Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801013046/cv6051sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801013046/cv6051Isup2.hkl |
CCDC reference: 172207
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.003 Å
- R factor = 0.054
- wR factor = 0.148
- Data-to-parameter ratio = 18.2
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
The treatment of Vilsmeir-Haack reagent (phosphoryl chloride/dimethylformamide) with benzosuberone produced the β-chlorovinylaldehyde as an oil. This product was treated with p-fluoroaniline (freshly distilled) to afford the corresponding anil derivative as red solids. After heating the anil derivative at 503–513 K for 5 min, the title compound, (I), was obtained. Single crystals suitable for X-ray structure determination were obtained by slow evaporation from a chloroform–petroleum ether solution.
After checking their presence in the difference map, all H atoms were geometrically fixed and allowed to ride on their attached atoms.
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
Fig. 1. The structure of title compound showing 50% probability displacement ellipsoids with the atom-numbering scheme. |
C18H14FN | F(000) = 552 |
Mr = 263.30 | Dx = 1.288 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
a = 8.4871 (2) Å | Cell parameters from 4222 reflections |
b = 10.0561 (2) Å | θ = 2.4–28.3° |
c = 16.0181 (1) Å | µ = 0.08 mm−1 |
β = 96.536 (1)° | T = 293 K |
V = 1358.21 (4) Å3 | Block, colourless |
Z = 4 | 0.48 × 0.44 × 0.28 mm |
Siemens SMART CCD area-detector diffractometer | 1784 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.071 |
Graphite monochromator | θmax = 28.3°, θmin = 2.4° |
Detector resolution: 8.33 pixels mm-1 | h = −6→11 |
ω scans | k = −13→10 |
9310 measured reflections | l = −19→20 |
3305 independent reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.054 | H-atom parameters constrained |
wR(F2) = 0.148 | w = 1/[σ2(Fo2) + (0.0688P)2] where P = (Fo2 + 2Fc2)/3 |
S = 0.90 | (Δ/σ)max < 0.001 |
3305 reflections | Δρmax = 0.28 e Å−3 |
182 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.046 (4) |
C18H14FN | V = 1358.21 (4) Å3 |
Mr = 263.30 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 8.4871 (2) Å | µ = 0.08 mm−1 |
b = 10.0561 (2) Å | T = 293 K |
c = 16.0181 (1) Å | 0.48 × 0.44 × 0.28 mm |
β = 96.536 (1)° |
Siemens SMART CCD area-detector diffractometer | 1784 reflections with I > 2σ(I) |
9310 measured reflections | Rint = 0.071 |
3305 independent reflections |
R[F2 > 2σ(F2)] = 0.054 | 0 restraints |
wR(F2) = 0.148 | H-atom parameters constrained |
S = 0.90 | Δρmax = 0.28 e Å−3 |
3305 reflections | Δρmin = −0.19 e Å−3 |
182 parameters |
