organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

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ISSN: 2056-9890

(1,2-Dicarba-closo-dodeca­boran­yl)tri­methyl­methanaminium iodide

aDepartment of Chemistry, College of Natural Sciences, Chosun University, Gwangju 501-759, Republic of Korea, bDepartment of Advanced Materials Chemistry, Korea University, Sejong Campus, Chungnam 339-700, Republic of Korea, and cReSEAT Program, Korea Institute of Science and Technology Information, 335 Eoeun-dong, Yuseong-gu, Daejeon 305-806, Republic of Korea
*Correspondence e-mail: sangok@korea.ac.kr

(Received 7 July 2011; accepted 20 July 2011; online 30 July 2011)

The title compound, [1-(CH3)3NCH2-1,2-C2B10H11]+·I or C6H22B10N+·I, was obtained by the reaction of (1,2-dicarba-closo-dodeca­boran­yl)dimethyl­methanamine with methyl iodide. The asymmetric unit contains two iodide anions and two (o-carboran­yl)tetra­methyl­ammonium cations. The bond lengths and angles in the carborane cage are within normal ranges, but the N—Cmethyl­ene—Ccage angle is very large [120.2 (2)°] because of repulsion between the carborane and tetra­methyl­ammonium units. In the crystal, ions are linked through C—H⋯I hydrogen bonds.

Related literature

For background to quaternaryammonium salts, see: Wiebcke & Felsche (2001[Wiebcke, M. & Felsche, J. (2001). Acta Cryst. C57, 306-308.]); Zhang et al. (2004[Zhang, H.-X., Zheng, S.-T. & Yang, G.-Y. (2004). Acta Cryst. C60, o545-o546.]); Carr et al. (2006[Carr, M. J., Franken, A., Macías, R. & Kennedy, J. D. (2006). Polyhedron, 25, 1069-1075.]). For background to o-carborane structures, see: Davidson et al. (1996[Davidson, M. G., Hibbert, T. G., Howard, J. A. K., Mackinnon, A. & Wade, K. (1996). Chem. Commun. pp. 2285-2286.]); Lee et al. (2000[Lee, J.-D., Kim, S.-J., Yoo, D., Ko, J., Cho, S. & Kang, S. O. (2000). Organometallics, 19, 1695-1703.]); Welch et al. (2001[Welch, A. J., Venkatasubramanian, U., Rosair, G. M., Ellis, D. & Donohoe, D. J. (2001). Acta Cryst. C57, 1295-1296.]). For a related structure, see: Lee et al. (1999[Lee, J.-D., Baek, C. K., Ko, J., Park, K., Cho, S., Min, S. K. & Kang, S. O. (1999). Organometallics, 18, 2189-2197.]).

[Scheme 1]

Experimental

Crystal data
  • C6H22B10N+·I

  • Mr = 343.25

  • Monoclinic, P 21 /n

  • a = 6.7435 (14) Å

  • b = 25.013 (5) Å

  • c = 18.694 (4) Å

  • β = 94.800 (4)°

  • V = 3142.2 (11) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 2.01 mm−1

  • T = 293 K

  • 0.28 × 0.25 × 0.20 mm

Data collection
  • Bruker SMART 1000 CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) Tmin = 0.603, Tmax = 0.689

  • 32138 measured reflections

  • 7772 independent reflections

  • 5834 reflections with I > 2σ(I)

  • Rint = 0.032

Refinement
  • R[F2 > 2σ(F2)] = 0.031

  • wR(F2) = 0.076

  • S = 1.02

  • 7772 reflections

  • 325 parameters

  • H-atom parameters constrained

  • Δρmax = 0.88 e Å−3

  • Δρmin = −0.92 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯I1 1.10 3.03 3.946 (3) 141
C3—H3B⋯I1 0.97 2.94 3.904 (3) 172
C23—H23B⋯I1 0.97 2.96 3.921 (3) 170

Data collection: SMART (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT-Plus (Bruker, 1999[Bruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]); software used to prepare material for publication: SHELXL97.

Supporting information


Comment top

N,N-dimethyl-(1,2-dicarba-closo-dodecaboranyl)methanamine is a useful intramolecular coordinating ligand for many different metals (Lee et al., 1999, 2000). Since the starting material is an oil, it could not be characterized by X-ray diffraction. However, we found that the corresponding methyl iodide forms crystals suitable for crystallographic study. We report here the synthesis and structure of the title compound (I).

In (I), shown in Fig. 1 and Table 1, the average bond length N—C [1.508 (2) Å] in the tetramethylammonium unit is similar to 1.492 (5) Å in an o-carboranyl organogallium compound [Cl3Ga][N(CH3)2CH2-1,2-C2B10H11] (Lee et al., 1999), 1.505 (2) Å in a benzyltrimethylammonium hydroxide trihydrate system (Wiebcke & Felsche, 2001) and 1.478 (5) Å in a tetramethylammonium pentaborate 0.25-hydrate compound (Zhang et al., 2004).

