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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

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804032283/rz6028sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804032283/rz6028Isup2.hkl
Contains datablock I

CCDC reference: 262461

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](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

Computing details top

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
C17H15ClFNOF(000) = 1264
Mr = 303.75Dx = 1.36 Mg m3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 5098 reflections
a = 25.826 (2) Åθ = 2.4–21.2°
b = 6.8065 (6) ŵ = 0.27 mm1
c = 17.2924 (16) ÅT = 273 K
β = 102.490 (2)°Needle, colorless
V = 2967.8 (4) Å30.20 × 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 tubeRint = 0.028
Graphite monochromatorθmax = 25°, θmin = 1.6°
ω scansh = 2830
7178 measured reflectionsk = 87
2607 independent reflectionsl = 2020
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.066Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.155H-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 parametersΔρmax = 0.39 e Å3
0 restraintsΔρmin = 0.28 e Å3
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
xyzUiso*/Ueq
Cl11.10033 (3)1.16166 (14)0.11297 (5)0.0598 (3)
F11.09269 (8)0.7454 (3)0.06877 (14)0.0773 (7)
O10.92619 (9)0.4753 (3)0.14844 (14)0.0592 (6)
C11.04737 (12)0.8173 (5)0.08544 (17)0.0465 (8)
C21.00440 (12)0.6981 (4)0.08050 (17)0.0452 (8)
H21.00680.56650.06730.054*
C30.95731 (11)0.7700 (4)0.09486 (16)0.0370 (7)
C40.91125 (12)0.6314 (4)0.09259 (18)0.0433 (7)
H40.90010.57630.03920.052*
C50.92008 (15)0.5521 (5)0.2226 (2)0.0652 (10)
H5A0.9520.62090.24870.078*
H5B0.91340.44660.25690.078*
C60.87390 (16)0.6907 (5)0.2056 (2)0.0624 (10)
H6A0.88240.81210.23510.075*
H6B0.8430.63190.21980.075*
C70.86375 (12)0.7288 (4)0.11668 (19)0.0452 (8)
H70.83140.65940.09080.054*
C80.85844 (11)0.9461 (4)0.09243 (17)0.0416 (7)
H80.85440.95290.03480.05*
C90.95417 (11)0.9682 (4)0.11496 (16)0.0380 (7)
C100.99884 (12)1.0862 (4)0.12160 (17)0.0422 (7)
H100.99741.21710.13640.051*
C111.04508 (11)1.0120 (5)0.10660 (16)0.0416 (7)
C120.81072 (12)1.0436 (4)0.11298 (18)0.0438 (7)
C130.76210 (14)1.0271 (6)0.0618 (2)0.0700 (11)
H130.75920.95640.01510.084*
C140.71789 (15)1.1131 (7)0.0786 (3)0.0875 (14)
H140.68541.09920.04320.105*
