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The title compound, C3H12B10O2 or 1-COOH-1,2-closo-C2B10H11, forms centrosymmetric dimers through intermolecular hydrogen bonding between the carboxylic acid groups, resulting in the formation of an eight-membered ring [R{_2^2}(8)]. The C=O bond of the carboxylic acid group almost eclipses the unsubstituted cage C atom, with a C-C-C-O torsion angle of 2.6 (2)°.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101010204/gd1160sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270101010204/gd1160Isup2.hkl
Contains datablock I

CCDC reference: 175078

Comment top

The usefulness of heteroboranes in studies of crystal engineering has only recently begun to be exploited (Centore et al., 1994; Davidson et al., 1996; Hosmane et al., 1998; Lee et al., 2000), yet such compounds have a number of potential advantages in this respect. Heteroboranes are generally thermally and chemically stable compounds. They exist as polyhedra or fragments of polyhedra of differing size and shape, but have architectures that are well understood (Wade, 1976). Isomeric possibilities mean that C-substituted (hetero)carboranes have the potential to function as supramolecular building blocks with differing directionalities. Significant variation is also possible in the number and nature of the substituents that can be attached to the B atoms of heteroboranes, affording these species the potential to act as supramolecular building blocks in three dimensions. Finally, heteroboranes are usually neutral or anionic, but can also be cationic (see e.g. Douek & Welch, 1993).

Within the field of crystal engineering, the carboxylic acid group is frequently used to afford supramolecular assemblies through intermolecular H···O bonding (Leiserowitz, 1976). Accordingly, we have begun a systematic study of the crystal chemistry of carboxylic acid carboranes and their derivatives. Herein, we describe the structure of the simplest carboxylic acid carborane, 1,2-dicarba-closo-dodecaborane(12)–1-carboxylic acid, (I). \sch

Compound (I) crystallizes as a dimer, linked by two O—H···O hydrogen bonds about a centre of inversion (Fig. 1), typical of the packing of carboxylic acid units (Leiserowitz, 1976). In graph-set terminology (Etter, 1990; Etter & MacDonald, 1990), this motif is denoted R22(8). The only other carboxylic acid carborane to be structurally characterized so far is 1,12-closo-C2B10H10-1,12-(COOH)2, (II) (Centore et al., 1994). In (II), the molecules pack as linear hydrogen-bonded chains. The dimensions of the hydrogen bond in (I) (Table 2) identify it as `strong' (Desiraju & Steiner, 1999) and bear good comparison with the corresponding O···O distance in (II) (2.639 Å).

In carboxylic acid derivatives of 1,2-dicarbaborane, we may define the orientation of the carboxylic acid group by θ, the C2—C1—C3—O2 dihedral angle. In compound (I), θ = 2.6 (2)°. This is complemented by a C1—C2 connectivity of length 1.632 (2) Å, in excellent agreement with that in the parent compound 1,2-closo-C2B10H12 [1.630 (6) Å; Davidson et al., 1996], and by a C1—C3 bond of 1.507 (2) Å.

The C—B distances span the range 1.690 (2)–1.729 (2) Å and the B—B distances 1.759 (2)–1.795 (3) Å. There is no evidence for disorder of the C2 vertex, identified on the twin bases of refined (as B) isotropic displacement parameters and intra-cage distances.

Related literature top

For related literature, see: Centore et al. (1994); Davidson et al. (1996); Desiraju & Steiner (1999); Douek & Welch (1993); Etter (1990); Etter & MacDonald (1990); Hosmane et al. (1998); Lee et al. (2000); Leiserowitz (1976); Wade (1976); Zakharkin & Grebennikov (1967).

Experimental top

Compound (I) was prepared based on the literature method of Zakharkin & Grebennikov (1967) in 73% yield and crystals were grown by evaporation of an acetonitrile solution. Analysis: calculated for C3H12B10O2: C 19.1, H 6.4%; found: C 18.3, H 6.90%; 1H FT-NMR (400.1 MHz, TMS, δ, p.p.m.): 10.40 (1H, br, O—H), 4.00 (1H, s, C—H); 11B-{1H} FT-NMR (128.4 MHz, BF3·OEt2, δ, p.p.m.): 0.77 (2B), -5.97 (2B), -8.79 (2B), -10.52(2B), -11.65(2B). NMR spectra were recorded from solution in CDCl3 at 293 K on a Bruker DPX400 spectrometer.

Refinement top

All H atoms (both cage H atoms and COOH) were located from the difference Fourier map and refined, but cage H atoms were restrained, with B—H = 1.10 (2) Å.

