Buy article online - an online subscription or single-article purchase is required to access this article.
Download citation
Download citation
link to html
8-Chloro-9-fluoro-5-phen­yl-3,4,4a,5,6,10b-hexa­hydro-2H-pyrano[3,2-c]quinoline and 10-chloro-9-fluoro-5-phen­yl-3,4,4a,5,6,10b-hexa­hydro-2H-pyrano­[3,2-c]quinoline, both C18H17ClFNO, are diastereo­isomers, formed as the result of the imino Diels-Alder reactions of N-benzyl­ideneanilines with 3,4-dihydro-2H-pyran. The crystal structures reveal the stereochemistry of the pyran ring, which is endo/exo to the quinoline ring system formed in the cyclo­addition step. In both structures, the pyran ring adopts a chair conformation, while the nitrogen-containing heterocyclic ring prefers a half-chair conformation. The structures differ essentially in the relative orientation of the ring junction H atoms.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105006542/sk1815sup1.cif
Contains datablocks global, I, II

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105006542/sk1815Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105006542/sk1815IIsup3.hkl
Contains datablock II

CCDC references: 273032; 273033

Comment top

The pyranoquinoline moiety is commonly found in many alkaloids, viz. findersine, oricine and verprisine, and derivatives of these alkaloids possess a significant range of biological activities, such as anti-allergic, psychotropic and anti-inflammatory activities (Yamada et al., 1992; Faber et al., 1984; Nesterova et al., 1995). In addition, pyranoquinoline derivatives are used as potential pharmaceuticals (Mohamed, 1994). It is therefore not surprising that efforts are ongoing for synthesis of these compounds by different methods (Ma et al., 1999, Mahesh, Makesh & Perumal, 2004; Mahesh, Venkateswar Reddy et al., 2004). The Diels–Alder reaction catalysed by Lewis acids between N-benzylideneanilines and nucleophilic olefins is one of the powerful synthetic tools for constructing nitrogen-containing six-membered heterocyclic compounds. In this context, we have been examining a variety of conditions to achieve different product distributions. Recently, we described the synthesis and characterization of di-substituted pyrano and furano quinolines, by application of the imino Diels–Alder reaction using ZrCl4 as a potential green catalyst. The individual diastereoisomers thus obtained differ according to the stereochemistry (cis/trans) of the ring junction H atoms and the orientation (endo/exo) of the pyran ring. To elucidate the reaction stereochemistry and the molecular geometry of the structures, we have undertaken structural investigations of the title compounds, (I) and (II).

Both (I) and (II) crystallize in space group P1, with two independent molecules in the asymmetric unit. The geometries of the two independent molecules are very similar as far as interatomic distances and angles are concerned, the greatest differences being 0.008 Å [N1—C4 in (I)] and 0.030 Å [C16—C17 in (II)], and 1.8° [C4—N1—C5 in (I)] and 1.3° [C16—C17—C18 in (II)].

The geometric parameters of the two structures (Figs. 1 and 2) are not very different from the values found in the literature for other quinoline derivatives. More relevant differences between the structures are observed in the torsion angles, as a result of both the different configuration at the C6 ring junction and the different packing of the crystals. One significant difference is the orientation of atoms H5 and H6. The H5—C5—C6—H6 torsion angle, of −62.8 and −61.4° in (I), indicates a cis arrangement and is in accordance with the coupling constant J = 5.2 Hz. Consequently, the structure of (II), with a corresponding torsion angle of −173.5 and −173.8° showing a larger coupling constant, J = 10.8 Hz, is in a trans configuration.

In both the structures, the substitutions of the quinoline ring system produce a considerable twist about the C5···C11 vector. The twist can be seen from the C5—C6—C10—C11 and C5—N1—C4—C11 torsion angles of 48.5 (2)/51.1 (2) and −21.7 (3)/-16.4 (3)° in (I), and −51.0 (3)/-51.0 (3) and 14.5 (4)/13.5 (4)° in (II), respectively. In addition, these values indicate the fusion strain exerted during the ring formation in the Diels–Alder cycloaddition process.

It is interesting to note that in both structures the pyran ring is almost perpendicular to the quinoline ring system. In (I), atom O1 is displaced below the N1/C4/C11/C10 least-squares plane by −0.744 (2) Å in molecule 1 and above this plane by 0.694 (2) Å in molecule 2. Similarly, the corresponding displacements of atom O1 in (II) is −1.335 (2) and −1.335 (2) Å, respectively. The relative configuration/orientation of the quinoline ring system and the pyran ring can be seen from the C5—C6—C10—O1 torsion angle [175.4 (2) and 177.7 (2)° trans (exo) for (I), and 69.6 (3) and 69.7 (3)° cis (endo) for (II)].

The most appropriate puckering description for the pyridine ring is half-chair in both the structures, with an asymmetry parameter (Nardelli, 1983) ΔC2(C4—C11) of 0.005 (1) and 0.043 (1) in (I), and 0.034 (1) and 0.038 (1) in (II). The conformation of the pyran ring in both the structures is a chair as expected, with atoms C6, C8, C9 and C10 defining the plane, atoms C7 and O1 being displaced by −0.626 (3)/-0.637 (2) and 0.592 (2)/0.602 (2) Å in (I), and by 0.621 (3)/0.622 (3) and −0.679 (2)/-0.670 (2) Å in (II), respectively. The phenyl ring substituted at atom C5 is rotated through the C5—C13 bond, the N1—C5—C13—C14 torsion angles being −21.8 (3) and −23.9 (3)° in (I), and 50.4 (4) and 53.6 (4)° in (II), perhaps to facilitate the cis/trans orientation for the H atoms at C5. The dihedral angles between the planes of the halogen-substituted phenyl ring and the C5-phenyl ring are 44.5 (1) and 44.6 (1)° in (I), and 68.4 (1) and 71.0 (1)° in (II), respectively.

A striking feature is observed in the crystal packing of the two compounds. Interesting C—H···A contacts [A = Cl, F, O and N] are listed in Table 2. In (I), the N atom of the quinoline ring system is involved in intermolecular hydrogen-bond formation with the O atom of the pyran ring, in both the molecules present in the asymmetric unit (Fig. 3). Unusually, in (II), this conventional N—H···O hydrogen bond is not observed, even though good hydrogen-bonding functionalities are present. A similar feature has been noted in the structures of alloxan (Beyer et al., 2001; Coombes et al., 1997) and furoquinoline (Ravikumar et al., 2004). This complements the views of Desiraju (2002): `Hydrogen bonds are ubiquitous, directional and strong, and they do control the crystal packing rather effectively, but in the rarest of cases they can be absent. After all, any way to minimize the free energy of a crystal is a respectable way, and given that crystal structures are being determined in the numbers that they are, even axioms will be bypassed on occasion.'

Experimental top

To a solution of the appropriate N-benzylideneaniline (5.5 mmol) in dichloromethane (5 ml) at room temperature were added ZrCl4 (10 mol%) and 3-dihydropyran (5.5 mmol), and the mixture was stirred for 90 min. The completed reaction was quenched with water, and the crude product was purified by column chromatography using 2% ethylacetate and hexane, yielding the title compounds. Crystals for X-ray study were obtained by recrystallization from a mixture of methanol and water (3:1).

Refinement top

The H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93 (aromatic), 0.98 Å (CH) and 0.97 Å (CH2), a N—H distances of 0.90 Å, and Uiso(H) values of 1.2Ueq(C,N). The data coverage is 100% of all independent reflections to 2θ = 50° (a d-spacing of 0.841 Å); close examination revealed that missing reflections [12 and 20 reflections for (I) and (II), respectively] lie only in high angle (2θ > 45°) regions.