The average bond angle of Ccage—Cmethylene—N [120.3 (1)°] in (I) is almost same as 120.5 (6)° of o-carboranyl organogallium compound (Lee et al., 1999). Their large difference from the tetrahedral angle might be attributable to the repulsion between the carborane and tetramethylammonium unit. On the other hand, Carr and co-workers reported far smaller angle [113.5 (2)°] for the same methylene unit of [H3NCH2C2B10H11][H3CCH2CB11H11] with a smaller methylammonium unit than tetramethylammonium one. Compared with these two values, it would seem the above-mentioned repulsion logic would be affirmatively accepted.

The carborane moiety forms an icosahedrons consisting of twenty triangles with sides of the average bond length of Ccage—Ccage 1.659 (3), Ccage—Bcage 1.713 (1), and Bcage—Bcage 1.771 (1) Å. All of the compounds containing mono-substituted o-carboranes (Lee et al., 1999; Welch, et al., 2001) including unsubstituted ortho-, meta-, and para-carboranes with hexamethylphosphoramide (Davidson, et al., 1996) surveyed by our group so far exhibit the same trend of d(Ccage—Ccage) < d(Ccage—Bcage) < d(Bcage—Bcage). Since the boron atom has one valence electron less than carbon, this result confirms that the bond lengths will become shorter when more electrons participate in bond formation.

As shown in Table 1 and Figure 1, I1 atom participates in two intramolecular and an intermolecular hydrogen bonds, while I2 atom has only weak interaction with the closest interatomic distances I2···H3Ai 3.126 Å and I2···H5Aii 3.126 Å [symmetry code: (i) 0.5 - x, 1/2 + y, 1.5 - z; (ii) -1/2 + x, 1.5 - y, 1/2 + z]. The shortest interdimer's distance B26···H24iii 2.912 Å [symmetry code: (iii) -1 + x, y, z] suggests the dimer's packing of (I) is governed by van der Waals forces.

Related literature top

For background to quaternaryammonium salts, see: Wiebcke & Felsche (2001); Zhang et al. (2004); Carr et al. (2006). For background to o-carborane structures, see: Davidson et al. (1996); Lee et al. (2000); Welch et al. (2001). For a related structure, see: Lee et al. (1999).

Experimental top

A mixture of N,N-dimethyl-(1,2-dicarba-closo-dodecaboranyl)methanamine (0.2 g, 1.0 mmol) and 1.2 equiv of methyl iodide (0.17 g, 1.2 mmol) was dissolved in distilled diethyl ether (10 ml) and stirred at room temperature for 30 min. The resulting white solid was collected by filtration and washed with cold diethyl ether (quantitative yield, m.p. 389 K). The purity was checked by 1H, 13C, and 11B NMR spectroscopies. Suitable single crystals of (I) were obtained by recrystallization from acetone.

Refinement top

All of the hydrogen atoms were placed at idealized positions and treated using a riding model, with constrained distances and Uiso(H) values fixed at xUeq (parent atom) [C/B—H = 1.1 Å and x = 1.2 for carborane H atoms, C—H = 0.97 Å, and x = 1.2 for methylene H atoms, and C—H = 0.96 Å and x = 1.5 for methyl H atoms].

