10 (18) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.8771 (7) Å | Mo Kα radiation |
b = 12.3802 (10) Å | µ = 0.29 mm−1 |
c = 12.5704 (10) Å | T = 120 K |
α = 108.939 (2)° | 0.40 × 0.20 × 0.20 mm |
β = 91.478 (2)° |
Bruker SMART CCD area-detector diffractometer | 5165 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2002) | 4404 reflections with I > 2σ(I) |
Tmin = 0.893, Tmax = 0.944 | Rint = 0.012 |
7636 measured reflections |
R[F2 > 2σ(F2)] = 0.046 | 30 restraints |
wR(F2) = 0.121 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.76 e Å−3 |
5165 reflections | Δρmin = −0.51 e Å−3 |
337 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 | Occ. (<1) | |
N1 | 0.34134 (19) | 0.72040 (15) | 1.04886 (14) | 0.0264 (4) | |
H1 | 0.4392 | 0.7341 | 1.0397 | 0.032* | |
N2 | 0.3600 (2) | 0.89892 (15) | 1.18526 (15) | 0.0314 (4) | |
N3 | 0.1719 (2) | 0.75124 (15) | 1.18943 (14) | 0.0262 (4) | |
N4 | 0.2747 (2) | 0.50063 (14) | 0.64499 (14) | 0.0253 (4) | |
H4 | 0.2940 | 0.5611 | 0.6226 | 0.030* | |
N5 | 0.3539 (2) | 0.32301 (15) | 0.61862 (14) | 0.0263 (4) | |
N6 | 0.29202 (19) | 0.37788 (15) | 0.46531 (14) | 0.0256 (4) | |
C1 | 0.2109 (2) | 0.51825 (18) | 0.75437 (16) | 0.0253 (4) | |
H1A | 0.2114 | 0.4478 | 0.7753 | 0.030* | |
H1B | 0.1037 | 0.5309 | 0.7483 | 0.030* | |
C2 | 0.3003 (2) | 0.62071 (18) | 0.84611 (16) | 0.0264 (4) | |
H2A | 0.2843 | 0.6931 | 0.8329 | 0.032* | |
H2B | 0.4104 | 0.6152 | 0.8435 | 0.032* | |
C3 | 0.2498 (2) | 0.62388 (18) | 0.96128 (17) | 0.0261 (4) | |
H3A | 0.1407 | 0.6328 | 0.9652 | 0.031* | |
H3B | 0.2620 | 0.5504 | 0.9735 | 0.031* | |
C4 | 0.2902 (2) | 0.78947 (17) | 1.14127 (16) | 0.0241 (4) | |
C5 | 0.3764 (3) | 0.9599 (2) | 1.30678 (19) | 0.0427 (6) | |
H5A | 0.3112 | 1.0204 | 1.3255 | 0.064* | |
H5B | 0.4829 | 0.9951 | 1.3297 | 0.064* | |
H5C | 0.3460 | 0.9052 | 1.3467 | 0.064* | |
C6 | 0.4434 (3) | 0.9577 (2) | 1.1161 (2) | 0.0425 (6) | |
H6A | 0.5507 | 0.9472 | 1.1188 | 0.064* | |
H6B | 0.4361 | 1.0403 | 1.1452 | 0.064* | |
H6C | 0.3994 | 0.9251 | 1.0380 | 0.064* | |
C7 | 0.0641 (3) | 0.8258 (2) | 1.24782 (19) | 0.0369 (5) | |
H7A | 0.0773 | 0.8395 | 1.3290 | 0.055* | |
H7B | −0.0403 | 0.7880 | 1.2197 | 0.055* | |
H7C | 0.0830 | 0.8996 | 1.2338 | 0.055* | |
C8 | 0.1391 (3) | 0.63118 (19) | 1.18482 (18) | 0.0297 (5) | |
H8A | 0.0533 | 0.5910 | 1.1292 | 0.045* | |
H8B | 0.1128 | 0.6283 | 1.2592 | 0.045* | |
H8C | 0.2292 | 0.5935 | 1.1630 | 0.045* | |