Computing details top

For both compounds, 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: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

Figures top
[Figure 1] Fig. 1. A view of the molecule of (I), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A view of the molecule of (II), with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 3] Fig. 3. A packing diagram for (I), highlighting N—H···O intermolecular hydrogen bonds (dashed lines) forming molecular columns along the a axis. H atoms not involved in the interactions shown have been omitted for clarity.
(I) 8-chloro-9-fluoro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline top
Crystal data top
C18H17ClFNOZ = 4
Mr = 317.78F(000) = 664
Triclinic, P1Dx = 1.358 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 10.5399 (7) ÅCell parameters from 4707 reflections
b = 11.2005 (7) Åθ = 2.4–26.2°
c = 13.4950 (9) ŵ = 0.26 mm1
α = 82.597 (1)°T = 273 K
β = 83.890 (1)°Needle, colorless
γ = 80.884 (1)°0.19 × 0.11 × 0.09 mm
V = 1553.85 (18) Å3
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
4629 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.026
Graphite monochromatorθmax = 25°, θmin = 1.9°
ω scansh = 1212
15105 measured reflectionsk = 1313
5469 independent reflectionsl = 1616
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)] = 0.053Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.129H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0541P)2 + 0.6549P]
where P = (Fo2 + 2Fc2)/3
5469 reflections(Δ/σ)max = 0.001
397 parametersΔρmax = 0.37 e Å3
0 restraintsΔρmin = 0.25 e Å3
Crystal data top
C18H17ClFNOγ = 80.884 (1)°
Mr = 317.78V = 1553.85 (18) Å3
Triclinic, P1Z = 4
a = 10.5399 (7) ÅMo Kα radiation
b = 11.2005 (7) ŵ = 0.26 mm1
c = 13.4950 (9) ÅT = 273 K
α = 82.597 (1)°0.19 × 0.11 × 0.09 mm
β = 83.890 (1)°
Data collection top
Bruker Smart APEX CCD area-detector
diffractometer
4629 reflections with I > 2σ(I)
15105 measured reflectionsRint = 0.026
5469 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.129H-atom parameters constrained
S = 1.09Δρmax = 0.37 e Å3
5469 reflectionsΔρmin = 0.25 e Å3
397 parameters
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
Cl10.38827 (7)0.39601 (8)0.56352 (5)0.0695 (2)
F10.60640 (17)0.19713 (17)0.56734 (11)0.0764 (5)
O10.70194 (16)0.02413 (15)0.23647 (13)0.0529 (5)
N10.43372 (17)0.33660 (16)0.19241 (13)0.0397 (4)
H1A0.40970.41780.18580.048*
C10.5646 (2)0.2317 (2)0.47448 (17)0.0495 (6)
C20.4632 (2)0.3241 (2)0.46186 (16)0.0451 (6)
C30.4213 (2)0.3602 (2)0.36792 (16)0.0410 (5)
H30.35300.42320.35930.049*
C40.4804 (2)0.30291 (19)0.28576 (15)0.0355 (5)
C50.5187 (2)0.3061 (2)0.10376 (15)0.0368 (5)
H50.59060.35320.09760.044*
C60.5735 (2)0.1701 (2)0.12050 (16)0.0383 (5)
H60.63070.14970.06100.046*
C70.4702 (2)0.0878 (2)0.13540 (19)0.0480 (6)
H710.42850.09380.07390.058*
H720.40530.11440.18770.058*
C80.5277 (3)0.0438 (2)0.1644 (2)0.0631 (7)
H810.45930.09370.17970.076*
H820.58420.07410.10870.076*
C90.6029 (3)0.0520 (2)0.2546 (2)0.0624 (8)
H910.54460.02780.31150.075*
H920.64170.13580.27130.075*
C100.6551 (2)0.1497 (2)0.21039 (16)0.0411 (5)
H100.73090.19050.18970.049*
C110.5839 (2)0.2090 (2)0.29950 (16)0.0368 (5)
C120.6242 (2)0.1741 (2)0.39497 (17)0.0466 (6)
H120.69220.11110.40490.056*
C130.4482 (2)0.33888 (19)0.00965 (15)0.0351 (5)
C140.3154 (2)0.3528 (2)0.01000 (17)0.0459 (6)
H140.26520.34140.07050.055*
C150.2565 (2)0.3835 (2)0.07812 (19)0.0532 (6)
H150.16700.39330.07650.064*
C160.3289 (3)0.3996 (2)0.16818 (18)0.0518 (6)
H160.28880.42060.22740.062*
C170.4607 (2)0.3844 (2)0.17021 (17)0.0514 (6)
H170.51040.39400.23110.062*
C180.5196 (2)0.3551 (2)0.08227 (17)0.0441 (6)
H180.60910.34590.08450.053*
Cl1'0.12764 (8)0.08374 (8)1.11111 (5)0.0714 (2)
F1'0.07605 (16)0.29479 (16)1.11800 (10)0.0712 (5)
O1'0.19761 (16)0.47460 (15)0.77456 (12)0.0511 (4)
N1'0.05158 (19)0.15115 (17)0.74056 (13)0.0433 (5)
H1A'0.06380.06930.74660.052*
C1'0.0474 (2)0.2583 (2)1.02500 (17)0.0476 (6)
C2'0.0474 (2)0.1606 (2)1.01076 (17)0.0470 (6)
C3'0.0786 (2)0.1241 (2)0.91682 (17)0.0441 (6)
H3'0.14230.05780.90760.053*
C4'0.0156 (2)0.1857 (2)0.83509 (15)0.0370 (5)
C5'0.0319 (2)0.19373 (19)0.65985 (16)0.0376 (5)
H5'0.10760.15140.67270.045*
C6'0.0778 (2)0.3307 (2)0.66291 (16)0.0381 (5)
H6'0.13580.35850.60980.046*
C7'0.0312 (2)0.4067 (2)0.64576 (17)0.0447 (6)
H71'0.07190.40240.57810.054*
H72'0.09570.37430.69220.054*
C8'0.0191 (3)0.5386 (2)0.6606 (2)0.0599 (7)
H81'0.05270.58410.65610.072*
H82'0.07420.57450.60810.072*
C9'0.0945 (3)0.5467 (2)0.7616 (2)0.0582 (7)
H91'0.03690.51890.81400.070*
H92'0.13000.63100.76800.070*
C10'0.1553 (2)0.3490 (2)0.76359 (16)0.0399 (5)
H10'0.23300.31080.76470.048*
C11'0.0816 (2)0.2840 (2)0.85074 (16)0.0365 (5)
C12'0.1108 (2)0.3196 (2)0.94652 (17)0.0441 (6)
H12'0.17400.38580.95710.053*
C13'0.0357 (2)0.16573 (18)0.55893 (15)0.0359 (5)
C14'0.1683 (2)0.1485 (2)0.53974 (17)0.0447 (6)
H14'0.21980.15270.59070.054*