Computing details top

Data collection: XSCANS (Bruker, 1996); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

Figures top
[Figure 1] Fig. 1. A perspective view of the dimer of (I) with displacement ellipsoids shown at the 50% probability level. H atoms are drawn as small spheres of arbitrary radii and hydrogen bonds are shown as dotted lines.
1,2-Dicarba-closo-dodecaborane(12)–1-carboxylic acid top
Crystal data top
C3H12B10O2F(000) = 384
Mr = 188.23Dx = 1.188 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 6.988 (2) ÅCell parameters from 46 reflections
b = 12.031 (3) Åθ = 3.2–12.5°
c = 12.869 (4) ŵ = 0.07 mm1
β = 103.33 (2)°T = 160 K
V = 1052.8 (5) Å3Needle, colourless
Z = 40.82 × 0.24 × 0.20 mm
Data collection top
Bruker P4
diffractometer
Rint = 0.041
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.4°
Graphite monochromatorh = 18
ω scansk = 141
2577 measured reflectionsl = 1515
1849 independent reflections3 standard reflections every 97 reflections
1557 reflections with I > 2σ(I) intensity decay: none
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02 w = 1/[σ2(Fo2) + (0.0612P)2 + 0.3182P]
where P = (Fo2 + 2Fc2)/3
1849 reflections(Δ/σ)max = 0.013
184 parametersΔρmax = 0.21 e Å3
10 restraintsΔρmin = 0.23 e Å3
Crystal data top
C3H12B10O2V = 1052.8 (5) Å3
Mr = 188.23Z = 4
Monoclinic, P21/cMo Kα radiation
a = 6.988 (2) ŵ = 0.07 mm1
b = 12.031 (3) ÅT = 160 K
c = 12.869 (4) Å0.82 × 0.24 × 0.20 mm
β = 103.33 (2)°
Data collection top
Bruker P4
diffractometer
Rint = 0.041
2577 measured reflections3 standard reflections every 97 reflections
1849 independent reflections intensity decay: none
1557 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.04310 restraints
wR(F2) = 0.119H atoms treated by a mixture of independent and constrained refinement
S = 1.02Δρmax = 0.21 e Å3
1849 reflectionsΔρmin = 0.23 e Å3
184 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
C10.2990 (2)0.09740 (12)0.19910 (11)0.0205 (3)
C20.1608 (2)0.00725 (13)0.24206 (13)0.0258 (4)
H20.156 (3)0.0617 (16)0.2103 (15)0.030 (5)*
B30.3853 (3)0.04007 (16)0.32434 (14)0.0281 (4)
H30.503 (2)0.0211 (14)0.3317 (15)0.036 (5)*
B40.4129 (3)0.18515 (15)0.29881 (14)0.0252 (4)
H40.561 (2)0.2158 (15)0.2983 (15)0.035 (5)*
B50.2059 (3)0.22885 (14)0.19796 (13)0.0224 (4)
H50.227 (3)0.2857 (14)0.1351 (13)0.032 (5)*
B60.0466 (3)0.11200 (15)0.15923 (14)0.0243 (4)
H60.021 (3)0.0895 (15)0.0762 (11)0.031 (5)*
B70.1689 (3)0.02422 (16)0.37368 (16)0.0328 (5)
H70.151 (3)0.0493 (14)0.4200 (15)0.046 (6)*
B80.3270 (3)0.14071 (17)0.41208 (14)0.0293 (4)
H80.419 (3)0.1497 (16)0.4917 (12)0.037 (5)*
B90.2149 (3)0.25692 (15)0.33484 (14)0.0247 (4)
H90.234 (3)0.3438 (12)0.3654 (14)0.033 (5)*
B100.0095 (3)0.21156 (15)0.24783 (14)0.0253 (4)
H100.135 (2)0.2662 (14)0.2222 (14)0.038 (5)*
B110.0369 (3)0.06777 (16)0.27325 (16)0.0298 (4)
H110.172 (3)0.0199 (16)0.2630 (18)0.050 (6)*
B120.0656 (3)0.15804 (16)0.38111 (15)0.0291 (4)
H120.016 (2)0.1772 (15)0.4428 (13)0.031 (5)*
O10.50751 (17)0.12697 (9)0.08288 (9)0.0296 (3)
O20.35818 (18)0.03929 (9)0.07678 (9)0.0316 (3)
C30.3924 (2)0.05412 (13)0.11255 (11)0.0222 (3)