Experimental. The data collection covered over a hemisphere of reciprocal space by a combination of three sets of exposures; each set had a different ϕ angle (0, 88 and 180°) for the crystal and each exposure of 10 s covered 0.3° in ω. The crystal-to-detector distance was 4 cm and the detector swing angle was -35°. Crystal decay was monitored by repeating fifty initial frames at the end of data collection and analysing the intensity of duplicate reflections, and was found to be negligible. |
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 wRand 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. andis not relevant to the choice of reflections for refinement. R-factorsbased on F2 are statistically about twice as large as those based on F, andR– factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.43909 (15) | 0.30774 (14) | 0.08522 (8) | 0.0431 (4) | |
F1 | −0.05440 (16) | 0.64353 (14) | 0.12711 (9) | 0.1028 (5) | |
C1 | 0.31395 (18) | 0.38900 (17) | 0.09694 (10) | 0.0415 (4) | |
C2 | 0.2918 (2) | 0.50699 (19) | 0.04944 (11) | 0.0529 (5) | |
H2A | 0.3610 | 0.5276 | 0.0103 | 0.064* | |
C3 | 0.1703 (2) | 0.5908 (2) | 0.06039 (13) | 0.0623 (5) | |
H3A | 0.1563 | 0.6690 | 0.0294 | 0.075* | |
C4 | 0.0676 (2) | 0.5579 (2) | 0.11849 (13) | 0.0633 (6) | |
C5 | 0.0823 (2) | 0.4478 (2) | 0.16631 (12) | 0.0599 (5) | |
H5A | 0.0112 | 0.4303 | 0.2050 | 0.072* | |
C6 | 0.20792 (18) | 0.35916 (18) | 0.15651 (10) | 0.0434 (4) | |
C7 | 0.23437 (19) | 0.24116 (18) | 0.20343 (10) | 0.0488 (4) | |
H7A | 0.1669 | 0.2190 | 0.2431 | 0.059* | |
C8 | 0.35752 (18) | 0.15893 (18) | 0.19145 (10) | 0.0448 (4) | |
C9 | 0.3929 (2) | 0.0348 (2) | 0.24297 (11) | 0.0581 (5) | |
H9A | 0.3300 | 0.0359 | 0.2899 | 0.070* | |
H9B | 0.5037 | 0.0358 | 0.2658 | 0.070* | |
C10 | 0.3588 (2) | −0.0935 (2) | 0.19359 (12) | 0.0633 (6) | |
H10A | 0.2453 | −0.1091 | 0.1864 | 0.076* | |
H10B | 0.4084 | −0.1671 | 0.2258 | 0.076* | |
C11 | 0.4192 (2) | −0.09067 (19) | 0.10699 (11) | 0.0546 (5) | |
H11A | 0.4251 | −0.1812 | 0.0867 | 0.066* | |
H11B | 0.3429 | −0.0433 | 0.0682 | 0.066* | |
C12 | 0.5794 (2) | −0.02609 (18) | 0.10638 (10) | 0.0459 (4) | |
C13 | 0.7114 (2) | −0.1009 (2) | 0.09205 (11) | 0.0565 (5) | |
H13A | 0.7012 | −0.1924 | 0.0849 | 0.068* | |
C14 | 0.8571 (2) | −0.0420 (2) | 0.08821 (12) | 0.0637 (6) | |
H14A | 0.9443 | −0.0939 | 0.0793 | 0.076* | |
C15 | 0.8736 (2) | 0.0940 (2) | 0.09765 (12) | 0.0612 (6) | |
H15A | 0.9717 | 0.1339 | 0.0949 | 0.073* | |
C16 | 0.7436 (2) | 0.1707 (2) | 0.11124 (11) | 0.0524 (5) | |
H16A | 0.7546 | 0.2623 | 0.1173 | 0.063* | |
C17 | 0.59613 (18) | 0.11180 (18) | 0.11594 (10) | 0.0436 (4) | |
C18 | 0.45825 (17) | 0.19700 (17) | 0.12975 (9) | 0.0406 (4) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0447 (8) | 0.0424 (9) | 0.0433 (8) | −0.0014 (6) | 0.0100 (6) | 0.0003 (6) |
F1 | 0.1134 (11) | 0.0875 (11) | 0.1180 (11) | 0.0544 (8) | 0.0588 (9) | 0.0191 (8) |
C1 | 0.0422 (9) | 0.0425 (10) | 0.0404 (9) | −0.0014 (7) | 0.0065 (7) | −0.0038 (7) |
