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Acta Cryst. (2009). E65, o470    [ doi:10.1107/S160053680804275X ]

Oxybis(dimesitylborane) dichloromethane hemisolvate

J.-H. Son and J. D. Hoefelmeyer

Abstract top

The title compound, C36H44B2O·0.5CH2Cl2, contains an almost linear O-B-O linkage [177.23 (15)°] and approximately orthogonal [interplanar angles 89.49 (5) and 80.77 (4)°] trigonal planar B centers, consistent with the previously reported non-solvated structure [Cardinet al. (1983). J. Chem. Res. (S), p. 93]. Intermolecular C-H...[pi] interactions exist between mesityl groups, with a C-H...centroid separation of 3.6535 (18) Å. The dichloromethane molecules lie on twofold rotation axes.

Comment top

The overall geometry of the oxybis(dimesitylborane) molecule is very similar to the previously reported non-solvated structure (Cardin et al., 1983). In the title compound, B—O = 1.351 (2) Å and B1—O1—B2 = 177.23 (15)°, compared with the non-solvated structure where B—O = 1.36 (2) Å and B—O—B = 165.5 (12) °. The angle between the boron trigonal planes (ψ) is 87.16 (5) ° which is larger than that of the previous structure (85 °). Ab initio molecular orbital calculation of (H2B)2O (Fjeldberg et al., 1980) has predicted that as the B—O—B angle approaches linearity, the ψ angle should approach 90°, which is consistent with the present structure, showing B=O=B character. Orthogonality of the mesityl groups 89.49 (5) ° and 80.77 (4) ° attached on the same boron atom is a similar structural feature to the previous report (85.5 ° and 81.3 °; Cardin et al., 1983). Intermolecular C—H···π interaction between mesityl groups exists with C···π separation of 3.6535 (18) ° (Table 1).

Related literature top

For the non-solvated structure, see: Cardin et al. (1983). For molecular orbital calculations concerning the parent compound (H2B)2O, see: Fjeldberg et al. (1980). Cg is the centroid of the C19–C24 ring.

Experimental top

The title compound was isolated as a biproduct from the reaction of dimesitylboron fluoride and organolithium reagent in tetrahydrofuran. After removal of THF in vacuo, the residue was extracted with dichloromethane. The slow evaporation of dichloromethane under nitrogen atmosphere led to formation of colorless prismatic crystals. It is probable that unintended inclusion of water hydrolyzes the B—F bond to an intermediate borinic acid that undergoes condensation to form the B—O—B linkage.

Refinement top

H atoms were positioned geometrically with C—H (aromatic) = 0.95 Å and C—H (methyl) = 0.98 Å and allowed to ride on their parent atoms with Uiso(H) = 1.2Ueq(C) or Uiso(H) = 1.5Ueq(C), respectively.

