Cyclo­hexyldimethyl­ammonium tetra­hydroxy­penta­borate

Li, H.; Wang, G.-M.; Xue, S.-Y.; Liang, Q.

doi:10.1107/S1600536808028869

metal-organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 64| Part 10| October 2008| Pages m1269-m1270

doi:10.1107/S1600536808028869

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Cyclohexyldimethylammonium tetrahydroxypentaborate

Hui Li,^a Guo-Ming Wang,^a ^* Shu-Yun Xue ^a and Qiang Liang ^a

^aDepartment of Chemistry, Teachers College of Qingdao University, Qingdao, Shandong 266071, People's Republic of China
^*Correspondence e-mail: gmwang_pub@163.com

(Received 30 August 2008; accepted 9 September 2008; online 17 September 2008)

The title compound, [C₈H₁₈N]⁺·[B₅O₆(OH)₄]⁻, has been synthesized under mild solvothermal conditions in the presence of N,N-dimethylcyclohexylamine acting as a template. The structure consists of pentaborate [B₅O₆(OH)₄]⁻ anions connected through O—H⋯O hydrogen bonds into a three-dimensional framework, with large channels along [100], [010] and [001] directions. The [C₈H₁₈N]⁺ cations reside in the channels, interacting with the framework through N—H⋯O hydrogen bonds.

Related literature

For related literature, see: Batsanov et al. (1982 ); Burns et al. (1995 ); Chen et al. (1995 ); Grice et al. (1999 ); Liu & Li (2006 ); Liu et al. (2006 ); Schubert et al. (2000 ); Touboul et al. (2003 ); Wang et al. (2004 , 2008a ,b )

Experimental

Crystal data

C₈H₁₈N⁺·B₅H₄O₁₀⁻
M_r = 346.32
Triclinic, $[P \overline 1]$
a = 8.6971 (4) Å
b = 9.8990 (2) Å
c = 10.2300 (3) Å
α = 74.591 (3)°
β = 74.442 (2)°
γ = 82.190 (5)°
V = 815.98 (5) Å³
Z = 2
Mo Kα radiation
μ = 0.12 mm⁻¹
T = 295 (2) K
0.45 × 0.45 × 0.45 mm

Data collection

Bruker SMART APEX area-detector diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ) T_min = 0.948, T_max = 0.949
6623 measured reflections
3318 independent reflections
2536 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.044
wR(F²) = 0.119
S = 1.08
3318 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.23 e Å⁻³
Δρ_min = −0.29 e Å⁻³

Table 1
Selected geometric parameters (Å, °)

B1—O1	1.350 (2)
B1—O5	1.3552 (19)
B1—O2	1.377 (2)
B2—O3	1.341 (2)
B2—O4	1.357 (2)
B2—O2	1.375 (2)
B3—O4	1.452 (2)
B3—O5	1.4651 (19)
B3—O6	1.469 (2)
B3—O7	1.473 (2)
B4—O10	1.346 (2)
B4—O7	1.3491 (19)
B4—O9	1.387 (2)
B5—O8	1.343 (2)
B5—O6	1.3439 (19)
B5—O9	1.388 (2)

O1—B1—O5	122.22 (15)
O1—B1—O2	117.10 (14)
O5—B1—O2	120.66 (14)
O3—B2—O4	121.91 (16)
O3—B2—O2	117.92 (15)
O4—B2—O2	120.14 (15)
O4—B3—O5	111.21 (12)
O4—B3—O6	108.43 (12)
O5—B3—O6	109.57 (13)
O4—B3—O7	108.58 (13)
O5—B3—O7	108.76 (12)
O6—B3—O7	110.28 (12)
O10—B4—O7	118.13 (15)
O10—B4—O9	121.04 (14)
O7—B4—O9	120.83 (14)
O8—B5—O6	123.78 (14)
O8—B5—O9	115.84 (14)
O6—B5—O9	120.38 (14)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1A⋯O5ⁱ	0.82	1.96	2.7759 (16)	174
O3—H3A⋯O4ⁱⁱ	0.82	1.99	2.8143 (16)	178
O8—H8A⋯O6ⁱⁱⁱ	0.82	1.96	2.7816 (15)	179
O10—H10A⋯O9^iv	0.82	2.03	2.8477 (15)	178
N1—H1D⋯O7	0.91	1.94	2.8368 (18)	169
Symmetry codes: (i) -x+1, -y+2, -z+1; (ii) -x, -y+2, -z+2; (iii) -x+1, -y+2, -z+2; (iv) -x+1, -y+1, -z+2.

