Oxybis(dimesitylborane) dichloro­methane hemisolvate

Son, J.-H.; Hoefelmeyer, J.D.

doi:10.1107/S160053680804275X

organic compounds

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Volume 65| Part 3| March 2009| Page o470

doi:10.1107/S160053680804275X

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Oxybis(dimesitylborane) dichloromethane hemisolvate

Jung-Ho Son ^a and James D. Hoefelmeyer ^a ^*

^aDepartment of Chemistry, The University of South Dakota, 414 E. Clark St, Vermillion, SD 57069, USA
^*Correspondence e-mail: jhoefelm@usd.edu

(Received 20 November 2008; accepted 15 December 2008; online 6 February 2009)

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 ). For molecular orbital calculations concerning the parent compound (H₂B)₂O, see: Fjeldberg et al. (1980 ).

Experimental

Crystal data

C₃₆H₄₄B₂O·0.5CH₂Cl₂
M_r = 556.80
Monoclinic, C 2/c
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 ) 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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.108
S = 1.01
5864 reflections
378 parameters
H-atom parameters constrained
Δρ_max = 0.26 e Å⁻³
Δρ_min = −0.23 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯Cgⁱ	0.98	2.80	3.649 (4)	145
Symmetry code: (i) x, y-1, z. Cg is the centroid of the C19–C24 ring.

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

Supporting information

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

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

checkCIF report

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.

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

	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.

Oxybis(dimesitylborane) dichloromethane hemisolvate top

Crystal data top

C₃₆H₄₄B₂O·0.5CH₂Cl₂	F(000) = 2392
M_r = 556.80	D_x = 1.152 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 9936 reflections
a = 36.563 (2) Å	θ = 2.3–25.3°
b = 8.3129 (5) Å	µ = 0.15 mm⁻¹
c = 21.6346 (13) Å	T = 100 K
β = 102.459 (1)°	Block, colourless
V = 6420.9 (6) Å³	0.80 × 0.35 × 0.28 mm
Z = 8

Data collection top

Bruker SMART APEXII diffractometer	5864 independent reflections
Radiation source: fine-focus sealed tube	4475 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.038
ω scans	θ_max = 25.4°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2003)	h = −44→44
T_min = 0.892, T_max = 0.960	k = −10→10
30958 measured reflections	l = −26→26

Refinement top

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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	w = 1/[σ²(F_o²) + (0.0493P)² + 6.3252P] where P = (F_o² + 2F_c²)/3
5864 reflections	(Δ/σ)_max = 0.001
378 parameters	Δρ_max = 0.26 e Å⁻³
0 restraints	Δρ_min = −0.23 e Å⁻³

Crystal data top

C₃₆H₄₄B₂O·0.5CH₂Cl₂	V = 6420.9 (6) Å³
M_r = 556.80	Z = 8
Monoclinic, C2/c	Mo Kα radiation
a = 36.563 (2) Å	µ = 0.15 mm⁻¹
b = 8.3129 (5) Å	T = 100 K
c = 21.6346 (13) Å	0.80 × 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)
T_min = 0.892, T_max = 0.960	R_int = 0.038
30958 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.108	H-atom parameters constrained
S = 1.01	Δρ_max = 0.26 e Å⁻³
5864 reflections	Δρ_min = −0.23 e Å⁻³
378 parameters

