2-Aza-niumylcarba-closo-dodeca-borate ethanol monosolvate.

Two formula units of the title compound, 2-H(3)N-closo-1-CB(11)H(11)·CH(3)CH(2)OH or CH(14)B(11)N·C(2)H(5)OH, form a ring motif of R(4) (2)(8) type in the solid state that surrounds a crystallographic center of symmetry. The ring motif is a result of N-H⋯O hydrogen bonds. In contrast to many structures of {closo-1-CB(11)} clusters, the assignment of the position of the cluster C atom in the structure of the title compound is unambigious. The relatively long B-N bond length [1.5396 (10) Å] documents the absence of any B-N π-inter-action in the title compound although this was observed for a related 2-amino-carba-closo-dodeca-borate.

Related literature

For a general overview on monocarba-closo-dodeca­borates, see: Körbe et al. (2006 ▶). For the synthesis and properties of 2-amino- and 2-azaniumyl­carba-closo-dodeca­boron clusters, see: Finze (2009 ▶). For structures and properties of related {closo-1-CB11} clusters with NH2 and NH3 groups, see: Jelínek et al. (1986 ▶); Finze (2007 ▶); Finze et al. (2007 ▶); Finze & Sprenger (2010 ▶). For hydrogen-bond motifs, see: Etter (1990 ▶).

Experimental

Crystal data

CH14B11N·C2H6O

M = 205.11

Monoclinic,

a = 9.5753 (2) Å

b = 9.2549 (2) Å

c = 13.9095 (5) Å

β = 97.519 (3)°

V = 1222.04 (6) Å3

Z = 4

Mo Kα radiation

μ = 0.06 mm−1

T = 120 K

0.28 × 0.26 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.729, T max = 1.000

61096 measured reflections

3561 independent reflections

3199 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 60 min intensity decay: none

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.069

S = 1.02

3561 reflections

208 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.31 e Å−3

Δρmin = −0.22 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: DIAMOND (Brandenburg, 2011) ▶; software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811006222/br2161sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811006222/br2161Isup2.hkl

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

CH14B11N·C2H6O	F(000) = 432
Mr = 205.11	Dx = 1.115 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 48838 reflections
a = 9.5753 (2) Å	θ = 3.0–35.4°
b = 9.2549 (2) Å	µ = 0.06 mm−1
c = 13.9095 (5) Å	T = 120 K
β = 97.519 (3)°	Block, colourless
V = 1222.04 (6) Å3	0.28 × 0.26 × 0.20 mm
Z = 4

Oxford Diffraction Xcalibur Eos diffractometer	3199 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 30.0°, θmin = 4.3°
ω scans	h = −13→13
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −13→13
Tmin = 0.729, Tmax = 1.000	l = −19→19
61096 measured reflections	3 standard reflections every 60 min
3561 independent reflections	intensity decay: none

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)] = 0.029	Hydrogen site location: difference Fourier map
wR(F2) = 0.069	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ2(Fo2) + 0.6P] where P = (Fo2 + 2Fc2)/3
3561 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.31 e Å−3
0 restraints	Δρmin = −0.22 e Å−3

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06–11-2009). Numerical absorption correction based on Gaussian integration over a multifaceted crystal model..

