The title compound, 7-chloro-8-fluoro-4-phenyl-2,3,3a,4,5,9b-hexahydrofuro[3,2-c]quinoline, C17H15ClFNO, was obtained from the imine Diels-Alder reaction of an N-benzylideneaniline and 2,3-dihydrofuran catalyzed by ZrCl4. An isomer that crystallizes in the centrosymmetric monoclinic space group C2/c is presented. The furan ring is in a twist conformation, while the pyridine ring is in a sofa conformation. An intermolecular hydrogen bond between the pyridine NH group and the O atom of the furan ring in a neighboring molecule forms chains along the b axis.
Supporting information
CCDC reference: 262461
Key indicators
- Single-crystal X-ray study
- T = 273 K
- Mean (C-C) = 0.005 Å
- R factor = 0.066
- wR factor = 0.154
- Data-to-parameter ratio = 13.7
checkCIF/PLATON results
No syntax errors found
Alert level C
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem
0 ALERT level B = Potentially serious problem
1 ALERT level C = Check and explain
0 ALERT level G = General alerts; check
0 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
0 ALERT type 2 Indicator that the structure model may be wrong or deficient
1 ALERT type 3 Indicator that the structure quality may be low
0 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997; molecular graphics: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).
7-chloro-8-fluoro-4-phenyl-2,3,3a,4,5,9 b-hexahydrofuro[3,2-
c]quinoline
top
Crystal data top
C17H15ClFNO | F(000) = 1264 |
Mr = 303.75 | Dx = 1.36 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -C 2yc | Cell parameters from 5098 reflections |
a = 25.826 (2) Å | θ = 2.4–21.2° |
b = 6.8065 (6) Å | µ = 0.27 mm−1 |
c = 17.2924 (16) Å | T = 273 K |
β = 102.490 (2)° | Needle, colorless |
V = 2967.8 (4) Å3 | 0.20 × 0.15 × 0.10 mm |
Z = 8 | |
Data collection top
Bruker SMART APEX CCD area-detector diffractometer | 2074 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.028 |
Graphite monochromator | θmax = 25°, θmin = 1.6° |
ω scans | h = −28→30 |
7178 measured reflections | k = −8→7 |
2607 independent reflections | l = −20→20 |
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)] = 0.066 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.155 | H-atom parameters constrained |
S = 1.16 | w = 1/[σ2(Fo2) + (0.0698P)2 + 1.7065P] where P = (Fo2 + 2Fc2)/3 |
2607 reflections | (Δ/σ)max = 0.001 |
190 parameters | Δρmax = 0.39 e Å−3 |
0 restraints | Δρmin = −0.28 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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
Cl1 | 1.10033 (3) | 1.16166 (14) | 0.11297 (5) | 0.0598 (3) | |
