The 1:1 adduct of anti­mony trifluoride with [1.5]dibenzothia-18-crown-6

In the title compound [systematic name: 6,7,9,10,12,13,15,16-octa­hydro­dibenzo[n,q][1,4,7,10,13,16]penta­oxathia­cyclo­octa­decine anti­mony(III) trifluoride clathrate], (C₂₀H₂₄O₅S)SbF₃], the components are held together via electrostatic inter­actions between the anti­mony lone pair and the collective electron system of the macrocycle. The anti­mony trifluoride mol­ecule is situated in a perching mode above the macrocyclic cavity, its coordination being completed by three crown ether O atoms at distances in the range 2.737 (1)–3.136 (1) Å. Neighboring 1:1 adducts are linked into chains via C—H...F hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 123 K
• Mean [sigma](C-C) = 0.003 Å
• Disorder in main residue
• R factor = 0.019
• wR factor = 0.045
• Data-to-parameter ratio = 14.2

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT301_ALERT_3_C Main Residue  Disorder .........................      19.00 Perc.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  O5      ..       2.90 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F1     ..  O4A     ..       2.92 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F2     ..  O4A     ..       2.84 Ang.
PLAT431_ALERT_2_C Short Inter HL..A Contact  F3     ..  O2      ..       2.90 Ang.
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          8
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      25.10 Deg.
              C5   -O3   -C5A     1.555   1.555   1.555
PLAT779_ALERT_2_C Suspect or Irrelevant (Bond) Angle in CIF ......      17.72 Deg.
              O5   -C9   -O5A     1.555   1.555   1.555

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   9 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
   6 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
   2 ALERT type 4 Improvement, methodology, query or suggestion


checkCIF publication errors

Alert level A
PUBL024_ALERT_1_A The number of authors is greater than 5.
              Please specify the role of each of the co-authors
              for your paper.

Author Response: Response: All authors made significant contribution in this work. The idea of synthesis of the initial crown ether belongs to Kamalov and Kotlyar. The idea of synthesis of the complex belongs to Gelmboldt and Ganin. The synthesis of crown ether was performed by Kotlyar. The synthesis of the complex was performed by Ganin. X-ray diffraction experiment was performed by Lipkowski. The analysis of diffraction data was performed by Fonari.

   1 ALERT level A = Data missing that is essential or data in wrong format
   0 ALERT level G = General alerts. Data that may be required is missing

---

Computing details

Data collection: COLLECT (Nonius, 1998); cell refinement: COLLECT and DENZO (Otwinowski & Minor, 1997); data reduction: COLLECT and DENZO; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

6,7,9,10,12,13,15,16- octahydrodibenzo[n,q][1,4,7,10,13,16]pentaoxathiacyclooctadecine antimony(III) trifluoride clathrate

Crystal data

(C20H24O5S)[SbF3]	Dx = 1.726 Mg m^−3
Mr = 555.20	Melting point: 463 K
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 10.5980 (2) Å	Cell parameters from 9674 reflections
b = 16.2930 (2) Å	θ = 1–27.5°
c = 13.2860 (2) Å	µ = 1.44 mm^−1
β = 111.3760 (9)°	T = 123 K
V = 2136.32 (6) Å^3	Prism, yellow
Z = 4	0.15 × 0.12 × 0.10 mm
F(000) = 1112

Data collection

Nonius KappaCCD area-detector diffractometer	3952 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.026
Graphite monochromator	θmax = 26.0°, θmin = 2.4°
φ–ω scans	h = −13→13
16182 measured reflections	k = −20→20
4190 independent reflections	l = −16→16

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)] = 0.019	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.046	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0225P)^2 + 2.0901P] where P = (Fo^2 + 2Fc^2)/3
4190 reflections	(Δ/σ)max = 0.001
296 parameters	Δρmax = 0.36 e Å^−3
0 restraints	Δρmin = −0.42 e Å^−3