Computing details top

Data collection: SMART (Bruker, 1999); cell refinement: SAINT-Plus (Bruker, 1999); data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of (I), showing the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level, and H atoms (except for H2, H3B, and H23B) have been omitted for clarity. Dashed lines indicate intra- and intermolecular hydrogen bonds.
(1,2-Dicarba-closo-dodecaboranyl)trimethylmethanaminium iodide top
Crystal data top
C6H22B10N+·IF(000) = 1344
Mr = 343.25Dx = 1.451 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 5251 reflections
a = 6.7435 (14) Åθ = 2.3–27.3°
b = 25.013 (5) ŵ = 2.01 mm1
c = 18.694 (4) ÅT = 293 K
β = 94.800 (4)°Block, colourless
V = 3142.2 (11) Å30.28 × 0.25 × 0.20 mm
Z = 8
Data collection top
Bruker SMART 1000 CCD
diffractometer
7772 independent reflections
Radiation source: fine-focus sealed tube5834 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.032
ω scansθmax = 28.3°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
h = 88
Tmin = 0.603, Tmax = 0.689k = 3333
32138 measured reflectionsl = 2424
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.076H-atom parameters constrained
S = 1.02 w = 1/[σ2(Fo2) + (0.0267P)2 + 2.9488P]
where P = (Fo2 + 2Fc2)/3
7772 reflections(Δ/σ)max = 0.002
325 parametersΔρmax = 0.88 e Å3
0 restraintsΔρmin = 0.92 e Å3
Crystal data top
C6H22B10N+·IV = 3142.2 (11) Å3
Mr = 343.25Z = 8
Monoclinic, P21/nMo Kα radiation
a = 6.7435 (14) ŵ = 2.01 mm1
b = 25.013 (5) ÅT = 293 K
c = 18.694 (4) Å0.28 × 0.25 × 0.20 mm
β = 94.800 (4)°
Data collection top
Bruker SMART 1000 CCD
diffractometer
7772 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2008)
5834 reflections with I > 2σ(I)
Tmin = 0.603, Tmax = 0.689Rint = 0.032
32138 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0310 restraints
wR(F2) = 0.076H-atom parameters constrained
S = 1.02Δρmax = 0.88 e Å3
7772 reflectionsΔρmin = 0.92 e Å3
325 parameters
Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
I20.30391 (3)0.913655 (9)0.909132 (12)0.05540 (7)
I10.26909 (3)0.657927 (8)0.774753 (12)0.04975 (7)
N10.6119 (4)0.55189 (9)0.62825 (12)0.0392 (5)
B30.5023 (5)0.46207 (12)0.79957 (17)0.0363 (6)
H30.35590.44720.77790.044*
B40.7252 (5)0.44574 (12)0.76026 (17)0.0356 (6)
H40.72400.41980.71270.043*
B50.8919 (5)0.50059 (13)0.77262 (18)0.0385 (7)
H50.99930.51000.73330.046*
B60.7713 (5)0.55209 (13)0.81841 (17)0.0406 (7)
H60.79680.59480.80880.049*
B70.6790 (5)0.42083 (12)0.84662 (17)0.0404 (7)
H70.64930.37830.85590.048*
B80.5593 (5)0.47206 (13)0.89249 (18)0.0431 (7)
H80.44970.46350.93130.052*
B90.7252 (6)0.52692 (14)0.90438 (18)0.0462 (8)
H90.72270.55360.95110.055*
B100.9492 (6)0.51054 (15)0.86573 (19)0.0490 (8)
H101.09440.52620.88740.059*
B110.9206 (5)0.44426 (14)0.82976 (19)0.0449 (8)
H111.04740.41680.82810.054*
B120.8182 (6)0.46069 (14)0.91206 (18)0.0480 (8)
H120.87900.44400.96380.058*
C10.6407 (4)0.50998 (9)0.75779 (13)0.0307 (5)
C20.5473 (4)0.52448 (10)0.83484 (14)0.0373 (6)
H20.41980.55180.83560.045*
C30.5144 (4)0.53300 (10)0.69337 (14)0.0353 (6)
H3A0.41760.50600.67740.042*
H3B0.44060.56300.71060.042*
C40.7509 (5)0.59801 (12)0.64407 (18)0.0549 (8)
H4A0.79420.61160.59990.082*
H4B0.86430.58620.67440.082*
H4C0.68330.62570.66790.082*
C50.7167 (5)0.50697 (12)0.59283 (16)0.0512 (8)
H5A0.75910.51910.54780.077*
H5B0.62720.47730.58460.077*
H5C0.83050.49590.62350.077*