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
C1	0.07771 (4)	0.97659 (19)	0.14988 (7)	0.0191 (3)
C2	0.07152 (5)	1.1445 (2)	0.14832 (7)	0.0220 (4)
C3	0.03701 (5)	1.2062 (2)	0.11773 (8)	0.0253 (4)
H3	0.0334	1.3195	0.1167	0.030*
C4	0.00763 (5)	1.1077 (2)	0.08862 (8)	0.0257 (4)
C5	0.01413 (5)	0.9432 (2)	0.08895 (8)	0.0246 (4)
H5	−0.0053	0.8740	0.0681	0.030*
C6	0.04829 (4)	0.8761 (2)	0.11892 (7)	0.0213 (4)
C7	0.10174 (5)	1.2608 (2)	0.17920 (9)	0.0311 (4)
H7A	0.1261	1.2224	0.1733	0.047*
H7B	0.1021	1.2681	0.2245	0.047*
H7C	0.0966	1.3671	0.1597	0.047*
C8	−0.03016 (5)	1.1762 (3)	0.05847 (9)	0.0371 (5)
H8A	−0.0270	1.2633	0.0296	0.056*
H8B	−0.0422	1.2182	0.0915	0.056*
H8C	−0.0458	1.0914	0.0348	0.056*
C9	0.05242 (5)	0.6951 (2)	0.11911 (9)	0.0280 (4)
H9A	0.0288	0.6463	0.0972	0.042*
H9B	0.0588	0.6562	0.1629	0.042*
H9C	0.0723	0.6654	0.0973	0.042*
C10	0.14112 (4)	0.77985 (19)	0.16037 (7)	0.0197 (3)
C11	0.15094 (4)	0.8088 (2)	0.10156 (8)	0.0219 (4)
C12	0.17413 (5)	0.7014 (2)	0.07883 (8)	0.0248 (4)
H12	0.1806	0.7232	0.0395	0.030*
C13	0.18803 (4)	0.5636 (2)	0.11187 (8)	0.0252 (4)
C14	0.17800 (5)	0.5345 (2)	0.16928 (8)	0.0245 (4)
H14	0.1870	0.4398	0.1922	0.029*
C15	0.15526 (4)	0.6395 (2)	0.19417 (8)	0.0212 (4)
C16	0.13790 (5)	0.9584 (2)	0.06319 (8)	0.0288 (4)
H16A	0.1427	1.0531	0.0907	0.043*
H16B	0.1110	0.9501	0.0449	0.043*
H16C	0.1516	0.9688	0.0291	0.043*
C17	0.21420 (5)	0.4514 (2)	0.08774 (9)	0.0348 (5)
H17A	0.2135	0.4750	0.0431	0.052*
H17B	0.2064	0.3399	0.0919	0.052*
H17C	0.2398	0.4665	0.1125	0.052*
C18	0.14629 (5)	0.5979 (2)	0.25731 (8)	0.0272 (4)
H18A	0.1512	0.4834	0.2662	0.041*
H18B	0.1198	0.6210	0.2560	0.041*
H18C	0.1620	0.6623	0.2907	0.041*
C19	0.16666 (4)	1.13716 (19)	0.32859 (7)	0.0197 (3)
C20	0.20008 (4)	1.1459 (2)	0.30583 (7)	0.0208 (4)
C21	0.22615 (4)	1.2665 (2)	0.32754 (8)	0.0228 (4)
H21	0.2486	1.2702	0.3121	0.027*
C22	0.22038 (5)	1.3813 (2)	0.37104 (8)	0.0240 (4)
C23	0.18715 (5)	1.3748 (2)	0.39217 (8)	0.0227 (4)
H23	0.1825	1.4536	0.4213	0.027*
C24	0.16034 (4)	1.25578 (19)	0.37186 (7)	0.0205 (4)
C25	0.20941 (5)	1.0248 (2)	0.25940 (8)	0.0274 (4)
H25A	0.1947	1.0484	0.2169	0.041*
H25B	0.2035	0.9163	0.2719	0.041*
H25C	0.2362	1.0314	0.2593	0.041*
