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In the title compound {systematic name:
N-[3-(5-aza-2,8,9-trioxa-1-silabicyclo[3.3.3]undecan-1-yl)propyl]pentafluorobenzamide}, C
16H
19F
5N
2O
4Si, unexpected weak anion
π-type C=O
C(aromatic) interactions form a dimer [O
C distances of 3.096 (3) and 3.036 (3) Å]. These dimers are further connected by a normal N—H
O hydrogen bond [2.955 (2) Å], from the amide H atom to one of the silatrane O atoms. Also, four intermolecular contacts between CH groups and silatrane O and F atoms [3.101(3)–3.406 (3) Å] are observed.
Supporting information
CCDC reference: 663805
Key indicators
- Single-crystal X-ray study
- T = 173 K
- R factor = 0.039
- wR factor = 0.092
- Data-to-parameter ratio = 12.2
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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).
Structure description
top
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).
N-[3-(5-aza-2,8,9-trioxa-1-silabicyclo[3.3.3]undecan-1-yl)propyl]
pentafluorobenzamide
top
Crystal data top
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 | |
Data collection top
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 top
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 | |
Crystal data top
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)° | |
Data collection top
Nonius KappaCCD with APEXII detector diffractometer | 2456 reflections with I > 2σ(I) |
5912 measured reflections | Rint = 0.031 |
3099 independent reflections | |
Refinement top
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 | |
Special details top
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | 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* | |
Atomic displacement parameters (Å2) top | 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) |
Geometric parameters (Å, º) top
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 | | |
Hydrogen-bond geometry (Å, º) top
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 |
Hydrogen-bond geometry (Å, º) top
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. |
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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.