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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-.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806047118/hj3021sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806047118/hj3021Isup2.hkl
Contains datablock I

CCDC reference: 629916

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

Computing details top

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 top
Crystal data top
C4H10BCl3OF(000) = 784
Mr = 191.28Dx = 1.489 Mg m3
Orthorhombic, PbcnMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2n 2abCell parameters from 9008 reflections
a = 11.4235 (6) Åθ = 3.2–34.5°
b = 11.8071 (6) ŵ = 1.00 mm1
c = 12.6502 (6) ÅT = 100 K
V = 1706.24 (15) Å3Block, colorless
Z = 80.45 × 0.35 × 0.15 mm
Data collection top
Bruker SMART APEX
diffractometer
2274 independent reflections
Radiation source: fine-focus sealed tube2196 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.028
ω scansθmax = 29.0°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2004)
h = 1515
Tmin = 0.663, Tmax = 0.865k = 1616
24274 measured reflectionsl = 1717
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)] = 0.033Hydrogen site location: difference Fourier map
wR(F2) = 0.077All H-atom parameters refined
S = 1.33 w = 1/[σ2(Fo2) + (0.0258P)2 + 1.1215P]
where P = (Fo2 + 2Fc2)/3
2274 reflections(Δ/σ)max = 0.001
122 parametersΔρmax = 0.48 e Å3
0 restraintsΔρmin = 0.22 e Å3
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*/Ueq
Cl10.11021 (3)0.06921 (4)0.65190 (3)0.02270 (11)
Cl20.36869 (4)0.09858 (4)0.68066 (3)0.02491 (11)
Cl30.27608 (4)0.11523 (3)0.57897 (4)0.02953 (12)
O0.26136 (9)0.09470 (9)0.48745 (8)0.0165 (2)
C10.37763 (15)0.09624 (17)0.43331 (14)0.0250 (3)
H1A0.3826 (19)0.028 (2)0.3952 (18)0.031 (6)*
H1B0.430 (2)0.0982 (18)0.4894 (18)0.028 (6)*
C20.38711 (18)0.19895 (19)0.36425 (15)0.0320 (4)
H2A0.336 (2)0.197 (2)0.305 (2)0.041 (7)*
H2B0.464 (2)0.203 (2)0.3396 (19)0.042 (7)*
H2C0.369 (2)0.267 (2)0.4057 (19)0.041 (7)*
C30.16248 (15)0.07139 (15)0.41245 (13)0.0214 (3)
H3A0.1183 (17)0.0128 (18)0.4421 (16)0.021 (5)*
H3B0.1984 (19)0.0448 (19)0.3504 (17)0.027 (5)*
C40.08956 (16)0.17657 (16)0.39786 (15)0.0270 (4)
H4A0.060 (2)0.2012 (19)0.4660 (18)0.031 (6)*
H4B0.025 (2)0.160 (2)0.352 (2)0.043 (7)*
H4C0.134 (2)0.236 (2)0.367 (2)0.040 (6)*
B0.25473 (15)0.03768 (14)0.59704 (13)0.0168 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.01748 (17)0.0307 (2)0.01996 (18)0.00000 (14)0.00294 (13)0.00346 (14)
Cl20.02141 (19)0.0341 (2)0.01921 (19)0.00515 (15)0.00637 (14)0.00119 (15)
Cl30.0377 (2)0.01675 (18)0.0342 (2)0.00432 (15)0.00554 (18)0.00066 (15)
O0.0151 (5)0.0204 (5)0.0141 (5)0.0007 (4)0.0009 (4)0.0000 (4)
C10.0182 (7)0.0363 (9)0.0203 (8)0.0017 (6)0.0059 (6)0.0023 (7)
C20.0287 (9)0.0453 (11)0.0220 (8)0.0089 (8)0.0057 (7)0.0049 (8)
C30.0225 (7)0.0252 (8)0.0166 (7)0.0047 (6)0.0065 (6)0.0009 (6)
C40.0254 (8)0.0280 (9)0.0276 (9)0.0000 (7)0.0090 (7)0.0066 (7)
B0.0167 (7)0.0181 (7)0.0155 (7)0.0006 (6)0.0012 (6)0.0008 (6)
Geometric parameters (Å, º) top
Cl1—B1.8292 (18)C2—H2A0.96 (3)
Cl2—B1.8250 (17)C2—H2B0.94 (3)
Cl3—B1.8361 (18)C2—H2C0.98 (3)
O—C11.4945 (19)C3—C41.507 (2)
O—C31.5006 (18)C3—H3A0.93 (2)
O—B1.5430 (19)C3—H3B0.94 (2)
C1—C21.499 (3)C4—H4A0.97 (2)
C1—H1A0.94 (2)C4—H4B0.96 (3)
C1—H1B0.93 (2)C4—H4C0.96 (3)
C1—O—C3112.42 (12)C4—C3—H3A111.1 (12)
C1—O—B117.43 (12)O—C3—H3B105.1 (13)
C3—O—B116.82 (11)C4—C3—H3B114.5 (13)
O—C1—C2109.95 (14)H3A—C3—H3B108.9 (18)
O—C1—H1A106.2 (14)C3—C4—H4A109.3 (14)
C2—C1—H1A112.8 (14)C3—C4—H4B109.4 (15)
O—C1—H1B102.7 (14)H4A—C4—H4B109 (2)
C2—C1—H1B112.4 (13)C3—C4—H4C111.5 (15)
H1A—C1—H1B112.2 (19)H4A—C4—H4C109 (2)
C1—C2—H2A113.1 (15)H4B—C4—H4C108 (2)
C1—C2—H2B107.7 (16)O—B—Cl2108.29 (10)
H2A—C2—H2B109 (2)O—B—Cl1107.24 (10)
C1—C2—H2C109.7 (14)Cl2—B—Cl1110.10 (9)
H2A—C2—H2C108 (2)O—B—Cl3108.10 (10)
H2B—C2—H2C110 (2)Cl2—B—Cl3111.40 (9)
O—C3—C4110.03 (13)Cl1—B—Cl3111.55 (9)
O—C3—H3A106.8 (12)
 

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