Computing details top

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT (Bruker, 2003); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn with 50% probability. H atoms are omitted. Symmetry code (ii): -x, y, -z + 1/2.
[Figure 2] Fig. 2. Packing diagram seen along the b axis. Dashed lines represent intermolecular C—H···π interactions.
Oxybis(dimesitylborane) dichloromethane hemisolvate top
Crystal data top
C36H44B2O·0.5CH2Cl2F(000) = 2392
Mr = 556.80Dx = 1.152 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 9936 reflections
a = 36.563 (2) Åθ = 2.3–25.3°
b = 8.3129 (5) ŵ = 0.15 mm−1
c = 21.6346 (13) ÅT = 100 K
β = 102.459 (1)°Block, colourless
V = 6420.9 (6) Å30.80 × 0.35 × 0.28 mm
Z = 8
Data collection top
Bruker SMART APEXII
diffractometer		5864 independent reflections
Radiation source: fine-focus sealed tube4475 reflections with I > 2σ(I)
graphiteRint = 0.038
ω scansθmax = 25.4°, θmin = 1.9°
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		h = −44→44
Tmin = 0.892, Tmax = 0.960k = −10→10
30958 measured reflectionsl = −26→26
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0493P)2 + 6.3252P]
where P = (Fo2 + 2Fc2)/3
5864 reflections(Δ/σ)max = 0.001
378 parametersΔρmax = 0.26 e Å−3
0 restraintsΔρmin = −0.23 e Å−3
Crystal data top
C36H44B2O·0.5CH2Cl2V = 6420.9 (6) Å3
Mr = 556.80Z = 8
Monoclinic, C2/cMo Kα radiation
a = 36.563 (2) ŵ = 0.15 mm−1
b = 8.3129 (5) ÅT = 100 K
c = 21.6346 (13) Å0.80 × 0.35 × 0.28 mm
β = 102.459 (1)°
Data collection top
Bruker SMART APEXII
diffractometer		5864 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2003)		4475 reflections with I > 2σ(I)
Tmin = 0.892, Tmax = 0.960Rint = 0.038
30958 measured reflectionsθmax = 25.4°
Refinement top
R[F2 > 2σ(F2)] = 0.039H-atom parameters constrained
wR(F2) = 0.108Δρmax = 0.26 e Å−3
S = 1.01Δρmin = −0.23 e Å−3
5864 reflectionsAbsolute structure: ?
378 parametersFlack parameter: ?
0 restraintsRogers parameter: ?
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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*/UeqOcc. (<1)
C10.07771 (4)0.97659 (19)0.14988 (7)0.0191 (3)
C20.07152 (5)1.1445 (2)0.14832 (7)0.0220 (4)
C30.03701 (5)1.2062 (2)0.11773 (8)0.0253 (4)
H30.03341.31950.11670.030*
C40.00763 (5)1.1077 (2)0.08862 (8)0.0257 (4)
C50.01413 (5)0.9432 (2)0.08895 (8)0.0246 (4)
H5−0.00530.87400.06810.030*
C60.04829 (4)0.8761 (2)0.11892 (7)0.0213 (4)
C70.10174 (5)1.2608 (2)0.17920 (9)0.0311 (4)
H7A0.12611.22240.17330.047*
H7B0.10211.26810.22450.047*