F1 | 1.09269 (8) | 0.7454 (3) | 0.06877 (14) | 0.0773 (7) | |
O1 | 0.92619 (9) | 0.4753 (3) | 0.14844 (14) | 0.0592 (6) | |
C1 | 1.04737 (12) | 0.8173 (5) | 0.08544 (17) | 0.0465 (8) | |
C2 | 1.00440 (12) | 0.6981 (4) | 0.08050 (17) | 0.0452 (8) | |
H2 | 1.0068 | 0.5665 | 0.0673 | 0.054* | |
C3 | 0.95731 (11) | 0.7700 (4) | 0.09486 (16) | 0.0370 (7) | |
C4 | 0.91125 (12) | 0.6314 (4) | 0.09259 (18) | 0.0433 (7) | |
H4 | 0.9001 | 0.5763 | 0.0392 | 0.052* | |
C5 | 0.92008 (15) | 0.5521 (5) | 0.2226 (2) | 0.0652 (10) | |
H5A | 0.952 | 0.6209 | 0.2487 | 0.078* | |
H5B | 0.9134 | 0.4466 | 0.2569 | 0.078* | |
C6 | 0.87390 (16) | 0.6907 (5) | 0.2056 (2) | 0.0624 (10) | |
H6A | 0.8824 | 0.8121 | 0.2351 | 0.075* | |
H6B | 0.843 | 0.6319 | 0.2198 | 0.075* | |
C7 | 0.86375 (12) | 0.7288 (4) | 0.11668 (19) | 0.0452 (8) | |
H7 | 0.8314 | 0.6594 | 0.0908 | 0.054* | |
C8 | 0.85844 (11) | 0.9461 (4) | 0.09243 (17) | 0.0416 (7) | |
H8 | 0.8544 | 0.9529 | 0.0348 | 0.05* | |
C9 | 0.95417 (11) | 0.9682 (4) | 0.11496 (16) | 0.0380 (7) | |
C10 | 0.99884 (12) | 1.0862 (4) | 0.12160 (17) | 0.0422 (7) | |
H10 | 0.9974 | 1.2171 | 0.1364 | 0.051* | |
C11 | 1.04508 (11) | 1.0120 (5) | 0.10660 (16) | 0.0416 (7) | |
C12 | 0.81072 (12) | 1.0436 (4) | 0.11298 (18) | 0.0438 (7) | |
C13 | 0.76210 (14) | 1.0271 (6) | 0.0618 (2) | 0.0700 (11) | |
H13 | 0.7592 | 0.9564 | 0.0151 | 0.084* | |
C14 | 0.71789 (15) | 1.1131 (7) | 0.0786 (3) | 0.0875 (14) | |
H14 | 0.6854 | 1.0992 | 0.0432 | 0.105* | |
C15 | 0.72060 (15) | 1.2190 (6) | 0.1465 (3) | 0.0766 (12) | |
H15 | 0.6905 | 1.2783 | 0.1573 | 0.092* | |
C16 | 0.76855 (16) | 1.2361 (6) | 0.1984 (3) | 0.0737 (11) | |
H16 | 0.7711 | 1.3068 | 0.2451 | 0.088* | |
C17 | 0.81330 (13) | 1.1489 (5) | 0.1818 (2) | 0.0601 (9) | |
H17 | 0.8456 | 1.1616 | 0.2177 | 0.072* | |
N1 | 0.90741 (9) | 1.0447 (3) | 0.12859 (16) | 0.0465 (7) | |
H1 | 0.9074 | 1.1474 | 0.1576 | 0.056* | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
Cl1 | 0.0391 (5) | 0.0809 (7) | 0.0615 (5) | −0.0120 (4) | 0.0154 (4) | −0.0080 (5) |
F1 | 0.0442 (12) | 0.0899 (16) | 0.1043 (16) | 0.0166 (11) | 0.0303 (11) | −0.0222 (13) |
O1 | 0.0702 (16) | 0.0276 (11) | 0.0843 (17) | 0.0056 (11) | 0.0269 (13) | 0.0054 (11) |
C1 | 0.0362 (17) | 0.058 (2) | 0.0466 (17) | 0.0152 (16) | 0.0123 (13) | −0.0055 (15) |
C2 | 0.050 (2) | 0.0384 (17) | 0.0495 (18) | 0.0122 (15) | 0.0164 (14) | −0.0092 (14) |
C3 | 0.0425 (17) | 0.0327 (15) | 0.0364 (15) | 0.0045 (13) | 0.0101 (12) | −0.0004 (12) |
C4 | 0.0482 (18) | 0.0337 (16) | 0.0490 (17) | −0.0009 (14) | 0.0127 (14) | −0.0085 (13) |