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
C1	0.64079 (8)	0.84830 (8)	0.78113 (5)	0.01344 (14)
H1	0.5827 (11)	0.9122 (12)	0.8122 (7)	0.018 (3)*
B2	0.80596 (8)	0.81753 (9)	0.83584 (6)	0.01164 (14)
N1	0.85434 (7)	0.89268 (8)	0.93327 (5)	0.01414 (13)
H1A	0.9385 (13)	0.8604 (13)	0.9609 (8)	0.027 (3)*
H1B	0.8607 (12)	0.9893 (14)	0.9280 (8)	0.026 (3)*
H1C	0.7976 (12)	0.8764 (13)	0.9748 (8)	0.024 (3)*
B3	0.67585 (9)	0.68137 (9)	0.83322 (6)	0.01329 (15)
H3	0.6339 (11)	0.6570 (11)	0.8994 (7)	0.018 (3)*
B4	0.56348 (9)	0.70103 (10)	0.72203 (6)	0.01463 (16)
H4	0.4514 (11)	0.6832 (12)	0.7204 (8)	0.022 (3)*
B5	0.62540 (9)	0.85015 (9)	0.65759 (6)	0.01452 (16)
H5	0.5509 (11)	0.9214 (12)	0.6171 (7)	0.019 (3)*
B6	0.77708 (9)	0.92320 (9)	0.72901 (6)	0.01289 (15)
H6	0.7950 (11)	1.0393 (11)	0.7353 (7)	0.019 (3)*
B7	0.84826 (8)	0.63822 (9)	0.80794 (6)	0.01176 (14)
H7	0.9196 (11)	0.5751 (12)	0.8583 (7)	0.019 (3)*
B8	0.69640 (9)	0.56516 (9)	0.73553 (6)	0.01280 (15)
H8	0.6694 (11)	0.4511 (12)	0.7382 (7)	0.020 (3)*
B9	0.66519 (9)	0.66986 (9)	0.62665 (6)	0.01348 (15)
H9	0.6180 (11)	0.6216 (12)	0.5578 (7)	0.019 (3)*
B10	0.79711 (9)	0.80728 (9)	0.63111 (6)	0.01288 (15)
H10	0.8360 (11)	0.8478 (11)	0.5659 (7)	0.018 (3)*
B11	0.91068 (8)	0.78779 (9)	0.74285 (6)	0.01167 (15)
H11	1.0217 (11)	0.8179 (11)	0.7508 (8)	0.019 (3)*
B12	0.84085 (8)	0.63102 (9)	0.67959 (6)	0.01164 (14)
H12	0.9092 (11)	0.5566 (11)	0.6440 (7)	0.017 (2)*
O1	0.88753 (6)	1.20322 (7)	0.94495 (5)	0.01863 (12)
H1O	0.9206 (15)	1.2323 (16)	0.9014 (10)	0.045 (4)*
C2	0.78862 (9)	1.30879 (9)	0.97377 (6)	0.02120 (17)
H2A	0.7249	1.3401	0.9176	0.035 (2)*
H2B	0.8390	1.3926	1.0021	0.035 (2)*
C3	0.70730 (10)	1.23985 (10)	1.04632 (7)	0.02545 (19)
H3A	0.7713	1.2070	1.1008	0.043 (2)*
H3B	0.6550	1.1592	1.0170	0.043 (2)*
H3C	0.6435	1.3092	1.0677	0.043 (2)*

	U11	U22	U33	U12	U13	U23
C1	0.0119 (3)	0.0125 (3)	0.0161 (3)	0.0009 (3)	0.0025 (3)	−0.0011 (3)
B2	0.0120 (3)	0.0121 (3)	0.0109 (3)	−0.0006 (3)	0.0020 (3)	−0.0010 (3)
N1	0.0162 (3)	0.0148 (3)	0.0116 (3)	−0.0014 (2)	0.0026 (2)	−0.0018 (2)
B3	0.0134 (3)	0.0129 (4)	0.0140 (3)	−0.0008 (3)	0.0036 (3)	−0.0005 (3)
B4	0.0116 (3)	0.0141 (4)	0.0181 (4)	−0.0007 (3)	0.0016 (3)	−0.0019 (3)
B5	0.0141 (4)	0.0135 (4)	0.0153 (4)	0.0017 (3)	−0.0007 (3)	−0.0001 (3)
B6	0.0140 (3)	0.0113 (3)	0.0134 (3)	−0.0001 (3)	0.0021 (3)	0.0003 (3)
B7	0.0123 (3)	0.0114 (3)	0.0118 (3)	0.0001 (3)	0.0022 (3)	0.0007 (3)
B8	0.0130 (3)	0.0117 (3)	0.0139 (3)	−0.0011 (3)	0.0026 (3)	−0.0005 (3)
B9	0.0139 (3)	0.0128 (4)	0.0133 (3)	0.0002 (3)	0.0002 (3)	−0.0010 (3)
B10	0.0151 (4)	0.0119 (3)	0.0116 (3)	0.0003 (3)	0.0016 (3)	0.0005 (3)
B11	0.0118 (3)	0.0117 (3)	0.0117 (3)	−0.0005 (3)	0.0024 (3)	0.0000 (3)
B12	0.0124 (3)	0.0111 (3)	0.0115 (3)	0.0004 (3)	0.0022 (3)	0.0000 (3)
O1	0.0193 (3)	0.0187 (3)	0.0190 (3)	0.0011 (2)	0.0069 (2)	0.0008 (2)
C2	0.0232 (4)	0.0159 (4)	0.0251 (4)	0.0040 (3)	0.0055 (3)	0.0024 (3)
C3	0.0242 (4)	0.0254 (4)	0.0286 (4)	0.0045 (3)	0.0108 (3)	0.0023 (4)