Special details

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s 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 > σ(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	Occ. (<1)
Sb1	0.547592 (12)	0.149699 (7)	0.265930 (9)	0.01632 (5)
F1	0.48231 (11)	0.26212 (6)	0.24813 (9)	0.0253 (2)
F2	0.72626 (11)	0.19053 (7)	0.28737 (9)	0.0257 (2)
F3	0.58957 (12)	0.16422 (6)	0.41889 (9)	0.0251 (2)
S1	0.24900 (4)	0.13357 (3)	0.28462 (3)	0.01547 (9)
O1	0.42871 (12)	−0.00359 (7)	0.34900 (10)	0.0165 (3)
O2	0.70626 (13)	0.01825 (8)	0.36282 (10)	0.0198 (3)
O3	0.66769 (14)	0.03092 (9)	0.13796 (11)	0.0284 (3)
O4	0.5339 (11)	0.1819 (7)	0.0551 (7)	0.0190 (14)	0.628 (4)
O5	0.2678 (2)	0.1828 (2)	0.07323 (19)	0.0172 (6)	0.628 (4)
O4A	0.539 (2)	0.1854 (12)	0.0708 (12)	0.019 (3)*	0.372 (4)
O5A	0.2605 (5)	0.1536 (3)	0.0707 (4)	0.0127 (12)*	0.372 (4)
C1	0.53281 (18)	−0.06505 (11)	0.39486 (15)	0.0190 (4)
H1A	0.5356	−0.1035	0.3380	0.023*
H1B	0.5137	−0.0969	0.4512	0.023*
C2	0.66612 (18)	−0.02073 (11)	0.44335 (14)	0.0188 (4)
H2A	0.6586	0.0213	0.4947	0.023*
H2B	0.7370	−0.0604	0.4844	0.023*
C3	0.7602 (2)	−0.03707 (13)	0.30583 (18)	0.0346 (5)
H3A	0.6936	−0.0811	0.2725	0.041*
H3B	0.8437	−0.0628	0.3566	0.041*
C4	0.7914 (2)	0.00843 (13)	0.22006 (17)	0.0302 (5)
H4A	0.8454	0.0581	0.2511	0.036*
H4B	0.8448	−0.0268	0.1896	0.036*
C5	0.6710 (4)	0.0670 (2)	0.0412 (3)	0.0265 (8)	0.628 (4)
H5A	0.5954	0.0453	−0.0219	0.032*	0.628 (4)
H5B	0.7572	0.0528	0.0323	0.032*	0.628 (4)
C6	0.6587 (4)	0.1585 (2)	0.0466 (3)	0.0277 (9)	0.628 (4)
H6A	0.7345	0.1798	0.1099	0.033*	0.628 (4)
H6B	0.6655	0.1835	−0.0192	0.033*	0.628 (4)
C7	0.4181 (3)	0.1653 (2)	−0.0228 (3)	0.0260 (8)	0.628 (4)
H7A	0.3984	0.1061	−0.0207	0.031*	0.628 (4)
H7B	0.4267	0.1769	−0.0932	0.031*	0.628 (4)
C8	0.3024 (3)	0.2133 (2)	−0.0155 (2)	0.0224 (8)	0.628 (4)
H8A	0.3275	0.2720	−0.0038	0.027*	0.628 (4)
H8B	0.2233	0.2083	−0.0839	0.027*	0.628 (4)
C5A	0.7154 (6)	0.0916 (4)	0.0729 (5)	0.0223 (15)*	0.372 (4)
H5A1	0.7726	0.1347	0.1203	0.027*	0.372 (4)
H5A2	0.7683	0.0634	0.0352	0.027*	0.372 (4)
C6A	0.5889 (6)	0.1278 (3)	−0.0065 (4)	0.0203 (13)*	0.372 (4)
H6A1	0.5211	0.0849	−0.0420	0.024*	0.372 (4)
H6A2	0.6077	0.1603	−0.0624	0.024*	0.372 (4)
C7A	0.4038 (5)	0.2161 (4)	−0.0158 (4)	0.0162 (12)*	0.372 (4)
H7A1	0.3820	0.2711	0.0051	0.019*	0.372 (4)
H7A2	0.4150	0.2214	−0.0863	0.019*	0.372 (4)
C8A	0.2883 (5)	0.1585 (3)	−0.0277 (4)	0.0152 (12)*	0.372 (4)
H8A1	0.2061	0.1779	−0.0872	0.018*	0.372 (4)
H8A2	0.3109	0.1032	−0.0469	0.018*	0.372 (4)
C9	0.16420 (18)	0.21539 (12)	0.08784 (14)	0.0208 (4)
C10	0.13817 (18)	0.19722 (10)	0.18170 (14)	0.0164 (4)
C11	0.21004 (18)	0.03254 (10)	0.23083 (14)	0.0152 (3)
C12	0.30777 (17)	−0.02899 (10)	0.27364 (14)	0.0152 (3)
C13	0.27822 (18)	−0.10965 (11)	0.23909 (15)	0.0190 (4)
H13A	0.3428	−0.1518	0.2696	0.023*