C26	0.24893 (5)	1.5117 (2)	0.39311 (10)	0.0342 (4)
H26A	0.2432	1.6053	0.3651	0.051*
H26B	0.2740	1.4715	0.3921	0.051*
H26C	0.2482	1.5432	0.4365	0.051*
C27	0.12447 (5)	1.2611 (2)	0.39576 (8)	0.0270 (4)
H27A	0.1257	1.1820	0.4298	0.040*
H27B	0.1032	1.2358	0.3610	0.040*
H27C	0.1212	1.3689	0.4120	0.040*
C28	0.12317 (4)	0.88673 (19)	0.36025 (7)	0.0199 (3)
C29	0.14799 (5)	0.82528 (19)	0.41446 (7)	0.0212 (4)
C30	0.13448 (5)	0.7269 (2)	0.45668 (8)	0.0236 (4)
H30	0.1516	0.6857	0.4926	0.028*
C31	0.09701 (5)	0.6873 (2)	0.44793 (8)	0.0258 (4)
C32	0.07272 (5)	0.7474 (2)	0.39490 (8)	0.0261 (4)
H32	0.0469	0.7201	0.3879	0.031*
C33	0.08488 (5)	0.8468 (2)	0.35142 (8)	0.0238 (4)
C34	0.18948 (5)	0.8623 (2)	0.42848 (8)	0.0266 (4)
H34A	0.1994	0.8411	0.3907	0.040*
H34B	0.2024	0.7940	0.4633	0.040*
H34C	0.1934	0.9757	0.4405	0.040*
C35	0.08310 (6)	0.5840 (2)	0.49550 (9)	0.0352 (5)
H35A	0.0605	0.5263	0.4743	0.053*
H35B	0.0773	0.6523	0.5290	0.053*
H35C	0.1025	0.5062	0.5141	0.053*
C36	0.05574 (5)	0.9111 (2)	0.29634 (8)	0.0328 (4)
H36A	0.0317	0.9212	0.3090	0.049*
H36B	0.0531	0.8367	0.2605	0.049*
H36C	0.0636	1.0168	0.2839	0.049*
C37	0.0000	0.3145 (3)	0.2500	0.0362 (6)
H37A	0.0087	0.2445	0.2191	0.043*	0.50
H37B	−0.0087	0.2446	0.2809	0.043*	0.50
B1	0.11595 (5)	0.9032 (2)	0.18790 (8)	0.0190 (4)
B2	0.13844 (5)	0.9922 (2)	0.31031 (9)	0.0200 (4)
O1	0.12764 (3)	0.95073 (13)	0.24867 (5)	0.0210 (3)
Cl1	0.037228 (16)	0.43420 (8)	0.28957 (3)	0.05884 (19)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0227 (8)	0.0190 (8)	0.0168 (8)	0.0005 (7)	0.0068 (6)	0.0006 (6)
C2	0.0266 (9)	0.0217 (9)	0.0188 (8)	0.0010 (7)	0.0074 (7)	0.0008 (7)
C3	0.0330 (10)	0.0213 (9)	0.0234 (9)	0.0060 (7)	0.0101 (7)	0.0024 (7)
C4	0.0247 (9)	0.0332 (10)	0.0196 (8)	0.0080 (8)	0.0062 (7)	0.0030 (7)
C5	0.0205 (8)	0.0311 (10)	0.0222 (9)	−0.0019 (7)	0.0046 (7)	−0.0015 (7)
C6	0.0236 (8)	0.0233 (9)	0.0180 (8)	−0.0005 (7)	0.0065 (7)	0.0002 (7)
C7	0.0363 (10)	0.0191 (9)	0.0361 (10)	−0.0011 (8)	0.0037 (8)	−0.0002 (8)
C8	0.0301 (10)	0.0460 (12)	0.0340 (10)	0.0148 (9)	0.0041 (8)	0.0011 (9)
C9	0.0274 (9)	0.0222 (9)	0.0321 (10)	−0.0024 (7)	0.0009 (7)	−0.0028 (8)
C10	0.0187 (8)	0.0184 (8)	0.0207 (8)	−0.0022 (6)	0.0013 (6)	−0.0024 (7)