C1—B2	1.6872 (11)	B5—B6	1.7821 (12)
C1—B3	1.7207 (12)	B5—H5	1.075 (10)
C1—B4	1.7094 (12)	B6—B10	1.7636 (12)
C1—B5	1.7055 (12)	B6—B11	1.7832 (12)
C1—B6	1.7196 (11)	B6—H6	1.090 (11)
C1—H1	0.953 (10)	B7—B12	1.7787 (11)
B2—N1	1.5396 (10)	B7—B8	1.7896 (12)
B2—B11	1.7589 (11)	B7—B11	1.7985 (12)
B2—B7	1.7634 (12)	B7—H7	1.083 (10)
B2—B3	1.7691 (12)	B8—B12	1.7809 (12)
B2—B6	1.7702 (12)	B8—B9	1.7898 (12)
N1—H1A	0.898 (12)	B8—H8	1.088 (11)
N1—H1B	0.900 (12)	B9—B12	1.7822 (12)
N1—H1C	0.857 (12)	B9—B10	1.7878 (12)
B3—B8	1.7641 (12)	B9—H9	1.099 (10)
B3—B4	1.7742 (12)	B10—B11	1.7856 (12)
B3—B7	1.7777 (12)	B10—B12	1.7937 (12)
B3—H3	1.075 (10)	B10—H10	1.091 (10)
B4—B9	1.7692 (12)	B11—B12	1.7811 (12)
B4—B8	1.7816 (12)	B11—H11	1.091 (10)
B4—B5	1.7885 (13)	B12—H12	1.110 (10)
B4—H4	1.083 (11)	O1—C2	1.4532 (10)
B5—B10	1.7761 (12)	O1—H1O	0.768 (15)
B5—B9	1.7770 (12)	C2—C3	1.4958 (12)
B2—C1—B5	114.11 (6)	B11—B6—H6	125.5 (6)
B2—C1—B4	113.81 (6)	B5—B6—H6	121.8 (5)
B5—C1—B4	63.16 (5)	B2—B7—B3	59.94 (5)
B2—C1—B6	62.60 (5)	B2—B7—B12	106.02 (6)
B5—C1—B6	62.71 (5)	B3—B7—B12	106.91 (6)
B4—C1—B6	115.05 (6)	B2—B7—B8	106.64 (6)
B2—C1—B3	62.53 (5)	B3—B7—B8	59.27 (5)
B5—C1—B3	114.82 (6)	B12—B7—B8	59.88 (5)
B4—C1—B3	62.29 (5)	B2—B7—B11	59.17 (4)
B6—C1—B3	114.99 (6)	B3—B7—B11	107.76 (6)
B2—C1—H1	117.9 (6)	B12—B7—B11	59.72 (5)
B5—C1—H1	118.2 (6)	B8—B7—B11	107.85 (6)
B4—C1—H1	118.1 (6)	B2—B7—H7	120.6 (6)
B6—C1—H1	117.5 (6)	B3—B7—H7	121.1 (5)
B3—C1—H1	117.3 (6)	B12—B7—H7	124.6 (5)
N1—B2—C1	118.49 (6)	B8—B7—H7	123.9 (6)
N1—B2—B11	125.67 (6)	B11—B7—H7	121.2 (6)
C1—B2—B11	106.60 (6)	B3—B8—B12	107.41 (6)
N1—B2—B7	124.58 (6)	B3—B8—B4	60.05 (5)
C1—B2—B7	106.76 (6)	B12—B8—B4	107.30 (6)
B11—B2—B7	61.41 (5)	B3—B8—B9	107.38 (6)
N1—B2—B3	118.02 (6)	B12—B8—B9	59.88 (5)
C1—B2—B3	59.66 (5)	B4—B8—B9	59.39 (5)
B11—B2—B3	109.94 (6)	B3—B8—B7	60.03 (5)
B7—B2—B3	60.43 (5)	B12—B8—B7	59.76 (5)
N1—B2—B6	119.03 (6)	B4—B8—B7	108.02 (6)
C1—B2—B6	59.59 (5)	B9—B8—B7	107.76 (6)
B11—B2—B6	60.70 (5)	B3—B8—H8	120.9 (5)
B7—B2—B6	110.51 (6)	B12—B8—H8	123.2 (5)
B3—B2—B6	110.12 (6)	B4—B8—H8	121.2 (6)
B2—N1—H1A	112.1 (7)	B9—B8—H8	122.7 (6)
B2—N1—H1B	113.1 (7)	B7—B8—H8	121.8 (6)
H1A—N1—H1B	107.4 (10)	B4—B9—B5	60.58 (5)
B2—N1—H1C	111.7 (8)	B4—B9—B12	107.78 (6)
H1A—N1—H1C	105.5 (10)	B5—B9—B12	108.06 (6)
H1B—N1—H1C	106.6 (10)	B4—B9—B10	108.28 (6)
C1—B3—B8	104.97 (6)	B5—B9—B10	59.77 (5)
C1—B3—B2	57.81 (5)	B12—B9—B10	60.32 (5)
B8—B3—B2	107.51 (6)	B4—B9—B8	60.07 (5)
C1—B3—B4	58.54 (5)	B5—B9—B8	108.71 (6)
B8—B3—B4	60.47 (5)	B12—B9—B8	59.81 (5)
