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In the title compound, C13H8Cl2FN, the central C=N bond length is 1.2699 (18) Å and the bond length between the C atom of the aromatic ring and the C atom of the imine group is 1.4644 (19) Å. This arrangement corresponds to a conjugated C=N moiety.
Supporting information
CCDC reference: 285519
Key indicators
- Single-crystal X-ray study
- T = 298 K
- Mean (C-C)= 0.002 Å
- R factor = 0.037
- wR factor = 0.106
- Data-to-parameter ratio = 18.2
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997a); molecular graphics: SHELXTL (Sheldrick, 1997b); software used to prepare material for publication: SHELXTL.
3,5-Dichloro-
N-(4-fluorobenzylidene)aniline
top
Crystal data top
C13H8Cl2FN | F(000) = 544 |
Mr = 268.10 | Dx = 1.491 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2ybc | Cell parameters from 1023 reflections |
a = 14.1311 (7) Å | θ = 4.4–28.6° |
b = 3.8481 (2) Å | µ = 0.53 mm−1 |
c = 22.0365 (11) Å | T = 298 K |
β = 94.752 (1)° | Block, white |
V = 1194.18 (10) Å3 | 0.60 × 0.47 × 0.39 mm |
Z = 4 | |
Data collection top
Bruker SMART CCD area-detector diffractometer | 2863 independent reflections |
Radiation source: fine-focus sealed tube | 2506 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.017 |
φ and ω scans | θmax = 28.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −18→18 |
Tmin = 0.742, Tmax = 0.820 | k = −5→5 |
13224 measured reflections | l = −28→29 |
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)] = 0.037 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.106 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0573P)2 + 0.3432P] where P = (Fo2 + 2Fc2)/3 |
2863 reflections | (Δ/σ)max = 0.001 |
157 parameters | Δρmax = 0.38 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
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. |
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 (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 0.32754 (4) | −0.35584 (17) | 0.999714 (18) | 0.07205 (18) | |
Cl2 | 0.58696 (3) | −0.00790 (14) | 0.84603 (2) | 0.06158 (16) | |
F1 | −0.05438 (8) | 0.3787 (4) | 0.55361 (5) | 0.0776 (4) | |
N1 | 0.22726 (9) | 0.1260 (4) | 0.78919 (5) | 0.0457 (3) | |
C1 | 0.15786 (9) | 0.1598 (4) | 0.68603 (6) | 0.0380 (3) | |
C2 | 0.07465 (10) | 0.3226 (4) | 0.70090 (6) | 0.0408 (3) | |
H2 | 0.0674 | 0.3824 | 0.7411 | 0.049* | |
C3 | 0.00291 (10) | 0.3957 (5) | 0.65631 (7) | 0.0468 (3) | |
H3 | −0.0530 | 0.5016 | 0.6660 | 0.056* | |
C4 | 0.01643 (11) | 0.3078 (5) | 0.59714 (7) | 0.0504 (4) | |
C5 | 0.09772 (12) | 0.1545 (5) | 0.58017 (7) | 0.0533 (4) | |
H5 | 0.1050 | 0.1028 | 0.5396 | 0.064* | |
C6 | 0.16859 (11) | 0.0790 (4) | 0.62542 (7) | 0.0462 (3) | |
H6 | 0.2242 | −0.0272 | 0.6152 | 0.055* | |
C7 | 0.23260 (10) | 0.0630 (4) | 0.73301 (6) | 0.0402 (3) | |
H7 | 0.2847 (13) | −0.053 (5) | 0.7189 (8) | 0.048* | |
C8 | 0.30393 (10) | 0.0247 (4) | 0.83091 (6) | 0.0417 (3) | |
C9 | 0.39851 (10) | 0.0545 (4) | 0.81808 (6) | 0.0415 (3) | |
H9 | 0.4141 | 0.1402 | 0.7807 | 0.050* | |
C10 | 0.46860 (10) | −0.0459 (4) | 0.86194 (7) | 0.0418 (3) | |
C11 | 0.44932 (11) | −0.1733 (4) | 0.91805 (6) | 0.0453 (3) | |
H11 | 0.4977 | −0.2401 | 0.9469 | 0.054* | |