C2 | 0.0567 (11) | 0.0495 (12) | 0.0555 (11) | 0.0034 (8) | 0.0189 (8) | 0.0040 (9) |
C3 | 0.0727 (13) | 0.0471 (12) | 0.0703 (13) | 0.0107 (9) | 0.0221 (10) | 0.0055 (9) |
C4 | 0.0693 (13) | 0.0565 (14) | 0.0682 (13) | 0.0229 (10) | 0.0253 (10) | −0.0016 (10) |
C5 | 0.0595 (12) | 0.0668 (15) | 0.0577 (12) | 0.0097 (9) | 0.0258 (9) | 0.0008 (10) |
C6 | 0.0441 (9) | 0.0461 (11) | 0.0412 (9) | −0.0010 (7) | 0.0101 (7) | −0.0042 (7) |
C7 | 0.0501 (10) | 0.0594 (12) | 0.0389 (9) | −0.0046 (8) | 0.0137 (7) | 0.0026 (8) |
C8 | 0.0469 (10) | 0.0524 (11) | 0.0349 (8) | −0.0026 (8) | 0.0036 (7) | 0.0014 (7) |
C9 | 0.0615 (12) | 0.0689 (14) | 0.0446 (10) | 0.0080 (10) | 0.0085 (8) | 0.0185 (9) |
C10 | 0.0665 (12) | 0.0562 (13) | 0.0676 (13) | 0.0016 (9) | 0.0097 (10) | 0.0257 (10) |
C11 | 0.0596 (11) | 0.0447 (11) | 0.0576 (11) | −0.0024 (8) | −0.0017 (9) | 0.0050 (8) |
C12 | 0.0519 (11) | 0.0483 (11) | 0.0361 (9) | 0.0063 (8) | −0.0010 (7) | 0.0064 (7) |
C13 | 0.0683 (12) | 0.0496 (12) | 0.0507 (11) | 0.0153 (9) | 0.0032 (9) | 0.0054 (8) |
C14 | 0.0555 (12) | 0.0746 (16) | 0.0610 (13) | 0.0232 (10) | 0.0065 (9) | 0.0056 (11) |
C15 | 0.0429 (10) | 0.0796 (16) | 0.0608 (12) | 0.0039 (9) | 0.0045 (9) | 0.0002 (10) |
C16 | 0.0501 (11) | 0.0566 (12) | 0.0504 (11) | −0.0027 (8) | 0.0055 (8) | −0.0024 (8) |
C17 | 0.0442 (9) | 0.0496 (11) | 0.0364 (9) | 0.0033 (7) | 0.0015 (7) | 0.0008 (7) |
C18 | 0.0391 (9) | 0.0462 (11) | 0.0360 (8) | −0.0024 (7) | 0.0026 (7) | −0.0014 (7) |
N1—C18 | 1.323 (2) | C9—H9B | 0.9700 |
N1—C1 | 1.370 (2) | C10—C11 | 1.533 (3) |
F1—C4 | 1.366 (2) | C10—H10A | 0.9700 |
C1—C2 | 1.411 (2) | C10—H10B | 0.9700 |
C1—C6 | 1.416 (2) | C11—C12 | 1.508 (2) |
C2—C3 | 1.358 (3) | C11—H11A | 0.9700 |
C2—H2A | 0.9300 | C11—H11B | 0.9700 |
C3—C4 | 1.385 (3) | C12—C13 | 1.389 (2) |
C3—H3A | 0.9300 | C12—C17 | 1.400 (2) |
C4—C5 | 1.344 (3) | C13—C14 | 1.379 (3) |
C5—C6 | 1.412 (2) | C13—H13A | 0.9300 |
C5—H5A | 0.9300 | C14—C15 | 1.381 (3) |
C6—C7 | 1.409 (2) | C14—H14A | 0.9300 |
C7—C8 | 1.363 (2) | C15—C16 | 1.384 (2) |
C7—H7A | 0.9300 | C15—H15A | 0.9300 |
C8—C18 | 1.431 (2) | C16—C17 | 1.394 (2) |
C8—C9 | 1.507 (2) | C16—H16A | 0.9300 |
C9—C10 | 1.524 (3) | C17—C18 | 1.487 (2) |
C9—H9A | 0.9700 | ||
C18—N1—C1 | 118.55 (13) | C9—C10—H10A | 109.0 |
N1—C1—C2 | 119.06 (14) | C11—C10—H10A | 109.0 |
N1—C1—C6 | 121.87 (15) | C9—C10—H10B | 109.0 |
C2—C1—C6 | 119.06 (15) | C11—C10—H10B | 109.0 |
C3—C2—C1 | 120.58 (16) | H10A—C10—H10B | 107.8 |
C3—C2—H2A | 119.7 | C12—C11—C10 | 114.12 (15) |
C1—C2—H2A | 119.7 | C12—C11—H11A | 108.7 |
C2—C3—C4 | 118.89 (19) | C10—C11—H11A | 108.7 |
C2—C3—H3A | 120.6 | C12—C11—H11B | 108.7 |
C4—C3—H3A | 120.6 | C10—C11—H11B | 108.7 |
C5—C4—F1 | 118.93 (16) | H11A—C11—H11B | 107.6 |
C5—C4—C3 | 123.73 (17) | C13—C12—C17 | 118.71 (16) |
F1—C4—C3 | 117.34 (18) | C13—C12—C11 | 120.82 (18) |