C11	0.0202 (8)	0.0240 (9)	0.0205 (8)	−0.0010 (7)	0.0020 (7)	−0.0009 (7)
C12	0.0222 (9)	0.0293 (10)	0.0232 (9)	−0.0010 (7)	0.0060 (7)	−0.0039 (7)
C13	0.0194 (8)	0.0235 (9)	0.0307 (9)	0.0004 (7)	0.0013 (7)	−0.0082 (7)
C14	0.0232 (9)	0.0184 (9)	0.0290 (9)	0.0014 (7)	−0.0009 (7)	−0.0003 (7)
C15	0.0201 (8)	0.0191 (8)	0.0226 (8)	−0.0022 (7)	0.0006 (6)	−0.0008 (7)
C16	0.0336 (10)	0.0300 (10)	0.0248 (9)	0.0050 (8)	0.0108 (7)	0.0045 (8)
C17	0.0266 (9)	0.0358 (11)	0.0408 (11)	0.0071 (8)	0.0045 (8)	−0.0103 (9)
C18	0.0348 (10)	0.0209 (9)	0.0248 (9)	0.0025 (7)	0.0041 (7)	0.0034 (7)
C19	0.0221 (8)	0.0193 (8)	0.0166 (8)	0.0025 (7)	0.0018 (6)	0.0028 (6)
C20	0.0228 (8)	0.0204 (8)	0.0190 (8)	0.0021 (7)	0.0037 (7)	0.0023 (7)
C21	0.0194 (8)	0.0245 (9)	0.0249 (9)	0.0002 (7)	0.0055 (7)	0.0028 (7)
C22	0.0248 (9)	0.0192 (9)	0.0263 (9)	0.0006 (7)	0.0021 (7)	0.0019 (7)
C23	0.0284 (9)	0.0182 (8)	0.0209 (8)	0.0034 (7)	0.0038 (7)	−0.0002 (7)
C24	0.0227 (8)	0.0193 (8)	0.0186 (8)	0.0027 (7)	0.0027 (6)	0.0032 (7)
C25	0.0239 (9)	0.0320 (10)	0.0283 (9)	−0.0028 (8)	0.0100 (7)	−0.0069 (8)
C26	0.0311 (10)	0.0260 (10)	0.0460 (12)	−0.0059 (8)	0.0095 (8)	−0.0080 (9)
C27	0.0291 (9)	0.0249 (9)	0.0281 (9)	0.0007 (7)	0.0088 (7)	−0.0053 (7)
C28	0.0231 (8)	0.0180 (8)	0.0198 (8)	−0.0012 (7)	0.0069 (7)	−0.0038 (7)
C29	0.0245 (9)	0.0189 (8)	0.0215 (8)	0.0007 (7)	0.0080 (7)	−0.0037 (7)
C30	0.0315 (9)	0.0192 (9)	0.0209 (9)	0.0019 (7)	0.0072 (7)	−0.0014 (7)
C31	0.0353 (10)	0.0185 (9)	0.0273 (9)	−0.0007 (7)	0.0151 (8)	−0.0043 (7)
C32	0.0238 (9)	0.0261 (9)	0.0317 (10)	−0.0058 (7)	0.0135 (7)	−0.0077 (8)
C33	0.0230 (9)	0.0254 (9)	0.0242 (9)	−0.0016 (7)	0.0078 (7)	−0.0058 (7)
C34	0.0251 (9)	0.0279 (10)	0.0260 (9)	0.0012 (7)	0.0037 (7)	0.0046 (7)
C35	0.0462 (11)	0.0291 (10)	0.0364 (11)	−0.0050 (9)	0.0222 (9)	0.0006 (8)
C36	0.0211 (9)	0.0478 (12)	0.0299 (10)	−0.0019 (8)	0.0062 (7)	0.0009 (9)
C37	0.0462 (16)	0.0317 (15)	0.0323 (15)	0.000	0.0118 (12)	0.000
B1	0.0222 (9)	0.0163 (9)	0.0192 (9)	−0.0046 (7)	0.0063 (7)	0.0022 (7)
B2	0.0183 (9)	0.0219 (10)	0.0193 (9)	0.0042 (7)	0.0030 (7)	−0.0013 (7)
O1	0.0221 (6)	0.0214 (6)	0.0194 (6)	0.0000 (5)	0.0044 (5)	−0.0001 (5)
Cl1	0.0454 (3)	0.0613 (4)	0.0605 (4)	−0.0078 (3)	−0.0092 (3)	0.0073 (3)