C150.72060 (15)1.2190 (6)0.1465 (3)0.0766 (12)
H150.69051.27830.15730.092*
C160.76855 (16)1.2361 (6)0.1984 (3)0.0737 (11)
H160.77111.30680.24510.088*
C170.81330 (13)1.1489 (5)0.1818 (2)0.0601 (9)
H170.84561.16160.21770.072*
N10.90741 (9)1.0447 (3)0.12859 (16)0.0465 (7)
H10.90741.14740.15760.056*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0391 (5)0.0809 (7)0.0615 (5)0.0120 (4)0.0154 (4)0.0080 (5)
F10.0442 (12)0.0899 (16)0.1043 (16)0.0166 (11)0.0303 (11)0.0222 (13)
O10.0702 (16)0.0276 (11)0.0843 (17)0.0056 (11)0.0269 (13)0.0054 (11)
C10.0362 (17)0.058 (2)0.0466 (17)0.0152 (16)0.0123 (13)0.0055 (15)
C20.050 (2)0.0384 (17)0.0495 (18)0.0122 (15)0.0164 (14)0.0092 (14)
C30.0425 (17)0.0327 (15)0.0364 (15)0.0045 (13)0.0101 (12)0.0004 (12)
C40.0482 (18)0.0337 (16)0.0490 (17)0.0009 (14)0.0127 (14)0.0085 (13)
C50.075 (3)0.058 (2)0.066 (2)0.003 (2)0.0217 (19)0.0156 (19)
C60.083 (3)0.0421 (19)0.072 (2)0.0027 (18)0.039 (2)0.0046 (17)
C70.0413 (18)0.0359 (16)0.0601 (19)0.0065 (13)0.0144 (14)0.0104 (14)
C80.0370 (17)0.0418 (17)0.0474 (16)0.0027 (13)0.0126 (13)0.0031 (14)
C90.0378 (17)0.0314 (15)0.0463 (16)0.0064 (13)0.0121 (13)0.0029 (12)
C100.0444 (18)0.0319 (15)0.0518 (18)0.0013 (14)0.0139 (14)0.0009 (13)
C110.0333 (16)0.0551 (19)0.0360 (15)0.0017 (14)0.0068 (12)0.0016 (13)
C120.0391 (18)0.0383 (17)0.0574 (18)0.0063 (14)0.0179 (14)0.0055 (14)
C130.039 (2)0.090 (3)0.077 (2)0.0123 (19)0.0043 (18)0.014 (2)
C140.040 (2)0.118 (4)0.100 (3)0.018 (2)0.005 (2)0.010 (3)
C150.044 (2)0.083 (3)0.111 (3)0.017 (2)0.034 (2)0.004 (3)
C160.066 (3)0.078 (3)0.087 (3)0.008 (2)0.037 (2)0.020 (2)
C170.0398 (19)0.071 (2)0.072 (2)0.0021 (17)0.0158 (16)0.0138 (19)
N10.0399 (15)0.0278 (13)0.0766 (18)0.0021 (11)0.0233 (13)0.0091 (12)
Geometric parameters (Å, º) top
Cl1—C111.737 (3)C8—C121.508 (4)
F1—C11.356 (3)C8—H80.98
O1—C51.425 (4)N1—C81.449 (4)
O1—C41.431 (4)N1—C91.381 (3)
C1—C21.362 (4)C9—C101.390 (4)
C1—C111.380 (4)C10—C111.372 (4)
C2—C31.382 (4)C10—H100.93
C2—H20.93C12—C131.375 (4)
C3—C91.400 (4)C12—C171.379 (4)
C3—C41.512 (4)C13—C141.369 (5)
C4—C71.529 (4)C13—H130.93
C4—H40.98C14—C151.367 (6)
C5—C61.499 (5)C14—H140.93
C5—H5A0.97C15—C161.368 (6)
C5—H5B0.97C15—H150.93
C6—C71.526 (4)C16—C171.383 (5)
C6—H6A0.97C16—H160.93
C6—H6B0.97C17—H170.93
C7—C81.535 (4)N1—H10.86
C7—H70.98
C5—O1—C4105.6 (2)N1—C8—C7108.1 (2)
F1—C1—C2120.1 (3)C12—C8—C7112.9 (2)