C9 | 0.3058 (2) | 0.40031 (17) | 0.57669 (16) | 0.0227 (4) | |
C10 | 0.3075 (3) | 0.19908 (18) | 0.5662 (2) | 0.0342 (5) | |
H10A | 0.2269 | 0.1845 | 0.5062 | 0.051* | |
H10B | 0.2691 | 0.1659 | 0.6230 | 0.051* | |
H10C | 0.3952 | 0.1633 | 0.5339 | 0.051* | |
C11 | 0.4550 (3) | 0.3572 (2) | 0.72119 (19) | 0.0358 (5) | |
H11A | 0.4925 | 0.4403 | 0.7443 | 0.054* | |
H11B | 0.5415 | 0.3143 | 0.7068 | 0.054* | |
H11C | 0.3989 | 0.3402 | 0.7814 | 0.054* | |
C12 | 0.3864 (3) | 0.3047 (2) | 0.38821 (19) | 0.0348 (5) | |
H12A | 0.4688 | 0.2888 | 0.4317 | 0.052* | |
H12B | 0.4301 | 0.3444 | 0.3377 | 0.052* | |
H12C | 0.3235 | 0.2317 | 0.3436 | 0.052* | |
C13 | 0.1949 (3) | 0.4367 (2) | 0.41384 (18) | 0.0353 (5) | |
H13A | 0.1132 | 0.4615 | 0.4629 | 0.053* | |
H13B | 0.1502 | 0.3836 | 0.3403 | 0.053* | |
H13C | 0.2561 | 0.5043 | 0.4039 | 0.053* | |
S1 | 0.76527 (6) | 0.69756 (5) | 0.96309 (5) | 0.03179 (15) | |
C100 | 0.8910 (3) | 0.8115 (3) | 0.9361 (3) | 0.0486 (7) | |
F11 | 0.9936 (2) | 0.7646 (2) | 0.8635 (2) | 0.0868 (7) | |
F12 | 0.9659 (3) | 0.88298 (18) | 1.02531 (18) | 0.0987 (9) | |
F13 | 0.8205 (2) | 0.86858 (16) | 0.88394 (17) | 0.0724 (5) | |
O111 | 0.6642 (2) | 0.7586 (2) | 1.0382 (2) | 0.0607 (8) | 0.919 (4) |
O121 | 0.6959 (2) | 0.62478 (17) | 0.85468 (16) | 0.0489 (6) | 0.919 (4) |
O131 | 0.8665 (2) | 0.64456 (18) | 1.01468 (19) | 0.0484 (6) | 0.919 (4) |
O112 | 0.6299 (18) | 0.7489 (18) | 0.9535 (17) | 0.044 (6)* | 0.081 (4) |
O122 | 0.816 (2) | 0.6321 (16) | 0.8617 (11) | 0.041 (6)* | 0.081 (4) |
O132 | 0.803 (2) | 0.6881 (17) | 1.0651 (11) | 0.033 (5)* | 0.081 (4) |
S2 | 0.17814 (6) | 0.76156 (5) | 0.53805 (5) | 0.03020 (15) | |
C200 | 0.1155 (3) | 0.8926 (2) | 0.6276 (2) | 0.0350 (5) | |
F21 | 0.2206 (2) | 0.95589 (15) | 0.70753 (15) | 0.0679 (5) | |
F22 | 0.0816 (2) | 0.95771 (13) | 0.56757 (15) | 0.0602 (5) | |
F23 | −0.00844 (18) | 0.86972 (14) | 0.67687 (14) | 0.0552 (4) | |
O21 | 0.3050 (2) | 0.80330 (19) | 0.48704 (17) | 0.0551 (5) | |
O22 | 0.2170 (2) | 0.70685 (16) | 0.61753 (15) | 0.0500 (5) | |
O23 | 0.0464 (2) | 0.70365 (15) | 0.46297 (14) | 0.0418 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0222 (9) | 0.0289 (9) | 0.0235 (9) | 0.0023 (7) | 0.0040 (7) | 0.0028 (7) |
N2 | 0.0416 (11) | 0.0242 (9) | 0.0255 (9) | 0.0017 (8) | 0.0036 (8) | 0.0054 (7) |
N3 | 0.0279 (9) | 0.0284 (9) | 0.0218 (8) | 0.0080 (7) | 0.0055 (7) | 0.0058 (7) |
N4 | 0.0333 (10) | 0.0222 (8) | 0.0204 (8) | 0.0053 (7) | 0.0035 (7) | 0.0065 (7) |