C60.4426 (5)0.57103 (14)0.57671 (17)0.0558 (8)
H6A0.37840.60090.59730.084*
H6B0.34830.54260.56760.084*
H6C0.49350.58180.53250.084*
N20.7834 (3)0.77280 (8)0.79247 (11)0.0325 (5)
B230.8766 (5)0.67804 (12)0.96808 (17)0.0367 (7)
H230.95690.64590.94260.044*
B240.9750 (5)0.74312 (13)0.97941 (17)0.0380 (7)
H241.12160.75340.96150.046*
B250.7765 (6)0.78988 (13)0.97298 (18)0.0479 (8)
H250.79420.83040.95140.058*
B260.5520 (5)0.75335 (18)0.9567 (2)0.0550 (10)
H260.42270.76950.92390.066*
B270.6239 (8)0.7764 (2)1.0435 (2)0.0782 (16)
H270.54110.80841.06820.094*
B280.8867 (7)0.76998 (15)1.05814 (19)0.0594 (11)
H280.97690.79791.09270.071*
B290.9465 (5)0.70112 (13)1.05485 (17)0.0389 (7)
H291.07500.68411.08720.047*
B300.7242 (5)0.66515 (15)1.03832 (18)0.0453 (8)
H300.70530.62441.05870.054*
B310.5269 (6)0.7114 (2)1.0320 (2)0.0712 (14)
H310.37970.70051.04880.085*
B320.7311 (6)0.72198 (17)1.09454 (19)0.0555 (10)
H320.71880.71881.15270.067*
C210.7687 (3)0.73285 (9)0.92250 (13)0.0281 (5)
C220.6242 (4)0.68780 (13)0.95729 (16)0.0488 (8)
H220.53520.66000.92210.059*
C230.7767 (4)0.72499 (9)0.84162 (13)0.0309 (5)
H23A0.89300.70330.83480.037*
H23B0.66130.70390.82480.037*
C240.6028 (4)0.80804 (11)0.79378 (16)0.0439 (7)
H24A0.48480.78690.78390.066*
H24B0.60740.83550.75800.066*
H24C0.60090.82420.84030.066*
C250.7839 (5)0.74947 (13)0.71782 (15)0.0486 (7)
H25A0.66460.72910.70700.073*
H25B0.89770.72660.71560.073*
H25C0.78990.77790.68360.073*
C260.9719 (4)0.80439 (12)0.80762 (16)0.0450 (7)
H26A0.97090.83450.77570.067*
H26B1.08430.78210.80040.067*
H26C0.98080.81680.85640.067*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
I20.05902 (14)0.04948 (13)0.05873 (14)0.00517 (10)0.01109 (10)0.00694 (10)
I10.04172 (11)0.04153 (11)0.06601 (14)0.00482 (8)0.00458 (9)0.00515 (9)
N10.0525 (14)0.0311 (11)0.0343 (12)0.0003 (10)0.0058 (10)0.0047 (9)
B30.0390 (16)0.0297 (14)0.0411 (17)0.0052 (12)0.0085 (13)0.0027 (12)
B40.0421 (17)0.0274 (14)0.0384 (16)0.0028 (12)0.0097 (13)0.0001 (12)
B50.0339 (16)0.0387 (16)0.0433 (17)0.0013 (13)0.0058 (13)0.0018 (13)
B60.0488 (19)0.0333 (15)0.0399 (17)0.0108 (13)0.0057 (14)0.0052 (13)
B70.0510 (19)0.0300 (15)0.0406 (17)0.0011 (13)0.0054 (14)0.0077 (13)
B80.054 (2)0.0395 (17)0.0371 (17)0.0033 (14)0.0116 (15)0.0043 (13)
B90.065 (2)0.0397 (17)0.0338 (17)0.0077 (16)0.0063 (15)0.0031 (13)
B100.048 (2)0.052 (2)0.0456 (19)0.0099 (16)0.0047 (15)0.0051 (16)
B110.0425 (18)0.0448 (18)0.0473 (19)0.0059 (14)0.0033 (15)0.0075 (15)
B120.060 (2)0.0464 (19)0.0371 (18)0.0033 (16)0.0004 (15)0.0065 (14)
C10.0362 (13)0.0259 (12)0.0307 (13)0.0020 (10)0.0070 (10)0.0003 (10)
C20.0451 (15)0.0326 (13)0.0357 (14)0.0003 (11)0.0122 (12)0.0015 (11)
C30.0398 (14)0.0322 (13)0.0344 (14)0.0025 (11)0.0058 (11)0.0013 (10)
C40.071 (2)0.0380 (16)0.0564 (19)0.0159 (15)0.0067 (16)0.0079 (14)
C50.071 (2)0.0469 (17)0.0379 (16)0.0065 (15)0.0173 (15)0.0019 (13)
C60.074 (2)0.0516 (18)0.0401 (17)0.0082 (16)0.0035 (15)0.0089 (14)
N20.0334 (11)0.0323 (11)0.0321 (11)0.0008 (9)0.0039 (9)0.0047 (9)
B230.0446 (17)0.0276 (14)0.0379 (16)0.0026 (12)0.0026 (13)0.0054 (12)
B240.0312 (15)0.0415 (17)0.0402 (17)0.0075 (12)0.0050 (12)0.0089 (13)
B250.072 (2)0.0325 (16)0.0386 (18)0.0116 (16)0.0014 (16)0.0033 (13)
B260.0347 (17)0.088 (3)0.0447 (19)0.0240 (18)0.0151 (15)0.0210 (19)
B270.103 (4)0.092 (3)0.043 (2)0.061 (3)0.026 (2)0.007 (2)
B280.097 (3)0.0415 (19)0.0372 (19)0.001 (2)0.0105 (19)0.0030 (15)
