organic compounds
N,N,N′,N′,N′′,N′′,N′′′,N′′′-Octamethyl(but-2-yne)bisamidinium bis(tetraphenylborate)
aFakultät Chemie/Organische Chemie, Hochschule Aalen, Beethovenstrasse 1, D-73430 Aalen, Germany
*Correspondence e-mail: willi.kantlehner@hs-aalen.de
The 12H24N42+.2C24H20B−, comprises half a cation and one tetraphenylborate ion. An inversion centre is situated at the mid-point of the triple C≡C bond in the cation. The bisamidinium C—N bonds [1.3249 (11) and 1.3267 (11) Å] have double-bond character and both positive charges are delocalized between the dimethylamino groups. The bonds between the N atoms and the terminal C-methyl groups all have values characteristic for a typical single bond [1.4656 (12)–1.4687 (12) Å]. The acetylenic bond length [1.1889 (18) Å] is consistent with a triple C≡C bond and the butyne carbon chain is almost linear. C—H⋯π interactions between the bisamidinium methyl H atoms and the phenyl C atoms of the tetraphenylborate ions are present. The phenyl rings form aromatic pockets, in which the cations are embedded. This leads to the formation of a two-dimensional supramolecular pattern in the ab plane.
of the title salt, CCCDC reference: 1450255
Structure description
Recently, we have described the preparation of N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethyl(but-2-yne)bisamidinium bis(tetrafluoroborate) by the cleavage of 1,1,1,4,4,4-hexakis(dimethylamino)-2-butyne with trifluoroacetic anhydride (Drandarov et al., 2012). The salt reacts with nucleophilic reagents, yielding various amidinium and bis(amidinium) salts and ketene (Drandarov et al., 2015). A number of heterocyclic bis(amidinium) salts could also be prepared by cycloaddition reactions (Drandarov & Kantlehner, 2012). The title salt is the second one in our series, which has been structurally characterized after with sodium tetraphenylborate.
The C-methyl groups, all have values characteristic for a typical single bond [1.4656 (12)–1.4687 (12) Å]. The butyne carbon chain is almost linear, the C1—C2—C2i angle being 179.0 (1)°. The C2≡C2i triple bond is 1.1889 (18) Å while the C1—C2 bond length is 1.4377 (12) Å (Fig. 1).
contains one half of the cation and one tetraphenylborate ion. An inversion centre is situated at the mid-point of the triple C≡C bond in the cation. Prominent bond parameters in the bisamidinium ion are: N1—C1 = 1.3249 (11) Å and N2—C1 = 1.3267 (11) Å, indicating N—C double-bond character. Both positive charges are distributed between the dimethylamino groups. The bonds between the N atoms and the terminalThe bond lengths of the dication agree very well with the data from the N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethyl(but-2-yne)bisamidinium bis(tetrafluoroborate) (Drandarov et al., 2012). In the tetraphenylborate salt, the angle between the N1–C1–N2 and N1i–C1i–N2i planes is 0° and the C1—C2—C2i—C1i torsion angle is 180.0 (1)°. This is completely different from the tetrafluoroborate salt (Drandarov et al., 2012), where the N–C–N planes between the two amidinium units are nearly perpendicular to each other [85.1 (2)°] and C1—C2—C2i—C1i = 101.3 (1)°. The bond lengths and angles in the tetraphenylborate ion are in good agreement with the data for alkali metal tetraphenylborates (Behrens et al., 2012).
analysis ofC—H⋯π interactions between the hydrogen atoms of –N(CH3)2 groups of the cation and the phenyl carbon atoms (centroids: Cg1 = C13–C18, Cg2 = C19–C24 and Cg3 = C25–C30) of the tetraphenylborate ion are present (Fig. 2), ranging from 2.54 to 2.85 Å (Table 1). The phenyl rings form aromatic pockets in which the cations are embedded. This leads to the formation of a two-dimensional supramolecular pattern along the ab plane.
Synthesis and crystallization
The title compound was obtained by reacting an acetonitrile solution of N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethyl(but-2-yne)bisamidinium bis(tetrafluoroborate) (Drandarov et al., 2012b) with two equivalents of sodium tetraphenylborate. After stirring for one hour at room temperature, the precipitated sodium tetrafluoroborate was filtered off. The title compound crystallized from a saturated acetonitrile solution after several days at 273 K, forming yellow single crystals.