H10.552 (4)0.094 (2)0.026 (2)0.072 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0248 (8)0.0207 (7)0.0175 (7)0.0011 (6)0.0078 (6)0.0017 (6)
C20.0351 (9)0.0188 (8)0.0280 (8)0.0008 (7)0.0167 (7)0.0015 (6)
B30.0360 (10)0.0300 (10)0.0197 (8)0.0100 (8)0.0095 (7)0.0052 (7)
B40.0270 (9)0.0294 (9)0.0190 (8)0.0002 (7)0.0048 (7)0.0025 (7)
B50.0278 (9)0.0193 (8)0.0214 (8)0.0013 (7)0.0083 (7)0.0001 (7)
B60.0229 (9)0.0247 (9)0.0254 (9)0.0011 (7)0.0059 (7)0.0027 (7)
B70.0505 (12)0.0262 (9)0.0286 (10)0.0053 (9)0.0235 (9)0.0058 (7)
B80.0370 (11)0.0342 (10)0.0179 (8)0.0066 (8)0.0086 (8)0.0014 (7)
B90.0307 (10)0.0233 (9)0.0215 (8)0.0004 (7)0.0092 (7)0.0023 (7)
B100.0267 (9)0.0220 (8)0.0290 (9)0.0015 (7)0.0098 (7)0.0029 (7)
B110.0332 (10)0.0244 (9)0.0375 (10)0.0043 (8)0.0198 (8)0.0054 (8)
B120.0375 (10)0.0283 (9)0.0267 (9)0.0017 (8)0.0180 (8)0.0012 (7)
O10.0377 (7)0.0303 (6)0.0260 (6)0.0037 (5)0.0178 (5)0.0032 (5)
O20.0412 (7)0.0282 (6)0.0313 (6)0.0028 (5)0.0205 (5)0.0067 (5)
C30.0249 (8)0.0251 (8)0.0175 (7)0.0035 (6)0.0065 (6)0.0016 (6)
Geometric parameters (Å, º) top
C1—C21.631 (2)B6—B101.759 (2)
C1—C31.507 (2)B6—B111.781 (3)
C1—B31.729 (2)B6—H61.099 (14)
C1—B41.710 (2)B7—B81.782 (3)
C1—B51.709 (2)B7—B111.777 (3)
C1—B61.728 (2)B7—B121.776 (3)
C2—B31.724 (3)B7—H71.091 (15)
C2—B61.723 (2)B8—B91.788 (3)
C2—B71.694 (2)B8—B121.790 (3)
C2—B111.690 (2)B8—H81.083 (14)
C2—H20.922 (19)B9—B101.789 (3)
B3—B41.795 (3)B9—B121.774 (3)
B3—B71.780 (3)B9—H91.114 (14)
B3—B81.766 (3)B10—B111.779 (3)
B3—H31.093 (14)B10—B121.794 (3)
B4—B51.785 (2)B10—H101.087 (14)
B4—B81.782 (2)B11—B121.778 (3)
B4—B91.780 (3)B11—H111.090 (15)
B4—H41.102 (14)B12—H121.103 (14)
B5—B61.791 (2)O1—C31.3051 (19)
B5—B91.780 (2)O1—H10.95 (3)
B5—B101.779 (3)O2—C31.2170 (19)
B5—H51.097 (14)
C3—C1—C2114.31 (12)B12—B7—B1160.06 (11)
C3—C1—B5122.84 (12)C2—B7—B359.43 (10)
C2—C1—B5111.34 (12)B12—B7—B3108.15 (13)
C3—C1—B4124.21 (13)B11—B7—B3108.71 (13)
C2—C1—B4111.44 (11)C2—B7—B8104.34 (12)
B5—C1—B462.96 (10)B12—B7—B860.40 (11)
C3—C1—B6113.67 (12)B11—B7—B8108.42 (13)
C2—C1—B661.63 (10)B3—B7—B859.44 (11)
B5—C1—B662.78 (10)C2—B7—H7117.9 (11)
B4—C1—B6115.23 (12)B12—B7—H7127.4 (11)
C3—C1—B3115.72 (12)B11—B7—H7117.5 (11)
C2—C1—B361.64 (10)B3—B7—H7119.7 (11)
B5—C1—B3115.30 (11)B8—B7—H7128.9 (11)
B4—C1—B362.93 (10)B3—B8—B460.78 (10)
B6—C1—B3115.45 (12)B3—B8—B760.21 (11)
C1—C2—B11111.99 (12)B4—B8—B7108.26 (12)
C1—C2—B7111.89 (13)B3—B8—B9108.46 (12)
B11—C2—B763.33 (11)B4—B8—B959.83 (10)
C1—C2—B661.96 (10)B7—B8—B9107.26 (13)
B11—C2—B662.90 (11)B3—B8—B12108.15 (14)
B7—C2—B6115.74 (13)B4—B8—B12107.58 (12)
C1—C2—B361.96 (10)B7—B8—B1259.63 (11)
B11—C2—B3115.69 (13)B9—B8—B1259.44 (10)
B7—C2—B362.76 (11)B3—B8—H8119.9 (10)
B6—C2—B3116.01 (12)B4—B8—H8120.3 (10)
C1—C2—H2114.3 (12)B7—B8—H8122.4 (10)
B11—C2—H2123.0 (12)B9—B8—H8122.5 (10)
B7—C2—H2122.8 (12)B12—B8—H8123.6 (10)
B6—C2—H2114.8 (12)B12—B9—B5108.39 (12)
B3—C2—H2114.4 (12)B12—B9—B4108.35 (13)
C2—B3—C156.39 (9)B5—B9—B460.19 (10)
C2—B3—B8103.80 (13)B12—B9—B860.33 (11)
C1—B3—B8103.91 (12)B5—B9—B8108.23 (12)
C2—B3—B757.81 (11)B4—B9—B859.91 (10)
C1—B3—B7103.49 (13)B12—B9—B1060.45 (11)
B8—B3—B760.35 (11)B5—B9—B1059.79 (10)