N5 | 0.0291 (9) | 0.0239 (9) | 0.0249 (9) | 0.0053 (7) | −0.0025 (7) | 0.0066 (7) |
N6 | 0.0270 (9) | 0.0295 (9) | 0.0200 (8) | 0.0082 (7) | 0.0022 (7) | 0.0062 (7) |
C1 | 0.0242 (10) | 0.0294 (11) | 0.0221 (10) | 0.0051 (8) | 0.0051 (8) | 0.0074 (8) |
C2 | 0.0283 (11) | 0.0269 (10) | 0.0222 (10) | 0.0041 (8) | 0.0048 (8) | 0.0055 (8) |
C3 | 0.0275 (11) | 0.0263 (10) | 0.0215 (10) | 0.0031 (8) | 0.0036 (8) | 0.0041 (8) |
C4 | 0.0271 (10) | 0.0260 (10) | 0.0201 (9) | 0.0077 (8) | 0.0003 (8) | 0.0073 (8) |
C5 | 0.0593 (16) | 0.0305 (12) | 0.0283 (12) | 0.0007 (11) | −0.0005 (11) | −0.0012 (10) |
C6 | 0.0558 (16) | 0.0298 (12) | 0.0420 (14) | 0.0001 (11) | 0.0097 (12) | 0.0139 (11) |
C7 | 0.0371 (13) | 0.0464 (14) | 0.0276 (11) | 0.0174 (11) | 0.0101 (10) | 0.0079 (10) |
C8 | 0.0336 (12) | 0.0321 (11) | 0.0231 (10) | −0.0004 (9) | 0.0026 (8) | 0.0107 (9) |
C9 | 0.0196 (9) | 0.0239 (10) | 0.0226 (10) | 0.0011 (7) | 0.0005 (7) | 0.0060 (8) |
C10 | 0.0390 (13) | 0.0241 (11) | 0.0375 (12) | 0.0043 (9) | −0.0017 (10) | 0.0082 (9) |
C11 | 0.0397 (13) | 0.0373 (13) | 0.0306 (11) | 0.0102 (10) | −0.0082 (10) | 0.0105 (10) |
C12 | 0.0366 (12) | 0.0409 (13) | 0.0275 (11) | 0.0131 (10) | 0.0103 (9) | 0.0086 (10) |
C13 | 0.0448 (13) | 0.0416 (13) | 0.0228 (10) | 0.0167 (10) | 0.0010 (9) | 0.0112 (10) |
S1 | 0.0251 (3) | 0.0356 (3) | 0.0316 (3) | 0.0029 (2) | 0.0009 (2) | 0.0077 (2) |
C100 | 0.0388 (14) | 0.0597 (17) | 0.0605 (17) | 0.0046 (12) | −0.0004 (13) | 0.0392 (15) |
F11 | 0.0624 (12) | 0.1195 (18) | 0.1062 (17) | 0.0239 (12) | 0.0419 (12) | 0.0685 (15) |
F12 | 0.1292 (19) | 0.0778 (14) | 0.0791 (14) | −0.0664 (14) | −0.0509 (13) | 0.0495 (12) |
F13 | 0.0958 (14) | 0.0634 (11) | 0.0745 (12) | 0.0187 (10) | −0.0074 (11) | 0.0436 (10) |
O111 | 0.0406 (12) | 0.0610 (14) | 0.0651 (17) | 0.0042 (10) | 0.0237 (11) | −0.0003 (12) |
O121 | 0.0482 (14) | 0.0470 (12) | 0.0416 (11) | 0.0025 (9) | −0.0093 (9) | 0.0041 (9) |
O131 | 0.0465 (12) | 0.0444 (12) | 0.0587 (14) | −0.0010 (9) | −0.0132 (10) | 0.0272 (11) |
S2 | 0.0341 (3) | 0.0321 (3) | 0.0294 (3) | 0.0132 (2) | 0.0067 (2) | 0.0135 (2) |
C200 | 0.0383 (13) | 0.0298 (12) | 0.0367 (12) | 0.0075 (9) | −0.0005 (10) | 0.0098 (10) |
F21 | 0.0664 (11) | 0.0522 (10) | 0.0622 (11) | 0.0032 (8) | −0.0204 (9) | −0.0078 (8) |
F22 | 0.0847 (12) | 0.0393 (9) | 0.0687 (11) | 0.0252 (8) | 0.0038 (9) | 0.0280 (8) |
F23 | 0.0544 (10) | 0.0588 (10) | 0.0526 (9) | 0.0204 (8) | 0.0262 (8) | 0.0125 (8) |