Data collection: SMART (Bruker, 2002 ); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808028869/mg2056sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808028869/mg2056Isup2.hkl

checkCIF report

Comment top

Borate materials have been receiving particular attention due to their fascinating structural diversities and potential applications in mineralogy and industry (Burns et al., 1995; Chen et al., 1995; Grice et al., 1999; Touboul et al., 2003). From a structural point of view, the ability of B to adopt both BO₃ and BO₄ coordination modes, coupled with the tendency of such units to polymerize into a wide range of polyanions, has led to a rapidly growing family of borates. Thus far, numerous inorganic borate materials with alkali metals, alkaline earth metals, rare earths and transition metals have been extensively studied. In contrast, the analogous chemistry of organically templated borates is still relatively undeveloped. To the best of our knowledge, only a few examples with polyanions, such as [B₄O₅(OH)₄] (Batsanov et al., 1982), [B₅O₆(OH)₄] (Wang et al., 2004), [B₇O₉(OH)₅] (Liu & Li, 2006; Liu et al., 2006), [B₉O₁₂(OH)₆] (Schubert et al., 2000) and [B₁₄O₂₀(OH)₆] (Liu et al., 2006), have been reported. The aim of our work is to explore the construction of novel microporous aluminoborates templated by organic agents with different shape and size (Wang et al., 2008a,b). Unexpectedly, the title compound, (I), was isolated, a new organically templated pentaborate.

As shown in Fig. 1, the asymmetric unit of (I) contains one [B₅O₆(OH)₄]^- anion and one [C₈H₁₈N]⁺ cation. The anionic [B₅O₆(OH)₄]^- polyanion is composed of two common B₃O₃ rings, each containing two BO₃ triangles and one BO₄ tetrahedron. The B—O bond distances lie in the range 1.341 (2)–1.388 (2) Å for the BO₃ triangles (B1, B2, B4 and B5) and 1.452 (2)–1.473 (2) Å for the B(3)O₄ tetrahedron, in good agreement with those reported previously for other borate compounds. The O—B—O bond angles lie in the range 115.8 (2)–123.7 (2) ° for the triangles and 108.4 (2)–111.2 (2) ° for the tetrahedron. The anionic [B₅O₆(OH)₄]^- groups are connected to each other through intermolecular O—H···O hydrogen bonds, forming a three-dimensional framework with large channels along [100], [010] and [001] directions. The [C₈H₁₈N]⁺ cations reside in these channels, interacting with the framework through N—H···O hydrogen bonds (Fig. 2).

Related literature top

For related literature, see: Batsanov et al. (1982); Burns et al. (1995); Chen et al. (1995); Grice et al. (1999); Liu & Li (2006); Liu et al. (2006); Schubert et al. (2000); Touboul et al. (2003); Wang et al. (2004, 2008a,b)

Experimental top

A mixture of H₃BO₃ (0.186 g), Al₂O₃ (0.104 g), N,N-dimethylcyclohexylamine (0.75 ml), pyridine (4.4 ml) and H₂O (0.50 ml) was sealed in a Teflon-lined steel autoclave, heated at 453 K for 8 days, and then cooled to room temperature. The homogeneous product consisting of large colorless block-shaped crystals was separated from the solution by filtration, washed with distilled water, and then dried in air.

Computing details top

Data collection: SMART (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2002); data reduction: SAINT-Plus (Bruker, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of (I), with displacement ellipsoids drawn at the 50% probability level for non-H atoms.
	Fig. 2. Projection of (I) along b, showing [B₅O₆(OH)₄]^- anions linked into a three-dimensional framework, with [C₈H₁₈N]⁺ cations occupying channels. Hydrogen bonds are shown as dashed lines.