B290.0345 (16)0.0450 (18)0.0363 (16)0.0003 (13)0.0032 (13)0.0074 (13)
B300.0448 (18)0.053 (2)0.0371 (17)0.0124 (15)0.0004 (14)0.0158 (15)
B310.0376 (19)0.126 (4)0.053 (2)0.019 (2)0.0188 (17)0.039 (2)
B320.063 (2)0.073 (3)0.0321 (17)0.020 (2)0.0106 (16)0.0080 (17)
C210.0240 (11)0.0290 (12)0.0314 (12)0.0008 (9)0.0026 (9)0.0026 (10)
C220.0415 (16)0.065 (2)0.0392 (16)0.0214 (14)0.0028 (12)0.0161 (14)
C230.0347 (13)0.0274 (12)0.0307 (13)0.0005 (10)0.0035 (10)0.0020 (10)
C240.0394 (15)0.0400 (15)0.0521 (17)0.0115 (12)0.0030 (13)0.0123 (13)
C250.067 (2)0.0497 (17)0.0295 (14)0.0054 (15)0.0049 (13)0.0047 (12)
C260.0378 (15)0.0455 (16)0.0516 (17)0.0081 (12)0.0034 (13)0.0124 (13)
Geometric parameters (Å, º) top
N1—C41.500 (4)N2—C261.503 (3)
N1—C31.507 (3)N2—C241.505 (3)
N1—C51.510 (4)N2—C231.511 (3)
N1—C61.509 (4)N2—C251.513 (3)
B3—C21.712 (4)B23—C221.714 (4)
B3—C11.743 (4)B23—C211.741 (4)
B3—B71.756 (5)B23—B291.749 (4)
B3—B81.765 (5)B23—B301.763 (5)
B3—B41.775 (4)B23—B241.764 (4)
B3—H31.1000B23—H231.1000
B4—C11.704 (4)B24—C211.699 (4)
B4—B111.772 (5)B24—B281.766 (5)
B4—B51.776 (4)B24—B251.774 (5)
B4—B71.782 (4)B24—B291.782 (4)
B4—H41.1000B24—H241.1000
B5—C11.710 (4)B25—C211.709 (4)
B5—B101.769 (5)B25—B261.772 (6)
B5—B111.769 (5)B25—B281.771 (5)
B5—B61.780 (5)B25—B271.772 (6)
B5—H51.1000B25—H251.1000
B6—C21.712 (4)B26—C221.710 (5)
B6—C11.733 (4)B26—C211.722 (4)
B6—B101.767 (5)B26—B271.751 (6)
B6—B91.778 (5)B26—B311.774 (5)
B6—H61.1000B26—H261.1000
B7—B81.773 (5)B27—B311.757 (8)
B7—B121.783 (5)B27—B321.779 (6)
B7—B111.784 (5)B27—B281.778 (7)
B7—H71.1000B27—H271.1000
B8—C21.695 (4)B28—B321.768 (6)
B8—B91.773 (5)B28—B291.771 (5)
B8—B121.776 (5)B28—H281.1000
B8—H81.1000B29—B301.753 (5)
B9—C21.695 (5)B29—B321.765 (5)
B9—B121.773 (5)B29—H291.1000
B9—B101.776 (5)B30—C221.703 (4)
B9—H91.1000B30—B311.761 (6)
B10—B111.794 (5)B30—B321.766 (6)
B10—B121.793 (5)B30—H301.1000
B10—H101.1000B31—C221.699 (5)
B11—B121.786 (5)B31—B321.750 (6)
B11—H111.1000B31—H311.1000
B12—H121.1000B32—H321.1000
C1—C31.528 (4)C21—C231.530 (3)
C1—C21.660 (3)C21—C221.658 (4)
C2—H21.1000C22—H221.1000
C3—H3A0.9700C23—H23A0.9700
C3—H3B0.9700C23—H23B0.9700
C4—H4A0.9600C24—H24A0.9600
C4—H4B0.9600C24—H24B0.9600
C4—H4C0.9600C24—H24C0.9600
C5—H5A0.9600C25—H25A0.9600
C5—H5B0.9600C25—H25B0.9600
C5—H5C0.9600C25—H25C0.9600
C6—H6A0.9600C26—H26A0.9600
C6—H6B0.9600C26—H26B0.9600
C6—H6C0.9600C26—H26C0.9600
C4—N1—C3112.9 (2)C26—N2—C24111.2 (2)
C4—N1—C5110.5 (2)C26—N2—C23111.7 (2)
C3—N1—C5111.9 (2)C24—N2—C23112.83 (19)
C4—N1—C6108.0 (2)C26—N2—C25108.0 (2)
C3—N1—C6104.9 (2)C24—N2—C25107.8 (2)
C5—N1—C6108.2 (2)C23—N2—C25105.0 (2)
C2—B3—C157.41 (15)C22—B23—C2157.34 (16)
C2—B3—B7104.6 (2)C22—B23—B29104.5 (2)
C1—B3—B7105.2 (2)C21—B23—B29105.3 (2)
C2—B3—B858.33 (17)C22—B23—B3058.61 (18)
C1—B3—B8105.3 (2)C21—B23—B30105.2 (2)
B7—B3—B860.48 (19)B29—B23—B3059.89 (18)
C2—B3—B4103.9 (2)C22—B23—B24104.0 (2)
C1—B3—B457.94 (15)C21—B23—B2457.98 (15)
B7—B3—B460.62 (18)B29—B23—B2460.96 (18)
B8—B3—B4108.5 (2)B30—B23—B24108.4 (2)
C2—B3—H3125.1C22—B23—H23125.0
C1—B3—H3124.4C21—B23—H23124.4
B7—B3—H3122.5B29—B23—H23122.6
B8—B3—H3121.7B30—B23—H23121.8
B4—B3—H3122.3B24—B23—H23122.2
C1—B4—B360.09 (16)C21—B24—B2360.33 (16)
C1—B4—B11105.4 (2)C21—B24—B28105.3 (2)
B3—B4—B11107.7 (2)B23—B24—B28107.5 (2)
C1—B4—B558.79 (16)C21—B24—B2558.90 (17)
B3—B4—B5108.5 (2)B23—B24—B25109.0 (2)