C14	0.15347 (19)	−0.12839 (11)	0.15946 (15)	0.0204 (4)
H14A	0.1339	−0.1834	0.1350	0.024*
C15	0.05805 (19)	−0.06777 (11)	0.11580 (15)	0.0217 (4)
H15A	−0.0265	−0.0809	0.0610	0.026*
C16	0.08635 (18)	0.01251 (11)	0.15238 (14)	0.0188 (4)
H16A	0.0201	0.0541	0.1233	0.023*
C17	0.0842 (2)	0.27355 (12)	0.01557 (15)	0.0272 (4)
H17A	0.1037	0.2879	−0.0466	0.033*
C18	−0.0233 (2)	0.31053 (12)	0.03366 (17)	0.0334 (5)
H18A	−0.0781	0.3494	−0.0168	0.040*
C19	−0.0514 (2)	0.29152 (13)	0.12385 (17)	0.0344 (5)
H19A	−0.1258	0.3166	0.1356	0.041*
C20	0.0298 (2)	0.23529 (12)	0.19802 (15)	0.0249 (4)
H20A	0.0109	0.2227	0.2609	0.030*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
Sb1	0.01774 (7)	0.01358 (7)	0.01508 (7)	−0.00293 (4)	0.00292 (5)	0.00103 (4)
F1	0.0265 (6)	0.0154 (5)	0.0324 (6)	−0.0008 (4)	0.0089 (5)	0.0040 (4)
F2	0.0197 (5)	0.0232 (6)	0.0299 (6)	−0.0065 (4)	0.0039 (5)	0.0017 (5)
F3	0.0323 (6)	0.0222 (5)	0.0158 (5)	−0.0009 (5)	0.0026 (5)	−0.0022 (4)
S1	0.0172 (2)	0.0145 (2)	0.0129 (2)	0.00118 (16)	0.00333 (17)	−0.00105 (16)
O1	0.0150 (6)	0.0139 (6)	0.0173 (6)	0.0016 (5)	0.0021 (5)	0.0007 (5)
O2	0.0206 (7)	0.0213 (6)	0.0188 (6)	0.0027 (5)	0.0086 (5)	0.0035 (5)
O3	0.0331 (8)	0.0331 (8)	0.0255 (7)	0.0118 (6)	0.0182 (6)	0.0118 (6)
O4	0.021 (2)	0.024 (2)	0.014 (3)	0.0033 (13)	0.010 (2)	0.005 (2)
O5	0.0209 (12)	0.0147 (15)	0.0166 (12)	0.0010 (11)	0.0075 (9)	0.0023 (10)
C1	0.0187 (9)	0.0150 (8)	0.0211 (9)	0.0046 (7)	0.0047 (7)	0.0041 (7)
C2	0.0190 (9)	0.0215 (9)	0.0152 (9)	0.0037 (7)	0.0054 (7)	0.0059 (7)
C3	0.0444 (13)	0.0345 (12)	0.0333 (12)	0.0247 (10)	0.0243 (11)	0.0157 (9)
C4	0.0285 (11)	0.0357 (12)	0.0331 (12)	0.0095 (9)	0.0192 (9)	0.0072 (9)
C5	0.036 (2)	0.0278 (19)	0.0234 (18)	0.0040 (17)	0.0206 (17)	0.0049 (16)
C6	0.0308 (19)	0.0293 (18)	0.0321 (19)	0.0020 (14)	0.0224 (16)	0.0089 (14)
C7	0.0273 (18)	0.033 (2)	0.0185 (16)	−0.0010 (14)	0.0091 (14)	−0.0011 (13)
C8	0.0246 (17)	0.0277 (19)	0.0142 (14)	0.0004 (13)	0.0062 (12)	0.0085 (12)
C9	0.0163 (9)	0.0258 (10)	0.0172 (9)	−0.0047 (7)	0.0024 (7)	−0.0010 (7)
C10	0.0188 (9)	0.0129 (8)	0.0143 (8)	−0.0006 (7)	0.0021 (7)	−0.0012 (6)
C11	0.0177 (9)	0.0155 (8)	0.0142 (8)	−0.0006 (7)	0.0080 (7)	−0.0014 (6)
C12	0.0155 (8)	0.0172 (8)	0.0138 (8)	−0.0007 (7)	0.0066 (7)	0.0005 (7)
C13	0.0195 (9)	0.0165 (9)	0.0217 (9)	0.0004 (7)	0.0084 (7)	−0.0001 (7)
C14	0.0227 (9)	0.0168 (9)	0.0231 (10)	−0.0033 (7)	0.0100 (8)	−0.0047 (7)
C15	0.0191 (9)	0.0240 (10)	0.0199 (9)	−0.0038 (7)	0.0047 (7)	−0.0053 (7)
C16	0.0162 (9)	0.0200 (9)	0.0193 (9)	0.0024 (7)	0.0055 (7)	−0.0008 (7)
C17	0.0309 (11)	0.0255 (10)	0.0164 (9)	−0.0113 (8)	−0.0018 (8)	0.0024 (8)
C18	0.0412 (13)	0.0177 (10)	0.0237 (11)	0.0050 (9)	−0.0090 (9)	−0.0021 (8)
C19	0.0353 (12)	0.0309 (11)	0.0278 (11)	0.0157 (9)	0.0007 (9)	−0.0086 (9)
C20	0.0268 (10)	0.0264 (10)	0.0188 (9)	0.0068 (8)	0.0049 (8)	−0.0050 (8)

