Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807044777/bt2508sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536807044777/bt2508Isup2.hkl |
CCDC reference: 663805
Analytical grade reagents were used. 1-(3'-Amino)propylsilatrane (Semenov et al., 2002) (400 mg, 1.72 mmol) was mixed in 30 ml dry dichloromethane under inert gas atmosphere. Triethylamine (470 µl, 3.44 mmol) was added. The reaction mixture was cooled (ice salt bath). Mixture of 2,3,4,5,6-pentafluorobenzoylchloride (240 µl, 1.72 mmol) and dry dichloromethane was added dropwise to the reaction flask. The reaction mixture was stirred at 0° C for 1 h and at the room temperature for 18 h. After that the mixture was washed with water, dried with MgSO4, filtered and evaporated. Yield 460 mg (63%). Colorless crystals were obtained from chloroform at room temperature via slow evaporation. (mp. 454.6–455.2 K). 1H-NMR (500 MHz, CDCl3)δ, p.p.m.: 0.509 (t. 2H), 1.736 (tt. 2H), 2.802 (t·6H), 3.454 (q. 2H), 3.718 (t. 6H), 6.923 (s. 1H). 13C NMR (126 MHz, CDCl3)δ, p.p.m.: -47.417, -38.863, -27.089, 12.856, 23.412, 43.013, 50.989, 57.550, 156.880. MS (ESI-TOF) 449 [M+Na].
All H atoms were visible in electron density maps, but were placed in idealized positions and allowed to ride on their parent atoms at C—H distances of 0.99 Å (methylene) and 0.88 Å for H—N with Uiso(H) of 1.2 times Ueq(C) and Ueq(N).
The title compound is a perfluorobenzamide derivative including a silatrane group (Fig. 1). A weak anion-π-type of interaction between the electron pair of the carbonyl oxygen O(8) and the two carbon atoms C(3) and C(4) of the perfluorobenzoic acid moiety creates a dimer. The interaction distances are 3.096 (3) and 3.036 (3) Å for the O(8)···C(3) and O(8)···C(4), respectively. Similar interaction but between the polarized iodine atoms in diiodotetrafluorobenzene and carbonyl oxygen has recently been observed in a study of halogen bonding (Russo et al., 2007). In addition a normal hydrogen bond, N···O = 2.954 (2) Å with angle of 172.45°, exists from the amide hydrogen to one of the silatrane O atoms, O(20). Also two short intermolecular contacts ranging from 3.027 to 3.406 Å between C—H and silatrane O atoms and three to the fluorine atoms, from 3.101 to 3.229 Å are observed.
For related literature, see: Russo et al. (2007); Semenov et al. (2002).
Data collection: COLLECT (Nonius, 2004); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).