C15'0.2255 (3)0.1250 (2)0.44585 (18)0.0529 (6)
H15'0.31490.11280.43420.063*
C16'0.1512 (3)0.1197 (2)0.37018 (18)0.0568 (7)
H16'0.18990.10340.30720.068*
C17'0.0193 (3)0.1383 (2)0.38715 (18)0.0558 (7)
H17'0.03140.13590.33530.067*
C18'0.0382 (2)0.1604 (2)0.48091 (17)0.0446 (6)
H18'0.12760.17200.49200.054*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0773 (5)0.0966 (6)0.0376 (4)0.0122 (4)0.0063 (3)0.0291 (3)
F10.0863 (12)0.1060 (13)0.0356 (8)0.0004 (10)0.0236 (8)0.0055 (8)
O10.0528 (10)0.0475 (10)0.0540 (10)0.0173 (8)0.0170 (8)0.0095 (8)
N10.0491 (11)0.0371 (10)0.0290 (9)0.0084 (8)0.0047 (8)0.0066 (8)
C10.0544 (15)0.0635 (16)0.0326 (12)0.0096 (13)0.0144 (11)0.0032 (11)
C20.0519 (14)0.0560 (15)0.0311 (12)0.0149 (12)0.0007 (10)0.0135 (10)
C30.0438 (13)0.0429 (13)0.0360 (12)0.0017 (10)0.0028 (10)0.0095 (10)
C40.0390 (12)0.0360 (12)0.0319 (11)0.0043 (9)0.0050 (9)0.0058 (9)
C50.0374 (12)0.0424 (13)0.0298 (11)0.0021 (10)0.0031 (9)0.0061 (9)
C60.0382 (12)0.0448 (13)0.0302 (11)0.0034 (10)0.0017 (9)0.0105 (9)
C70.0527 (14)0.0457 (14)0.0475 (14)0.0008 (11)0.0176 (11)0.0095 (11)
C80.083 (2)0.0431 (15)0.0662 (18)0.0017 (13)0.0263 (15)0.0120 (13)
C90.086 (2)0.0357 (14)0.0659 (18)0.0034 (13)0.0279 (15)0.0037 (12)
C100.0358 (12)0.0446 (13)0.0412 (13)0.0024 (10)0.0060 (10)0.0063 (10)
C110.0363 (12)0.0407 (12)0.0344 (12)0.0048 (9)0.0075 (9)0.0055 (9)
C120.0443 (13)0.0534 (15)0.0421 (13)0.0000 (11)0.0139 (11)0.0053 (11)
C130.0416 (12)0.0328 (11)0.0308 (11)0.0032 (9)0.0038 (9)0.0050 (9)
C140.0421 (13)0.0583 (15)0.0349 (12)0.0038 (11)0.0003 (10)0.0039 (11)
C150.0416 (14)0.0693 (17)0.0484 (15)0.0031 (12)0.0107 (11)0.0065 (13)
C160.0624 (17)0.0614 (16)0.0340 (13)0.0097 (13)0.0168 (11)0.0026 (11)
C170.0570 (16)0.0687 (17)0.0292 (12)0.0160 (13)0.0009 (11)0.0023 (11)
C180.0403 (13)0.0564 (15)0.0364 (12)0.0093 (11)0.0023 (10)0.0062 (11)
Cl1'0.0869 (5)0.0923 (6)0.0386 (4)0.0259 (4)0.0261 (3)0.0121 (3)
F1'0.0833 (11)0.1026 (13)0.0334 (8)0.0258 (10)0.0073 (7)0.0250 (8)
O1'0.0480 (10)0.0471 (10)0.0519 (10)0.0130 (8)0.0002 (8)0.0102 (8)
N1'0.0583 (12)0.0372 (10)0.0294 (10)0.0099 (9)0.0065 (8)0.0033 (8)
C1'0.0512 (14)0.0661 (17)0.0303 (12)0.0222 (13)0.0044 (10)0.0128 (11)
C2'0.0534 (14)0.0611 (16)0.0299 (12)0.0226 (12)0.0086 (10)0.0044 (11)
C3'0.0501 (14)0.0438 (13)0.0363 (13)0.0036 (11)0.0060 (10)0.0017 (10)
C4'0.0406 (12)0.0391 (12)0.0298 (11)0.0050 (10)0.0026 (9)0.0002 (9)
C5'0.0420 (12)0.0375 (12)0.0328 (12)0.0034 (9)0.0046 (9)0.0041 (9)
C6'0.0392 (12)0.0422 (12)0.0305 (11)0.0040 (10)0.0090 (9)0.0022 (9)
C7'0.0497 (14)0.0429 (13)0.0372 (12)0.0003 (11)0.0041 (10)0.0026 (10)
C8'0.0780 (19)0.0411 (14)0.0560 (16)0.0057 (13)0.0069 (14)0.0027 (12)
C9'0.0778 (19)0.0361 (13)0.0561 (16)0.0021 (13)0.0041 (14)0.0091 (12)
C10'0.0328 (12)0.0436 (13)0.0417 (13)0.0020 (10)0.0032 (9)0.0079 (10)
C11'0.0339 (11)0.0414 (12)0.0338 (12)0.0065 (9)0.0019 (9)0.0051 (9)
C12'0.0387 (13)0.0530 (14)0.0415 (13)0.0096 (11)0.0049 (10)0.0125 (11)
C13'0.0477 (13)0.0283 (11)0.0316 (11)0.0044 (9)0.0060 (9)0.0024 (9)
C14'0.0499 (14)0.0495 (14)0.0353 (12)0.0048 (11)0.0069 (10)0.0076 (10)
C15'0.0577 (16)0.0567 (16)0.0422 (14)0.0062 (12)0.0055 (12)0.0087 (12)
C16'0.084 (2)0.0533 (16)0.0324 (13)0.0111 (14)0.0052 (13)0.0096 (11)
C17'0.088 (2)0.0508 (15)0.0332 (13)0.0136 (14)0.0196 (13)0.0067 (11)
C18'0.0529 (14)0.0420 (13)0.0409 (13)0.0080 (11)0.0125 (11)0.0044 (10)
Geometric parameters (Å, º) top
Cl1—C21.734 (2)Cl1'—C2'1.733 (2)
F1—C11.361 (3)F1'—C1'1.359 (3)
O1—C101.426 (3)O1'—C10'1.429 (3)
O1—C91.432 (3)O1'—C9'1.437 (3)
N1—C41.386 (3)N1'—C4'1.378 (3)
N1—C51.460 (3)N1'—C5'1.458 (3)
N1—H1A0.9000N1'—H1A'0.9000
C1—C121.367 (3)C1'—C12'1.363 (3)
C1—C21.372 (4)C1'—C2'1.377 (4)
C2—C31.377 (3)C2'—C3'1.373 (3)
C3—C41.392 (3)C3'—C4'1.396 (3)
C3—H30.9300C3'—H3'0.9300
C4—C111.400 (3)C4'—C11'1.401 (3)
C5—C131.515 (3)C5'—C13'1.514 (3)
C5—C61.538 (3)C5'—C6'1.538 (3)
C5—H50.9800C5'—H5'0.9800
C6—C71.517 (3)C6'—C7'1.517 (3)
C6—C101.534 (3)C6'—C10'1.529 (3)
C6—H60.9800C6'—H6'0.9800
C7—C81.521 (3)C7'—C8'1.520 (3)
C7—H710.9700C7'—H71'0.9700
C7—H720.9700C7'—H72'0.9700
C8—C91.508 (4)C8'—C9'1.507 (4)
C8—H810.9700C8'—H81'0.9700
C8—H820.9700C8'—H82'0.9700
C9—H910.9700C9'—H91'0.9700
C9—H920.9700C9'—H92'0.9700
C10—C111.519 (3)C10'—C11'1.521 (3)
C10—H100.9800C10'—H10'0.9800
C11—C121.388 (3)C11'—C12'1.391 (3)
C12—H120.9300C12'—H12'0.9300
C13—C141.383 (3)C13'—C14'1.382 (3)
C13—C181.387 (3)C13'—C18'1.387 (3)
C14—C151.379 (3)C14'—C15'1.382 (3)
C14—H140.9300C14'—H14'0.9300
C15—C161.372 (3)C15'—C16'1.364 (4)
C15—H150.9300C15'—H15'0.9300
C16—C171.371 (4)C16'—C17'1.372 (4)
C16—H160.9300C16'—H16'0.9300
C17—C181.376 (3)C17'—C18'1.378 (3)
C17—H170.9300C17'—H17'0.9300
C18—H180.9300C18'—H18'0.9300
C10—O1—C9113.90 (17)C10'—O1'—C9'113.55 (17)
C4—N1—C5118.23 (17)C4'—N1'—C5'120.02 (18)
C4—N1—H1A107.8C4'—N1'—H1A'107.3
C5—N1—H1A107.8C5'—N1'—H1A'107.3
F1—C1—C12119.6 (2)F1'—C1'—C12'119.9 (2)
F1—C1—C2119.6 (2)F1'—C1'—C2'119.5 (2)
