Diethyl ether-trichloro­borane, (C₂H₅)₂O-BCl₃

The title compound, C₄H₁₀BCl₃O, is the first crystallographically characterized example of a trihaloborane complex with an ether as electron-pair donor. The B atom is coordinated tetra­hedrally, whereas oxygen has a strongly distorted coordination environment. The central B-O bond length is 1.543 (2) Å and is thus longer than those in tetra­alkoxy­borates, B(OR)₄^-.

Key indicators

• Single-crystal X-ray study
• T = 100 K
• Mean [sigma](C-C) = 0.003 Å
• R factor = 0.033
• wR factor = 0.077
• Data-to-parameter ratio = 18.6

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT094_ALERT_2_C Ratio of Maximum / Minimum Residual Density ....       2.13
PLAT313_ALERT_2_C Oxygen with three covalent bonds (rare) ........          O

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   0 ALERT level G = General alerts; check

   0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   0 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1997); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: please provide; software used to prepare material for publication: CIFTAB (reference?).

Diethylether–trichloroborane

Crystal data

C4H10BCl3O	F(000) = 784
Mr = 191.28	Dx = 1.489 Mg m^−3
Orthorhombic, Pbcn	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2ab	Cell parameters from 9008 reflections
a = 11.4235 (6) Å	θ = 3.2–34.5°
b = 11.8071 (6) Å	µ = 1.00 mm^−1
c = 12.6502 (6) Å	T = 100 K
V = 1706.24 (15) Å^3	Block, colorless
Z = 8	0.45 × 0.35 × 0.15 mm

Data collection

Bruker SMART APEX diffractometer	2274 independent reflections
Radiation source: fine-focus sealed tube	2196 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.028
ω scans	θmax = 29.0°, θmin = 2.5°
Absorption correction: multi-scan (SADABS; Sheldrick, 2004)	h = −15→15
Tmin = 0.663, Tmax = 0.865	k = −16→16
24274 measured reflections	l = −17→17

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.033	Hydrogen site location: difference Fourier map
wR(F^2) = 0.077	All H-atom parameters refined
S = 1.33	w = 1/[σ^2(Fo^2) + (0.0258P)^2 + 1.1215P] where P = (Fo^2 + 2Fc^2)/3
2274 reflections	(Δ/σ)max = 0.001
122 parameters	Δρmax = 0.48 e Å^−3
0 restraints	Δρmin = −0.22 e Å^−3

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 (Ų)