Fig. 1. View of the molecule of (I) showing the atom-labeling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented by circles of arbitrary size. |
C16H19F5N2O4Si | F(000) = 880 |
Mr = 426.42 | Dx = 1.608 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71069 Å |
Hall symbol: -P 2yn | Cell parameters from 15147 reflections |
a = 15.2027 (4) Å | θ = 2.6–27.1° |
b = 7.6207 (2) Å | µ = 0.21 mm−1 |
c = 16.2411 (4) Å | T = 173 K |
β = 110.568 (1)° | Prism, colourless |
V = 1761.67 (8) Å3 | 0.3 × 0.2 × 0.1 mm |
Z = 4 |
Nonius KappaCCD with APEXII detector diffractometer | 2456 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 25°, θmin = 2.7° |
Detector resolution: 9 pixels mm-1 | h = −17→18 |
φ and ω scans | k = −9→8 |
5912 measured reflections | l = −19→19 |
3099 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.039 | w = 1/[σ2(Fo2) + (0.0296P)2 + 1.504P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.092 | (Δ/σ)max = 0.001 |
S = 1.05 | Δρmax = 0.22 e Å−3 |
3099 reflections | Δρmin = −0.27 e Å−3 |
253 parameters |
C16H19F5N2O4Si | V = 1761.67 (8) Å3 |
Mr = 426.42 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.2027 (4) Å | µ = 0.21 mm−1 |
b = 7.6207 (2) Å | T = 173 K |
c = 16.2411 (4) Å | 0.3 × 0.2 × 0.1 mm |
β = 110.568 (1)° |
Nonius KappaCCD with APEXII detector diffractometer | 2456 reflections with I > 2σ(I) |
5912 measured reflections | Rint = 0.031 |
3099 independent reflections |
R[F2 > 2σ(F2)] = 0.039 | 0 restraints |
wR(F2) = 0.092 | H-atom parameters constrained |
S = 1.05 | Δρmax = 0.22 e Å−3 |
3099 reflections | Δρmin = −0.27 e Å−3 |
253 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Si13 | 0.97532 (4) | 0.78594 (8) | 0.86902 (4) | 0.02310 (16) | |
F2 | 0.40578 (10) | 0.6889 (2) | 0.84279 (11) | 0.0522 (4) | |
F3 | 0.27692 (10) | 0.4350 (3) | 0.82441 (11) | 0.0594 (5) | |
F4 | 0.33118 (12) | 0.0976 (2) | 0.86283 (11) | 0.0614 (5) | |
F5 | 0.51698 (13) | 0.0127 (2) | 0.91677 (13) | 0.0692 (5) | |
F6 | 0.64535 (10) | 0.2641 (2) | 0.93287 (12) | 0.0594 (5) | |
O8 | 0.65323 (12) | 0.6813 (3) | 0.96762 (11) | 0.0464 (5) | |
O14 | 0.97348 (10) | 0.7809 (2) | 0.97124 (9) | 0.0269 (4) | |
O20 | 1.01580 (10) | 0.9657 (2) | 0.83334 (10) | 0.0269 (4) | |
O21 | 0.97836 (10) | 0.5987 (2) | 0.81759 (10) | 0.0312 (4) | |
N9 | 0.61017 (12) | 0.6639 (3) | 0.81880 (12) | 0.0278 (4) | |
H9 | 0.5708 | 0.6143 | 0.7712 | 0.033* | |
N17 | 1.12283 (12) | 0.7347 (3) | 0.93537 (12) | 0.0262 (4) | |
C1 | 0.52963 (15) | 0.4837 (3) | 0.88953 (14) | 0.0309 (6) | |
C2 | 0.43490 (16) | 0.5230 (4) | 0.86223 (15) | 0.0341 (6) | |