C5 | 0.075 (3) | 0.058 (2) | 0.066 (2) | −0.003 (2) | 0.0217 (19) | 0.0156 (19) |
C6 | 0.083 (3) | 0.0421 (19) | 0.072 (2) | 0.0027 (18) | 0.039 (2) | 0.0046 (17) |
C7 | 0.0413 (18) | 0.0359 (16) | 0.0601 (19) | −0.0065 (13) | 0.0144 (14) | −0.0104 (14) |
C8 | 0.0370 (17) | 0.0418 (17) | 0.0474 (16) | 0.0027 (13) | 0.0126 (13) | −0.0031 (14) |
C9 | 0.0378 (17) | 0.0314 (15) | 0.0463 (16) | 0.0064 (13) | 0.0121 (13) | 0.0029 (12) |
C10 | 0.0444 (18) | 0.0319 (15) | 0.0518 (18) | 0.0013 (14) | 0.0139 (14) | −0.0009 (13) |
C11 | 0.0333 (16) | 0.0551 (19) | 0.0360 (15) | 0.0017 (14) | 0.0068 (12) | 0.0016 (13) |
C12 | 0.0391 (18) | 0.0383 (17) | 0.0574 (18) | 0.0063 (14) | 0.0179 (14) | 0.0055 (14) |
C13 | 0.039 (2) | 0.090 (3) | 0.077 (2) | 0.0123 (19) | 0.0043 (18) | −0.014 (2) |
C14 | 0.040 (2) | 0.118 (4) | 0.100 (3) | 0.018 (2) | 0.005 (2) | −0.010 (3) |
C15 | 0.044 (2) | 0.083 (3) | 0.111 (3) | 0.017 (2) | 0.034 (2) | 0.004 (3) |
C16 | 0.066 (3) | 0.078 (3) | 0.087 (3) | 0.008 (2) | 0.037 (2) | −0.020 (2) |
C17 | 0.0398 (19) | 0.071 (2) | 0.072 (2) | 0.0021 (17) | 0.0158 (16) | −0.0138 (19) |
N1 | 0.0399 (15) | 0.0278 (13) | 0.0766 (18) | 0.0021 (11) | 0.0233 (13) | −0.0091 (12) |
Geometric parameters (Å, º) top
Cl1—C11 | 1.737 (3) | C8—C12 | 1.508 (4) |
F1—C1 | 1.356 (3) | C8—H8 | 0.98 |
O1—C5 | 1.425 (4) | N1—C8 | 1.449 (4) |
O1—C4 | 1.431 (4) | N1—C9 | 1.381 (3) |
C1—C2 | 1.362 (4) | C9—C10 | 1.390 (4) |
C1—C11 | 1.380 (4) | C10—C11 | 1.372 (4) |
C2—C3 | 1.382 (4) | C10—H10 | 0.93 |
C2—H2 | 0.93 | C12—C13 | 1.375 (4) |
C3—C9 | 1.400 (4) | C12—C17 | 1.379 (4) |
C3—C4 | 1.512 (4) | C13—C14 | 1.369 (5) |
C4—C7 | 1.529 (4) | C13—H13 | 0.93 |
C4—H4 | 0.98 | C14—C15 | 1.367 (6) |
C5—C6 | 1.499 (5) | C14—H14 | 0.93 |
C5—H5A | 0.97 | C15—C16 | 1.368 (6) |
C5—H5B | 0.97 | C15—H15 | 0.93 |
C6—C7 | 1.526 (4) | C16—C17 | 1.383 (5) |
C6—H6A | 0.97 | C16—H16 | 0.93 |
C6—H6B | 0.97 | C17—H17 | 0.93 |
C7—C8 | 1.535 (4) | N1—H1 | 0.86 |
C7—H7 | 0.98 | | |
| | | |
C5—O1—C4 | 105.6 (2) | N1—C8—C7 | 108.1 (2) |
F1—C1—C2 | 120.1 (3) | C12—C8—C7 | 112.9 (2) |
F1—C1—C11 | 119.4 (3) | N1—C8—H8 | 107.9 |
C2—C1—C11 | 120.5 (3) | C12—C8—H8 | 107.9 |
C1—C2—C3 | 121.0 (3) | C7—C8—H8 | 107.9 |
C1—C2—H2 | 119.5 | N1—C9—C10 | 120.6 (3) |
C3—C2—H2 | 119.5 | N1—C9—C3 | 120.4 (3) |
C2—C3—C9 | 119.1 (3) | C10—C9—C3 | 119.1 (3) |
C2—C3—C4 | 119.5 (3) | C11—C10—C9 | 120.8 (3) |
C9—C3—C4 | 121.3 (3) | C11—C10—H10 | 119.6 |
O1—C4—C3 | 110.5 (2) | C9—C10—H10 | 119.6 |
O1—C4—C7 | 104.7 (2) | C10—C11—C1 | 119.5 (3) |
