Aqua­tri­fluorido­boron–1,3-dioxolan-2-one (1/2)

The crystal structure of the co-crystal of aqua­tri­fluorido­boron with two ethyl­ene carbonate (systematic name: 1,3-dioxolan-2-one) mol­ecules, BF₃H₂O·2OC(OCH₂)₂, was determined by low-temperature single-crystal X-ray diffraction. The co-crystal crystallizes in the ortho­rhom­bic space group P2₁2₁2₁ with four formula units per unit cell. The asymmetric unit consists of an aqua­tri­fluorido­boron mol­ecule and two ethyl­ene carbonate mol­ecules, connected by O—H...O=C hydrogen bonds. This crystal structure is an inter­esting example of a superacidic BF₃H₂O species co-crystallized with an organic carbonate.

Key indicators

Structure: I

• Single-crystal X-ray study
• T = 150 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.019
• wR factor = 0.050
• Data-to-parameter ratio = 10.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax < 18) ........       6.50 Note
PLAT313_ALERT_2_C Oxygen with Three Covalent Bonds (rare) ........         O1 Check

Alert level G
PLAT142_ALERT_4_G s.u. on b - Axis Small or Missing ..............    0.00008 Ang.
PLAT143_ALERT_4_G s.u. on c - Axis Small or Missing ..............    0.00009 Ang.
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O3       .      109.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O4       .      109.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O6       .      109.4 Degree
PLAT398_ALERT_2_G Deviating  C-O-C   Angle From 120 for O7       .      109.3 Degree
PLAT432_ALERT_2_G Short Inter X...Y Contact  F3       ..C4       .       2.93 Ang.
                                            1/2-x,1-y,1/2+z  =      2_565 Check
PLAT432_ALERT_2_G Short Inter X...Y Contact  O7       ..C4       .       2.97 Ang.
                                           -1/2+x,3/2-y,1-z  =      4_466 Check
PLAT802_ALERT_4_G CIF Input Record(s) with more than 80 Characters          6 Info
PLAT978_ALERT_2_G Number C-C Bonds with Positive Residual Density.          1 Info

   0 ALERT level A = Most likely a serious problem - resolve or explain
   0 ALERT level B = A potentially serious problem, consider carefully
   2 ALERT level C = Check. Ensure it is not caused by an omission or oversight
  10 ALERT level G = General information/check it is not something unexpected

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

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Computing details

Data collection: CrysAlis PRO (Rigaku OD, 2022); cell refinement: CrysAlis PRO (Rigaku OD, 2022); data reduction: CrysAlis PRO (Rigaku OD, 2022); program(s) used to solve structure: SHELXT (Sheldrick, 2015a); program(s) used to refine structure: SHELXL (Sheldrick, 2015b); molecular graphics: Olex2 (Dolomanov et al., 2009), DIAMOND (Brandenburg, 2005); software used to prepare material for publication: publCIF (Westrip, 2010).

Aquatrifluoridoboron–1,3-dioxolan-2-one (1/2)

Crystal data

2C3H4O3·H2BF3O	Dx = 1.701 Mg m^−3
Mr = 261.95	Cu Kα radiation, λ = 1.54184 Å
Orthorhombic, P212121	Cell parameters from 24984 reflections
a = 5.44197 (4) Å	θ = 4.6–75.5°
b = 13.09134 (8) Å	µ = 1.65 mm^−1
c = 14.36102 (9) Å	T = 150 K
V = 1023.12 (1) Å^3	Plate, clear colourless
Z = 4	0.18 × 0.08 × 0.05 mm
F(000) = 536

Data collection

XtaLAB Synergy, Dualflex, Eiger2 R CdTe 1M diffractometer	2134 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Cu) X-ray Source	2100 reflections with I > 2σ(I)
Mirror monochromator	Rint = 0.038
Detector resolution: 13.3333 pixels mm^-1	θmax = 76.1°, θmin = 4.6°
ω scans	h = −6→6
Absorption correction: gaussian (CrysAlisPro; Rigaku OD, 2022)	k = −15→16
Tmin = 0.663, Tmax = 1.000	l = −18→18
34542 measured reflections

Refinement

Refinement on F^2	All H-atom parameters refined
Least-squares matrix: full	w = 1/[σ^2(Fo^2) + (0.0311P)^2 + 0.1146P] where P = (Fo^2 + 2Fc^2)/3
R[F^2 > 2σ(F^2)] = 0.019	(Δ/σ)max < 0.001
wR(F^2) = 0.050	Δρmax = 0.11 e Å^−3
S = 1.04	Δρmin = −0.13 e Å^−3
2134 reflections	Extinction correction: SHELXL (Sheldrick, 2015b), Fc^* = kFc[1+0.001xFc^2λ^3/sin(2θ)]^–1/4
195 parameters	Extinction coefficient: 0.0035 (5)
0 restraints	Absolute structure: Flack x determined using 853 quotients [(I^+)–(I^–)]/[(I^+)+(I^–)] (Parsons et al., 2013)
Primary atom site location: dual	Absolute structure parameter: −0.05 (3)
Hydrogen site location: difference Fourier map