C3 | 0.36870 (16) | 0.3938 (4) | 0.85321 (16) | 0.0382 (6) | |
C4 | 0.39591 (18) | 0.2229 (4) | 0.87225 (17) | 0.0413 (7) | |
C5 | 0.48958 (19) | 0.1797 (4) | 0.89961 (18) | 0.0427 (7) | |
C6 | 0.55422 (16) | 0.3103 (4) | 0.90777 (16) | 0.0378 (6) | |
C7 | 0.60408 (16) | 0.6221 (3) | 0.89642 (15) | 0.0312 (6) | |
C10 | 0.67912 (15) | 0.7881 (3) | 0.80927 (15) | 0.0288 (5) | |
H10A | 0.679 | 0.8942 | 0.8444 | 0.035* | |
H10B | 0.6598 | 0.824 | 0.7468 | 0.035* | |
C11 | 0.77909 (14) | 0.7152 (3) | 0.83832 (15) | 0.0295 (5) | |
H11A | 0.8026 | 0.6978 | 0.9028 | 0.035* | |
H11B | 0.7778 | 0.5991 | 0.8105 | 0.035* | |
C12 | 0.84674 (14) | 0.8355 (3) | 0.81418 (14) | 0.0257 (5) | |
H12A | 0.8355 | 0.9576 | 0.8289 | 0.031* | |
H12B | 0.8313 | 0.8298 | 0.7497 | 0.031* | |
C15 | 1.05262 (14) | 0.7340 (3) | 1.04586 (14) | 0.0282 (5) | |
H15A | 1.0516 | 0.6064 | 1.0571 | 0.034* | |
H15B | 1.0509 | 0.7976 | 1.0984 | 0.034* | |
C16 | 1.14112 (15) | 0.7814 (3) | 1.02816 (14) | 0.0307 (5) | |
H16A | 1.1546 | 0.9083 | 1.0378 | 0.037* | |
H16B | 1.1955 | 0.7146 | 1.0675 | 0.037* | |
C18 | 1.17155 (16) | 0.8512 (3) | 0.89244 (16) | 0.0329 (6) | |
H18A | 1.1762 | 0.7947 | 0.8392 | 0.04* | |
H18B | 1.2357 | 0.8788 | 0.9332 | 0.04* | |
C19 | 1.11278 (15) | 1.0158 (3) | 0.86826 (16) | 0.0305 (5) | |
H19A | 1.1245 | 1.0904 | 0.9209 | 0.037* | |
H19B | 1.1295 | 1.0835 | 0.8239 | 0.037* | |
C22 | 1.06325 (17) | 0.5059 (3) | 0.83005 (16) | 0.0354 (6) | |
H22A | 1.0898 | 0.5422 | 0.7851 | 0.042* | |
H22B | 1.0507 | 0.3782 | 0.8239 | 0.042* | |
C23 | 1.13256 (16) | 0.5461 (3) | 0.92118 (16) | 0.0330 (6) | |
H23A | 1.1179 | 0.476 | 0.9661 | 0.04* | |
H23B | 1.1974 | 0.5186 | 0.9247 | 0.04* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Si13 | 0.0218 (3) | 0.0238 (3) | 0.0226 (3) | −0.0001 (3) | 0.0064 (2) | 0.0027 (3) |
F2 | 0.0415 (9) | 0.0471 (10) | 0.0674 (11) | 0.0108 (7) | 0.0183 (8) | 0.0011 (8) |
F3 | 0.0238 (7) | 0.0906 (14) | 0.0646 (11) | 0.0000 (8) | 0.0166 (7) | −0.0068 (10) |
F4 | 0.0566 (10) | 0.0715 (12) | 0.0621 (11) | −0.0332 (9) | 0.0283 (9) | −0.0114 (9) |
F5 | 0.0733 (12) | 0.0416 (11) | 0.0933 (14) | 0.0003 (9) | 0.0300 (11) | 0.0161 (10) |
F6 | 0.0306 (8) | 0.0621 (11) | 0.0797 (12) | 0.0107 (8) | 0.0122 (8) | 0.0202 (10) |
O8 | 0.0414 (10) | 0.0700 (14) | 0.0257 (9) | −0.0139 (10) | 0.0090 (8) | −0.0094 (9) |
O14 | 0.0209 (7) | 0.0371 (9) | 0.0214 (8) | 0.0006 (7) | 0.0059 (6) | 0.0031 (7) |
O20 | 0.0217 (8) | 0.0279 (9) | 0.0292 (8) | −0.0010 (7) | 0.0067 (6) | 0.0065 (7) |