B11—B4—B559.82 (18)B28—B24—B2560.0 (2)
C1—B4—B7105.7 (2)C21—B24—B29105.6 (2)
B3—B4—B759.15 (18)B23—B24—B2959.10 (17)
B11—B4—B760.25 (19)B28—B24—B2959.90 (19)
B5—B4—B7108.0 (2)B25—B24—B29108.2 (2)
C1—B4—H4123.7C21—B24—H24123.7
B3—B4—H4121.4B23—B24—H24121.2
B11—B4—H4122.4B28—B24—H24122.6
B5—B4—H4121.5B25—B24—H24121.1
B7—B4—H4122.4B29—B24—H24122.5
C1—B5—B10105.8 (2)C21—B25—B2659.24 (19)
C1—B5—B11105.3 (2)C21—B25—B28104.7 (2)
B10—B5—B1160.9 (2)B26—B25—B28107.3 (3)
C1—B5—B458.50 (16)C21—B25—B2458.36 (16)
B10—B5—B4108.7 (2)B26—B25—B24107.5 (2)
B11—B5—B459.96 (18)B28—B25—B2459.8 (2)
C1—B5—B659.51 (17)C21—B25—B27105.0 (3)
B10—B5—B659.7 (2)B26—B25—B2759.2 (3)
B11—B5—B6108.5 (2)B28—B25—B2760.2 (2)
B4—B5—B6108.2 (2)B24—B25—B27107.8 (2)
C1—B5—H5124.2C21—B25—H25124.4
B10—B5—H5121.7B26—B25—H25121.9
B11—B5—H5121.9B28—B25—H25122.5
B4—B5—H5121.5B24—B25—H25121.8
B6—B5—H5121.3B27—B25—H25122.4
C2—B6—C157.59 (15)C22—B26—C2157.77 (17)
C2—B6—B10104.2 (2)C22—B26—B27104.6 (3)
C1—B6—B10104.9 (2)C21—B26—B27105.3 (3)
C2—B6—B958.07 (18)C22—B26—B25104.8 (2)
C1—B6—B9105.0 (2)C21—B26—B2558.53 (17)
B10—B6—B960.1 (2)B27—B26—B2560.4 (3)
C2—B6—B5103.9 (2)C22—B26—B3158.3 (2)
C1—B6—B558.22 (16)C21—B26—B31105.0 (2)
B10—B6—B559.8 (2)B27—B26—B3159.8 (3)
B9—B6—B5107.5 (2)B25—B26—B31107.8 (3)
C2—B6—H6125.0C22—B26—H26124.5
C1—B6—H6124.2C21—B26—H26124.0
B10—B6—H6123.0B27—B26—H26122.8
B9—B6—H6122.2B25—B26—H26122.2
B5—B6—H6122.8B31—B26—H26122.3
B3—B7—B860.02 (18)B26—B27—B3160.8 (3)
B3—B7—B12108.1 (2)B26—B27—B2560.4 (2)
B8—B7—B1259.9 (2)B31—B27—B25108.6 (3)
B3—B7—B11108.1 (2)B26—B27—B32108.3 (3)
B8—B7—B11107.9 (2)B31—B27—B3259.3 (2)
B12—B7—B1160.1 (2)B25—B27—B32108.0 (3)
B3—B7—B460.23 (17)B26—B27—B28107.9 (3)
B8—B7—B4107.9 (2)B31—B27—B28107.0 (3)
B12—B7—B4107.7 (2)B25—B27—B2859.9 (2)
B11—B7—B459.58 (18)B32—B27—B2859.6 (2)
B3—B7—H7121.5B26—B27—H27121.2
B8—B7—H7121.8B31—B27—H27121.8
B12—B7—H7121.7B25—B27—H27121.3
B11—B7—H7121.8B32—B27—H27122.0
B4—B7—H7121.9B28—B27—H27122.4
C2—B8—B359.26 (17)B24—B28—B32108.4 (3)
C2—B8—B958.46 (18)B24—B28—B2560.21 (19)
B3—B8—B9108.4 (2)B32—B28—B25108.6 (3)
C2—B8—B7104.5 (2)B24—B28—B2960.50 (19)
B3—B8—B759.50 (18)B32—B28—B2959.8 (2)
B9—B8—B7108.2 (2)B25—B28—B29108.8 (2)
C2—B8—B12104.4 (2)B24—B28—B27107.9 (3)
B3—B8—B12108.0 (2)B32—B28—B2760.2 (3)
B9—B8—B1259.9 (2)B25—B28—B2759.9 (2)
B7—B8—B1260.3 (2)B29—B28—B27108.0 (3)
C2—B8—H8124.9B24—B28—H28121.5
B3—B8—H8121.3B32—B28—H28121.5
B9—B8—H8121.3B25—B28—H28121.3
B7—B8—H8122.4B29—B28—H28121.5
B12—B8—H8122.4B27—B28—H28121.9
C2—B9—B858.48 (18)B23—B29—B3060.46 (19)
C2—B9—B12104.6 (2)B23—B29—B32108.7 (2)
B8—B9—B1260.1 (2)B30—B29—B3260.3 (2)
C2—B9—B10104.5 (2)B23—B29—B28108.0 (2)
B8—B9—B10108.6 (2)B30—B29—B28108.2 (3)
B12—B9—B1060.7 (2)B32—B29—B2860.0 (2)
C2—B9—B659.03 (18)B23—B29—B2459.94 (17)
B8—B9—B6108.5 (2)B30—B29—B24108.1 (2)
B12—B9—B6108.5 (2)B32—B29—B24107.8 (2)
B10—B9—B659.65 (19)B28—B29—B2459.6 (2)
C2—B9—H9125.0B23—B29—H29121.4
B8—B9—H9121.2B30—B29—H29121.4
B12—B9—H9122.1B32—B29—H29121.5
B10—B9—H9122.2B28—B29—H29121.9
B6—B9—H9121.2B24—B29—H29122.0
B6—B10—B560.46 (18)C22—B30—B29104.8 (2)
B6—B10—B960.2 (2)C22—B30—B2359.26 (18)
B5—B10—B9108.0 (2)B29—B30—B2359.65 (18)
B6—B10—B11108.0 (2)C22—B30—B3158.7 (2)
B5—B10—B1159.54 (19)B29—B30—B31107.7 (3)
B9—B10—B11107.3 (2)B23—B30—B31108.3 (2)
B6—B10—B12108.0 (3)C22—B30—B32104.5 (3)
B5—B10—B12107.5 (2)B29—B30—B3260.2 (2)
B9—B10—B1259.6 (2)B23—B30—B32107.9 (2)