C4—C5—C6 | 118.59 (16) | C17—C12—C11 | 120.39 (15) |
C4—C5—H5A | 120.7 | C14—C13—C12 | 121.26 (19) |
C6—C5—H5A | 120.7 | C14—C13—H13A | 119.4 |
C7—C6—C5 | 123.28 (15) | C12—C13—H13A | 119.4 |
C7—C6—C1 | 117.58 (15) | C13—C14—C15 | 120.03 (17) |
C5—C6—C1 | 119.14 (16) | C13—C14—H14A | 120.0 |
C8—C7—C6 | 120.92 (14) | C15—C14—H14A | 120.0 |
C8—C7—H7A | 119.5 | C14—C15—C16 | 119.75 (17) |
C6—C7—H7A | 119.5 | C14—C15—H15A | 120.1 |
C7—C8—C18 | 117.58 (16) | C16—C15—H15A | 120.1 |
C7—C8—C9 | 122.21 (15) | C15—C16—C17 | 120.58 (18) |
C18—C8—C9 | 120.16 (15) | C15—C16—H16A | 119.7 |
C8—C9—C10 | 113.76 (14) | C17—C16—H16A | 119.7 |
C8—C9—H9A | 108.8 | C16—C17—C12 | 119.66 (15) |
C10—C9—H9A | 108.8 | C16—C17—C18 | 119.32 (16) |
C8—C9—H9B | 108.8 | C12—C17—C18 | 121.01 (14) |
C10—C9—H9B | 108.8 | N1—C18—C8 | 123.47 (14) |
H9A—C9—H9B | 107.7 | N1—C18—C17 | 117.09 (13) |
C9—C10—C11 | 112.99 (15) | C8—C18—C17 | 119.40 (15) |
C18—N1—C1—C2 | −179.63 (15) | C10—C11—C12—C13 | 111.62 (18) |
C18—N1—C1—C6 | 1.6 (2) | C10—C11—C12—C17 | −71.7 (2) |
N1—C1—C2—C3 | −179.02 (17) | C17—C12—C13—C14 | 0.8 (2) |
C6—C1—C2—C3 | −0.2 (3) | C11—C12—C13—C14 | 177.52 (16) |
C1—C2—C3—C4 | −0.6 (3) | C12—C13—C14—C15 | −0.8 (3) |
C2—C3—C4—C5 | 1.1 (3) | C13—C14—C15—C16 | 0.2 (3) |
C2—C3—C4—F1 | −179.18 (19) | C14—C15—C16—C17 | 0.3 (3) |
F1—C4—C5—C6 | 179.46 (17) | C15—C16—C17—C12 | −0.3 (2) |
C3—C4—C5—C6 | −0.8 (3) | C15—C16—C17—C18 | −179.40 (16) |
C4—C5—C6—C7 | 179.89 (18) | C13—C12—C17—C16 | −0.2 (2) |
C4—C5—C6—C1 | 0.0 (3) | C11—C12—C17—C16 | −176.97 (14) |
N1—C1—C6—C7 | −0.6 (2) | C13—C12—C17—C18 | 178.82 (14) |
C2—C1—C6—C7 | −179.42 (16) | C11—C12—C17—C18 | 2.1 (2) |
N1—C1—C6—C5 | 179.26 (15) | C1—N1—C18—C8 | −1.8 (2) |
C2—C1—C6—C5 | 0.5 (2) | C1—N1—C18—C17 | −179.48 (13) |
C5—C6—C7—C8 | 179.95 (17) | C7—C8—C18—N1 | 1.0 (2) |
C1—C6—C7—C8 | −0.2 (2) | C9—C8—C18—N1 | −176.58 (15) |
C6—C7—C8—C18 | 0.0 (2) | C7—C8—C18—C17 | 178.66 (15) |
C6—C7—C8—C9 | 177.53 (16) | C9—C8—C18—C17 | 1.1 (2) |
C7—C8—C9—C10 | 110.31 (19) | C16—C17—C18—N1 | 44.5 (2) |
C18—C8—C9—C10 | −72.2 (2) | C12—C17—C18—N1 | −134.56 (16) |
C8—C9—C10—C11 | 44.4 (2) | C16—C17—C18—C8 | −133.33 (17) |
C9—C10—C11—C12 | 40.5 (2) | C12—C17—C18—C8 | 47.6 (2) |
Experimental details
Crystal data | |
Chemical formula | C18H14FN |
Mr | 263.30 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 293 |
a, b, c (Å) | 8.4871 (2), 10.0561 (2), 16.0181 (1) |
β (°) | 96.536 (1) |
V (Å3) | 1358.21 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.48 × 0.44 × 0.28 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 9310, 3305, 1784 |
Rint | 0.071 |
(sin θ/λ)max (Å−1) | 0.667 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.054, 0.148, 0.90 |
No. of reflections | 3305 |
No. of parameters | 182 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.19 |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 1990).