O21 | 0.0384 (10) | 0.0788 (14) | 0.0585 (12) | 0.0166 (9) | 0.0200 (9) | 0.0327 (11) |
O22 | 0.0749 (13) | 0.0427 (10) | 0.0431 (10) | 0.0295 (9) | 0.0026 (9) | 0.0209 (8) |
O23 | 0.0498 (10) | 0.0390 (9) | 0.0320 (9) | 0.0042 (8) | 0.0006 (7) | 0.0067 (7) |
N1—C4 | 1.332 (3) | C7—H7C | 0.9800 |
N1—C3 | 1.462 (3) | C8—H8A | 0.9800 |
N1—H1 | 0.8800 | C8—H8B | 0.9800 |
N2—C4 | 1.340 (3) | C8—H8C | 0.9800 |
N2—C6 | 1.460 (3) | C10—H10A | 0.9800 |
N2—C5 | 1.461 (3) | C10—H10B | 0.9800 |
N3—C4 | 1.333 (3) | C10—H10C | 0.9800 |
N3—C8 | 1.457 (3) | C11—H11A | 0.9800 |
N3—C7 | 1.463 (3) | C11—H11B | 0.9800 |
N4—C9 | 1.330 (3) | C11—H11C | 0.9800 |
N4—C1 | 1.462 (3) | C12—H12A | 0.9800 |
N4—H4 | 0.8800 | C12—H12B | 0.9800 |
N5—C9 | 1.343 (3) | C12—H12C | 0.9800 |
N5—C10 | 1.455 (3) | C13—H13A | 0.9800 |
N5—C11 | 1.459 (3) | C13—H13B | 0.9800 |
N6—C9 | 1.335 (3) | C13—H13C | 0.9800 |
N6—C12 | 1.463 (3) | S1—O132 | 1.362 (10) |
N6—C13 | 1.462 (3) | S1—O122 | 1.394 (11) |
C1—C2 | 1.516 (3) | S1—O111 | 1.425 (2) |
C1—H1A | 0.9900 | S1—O121 | 1.4344 (19) |
C1—H1B | 0.9900 | S1—O131 | 1.437 (2) |
C2—C3 | 1.517 (3) | S1—O112 | 1.453 (11) |
C2—H2A | 0.9900 | S1—C100 | 1.805 (3) |
C2—H2B | 0.9900 | C100—F12 | 1.281 (3) |
C3—H3A | 0.9900 | C100—F13 | 1.311 (3) |
C3—H3B | 0.9900 | C100—F11 | 1.357 (4) |
C5—H5A | 0.9800 | S2—O21 | 1.4291 (19) |
C5—H5B | 0.9800 | S2—O23 | 1.4317 (18) |
C5—H5C | 0.9800 | S2—O22 | 1.4354 (17) |
C6—H6A | 0.9800 | S2—C200 | 1.816 (2) |
C6—H6B | 0.9800 | C200—F23 | 1.319 (3) |
C6—H6C | 0.9800 | C200—F21 | 1.317 (3) |
C7—H7A | 0.9800 | C200—F22 | 1.327 (3) |
C7—H7B | 0.9800 | ||
C4—N1—C3 | 125.94 (18) | N3—C8—H8C | 109.5 |
C4—N1—H1 | 117.0 | H8A—C8—H8C | 109.5 |
C3—N1—H1 | 117.0 | H8B—C8—H8C | 109.5 |
C4—N2—C6 | 121.53 (18) | N4—C9—N6 | 119.29 (18) |
C4—N2—C5 | 121.91 (19) | N4—C9—N5 | 120.75 (18) |
C6—N2—C5 | 115.95 (19) | N6—C9—N5 | 119.94 (18) |
C4—N3—C8 | 122.04 (17) | N5—C10—H10A | 109.5 |
C4—N3—C7 | 122.51 (18) | N5—C10—H10B | 109.5 |
C8—N3—C7 | 115.43 (18) | H10A—C10—H10B | 109.5 |
C9—N4—C1 | 125.10 (17) | N5—C10—H10C | 109.5 |
C9—N4—H4 | 117.4 | H10A—C10—H10C | 109.5 |
C1—N4—H4 | 117.4 | H10B—C10—H10C | 109.5 |
C9—N5—C10 | 122.53 (17) | N5—C11—H11A | 109.5 |
C9—N5—C11 | 122.43 (17) | N5—C11—H11B | 109.5 |
C10—N5—C11 | 115.04 (17) | H11A—C11—H11B | 109.5 |
C9—N6—C12 | 122.56 (18) | N5—C11—H11C | 109.5 |
C9—N6—C13 | 121.78 (17) | H11A—C11—H11C | 109.5 |
C12—N6—C13 | 115.24 (17) | H11B—C11—H11C | 109.5 |