Cyclohexyldimethylammonium tetrahydroxypentaborate top

Crystal data top

C₈H₁₈N⁺·B₅H₄O¹⁰⁻	Z = 2
M_r = 346.32	F(000) = 364
Triclinic, P1	D_x = 1.410 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6971 (4) Å	Cell parameters from 6623 reflections
b = 9.8990 (2) Å	θ = 2.1–26.5°
c = 10.2300 (3) Å	µ = 0.12 mm⁻¹
α = 74.591 (3)°	T = 295 K
β = 74.442 (2)°	Block, colorless
γ = 82.190 (5)°	0.45 × 0.45 × 0.45 mm
V = 815.98 (5) Å³

Data collection top

Bruker SMART APEX area-detector diffractometer	3318 independent reflections
Radiation source: fine-focus sealed tube	2536 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.026
ϕ and ω scans	θ_max = 26.5°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→10
T_min = 0.949, T_max = 0.949	k = −12→12
6623 measured reflections	l = −12→12

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.044	H-atom parameters constrained
wR(F²) = 0.119	w = 1/[σ²(F_o²) + (0.0587P)² + 0.0744P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
3318 reflections	Δρ_max = 0.23 e Å⁻³
218 parameters	Δρ_min = −0.29 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.058 (6)

Crystal data top

C₈H₁₈N⁺·B₅H₄O¹⁰⁻	γ = 82.190 (5)°
M_r = 346.32	V = 815.98 (5) Å³
Triclinic, P1	Z = 2
a = 8.6971 (4) Å	Mo Kα radiation
b = 9.8990 (2) Å	µ = 0.12 mm⁻¹
c = 10.2300 (3) Å	T = 295 K
α = 74.591 (3)°	0.45 × 0.45 × 0.45 mm
β = 74.442 (2)°

Data collection top

Bruker SMART APEX area-detector diffractometer	3318 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2536 reflections with I > 2σ(I)
T_min = 0.949, T_max = 0.949	R_int = 0.026
6623 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.044	0 restraints
wR(F²) = 0.119	H-atom parameters constrained
S = 1.08	Δρ_max = 0.23 e Å⁻³
3318 reflections	Δρ_min = −0.29 e Å⁻³
218 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