Refinement
Crystal data, data collection and structure .
details are summarized in Table 2Structural data
CCDC reference: 1450255
https://doi.org/10.1107/S2414314616001668/hb4007sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314616001668/hb4007Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2414314616001668/hb4007Isup3.cml
Data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: DIAMOND (Brandenburg & Putz, 2005); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).2(C24H20B)·C12H24N4 | F(000) = 924 |
Mr = 862.77 | Dx = 1.209 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 13.8527 (5) Å | Cell parameters from 50722 reflections |
b = 10.4892 (4) Å | θ = 1.7–30.6° |
c = 16.7462 (6) Å | µ = 0.07 mm−1 |
β = 103.034 (2)° | T = 100 K |
V = 2370.60 (15) Å3 | Block, yellow |
Z = 2 | 0.35 × 0.23 × 0.10 mm |
Bruker Kappa APEXII Duo diffractometer | 6046 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Triumph monochromator | θmax = 30.6°, θmin = 1.7° |
φ scans, and ω scans | h = −19→19 |
50722 measured reflections | k = −14→14 |
7271 independent reflections | l = −23→23 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.113 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0612P)2 + 0.7005P] where P = (Fo2 + 2Fc2)/3 |
7271 reflections | (Δ/σ)max < 0.001 |
302 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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. The crystal was refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.35927 (6) | 0.47150 (8) | 0.10360 (5) | 0.01587 (15) | |
C1 | 0.36503 (6) | 0.50484 (8) | 0.02850 (5) | 0.01380 (16) | |
N2 | 0.28770 (5) | 0.54206 (8) | −0.02893 (5) | 0.01533 (15) | |
C2 | 0.46046 (7) | 0.50074 (9) | 0.00825 (5) | 0.01554 (17) | |
C3 | 0.44900 (7) | 0.46323 (11) | 0.16970 (6) | 0.02152 (19) | |
H3A | 0.4792 | 0.3789 | 0.1688 | 0.032* | |
H3B | 0.4315 | 0.4763 | 0.2226 | 0.032* | |
H3C | 0.4962 | 0.5290 | 0.1618 | 0.032* | |
C4 | 0.26820 (7) | 0.41956 (11) | 0.12146 (6) | 0.0228 (2) | |
H4A | 0.2361 | 0.4851 | 0.1482 | 0.034* | |
H4B | 0.2844 | 0.3458 | 0.1579 | 0.034* | |
H4C | 0.2232 | 0.3931 | 0.0702 | 0.034* | |
C5 | 0.29145 (7) | 0.53857 (11) | −0.11567 (6) | 0.02100 (19) | |
H5A | 0.3159 | 0.6204 | −0.1312 | 0.032* | |
H5B | 0.2249 | 0.5228 | −0.1492 | 0.032* | |
H5C | 0.3361 | 0.4702 | −0.1246 | 0.032* | |
C6 | 0.20340 (7) | 0.60966 (10) | −0.00906 (6) | 0.02072 (19) | |
H6A | 0.1480 | 0.5503 | −0.0124 | 0.031* | |