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
F1	0.05387 (16)	0.46158 (7)	0.69151 (6)	0.0345 (2)
F2	0.31541 (19)	0.57475 (6)	0.75716 (6)	0.0347 (2)
F3	0.35784 (17)	0.40399 (6)	0.78723 (6)	0.0320 (2)
O1	0.4683 (2)	0.46651 (8)	0.64281 (7)	0.0283 (2)
H1A	0.518 (5)	0.404 (2)	0.6252 (19)	0.071 (8)*
H1B	0.432 (5)	0.5005 (19)	0.5968 (17)	0.052 (6)*
O2	0.6234 (2)	0.29312 (8)	0.58425 (7)	0.0312 (2)
O3	0.29867 (18)	0.19871 (7)	0.62526 (7)	0.0266 (2)
O4	0.59130 (18)	0.13169 (7)	0.53775 (7)	0.0255 (2)
C1	0.5104 (2)	0.21312 (10)	0.58256 (9)	0.0232 (3)
C2	0.2189 (3)	0.09379 (11)	0.61128 (10)	0.0267 (3)
H2A	0.062 (4)	0.0949 (14)	0.5867 (13)	0.033 (5)*
H2B	0.220 (3)	0.0629 (13)	0.6729 (12)	0.025 (4)*
C3	0.4125 (3)	0.04997 (10)	0.54606 (10)	0.0249 (3)
H3A	0.349 (4)	0.0354 (14)	0.4844 (13)	0.031 (4)*
H3B	0.497 (4)	−0.0097 (15)	0.5697 (12)	0.030 (5)*
B1	0.2884 (3)	0.47702 (12)	0.72354 (11)	0.0252 (3)
O5	0.3601 (2)	0.59963 (8)	0.51501 (8)	0.0359 (3)
O6	0.60783 (19)	0.63618 (7)	0.39559 (7)	0.0280 (2)
O7	0.31353 (19)	0.74337 (7)	0.43534 (6)	0.0266 (2)
C4	0.4246 (3)	0.65572 (10)	0.45246 (9)	0.0240 (3)
C5	0.6409 (3)	0.72193 (11)	0.33235 (10)	0.0305 (3)
H5B	0.793 (4)	0.7521 (16)	0.3486 (14)	0.040 (5)*
H5A	0.649 (4)	0.6923 (14)	0.2694 (14)	0.038 (5)*
C6	0.4207 (3)	0.78959 (11)	0.35281 (10)	0.0291 (3)
H6B	0.470 (3)	0.8616 (15)	0.3687 (13)	0.032 (4)*
H6A	0.296 (4)	0.7853 (15)	0.3028 (14)	0.040 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
F1	0.0260 (4)	0.0419 (5)	0.0356 (4)	−0.0012 (4)	−0.0027 (3)	0.0046 (4)
F2	0.0475 (5)	0.0265 (4)	0.0300 (4)	0.0037 (4)	−0.0046 (4)	−0.0043 (3)
F3	0.0379 (5)	0.0309 (4)	0.0273 (4)	0.0026 (4)	−0.0013 (4)	0.0085 (3)
O1	0.0324 (5)	0.0254 (5)	0.0271 (5)	0.0034 (4)	0.0049 (4)	0.0046 (4)
O2	0.0325 (5)	0.0237 (4)	0.0373 (5)	−0.0033 (4)	0.0051 (5)	−0.0004 (4)
O3	0.0256 (5)	0.0243 (4)	0.0299 (5)	0.0006 (4)	0.0066 (4)	−0.0026 (4)
O4	0.0236 (5)	0.0243 (4)	0.0285 (5)	0.0008 (4)	0.0043 (4)	−0.0025 (4)
C1	0.0240 (6)	0.0236 (6)	0.0220 (6)	0.0025 (5)	0.0007 (5)	0.0016 (5)
C2	0.0243 (7)	0.0258 (6)	0.0300 (7)	−0.0032 (5)	0.0023 (6)	−0.0027 (5)
C3	0.0236 (6)	0.0234 (6)	0.0275 (6)	−0.0009 (5)	−0.0003 (5)	−0.0010 (5)
B1	0.0282 (8)	0.0253 (7)	0.0220 (7)	0.0020 (6)	−0.0007 (6)	0.0015 (5)
O5	0.0459 (6)	0.0315 (5)	0.0303 (5)	−0.0073 (5)	−0.0016 (5)	0.0098 (4)
O6	0.0299 (5)	0.0225 (4)	0.0314 (5)	0.0031 (4)	0.0017 (4)	−0.0006 (4)
O7	0.0303 (5)	0.0240 (4)	0.0255 (4)	0.0035 (4)	0.0055 (4)	0.0024 (4)
C4	0.0278 (7)	0.0212 (6)	0.0229 (6)	−0.0023 (5)	−0.0024 (5)	0.0002 (5)
C5	0.0343 (8)	0.0271 (7)	0.0302 (7)	−0.0041 (6)	0.0083 (6)	0.0000 (6)
C6	0.0355 (8)	0.0244 (7)	0.0273 (6)	0.0000 (6)	0.0034 (6)	0.0069 (5)

