The title compound, C7H3F2N, packs with slightly puckered molecular sheets [molecules tilted by 8.1 (1)° with respect to the sheets]. Two of the H atoms in the molecule are in contact with N atoms in adjacent molecules, while the remaining H atom is in contact with two F atoms in adjacent molecules.
Supporting information
CCDC reference: 193741
Key indicators
- Single-crystal X-ray study
- T = 172 K
- Mean (C-C) = 0.002 Å
- R factor = 0.041
- wR factor = 0.120
- Data-to-parameter ratio = 13.3
checkCIF results
No syntax errors found
ADDSYM reports no extra symmetry
Alert Level C:
PLAT_371 Alert C Long C(sp2)-C(sp1) Bond C(1) - C(7) = 1.45 Ang.
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: TEXSAN (Molecular Structure Corporation, 1985); program(s) used to solve structure: MITHRIL (Gilmore, 1984) and DIRDIF (Buerskens, 1984); program(s) used to refine structure: SHELXTL (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
3,5-Difluorobenzonitrile
top
Crystal data top
C7H3F2N | Dx = 1.506 Mg m−3 |
Mr = 139.10 | Melting point = 357–359 K |
Monoclinic, P21/m | Mo Kα radiation, λ = 0.71073 Å |
a = 3.730 (4) Å | Cell parameters from 24 reflections |
b = 7.486 (4) Å | θ = 22–27° |
c = 11.019 (5) Å | µ = 0.13 mm−1 |
β = 94.34 (7)° | T = 172 K |
V = 306.8 (4) Å3 | Prism, colorless |
Z = 2 | 0.50 × 0.35 × 0.30 mm |
F(000) = 140 | |
Data collection top
Enraf-Nonius CAD-4 diffractometer | Rint = 0.056 |
Radiation source: fine-focus sealed tube | θmax = 27.9°, θmin = 1.9° |
Graphite monochromator | h = −4→4 |
ω–2θ scans | k = −9→9 |
2908 measured reflections | l = −14→14 |
784 independent reflections | 3 standard reflections every 70 min min |
654 reflections with I > 2σ(I) | intensity decay: 1% |
Refinement top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.120 | All H-atom parameters refined |
S = 1.06 | w = 1/[σ2(Fo2) + (0.066P)2 + 0.057P] where P = (Fo2 + 2Fc2)/3 |
784 reflections | (Δ/σ)max = 0.001 |
59 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.19 e Å−3 |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
F3 | 0.2916 (3) | 0.56191 (11) | 0.11214 (8) | 0.0441 (3) | |
N1 | 0.9543 (5) | 0.2500 | 0.55650 (14) | 0.0388 (4) | |
C1 | 0.6306 (4) | 0.2500 | 0.34033 (14) | 0.0239 (4) | |
C2 | 0.5478 (3) | 0.41278 (15) | 0.28415 (11) | 0.0270 (3) | |
H2 | 0.601 (4) | 0.527 (2) | 0.3219 (14) | 0.034 (4)* | |
C3 | 0.3767 (3) | 0.40645 (15) | 0.16851 (11) | 0.0275 (3) | |
C4 | 0.2893 (4) | 0.2500 | 0.10805 (15) | 0.0272 (4) | |
H4 | 0.180 (7) | 0.2500 | 0.031 (2) | 0.042 (6)* | |
C7 | 0.8123 (5) | 0.2500 | 0.46135 (15) | 0.0292 (4) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
F3 | 0.0590 (7) | 0.0279 (5) | 0.0434 (5) | 0.0066 (4) | −0.0080 (4) | 0.0089 (3) |
N1 | 0.0366 (9) | 0.0485 (10) | 0.0302 (8) | 0.000 | −0.0043 (6) | 0.000 |
C1 | 0.0175 (7) | 0.0313 (8) | 0.0228 (7) | 0.000 | 0.0014 (5) | 0.000 |
C2 | 0.0260 (7) | 0.0259 (6) | 0.0290 (6) | −0.0010 (4) | 0.0018 (4) | −0.0035 (4) |
C3 | 0.0267 (6) | 0.0260 (6) | 0.0297 (6) | 0.0028 (5) | 0.0015 (4) | 0.0038 (4) |
C4 | 0.0241 (9) | 0.0328 (9) | 0.0242 (8) | 0.000 | −0.0012 (6) | 0.000 |
C7 | 0.0241 (8) | 0.0355 (9) | 0.0282 (8) | 0.000 | 0.0021 (6) | 0.000 |
Geometric parameters (Å, º) top
F3—C3 | 1.3458 (14) | C2—C3 | 1.3820 (19) |
N1—C7 | 1.138 (2) | C2—H2 | 0.967 (18) |
C1—C2i | 1.3910 (15) | C3—C4 | 1.3744 (15) |
C1—C2 | 1.3910 (15) | C4—C3i | 1.3744 (15) |
C1—C7 | 1.449 (2) | C4—H4 | 0.92 (2) |
| | | |
C2i—C1—C2 | 122.35 (15) | F3—C3—C2 | 118.17 (11) |
C2i—C1—C7 | 118.83 (8) | C4—C3—C2 | 123.52 (11) |
C2—C1—C7 | 118.83 (8) | C3—C4—C3i | 116.89 (15) |
C3—C2—C1 | 116.86 (11) | C3—C4—H4 | 121.55 (8) |
C3—C2—H2 | 119.5 (10) | C3i—C4—H4 | 121.56 (8) |
C1—C2—H2 | 123.6 (10) | N1—C7—C1 | 179.85 (18) |
F3—C3—C4 | 118.31 (12) | | |
Symmetry code: (i) x, −y+1/2, z. |
Distances and angles (Å, °) in the C—H···X—C contacts topH | X | C—H | C—H···X | H···X | H···X═C | C···X |
H2 | N1i | 0.97 | 151 | 2.65 | 134 | 3.523 (2) |
H4 | F3ii | 0.92 | 141 | 2.67 | 148 | 3.431 (3) |
H4 | F3iii | 0.92 | 141 | 2.67 | 148 | 3.431 (3) |
Symmetry codes: (i) 2-x, 1-y, 1-z; (ii) -x, 1-y, -z; (iii) -x, -1/2+y, -z. |