H6B | 0.1831 | 0.6795 | −0.0481 | 0.031* | |
H6C | 0.2228 | 0.6444 | 0.0466 | 0.031* | |
B1 | 0.48759 (7) | 0.85310 (10) | 0.22798 (6) | 0.01361 (17) | |
C7 | 0.51523 (7) | 0.83135 (9) | 0.13802 (5) | 0.01530 (17) | |
C8 | 0.44148 (7) | 0.82171 (9) | 0.06504 (6) | 0.01623 (17) | |
H8 | 0.3741 | 0.8182 | 0.0688 | 0.019* | |
C9 | 0.46258 (7) | 0.81705 (9) | −0.01235 (6) | 0.01939 (18) | |
H9 | 0.4099 | 0.8123 | −0.0597 | 0.023* | |
C10 | 0.55982 (8) | 0.81925 (10) | −0.02087 (6) | 0.02158 (19) | |
H10 | 0.5745 | 0.8168 | −0.0736 | 0.026* | |
C11 | 0.63533 (7) | 0.82504 (10) | 0.04943 (6) | 0.0224 (2) | |
H11 | 0.7025 | 0.8245 | 0.0450 | 0.027* | |
C12 | 0.61303 (7) | 0.83171 (10) | 0.12652 (6) | 0.01945 (18) | |
H12 | 0.6662 | 0.8367 | 0.1735 | 0.023* | |
C13 | 0.36643 (6) | 0.86150 (9) | 0.21106 (5) | 0.01375 (16) | |
C14 | 0.31746 (7) | 0.97595 (9) | 0.18302 (6) | 0.01610 (17) | |
H14 | 0.3559 | 1.0508 | 0.1825 | 0.019* | |
C15 | 0.21492 (7) | 0.98402 (9) | 0.15596 (6) | 0.01789 (18) | |
H15 | 0.1850 | 1.0629 | 0.1363 | 0.021* | |
C16 | 0.15618 (7) | 0.87675 (10) | 0.15760 (6) | 0.01854 (18) | |
H16 | 0.0862 | 0.8815 | 0.1390 | 0.022* | |
C17 | 0.20162 (7) | 0.76264 (10) | 0.18688 (6) | 0.01761 (18) | |
H17 | 0.1625 | 0.6890 | 0.1895 | 0.021* | |
C18 | 0.30466 (6) | 0.75586 (9) | 0.21241 (5) | 0.01508 (17) | |
H18 | 0.3341 | 0.6765 | 0.2315 | 0.018* | |
C19 | 0.53348 (6) | 0.74262 (8) | 0.29627 (5) | 0.01362 (16) | |
C20 | 0.62028 (7) | 0.67306 (9) | 0.29618 (6) | 0.01631 (17) | |
H20 | 0.6510 | 0.6835 | 0.2513 | 0.020* | |
C21 | 0.66342 (7) | 0.58937 (9) | 0.35897 (6) | 0.01956 (18) | |
H21 | 0.7224 | 0.5451 | 0.3562 | 0.023* | |
C22 | 0.62051 (7) | 0.57050 (9) | 0.42547 (6) | 0.02021 (19) | |
H22 | 0.6501 | 0.5147 | 0.4688 | 0.024* | |
C23 | 0.53331 (7) | 0.63495 (9) | 0.42726 (6) | 0.01810 (18) | |
H23 | 0.5021 | 0.6221 | 0.4716 | 0.022* | |
C24 | 0.49160 (6) | 0.71839 (9) | 0.36407 (5) | 0.01535 (17) | |
H24 | 0.4320 | 0.7611 | 0.3669 | 0.018* | |
C25 | 0.53179 (6) | 0.99115 (9) | 0.26813 (6) | 0.01544 (17) | |
C26 | 0.51539 (7) | 1.02990 (9) | 0.34439 (6) | 0.01835 (18) | |
H26 | 0.4804 | 0.9740 | 0.3725 | 0.022* | |
C27 | 0.54799 (8) | 1.14631 (10) | 0.38057 (7) | 0.0242 (2) | |
H27 | 0.5351 | 1.1683 | 0.4322 | 0.029* | |
C28 | 0.59942 (8) | 1.23028 (10) | 0.34106 (8) | 0.0279 (2) | |
H28 | 0.6223 | 1.3097 | 0.3654 | 0.034* | |
C29 | 0.61661 (8) | 1.19598 (10) | 0.26577 (7) | 0.0267 (2) | |