N4—C1—C2 | 111.93 (16) | N6—C12—H12A | 109.5 |
N4—C1—H1A | 109.2 | N6—C12—H12B | 109.5 |
C2—C1—H1A | 109.2 | H12A—C12—H12B | 109.5 |
N4—C1—H1B | 109.2 | N6—C12—H12C | 109.5 |
C2—C1—H1B | 109.2 | H12A—C12—H12C | 109.5 |
H1A—C1—H1B | 107.9 | H12B—C12—H12C | 109.5 |
C1—C2—C3 | 110.61 (17) | N6—C13—H13A | 109.5 |
C1—C2—H2A | 109.5 | N6—C13—H13B | 109.5 |
C3—C2—H2A | 109.5 | H13A—C13—H13B | 109.5 |
C1—C2—H2B | 109.5 | N6—C13—H13C | 109.5 |
C3—C2—H2B | 109.5 | H13A—C13—H13C | 109.5 |
H2A—C2—H2B | 108.1 | H13B—C13—H13C | 109.5 |
N1—C3—C2 | 109.80 (17) | O132—S1—O122 | 124.0 (9) |
N1—C3—H3A | 109.7 | O111—S1—O121 | 115.11 (13) |
C2—C3—H3A | 109.7 | O111—S1—O131 | 113.82 (15) |
N1—C3—H3B | 109.7 | O121—S1—O131 | 114.34 (13) |
C2—C3—H3B | 109.7 | O132—S1—O112 | 117.2 (9) |
H3A—C3—H3B | 108.2 | O122—S1—O112 | 115.8 (9) |
N1—C4—N3 | 121.08 (19) | O132—S1—C100 | 111.7 (8) |
N1—C4—N2 | 118.62 (19) | O122—S1—C100 | 81.7 (9) |
N3—C4—N2 | 120.30 (19) | O111—S1—C100 | 103.08 (14) |
N2—C5—H5A | 109.5 | O121—S1—C100 | 105.32 (13) |
N2—C5—H5B | 109.5 | O131—S1—C100 | 103.26 (12) |
H5A—C5—H5B | 109.5 | O112—S1—C100 | 93.3 (9) |
N2—C5—H5C | 109.5 | F12—C100—F13 | 109.3 (3) |
H5A—C5—H5C | 109.5 | F12—C100—F11 | 107.6 (3) |
H5B—C5—H5C | 109.5 | F13—C100—F11 | 104.1 (2) |
N2—C6—H6A | 109.5 | F12—C100—S1 | 113.09 (19) |
N2—C6—H6B | 109.5 | F13—C100—S1 | 112.99 (19) |
H6A—C6—H6B | 109.5 | F11—C100—S1 | 109.3 (2) |
N2—C6—H6C | 109.5 | O21—S2—O23 | 115.31 (12) |
H6A—C6—H6C | 109.5 | O21—S2—O22 | 114.63 (12) |
H6B—C6—H6C | 109.5 | O23—S2—O22 | 115.08 (12) |
N3—C7—H7A | 109.5 | O21—S2—C200 | 103.63 (12) |
N3—C7—H7B | 109.5 | O23—S2—C200 | 103.20 (11) |
H7A—C7—H7B | 109.5 | O22—S2—C200 | 102.54 (11) |
N3—C7—H7C | 109.5 | F23—C200—F21 | 107.6 (2) |
H7A—C7—H7C | 109.5 | F23—C200—F22 | 106.7 (2) |
H7B—C7—H7C | 109.5 | F21—C200—F22 | 107.4 (2) |
N3—C8—H8A | 109.5 | F23—C200—S2 | 111.78 (16) |
N3—C8—H8B | 109.5 | F21—C200—S2 | 112.38 (17) |
H8A—C8—H8B | 109.5 | F22—C200—S2 | 110.72 (17) |
C9—N4—C1—C2 | 130.8 (2) | O111—S1—C100—F12 | 60.9 (3) |
N4—C1—C2—C3 | −169.80 (17) | O121—S1—C100—F12 | −178.1 (2) |
C4—N1—C3—C2 | 140.4 (2) | O131—S1—C100—F12 | −57.8 (3) |
C1—C2—C3—N1 | 177.71 (17) | O112—S1—C100—F12 | 103.6 (8) |
C3—N1—C4—N3 | 30.0 (3) | O132—S1—C100—F13 | −142.2 (9) |
C3—N1—C4—N2 | −149.9 (2) | O122—S1—C100—F13 | 94.4 (8) |
C8—N3—C4—N1 | 30.8 (3) | O111—S1—C100—F13 | −63.9 (3) |
C7—N3—C4—N1 | −147.6 (2) | O121—S1—C100—F13 | 57.1 (3) |
C8—N3—C4—N2 | −149.3 (2) | O131—S1—C100—F13 | 177.3 (2) |