C12—C1—C2120.9 (2)C12'—C1'—C2'120.7 (2)
C1—C2—C3119.8 (2)C3'—C2'—C1'120.0 (2)
C1—C2—Cl1120.33 (18)C3'—C2'—Cl1'119.8 (2)
C3—C2—Cl1119.85 (19)C1'—C2'—Cl1'120.19 (18)
C2—C3—C4120.4 (2)C2'—C3'—C4'120.5 (2)
C2—C3—H3119.8C2'—C3'—H3'119.8
C4—C3—H3119.8C4'—C3'—H3'119.8
N1—C4—C3119.82 (19)N1'—C4'—C3'119.8 (2)
N1—C4—C11120.89 (19)N1'—C4'—C11'121.17 (19)
C3—C4—C11119.25 (19)C3'—C4'—C11'119.0 (2)
N1—C5—C13111.03 (17)N1'—C5'—C13'111.50 (17)
N1—C5—C6107.98 (17)N1'—C5'—C6'108.22 (17)
C13—C5—C6112.69 (17)C13'—C5'—C6'112.25 (17)
N1—C5—H5108.3N1'—C5'—H5'108.2
C13—C5—H5108.3C13'—C5'—H5'108.2
C6—C5—H5108.3C6'—C5'—H5'108.2
C7—C6—C10111.17 (18)C7'—C6'—C10'110.79 (18)
C7—C6—C5113.19 (18)C7'—C6'—C5'113.51 (18)
C10—C6—C5108.34 (17)C10'—C6'—C5'108.52 (17)
C7—C6—H6108.0C7'—C6'—H6'107.9
C10—C6—H6108.0C10'—C6'—H6'107.9
C5—C6—H6108.0C5'—C6'—H6'107.9
C6—C7—C8111.0 (2)C6'—C7'—C8'110.7 (2)
C6—C7—H71109.4C6'—C7'—H71'109.5
C8—C7—H71109.4C8'—C7'—H71'109.5
C6—C7—H72109.4C6'—C7'—H72'109.5
C8—C7—H72109.4C8'—C7'—H72'109.5
H71—C7—H72108.0H71'—C7'—H72'108.1
C9—C8—C7109.7 (2)C9'—C8'—C7'110.5 (2)
C9—C8—H81109.7C9'—C8'—H81'109.5
C7—C8—H81109.7C7'—C8'—H81'109.5
C9—C8—H82109.7C9'—C8'—H82'109.5
C7—C8—H82109.7C7'—C8'—H82'109.5
H81—C8—H82108.2H81'—C8'—H82'108.1
O1—C9—C8111.6 (2)O1'—C9'—C8'111.8 (2)
O1—C9—H91109.3O1'—C9'—H91'109.3
C8—C9—H91109.3C8'—C9'—H91'109.3
O1—C9—H92109.3O1'—C9'—H92'109.3
C8—C9—H92109.3C8'—C9'—H92'109.3
H91—C9—H92108.0H91'—C9'—H92'107.9
O1—C10—C11112.11 (18)O1'—C10'—C11'112.06 (18)
O1—C10—C6112.29 (18)O1'—C10'—C6'112.32 (18)
C11—C10—C6111.66 (17)C11'—C10'—C6'111.35 (17)
O1—C10—H10106.8O1'—C10'—H10'106.9
C11—C10—H10106.8C11'—C10'—H10'106.9
C6—C10—H10106.8C6'—C10'—H10'106.9
C12—C11—C4119.3 (2)C12'—C11'—C4'119.4 (2)
C12—C11—C10120.25 (19)C12'—C11'—C10'120.8 (2)
C4—C11—C10120.44 (18)C4'—C11'—C10'119.82 (18)
C1—C12—C11120.4 (2)C1'—C12'—C11'120.5 (2)
C1—C12—H12119.8C1'—C12'—H12'119.7
C11—C12—H12119.8C11'—C12'—H12'119.7
C14—C13—C18117.7 (2)C14'—C13'—C18'118.0 (2)
C14—C13—C5123.45 (19)C14'—C13'—C5'123.02 (19)
C18—C13—C5118.86 (19)C18'—C13'—C5'118.9 (2)
C15—C14—C13120.9 (2)C13'—C14'—C15'120.8 (2)
C15—C14—H14119.6C13'—C14'—H14'119.6
C13—C14—H14119.6C15'—C14'—H14'119.6
C16—C15—C14120.5 (2)C16'—C15'—C14'120.2 (3)
C16—C15—H15119.8C16'—C15'—H15'119.9
C14—C15—H15119.8C14'—C15'—H15'119.9
C17—C16—C15119.5 (2)C15'—C16'—C17'119.9 (2)
C17—C16—H16120.2C15'—C16'—H16'120.1
C15—C16—H16120.2C17'—C16'—H16'120.1
C16—C17—C18120.1 (2)C16'—C17'—C18'120.1 (2)
C16—C17—H17120.0C16'—C17'—H17'119.9
C18—C17—H17120.0C18'—C17'—H17'119.9
C17—C18—C13121.4 (2)C17'—C18'—C13'120.9 (2)
C17—C18—H18119.3C17'—C18'—H18'119.6
C13—C18—H18119.3C13'—C18'—H18'119.6
F1—C1—C2—C3179.4 (2)F1'—C1'—C2'—C3'179.0 (2)
C12—C1—C2—C30.4 (4)C12'—C1'—C2'—C3'0.1 (4)
F1—C1—C2—Cl10.3 (3)F1'—C1'—C2'—Cl1'0.9 (3)
C12—C1—C2—Cl1179.81 (19)C12'—C1'—C2'—Cl1'179.79 (18)
C1—C2—C3—C40.5 (4)C1'—C2'—C3'—C4'0.4 (4)
Cl1—C2—C3—C4179.80 (17)Cl1'—C2'—C3'—C4'179.48 (17)
C5—N1—C4—C3160.4 (2)C5'—N1'—C4'—C3'165.2 (2)
C5—N1—C4—C1121.7 (3)C5'—N1'—C4'—C11'16.4 (3)
C2—C3—C4—N1177.3 (2)C2'—C3'—C4'—N1'177.3 (2)
C2—C3—C4—C110.6 (3)C2'—C3'—C4'—C11'1.1 (3)
C4—N1—C5—C13174.66 (18)C4'—N1'—C5'—C13'169.23 (19)
C4—N1—C5—C650.7 (2)C4'—N1'—C5'—C6'45.3 (3)
N1—C5—C6—C760.6 (2)N1'—C5'—C6'—C7'61.9 (2)
C13—C5—C6—C762.4 (2)C13'—C5'—C6'—C7'61.5 (2)
N1—C5—C6—C1063.2 (2)N1'—C5'—C6'—C10'61.7 (2)
C13—C5—C6—C10173.78 (17)C13'—C5'—C6'—C10'174.83 (18)
C10—C6—C7—C850.8 (3)C10'—C6'—C7'—C8'51.6 (2)
C5—C6—C7—C8172.97 (19)C5'—C6'—C7'—C8'174.02 (19)
C6—C7—C8—C954.0 (3)C6'—C7'—C8'—C9'53.5 (3)
C10—O1—C9—C858.5 (3)C10'—O1'—C9'—C8'57.3 (3)
C7—C8—C9—O157.1 (3)C7'—C8'—C9'—O1'55.7 (3)
C9—O1—C10—C1172.0 (2)C9'—O1'—C10'—C11'70.7 (2)
C9—O1—C10—C654.7 (3)C9'—O1'—C10'—C6'55.5 (2)
C7—C6—C10—O150.5 (2)C7'—C6'—C10'—O1'52.4 (2)
C5—C6—C10—O1175.44 (17)C5'—C6'—C10'—O1'177.68 (17)
C7—C6—C10—C1176.5 (2)C7'—C6'—C10'—C11'74.2 (2)
C5—C6—C10—C1148.5 (2)C5'—C6'—C10'—C11'51.1 (2)
N1—C4—C11—C12177.1 (2)N1'—C4'—C11'—C12'176.9 (2)
C3—C4—C11—C120.8 (3)C3'—C4'—C11'—C12'1.5 (3)
N1—C4—C11—C105.6 (3)N1'—C4'—C11'—C10'4.1 (3)
C3—C4—C11—C10176.6 (2)C3'—C4'—C11'—C10'177.4 (2)
O1—C10—C11—C1235.1 (3)O1'—C10'—C11'—C12'31.3 (3)
C6—C10—C11—C12162.1 (2)C6'—C10'—C11'—C12'158.1 (2)
O1—C10—C11—C4147.5 (2)O1'—C10'—C11'—C4'149.8 (2)
C6—C10—C11—C420.5 (3)C6'—C10'—C11'—C4'23.0 (3)
F1—C1—C12—C11179.2 (2)F1'—C1'—C12'—C11'179.4 (2)
C2—C1—C12—C110.6 (4)C2'—C1'—C12'—C11'0.5 (4)
C4—C11—C12—C10.8 (3)C4'—C11'—C12'—C1'1.2 (3)
C10—C11—C12—C1176.6 (2)C10'—C11'—C12'—C1'177.7 (2)
N1—C5—C13—C1421.8 (3)N1'—C5'—C13'—C14'23.9 (3)
C6—C5—C13—C1499.5 (2)C6'—C5'—C13'—C14'97.8 (2)
N1—C5—C13—C18158.8 (2)N1'—C5'—C13'—C18'158.05 (19)
C6—C5—C13—C1880.0 (2)C6'—C5'—C13'—C18'80.3 (2)
C18—C13—C14—C150.9 (3)C18'—C13'—C14'—C15'0.8 (3)
C5—C13—C14—C15179.6 (2)C5'—C13'—C14'—C15'179.0 (2)
C13—C14—C15—C160.7 (4)C13'—C14'—C15'—C16'0.6 (4)
C14—C15—C16—C170.3 (4)C14'—C15'—C16'—C17'0.4 (4)
C15—C16—C17—C181.0 (4)C15'—C16'—C17'—C18'1.0 (4)