H7C0.09661.36710.15970.047*
C8−0.03016 (5)1.1762 (3)0.05847 (9)0.0371 (5)
H8A−0.02701.26330.02960.056*
H8B−0.04221.21820.09150.056*
H8C−0.04581.09140.03480.056*
C90.05242 (5)0.6951 (2)0.11911 (9)0.0280 (4)
H9A0.02880.64630.09720.042*
H9B0.05880.65620.16290.042*
H9C0.07230.66540.09730.042*
C100.14112 (4)0.77985 (19)0.16037 (7)0.0197 (3)
C110.15094 (4)0.8088 (2)0.10156 (8)0.0219 (4)
C120.17413 (5)0.7014 (2)0.07883 (8)0.0248 (4)
H120.18060.72320.03950.030*
C130.18803 (4)0.5636 (2)0.11187 (8)0.0252 (4)
C140.17800 (5)0.5345 (2)0.16928 (8)0.0245 (4)
H140.18700.43980.19220.029*
C150.15526 (4)0.6395 (2)0.19417 (8)0.0212 (4)
C160.13790 (5)0.9584 (2)0.06319 (8)0.0288 (4)
H16A0.14271.05310.09070.043*
H16B0.11100.95010.04490.043*
H16C0.15160.96880.02910.043*
C170.21420 (5)0.4514 (2)0.08774 (9)0.0348 (5)
H17A0.21350.47500.04310.052*
H17B0.20640.33990.09190.052*
H17C0.23980.46650.11250.052*
C180.14629 (5)0.5979 (2)0.25731 (8)0.0272 (4)
H18A0.15120.48340.26620.041*
H18B0.11980.62100.25600.041*
H18C0.16200.66230.29070.041*
C190.16666 (4)1.13716 (19)0.32859 (7)0.0197 (3)
C200.20008 (4)1.1459 (2)0.30583 (7)0.0208 (4)
C210.22615 (4)1.2665 (2)0.32754 (8)0.0228 (4)
H210.24861.27020.31210.027*
C220.22038 (5)1.3813 (2)0.37104 (8)0.0240 (4)
C230.18715 (5)1.3748 (2)0.39217 (8)0.0227 (4)
H230.18251.45360.42130.027*
C240.16034 (4)1.25578 (19)0.37186 (7)0.0205 (4)
C250.20941 (5)1.0248 (2)0.25940 (8)0.0274 (4)
H25A0.19471.04840.21690.041*
H25B0.20350.91630.27190.041*
H25C0.23621.03140.25930.041*
C260.24893 (5)1.5117 (2)0.39311 (10)0.0342 (4)
H26A0.24321.60530.36510.051*
H26B0.27401.47150.39210.051*
H26C0.24821.54320.43650.051*
C270.12447 (5)1.2611 (2)0.39576 (8)0.0270 (4)
H27A0.12571.18200.42980.040*
H27B0.10321.23580.36100.040*
H27C0.12121.36890.41200.040*
C280.12317 (4)0.88673 (19)0.36025 (7)0.0199 (3)
C290.14799 (5)0.82528 (19)0.41446 (7)0.0212 (4)
C300.13448 (5)0.7269 (2)0.45668 (8)0.0236 (4)
H300.15160.68570.49260.028*
C310.09701 (5)0.6873 (2)0.44793 (8)0.0258 (4)
C320.07272 (5)0.7474 (2)0.39490 (8)0.0261 (4)
H320.04690.72010.38790.031*
C330.08488 (5)0.8468 (2)0.35142 (8)0.0238 (4)
C340.18948 (5)0.8623 (2)0.42848 (8)0.0266 (4)
H34A0.19940.84110.39070.040*
H34B0.20240.79400.46330.040*
H34C0.19340.97570.44050.040*
C350.08310 (6)0.5840 (2)0.49550 (9)0.0352 (5)
H35A0.06050.52630.47430.053*
H35B0.07730.65230.52900.053*
H35C0.10250.50620.51410.053*
C360.05574 (5)0.9111 (2)0.29634 (8)0.0328 (4)
H36A0.03170.92120.30900.049*
H36B0.05310.83670.26050.049*