C3—C4—C7 | 113.3 (2) | C10—C11—Cl1 | 120.6 (2) |
O1—C4—H4 | 109.4 | C1—C11—Cl1 | 119.9 (2) |
C3—C4—H4 | 109.4 | C13—C12—C17 | 117.7 (3) |
C7—C4—H4 | 109.4 | C13—C12—C8 | 119.4 (3) |
O1—C5—C6 | 107.0 (3) | C17—C12—C8 | 122.9 (3) |
O1—C5—H5A | 110.3 | C14—C13—C12 | 121.1 (4) |
C6—C5—H5A | 110.3 | C14—C13—H13 | 119.5 |
O1—C5—H5B | 110.3 | C12—C13—H13 | 119.5 |
C6—C5—H5B | 110.3 | C15—C14—C13 | 121.2 (4) |
H5A—C5—H5B | 108.6 | C15—C14—H14 | 119.4 |
C5—C6—C7 | 105.1 (3) | C13—C14—H14 | 119.4 |
C5—C6—H6A | 110.7 | C14—C15—C16 | 118.6 (4) |
C7—C6—H6A | 110.7 | C14—C15—H15 | 120.7 |
C5—C6—H6B | 110.7 | C16—C15—H15 | 120.7 |
C7—C6—H6B | 110.7 | C15—C16—C17 | 120.4 (4) |
H6A—C6—H6B | 108.8 | C15—C16—H16 | 119.8 |
C6—C7—C4 | 103.2 (3) | C17—C16—H16 | 119.8 |
C6—C7—C8 | 115.1 (2) | C12—C17—C16 | 121.0 (3) |
C4—C7—C8 | 111.9 (2) | C12—C17—H17 | 119.5 |
C6—C7—H7 | 108.8 | C16—C17—H17 | 119.5 |
C4—C7—H7 | 108.8 | C9—N1—C8 | 117.7 (2) |
C8—C7—H7 | 108.8 | C9—N1—H1 | 121.1 |
N1—C8—C12 | 112.1 (2) | C8—N1—H1 | 121.1 |
| | | |
F1—C1—C2—C3 | −178.0 (3) | C4—C3—C9—C10 | 175.5 (3) |
C11—C1—C2—C3 | 1.4 (5) | N1—C9—C10—C11 | −178.7 (3) |
C1—C2—C3—C9 | −0.2 (4) | C3—C9—C10—C11 | 1.8 (4) |
C1—C2—C3—C4 | −177.1 (3) | C9—C10—C11—C1 | −0.6 (4) |
C5—O1—C4—C3 | 83.2 (3) | C9—C10—C11—Cl1 | 178.6 (2) |
C5—O1—C4—C7 | −39.0 (3) | F1—C1—C11—C10 | 178.4 (3) |
C2—C3—C4—O1 | 57.9 (3) | C2—C1—C11—C10 | −1.0 (4) |
C9—C3—C4—O1 | −119.0 (3) | F1—C1—C11—Cl1 | −0.9 (4) |
C2—C3—C4—C7 | 175.0 (3) | C2—C1—C11—Cl1 | 179.8 (2) |
C9—C3—C4—C7 | −1.9 (4) | N1—C8—C12—C13 | 153.3 (3) |
C4—O1—C5—C6 | 33.9 (3) | C7—C8—C12—C13 | −84.4 (4) |
O1—C5—C6—C7 | −14.7 (4) | N1—C8—C12—C17 | −27.2 (4) |
C5—C6—C7—C4 | −8.5 (3) | C7—C8—C12—C17 | 95.1 (4) |
C5—C6—C7—C8 | −130.6 (3) | C17—C12—C13—C14 | 0.3 (6) |
O1—C4—C7—C6 | 28.7 (3) | C8—C12—C13—C14 | 179.8 (4) |
C3—C4—C7—C6 | −91.7 (3) | C12—C13—C14—C15 | 0.3 (7) |
O1—C4—C7—C8 | 153.0 (2) | C13—C14—C15—C16 | −0.7 (7) |
C3—C4—C7—C8 | 32.6 (3) | C14—C15—C16—C17 | 0.5 (7) |
C6—C7—C8—N1 | 59.9 (3) | C13—C12—C17—C16 | −0.5 (5) |
C4—C7—C8—N1 | −57.5 (3) | C8—C12—C17—C16 | 180.0 (3) |
C6—C7—C8—C12 | −64.7 (3) | C15—C16—C17—C12 | 0.1 (6) |
C4—C7—C8—C12 | 178.0 (2) | C10—C9—N1—C8 | 156.4 (3) |
C2—C3—C9—N1 | 179.1 (3) | C3—C9—N1—C8 | −24.2 (4) |
C4—C3—C9—N1 | −4.0 (4) | C12—C8—N1—C9 | 179.3 (2) |
C2—C3—C9—C10 | −1.4 (4) | C7—C8—N1—C9 | 54.3 (3) |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.86 | 2.30 | 2.979 (3) | 136 |
C10—H10···O1i | 0.93 | 2.58 | 3.336 (4) | 138 |
C6—H6A···N1 | 0.97 | 2.61 | 2.971 (4) | 102 |
Symmetry code: (i) x, y+1, z. |