C16—C17—C18—C130.7 (4)C16'—C17'—C18'—C13'0.8 (4)
C14—C13—C18—C170.2 (3)C14'—C13'—C18'—C17'0.2 (3)
C5—C13—C18—C17179.7 (2)C5'—C13'—C18'—C17'178.4 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1A···O1i0.902.553.016 (2)113
N1—H1A···O1ii0.902.413.034 (2)127
C7—H72···N10.972.562.942 (3)103
C7—H72···N10.972.602.965 (3)102
C3—H3···O1ii0.932.603.368 (3)140
C3—H3···O1i0.932.573.322 (3)138
C10—H10···F1iii0.982.553.523 (3)174
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z1.
(II) 10-chloro-9-fluoro-5-phenyl-3,4,4a,5,6,10b-hexahydro-2H-pyrano[3,2-c]quinoline top
Crystal data top
C18H17ClFNOZ = 4
Mr = 317.78F(000) = 664
Triclinic, P1Dx = 1.379 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3032 (8) ÅCell parameters from 5061 reflections
b = 10.5190 (11) Åθ = 2.8–26.4°
c = 18.1165 (18) ŵ = 0.26 mm1
α = 104.234 (2)°T = 273 K
β = 92.309 (2)°Needle, pale yellow
γ = 91.783 (2)°0.18 × 0.10 × 0.07 mm
V = 1531.1 (3) Å3
Data collection top
Bruker Smart APEX CCD Area Detector
diffractometer
4502 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.029
Graphite monochromatorθmax = 25°, θmin = 1.2°
ω scansh = 99
14616 measured reflectionsk = 1212
5373 independent reflectionsl = 2121
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)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.166H-atom parameters constrained
S = 1.16 w = 1/[σ2(Fo2) + (0.0703P)2 + 1.0004P]
where P = (Fo2 + 2Fc2)/3
5373 reflections(Δ/σ)max < 0.001
397 parametersΔρmax = 0.33 e Å3
0 restraintsΔρmin = 0.26 e Å3
Crystal data top
C18H17ClFNOγ = 91.783 (2)°
Mr = 317.78V = 1531.1 (3) Å3
Triclinic, P1Z = 4
a = 8.3032 (8) ÅMo Kα radiation
b = 10.5190 (11) ŵ = 0.26 mm1
c = 18.1165 (18) ÅT = 273 K
α = 104.234 (2)°0.18 × 0.10 × 0.07 mm
β = 92.309 (2)°
Data collection top
Bruker Smart APEX CCD Area Detector
diffractometer
4502 reflections with I > 2σ(I)
14616 measured reflectionsRint = 0.029
5373 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0670 restraints
wR(F2) = 0.166H-atom parameters constrained
S = 1.16Δρmax = 0.33 e Å3
5373 reflectionsΔρmin = 0.26 e Å3
397 parameters
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
Cl10.92960 (10)0.66010 (9)0.84398 (5)0.0566 (3)
F10.7347 (3)0.87726 (19)0.83181 (13)0.0701 (6)
O10.7914 (2)0.45674 (19)0.94415 (11)0.0415 (5)
N10.3750 (3)0.4581 (3)0.87967 (17)0.0487 (7)
H1A0.30420.49050.91510.058*
C10.6466 (4)0.7737 (3)0.84334 (19)0.0479 (8)
C20.4838 (4)0.7819 (3)0.8493 (2)0.0553 (9)
H20.43340.85770.84510.066*
C30.3949 (4)0.6776 (3)0.8616 (2)0.0527 (8)
H30.28370.68290.86500.063*
C40.4687 (4)0.5637 (3)0.86923 (17)0.0403 (7)
C50.4520 (3)0.3496 (3)0.90213 (17)0.0366 (7)
H50.48920.37820.95590.044*
C60.5982 (3)0.3147 (3)0.85298 (16)0.0338 (6)
H60.56040.29640.79930.041*
C70.6867 (4)0.1955 (3)0.8648 (2)0.0482 (8)
H710.60900.12360.86210.058*
H720.76030.16810.82420.058*
C80.7805 (4)0.2250 (3)0.9408 (2)0.0555 (9)
H810.70600.23600.98160.067*
H820.84700.15180.94320.067*
C90.8861 (4)0.3482 (3)0.9515 (2)0.0543 (9)
H910.94100.36821.00150.065*
H920.96730.33410.91360.065*
C100.7167 (3)0.4332 (3)0.86925 (16)0.0337 (6)
H100.80090.41590.83210.040*
C110.6354 (3)0.5555 (3)0.86298 (15)0.0327 (6)
C120.7220 (4)0.6634 (3)0.85059 (17)0.0392 (7)
C130.3314 (3)0.2351 (3)0.89197 (17)0.0392 (7)
C140.2407 (4)0.1882 (4)0.8246 (2)0.0567 (9)
H140.25050.22930.78500.068*
C150.1360 (5)0.0808 (4)0.8158 (3)0.0753 (13)
H150.07530.04990.77030.090*
C160.1206 (5)0.0195 (4)0.8734 (4)0.0861 (16)
H160.05000.05320.86690.103*
C170.2091 (6)0.0650 (4)0.9410 (3)0.0839 (14)
H170.19860.02350.98050.101*
C180.3142 (5)0.1732 (4)0.9500 (2)0.0606 (10)
H180.37390.20430.99580.073*
Cl1'0.04433 (10)0.29325 (9)0.33136 (6)0.0609 (3)
F1'0.2427 (3)0.51631 (18)0.32401 (12)0.0660 (6)
O1'0.1925 (2)0.0045 (2)0.44105 (12)0.0443 (5)
N1'0.6000 (3)0.0489 (3)0.38236 (16)0.0462 (6)
H1A'0.67530.05090.41920.055*
C1'0.3308 (4)0.4014 (3)0.33710 (18)0.0458 (8)
C2'0.4946 (4)0.4018 (3)0.34442 (19)0.0513 (8)
H2'0.54640.48050.33880.062*
C3'0.5825 (4)0.2847 (3)0.36021 (19)0.0475 (8)
H3'0.69440.28480.36560.057*
C4'0.5076 (3)0.1658 (3)0.36839 (16)0.0374 (7)
C5'0.5232 (3)0.0770 (3)0.40480 (17)0.0366 (7)
H5'0.49360.09130.45800.044*
C6'0.3690 (3)0.0691 (3)0.35406 (16)0.0357 (6)
H6'0.39870.04510.30080.043*
C7'0.2794 (4)0.1970 (3)0.3671 (2)0.0494 (8)
H71'0.35510.26870.36640.059*
H72'0.19890.19040.32580.059*
C8'0.1976 (4)0.2266 (3)0.4423 (2)0.0569 (9)
H81'0.27860.25020.48400.068*
H82'0.12930.30070.44520.068*
C9'0.0971 (4)0.1089 (3)0.4497 (2)0.0554 (9)
H91'0.05070.12780.49930.067*
H92'0.00930.09110.41110.067*
C10'0.2560 (3)0.0396 (3)0.36702 (16)0.0353 (6)
H10'0.16600.05400.32880.042*
C11'0.3390 (3)0.1657 (3)0.35975 (16)0.0353 (6)
C12'0.2532 (4)0.2864 (3)0.34365 (16)0.0395 (7)
C13'0.6398 (3)0.1867 (3)0.39848 (18)0.0411 (7)
C14'0.7152 (4)0.1836 (4)0.3322 (2)0.0608 (10)
H14'0.69780.11140.29080.073*
C15'0.8170 (5)0.2868 (6)0.3263 (3)0.0822 (14)
H15'0.86740.28420.28110.099*
C16'0.8436 (5)0.3942 (5)0.3880 (4)0.0899 (17)