H36C0.06361.01680.28390.049*
C370.00000.3145 (3)0.25000.0362 (6)
H37A0.00870.24450.21910.043*0.50
H37B−0.00870.24460.28090.043*0.50
B10.11595 (5)0.9032 (2)0.18790 (8)0.0190 (4)
B20.13844 (5)0.9922 (2)0.31031 (9)0.0200 (4)
O10.12764 (3)0.95073 (13)0.24867 (5)0.0210 (3)
Cl10.037228 (16)0.43420 (8)0.28957 (3)0.05884 (19)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0227 (8)0.0190 (8)0.0168 (8)0.0005 (7)0.0068 (6)0.0006 (6)
C20.0266 (9)0.0217 (9)0.0188 (8)0.0010 (7)0.0074 (7)0.0008 (7)
C30.0330 (10)0.0213 (9)0.0234 (9)0.0060 (7)0.0101 (7)0.0024 (7)
C40.0247 (9)0.0332 (10)0.0196 (8)0.0080 (8)0.0062 (7)0.0030 (7)
C50.0205 (8)0.0311 (10)0.0222 (9)−0.0019 (7)0.0046 (7)−0.0015 (7)
C60.0236 (8)0.0233 (9)0.0180 (8)−0.0005 (7)0.0065 (7)0.0002 (7)
C70.0363 (10)0.0191 (9)0.0361 (10)−0.0011 (8)0.0037 (8)−0.0002 (8)
C80.0301 (10)0.0460 (12)0.0340 (10)0.0148 (9)0.0041 (8)0.0011 (9)
C90.0274 (9)0.0222 (9)0.0321 (10)−0.0024 (7)0.0009 (7)−0.0028 (8)
C100.0187 (8)0.0184 (8)0.0207 (8)−0.0022 (6)0.0013 (6)−0.0024 (7)
C110.0202 (8)0.0240 (9)0.0205 (8)−0.0010 (7)0.0020 (7)−0.0009 (7)
C120.0222 (9)0.0293 (10)0.0232 (9)−0.0010 (7)0.0060 (7)−0.0039 (7)
C130.0194 (8)0.0235 (9)0.0307 (9)0.0004 (7)0.0013 (7)−0.0082 (7)
C140.0232 (9)0.0184 (9)0.0290 (9)0.0014 (7)−0.0009 (7)−0.0003 (7)
C150.0201 (8)0.0191 (8)0.0226 (8)−0.0022 (7)0.0006 (6)−0.0008 (7)
C160.0336 (10)0.0300 (10)0.0248 (9)0.0050 (8)0.0108 (7)0.0045 (8)
C170.0266 (9)0.0358 (11)0.0408 (11)0.0071 (8)0.0045 (8)−0.0103 (9)
C180.0348 (10)0.0209 (9)0.0248 (9)0.0025 (7)0.0041 (7)0.0034 (7)
C190.0221 (8)0.0193 (8)0.0166 (8)0.0025 (7)0.0018 (6)0.0028 (6)
C200.0228 (8)0.0204 (8)0.0190 (8)0.0021 (7)0.0037 (7)0.0023 (7)
C210.0194 (8)0.0245 (9)0.0249 (9)0.0002 (7)0.0055 (7)0.0028 (7)
C220.0248 (9)0.0192 (9)0.0263 (9)0.0006 (7)0.0021 (7)0.0019 (7)
C230.0284 (9)0.0182 (8)0.0209 (8)0.0034 (7)0.0038 (7)−0.0002 (7)
C240.0227 (8)0.0193 (8)0.0186 (8)0.0027 (7)0.0027 (6)0.0032 (7)
C250.0239 (9)0.0320 (10)0.0283 (9)−0.0028 (8)0.0100 (7)−0.0069 (8)
C260.0311 (10)0.0260 (10)0.0460 (12)−0.0059 (8)0.0095 (8)−0.0080 (9)
C270.0291 (9)0.0249 (9)0.0281 (9)0.0007 (7)0.0088 (7)−0.0053 (7)
C280.0231 (8)0.0180 (8)0.0198 (8)−0.0012 (7)0.0069 (7)−0.0038 (7)
C290.0245 (9)0.0189 (8)0.0215 (8)0.0007 (7)0.0080 (7)−0.0037 (7)
C300.0315 (9)0.0192 (9)0.0209 (9)0.0019 (7)0.0072 (7)−0.0014 (7)
C310.0353 (10)0.0185 (9)0.0273 (9)−0.0007 (7)0.0151 (8)−0.0043 (7)
C320.0238 (9)0.0261 (9)0.0317 (10)−0.0058 (7)0.0135 (7)−0.0077 (8)