	x	y	z	U_iso*/U_eq
B1	0.3071 (2)	1.10774 (18)	0.59941 (19)	0.0342 (4)
B2	0.1056 (2)	1.1184 (2)	0.8073 (2)	0.0372 (4)
B3	0.3133 (2)	0.92080 (17)	0.81503 (17)	0.0296 (4)
B4	0.3702 (2)	0.66200 (18)	0.88838 (18)	0.0309 (4)
B5	0.5114 (2)	0.81317 (18)	0.95617 (18)	0.0311 (4)
O1	0.35979 (15)	1.16205 (12)	0.46086 (12)	0.0477 (3)
H1A	0.4376	1.1133	0.4291	0.072*
O2	0.17524 (14)	1.17636 (12)	0.66942 (12)	0.0480 (3)
O3	−0.02096 (16)	1.18988 (13)	0.87215 (13)	0.0555 (4)
H3A	−0.0641	1.1391	0.9470	0.083*
O4	0.16229 (13)	0.99089 (11)	0.87271 (11)	0.0362 (3)
O5	0.37677 (12)	0.98883 (11)	0.66764 (10)	0.0328 (3)
O6	0.42790 (13)	0.92583 (10)	0.89591 (11)	0.0334 (3)
O7	0.28642 (13)	0.77398 (10)	0.82604 (11)	0.0331 (3)
O8	0.61961 (15)	0.82028 (12)	1.02584 (13)	0.0454 (3)
H8A	0.6045	0.8953	1.0486	0.068*
O9	0.48965 (13)	0.67959 (11)	0.94784 (12)	0.0375 (3)
O10	0.33377 (15)	0.53291 (11)	0.89197 (13)	0.0453 (3)
H10A	0.3859	0.4736	0.9386	0.068*
C2	0.2698 (4)	0.5351 (3)	0.4335 (3)	0.0907 (9)
H2A	0.3327	0.4461	0.4360	0.109*
H2B	0.1854	0.5349	0.3880	0.109*
C1	0.3752 (4)	0.6525 (3)	0.3495 (3)	0.0884 (8)
H1B	0.4659	0.6475	0.3892	0.106*
H1C	0.4156	0.6425	0.2542	0.106*
C4	0.1958 (3)	0.5485 (2)	0.5814 (2)	0.0685 (6)
H4A	0.1248	0.4738	0.6301	0.082*
H4B	0.2793	0.5392	0.6304	0.082*
C3	0.2836 (3)	0.7915 (3)	0.3491 (2)	0.0677 (6)
H3B	0.2010	0.8008	0.2990	0.081*
H3C	0.3552	0.8659	0.3005	0.081*
C5	0.2074 (3)	0.8069 (2)	0.4963 (2)	0.0552 (5)
H5A	0.2908	0.8097	0.5421	0.066*
H5B	0.1428	0.8952	0.4922	0.066*
C6	0.1036 (2)	0.6880 (2)	0.58154 (18)	0.0464 (4)
H6A	0.0141	0.6920	0.5391	0.056*
C7	−0.0497 (3)	0.5880 (3)	0.8280 (3)	0.0899 (9)
H7A	−0.0881	0.6078	0.9185	0.135*
H7B	0.0219	0.5050	0.8341	0.135*
H7D	−0.1386	0.5732	0.7956	0.135*
C8	−0.0711 (3)	0.8397 (3)	0.7322 (3)	0.0774 (7)
H8B	−0.1092	0.8485	0.8270	0.116*
H8E	−0.1603	0.8354	0.6953	0.116*
H8C	−0.0124	0.9194	0.6767	0.116*
N1	0.03619 (19)	0.70824 (19)	0.72858 (16)	0.0540 (4)
H1D	0.1208	0.7174	0.7614	0.065*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
B1	0.0377 (10)	0.0291 (9)	0.0329 (9)	0.0001 (8)	−0.0099 (8)	−0.0021 (7)
B2	0.0364 (10)	0.0328 (10)	0.0367 (10)	0.0043 (8)	−0.0081 (8)	−0.0027 (8)
B3	0.0345 (9)	0.0252 (8)	0.0286 (9)	0.0013 (7)	−0.0110 (7)	−0.0038 (7)
B4	0.0346 (9)	0.0268 (9)	0.0308 (9)	−0.0004 (7)	−0.0100 (7)	−0.0050 (7)
B5	0.0318 (9)	0.0298 (9)	0.0316 (9)	0.0026 (7)	−0.0096 (7)	−0.0075 (7)
O1	0.0515 (8)	0.0430 (7)	0.0336 (6)	0.0102 (6)	−0.0047 (5)	0.0038 (5)
O2	0.0495 (8)	0.0379 (7)	0.0381 (7)	0.0151 (5)	−0.0026 (5)	0.0048 (5)
O3	0.0515 (8)	0.0468 (8)	0.0467 (7)	0.0198 (6)	0.0006 (6)	0.0008 (6)
O4	0.0361 (6)	0.0325 (6)	0.0319 (6)	0.0059 (5)	−0.0056 (5)	−0.0010 (5)
O5	0.0364 (6)	0.0296 (6)	0.0284 (6)	0.0036 (4)	−0.0073 (4)	−0.0037 (4)
O6	0.0422 (6)	0.0247 (5)	0.0361 (6)	0.0024 (5)	−0.0179 (5)	−0.0062 (4)
O7	0.0372 (6)	0.0274 (6)	0.0370 (6)	−0.0002 (5)	−0.0177 (5)	−0.0037 (4)
O8	0.0540 (8)	0.0337 (6)	0.0605 (8)	0.0078 (5)	−0.0354 (6)	−0.0155 (5)
O9	0.0439 (7)	0.0248 (6)	0.0496 (7)	0.0050 (5)	−0.0261 (5)	−0.0076 (5)
O10	0.0546 (8)	0.0262 (6)	0.0614 (8)	−0.0016 (5)	−0.0320 (6)	−0.0036 (5)
C2	0.130 (2)	0.0621 (16)	0.0858 (19)	0.0030 (16)	−0.0256 (18)	−0.0321 (14)
C1	0.0910 (19)	0.101 (2)	0.0638 (15)	0.0082 (16)	−0.0015 (14)	−0.0295 (15)
C4	0.0907 (17)	0.0440 (12)	0.0684 (15)	−0.0043 (11)	−0.0254 (13)	−0.0035 (10)
C3	0.0751 (15)	0.0731 (15)	0.0487 (12)	−0.0154 (12)	−0.0111 (11)	−0.0032 (11)
C5	0.0682 (13)	0.0471 (11)	0.0508 (11)	−0.0127 (10)	−0.0154 (10)	−0.0073 (9)
C6	0.0485 (11)	0.0532 (11)	0.0407 (10)	−0.0104 (9)	−0.0183 (8)	−0.0055 (8)
C7	0.0835 (18)	0.125 (2)	0.0532 (14)	−0.0480 (17)	−0.0113 (13)	0.0068 (14)
C8	0.0516 (13)	0.110 (2)	0.0765 (16)	0.0118 (13)	−0.0205 (12)	−0.0362 (15)
N1	0.0436 (9)	0.0767 (12)	0.0442 (9)	−0.0127 (8)	−0.0178 (7)	−0.0071 (8)