C2—B3—B4103.38 (12)B4—B9—B10108.10 (12)
C1—B3—B458.02 (9)B8—B9—B10108.52 (13)
B8—B3—B460.04 (10)B12—B9—H9122.9 (9)
B7—B3—B4107.79 (13)B5—B9—H9120.1 (9)
C2—B3—H3117.4 (10)B4—B9—H9120.6 (10)
C1—B3—H3116.2 (10)B8—B9—H9122.4 (9)
B8—B3—H3133.5 (10)B10—B9—H9121.6 (10)
B7—B3—H3125.7 (10)B6—B10—B560.80 (10)
B4—B3—H3124.0 (10)B6—B10—B1160.44 (10)
C1—B4—B9103.88 (12)B5—B10—B11108.41 (12)
C1—B4—B8104.03 (13)B6—B10—B9108.60 (13)
B9—B4—B860.26 (10)B5—B10—B959.86 (10)
C1—B4—B558.50 (9)B11—B10—B9107.31 (13)
B9—B4—B559.90 (10)B6—B10—B12108.39 (13)
B8—B4—B5108.28 (13)B5—B10—B12107.56 (13)
C1—B4—B359.05 (9)B11—B10—B1259.68 (10)
B9—B4—B3107.53 (13)B9—B10—B1259.34 (10)
B8—B4—B359.18 (10)B6—B10—H10120.1 (10)
B5—B4—B3108.43 (13)B5—B10—H10120.9 (10)
C1—B4—H4118.5 (10)B11—B10—H10122.0 (10)
B9—B4—H4128.9 (10)B9—B10—H10122.5 (10)
B8—B4—H4126.9 (10)B12—B10—H10123.0 (10)
B5—B4—H4120.2 (10)C2—B11—B758.44 (10)
B3—B4—H4117.9 (10)C2—B11—B12104.13 (14)
C1—B5—B10103.95 (12)B7—B11—B1259.95 (11)
C1—B5—B9103.91 (11)C2—B11—B10104.28 (13)
B10—B5—B960.36 (10)B7—B11—B10108.48 (14)
C1—B5—B458.54 (9)B12—B11—B1060.56 (10)
B10—B5—B4108.32 (12)C2—B11—B659.45 (10)
B9—B5—B459.90 (10)B7—B11—B6108.85 (13)
C1—B5—B659.14 (9)B12—B11—B6108.12 (13)
B10—B5—B659.05 (10)B10—B11—B659.23 (10)
B9—B5—B6107.61 (12)C2—B11—H11118.5 (11)
B4—B5—B6108.57 (12)B7—B11—H11117.8 (12)
C1—B5—H5117.8 (10)B12—B11—H11126.9 (12)
B10—B5—H5127.7 (9)B10—B11—H11128.3 (11)
B9—B5—H5129.3 (9)B6—B11—H11119.9 (12)
B4—B5—H5119.6 (9)B9—B12—B7108.17 (13)
B6—B5—H5117.8 (9)B9—B12—B11108.06 (12)
C2—B6—C156.41 (9)B7—B12—B1159.99 (11)
C2—B6—B10103.75 (12)B9—B12—B860.23 (11)
C1—B6—B10103.98 (12)B7—B12—B859.98 (11)
C2—B6—B1157.65 (10)B11—B12—B8108.03 (13)
C1—B6—B11103.36 (12)B9—B12—B1060.21 (10)
B10—B6—B1160.33 (10)B7—B12—B10107.87 (12)
C2—B6—B5103.45 (12)B11—B12—B1059.76 (10)
C1—B6—B558.08 (9)B8—B12—B10108.25 (13)
B10—B6—B560.14 (10)B9—B12—H12122.9 (9)
B11—B6—B5107.82 (12)B7—B12—H12120.7 (9)
C2—B6—H6117.1 (10)B11—B12—H12120.5 (9)
C1—B6—H6116.4 (9)B8—B12—H12122.2 (9)
B10—B6—H6133.5 (9)B10—B12—H12121.9 (9)
B11—B6—H6125.4 (9)C3—O1—H1106.0 (16)
B5—B6—H6124.4 (9)O2—C3—O1126.15 (14)
C2—B7—B12104.06 (13)O2—C3—C1121.19 (14)
C2—B7—B1158.23 (11)O1—C3—C1112.66 (13)
C3—C1—C2—B11144.37 (13)B11—B7—B8—B90.49 (16)
B5—C1—C2—B110.24 (17)B3—B7—B8—B9101.79 (13)
B4—C1—C2—B1168.47 (16)C2—B7—B8—B1298.23 (14)
B6—C1—C2—B1139.49 (12)B11—B7—B8—B1237.42 (12)
B3—C1—C2—B11108.33 (14)B3—B7—B8—B12138.72 (13)
C3—C1—C2—B7146.69 (13)C1—B5—B9—B1260.98 (15)
B5—C1—C2—B768.70 (16)B10—B5—B9—B1237.35 (12)
B4—C1—C2—B70.47 (17)B4—B5—B9—B12101.06 (14)
B6—C1—C2—B7108.43 (14)B6—B5—B9—B120.61 (17)
B3—C1—C2—B739.39 (13)C1—B5—B9—B440.08 (11)
C3—C1—C2—B6104.88 (13)B10—B5—B9—B4138.41 (13)
B5—C1—C2—B639.73 (12)B6—B5—B9—B4101.67 (13)
B4—C1—C2—B6107.97 (13)C1—B5—B9—B82.93 (16)
B3—C1—C2—B6147.82 (12)B10—B5—B9—B8101.26 (14)
C3—C1—C2—B3107.30 (14)B4—B5—B9—B837.15 (12)
B5—C1—C2—B3108.09 (13)B6—B5—B9—B864.52 (15)
B4—C1—C2—B339.86 (12)C1—B5—B9—B1098.33 (12)
B6—C1—C2—B3147.82 (12)B4—B5—B9—B10138.41 (13)
B11—C2—B3—C1102.40 (14)B6—B5—B9—B1036.74 (11)
B7—C2—B3—C1138.53 (13)C1—B4—B9—B1261.07 (15)
B6—C2—B3—C131.53 (12)B8—B4—B9—B1237.35 (12)