H16'0.91180.46400.38440.108*
C17'0.7702 (6)0.3965 (4)0.4530 (3)0.0847 (14)
H17'0.78830.46840.49460.102*
C18'0.6688 (5)0.2942 (4)0.4589 (2)0.0625 (10)
H18'0.61900.29770.50440.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0385 (4)0.0563 (5)0.0784 (6)0.0145 (4)0.0045 (4)0.0251 (4)
F10.0830 (15)0.0433 (11)0.0924 (16)0.0107 (10)0.0010 (12)0.0353 (11)
O10.0347 (11)0.0386 (11)0.0486 (12)0.0002 (9)0.0057 (9)0.0073 (9)
N10.0320 (14)0.0428 (15)0.0722 (19)0.0041 (11)0.0135 (12)0.0139 (13)
C10.060 (2)0.0346 (17)0.053 (2)0.0022 (15)0.0037 (16)0.0181 (14)
C20.061 (2)0.0387 (18)0.069 (2)0.0096 (16)0.0068 (18)0.0211 (17)
C30.0374 (17)0.053 (2)0.068 (2)0.0097 (15)0.0027 (15)0.0146 (17)
C40.0353 (16)0.0351 (16)0.0488 (18)0.0019 (13)0.0008 (13)0.0080 (13)
C50.0328 (15)0.0337 (15)0.0404 (16)0.0043 (12)0.0036 (12)0.0044 (12)
C60.0339 (15)0.0300 (14)0.0345 (15)0.0040 (12)0.0031 (12)0.0029 (12)
C70.0463 (18)0.0314 (16)0.066 (2)0.0015 (14)0.0124 (16)0.0084 (15)
C80.057 (2)0.0427 (19)0.073 (2)0.0154 (16)0.0105 (18)0.0243 (17)
C90.0420 (18)0.056 (2)0.068 (2)0.0089 (16)0.0085 (16)0.0206 (17)
C100.0278 (14)0.0339 (15)0.0390 (16)0.0013 (11)0.0046 (11)0.0080 (12)
C110.0319 (15)0.0318 (15)0.0328 (15)0.0010 (11)0.0002 (11)0.0055 (11)
C120.0374 (16)0.0401 (16)0.0390 (16)0.0075 (13)0.0004 (12)0.0096 (13)
C130.0309 (15)0.0365 (16)0.0468 (18)0.0047 (12)0.0096 (13)0.0032 (13)
C140.0419 (19)0.058 (2)0.062 (2)0.0071 (16)0.0011 (16)0.0009 (17)
C150.043 (2)0.061 (3)0.101 (3)0.0131 (19)0.002 (2)0.017 (2)
C160.046 (2)0.040 (2)0.159 (5)0.0150 (18)0.024 (3)0.001 (3)
C170.073 (3)0.061 (3)0.128 (4)0.013 (2)0.033 (3)0.041 (3)
C180.059 (2)0.058 (2)0.065 (2)0.0111 (18)0.0131 (18)0.0164 (18)
Cl1'0.0392 (5)0.0492 (5)0.0919 (7)0.0099 (4)0.0015 (4)0.0153 (5)
F1'0.0824 (15)0.0336 (10)0.0803 (15)0.0065 (10)0.0008 (11)0.0126 (9)
O1'0.0379 (11)0.0422 (12)0.0552 (13)0.0075 (9)0.0124 (10)0.0143 (10)
N1'0.0319 (13)0.0462 (15)0.0635 (17)0.0002 (11)0.0055 (12)0.0205 (13)
C1'0.061 (2)0.0319 (16)0.0440 (18)0.0000 (15)0.0020 (15)0.0089 (13)
C2'0.063 (2)0.0397 (18)0.055 (2)0.0183 (16)0.0060 (16)0.0154 (15)
C3'0.0389 (17)0.0506 (19)0.057 (2)0.0121 (15)0.0055 (14)0.0188 (16)
C4'0.0343 (16)0.0428 (17)0.0371 (16)0.0036 (13)0.0019 (12)0.0133 (13)
C5'0.0349 (15)0.0387 (16)0.0394 (16)0.0023 (12)0.0018 (12)0.0161 (13)
C6'0.0338 (15)0.0392 (16)0.0363 (15)0.0005 (12)0.0001 (12)0.0139 (12)
C7'0.0453 (19)0.0373 (17)0.069 (2)0.0004 (14)0.0086 (16)0.0224 (16)
C8'0.057 (2)0.0350 (17)0.075 (2)0.0152 (16)0.0022 (18)0.0052 (16)
C9'0.0454 (19)0.049 (2)0.071 (2)0.0161 (16)0.0123 (17)0.0090 (17)
C10'0.0307 (15)0.0361 (15)0.0389 (16)0.0014 (12)0.0017 (12)0.0094 (12)
C11'0.0347 (15)0.0382 (16)0.0338 (15)0.0001 (12)0.0029 (12)0.0104 (12)
C12'0.0416 (17)0.0390 (17)0.0374 (16)0.0014 (13)0.0012 (13)0.0089 (13)
C13'0.0325 (15)0.0464 (18)0.0477 (18)0.0041 (13)0.0022 (13)0.0195 (14)
C14'0.048 (2)0.077 (3)0.063 (2)0.0046 (18)0.0067 (17)0.0266 (19)
C15'0.049 (2)0.121 (4)0.101 (4)0.012 (3)0.006 (2)0.075 (3)
C16'0.054 (3)0.084 (3)0.152 (5)0.028 (2)0.029 (3)0.077 (4)
C17'0.080 (3)0.054 (2)0.117 (4)0.026 (2)0.020 (3)0.024 (3)
C18'0.064 (2)0.058 (2)0.063 (2)0.0169 (19)0.0015 (18)0.0118 (18)
Geometric parameters (Å, º) top
Cl1—C121.734 (3)Cl1'—C12'1.736 (3)
F1—C11.357 (4)F1'—C1'1.357 (4)
O1—C101.430 (3)O1'—C10'1.428 (3)
O1—C91.436 (4)O1'—C9'1.433 (4)
N1—C41.392 (4)N1'—C4'1.391 (4)
N1—C51.459 (4)N1'—C5'1.461 (4)
N1—H1A0.9000N1'—H1A'0.9000
C1—C21.365 (5)C1'—C2'1.361 (5)
C1—C121.366 (4)C1'—C12'1.370 (4)
C2—C31.371 (5)C2'—C3'1.373 (5)
C2—H20.9300C2'—H2'0.9300
C3—C41.397 (4)C3'—C4'1.392 (4)
C3—H30.9300C3'—H3'0.9300
C4—C111.397 (4)C4'—C11'1.403 (4)
C5—C131.512 (4)C5'—C13'1.513 (4)
C5—C61.535 (4)C5'—C6'1.533 (4)
C5—H50.9800C5'—H5'0.9800
C6—C101.526 (4)C6'—C10'1.525 (4)
C6—C71.528 (4)C6'—C7'1.529 (4)
C6—H60.9800C6'—H6'0.9800
C7—C81.512 (5)C7'—C8'1.514 (5)
C7—H710.9700C7'—H71'0.9700
C7—H720.9700C7'—H72'0.9700
C8—C91.509 (5)C8'—C9'1.509 (5)
C8—H810.9700C8'—H81'0.9700
C8—H820.9700C8'—H82'0.9700
C9—H910.9700C9'—H91'0.9700
C9—H920.9700C9'—H92'0.9700
C10—C111.497 (4)C10'—C11'1.494 (4)
C10—H100.9800C10'—H10'0.9800
C11—C121.394 (4)C11'—C12'1.396 (4)
C13—C181.376 (5)C13'—C14'1.370 (5)
C13—C141.381 (5)C13'—C18'1.374 (5)
C14—C151.377 (5)C14'—C15'1.382 (6)
C14—H140.9300C14'—H14'0.9300
C15—C161.362 (7)C15'—C16'1.384 (7)
C15—H150.9300C15'—H15'0.9300
C16—C171.374 (7)C16'—C17'1.344 (7)
C16—H160.9300C16'—H16'0.9300
C17—C181.385 (5)C17'—C18'1.373 (5)
C17—H170.9300C17'—H17'0.9300
C18—H180.9300C18'—H18'0.9300
C10—O1—C9110.8 (2)C10'—O1'—C9'111.1 (2)
C4—N1—C5120.0 (2)C4'—N1'—C5'120.2 (2)
C4—N1—H1A107.3C4'—N1'—H1A'107.3
C5—N1—H1A107.3C5'—N1'—H1A'107.3
F1—C1—C2119.5 (3)F1'—C1'—C2'119.7 (3)
F1—C1—C12119.8 (3)F1'—C1'—C12'119.4 (3)
C2—C1—C12120.6 (3)C2'—C1'—C12'120.9 (3)
C1—C2—C3119.6 (3)C1'—C2'—C3'119.3 (3)
C1—C2—H2120.2C1'—C2'—H2'120.3
C3—C2—H2120.2C3'—C2'—H2'120.3
C2—C3—C4121.0 (3)C2'—C3'—C4'121.4 (3)
C2—C3—H3119.5C2'—C3'—H3'119.3