F1—C1—C11119.4 (3)N1—C8—H8107.9
C2—C1—C11120.5 (3)C12—C8—H8107.9
C1—C2—C3121.0 (3)C7—C8—H8107.9
C1—C2—H2119.5N1—C9—C10120.6 (3)
C3—C2—H2119.5N1—C9—C3120.4 (3)
C2—C3—C9119.1 (3)C10—C9—C3119.1 (3)
C2—C3—C4119.5 (3)C11—C10—C9120.8 (3)
C9—C3—C4121.3 (3)C11—C10—H10119.6
O1—C4—C3110.5 (2)C9—C10—H10119.6
O1—C4—C7104.7 (2)C10—C11—C1119.5 (3)
C3—C4—C7113.3 (2)C10—C11—Cl1120.6 (2)
O1—C4—H4109.4C1—C11—Cl1119.9 (2)
C3—C4—H4109.4C13—C12—C17117.7 (3)
C7—C4—H4109.4C13—C12—C8119.4 (3)
O1—C5—C6107.0 (3)C17—C12—C8122.9 (3)
O1—C5—H5A110.3C14—C13—C12121.1 (4)
C6—C5—H5A110.3C14—C13—H13119.5
O1—C5—H5B110.3C12—C13—H13119.5
C6—C5—H5B110.3C15—C14—C13121.2 (4)
H5A—C5—H5B108.6C15—C14—H14119.4
C5—C6—C7105.1 (3)C13—C14—H14119.4
C5—C6—H6A110.7C14—C15—C16118.6 (4)
C7—C6—H6A110.7C14—C15—H15120.7
C5—C6—H6B110.7C16—C15—H15120.7
C7—C6—H6B110.7C15—C16—C17120.4 (4)
H6A—C6—H6B108.8C15—C16—H16119.8
C6—C7—C4103.2 (3)C17—C16—H16119.8
C6—C7—C8115.1 (2)C12—C17—C16121.0 (3)
C4—C7—C8111.9 (2)C12—C17—H17119.5
C6—C7—H7108.8C16—C17—H17119.5
C4—C7—H7108.8C9—N1—C8117.7 (2)
C8—C7—H7108.8C9—N1—H1121.1
N1—C8—C12112.1 (2)C8—N1—H1121.1
F1—C1—C2—C3178.0 (3)C4—C3—C9—C10175.5 (3)
C11—C1—C2—C31.4 (5)N1—C9—C10—C11178.7 (3)
C1—C2—C3—C90.2 (4)C3—C9—C10—C111.8 (4)
C1—C2—C3—C4177.1 (3)C9—C10—C11—C10.6 (4)
C5—O1—C4—C383.2 (3)C9—C10—C11—Cl1178.6 (2)
C5—O1—C4—C739.0 (3)F1—C1—C11—C10178.4 (3)
C2—C3—C4—O157.9 (3)C2—C1—C11—C101.0 (4)
C9—C3—C4—O1119.0 (3)F1—C1—C11—Cl10.9 (4)
C2—C3—C4—C7175.0 (3)C2—C1—C11—Cl1179.8 (2)
C9—C3—C4—C71.9 (4)N1—C8—C12—C13153.3 (3)
C4—O1—C5—C633.9 (3)C7—C8—C12—C1384.4 (4)
O1—C5—C6—C714.7 (4)N1—C8—C12—C1727.2 (4)
C5—C6—C7—C48.5 (3)C7—C8—C12—C1795.1 (4)
C5—C6—C7—C8130.6 (3)C17—C12—C13—C140.3 (6)
O1—C4—C7—C628.7 (3)C8—C12—C13—C14179.8 (4)
C3—C4—C7—C691.7 (3)C12—C13—C14—C150.3 (7)
O1—C4—C7—C8153.0 (2)C13—C14—C15—C160.7 (7)
C3—C4—C7—C832.6 (3)C14—C15—C16—C170.5 (7)
C6—C7—C8—N159.9 (3)C13—C12—C17—C160.5 (5)
C4—C7—C8—N157.5 (3)C8—C12—C17—C16180.0 (3)
C6—C7—C8—C1264.7 (3)C15—C16—C17—C120.1 (6)
C4—C7—C8—C12178.0 (2)C10—C9—N1—C8156.4 (3)
C2—C3—C9—N1179.1 (3)C3—C9—N1—C824.2 (4)
C4—C3—C9—N14.0 (4)C12—C8—N1—C9179.3 (2)
C2—C3—C9—C101.4 (4)C7—C8—N1—C954.3 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O1i0.862.302.979 (3)136
C10—H10···O1i0.932.583.336 (4)138
C6—H6A···N10.972.612.971 (4)102
Symmetry code: (i) x, y+1, z.
 

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