O21 | 0.0299 (8) | 0.0278 (9) | 0.0337 (9) | 0.0019 (7) | 0.0085 (7) | −0.0015 (7) |
N9 | 0.0232 (9) | 0.0344 (11) | 0.0248 (10) | −0.0036 (8) | 0.0073 (8) | −0.0029 (9) |
N17 | 0.0219 (9) | 0.0316 (11) | 0.0248 (10) | 0.0022 (8) | 0.0080 (8) | 0.0058 (8) |
C1 | 0.0249 (11) | 0.0446 (16) | 0.0244 (12) | −0.0016 (11) | 0.0101 (10) | 0.0008 (11) |
C2 | 0.0314 (13) | 0.0432 (16) | 0.0301 (13) | 0.0017 (12) | 0.0139 (11) | −0.0016 (11) |
C3 | 0.0219 (12) | 0.0628 (19) | 0.0329 (13) | −0.0030 (12) | 0.0136 (10) | −0.0076 (13) |
C4 | 0.0407 (14) | 0.0518 (18) | 0.0383 (14) | −0.0169 (13) | 0.0227 (12) | −0.0063 (13) |
C5 | 0.0464 (15) | 0.0397 (17) | 0.0447 (15) | −0.0025 (13) | 0.0192 (13) | 0.0069 (13) |
C6 | 0.0263 (12) | 0.0483 (17) | 0.0379 (14) | 0.0043 (12) | 0.0099 (11) | 0.0086 (12) |
C7 | 0.0253 (11) | 0.0387 (15) | 0.0297 (13) | −0.0004 (11) | 0.0097 (10) | −0.0014 (11) |
C10 | 0.0245 (11) | 0.0292 (13) | 0.0311 (12) | −0.0036 (10) | 0.0078 (9) | −0.0005 (10) |
C11 | 0.0230 (11) | 0.0283 (13) | 0.0330 (13) | −0.0022 (10) | 0.0046 (10) | 0.0020 (11) |
C12 | 0.0232 (11) | 0.0281 (13) | 0.0241 (11) | −0.0019 (10) | 0.0062 (9) | 0.0007 (10) |
C15 | 0.0263 (11) | 0.0334 (14) | 0.0225 (11) | 0.0013 (10) | 0.0056 (9) | 0.0027 (10) |
C16 | 0.0233 (11) | 0.0390 (14) | 0.0258 (12) | −0.0007 (10) | 0.0038 (9) | 0.0037 (11) |
C18 | 0.0235 (11) | 0.0415 (15) | 0.0349 (13) | 0.0012 (11) | 0.0117 (10) | 0.0103 (12) |
C19 | 0.0232 (11) | 0.0335 (14) | 0.0337 (12) | −0.0057 (10) | 0.0087 (10) | 0.0045 (11) |
C22 | 0.0399 (13) | 0.0306 (14) | 0.0389 (14) | 0.0094 (11) | 0.0178 (11) | 0.0037 (11) |
C23 | 0.0317 (12) | 0.0338 (14) | 0.0364 (13) | 0.0110 (11) | 0.0158 (11) | 0.0091 (11) |
Si13—O21 | 1.6625 (17) | C4—C5 | 1.374 (4) |
Si13—O14 | 1.6706 (15) | C5—C6 | 1.372 (4) |
Si13—O20 | 1.6860 (16) | C10—C11 | 1.529 (3) |
Si13—C12 | 1.880 (2) | C10—H10A | 0.99 |
Si13—N17 | 2.1551 (18) | C10—H10B | 0.99 |
F2—C2 | 1.341 (3) | C11—C12 | 1.528 (3) |
F3—C3 | 1.344 (3) | C11—H11A | 0.99 |
F4—C4 | 1.341 (3) | C11—H11B | 0.99 |
F5—C5 | 1.338 (3) | C12—H12A | 0.99 |
F6—C6 | 1.346 (3) | C12—H12B | 0.99 |
O8—C7 | 1.221 (3) | C15—C16 | 1.515 (3) |
O14—C15 | 1.421 (2) | C15—H15A | 0.99 |
O20—C19 | 1.433 (2) | C15—H15B | 0.99 |
O21—C22 | 1.422 (3) | C16—H16A | 0.99 |
N9—C7 | 1.335 (3) | C16—H16B | 0.99 |
N9—C10 | 1.460 (3) | C18—C19 | 1.510 (3) |
N9—H9 | 0.88 | C18—H18A | 0.99 |
N17—C23 | 1.472 (3) | C18—H18B | 0.99 |
N17—C16 | 1.477 (3) | C19—H19A | 0.99 |