B2—B3—B4	106.86 (6)	B10—B9—B8	108.47 (6)
C1—B3—B7	104.68 (6)	B4—B9—H9	121.0 (5)
B8—B3—B7	60.70 (5)	B5—B9—H9	121.0 (6)
B2—B3—B7	59.63 (5)	B12—B9—H9	122.5 (5)
B4—B3—B7	108.88 (6)	B10—B9—H9	121.8 (5)
C1—B3—H3	118.3 (6)	B8—B9—H9	121.4 (6)
B8—B3—H3	128.6 (6)	B6—B10—B5	60.46 (5)
B2—B3—H3	118.2 (6)	B6—B10—B11	60.32 (5)
B4—B3—H3	121.0 (5)	B5—B10—B11	108.48 (6)
B7—B3—H3	125.7 (5)	B6—B10—B9	108.17 (6)
C1—B4—B9	104.15 (6)	B5—B10—B9	59.81 (5)
C1—B4—B3	59.17 (5)	B11—B10—B9	107.78 (6)
B9—B4—B3	107.84 (6)	B6—B10—B12	107.86 (6)
C1—B4—B8	104.69 (6)	B5—B10—B12	107.59 (6)
B9—B4—B8	60.54 (5)	B11—B10—B12	59.68 (5)
B3—B4—B8	59.49 (5)	B9—B10—B12	59.69 (5)
C1—B4—B5	58.31 (5)	B6—B10—H10	121.1 (6)
B9—B4—B5	59.93 (5)	B5—B10—H10	121.5 (5)
B3—B4—B5	108.24 (6)	B11—B10—H10	121.5 (5)
B8—B4—B5	108.57 (6)	B9—B10—H10	122.2 (6)
C1—B4—H4	119.8 (6)	B12—B10—H10	122.4 (6)
B9—B4—H4	126.9 (6)	B2—B11—B12	106.11 (6)
B3—B4—H4	119.3 (6)	B2—B11—B6	59.96 (5)
B8—B4—H4	125.9 (6)	B12—B11—B6	107.55 (6)
B5—B4—H4	120.0 (6)	B2—B11—B10	106.46 (6)
C1—B5—B10	104.26 (6)	B12—B11—B10	60.38 (5)
C1—B5—B9	103.98 (6)	B6—B11—B10	59.23 (5)
B10—B5—B9	60.42 (5)	B2—B11—B7	59.42 (5)
C1—B5—B6	59.03 (5)	B12—B11—B7	59.59 (4)
B10—B5—B6	59.42 (5)	B6—B11—B7	108.32 (6)
B9—B5—B6	107.84 (6)	B10—B11—B7	108.14 (6)
C1—B5—B4	58.52 (5)	B2—B11—H11	121.8 (6)
B10—B5—B4	107.94 (6)	B12—B11—H11	123.8 (6)
B9—B5—B4	59.50 (5)	B6—B11—H11	120.5 (6)
B6—B5—B4	108.23 (6)	B10—B11—H11	122.5 (6)
C1—B5—H5	119.9 (6)	B7—B11—H11	122.0 (6)
B10—B5—H5	126.7 (6)	B7—B12—B8	60.37 (5)
B9—B5—H5	126.7 (6)	B7—B12—B11	60.69 (5)
B6—B5—H5	119.7 (6)	B8—B12—B11	109.01 (6)
B4—B5—H5	119.7 (6)	B7—B12—B9	108.58 (6)
C1—B6—B10	104.21 (6)	B8—B12—B9	60.31 (5)
C1—B6—B2	57.80 (4)	B11—B12—B9	108.23 (6)
B10—B6—B2	106.93 (6)	B7—B12—B10	108.66 (6)
C1—B6—B11	104.15 (6)	B8—B12—B10	108.60 (6)
B10—B6—B11	60.45 (5)	B11—B12—B10	59.93 (5)
B2—B6—B11	59.34 (5)	B9—B12—B10	59.99 (5)
C1—B6—B5	58.26 (5)	B7—B12—H12	121.5 (5)
B10—B6—B5	60.12 (5)	B8—B12—H12	121.3 (5)
B2—B6—B5	106.55 (6)	B11—B12—H12	121.4 (5)
B11—B6—B5	108.32 (6)	B9—B12—H12	121.4 (5)
C1—B6—H6	118.9 (5)	B10—B12—H12	121.3 (5)
B10—B6—H6	129.1 (5)	C2—O1—H1O	109.4 (11)
B2—B6—H6	118.1 (5)	O1—C2—C3	108.36 (7)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1B···O1	0.900 (12)	2.006 (12)	2.8937 (9)	168.5 (10)
N1—H1A···O1i	0.898 (12)	2.065 (12)	2.9446 (9)	166.1 (10)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1B⋯O1	0.900 (12)	2.006 (12)	2.8937 (9)	168.5 (10)
N1—H1A⋯O1i	0.898 (12)	2.065 (12)	2.9446 (9)	166.1 (10)

Symmetry code: (i) .