H29 | 0.6518 | 1.2524 | 0.2382 | 0.032* | |
C30 | 0.58281 (7) | 1.07926 (10) | 0.22980 (6) | 0.02066 (19) | |
H30 | 0.5948 | 1.0588 | 0.1776 | 0.025* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0133 (3) | 0.0207 (4) | 0.0138 (3) | 0.0001 (3) | 0.0034 (3) | 0.0011 (3) |
C1 | 0.0132 (4) | 0.0139 (4) | 0.0144 (4) | −0.0003 (3) | 0.0033 (3) | −0.0013 (3) |
N2 | 0.0130 (3) | 0.0190 (4) | 0.0135 (3) | 0.0013 (3) | 0.0022 (3) | 0.0003 (3) |
C2 | 0.0159 (4) | 0.0171 (4) | 0.0132 (4) | 0.0009 (3) | 0.0023 (3) | 0.0009 (3) |
C3 | 0.0173 (4) | 0.0317 (5) | 0.0141 (4) | 0.0030 (4) | 0.0005 (3) | 0.0005 (4) |
C4 | 0.0190 (4) | 0.0307 (5) | 0.0200 (4) | −0.0057 (4) | 0.0073 (3) | 0.0030 (4) |
C5 | 0.0201 (4) | 0.0298 (5) | 0.0124 (4) | 0.0000 (4) | 0.0023 (3) | 0.0001 (3) |
C6 | 0.0150 (4) | 0.0251 (5) | 0.0212 (4) | 0.0057 (3) | 0.0023 (3) | −0.0021 (4) |
B1 | 0.0117 (4) | 0.0148 (4) | 0.0139 (4) | −0.0003 (3) | 0.0019 (3) | 0.0011 (3) |
C7 | 0.0154 (4) | 0.0152 (4) | 0.0154 (4) | 0.0001 (3) | 0.0036 (3) | 0.0021 (3) |
C8 | 0.0173 (4) | 0.0158 (4) | 0.0156 (4) | −0.0005 (3) | 0.0036 (3) | 0.0001 (3) |
C9 | 0.0251 (5) | 0.0179 (4) | 0.0148 (4) | −0.0018 (3) | 0.0038 (3) | −0.0002 (3) |
C10 | 0.0297 (5) | 0.0195 (4) | 0.0183 (4) | −0.0013 (4) | 0.0112 (4) | 0.0007 (3) |
C11 | 0.0211 (4) | 0.0248 (5) | 0.0241 (5) | 0.0005 (4) | 0.0109 (4) | 0.0029 (4) |
C12 | 0.0157 (4) | 0.0240 (5) | 0.0190 (4) | 0.0007 (3) | 0.0046 (3) | 0.0033 (4) |
C13 | 0.0132 (4) | 0.0165 (4) | 0.0114 (4) | 0.0000 (3) | 0.0024 (3) | −0.0010 (3) |
C14 | 0.0149 (4) | 0.0175 (4) | 0.0155 (4) | 0.0006 (3) | 0.0027 (3) | −0.0001 (3) |
C15 | 0.0164 (4) | 0.0211 (4) | 0.0154 (4) | 0.0049 (3) | 0.0017 (3) | −0.0006 (3) |
C16 | 0.0122 (4) | 0.0280 (5) | 0.0148 (4) | 0.0010 (3) | 0.0015 (3) | −0.0038 (3) |
C17 | 0.0137 (4) | 0.0231 (5) | 0.0159 (4) | −0.0035 (3) | 0.0032 (3) | −0.0040 (3) |
C18 | 0.0139 (4) | 0.0170 (4) | 0.0140 (4) | −0.0007 (3) | 0.0022 (3) | −0.0016 (3) |
C19 | 0.0129 (3) | 0.0131 (4) | 0.0138 (4) | −0.0020 (3) | 0.0010 (3) | −0.0010 (3) |
C20 | 0.0162 (4) | 0.0162 (4) | 0.0162 (4) | 0.0002 (3) | 0.0029 (3) | −0.0008 (3) |
C21 | 0.0187 (4) | 0.0165 (4) | 0.0220 (4) | 0.0035 (3) | 0.0015 (3) | 0.0006 (3) |
C22 | 0.0236 (4) | 0.0155 (4) | 0.0189 (4) | 0.0005 (3) | −0.0008 (3) | 0.0031 (3) |
C23 | 0.0210 (4) | 0.0170 (4) | 0.0157 (4) | −0.0037 (3) | 0.0028 (3) | 0.0015 (3) |