C4—C3—H3119.5C4'—C3'—H3'119.3
N1—C4—C3119.8 (3)N1'—C4'—C3'120.1 (3)
N1—C4—C11120.9 (3)N1'—C4'—C11'120.6 (3)
C3—C4—C11119.3 (3)C3'—C4'—C11'119.3 (3)
N1—C5—C13109.5 (2)N1'—C5'—C13'109.9 (2)
N1—C5—C6107.5 (2)N1'—C5'—C6'107.9 (2)
C13—C5—C6112.4 (2)C13'—C5'—C6'112.6 (2)
N1—C5—H5109.1N1'—C5'—H5'108.8
C13—C5—H5109.1C13'—C5'—H5'108.8
C6—C5—H5109.1C6'—C5'—H5'108.8
C10—C6—C7109.0 (2)C10'—C6'—C7'109.2 (2)
C10—C6—C5108.9 (2)C10'—C6'—C5'108.8 (2)
C7—C6—C5114.6 (2)C7'—C6'—C5'114.4 (2)
C10—C6—H6108.0C10'—C6'—H6'108.1
C7—C6—H6108.0C7'—C6'—H6'108.1
C5—C6—H6108.0C5'—C6'—H6'108.1
C8—C7—C6111.9 (3)C8'—C7'—C6'111.8 (3)
C8—C7—H71109.2C8'—C7'—H71'109.3
C6—C7—H71109.2C6'—C7'—H71'109.3
C8—C7—H72109.2C8'—C7'—H72'109.3
C6—C7—H72109.2C6'—C7'—H72'109.3
H71—C7—H72107.9H71'—C7'—H72'107.9
C9—C8—C7110.6 (3)C9'—C8'—C7'110.5 (3)
C9—C8—H81109.5C9'—C8'—H81'109.6
C7—C8—H81109.5C7'—C8'—H81'109.6
C9—C8—H82109.5C9'—C8'—H82'109.6
C7—C8—H82109.5C7'—C8'—H82'109.6
H81—C8—H82108.1H81'—C8'—H82'108.1
O1—C9—C8110.6 (3)O1'—C9'—C8'111.1 (3)
O1—C9—H91109.5O1'—C9'—H91'109.4
C8—C9—H91109.5C8'—C9'—H91'109.4
O1—C9—H92109.5O1'—C9'—H92'109.4
C8—C9—H92109.5C8'—C9'—H92'109.4
H91—C9—H92108.1H91'—C9'—H92'108.0
O1—C10—C11107.9 (2)O1'—C10'—C11'107.7 (2)
O1—C10—C6111.3 (2)O1'—C10'—C6'111.3 (2)
C11—C10—C6111.7 (2)C11'—C10'—C6'112.1 (2)
O1—C10—H10108.6O1'—C10'—H10'108.6
C11—C10—H10108.6C11'—C10'—H10'108.6
C6—C10—H10108.6C6'—C10'—H10'108.6
C12—C11—C4118.1 (3)C12'—C11'—C4'118.0 (3)
C12—C11—C10121.6 (2)C12'—C11'—C10'121.8 (3)
C4—C11—C10120.3 (2)C4'—C11'—C10'120.2 (3)
C1—C12—C11121.4 (3)C1'—C12'—C11'121.2 (3)
C1—C12—Cl1118.4 (2)C1'—C12'—Cl1'118.6 (2)
C11—C12—Cl1120.2 (2)C11'—C12'—Cl1'120.2 (2)
C18—C13—C14118.7 (3)C14'—C13'—C18'118.4 (3)
C18—C13—C5119.7 (3)C14'—C13'—C5'121.2 (3)
C14—C13—C5121.5 (3)C18'—C13'—C5'120.4 (3)
C15—C14—C13120.4 (4)C13'—C14'—C15'120.6 (4)
C15—C14—H14119.8C13'—C14'—H14'119.7
C13—C14—H14119.8C15'—C14'—H14'119.7
C16—C15—C14120.5 (4)C14'—C15'—C16'119.8 (4)
C16—C15—H15119.8C14'—C15'—H15'120.1
C14—C15—H15119.8C16'—C15'—H15'120.1
C15—C16—C17120.1 (4)C17'—C16'—C15'119.4 (4)
C15—C16—H16119.9C17'—C16'—H16'120.3
C17—C16—H16119.9C15'—C16'—H16'120.3
C16—C17—C18119.5 (4)C16'—C17'—C18'120.8 (5)
C16—C17—H17120.3C16'—C17'—H17'119.6
C18—C17—H17120.3C18'—C17'—H17'119.6
C13—C18—C17120.8 (4)C17'—C18'—C13'121.0 (4)
C13—C18—H18119.6C17'—C18'—H18'119.5
C17—C18—H18119.6C13'—C18'—H18'119.5
F1—C1—C2—C3179.5 (3)F1'—C1'—C2'—C3'177.8 (3)
C12—C1—C2—C31.0 (5)C12'—C1'—C2'—C3'1.4 (5)
C1—C2—C3—C40.9 (5)C1'—C2'—C3'—C4'0.4 (5)
C5—N1—C4—C3168.2 (3)C5'—N1'—C4'—C3'168.7 (3)
C5—N1—C4—C1114.5 (4)C5'—N1'—C4'—C11'13.5 (4)
C2—C3—C4—N1178.3 (3)C2'—C3'—C4'—N1'178.3 (3)
C2—C3—C4—C111.0 (5)C2'—C3'—C4'—C11'0.5 (5)
C4—N1—C5—C13167.0 (3)C4'—N1'—C5'—C13'166.7 (3)
C4—N1—C5—C644.6 (4)C4'—N1'—C5'—C6'43.6 (3)
N1—C5—C6—C1061.9 (3)N1'—C5'—C6'—C10'61.2 (3)
C13—C5—C6—C10177.5 (2)C13'—C5'—C6'—C10'177.4 (2)
N1—C5—C6—C7175.7 (2)N1'—C5'—C6'—C7'176.3 (2)
C13—C5—C6—C755.1 (3)C13'—C5'—C6'—C7'54.9 (3)
C10—C6—C7—C850.4 (3)C10'—C6'—C7'—C8'50.4 (3)
C5—C6—C7—C872.0 (3)C5'—C6'—C7'—C8'71.8 (3)
C6—C7—C8—C951.0 (4)C6'—C7'—C8'—C9'50.8 (4)
C10—O1—C9—C862.7 (3)C10'—O1'—C9'—C8'62.1 (3)
C7—C8—C9—O156.2 (4)C7'—C8'—C9'—O1'55.8 (4)
C9—O1—C10—C11173.9 (2)C9'—O1'—C10'—C11'174.2 (2)
C9—O1—C10—C663.2 (3)C9'—O1'—C10'—C6'62.6 (3)
C7—C6—C10—O156.1 (3)C7'—C6'—C10'—O1'55.9 (3)
C5—C6—C10—O169.6 (3)C5'—C6'—C10'—O1'69.7 (3)
C7—C6—C10—C11176.8 (2)C7'—C6'—C10'—C11'176.6 (2)
C5—C6—C10—C1151.0 (3)C5'—C6'—C10'—C11'51.0 (3)
N1—C4—C11—C12178.4 (3)N1'—C4'—C11'—C12'178.2 (3)
C3—C4—C11—C121.1 (4)C3'—C4'—C11'—C12'0.4 (4)
N1—C4—C11—C101.4 (4)N1'—C4'—C11'—C10'1.2 (4)
C3—C4—C11—C10178.7 (3)C3'—C4'—C11'—C10'179.0 (3)
O1—C10—C11—C1278.7 (3)O1'—C10'—C11'—C12'79.2 (3)
C6—C10—C11—C12158.7 (3)C6'—C10'—C11'—C12'158.0 (3)
O1—C10—C11—C4101.5 (3)O1'—C10'—C11'—C4'101.3 (3)
C6—C10—C11—C421.1 (4)C6'—C10'—C11'—C4'21.4 (4)
F1—C1—C12—C11179.6 (3)F1'—C1'—C12'—C11'177.7 (3)
C2—C1—C12—C111.1 (5)C2'—C1'—C12'—C11'1.5 (5)
F1—C1—C12—Cl10.5 (4)F1'—C1'—C12'—Cl1'2.4 (4)
C2—C1—C12—Cl1178.9 (3)C2'—C1'—C12'—Cl1'178.4 (3)
C4—C11—C12—C11.1 (4)C4'—C11'—C12'—C1'0.5 (4)
C10—C11—C12—C1178.6 (3)C10'—C11'—C12'—C1'180.0 (3)
C4—C11—C12—Cl1178.9 (2)C4'—C11'—C12'—Cl1'179.4 (2)
C10—C11—C12—Cl11.3 (4)C10'—C11'—C12'—Cl1'0.1 (4)
N1—C5—C13—C18131.6 (3)N1'—C5'—C13'—C14'53.6 (4)
C6—C5—C13—C18109.0 (3)C6'—C5'—C13'—C14'66.8 (4)
N1—C5—C13—C1450.4 (4)N1'—C5'—C13'—C18'128.4 (3)
C6—C5—C13—C1469.0 (4)C6'—C5'—C13'—C18'111.3 (3)
C18—C13—C14—C150.4 (5)C18'—C13'—C14'—C15'0.5 (5)
C5—C13—C14—C15177.6 (3)C5'—C13'—C14'—C15'177.6 (3)
C13—C14—C15—C160.1 (6)C13'—C14'—C15'—C16'0.3 (6)
C14—C15—C16—C170.4 (6)C14'—C15'—C16'—C17'0.1 (7)
C15—C16—C17—C180.2 (7)C15'—C16'—C17'—C18'0.3 (7)
C14—C13—C18—C170.6 (5)C16'—C17'—C18'—C13'0.1 (7)
C5—C13—C18—C17177.5 (3)C14'—C13'—C18'—C17'0.3 (6)
C16—C17—C18—C130.3 (6)C5'—C13'—C18'—C17'177.8 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10—H10···Cl10.982.713.061 (3)102
C10—H10···Cl10.982.703.065 (3)103