C330.0230 (9)0.0254 (9)0.0242 (9)−0.0016 (7)0.0078 (7)−0.0058 (7)
C340.0251 (9)0.0279 (10)0.0260 (9)0.0012 (7)0.0037 (7)0.0046 (7)
C350.0462 (11)0.0291 (10)0.0364 (11)−0.0050 (9)0.0222 (9)0.0006 (8)
C360.0211 (9)0.0478 (12)0.0299 (10)−0.0019 (8)0.0062 (7)0.0009 (9)
C370.0462 (16)0.0317 (15)0.0323 (15)0.0000.0118 (12)0.000
B10.0222 (9)0.0163 (9)0.0192 (9)−0.0046 (7)0.0063 (7)0.0022 (7)
B20.0183 (9)0.0219 (10)0.0193 (9)0.0042 (7)0.0030 (7)−0.0013 (7)
O10.0221 (6)0.0214 (6)0.0194 (6)0.0000 (5)0.0044 (5)−0.0001 (5)
Cl10.0454 (3)0.0613 (4)0.0605 (4)−0.0078 (3)−0.0092 (3)0.0073 (3)
Geometric parameters (Å, °) top
C1—C61.412 (2)C20—C211.393 (2)
C1—C21.413 (2)C20—C251.512 (2)
C1—B11.584 (2)C21—C221.388 (2)
C2—C31.390 (2)C21—H210.950
C2—C71.511 (2)C22—C231.389 (2)
C3—C41.389 (2)C22—C261.509 (2)
C3—H30.950C23—C241.395 (2)
C4—C51.388 (2)C23—H230.950
C4—C81.506 (2)C24—C271.511 (2)
C5—C61.393 (2)C25—H25A0.980
C5—H50.950C25—H25B0.980
C6—C91.512 (2)C25—H25C0.980
C7—H7A0.980C26—H26A0.980
C7—H7B0.980C26—H26B0.980
C7—H7C0.980C26—H26C0.980
C8—H8A0.980C27—H27A0.980
C8—H8B0.980C27—H27B0.980
C8—H8C0.980C27—H27C0.980
C9—H9A0.980C28—C331.411 (2)
C9—H9B0.980C28—C291.414 (2)
C9—H9C0.980C28—B21.584 (2)
C10—C151.414 (2)C29—C301.394 (2)
C10—C111.415 (2)C29—C341.513 (2)
C10—B11.578 (2)C30—C311.382 (2)
C11—C121.392 (2)C30—H300.950
C11—C161.514 (2)C31—C321.384 (2)
C12—C131.387 (2)C31—C351.511 (2)
C12—H120.950C32—C331.395 (2)
C13—C141.390 (2)C32—H320.950
C13—C171.508 (2)C33—C361.514 (2)
C14—C151.392 (2)C34—H34A0.980
C14—H140.950C34—H34B0.980
C15—C181.512 (2)C34—H34C0.980
C16—H16A0.980C35—H35A0.980
C16—H16B0.980C35—H35B0.980
C16—H16C0.980C35—H35C0.980
C17—H17A0.980C36—H36A0.980
C17—H17B0.980C36—H36B0.980
C17—H17C0.980C36—H36C0.980
C18—H18A0.980C37—Cl1i1.7530 (17)
C18—H18B0.980C37—Cl11.7530 (17)
C18—H18C0.980C37—H37A0.990
C19—C241.413 (2)C37—H37B0.990
C19—C201.414 (2)B1—O11.351 (2)
C19—B21.580 (2)B2—O11.351 (2)
C6—C1—C2118.13 (15)C22—C21—H21119.0
C6—C1—B1121.02 (14)C20—C21—H21119.0
C2—C1—B1120.80 (14)C21—C22—C23117.89 (15)
C3—C2—C1120.01 (16)C21—C22—C26120.84 (15)
C3—C2—C7118.45 (15)C23—C22—C26121.25 (16)
C1—C2—C7121.53 (15)C22—C23—C24121.97 (15)
C4—C3—C2122.14 (16)C22—C23—H23119.0
C4—C3—H3118.9C24—C23—H23119.0
C2—C3—H3118.9C23—C24—C19119.96 (15)
C5—C4—C3117.63 (15)C23—C24—C27118.31 (15)
C5—C4—C8120.96 (17)C19—C24—C27121.71 (15)
C3—C4—C8121.41 (17)C20—C25—H25A109.5
C4—C5—C6122.14 (16)C20—C25—H25B109.5
C4—C5—H5118.9H25A—C25—H25B109.5
C6—C5—H5118.9C20—C25—H25C109.5