C24 | 0.0145 (4) | 0.0153 (4) | 0.0158 (4) | −0.0018 (3) | 0.0027 (3) | −0.0003 (3) |
C25 | 0.0113 (3) | 0.0154 (4) | 0.0175 (4) | 0.0009 (3) | −0.0011 (3) | 0.0024 (3) |
C26 | 0.0153 (4) | 0.0173 (4) | 0.0210 (4) | 0.0007 (3) | 0.0009 (3) | −0.0009 (3) |
C27 | 0.0208 (4) | 0.0198 (5) | 0.0281 (5) | 0.0037 (4) | −0.0027 (4) | −0.0061 (4) |
C28 | 0.0218 (5) | 0.0147 (4) | 0.0408 (6) | −0.0005 (4) | −0.0066 (4) | −0.0027 (4) |
C29 | 0.0206 (4) | 0.0177 (5) | 0.0377 (6) | −0.0043 (4) | −0.0018 (4) | 0.0083 (4) |
C30 | 0.0174 (4) | 0.0189 (4) | 0.0237 (5) | −0.0015 (3) | 0.0003 (3) | 0.0063 (4) |
N1—C1 | 1.3249 (11) | C12—H12 | 0.9500 |
N1—C4 | 1.4656 (12) | C13—C18 | 1.4034 (12) |
N1—C3 | 1.4687 (12) | C13—C14 | 1.4064 (13) |
C1—N2 | 1.3267 (11) | C14—C15 | 1.3928 (12) |
C1—C2 | 1.4377 (12) | C14—H14 | 0.9500 |
N2—C5 | 1.4656 (12) | C15—C16 | 1.3925 (14) |
N2—C6 | 1.4672 (12) | C15—H15 | 0.9500 |
C2—C2i | 1.1889 (18) | C16—C17 | 1.3892 (14) |
C3—H3A | 0.9800 | C16—H16 | 0.9500 |
C3—H3B | 0.9800 | C17—C18 | 1.3963 (12) |
C3—H3C | 0.9800 | C17—H17 | 0.9500 |
C4—H4A | 0.9800 | C18—H18 | 0.9500 |
C4—H4B | 0.9800 | C19—C20 | 1.4068 (12) |
C4—H4C | 0.9800 | C19—C24 | 1.4097 (12) |
C5—H5A | 0.9800 | C20—C21 | 1.3964 (13) |
C5—H5B | 0.9800 | C20—H20 | 0.9500 |
C5—H5C | 0.9800 | C21—C22 | 1.3897 (14) |
C6—H6A | 0.9800 | C21—H21 | 0.9500 |
C6—H6B | 0.9800 | C22—C23 | 1.3904 (14) |
C6—H6C | 0.9800 | C22—H22 | 0.9500 |
B1—C13 | 1.6404 (13) | C23—C24 | 1.3942 (13) |
B1—C19 | 1.6514 (13) | C23—H23 | 0.9500 |
B1—C7 | 1.6517 (13) | C24—H24 | 0.9500 |
B1—C25 | 1.6547 (14) | C25—C30 | 1.4037 (13) |
C7—C8 | 1.4086 (12) | C25—C26 | 1.4065 (13) |
C7—C12 | 1.4107 (12) | C26—C27 | 1.3923 (14) |
C8—C9 | 1.3923 (13) | C26—H26 | 0.9500 |
C8—H8 | 0.9500 | C27—C28 | 1.3905 (17) |
C9—C10 | 1.3863 (14) | C27—H27 | 0.9500 |
C9—H9 | 0.9500 | C28—C29 | 1.3826 (18) |
C10—C11 | 1.3886 (15) | C28—H28 | 0.9500 |
C10—H10 | 0.9500 | C29—C30 | 1.3978 (15) |
C11—C12 | 1.3953 (14) | C29—H29 | 0.9500 |
C11—H11 | 0.9500 | C30—H30 | 0.9500 |
C1—N1—C4 | 122.05 (8) | C11—C12—H12 | 118.5 |
C1—N1—C3 | 120.61 (8) | C7—C12—H12 | 118.5 |
C4—N1—C3 | 116.44 (8) | C18—C13—C14 | 115.43 (8) |
N1—C1—N2 | 123.66 (8) | C18—C13—B1 | 123.96 (8) |
N1—C1—C2 | 118.12 (8) | C14—C13—B1 | 120.08 (8) |
N2—C1—C2 | 118.22 (8) | C15—C14—C13 | 122.70 (9) |
C1—N2—C5 | 120.52 (8) | C15—C14—H14 | 118.7 |
C1—N2—C6 | 122.11 (8) | C13—C14—H14 | 118.7 |