Geometric parameters (Å, º) top

C1—C6	1.412 (2)	C20—C21	1.393 (2)
C1—C2	1.413 (2)	C20—C25	1.512 (2)
C1—B1	1.584 (2)	C21—C22	1.388 (2)
C2—C3	1.390 (2)	C21—H21	0.950
C2—C7	1.511 (2)	C22—C23	1.389 (2)
C3—C4	1.389 (2)	C22—C26	1.509 (2)
C3—H3	0.950	C23—C24	1.395 (2)
C4—C5	1.388 (2)	C23—H23	0.950
C4—C8	1.506 (2)	C24—C27	1.511 (2)
C5—C6	1.393 (2)	C25—H25A	0.980
C5—H5	0.950	C25—H25B	0.980
C6—C9	1.512 (2)	C25—H25C	0.980
C7—H7A	0.980	C26—H26A	0.980
C7—H7B	0.980	C26—H26B	0.980
C7—H7C	0.980	C26—H26C	0.980
C8—H8A	0.980	C27—H27A	0.980
C8—H8B	0.980	C27—H27B	0.980
C8—H8C	0.980	C27—H27C	0.980
C9—H9A	0.980	C28—C33	1.411 (2)
C9—H9B	0.980	C28—C29	1.414 (2)
C9—H9C	0.980	C28—B2	1.584 (2)
C10—C15	1.414 (2)	C29—C30	1.394 (2)
C10—C11	1.415 (2)	C29—C34	1.513 (2)
C10—B1	1.578 (2)	C30—C31	1.382 (2)
C11—C12	1.392 (2)	C30—H30	0.950
C11—C16	1.514 (2)	C31—C32	1.384 (2)
C12—C13	1.387 (2)	C31—C35	1.511 (2)
C12—H12	0.950	C32—C33	1.395 (2)
C13—C14	1.390 (2)	C32—H32	0.950
C13—C17	1.508 (2)	C33—C36	1.514 (2)
C14—C15	1.392 (2)	C34—H34A	0.980
C14—H14	0.950	C34—H34B	0.980
C15—C18	1.512 (2)	C34—H34C	0.980
C16—H16A	0.980	C35—H35A	0.980
C16—H16B	0.980	C35—H35B	0.980
C16—H16C	0.980	C35—H35C	0.980
C17—H17A	0.980	C36—H36A	0.980
C17—H17B	0.980	C36—H36B	0.980
C17—H17C	0.980	C36—H36C	0.980
C18—H18A	0.980	C37—Cl1ⁱ	1.7530 (17)
C18—H18B	0.980	C37—Cl1	1.7530 (17)
C18—H18C	0.980	C37—H37A	0.990
C19—C24	1.413 (2)	C37—H37B	0.990
C19—C20	1.414 (2)	B1—O1	1.351 (2)
C19—B2	1.580 (2)	B2—O1	1.351 (2)