C1—C2—B3—B897.70 (13)B5—B4—B9—B12101.13 (14)
B11—C2—B3—B84.70 (17)B3—B4—B9—B120.41 (16)
B7—C2—B3—B840.83 (12)C1—B4—B9—B540.06 (11)
B6—C2—B3—B866.16 (16)B8—B4—B9—B5138.48 (13)
C1—C2—B3—B7138.53 (13)B3—B4—B9—B5101.54 (13)
B11—C2—B3—B736.13 (13)C1—B4—B9—B898.42 (13)
B6—C2—B3—B7106.99 (14)B5—B4—B9—B8138.48 (13)
C1—C2—B3—B435.74 (11)B3—B4—B9—B836.94 (12)
B11—C2—B3—B466.66 (16)C1—B4—B9—B102.94 (15)
B7—C2—B3—B4102.79 (13)B8—B4—B9—B10101.36 (14)
B6—C2—B3—B44.21 (17)B5—B4—B9—B1037.12 (12)
C3—C1—B3—C2105.02 (14)B3—B4—B9—B1064.42 (15)
B5—C1—B3—C2101.67 (14)B3—B8—B9—B12100.61 (15)
B4—C1—B3—C2137.94 (13)B4—B8—B9—B12138.49 (13)
B6—C1—B3—C231.26 (12)B7—B8—B9—B1237.02 (12)
C3—C1—B3—B8157.48 (13)B3—B8—B9—B50.60 (17)
C2—C1—B3—B897.50 (14)B4—B8—B9—B537.27 (12)
B5—C1—B3—B84.17 (17)B7—B8—B9—B564.20 (15)
B4—C1—B3—B840.44 (12)B12—B8—B9—B5101.22 (14)
B6—C1—B3—B866.24 (16)B3—B8—B9—B437.88 (13)
C3—C1—B3—B7140.22 (13)B7—B8—B9—B4101.47 (13)
C2—C1—B3—B735.19 (12)B12—B8—B9—B4138.49 (13)
B5—C1—B3—B766.47 (16)B3—B8—B9—B1062.75 (16)
B4—C1—B3—B7102.74 (13)B4—B8—B9—B10100.63 (13)
B6—C1—B3—B73.93 (17)B7—B8—B9—B100.84 (16)
C3—C1—B3—B4117.04 (14)B12—B8—B9—B1037.86 (12)
C2—C1—B3—B4137.94 (13)C2—B6—B10—B597.80 (13)
B5—C1—B3—B436.27 (13)C1—B6—B10—B539.54 (11)
B6—C1—B3—B4106.68 (14)B11—B6—B10—B5137.13 (13)
C3—C1—B4—B9153.68 (13)C2—B6—B10—B1139.34 (12)
C2—C1—B4—B963.03 (15)C1—B6—B10—B1197.60 (13)
B5—C1—B4—B940.77 (11)B5—B6—B10—B11137.13 (13)
B6—C1—B4—B94.68 (16)C2—B6—B10—B960.45 (15)
B3—C1—B4—B9102.33 (13)C1—B6—B10—B92.19 (15)
C3—C1—B4—B8144.03 (14)B11—B6—B10—B999.79 (14)
C2—C1—B4—B80.74 (15)B5—B6—B10—B937.34 (12)
B5—C1—B4—B8103.06 (13)C2—B6—B10—B122.48 (16)
B6—C1—B4—B866.98 (15)C1—B6—B10—B1260.74 (15)
B3—C1—B4—B840.04 (11)B11—B6—B10—B1236.86 (13)
C3—C1—B4—B5112.91 (15)B5—B6—B10—B12100.28 (14)
C2—C1—B4—B5103.80 (13)C1—B5—B10—B640.07 (11)
B6—C1—B4—B536.09 (12)B9—B5—B10—B6138.33 (13)
B3—C1—B4—B5143.10 (13)B4—B5—B10—B6101.10 (13)
C3—C1—B4—B3104.00 (15)C1—B5—B10—B111.48 (16)
C2—C1—B4—B339.30 (12)B9—B5—B10—B1199.75 (14)
B5—C1—B4—B3143.10 (13)B4—B5—B10—B1162.52 (16)
B6—C1—B4—B3107.01 (13)B6—B5—B10—B1138.59 (12)
C2—B3—B4—C135.00 (10)C1—B5—B10—B998.26 (12)
B8—B3—B4—C1133.39 (13)B4—B5—B10—B937.23 (12)
B7—B3—B4—C195.07 (14)B6—B5—B10—B9138.33 (13)
C2—B3—B4—B960.98 (14)C1—B5—B10—B1261.60 (14)
C1—B3—B4—B995.97 (13)B9—B5—B10—B1236.66 (11)
B8—B3—B4—B937.41 (12)B4—B5—B10—B120.57 (16)
B7—B3—B4—B90.90 (16)B6—B5—B10—B12101.67 (13)
C2—B3—B4—B898.39 (13)B12—B9—B10—B6100.81 (13)
C1—B3—B4—B8133.39 (13)B5—B9—B10—B637.76 (12)
B7—B3—B4—B838.31 (12)B4—B9—B10—B60.46 (17)
C2—B3—B4—B52.34 (15)B8—B9—B10—B663.00 (15)
C1—B3—B4—B532.66 (11)B12—B9—B10—B5138.57 (13)
B8—B3—B4—B5100.73 (14)B4—B9—B10—B537.30 (12)
B7—B3—B4—B562.42 (15)B8—B9—B10—B5100.76 (13)
C3—C1—B5—B10141.88 (14)B12—B9—B10—B1136.93 (12)
C2—C1—B5—B100.79 (15)B5—B9—B10—B11101.63 (13)
B4—C1—B5—B10103.17 (13)B4—B9—B10—B1164.34 (15)
B6—C1—B5—B1040.03 (11)B8—B9—B10—B110.87 (16)
B3—C1—B5—B1066.91 (15)B5—B9—B10—B12138.57 (13)
C3—C1—B5—B9155.73 (13)B4—B9—B10—B12101.27 (14)
C2—C1—B5—B963.18 (15)B8—B9—B10—B1237.81 (12)
B4—C1—B5—B940.78 (11)C1—C2—B11—B7104.31 (14)
B6—C1—B5—B9102.41 (13)B6—C2—B11—B7143.40 (13)