C12 | 0.35492 (11) | −0.1972 (4) | 0.92943 (6) | 0.0470 (3) | |
C13 | 0.28228 (11) | −0.0973 (5) | 0.88757 (6) | 0.0489 (4) | |
H13 | 0.2195 | −0.1112 | 0.8970 | 0.059* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0739 (3) | 0.1035 (4) | 0.0390 (2) | −0.0008 (3) | 0.00640 (19) | 0.0221 (2) |
Cl2 | 0.0396 (2) | 0.0847 (3) | 0.0603 (3) | −0.00487 (19) | 0.00354 (17) | −0.0023 (2) |
F1 | 0.0566 (6) | 0.1277 (11) | 0.0454 (5) | 0.0139 (7) | −0.0145 (4) | 0.0047 (6) |
N1 | 0.0408 (6) | 0.0591 (8) | 0.0367 (6) | 0.0074 (6) | 0.0005 (5) | 0.0040 (5) |
C1 | 0.0377 (6) | 0.0424 (7) | 0.0336 (6) | −0.0014 (5) | 0.0016 (5) | 0.0020 (5) |
C2 | 0.0409 (7) | 0.0484 (8) | 0.0335 (6) | 0.0012 (6) | 0.0042 (5) | 0.0007 (6) |
C3 | 0.0386 (7) | 0.0581 (9) | 0.0433 (7) | 0.0047 (6) | 0.0022 (6) | 0.0018 (6) |
C4 | 0.0427 (7) | 0.0685 (10) | 0.0384 (7) | −0.0007 (7) | −0.0063 (6) | 0.0047 (7) |
C5 | 0.0535 (8) | 0.0744 (11) | 0.0320 (6) | 0.0023 (8) | 0.0025 (6) | −0.0040 (7) |
C6 | 0.0428 (7) | 0.0585 (9) | 0.0380 (7) | 0.0041 (7) | 0.0063 (6) | −0.0021 (6) |
C7 | 0.0373 (6) | 0.0447 (7) | 0.0385 (7) | 0.0028 (6) | 0.0026 (5) | 0.0023 (6) |
C8 | 0.0418 (7) | 0.0486 (8) | 0.0341 (6) | 0.0055 (6) | 0.0000 (5) | 0.0016 (6) |
C9 | 0.0441 (7) | 0.0457 (8) | 0.0345 (6) | 0.0001 (6) | 0.0022 (5) | 0.0022 (6) |
C10 | 0.0386 (6) | 0.0445 (7) | 0.0420 (7) | −0.0005 (6) | 0.0011 (5) | −0.0032 (6) |
C11 | 0.0459 (7) | 0.0505 (8) | 0.0381 (7) | 0.0038 (6) | −0.0057 (6) | 0.0017 (6) |
C12 | 0.0524 (8) | 0.0560 (9) | 0.0326 (6) | 0.0012 (7) | 0.0034 (6) | 0.0061 (6) |
C13 | 0.0413 (7) | 0.0681 (10) | 0.0373 (7) | 0.0022 (7) | 0.0042 (6) | 0.0047 (7) |
Geometric parameters (Å, º) top
Cl1—C12 | 1.7379 (15) | C5—C6 | 1.384 (2) |
Cl2—C10 | 1.7432 (15) | C5—H5 | 0.9300 |
F1—C4 | 1.3552 (17) | C6—H6 | 0.9300 |
N1—C7 | 1.2699 (18) | C7—H7 | 0.936 (18) |
N1—C8 | 1.4164 (17) | C8—C13 | 1.392 (2) |
C1—C6 | 1.3918 (19) | C8—C9 | 1.393 (2) |
C1—C2 | 1.3952 (19) | C9—C10 | 1.380 (2) |
C1—C7 | 1.4644 (19) | C9—H9 | 0.9300 |
C2—C3 | 1.3809 (19) | C10—C11 | 1.378 (2) |
C2—H2 | 0.9300 | C11—C12 | 1.381 (2) |
C3—C4 | 1.376 (2) | C11—H11 | 0.9300 |
C3—H3 | 0.9300 | C12—C13 | 1.377 (2) |
C4—C5 | 1.371 (2) | C13—H13 | 0.9300 |
| | | |
C7—N1—C8 | 118.44 (12) | N1—C7—H7 | 121.8 (10) |
C6—C1—C2 | 119.12 (13) | C1—C7—H7 | 115.3 (10) |
C6—C1—C7 | 119.48 (13) | C13—C8—C9 | 119.72 (13) |
C2—C1—C7 | 121.38 (12) | C13—C8—N1 | 117.52 (13) |
C3—C2—C1 | 120.51 (13) | C9—C8—N1 | 122.72 (13) |
C3—C2—H2 | 119.7 | C10—C9—C8 | 118.65 (13) |
C1—C2—H2 | 119.7 | C10—C9—H9 | 120.7 |
C4—C3—C2 | 118.22 (14) | C8—C9—H9 | 120.7 |
C4—C3—H3 | 120.9 | C11—C10—C9 | 122.96 (14) |
C2—C3—H3 | 120.9 | C11—C10—Cl2 | 118.33 (11) |
F1—C4—C5 | 118.69 (14) | C9—C10—Cl2 | 118.71 (11) |
F1—C4—C3 | 117.96 (14) | C10—C11—C12 | 116.90 (13) |
C5—C4—C3 | 123.35 (13) | C10—C11—H11 | 121.6 |
C4—C5—C6 | 117.81 (13) | C12—C11—H11 | 121.6 |
C4—C5—H5 | 121.1 | C13—C12—C11 | 122.53 (13) |
C6—C5—H5 | 121.1 | C13—C12—Cl1 | 119.11 (12) |
C5—C6—C1 | 120.97 (14) | C11—C12—Cl1 | 118.36 (11) |
C5—C6—H6 | 119.5 | C12—C13—C8 | 119.22 (14) |
C1—C6—H6 | 119.5 | C12—C13—H13 | 120.4 |
N1—C7—C1 | 122.89 (13) | C8—C13—H13 | 120.4 |
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