C6—C1—C2	118.13 (15)	C22—C21—H21	119.0
C6—C1—B1	121.02 (14)	C20—C21—H21	119.0
C2—C1—B1	120.80 (14)	C21—C22—C23	117.89 (15)
C3—C2—C1	120.01 (16)	C21—C22—C26	120.84 (15)
C3—C2—C7	118.45 (15)	C23—C22—C26	121.25 (16)
C1—C2—C7	121.53 (15)	C22—C23—C24	121.97 (15)
C4—C3—C2	122.14 (16)	C22—C23—H23	119.0
C4—C3—H3	118.9	C24—C23—H23	119.0
C2—C3—H3	118.9	C23—C24—C19	119.96 (15)
C5—C4—C3	117.63 (15)	C23—C24—C27	118.31 (15)
C5—C4—C8	120.96 (17)	C19—C24—C27	121.71 (15)
C3—C4—C8	121.41 (17)	C20—C25—H25A	109.5
C4—C5—C6	122.14 (16)	C20—C25—H25B	109.5
C4—C5—H5	118.9	H25A—C25—H25B	109.5
C6—C5—H5	118.9	C20—C25—H25C	109.5
C5—C6—C1	119.91 (15)	H25A—C25—H25C	109.5
C5—C6—C9	118.57 (15)	H25B—C25—H25C	109.5
C1—C6—C9	121.48 (15)	C22—C26—H26A	109.5
C2—C7—H7A	109.5	C22—C26—H26B	109.5
C2—C7—H7B	109.5	H26A—C26—H26B	109.5
H7A—C7—H7B	109.5	C22—C26—H26C	109.5
C2—C7—H7C	109.5	H26A—C26—H26C	109.5
H7A—C7—H7C	109.5	H26B—C26—H26C	109.5
H7B—C7—H7C	109.5	C24—C27—H27A	109.5
C4—C8—H8A	109.5	C24—C27—H27B	109.5
C4—C8—H8B	109.5	H27A—C27—H27B	109.5
H8A—C8—H8B	109.5	C24—C27—H27C	109.5
C4—C8—H8C	109.5	H27A—C27—H27C	109.5
H8A—C8—H8C	109.5	H27B—C27—H27C	109.5
H8B—C8—H8C	109.5	C33—C28—C29	117.89 (15)
C6—C9—H9A	109.5	C33—C28—B2	121.55 (14)
C6—C9—H9B	109.5	C29—C28—B2	120.53 (14)
H9A—C9—H9B	109.5	C30—C29—C28	120.04 (15)
C6—C9—H9C	109.5	C30—C29—C34	118.02 (15)
H9A—C9—H9C	109.5	C28—C29—C34	121.94 (15)
H9B—C9—H9C	109.5	C31—C30—C29	122.08 (16)
C15—C10—C11	118.03 (15)	C31—C30—H30	119.0
C15—C10—B1	121.24 (14)	C29—C30—H30	119.0
C11—C10—B1	120.71 (14)	C30—C31—C32	117.89 (16)
C12—C11—C10	120.04 (15)	C30—C31—C35	120.77 (16)
C12—C11—C16	118.46 (15)	C32—C31—C35	121.33 (16)
C10—C11—C16	121.46 (15)	C31—C32—C33	122.14 (16)
C13—C12—C11	122.05 (16)	C31—C32—H32	118.9
C13—C12—H12	119.0	C33—C32—H32	118.9
C11—C12—H12	119.0	C32—C33—C28	119.95 (15)
C12—C13—C14	117.83 (16)	C32—C33—C36	117.84 (15)
C12—C13—C17	121.43 (16)	C28—C33—C36	122.20 (15)
C14—C13—C17	120.72 (16)	C29—C34—H34A	109.5
C13—C14—C15	122.07 (16)	C29—C34—H34B	109.5
C13—C14—H14	119.0	H34A—C34—H34B	109.5
C15—C14—H14	119.0	C29—C34—H34C	109.5
C14—C15—C10	119.97 (15)	H34A—C34—H34C	109.5
C14—C15—C18	118.05 (15)	H34B—C34—H34C	109.5
C10—C15—C18	121.97 (15)	C31—C35—H35A	109.5
C11—C16—H16A	109.5	C31—C35—H35B	109.5
C11—C16—H16B	109.5	H35A—C35—H35B	109.5
H16A—C16—H16B	109.5	C31—C35—H35C	109.5
C11—C16—H16C	109.5	H35A—C35—H35C	109.5
H16A—C16—H16C	109.5	H35B—C35—H35C	109.5
H16B—C16—H16C	109.5	C33—C36—H36A	109.5
C13—C17—H17A	109.5	C33—C36—H36B	109.5
C13—C17—H17B	109.5	H36A—C36—H36B	109.5
H17A—C17—H17B	109.5	C33—C36—H36C	109.5
C13—C17—H17C	109.5	H36A—C36—H36C	109.5
H17A—C17—H17C	109.5	H36B—C36—H36C	109.5
H17B—C17—H17C	109.5	Cl1ⁱ—C37—Cl1	110.83 (16)
C15—C18—H18A	109.5	Cl1ⁱ—C37—H37A	109.5
C15—C18—H18B	109.5	Cl1—C37—H37A	109.5
H18A—C18—H18B	109.5	Cl1ⁱ—C37—H37B	109.5
C15—C18—H18C	109.5	Cl1—C37—H37B	109.5
H18A—C18—H18C	109.5	H37A—C37—H37B	108.1
H18B—C18—H18C	109.5	O1—B1—C10	118.02 (14)
C24—C19—C20	118.17 (15)	O1—B1—C1	116.82 (14)
C24—C19—B2	120.44 (14)	C10—B1—C1	125.16 (14)
C20—C19—B2	121.24 (14)	O1—B2—C19	118.53 (15)
C21—C20—C19	119.94 (15)	O1—B2—C28	117.44 (15)
C21—C20—C25	117.82 (14)	C19—B2—C28	123.98 (14)
C19—C20—C25	122.22 (15)	B1—O1—B2	177.23 (15)
C22—C21—C20	122.04 (15)