B3—C1—B5—B94.52 (17)B3—C2—B11—B735.92 (13)
C3—C1—B5—B4114.96 (16)C1—C2—B11—B1263.84 (15)
C2—C1—B5—B4103.96 (13)B7—C2—B11—B1240.47 (12)
B6—C1—B5—B4143.19 (12)B6—C2—B11—B12102.94 (13)
B3—C1—B5—B436.25 (13)B3—C2—B11—B124.55 (17)
C3—C1—B5—B6101.85 (15)C1—C2—B11—B101.16 (17)
C2—C1—B5—B639.23 (12)B7—C2—B11—B10103.15 (14)
B4—C1—B5—B6143.19 (12)B6—C2—B11—B1040.25 (12)
B3—C1—B5—B6106.94 (14)B3—C2—B11—B1067.23 (16)
B9—B4—B5—C1132.88 (12)C1—C2—B11—B639.09 (12)
B8—B4—B5—C195.57 (13)B7—C2—B11—B6143.40 (13)
B3—B4—B5—C132.87 (11)B3—C2—B11—B6107.49 (14)
C1—B4—B5—B1095.46 (12)B12—B7—B11—C2133.35 (13)
B9—B4—B5—B1037.43 (12)B3—B7—B11—C232.72 (12)
B8—B4—B5—B100.11 (16)B8—B7—B11—C295.78 (14)
B3—B4—B5—B1062.58 (15)C2—B7—B11—B12133.35 (13)
C1—B4—B5—B9132.88 (12)B3—B7—B11—B12100.64 (14)
B8—B4—B5—B937.31 (12)B8—B7—B11—B1237.57 (12)
B3—B4—B5—B9100.01 (13)C2—B7—B11—B1095.73 (13)
C1—B4—B5—B632.86 (11)B12—B7—B11—B1037.62 (12)
B9—B4—B5—B6100.03 (13)B3—B7—B11—B1063.01 (16)
B8—B4—B5—B662.71 (15)B8—B7—B11—B100.05 (17)
B3—B4—B5—B60.02 (16)C2—B7—B11—B632.86 (12)
B11—C2—B6—C1138.52 (12)B12—B7—B11—B6100.50 (13)
B7—C2—B6—C1102.26 (15)B3—B7—B11—B60.14 (17)
B3—C2—B6—C131.53 (12)B8—B7—B11—B662.93 (16)
C1—C2—B6—B1097.82 (12)B6—B10—B11—C240.37 (12)
B11—C2—B6—B1040.69 (12)B5—B10—B11—C21.62 (17)
B7—C2—B6—B104.43 (18)B9—B10—B11—C261.60 (15)
B3—C2—B6—B1066.29 (16)B12—B10—B11—C298.38 (14)
C1—C2—B6—B11138.52 (12)B6—B10—B11—B7101.40 (14)
B7—C2—B6—B1136.26 (14)B5—B10—B11—B762.65 (16)
B3—C2—B6—B11106.98 (15)B9—B10—B11—B70.57 (16)
C1—C2—B6—B535.75 (10)B12—B10—B11—B737.35 (12)
B11—C2—B6—B5102.76 (13)B6—B10—B11—B12138.75 (13)
B7—C2—B6—B566.50 (16)B5—B10—B11—B12100.00 (14)
B3—C2—B6—B54.22 (17)B9—B10—B11—B1236.78 (12)
C3—C1—B6—C2105.91 (14)B5—B10—B11—B638.75 (12)
B5—C1—B6—C2137.97 (12)B9—B10—B11—B6101.97 (14)
B4—C1—B6—C2101.82 (13)B12—B10—B11—B6138.75 (13)
B3—C1—B6—C231.26 (12)C1—B6—B11—C234.55 (11)
C3—C1—B6—B10156.70 (12)B10—B6—B11—C2133.21 (14)
C2—C1—B6—B1097.39 (13)B5—B6—B11—C294.91 (13)
B5—C1—B6—B1040.58 (11)C2—B6—B11—B732.47 (12)
B4—C1—B6—B104.42 (16)C1—B6—B11—B72.08 (15)
B3—C1—B6—B1066.13 (16)B10—B6—B11—B7100.74 (14)
C3—C1—B6—B11141.02 (13)B5—B6—B11—B762.45 (15)
C2—C1—B6—B1135.11 (11)C2—B6—B11—B1296.04 (15)
B5—C1—B6—B11102.86 (12)C1—B6—B11—B1261.49 (15)
B4—C1—B6—B1166.71 (15)B10—B6—B11—B1237.17 (12)
B3—C1—B6—B113.85 (16)B5—B6—B11—B121.13 (17)
C3—C1—B6—B5116.13 (13)C2—B6—B11—B10133.21 (14)
C2—C1—B6—B5137.97 (12)C1—B6—B11—B1098.66 (13)
B4—C1—B6—B536.15 (12)B5—B6—B11—B1038.30 (12)
B3—C1—B6—B5106.71 (13)B5—B9—B12—B763.56 (17)
C1—B5—B6—C234.99 (10)B4—B9—B12—B70.23 (17)
B10—B5—B6—C298.31 (13)B8—B9—B12—B737.39 (13)
B9—B5—B6—C261.00 (14)B10—B9—B12—B7100.62 (14)
B4—B5—B6—C22.37 (15)B5—B9—B12—B110.09 (17)
B10—B5—B6—C1133.30 (12)B4—B9—B12—B1163.70 (16)
B9—B5—B6—C195.99 (12)B8—B9—B12—B11100.87 (14)
B4—B5—B6—C132.62 (11)B10—B9—B12—B1137.15 (12)
C1—B5—B6—B10133.30 (12)B5—B9—B12—B8100.96 (14)
B9—B5—B6—B1037.32 (12)B4—B9—B12—B837.17 (12)
B4—B5—B6—B10100.68 (13)B10—B9—B12—B8138.01 (13)
C1—B5—B6—B1194.92 (13)B5—B9—B12—B1037.06 (12)
B10—B5—B6—B1138.38 (12)B4—B9—B12—B10100.85 (13)
B9—B5—B6—B111.07 (16)B8—B9—B12—B10138.01 (13)