C5—N2—C6 | 116.41 (8) | C16—C15—C14 | 120.14 (9) |
C2i—C2—C1 | 179.01 (14) | C16—C15—H15 | 119.9 |
N1—C3—H3A | 109.5 | C14—C15—H15 | 119.9 |
N1—C3—H3B | 109.5 | C17—C16—C15 | 118.87 (8) |
H3A—C3—H3B | 109.5 | C17—C16—H16 | 120.6 |
N1—C3—H3C | 109.5 | C15—C16—H16 | 120.6 |
H3A—C3—H3C | 109.5 | C16—C17—C18 | 120.17 (9) |
H3B—C3—H3C | 109.5 | C16—C17—H17 | 119.9 |
N1—C4—H4A | 109.5 | C18—C17—H17 | 119.9 |
N1—C4—H4B | 109.5 | C17—C18—C13 | 122.66 (9) |
H4A—C4—H4B | 109.5 | C17—C18—H18 | 118.7 |
N1—C4—H4C | 109.5 | C13—C18—H18 | 118.7 |
H4A—C4—H4C | 109.5 | C20—C19—C24 | 114.49 (8) |
H4B—C4—H4C | 109.5 | C20—C19—B1 | 123.97 (8) |
N2—C5—H5A | 109.5 | C24—C19—B1 | 121.35 (8) |
N2—C5—H5B | 109.5 | C21—C20—C19 | 123.09 (9) |
H5A—C5—H5B | 109.5 | C21—C20—H20 | 118.5 |
N2—C5—H5C | 109.5 | C19—C20—H20 | 118.5 |
H5A—C5—H5C | 109.5 | C22—C21—C20 | 120.35 (9) |
H5B—C5—H5C | 109.5 | C22—C21—H21 | 119.8 |
N2—C6—H6A | 109.5 | C20—C21—H21 | 119.8 |
N2—C6—H6B | 109.5 | C21—C22—C23 | 118.60 (9) |
H6A—C6—H6B | 109.5 | C21—C22—H22 | 120.7 |
N2—C6—H6C | 109.5 | C23—C22—H22 | 120.7 |
H6A—C6—H6C | 109.5 | C22—C23—C24 | 120.15 (9) |
H6B—C6—H6C | 109.5 | C22—C23—H23 | 119.9 |
C13—B1—C19 | 112.11 (7) | C24—C23—H23 | 119.9 |
C13—B1—C7 | 106.77 (7) | C23—C24—C19 | 123.30 (8) |
C19—B1—C7 | 113.74 (7) | C23—C24—H24 | 118.3 |
C13—B1—C25 | 107.07 (7) | C19—C24—H24 | 118.3 |
C19—B1—C25 | 106.46 (7) | C30—C25—C26 | 115.21 (9) |
C7—B1—C25 | 110.54 (7) | C30—C25—B1 | 124.66 (8) |
C8—C7—C12 | 114.38 (8) | C26—C25—B1 | 120.07 (8) |
C8—C7—B1 | 121.95 (8) | C27—C26—C25 | 123.06 (10) |
C12—C7—B1 | 123.46 (8) | C27—C26—H26 | 118.5 |
C9—C8—C7 | 123.14 (9) | C25—C26—H26 | 118.5 |
C9—C8—H8 | 118.4 | C28—C27—C26 | 119.95 (10) |
C7—C8—H8 | 118.4 | C28—C27—H27 | 120.0 |
C10—C9—C8 | 120.53 (9) | C26—C27—H27 | 120.0 |
C10—C9—H9 | 119.7 | C29—C28—C27 | 118.76 (10) |
C8—C9—H9 | 119.7 | C29—C28—H28 | 120.6 |
C9—C10—C11 | 118.50 (9) | C27—C28—H28 | 120.6 |
C9—C10—H10 | 120.7 | C28—C29—C30 | 120.73 (10) |
C11—C10—H10 | 120.7 | C28—C29—H29 | 119.6 |
C10—C11—C12 | 120.32 (9) | C30—C29—H29 | 119.6 |
C10—C11—H11 | 119.8 | C29—C30—C25 | 122.28 (10) |
C12—C11—H11 | 119.8 | C29—C30—H30 | 118.9 |
C11—C12—C7 | 123.09 (9) | C25—C30—H30 | 118.9 |
C4—N1—C1—N2 | 27.07 (14) | C15—C16—C17—C18 | −1.38 (14) |
C3—N1—C1—N2 | −164.18 (9) | C16—C17—C18—C13 | 0.89 (14) |
C4—N1—C1—C2 | −153.09 (9) | C14—C13—C18—C17 | 0.72 (13) |
C3—N1—C1—C2 | 15.67 (13) | B1—C13—C18—C17 | −170.95 (8) |