Geometric parameters (Å, º)

F1—B1	1.3718 (18)	C2—C3	1.522 (2)
F2—B1	1.3753 (17)	C3—H3A	0.969 (19)
F3—B1	1.3760 (17)	C3—H3B	0.97 (2)
O1—H1A	0.90 (3)	O5—C4	1.2122 (17)
O1—H1B	0.82 (3)	O6—C4	1.3139 (18)
O1—B1	1.5236 (18)	O6—C5	1.4550 (17)
O2—C1	1.2147 (17)	O7—C4	1.3200 (16)
O3—C1	1.3187 (16)	O7—C6	1.4530 (17)
O3—C2	1.4545 (16)	C5—H5B	0.95 (2)
O4—C1	1.3208 (16)	C5—H5A	0.98 (2)
O4—C3	1.4512 (17)	C5—C6	1.519 (2)
C2—H2A	0.92 (2)	C6—H6B	1.01 (2)
C2—H2B	0.972 (18)	C6—H6A	0.99 (2)
H1A—O1—H1B	110 (2)	F1—B1—O1	109.23 (11)
B1—O1—H1A	119.4 (18)	F2—B1—F3	112.57 (12)
B1—O1—H1B	114.2 (17)	F2—B1—O1	106.41 (12)
C1—O3—C2	109.38 (10)	F3—B1—O1	105.47 (11)
C1—O4—C3	109.35 (10)	C4—O6—C5	109.37 (11)
O2—C1—O3	123.81 (12)	C4—O7—C6	109.27 (11)
O2—C1—O4	122.46 (12)	O5—C4—O6	124.23 (13)
O3—C1—O4	113.73 (12)	O5—C4—O7	122.13 (14)
O3—C2—H2A	108.3 (12)	O6—C4—O7	113.64 (11)
O3—C2—H2B	105.4 (10)	O6—C5—H5B	106.1 (13)
O3—C2—C3	103.55 (11)	O6—C5—H5A	105.9 (11)
H2A—C2—H2B	110.9 (16)	O6—C5—C6	103.38 (11)
C3—C2—H2A	114.2 (12)	H5B—C5—H5A	110.5 (17)
C3—C2—H2B	113.6 (11)	C6—C5—H5B	113.6 (13)
O4—C3—C2	103.71 (11)	C6—C5—H5A	116.3 (12)
O4—C3—H3A	108.0 (11)	O7—C6—C5	103.40 (11)
O4—C3—H3B	107.7 (11)	O7—C6—H6B	108.2 (11)
C2—C3—H3A	112.9 (12)	O7—C6—H6A	107.1 (12)
C2—C3—H3B	114.7 (11)	C5—C6—H6B	112.2 (11)
H3A—C3—H3B	109.3 (16)	C5—C6—H6A	111.6 (11)
F1—B1—F2	110.75 (12)	H6B—C6—H6A	113.6 (15)
F1—B1—F3	112.08 (13)
O3—C2—C3—O4	5.22 (14)	O6—C5—C6—O7	9.38 (14)
C1—O3—C2—C3	−4.14 (14)	C4—O6—C5—C6	−7.83 (15)
C1—O4—C3—C2	−4.81 (14)	C4—O7—C6—C5	−8.29 (15)
C2—O3—C1—O2	−178.23 (13)	C5—O6—C4—O5	−177.25 (14)
C2—O3—C1—O4	1.26 (15)	C5—O6—C4—O7	2.92 (16)
C3—O4—C1—O2	−178.06 (13)	C6—O7—C4—O5	−176.09 (13)
C3—O4—C1—O3	2.44 (15)	C6—O7—C4—O6	3.74 (16)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1A···O2	0.90 (3)	1.67 (3)	2.5637 (15)	175 (3)
O1—H1B···O5	0.82 (3)	1.79 (3)	2.5985 (15)	166 (2)
C3—H3B···F3^i	0.97 (2)	2.474 (19)	3.3085 (16)	144.2 (14)
C6—H6B···F1^ii	1.01 (2)	2.51 (2)	3.3974 (17)	146.4 (14)

Symmetry codes: (i) −x+1, y−1/2, −z+3/2; (ii) x+1/2, −y+3/2, −z+1.