B4—B5—B6—B1162.29 (15)C2—B7—B12—B961.20 (17)
C1—C2—B7—B1263.96 (17)B11—B7—B12—B9100.79 (14)
B11—C2—B7—B1240.51 (12)B3—B7—B12—B90.79 (18)
B6—C2—B7—B124.41 (19)B8—B7—B12—B937.51 (12)
B3—C2—B7—B12103.01 (14)C2—B7—B12—B1139.59 (12)
C1—C2—B7—B11104.47 (14)B3—B7—B12—B11101.58 (14)
B6—C2—B7—B1136.10 (13)B8—B7—B12—B11138.29 (13)
B3—C2—B7—B11143.52 (13)C2—B7—B12—B898.71 (14)
C1—C2—B7—B339.05 (12)B11—B7—B12—B8138.29 (13)
B11—C2—B7—B3143.52 (13)B3—B7—B12—B836.72 (12)
B6—C2—B7—B3107.42 (15)C2—B7—B12—B102.47 (18)
C1—C2—B7—B81.45 (17)B11—B7—B12—B1037.12 (13)
B11—C2—B7—B8103.02 (14)B3—B7—B12—B1064.46 (17)
B6—C2—B7—B866.92 (17)B8—B7—B12—B10101.17 (14)
B3—C2—B7—B840.50 (12)C2—B11—B12—B961.28 (16)
C1—B3—B7—C234.56 (11)B7—B11—B12—B9100.99 (14)
B8—B3—B7—C2133.06 (13)B10—B11—B12—B937.34 (12)
B4—B3—B7—C294.88 (13)B6—B11—B12—B90.75 (17)
C2—B3—B7—B1295.93 (14)C2—B11—B12—B739.71 (12)
C1—B3—B7—B1261.37 (16)B10—B11—B12—B7138.33 (14)
B8—B3—B7—B1237.13 (13)B6—B11—B12—B7101.74 (14)
B4—B3—B7—B121.04 (17)C2—B11—B12—B82.42 (16)
C2—B3—B7—B1132.25 (12)B7—B11—B12—B837.29 (12)
C1—B3—B7—B112.30 (17)B10—B11—B12—B8101.04 (14)
B8—B3—B7—B11100.80 (14)B6—B11—B12—B864.45 (16)
B4—B3—B7—B1162.63 (16)C2—B11—B12—B1098.62 (13)
C2—B3—B7—B8133.06 (13)B7—B11—B12—B10138.33 (14)
C1—B3—B7—B898.50 (13)B6—B11—B12—B1036.59 (12)
B4—B3—B7—B838.18 (12)B3—B8—B12—B9101.16 (13)
C2—B3—B8—B497.67 (13)B4—B8—B12—B936.94 (12)
C1—B3—B8—B439.42 (11)B7—B8—B12—B9138.21 (13)
B7—B3—B8—B4137.21 (13)B3—B8—B12—B737.05 (12)
C2—B3—B8—B739.55 (12)B4—B8—B12—B7101.26 (14)
C1—B3—B8—B797.79 (14)B9—B8—B12—B7138.21 (13)
B4—B3—B8—B7137.21 (13)B3—B8—B12—B110.24 (17)
C2—B3—B8—B960.21 (16)B4—B8—B12—B1163.97 (16)
C1—B3—B8—B91.96 (17)B7—B8—B12—B1137.29 (12)
B7—B3—B8—B999.75 (15)B9—B8—B12—B11100.91 (14)
B4—B3—B8—B937.46 (12)B3—B8—B12—B1063.48 (16)
C2—B3—B8—B122.75 (16)B4—B8—B12—B100.74 (17)
C1—B3—B8—B1260.99 (16)B7—B8—B12—B10100.53 (13)
B7—B3—B8—B1236.80 (13)B9—B8—B12—B1037.68 (12)
B4—B3—B8—B12100.42 (14)B6—B10—B12—B9101.17 (14)
C1—B4—B8—B339.97 (11)B5—B10—B12—B936.89 (11)
B9—B4—B8—B3138.14 (14)B11—B10—B12—B9138.35 (13)
B5—B4—B8—B3100.98 (14)B6—B10—B12—B70.04 (18)
C1—B4—B8—B71.60 (16)B5—B10—B12—B764.24 (16)
B9—B4—B8—B799.77 (14)B11—B10—B12—B737.22 (13)
B5—B4—B8—B762.61 (16)B9—B10—B12—B7101.13 (15)
B3—B4—B8—B738.37 (13)B6—B10—B12—B1137.19 (12)
C1—B4—B8—B998.17 (13)B5—B10—B12—B11101.47 (13)
B5—B4—B8—B937.16 (12)B9—B10—B12—B11138.35 (13)
B3—B4—B8—B9138.14 (14)B6—B10—B12—B863.47 (16)
C1—B4—B8—B1261.40 (15)B5—B10—B12—B80.81 (17)
B9—B4—B8—B1236.77 (12)B11—B10—B12—B8100.66 (14)
B5—B4—B8—B120.39 (17)B9—B10—B12—B837.69 (12)
B3—B4—B8—B12101.37 (14)C2—C1—C3—O22.6 (2)
C2—B7—B8—B340.49 (12)B5—C1—C3—O2137.41 (15)
B12—B7—B8—B3138.72 (13)B4—C1—C3—O2145.03 (15)
B11—B7—B8—B3101.30 (14)B6—C1—C3—O265.56 (18)
C2—B7—B8—B41.86 (17)B3—C1—C3—O271.49 (19)
B12—B7—B8—B4100.09 (14)C2—C1—C3—O1177.63 (12)
B11—B7—B8—B462.67 (16)B5—C1—C3—O142.31 (19)
B3—B7—B8—B438.63 (12)B4—C1—C3—O135.25 (19)
C2—B7—B8—B961.29 (16)B6—C1—C3—O1114.16 (14)
B12—B7—B8—B936.94 (12)B3—C1—C3—O1108.79 (15)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.95 (3)1.72 (3)2.6655 (16)177 (2)
Symmetry code: (i) x+1, y, z.