N1—C18 | 1.323 (2) | C5—C6 | 1.412 (2) |
N1—C1 | 1.370 (2) | C6—C7 | 1.409 (2) |
F1—C4 | 1.366 (2) | C7—C8 | 1.363 (2) |
C1—C2 | 1.411 (2) | C8—C18 | 1.431 (2) |
C1—C6 | 1.416 (2) | C8—C9 | 1.507 (2) |
C2—C3 | 1.358 (3) | C12—C17 | 1.400 (2) |
C3—C4 | 1.385 (3) | C17—C18 | 1.487 (2) |
C4—C5 | 1.344 (3) | ||
C18—N1—C1 | 118.55 (13) | C9—C10—C11 | 112.99 (15) |
C2—C1—C6 | 119.06 (15) | C16—C17—C12 | 119.66 (15) |
C5—C4—F1 | 118.93 (16) | C12—C17—C18 | 121.01 (14) |
C8—C7—C6 | 120.92 (14) | C8—C18—C17 | 119.40 (15) |
C18—C8—C9 | 120.16 (15) | ||
C11—C12—C13—C14 | 177.52 (16) | C16—C17—C18—N1 | 44.5 (2) |
C9—C8—C18—N1 | −176.58 (15) | C12—C17—C18—N1 | −134.56 (16) |
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Polycyclic aromatic hydrocarbons (PAHs) are well known enviromental pollutants (Dong et al., 1977; Harvey, 1991) and have been intensively investigated in carcinogenic studies (Harvey, 1991). Interestingly, the introduction of one F atom at a particular position has a significant effect on the carcinogenic activity of the PAHs (Harvey & Cortez, 1997; Zajc, 1999). Pan et al. (2001) focus on the synthesis, characterization and bioactivity of fluoro-polycyclic azaarenes (PAAs) in order to extend the carcinogenic studies, and have isolated the title compound, (I). An X-ray structure determination of (I) was undertaken to establish the conformation of the structure.
In compound (I), the bond lengths and angles show normal values and agree with those observed in a chloro-derivative of the same structure (Ray et al., 1998). The cycloheptane ring adopts a half-chair conformation with a twofold axis through the C10 atom and bisecting the C17—C18 bond.
This is confirmed by its puckering parameters (Cremer & Pople, 1975) Q2 = 1.032 (2) Å, ϕ2 = 65.4 (1)°, Q3 = 0.122 (2) Å, ϕ3 = 324.4 (9)° and QT = 1.039 (2) Å. In the quinoline ring, the C2—C3, C4—C5 and C7—C8 bond distances are slightly shorter due to their localized double-bond character, while the N1—C5 bond shows partial double-bond character (Allen et al., 1987). The quinoline and benzene rings are essentially planar to within ±0.007 (2) Å and to within ±0.005 (2) Å, respectively, while atom F1 deviates slightly from the quinoline plane by -0.018 (1) Å. The quinoline and benzene ring planes make a dihedral angle of 46.3 (1)°.