B11—B10—B1259.7 (2)B31—B30—B3259.5 (2)
B6—B10—H10121.3C22—B30—H30124.6
B5—B10—H10121.8B29—B30—H30122.5
B9—B10—H10122.0B23—B30—H30121.3
B11—B10—H10122.2B31—B30—H30121.6
B12—B10—H10122.0B32—B30—H30122.6
B5—B11—B460.22 (18)C22—B31—B32105.4 (2)
B5—B11—B7108.2 (2)C22—B31—B27104.9 (3)
B4—B11—B760.16 (18)B32—B31—B2761.0 (3)
B5—B11—B12107.8 (2)C22—B31—B3058.9 (2)
B4—B11—B12108.0 (2)B32—B31—B3060.4 (2)
B7—B11—B1259.93 (19)B27—B31—B30109.1 (3)
B5—B11—B1059.54 (19)C22—B31—B2659.0 (2)
B4—B11—B10107.8 (2)B32—B31—B26108.6 (3)
B7—B11—B10108.0 (2)B27—B31—B2659.5 (2)
B12—B11—B1060.1 (2)B30—B31—B26108.6 (2)
B5—B11—H11121.8C22—B31—H31124.6
B4—B11—H11121.6B32—B31—H31121.7
B7—B11—H11121.6B27—B31—H31122.0
B12—B11—H11121.7B30—B31—H31120.8
B10—B11—H11121.9B26—B31—H31121.4
B9—B12—B859.9 (2)B31—B32—B29107.7 (3)
B9—B12—B7107.7 (2)B31—B32—B3060.1 (2)
B8—B12—B759.76 (19)B29—B32—B3059.54 (19)
B9—B12—B11107.8 (2)B31—B32—B28107.7 (3)
B8—B12—B11107.7 (2)B29—B32—B2860.2 (2)
B7—B12—B1159.96 (19)B30—B32—B28107.7 (2)
B9—B12—B1059.8 (2)B31—B32—B2759.7 (3)
B8—B12—B10107.7 (2)B29—B32—B27108.2 (3)
B7—B12—B10108.0 (2)B30—B32—B27107.9 (3)
B11—B12—B1060.2 (2)B28—B32—B2760.1 (3)
B9—B12—H12121.9B31—B32—H32121.9
B8—B12—H12122.0B29—B32—H32121.8
B7—B12—H12121.8B30—B32—H32121.9
B11—B12—H12121.8B28—B32—H32121.7
B10—B12—H12121.7B27—B32—H32121.6
C3—C1—C2112.0 (2)C23—C21—C22111.8 (2)
C3—C1—B4122.7 (2)C23—C21—B24122.9 (2)
C2—C1—B4109.45 (19)C22—C21—B24109.54 (19)
C3—C1—B5131.2 (2)C23—C21—B25130.6 (2)
C2—C1—B5109.4 (2)C22—C21—B25110.0 (2)
B4—C1—B562.71 (17)B24—C21—B2562.74 (19)
C3—C1—B6120.4 (2)C23—C21—B26120.5 (2)
C2—C1—B660.57 (16)C22—C21—B2660.8 (2)
B4—C1—B6113.9 (2)B24—C21—B26113.5 (2)
B5—C1—B662.28 (18)B25—C21—B2662.2 (2)
C3—C1—B3109.2 (2)C23—C21—B23109.54 (19)
C2—C1—B360.35 (16)C22—C21—B2360.52 (17)
B4—C1—B361.97 (16)B24—C21—B2361.69 (17)
B5—C1—B3113.2 (2)B25—C21—B23113.2 (2)
B6—C1—B3112.8 (2)B26—C21—B23112.7 (2)
C1—C2—B9112.2 (2)C21—C22—B30111.9 (2)
C1—C2—B8112.4 (2)C21—C22—B31111.5 (3)
B9—C2—B863.06 (19)B30—C22—B3162.3 (2)
C1—C2—B661.84 (16)C21—C22—B2661.45 (18)
B9—C2—B662.90 (19)B30—C22—B26114.6 (3)
B8—C2—B6115.5 (2)B31—C22—B2662.7 (2)
C1—C2—B362.24 (16)C21—C22—B2362.14 (16)
B9—C2—B3114.8 (2)B30—C22—B2362.13 (19)
B8—C2—B362.41 (18)B31—C22—B23113.6 (2)
B6—C2—B3115.4 (2)B26—C22—B23114.6 (2)
C1—C2—H2120.0C21—C22—H22120.3
B9—C2—H2118.2B30—C22—H22118.5
B8—C2—H2118.0B31—C22—H22118.9
B6—C2—H2117.0B26—C22—H22117.5
B3—C2—H2117.3B23—C22—H22117.8
N1—C3—C1120.2 (2)N2—C23—C21120.3 (2)
N1—C3—H3A107.3N2—C23—H23A107.3
C1—C3—H3A107.3C21—C23—H23A107.3
N1—C3—H3B107.3N2—C23—H23B107.3
C1—C3—H3B107.3C21—C23—H23B107.3
H3A—C3—H3B106.9H23A—C23—H23B106.9
N1—C4—H4A109.5N2—C24—H24A109.5
N1—C4—H4B109.5N2—C24—H24B109.5
H4A—C4—H4B109.5H24A—C24—H24B109.5
N1—C4—H4C109.5N2—C24—H24C109.5
H4A—C4—H4C109.5H24A—C24—H24C109.5
H4B—C4—H4C109.5H24B—C24—H24C109.5
N1—C5—H5A109.5N2—C25—H25A109.5
N1—C5—H5B109.5N2—C25—H25B109.5
H5A—C5—H5B109.5H25A—C25—H25B109.5
N1—C5—H5C109.5N2—C25—H25C109.5
H5A—C5—H5C109.5H25A—C25—H25C109.5
H5B—C5—H5C109.5H25B—C25—H25C109.5
N1—C6—H6A109.5N2—C26—H26A109.5
N1—C6—H6B109.5N2—C26—H26B109.5
H6A—C6—H6B109.5H26A—C26—H26B109.5
N1—C6—H6C109.5N2—C26—H26C109.5
H6A—C6—H6C109.5H26A—C26—H26C109.5
H6B—C6—H6C109.5H26B—C26—H26C109.5
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···I11.103.033.946 (3)141
C3—H3B···I10.972.943.904 (3)172
C23—H23B···I10.972.963.921 (3)170