N17—C18 | 1.478 (3) | C19—H19B | 0.99 |
C1—C6 | 1.377 (4) | C22—C23 | 1.516 (3) |
C1—C2 | 1.383 (3) | C22—H22A | 0.99 |
C1—C7 | 1.522 (3) | C22—H22B | 0.99 |
C2—C3 | 1.378 (4) | C23—H23A | 0.99 |
C3—C4 | 1.368 (4) | C23—H23B | 0.99 |
O21—Si13—O14 | 119.51 (9) | C12—C11—C10 | 112.86 (19) |
O21—Si13—O20 | 116.55 (8) | C12—C11—H11A | 109 |
O14—Si13—O20 | 119.73 (8) | C10—C11—H11A | 109 |
O21—Si13—C12 | 98.18 (9) | C12—C11—H11B | 109 |
O14—Si13—C12 | 95.62 (8) | C10—C11—H11B | 109 |
O20—Si13—C12 | 96.79 (9) | H11A—C11—H11B | 107.8 |
O21—Si13—N17 | 83.57 (8) | C11—C12—Si13 | 116.06 (15) |
O14—Si13—N17 | 82.92 (7) | C11—C12—H12A | 108.3 |
O20—Si13—N17 | 82.97 (7) | Si13—C12—H12A | 108.3 |
C12—Si13—N17 | 178.12 (9) | C11—C12—H12B | 108.3 |
C15—O14—Si13 | 123.26 (13) | Si13—C12—H12B | 108.3 |
C19—O20—Si13 | 121.96 (14) | H12A—C12—H12B | 107.4 |
C22—O21—Si13 | 122.63 (15) | O14—C15—C16 | 108.70 (17) |
C7—N9—C10 | 123.05 (19) | O14—C15—H15A | 110 |
C7—N9—H9 | 118.5 | C16—C15—H15A | 110 |
C10—N9—H9 | 118.5 | O14—C15—H15B | 110 |
C23—N17—C16 | 113.68 (18) | C16—C15—H15B | 110 |
C23—N17—C18 | 114.70 (18) | H15A—C15—H15B | 108.3 |
C16—N17—C18 | 113.02 (19) | N17—C16—C15 | 105.95 (17) |
C23—N17—Si13 | 104.05 (14) | N17—C16—H16A | 110.5 |
C16—N17—Si13 | 104.87 (13) | C15—C16—H16A | 110.5 |
C18—N17—Si13 | 105.15 (13) | N17—C16—H16B | 110.5 |
C6—C1—C2 | 116.7 (2) | C15—C16—H16B | 110.5 |
C6—C1—C7 | 120.7 (2) | H16A—C16—H16B | 108.7 |
C2—C1—C7 | 122.5 (2) | N17—C18—C19 | 105.81 (17) |
F2—C2—C3 | 118.7 (2) | N17—C18—H18A | 110.6 |
F2—C2—C1 | 120.0 (2) | C19—C18—H18A | 110.6 |
C3—C2—C1 | 121.3 (2) | N17—C18—H18B | 110.6 |
F3—C3—C4 | 119.7 (2) | C19—C18—H18B | 110.6 |
F3—C3—C2 | 120.0 (3) | H18A—C18—H18B | 108.7 |
C4—C3—C2 | 120.3 (2) | O20—C19—C18 | 108.34 (19) |
F4—C4—C3 | 120.0 (2) | O20—C19—H19A | 110 |
F4—C4—C5 | 120.1 (3) | C18—C19—H19A | 110 |
C3—C4—C5 | 119.8 (2) | O20—C19—H19B | 110 |
F5—C5—C6 | 120.7 (2) | C18—C19—H19B | 110 |
F5—C5—C4 | 120.4 (2) | H19A—C19—H19B | 108.4 |
C6—C5—C4 | 118.9 (3) | O21—C22—C23 | 108.86 (19) |
F6—C6—C5 | 117.7 (2) | O21—C22—H22A | 109.9 |
F6—C6—C1 | 119.3 (2) | C23—C22—H22A | 109.9 |
C5—C6—C1 | 123.0 (2) | O21—C22—H22B | 109.9 |
O8—C7—N9 | 125.7 (2) | C23—C22—H22B | 109.9 |
O8—C7—C1 | 121.2 (2) | H22A—C22—H22B | 108.3 |
N9—C7—C1 | 113.11 (19) | N17—C23—C22 | 106.05 (19) |
N9—C10—C11 | 113.86 (19) | N17—C23—H23A | 110.5 |
N9—C10—H10A | 108.8 | C22—C23—H23A | 110.5 |
C11—C10—H10A | 108.8 | N17—C23—H23B | 110.5 |
N9—C10—H10B | 108.8 | C22—C23—H23B | 110.5 |
