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Acta Crystallogr Sect E Struct Rep Online. 2009 March 1; 65(Pt 3): o470.
Published online 2009 February 6. doi:  10.1107/S160053680804275X
PMCID: PMC2968469

Oxybis(dimesitylborane) dichloro­methane hemisolvate

Abstract

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(...)π inter­actions exist between mesityl groups, with a C—H(...)centroid separation of 3.6535 (18) Å. The dichloromethane mol­ecules lie on twofold rotation axes.

Related literature

For the non-solvated structure, see: Cardin et al. (1983 [triangle]). For mol­ecular orbital calculations concerning the parent compound (H2B)2O, see: Fjeldberg et al. (1980 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-65-0o470-scheme1.jpg

Experimental

Crystal data

  • C36H44B2O·0.5CH2Cl2
  • M r = 556.80
  • Monoclinic, An external file that holds a picture, illustration, etc.
Object name is e-65-0o470-efi2.jpg
  • a = 36.563 (2) Å
  • b = 8.3129 (5) Å
  • c = 21.6346 (13) Å
  • β = 102.459 (1)°
  • V = 6420.9 (6) Å3
  • Z = 8
  • Mo Kα radiation
  • μ = 0.15 mm−1
  • T = 100 (2) K
  • 0.80 × 0.35 × 0.28 mm

Data collection

  • Bruker SMART APEXII diffractometer
  • Absorption correction: multi-scan (SADABS; Bruker, 2003 [triangle]) T min = 0.892, T max = 0.960
  • 30958 measured reflections
  • 5864 independent reflections
  • 4475 reflections with I > 2σ(I)
  • R int = 0.038

Refinement

  • R[F 2 > 2σ(F 2)] = 0.039
  • wR(F 2) = 0.108
  • S = 1.01
  • 5864 reflections
  • 378 parameters
  • H-atom parameters constrained
  • Δρmax = 0.26 e Å−3
  • Δρmin = −0.23 e Å−3

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

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053680804275X/bi2327sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S160053680804275X/bi2327Isup2.hkl

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

Acknowledgments

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).

supplementary crystallographic information

Comment

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).

Experimental

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

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.

Figures

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.
Fig. 2.
Packing diagram seen along the b axis. Dashed lines represent intermolecular C—H···π interactions.

Crystal data

C36H44B2O·0.5CH2Cl2F(000) = 2392
Mr = 556.80Dx = 1.152 Mg m3
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 mm1
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

Bruker SMART APEXII diffractometer5864 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

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 = 1.01w = 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 Å3
0 restraintsΔρmin = −0.23 e Å3

Special details

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)

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)

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, °)

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, °)

D—H···AD—HH···AD···AD—H···A
C18—H18A···Cgii0.982.803.649 (4)145

Symmetry codes: (ii) x, y−1, z.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: BI2327).

References

  • Bruker (2003). SMART, SAINT and SADABS Bruker AXS Inc., Madison, Wisconsin, USA.
  • Cardin, C. H., Parge, H. E. & Wilson, J. W. (1983). J. Chem. Res. (S), p. 93.
  • Farrugia, L. J. (1997). J. Appl. Cryst.30, 565.
  • Fjeldberg, T., Gundersen, G., Jonvik, T., Seip, H. M. & Saebo, S. (1980). Acta Chem. Scand. Ser. A, 34, 547–565.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Spek, A. L. (2003). J. Appl. Cryst.36, 7–13.

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