Experimental details

Crystal data
Chemical formulaC3H12B10O2
Mr188.23
Crystal system, space groupMonoclinic, P21/c
Temperature (K)160
a, b, c (Å)6.988 (2), 12.031 (3), 12.869 (4)
β (°) 103.33 (2)
V3)1052.8 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.07
Crystal size (mm)0.82 × 0.24 × 0.20
Data collection
DiffractometerBruker P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
2577, 1849, 1557
Rint0.041
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.119, 1.02
No. of reflections1849
No. of parameters184
No. of restraints10
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.21, 0.23

Computer programs: XSCANS (Bruker, 1996), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Bruker, 1999), SHELXTL.

Selected geometric parameters (Å, º) top
C1—C21.631 (2)B6—B101.759 (2)
C1—C31.507 (2)B6—B111.781 (3)
C1—B31.729 (2)B6—H61.099 (14)
C1—B41.710 (2)B7—B81.782 (3)
C1—B51.709 (2)B7—B111.777 (3)
C1—B61.728 (2)B7—B121.776 (3)
C2—B31.724 (3)B7—H71.091 (15)
C2—B61.723 (2)B8—B91.788 (3)
C2—B71.694 (2)B8—B121.790 (3)
C2—B111.690 (2)B8—H81.083 (14)
C2—H20.922 (19)B9—B101.789 (3)
B3—B41.795 (3)B9—B121.774 (3)
B3—B71.780 (3)B9—H91.114 (14)
B3—B81.766 (3)B10—B111.779 (3)
B3—H31.093 (14)B10—B121.794 (3)
B4—B51.785 (2)B10—H101.087 (14)
B4—B81.782 (2)B11—B121.778 (3)
B4—B91.780 (3)B11—H111.090 (15)
B4—H41.102 (14)B12—H121.103 (14)
B5—B61.791 (2)O1—C31.3051 (19)
B5—B91.780 (2)O1—H10.95 (3)
B5—B101.779 (3)O2—C31.2170 (19)
B5—H51.097 (14)
C3—C1—C2114.31 (12)C3—O1—H1106.0 (16)
C3—C1—B5122.84 (12)O2—C3—O1126.15 (14)
C2—C1—B4111.44 (11)O2—C3—C1121.19 (14)
C3—C1—B6113.67 (12)O1—C3—C1112.66 (13)
C3—C1—B3115.72 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.95 (3)1.72 (3)2.6655 (16)177 (2)
Symmetry code: (i) x+1, y, z.
 

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