Geometric parameters (Å, º) top

B1—O1	1.350 (2)	C1—C3	1.492 (4)
B1—O5	1.3552 (19)	C1—H1B	0.9700
B1—O2	1.377 (2)	C1—H1C	0.9700
B2—O3	1.341 (2)	C4—C6	1.500 (3)
B2—O4	1.357 (2)	C4—H4A	0.9700
B2—O2	1.375 (2)	C4—H4B	0.9700
B3—O4	1.452 (2)	C3—C5	1.513 (3)
B3—O5	1.4651 (19)	C3—H3B	0.9700
B3—O6	1.469 (2)	C3—H3C	0.9700
B3—O7	1.473 (2)	C5—C6	1.510 (3)
B4—O10	1.346 (2)	C5—H5A	0.9700
B4—O7	1.3491 (19)	C5—H5B	0.9700
B4—O9	1.387 (2)	C6—N1	1.517 (2)
B5—O8	1.343 (2)	C6—H6A	0.9800
B5—O6	1.3439 (19)	C7—N1	1.484 (3)
B5—O9	1.388 (2)	C7—H7A	0.9600
O1—H1A	0.8200	C7—H7B	0.9600
O3—H3A	0.8200	C7—H7D	0.9600
O8—H8A	0.8200	C8—N1	1.497 (3)
O10—H10A	0.8200	C8—H8B	0.9600
C2—C1	1.506 (4)	C8—H8E	0.9600
C2—C4	1.510 (3)	C8—H8C	0.9600
C2—H2A	0.9700	N1—H1D	0.9100
C2—H2B	0.9700

O1—B1—O5	122.22 (15)	C6—C4—H4A	109.5
O1—B1—O2	117.10 (14)	C2—C4—H4A	109.5
O5—B1—O2	120.66 (14)	C6—C4—H4B	109.5
O3—B2—O4	121.91 (16)	C2—C4—H4B	109.5
O3—B2—O2	117.92 (15)	H4A—C4—H4B	108.1
O4—B2—O2	120.14 (15)	C1—C3—C5	111.33 (19)
O4—B3—O5	111.21 (12)	C1—C3—H3B	109.4
O4—B3—O6	108.43 (12)	C5—C3—H3B	109.4
O5—B3—O6	109.57 (13)	C1—C3—H3C	109.4
O4—B3—O7	108.58 (13)	C5—C3—H3C	109.4
O5—B3—O7	108.76 (12)	H3B—C3—H3C	108.0
O6—B3—O7	110.28 (12)	C6—C5—C3	112.21 (17)
O10—B4—O7	118.13 (15)	C6—C5—H5A	109.2
O10—B4—O9	121.04 (14)	C3—C5—H5A	109.2
O7—B4—O9	120.83 (14)	C6—C5—H5B	109.2
O8—B5—O6	123.78 (14)	C3—C5—H5B	109.2
O8—B5—O9	115.84 (14)	H5A—C5—H5B	107.9
O6—B5—O9	120.38 (14)	C4—C6—C5	110.93 (18)
B1—O1—H1A	109.5	C4—C6—N1	111.82 (15)
B2—O2—B1	119.89 (13)	C5—C6—N1	109.11 (15)
B2—O3—H3A	109.5	C4—C6—H6A	108.3
B2—O4—B3	123.53 (13)	C5—C6—H6A	108.3
B1—O5—B3	123.25 (13)	N1—C6—H6A	108.3
B5—O6—B3	124.60 (12)	N1—C7—H7A	109.5
B4—O7—B3	123.84 (12)	N1—C7—H7B	109.5
B5—O8—H8A	109.5	H7A—C7—H7B	109.5
B4—O9—B5	119.28 (12)	N1—C7—H7D	109.5
B4—O10—H10A	109.5	H7A—C7—H7D	109.5
C1—C2—C4	112.3 (2)	H7B—C7—H7D	109.5
C1—C2—H2A	109.1	N1—C8—H8B	109.5
C4—C2—H2A	109.1	N1—C8—H8E	109.5
C1—C2—H2B	109.1	H8B—C8—H8E	109.5
C4—C2—H2B	109.1	N1—C8—H8C	109.5
H2A—C2—H2B	107.9	H8B—C8—H8C	109.5
C3—C1—C2	110.5 (2)	H8E—C8—H8C	109.5
C3—C1—H1B	109.6	C7—N1—C8	108.9 (2)
C2—C1—H1B	109.6	C7—N1—C6	114.16 (19)
C3—C1—H1C	109.6	C8—N1—C6	112.63 (16)
C2—C1—H1C	109.6	C7—N1—H1D	106.9
H1B—C1—H1C	108.1	C8—N1—H1D	106.9
C6—C4—C2	110.61 (18)	C6—N1—H1D	106.9