N1—C1—N2—C5 | −160.48 (9) | C13—B1—C19—C20 | 149.05 (8) |
C2—C1—N2—C5 | 19.68 (13) | C7—B1—C19—C20 | 27.79 (12) |
N1—C1—N2—C6 | 31.11 (14) | C25—B1—C19—C20 | −94.19 (10) |
C2—C1—N2—C6 | −148.73 (9) | C13—B1—C19—C24 | −36.27 (11) |
C13—B1—C7—C8 | −0.75 (12) | C7—B1—C19—C24 | −157.52 (8) |
C19—B1—C7—C8 | 123.44 (9) | C25—B1—C19—C24 | 80.50 (9) |
C25—B1—C7—C8 | −116.87 (9) | C24—C19—C20—C21 | −1.70 (13) |
C13—B1—C7—C12 | 173.68 (8) | B1—C19—C20—C21 | 173.32 (9) |
C19—B1—C7—C12 | −62.12 (11) | C19—C20—C21—C22 | 0.50 (15) |
C25—B1—C7—C12 | 57.56 (11) | C20—C21—C22—C23 | 1.03 (14) |
C12—C7—C8—C9 | −1.99 (14) | C21—C22—C23—C24 | −1.24 (14) |
B1—C7—C8—C9 | 172.92 (9) | C22—C23—C24—C19 | −0.06 (14) |
C7—C8—C9—C10 | 1.31 (15) | C20—C19—C24—C23 | 1.48 (13) |
C8—C9—C10—C11 | 0.56 (15) | B1—C19—C24—C23 | −173.68 (8) |
C9—C10—C11—C12 | −1.58 (15) | C13—B1—C25—C30 | −114.00 (9) |
C10—C11—C12—C7 | 0.83 (16) | C19—B1—C25—C30 | 125.92 (9) |
C8—C7—C12—C11 | 0.92 (14) | C7—B1—C25—C30 | 1.93 (12) |
B1—C7—C12—C11 | −173.89 (9) | C13—B1—C25—C26 | 63.10 (10) |
C19—B1—C13—C18 | −34.32 (12) | C19—B1—C25—C26 | −56.98 (10) |
C7—B1—C13—C18 | 90.87 (10) | C7—B1—C25—C26 | 179.03 (8) |
C25—B1—C13—C18 | −150.71 (8) | C30—C25—C26—C27 | −0.75 (13) |
C19—B1—C13—C14 | 154.37 (8) | B1—C25—C26—C27 | −178.12 (8) |
C7—B1—C13—C14 | −80.44 (10) | C25—C26—C27—C28 | −0.03 (15) |
C25—B1—C13—C14 | 37.98 (11) | C26—C27—C28—C29 | 0.36 (15) |
C18—C13—C14—C15 | −1.88 (13) | C27—C28—C29—C30 | 0.14 (15) |
B1—C13—C14—C15 | 170.14 (8) | C28—C29—C30—C25 | −1.01 (15) |
C13—C14—C15—C16 | 1.44 (14) | C26—C25—C30—C29 | 1.26 (13) |
C14—C15—C16—C17 | 0.26 (14) | B1—C25—C30—C29 | 178.49 (9) |
Symmetry code: (i) −x+1, −y+1, −z. |
Cg1, Cg2 and Cg3 are the centroids of the C13–C18, C19–C24 and C25–C30 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C4—H4B···Cg1ii | 0.98 | 2.85 | 3.401 (1) | 116 |
C5—H5B···Cg3iii | 0.98 | 2.59 | 3.489 (1) | 153 |
C6—H6B···Cg2iii | 0.98 | 2.54 | 3.487 (1) | 162 |
Symmetry codes: (ii) −x+1/2, y−1/2, −z+1/2; (iii) x−1/2, −y+3/2, z−1/2. |
Acknowledgements
The authors thank Dr W. Frey (Institut für Organische Chemie, Universität Stuttgart) for measuring the diffraction data and Dr K. Drandarov (Institut für Organische Chemie, Universität Stuttgart) for the sample of N,N,N′,N′,N′′,N′′,N′′′,N′′′-octamethyl(but-2-yne)bisamidinium bis(tetrafluoroborate).
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