Geometric parameters (Å, º)

Sb1—F2	1.9277 (11)	C7—C8	1.486 (5)
Sb1—F3	1.9299 (11)	C7—H7A	0.9900
Sb1—F1	1.9418 (11)	C7—H7B	0.9900
S1—C10	1.7760 (17)	C8—H8A	0.9900
S1—C11	1.7820 (17)	C8—H8B	0.9900
O1—C12	1.371 (2)	C5A—C6A	1.492 (8)
O1—C1	1.450 (2)	C5A—H5A1	0.9900
O2—C3	1.424 (2)	C5A—H5A2	0.9900
O2—C2	1.436 (2)	C6A—H6A1	0.9900
O3—C4	1.414 (2)	C6A—H6A2	0.9900
O3—C5	1.425 (3)	C7A—C8A	1.503 (7)
O3—C5A	1.516 (6)	C7A—H7A1	0.9900
O4—C7	1.313 (11)	C7A—H7A2	0.9900
O4—C6	1.419 (11)	C8A—H8A1	0.9900
O5—C9	1.297 (3)	C8A—H8A2	0.9900
O5—C8	1.444 (4)	C9—C17	1.395 (3)
O4A—C7A	1.56 (2)	C9—C10	1.403 (3)
O4A—C6A	1.614 (18)	C10—C20	1.390 (3)
O5A—C8A	1.444 (7)	C11—C16	1.384 (2)
O5A—C9	1.508 (5)	C11—C12	1.404 (2)
C1—C2	1.506 (2)	C12—C13	1.390 (2)
C1—H1A	0.9900	C13—C14	1.393 (3)
C1—H1B	0.9900	C13—H13A	0.9500
C2—H2A	0.9900	C14—C15	1.381 (3)
C2—H2B	0.9900	C14—H14A	0.9500
C3—C4	1.494 (3)	C15—C16	1.390 (3)
C3—H3A	0.9900	C15—H15A	0.9500
C3—H3B	0.9900	C16—H16A	0.9500
C4—H4A	0.9900	C17—C18	1.386 (3)
C4—H4B	0.9900	C17—H17A	0.9500
C5—C6	1.501 (5)	C18—C19	1.371 (3)
C5—H5A	0.9900	C18—H18A	0.9500
C5—H5B	0.9900	C19—C20	1.390 (3)
C6—H6A	0.9900	C19—H19A	0.9500
C6—H6B	0.9900	C20—H20A	0.9500
F2—Sb1—F3	88.00 (5)	C6A—C5A—H5A1	110.7
F2—Sb1—F1	88.83 (5)	O3—C5A—H5A1	110.7
F3—Sb1—F1	87.01 (5)	C6A—C5A—H5A2	110.7
C10—S1—C11	103.83 (8)	O3—C5A—H5A2	110.7
C12—O1—C1	117.65 (13)	H5A1—C5A—H5A2	108.8
C3—O2—C2	113.67 (14)	C5A—C6A—O4A	101.3 (8)
C4—O3—C5	118.8 (2)	C5A—C6A—H6A1	111.5
C4—O3—C5A	101.6 (3)	O4A—C6A—H6A1	111.5
C5—O3—C5A	25.1 (2)	C5A—C6A—H6A2	111.5
C7—O4—C6	120.8 (7)	O4A—C6A—H6A2	111.5
C9—O5—C8	117.5 (2)	H6A1—C6A—H6A2	109.3
C7A—O4A—C6A	98.2 (9)	C8A—C7A—O4A	111.9 (8)
C8A—O5A—C9	118.2 (4)	C8A—C7A—H7A1	109.2
O1—C1—C2	107.46 (14)	O4A—C7A—H7A1	109.2
O1—C1—H1A	110.2	C8A—C7A—H7A2	109.2
C2—C1—H1A	110.2	O4A—C7A—H7A2	109.2
O1—C1—H1B	110.2	H7A1—C7A—H7A2	107.9
C2—C1—H1B	110.2	O5A—C8A—C7A	111.5 (4)
H1A—C1—H1B	108.5	O5A—C8A—H8A1	109.3
O2—C2—C1	112.33 (14)	C7A—C8A—H8A1	109.3
O2—C2—H2A	109.1	O5A—C8A—H8A2	109.3
C1—C2—H2A	109.1	C7A—C8A—H8A2	109.3
O2—C2—H2B	109.1	H8A1—C8A—H8A2	108.0