C7—N3—C4—N2 | 32.3 (3) | O112—S1—C100—F13 | −21.2 (8) |
C6—N2—C4—N1 | 25.1 (3) | O132—S1—C100—F11 | 102.4 (9) |
C5—N2—C4—N1 | −145.5 (2) | O122—S1—C100—F11 | −20.9 (8) |
C6—N2—C4—N3 | −154.8 (2) | O111—S1—C100—F11 | −179.3 (2) |
C5—N2—C4—N3 | 34.6 (3) | O121—S1—C100—F11 | −58.3 (2) |
C1—N4—C9—N6 | 147.78 (19) | O131—S1—C100—F11 | 62.0 (2) |
C1—N4—C9—N5 | −33.7 (3) | O112—S1—C100—F11 | −136.5 (8) |
C12—N6—C9—N4 | 149.6 (2) | O21—S2—C200—F23 | 176.20 (17) |
C13—N6—C9—N4 | −22.5 (3) | O23—S2—C200—F23 | 55.63 (19) |
C12—N6—C9—N5 | −28.9 (3) | O22—S2—C200—F23 | −64.25 (19) |
C13—N6—C9—N5 | 159.0 (2) | O21—S2—C200—F21 | −62.7 (2) |
C10—N5—C9—N4 | 142.8 (2) | O23—S2—C200—F21 | 176.76 (18) |
C11—N5—C9—N4 | −36.3 (3) | O22—S2—C200—F21 | 56.9 (2) |
C10—N5—C9—N6 | −38.7 (3) | O21—S2—C200—F22 | 57.38 (19) |
C11—N5—C9—N6 | 142.1 (2) | O23—S2—C200—F22 | −63.20 (19) |
O132—S1—C100—F12 | −17.4 (9) | O22—S2—C200—F22 | 176.93 (17) |
O122—S1—C100—F12 | −140.8 (8) |
Experimental details
(I) | (II) | (III) | (IV) | |
Crystal data | ||||
Chemical formula | C13H32N62+·2Br− | C13H32N62+·BC24H20−·Cl− | (C13H32N6)[HgCl4] | C13H32N62+·2CF3O3S− |
Mr | 432.27 | 627.11 | 614.84 | 570.59 |
Crystal system, space group | Triclinic, P1 | Monoclinic, P21/c | Monoclinic, P21/c | Triclinic, P1 |
Temperature (K) | 120 | 150 | 120 | 120 |
a, b, c (Å) | 12.4256 (14), 12.5254 (15), 12.6935 (15) | 17.5770 (8), 9.3797 (4), 22.4953 (10) | 8.3199 (4), 18.0809 (9), 15.8086 (8) | 8.8771 (7), 12.3802 (10), 12.5704 (10) |
α, β, γ (°) | 79.465 (3), 89.731 (3), 89.361 (2) | 90, 107.034 (1), 90 | 90, 104.291 (1), 90 | 108.939 (2), 91.478 (2), 97.775 (2) |
V (Å3) | 1942.1 (4) | 3546.0 (3) | 2304.5 (2) | 1291.10 (18) |
Z | 4 | 4 | 4 | 2 |
Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
µ (mm−1) | 4.18 | 0.14 | 7.15 | 0.29 |
Crystal size (mm) | 0.42 × 0.22 × 0.20 | 0.20 × 0.20 × 0.15 | 0.45 × 0.20 × 0.08 | 0.40 × 0.20 × 0.20 |
Data collection | ||||
Diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer | Bruker SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2002) | Multi-scan (SADABS; Bruker, 2002) | Multi-scan (SADABS; Bruker, 2002) | Multi-scan (SADABS; Bruker, 2002) |
Tmin, Tmax | 0.243, 0.435 | 0.962, 0.975 | 0.133, 0.563 | 0.893, 0.944 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 19556, 9242, 5769 | 39279, 7800, 4307 | 23407, 5049, 4421 | 7636, 5165, 4404 |
Rint | 0.065 | 0.100 | 0.025 | 0.012 |
(sin θ/λ)max (Å−1) | 0.658 | 0.641 | 0.641 | 0.625 |