C6—C1—C2—C3	1.0 (2)	C21—C22—C23—C24	1.2 (2)
B1—C1—C2—C3	−176.35 (14)	C26—C22—C23—C24	179.48 (16)
C6—C1—C2—C7	−178.85 (15)	C22—C23—C24—C19	0.1 (2)
B1—C1—C2—C7	3.8 (2)	C22—C23—C24—C27	−178.11 (15)
C1—C2—C3—C4	0.7 (2)	C20—C19—C24—C23	−1.6 (2)
C7—C2—C3—C4	−179.45 (16)	B2—C19—C24—C23	174.05 (14)
C2—C3—C4—C5	−2.2 (2)	C20—C19—C24—C27	176.55 (15)
C2—C3—C4—C8	176.96 (16)	B2—C19—C24—C27	−7.8 (2)
C3—C4—C5—C6	2.1 (3)	C33—C28—C29—C30	0.8 (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—C9	177.65 (16)	B2—C28—C29—C34	2.4 (2)
C2—C1—C6—C5	−1.1 (2)	C28—C29—C30—C31	−0.6 (2)
B1—C1—C6—C5	176.20 (14)	C34—C29—C30—C31	179.65 (15)
C2—C1—C6—C9	−179.14 (15)	C29—C30—C31—C32	0.6 (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—C12	177.98 (15)	C35—C31—C32—C33	178.12 (16)
C15—C10—C11—C16	−178.30 (15)	C31—C32—C33—C28	1.1 (3)
B1—C10—C11—C16	0.2 (2)	C31—C32—C33—C36	−177.72 (16)
C10—C11—C12—C13	0.6 (2)	C29—C28—C33—C32	−1.1 (2)
C16—C11—C12—C13	178.41 (15)	B2—C28—C33—C32	177.00 (15)
C11—C12—C13—C14	0.1 (2)	C29—C28—C33—C36	177.72 (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—O1	47.6 (2)
C17—C13—C14—C15	177.08 (15)	C11—C10—B1—O1	−130.88 (16)
C13—C14—C15—C10	1.0 (2)	C15—C10—B1—C1	−132.37 (16)
C13—C14—C15—C18	−179.35 (15)	C11—C10—B1—C1	49.1 (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—O1	51.1 (2)
C11—C10—C15—C18	−179.88 (15)	C6—C1—B1—C10	53.8 (2)
B1—C10—C15—C18	1.6 (2)	C2—C1—B1—C10	−128.94 (17)
C24—C19—C20—C21	1.8 (2)	C24—C19—B2—O1	134.99 (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—C25	4.4 (2)	C20—C19—B2—C28	127.76 (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—O1	129.90 (16)
C20—C21—C22—C23	−1.0 (2)	C33—C28—B2—C19	134.60 (17)
C20—C21—C22—C26	−179.27 (16)	C29—C28—B2—C19	−47.4 (2)

Symmetry code: (i) −x, y, −z+1/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cgⁱⁱ	0.98	2.80	3.649 (4)	145

Symmetry code: (ii) x, y−1, z.

Experimental details

Crystal data
Chemical formula	C₃₆H₄₄B₂O·0.5CH₂Cl₂
M_r	556.80
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	36.563 (2), 8.3129 (5), 21.6346 (13)
β (°)	102.459 (1)
V (Å³)	6420.9 (6)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.15
Crystal size (mm)	0.80 × 0.35 × 0.28

Data collection
Diffractometer	Bruker SMART APEXII diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2003)
T_min, T_max	0.892, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	30958, 5864, 4475
R_int	0.038
(sin θ/λ)_max (Å⁻¹)	0.603

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.108, 1.01
No. of reflections	5864
No. of parameters	378
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.26, −0.23

Computer programs: SMART (Bruker, 2003), SAINT (Bruker, 2003), SHELXTL (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···Cgⁱ	0.98	2.80	3.649 (4)	145

Symmetry code: (i) x, y−1, z.

Acknowledgements

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

Bruker (2003). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Cardin, C. H., Parge, H. E. & Wilson, J. W. (1983). J. Chem. Res. (S), p. 93. Google Scholar
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Fjeldberg, T., Gundersen, G., Jonvik, T., Seip, H. M. & Saebo, S. (1980). Acta Chem. Scand. Ser. A, 34, 547–565. CrossRef Web of Science Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2003). J. Appl. Cryst. 36, 7–13. Web of Science CrossRef CAS IUCr Journals Google Scholar