C1—C2—H2B	109.1	O5—C9—C17	120.7 (2)
H2A—C2—H2B	107.9	O5—C9—C10	119.87 (19)
O2—C3—C4	109.56 (16)	C17—C9—C10	119.22 (18)
O2—C3—H3A	109.8	O5—C9—O5A	17.72 (19)
C4—C3—H3A	109.8	C17—C9—O5A	128.6 (2)
O2—C3—H3B	109.8	C10—C9—O5A	110.9 (2)
C4—C3—H3B	109.8	C20—C10—C9	119.06 (16)
H3A—C3—H3B	108.2	C20—C10—S1	119.51 (14)
O3—C4—C3	108.40 (17)	C9—C10—S1	121.22 (14)
O3—C4—H4A	110.0	C16—C11—C12	119.54 (16)
C3—C4—H4A	110.0	C16—C11—S1	122.50 (13)
O3—C4—H4B	110.0	C12—C11—S1	117.91 (13)
C3—C4—H4B	110.0	O1—C12—C13	124.37 (15)
H4A—C4—H4B	108.4	O1—C12—C11	115.81 (15)
O3—C5—C6	109.6 (3)	C13—C12—C11	119.82 (16)
O3—C5—H5A	109.7	C12—C13—C14	119.70 (16)
C6—C5—H5A	109.7	C12—C13—H13A	120.2
O3—C5—H5B	109.7	C14—C13—H13A	120.2
C6—C5—H5B	109.7	C15—C14—C13	120.60 (17)
H5A—C5—H5B	108.2	C15—C14—H14A	119.7
O4—C6—C5	111.7 (5)	C13—C14—H14A	119.7
O4—C6—H6A	109.3	C14—C15—C16	119.65 (17)
C5—C6—H6A	109.3	C14—C15—H15A	120.2
O4—C6—H6B	109.3	C16—C15—H15A	120.2
C5—C6—H6B	109.3	C11—C16—C15	120.65 (17)
H6A—C6—H6B	107.9	C11—C16—H16A	119.7
O4—C7—C8	113.4 (5)	C15—C16—H16A	119.7
O4—C7—H7A	108.9	C18—C17—C9	120.52 (19)
C8—C7—H7A	108.9	C18—C17—H17A	119.7
O4—C7—H7B	108.9	C9—C17—H17A	119.7
C8—C7—H7B	108.9	C19—C18—C17	120.50 (19)
H7A—C7—H7B	107.7	C19—C18—H18A	119.7
O5—C8—C7	109.4 (3)	C17—C18—H18A	119.7
O5—C8—H8A	109.8	C18—C19—C20	119.5 (2)
C7—C8—H8A	109.8	C18—C19—H19A	120.2
O5—C8—H8B	109.8	C20—C19—H19A	120.2
C7—C8—H8B	109.8	C10—C20—C19	121.11 (19)
H8A—C8—H8B	108.2	C10—C20—H20A	119.4
C6A—C5A—O3	105.1 (5)	C19—C20—H20A	119.4
O1—C1—C2—O2	−66.91 (18)	O4—C7—C8—O5	−72.4 (6)
C1—C2—O2—C3	−77.18 (19)	C7—C8—O5—C9	−176.7 (3)
C2—O2—C3—C4	176.81 (16)	C8—O5—C9—C10	−170.4 (2)
O2—C3—C4—O3	−70.5 (2)	O5—C9—C10—S1	2.8 (3)
C3—C4—O3—C5	−173.0 (2)	C9—C10—S1—C11	−76.52 (16)
C4—O3—C5—C6	−99.1 (3)	C10—S1—C11—C12	158.81 (14)
O3—C5—C6—O4	−61.7 (6)	S1—C11—C12—O1	−4.0 (2)
C5—C6—O4—C7	−63.3 (9)	C11—C12—O1—C1	−179.65 (15)
C6—O4—C7—C8	−163.8 (6)	C12—O1—C1—C2	160.99 (14)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1A···F1^i	0.99	2.45	3.368 (2)	155
C13—H13A···F1^i	0.95	2.40	3.244 (2)	147

Symmetry code: (i) −x+1, y−1/2, −z+1/2.