	x	y	z	Uiso*/Ueq
Cl1	0.11021 (3)	0.06921 (4)	0.65190 (3)	0.02270 (11)
Cl2	0.36869 (4)	0.09858 (4)	0.68066 (3)	0.02491 (11)
Cl3	0.27608 (4)	−0.11523 (3)	0.57897 (4)	0.02953 (12)
O	0.26136 (9)	0.09470 (9)	0.48745 (8)	0.0165 (2)
C1	0.37763 (15)	0.09624 (17)	0.43331 (14)	0.0250 (3)
H1A	0.3826 (19)	0.028 (2)	0.3952 (18)	0.031 (6)*
H1B	0.430 (2)	0.0982 (18)	0.4894 (18)	0.028 (6)*
C2	0.38711 (18)	0.19895 (19)	0.36425 (15)	0.0320 (4)
H2A	0.336 (2)	0.197 (2)	0.305 (2)	0.041 (7)*
H2B	0.464 (2)	0.203 (2)	0.3396 (19)	0.042 (7)*
H2C	0.369 (2)	0.267 (2)	0.4057 (19)	0.041 (7)*
C3	0.16248 (15)	0.07139 (15)	0.41245 (13)	0.0214 (3)
H3A	0.1183 (17)	0.0128 (18)	0.4421 (16)	0.021 (5)*
H3B	0.1984 (19)	0.0448 (19)	0.3504 (17)	0.027 (5)*
C4	0.08956 (16)	0.17657 (16)	0.39786 (15)	0.0270 (4)
H4A	0.060 (2)	0.2012 (19)	0.4660 (18)	0.031 (6)*
H4B	0.025 (2)	0.160 (2)	0.352 (2)	0.043 (7)*
H4C	0.134 (2)	0.236 (2)	0.367 (2)	0.040 (6)*
B	0.25473 (15)	0.03768 (14)	0.59704 (13)	0.0168 (3)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Cl1	0.01748 (17)	0.0307 (2)	0.01996 (18)	0.00000 (14)	0.00294 (13)	0.00346 (14)
Cl2	0.02141 (19)	0.0341 (2)	0.01921 (19)	−0.00515 (15)	−0.00637 (14)	−0.00119 (15)
Cl3	0.0377 (2)	0.01675 (18)	0.0342 (2)	0.00432 (15)	−0.00554 (18)	0.00066 (15)
O	0.0151 (5)	0.0204 (5)	0.0141 (5)	−0.0007 (4)	−0.0009 (4)	0.0000 (4)
C1	0.0182 (7)	0.0363 (9)	0.0203 (8)	0.0017 (6)	0.0059 (6)	−0.0023 (7)
C2	0.0287 (9)	0.0453 (11)	0.0220 (8)	−0.0089 (8)	0.0057 (7)	0.0049 (8)
C3	0.0225 (7)	0.0252 (8)	0.0166 (7)	−0.0047 (6)	−0.0065 (6)	−0.0009 (6)
C4	0.0254 (8)	0.0280 (9)	0.0276 (9)	0.0000 (7)	−0.0090 (7)	0.0066 (7)
B	0.0167 (7)	0.0181 (7)	0.0155 (7)	−0.0006 (6)	−0.0012 (6)	0.0008 (6)

Geometric parameters (Å, º)

Cl1—B	1.8292 (18)	C2—H2A	0.96 (3)
Cl2—B	1.8250 (17)	C2—H2B	0.94 (3)
Cl3—B	1.8361 (18)	C2—H2C	0.98 (3)
O—C1	1.4945 (19)	C3—C4	1.507 (2)
O—C3	1.5006 (18)	C3—H3A	0.93 (2)
O—B	1.5430 (19)	C3—H3B	0.94 (2)
C1—C2	1.499 (3)	C4—H4A	0.97 (2)
C1—H1A	0.94 (2)	C4—H4B	0.96 (3)
C1—H1B	0.93 (2)	C4—H4C	0.96 (3)
C1—O—C3	112.42 (12)	C4—C3—H3A	111.1 (12)
C1—O—B	117.43 (12)	O—C3—H3B	105.1 (13)
C3—O—B	116.82 (11)	C4—C3—H3B	114.5 (13)
O—C1—C2	109.95 (14)	H3A—C3—H3B	108.9 (18)
O—C1—H1A	106.2 (14)	C3—C4—H4A	109.3 (14)
C2—C1—H1A	112.8 (14)	C3—C4—H4B	109.4 (15)
O—C1—H1B	102.7 (14)	H4A—C4—H4B	109 (2)
C2—C1—H1B	112.4 (13)	C3—C4—H4C	111.5 (15)
H1A—C1—H1B	112.2 (19)	H4A—C4—H4C	109 (2)
C1—C2—H2A	113.1 (15)	H4B—C4—H4C	108 (2)
C1—C2—H2B	107.7 (16)	O—B—Cl2	108.29 (10)
H2A—C2—H2B	109 (2)	O—B—Cl1	107.24 (10)
C1—C2—H2C	109.7 (14)	Cl2—B—Cl1	110.10 (9)
H2A—C2—H2C	108 (2)	O—B—Cl3	108.10 (10)
H2B—C2—H2C	110 (2)	Cl2—B—Cl3	111.40 (9)
O—C3—C4	110.03 (13)	Cl1—B—Cl3	111.55 (9)
O—C3—H3A	106.8 (12)