Refinement | ||||
R[F2 > 2σ(F2)], wR(F2), S | 0.058, 0.139, 0.99 | 0.044, 0.072, 0.91 | 0.028, 0.087, 1.07 | 0.046, 0.121, 1.03 |
No. of reflections | 9242 | 7800 | 5049 | 5165 |
No. of parameters | 387 | 414 | 225 | 337 |
No. of restraints | 0 | 0 | 0 | 30 |
H-atom treatment | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.95, −0.89 | 0.21, −0.24 | 0.92, −0.55 | 0.76, −0.51 |
Computer programs: SMART (Bruker, 2002), SMART, SAINT (Bruker, 2002), SAINT (Bruker, 2002, SHELXTL (Bruker, 2002), SHELXTL (Bruker, 2002, SHELXTL.
Torsion angle | (I) | (II) | (III) | (IV) | (V) |
N4—C1—C2—C3 | -62.8 (6) | 63.4 (2) | -179.9 (3) | -169.8 (2) | 69.8 (2) |
C1—C2—C3—N1 | -173.4 (4) | -177.6 (2) | 175.5 (3) | 177.7 (2) | -173.3 (1) |
Compound | D—H···A | D—H | H···A | D···A | D—H···A | |
(Ia) | N11—H11···Br1 | 0.88 | 2.42 | 3.282 (4) | 168 | |
(Ib) | N21—H21···Br4 | 0.88 | 2.43 | 3.283 (4) | 165 | |
(Ib) | N24—H24···Br2 | 0.88 | 2.54 | 3.396 (4) | 166 | |
(Ia) | N14—H14···Br3 | 0.88 | 2.52 | 3.373 (4) | 165 | |
(Ib) | C28—H20Q···Br4i | 0.98 | 2.81 | 3.736 (6) | 158 | |
(Ib) | C213—H21M···Br2ii | 0.98 | 2.82 | 3.764 (5) | 163 | |
(II) | N1—H1···Cl1iii | 0.88 | 2.41 | 3.2516 (18) | 160 | |
(II) | N4—H4···Cl1 | 0.88 | 2.29 | 3.1668 (17) | 172 | |
(III) | N1—H1···Cl4 | 0.88 | 2.50 | 3.349 (4) | 164 | |
(III) | N4—H4···Cl1 | 0.88 | 2.36 | 3.215 (4) | 164 | |
(III) | C1—H1A···Cl3iv | 0.99 | 2.65 | 3.597 (4) | 161 | |
(IV) | N4—H4···O22 | 0.88 | 2.03 | 2.796 (2) | 144 | |
(IV) | N1—H1···O111 | 0.88 | 1.98 | 2.855 (3) | 172 | |
(IV) | N1—H1···O112 | 0.88 | 2.05 | 2.883 (18) | 157 | |
(IV) | C2—H2B···O112 | 0.99 | 2.44 | 3.171 (19) | 130 | |
(IV) | C5—H5C···O21v | 0.98 | 2.49 | 3.448 (3) | 166 | |
(IV) | C7—H7B···O132vi | 0.98 | 2.25 | 3.111 (17) | 145 | |
(IV) | C8—H8A···O131vi | 0.98 | 2.46 | 3.245 (3) | 137 |
Symmetry codes: i (-x + 2,-y + 1,-z + 1); ii (-x + 1,-y + 2,-z + 1); iii (-x + 1,-y,-z + 1); iv (x − 1,y,z); v (x,y,z + 1); vi (x − 1,y,z); |
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The series of four structures presented here consists of protonated bis-guanidine cations, [btmgpH2]2+, crystallized with different anions, viz. (I) with Br− (Fig. 1), (II) with [BPh4]− and Cl− (Fig. 2), (III) with [HgCl4]2− (Fig. 3) and (IV) with [CF3SO3]− (triflat) (Fig. 4). Already known from ealier work is an initial member of this series, namely the structure (V) with Cl− (Pohl et al., 2000). Although isomolecular