C5—C6—C1119.91 (15)H25A—C25—H25C109.5
C5—C6—C9118.57 (15)H25B—C25—H25C109.5
C1—C6—C9121.48 (15)C22—C26—H26A109.5
C2—C7—H7A109.5C22—C26—H26B109.5
C2—C7—H7B109.5H26A—C26—H26B109.5
H7A—C7—H7B109.5C22—C26—H26C109.5
C2—C7—H7C109.5H26A—C26—H26C109.5
H7A—C7—H7C109.5H26B—C26—H26C109.5
H7B—C7—H7C109.5C24—C27—H27A109.5
C4—C8—H8A109.5C24—C27—H27B109.5
C4—C8—H8B109.5H27A—C27—H27B109.5
H8A—C8—H8B109.5C24—C27—H27C109.5
C4—C8—H8C109.5H27A—C27—H27C109.5
H8A—C8—H8C109.5H27B—C27—H27C109.5
H8B—C8—H8C109.5C33—C28—C29117.89 (15)
C6—C9—H9A109.5C33—C28—B2121.55 (14)
C6—C9—H9B109.5C29—C28—B2120.53 (14)
H9A—C9—H9B109.5C30—C29—C28120.04 (15)
C6—C9—H9C109.5C30—C29—C34118.02 (15)
H9A—C9—H9C109.5C28—C29—C34121.94 (15)
H9B—C9—H9C109.5C31—C30—C29122.08 (16)
C15—C10—C11118.03 (15)C31—C30—H30119.0
C15—C10—B1121.24 (14)C29—C30—H30119.0
C11—C10—B1120.71 (14)C30—C31—C32117.89 (16)
C12—C11—C10120.04 (15)C30—C31—C35120.77 (16)
C12—C11—C16118.46 (15)C32—C31—C35121.33 (16)
C10—C11—C16121.46 (15)C31—C32—C33122.14 (16)
C13—C12—C11122.05 (16)C31—C32—H32118.9
C13—C12—H12119.0C33—C32—H32118.9
C11—C12—H12119.0C32—C33—C28119.95 (15)
C12—C13—C14117.83 (16)C32—C33—C36117.84 (15)
C12—C13—C17121.43 (16)C28—C33—C36122.20 (15)
C14—C13—C17120.72 (16)C29—C34—H34A109.5
C13—C14—C15122.07 (16)C29—C34—H34B109.5
C13—C14—H14119.0H34A—C34—H34B109.5
C15—C14—H14119.0C29—C34—H34C109.5
C14—C15—C10119.97 (15)H34A—C34—H34C109.5
C14—C15—C18118.05 (15)H34B—C34—H34C109.5
C10—C15—C18121.97 (15)C31—C35—H35A109.5
C11—C16—H16A109.5C31—C35—H35B109.5
C11—C16—H16B109.5H35A—C35—H35B109.5
H16A—C16—H16B109.5C31—C35—H35C109.5
C11—C16—H16C109.5H35A—C35—H35C109.5
H16A—C16—H16C109.5H35B—C35—H35C109.5
H16B—C16—H16C109.5C33—C36—H36A109.5
C13—C17—H17A109.5C33—C36—H36B109.5
C13—C17—H17B109.5H36A—C36—H36B109.5
H17A—C17—H17B109.5C33—C36—H36C109.5
C13—C17—H17C109.5H36A—C36—H36C109.5
H17A—C17—H17C109.5H36B—C36—H36C109.5
H17B—C17—H17C109.5Cl1i—C37—Cl1110.83 (16)
C15—C18—H18A109.5Cl1i—C37—H37A109.5
C15—C18—H18B109.5Cl1—C37—H37A109.5
H18A—C18—H18B109.5Cl1i—C37—H37B109.5
C15—C18—H18C109.5Cl1—C37—H37B109.5
H18A—C18—H18C109.5H37A—C37—H37B108.1
H18B—C18—H18C109.5O1—B1—C10118.02 (14)
C24—C19—C20118.17 (15)O1—B1—C1116.82 (14)
C24—C19—B2120.44 (14)C10—B1—C1125.16 (14)
C20—C19—B2121.24 (14)O1—B2—C19118.53 (15)
C21—C20—C19119.94 (15)O1—B2—C28117.44 (15)
C21—C20—C25117.82 (14)C19—B2—C28123.98 (14)
C19—C20—C25122.22 (15)B1—O1—B2177.23 (15)
C22—C21—C20122.04 (15)
C6—C1—C2—C31.0 (2)C21—C22—C23—C241.2 (2)
B1—C1—C2—C3−176.35 (14)C26—C22—C23—C24179.48 (16)