Experimental details

Crystal data
Chemical formulaC6H22B10N+·I
Mr343.25
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)6.7435 (14), 25.013 (5), 18.694 (4)
β (°) 94.800 (4)
V3)3142.2 (11)
Z8
Radiation typeMo Kα
µ (mm1)2.01
Crystal size (mm)0.28 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART 1000 CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2008)
Tmin, Tmax0.603, 0.689
No. of measured, independent and
observed [I > 2σ(I)] reflections
32138, 7772, 5834
Rint0.032
(sin θ/λ)max1)0.667
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.031, 0.076, 1.02
No. of reflections7772
No. of parameters325
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.88, 0.92

Computer programs: SMART (Bruker, 1999), SAINT-Plus (Bruker, 1999), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C2—H2···I11.103.033.946 (3)141.1
C3—H3B···I10.972.943.904 (3)171.9
C23—H23B···I10.972.963.921 (3)169.7
 

Acknowledgements

This study was supported by the research fund of Chosun University, 2010.

References

First citationBruker (1999). SMART and SAINT-Plus. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationCarr, M. J., Franken, A., Macías, R. & Kennedy, J. D. (2006). Polyhedron, 25, 1069–1075.  Web of Science CSD CrossRef CAS Google Scholar
First citationDavidson, M. G., Hibbert, T. G., Howard, J. A. K., Mackinnon, A. & Wade, K. (1996). Chem. Commun. pp. 2285–2286.  CSD CrossRef Web of Science Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationLee, J.-D., Baek, C. K., Ko, J., Park, K., Cho, S., Min, S. K. & Kang, S. O. (1999). Organometallics, 18, 2189–2197.  Web of Science CSD CrossRef CAS Google Scholar
First citationLee, J.-D., Kim, S.-J., Yoo, D., Ko, J., Cho, S. & Kang, S. O. (2000). Organometallics, 19, 1695–1703.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWelch, A. J., Venkatasubramanian, U., Rosair, G. M., Ellis, D. & Donohoe, D. J. (2001). Acta Cryst. C57, 1295–1296.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationWiebcke, M. & Felsche, J. (2001). Acta Cryst. C57, 306–308.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
First citationZhang, H.-X., Zheng, S.-T. & Yang, G.-Y. (2004). Acta Cryst. C60, o545–o546.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar

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