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5ⁱ	0.82	1.96	2.7759 (16)	174
O3—H3A···O4ⁱⁱ	0.82	1.99	2.8143 (16)	178
O8—H8A···O6ⁱⁱⁱ	0.82	1.96	2.7816 (15)	179
O10—H10A···O9^iv	0.82	2.03	2.8477 (15)	178
N1—H1D···O7	0.91	1.94	2.8368 (18)	169

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) −x+1, −y+1, −z+2.

Experimental details

Crystal data
Chemical formula	C₈H₁₈N⁺·B₅H₄O¹⁰⁻
M_r	346.32
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	8.6971 (4), 9.8990 (2), 10.2300 (3)
α, β, γ (°)	74.591 (3), 74.442 (2), 82.190 (5)
V (Å³)	815.98 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.12
Crystal size (mm)	0.45 × 0.45 × 0.45

Data collection
Diffractometer	Bruker SMART APEX area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.949, 0.949
No. of measured, independent and observed [I > 2σ(I)] reflections	6623, 3318, 2536
R_int	0.026
(sin θ/λ)_max (Å⁻¹)	0.628

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.044, 0.119, 1.08
No. of reflections	3318
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.23, −0.29

Computer programs: SMART (Bruker, 2002), SAINT-Plus (Bruker, 2002), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

B1—O1	1.350 (2)	B3—O6	1.469 (2)
B1—O5	1.3552 (19)	B3—O7	1.473 (2)
B1—O2	1.377 (2)	B4—O10	1.346 (2)
B2—O3	1.341 (2)	B4—O7	1.3491 (19)
B2—O4	1.357 (2)	B4—O9	1.387 (2)
B2—O2	1.375 (2)	B5—O8	1.343 (2)
B3—O4	1.452 (2)	B5—O6	1.3439 (19)
B3—O5	1.4651 (19)	B5—O9	1.388 (2)

O1—B1—O5	122.22 (15)	O4—B3—O7	108.58 (13)
O1—B1—O2	117.10 (14)	O5—B3—O7	108.76 (12)
O5—B1—O2	120.66 (14)	O6—B3—O7	110.28 (12)
O3—B2—O4	121.91 (16)	O10—B4—O7	118.13 (15)
O3—B2—O2	117.92 (15)	O10—B4—O9	121.04 (14)
O4—B2—O2	120.14 (15)	O7—B4—O9	120.83 (14)
O4—B3—O5	111.21 (12)	O8—B5—O6	123.78 (14)
O4—B3—O6	108.43 (12)	O8—B5—O9	115.84 (14)
O5—B3—O6	109.57 (13)	O6—B5—O9	120.38 (14)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O5ⁱ	0.82	1.96	2.7759 (16)	173.5
O3—H3A···O4ⁱⁱ	0.82	1.99	2.8143 (16)	177.6
O8—H8A···O6ⁱⁱⁱ	0.82	1.96	2.7816 (15)	178.9
O10—H10A···O9^iv	0.82	2.03	2.8477 (15)	177.6
N1—H1D···O7	0.91	1.94	2.8368 (18)	169.2

Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) −x, −y+2, −z+2; (iii) −x+1, −y+2, −z+2; (iv) −x+1, −y+1, −z+2.

Acknowledgements

This work was supported by the Qingdao University Research Fund (No. 063–06300522).

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