C6—C1—C2—C7−178.85 (15)C22—C23—C24—C190.1 (2)
B1—C1—C2—C73.8 (2)C22—C23—C24—C27−178.11 (15)
C1—C2—C3—C40.7 (2)C20—C19—C24—C23−1.6 (2)
C7—C2—C3—C4−179.45 (16)B2—C19—C24—C23174.05 (14)
C2—C3—C4—C5−2.2 (2)C20—C19—C24—C27176.55 (15)
C2—C3—C4—C8176.96 (16)B2—C19—C24—C27−7.8 (2)
C3—C4—C5—C62.1 (3)C33—C28—C29—C300.8 (2)
C8—C4—C5—C6−177.11 (16)B2—C28—C29—C30−177.25 (15)
C4—C5—C6—C1−0.4 (2)C33—C28—C29—C34−179.47 (15)
C4—C5—C6—C9177.65 (16)B2—C28—C29—C342.4 (2)
C2—C1—C6—C5−1.1 (2)C28—C29—C30—C31−0.6 (2)
B1—C1—C6—C5176.20 (14)C34—C29—C30—C31179.65 (15)
C2—C1—C6—C9−179.14 (15)C29—C30—C31—C320.6 (2)
B1—C1—C6—C9−1.8 (2)C29—C30—C31—C35−178.36 (16)
C15—C10—C11—C12−0.6 (2)C30—C31—C32—C33−0.9 (3)
B1—C10—C11—C12177.98 (15)C35—C31—C32—C33178.12 (16)
C15—C10—C11—C16−178.30 (15)C31—C32—C33—C281.1 (3)
B1—C10—C11—C160.2 (2)C31—C32—C33—C36−177.72 (16)
C10—C11—C12—C130.6 (2)C29—C28—C33—C32−1.1 (2)
C16—C11—C12—C13178.41 (15)B2—C28—C33—C32177.00 (15)
C11—C12—C13—C140.1 (2)C29—C28—C33—C36177.72 (15)
C11—C12—C13—C17−177.85 (16)B2—C28—C33—C36−4.2 (2)
C12—C13—C14—C15−0.9 (2)C15—C10—B1—O147.6 (2)
C17—C13—C14—C15177.08 (15)C11—C10—B1—O1−130.88 (16)
C13—C14—C15—C101.0 (2)C15—C10—B1—C1−132.37 (16)
C13—C14—C15—C18−179.35 (15)C11—C10—B1—C149.1 (2)
C11—C10—C15—C14−0.2 (2)C6—C1—B1—O1−126.16 (16)
B1—C10—C15—C14−178.73 (15)C2—C1—B1—O151.1 (2)
C11—C10—C15—C18−179.88 (15)C6—C1—B1—C1053.8 (2)
B1—C10—C15—C181.6 (2)C2—C1—B1—C10−128.94 (17)
C24—C19—C20—C211.8 (2)C24—C19—B2—O1134.99 (16)
B2—C19—C20—C21−173.80 (14)C20—C19—B2—O1−49.5 (2)
C24—C19—C20—C25−179.95 (15)C24—C19—B2—C28−47.7 (2)
B2—C19—C20—C254.4 (2)C20—C19—B2—C28127.76 (17)
C19—C20—C21—C22−0.5 (2)C33—C28—B2—O1−48.1 (2)
C25—C20—C21—C22−178.86 (15)C29—C28—B2—O1129.90 (16)
C20—C21—C22—C23−1.0 (2)C33—C28—B2—C19134.60 (17)
C20—C21—C22—C26−179.27 (16)C29—C28—B2—C19−47.4 (2)
Symmetry codes: (i) −x, y, −z+1/2.
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···Cgii0.982.803.649 (4)145
Symmetry codes: (ii) x, y−1, z.
Table 1
Hydrogen-bond geometry (Å, °) top
D—H···AD—HH···AD···AD—H···A
C18—H18A···Cgi0.982.803.649 (4)145
Symmetry codes: (i) x, y−1, z.
Acknowledgements top

This work was supported by funding from the South Dakota 2010 Initiative, Center for Research and Development of Light-Activated Materials. Purchase of the X-ray diffractometer was made possible with funds from the National Science Foundation (EPS-0554609).

references
References top

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