C11—C10—H10B | 108.8 | H23A—C23—H23B | 108.7 |
H10A—C10—H10B | 107.7 |
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O20i | 0.88 | 2.08 | 2.955 (2) | 172 |
C15—H15B···O20ii | 0.99 | 2.51 | 3.406 (3) | 150 |
C16—H16B···F6iii | 0.99 | 2.43 | 3.101 (3) | 125 |
C18—H18B···F6iii | 0.99 | 2.53 | 3.320 (3) | 136 |
C23—H23B···F3iv | 0.99 | 2.43 | 3.229 (3) | 137 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+2, −y+2, −z+2; (iii) −x+2, −y+1, −z+2; (iv) x+1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C16H19F5N2O4Si |
Mr | 426.42 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 15.2027 (4), 7.6207 (2), 16.2411 (4) |
β (°) | 110.568 (1) |
V (Å3) | 1761.67 (8) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.3 × 0.2 × 0.1 |
Data collection | |
Diffractometer | Nonius KappaCCD with APEXII detector |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5912, 3099, 2456 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.092, 1.05 |
No. of reflections | 3099 |
No. of parameters | 253 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.27 |
Computer programs: COLLECT (Nonius, 2004), DENZO and SCALEPACK (Otwinowski & Minor, 1997), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).
D—H···A | D—H | H···A | D···A | D—H···A |
N9—H9···O20i | 0.88 | 2.08 | 2.955 (2) | 172 |
C15—H15B···O20ii | 0.99 | 2.51 | 3.406 (3) | 150 |
C16—H16B···F6iii | 0.99 | 2.43 | 3.101 (3) | 125 |
C18—H18B···F6iii | 0.99 | 2.53 | 3.320 (3) | 136 |
C23—H23B···F3iv | 0.99 | 2.43 | 3.229 (3) | 137 |
Symmetry codes: (i) −x+3/2, y−1/2, −z+3/2; (ii) −x+2, −y+2, −z+2; (iii) −x+2, −y+1, −z+2; (iv) x+1, y, z. |
The title compound is a perfluorobenzamide derivative including a silatrane group (Fig. 1). A weak anion-π-type of interaction between the electron pair of the carbonyl oxygen O(8) and the two carbon atoms C(3) and C(4) of the perfluorobenzoic acid moiety creates a dimer. The interaction distances are 3.096 (3) and 3.036 (3) Å for the O(8)···C(3) and O(8)···C(4), respectively. Similar interaction but between the polarized iodine atoms in diiodotetrafluorobenzene and carbonyl oxygen has recently been observed in a study of halogen bonding (Russo et al., 2007). In addition a normal hydrogen bond, N···O = 2.954 (2) Å with angle of 172.45°, exists from the amide hydrogen to one of the silatrane O atoms, O(20). Also two short intermolecular contacts ranging from 3.027 to 3.406 Å between C—H and silatrane O atoms and three to the fluorine atoms, from 3.101 to 3.229 Å are observed.