Cyclo-hexyldimethyl-ammonium tetra-hydroxy-penta-borate.

The title compound, [C(8)H(18)N](+)·[B(5)O(6)(OH)(4)](-), has been synthesized under mild solvothermal conditions in the presence of N,N-dimethyl-cyclo-hexyl-amine acting as a template. The structure consists of penta-borate [B(5)O(6)(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 [C(8)H(18)N](+) cations reside in the channels, inter-acting 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 = 346.32

Triclinic,

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[F 2 > 2σ(F 2)] = 0.044

wR(F 2) = 0.119

S = 1.08

3318 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.23 e Å−3

Δρmin = −0.29 e Å−3

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.

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

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

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C8H18N+·B5H4O10−	Z = 2
Mr = 346.32	F(000) = 364
Triclinic, P1	Dx = 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

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

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(Fo2) + (0.0587P)2 + 0.0744P] where P = (Fo2 + 2Fc2)/3
S = 1.08	(Δ/σ)max < 0.001
3318 reflections	Δρmax = 0.23 e Å−3
218 parameters	Δρmin = −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)

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
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*

	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)

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

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···O9iv	0.82	2.03	2.8477 (15)	178.
N1—H1D···O7	0.91	1.94	2.8368 (18)	169.

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⋯O9iv	0.82	2.03	2.8477 (15)	178
N1—H1D⋯O7	0.91	1.94	2.8368 (18)	169

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) .