with (V), the structure of (I) is not isotypic but exhibits two independent molecules, (IA) and (IB), with different conformations per asymmetric unit. As expected, the bond length parameters for the [btmgpH2]2+ moieties of all structures are very similar [C—C = 1.504 (2)–1.536 (7) Å, N—C(propyl) = 1.455 (6)–1.477 (6) Å, N═C = 1.326 (7)–1.341 (6) Å and C–N(guanidyl) = 1.331 (2)–1.343 (3) Å]. The N—C—C and C—C—C angles range from 109.1 (2) to 111.9 (2)° and 109.1 (3) to 114.1 (2)°, respectively.
Significant geometric differences, however, associated with the different packing patterns, are noted for the N—C—C—C torsion angles, which are given in Table 1. Fig. 5 depicts these different conformations. Likewise, the angles between the two NCN2 guanidine planes of each ligand cation differ markedly, being 15.5 (3)° for (Ia), 24.7 (3)° for (Ib), 67.00 (7)° for (II), 74.1 (1)° for (III), 67.23 (7)° for (IV) and 82.60 (6)° for (V). The relative orientations of the pairs of CNMe2 planes, on the other hand, are again very similar for all structures and their corresponding dihedral angles lie in the narrow range 52.1 (1)–56.1 (1)°. Only the conformation of cation (III) shows approximatively Cs symmetry, with a non-crystallographic mirror plane running through C2 and the attached H atoms; the other cations have C1 point-group symmetry.
Cmpounds (II) and (III) each pack with two intermolecular cation–anion N—H···Cl hydrogen bonds of similar geometries (Table 2). In (II) (Fig. 6), centrosymmetric dimeric units each with two cations and anions are formed, which are stacked along [010]. In (III) (Fig. 7), the two Cl acceptors, Cl1 and Cl4, of each anion bridge to the two NH sites of a cation; additionally, a C—H···Cl interaction from Cl3 connects this cation–anion pair to another cation site. Compound (I) exhibits N—H···Br interactions with short (2.4–2.5 Å) H.·Br distances and weaker C—H···Br interactions with an H···Br distance of about 2.8 Å, which link the (Ia) and (Ib) cations into a common network. In (IV), two strong N—H···O bridges link the cation to two triflat anions, thus forming 1:2 cation–anion units, which are then connected by C–H.·O interactions in a zigzag manner along [001]. The BPh4 and HgCl4 anions of (II) and (III) exhibit no unusual features and need no further discussion. The SO3 group of the triflat anion 1 in (IV) is disordered around the C—-S axis over two positions with occupation factors 0.919 (4) and 0.081 (4).