Experimental details

(I)(II)
Crystal data
Chemical formulaC18H17ClFNOC18H17ClFNO
Mr317.78317.78
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)273273
a, b, c (Å)10.5399 (7), 11.2005 (7), 13.4950 (9)8.3032 (8), 10.5190 (11), 18.1165 (18)
α, β, γ (°)82.597 (1), 83.890 (1), 80.884 (1)104.234 (2), 92.309 (2), 91.783 (2)
V3)1553.85 (18)1531.1 (3)
Z44
Radiation typeMo KαMo Kα
µ (mm1)0.260.26
Crystal size (mm)0.19 × 0.11 × 0.090.18 × 0.10 × 0.07
Data collection
DiffractometerBruker Smart APEX CCD area-detector
diffractometer
Bruker Smart APEX CCD Area Detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
15105, 5469, 4629 14616, 5373, 4502
Rint0.0260.029
(sin θ/λ)max1)0.5950.595
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.129, 1.09 0.067, 0.166, 1.16
No. of reflections54695373
No. of parameters397397
H-atom treatmentH-atom parameters constrainedH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.37, 0.250.33, 0.26

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), SAINT, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL/PC (Sheldrick, 1990), SHELXL97 and PARST (Nardelli, 1995).

Selected geometric parameters (Å, º) for (I) top
O1—C101.426 (3)O1'—C10'1.429 (3)
O1—C91.432 (3)O1'—C9'1.437 (3)
N1—C41.386 (3)N1'—C4'1.378 (3)
N1—C51.460 (3)N1'—C5'1.458 (3)
C16—C171.371 (4)C16'—C17'1.372 (4)
C10—O1—C9113.90 (17)C10'—O1'—C9'113.55 (17)
C4—N1—C5118.23 (17)C4'—N1'—C5'120.02 (18)
C14—C13—C5123.45 (19)C14'—C13'—C5'123.02 (19)
C16—C17—C18120.1 (2)C16'—C17'—C18'120.1 (2)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1'—H1A'···O1i0.902.553.016 (2)113
N1—H1A···O1'ii0.902.413.034 (2)127
C7—H72···N10.972.562.942 (3)103
C7'—H72'···N1'0.972.602.965 (3)102
C3—H3···O1'ii0.932.603.368 (3)140
C3'—H3'···O1i0.932.573.322 (3)138
C10—H10···F1'iii0.982.553.523 (3)174
Symmetry codes: (i) x+1, y, z+1; (ii) x, y+1, z+1; (iii) x+1, y, z1.
Selected bond lengths (Å) for (II) top
O1—C101.430 (3)O1'—C10'1.428 (3)
O1—C91.436 (4)O1'—C9'1.433 (4)
N1—C41.392 (4)N1'—C4'1.391 (4)
N1—C51.459 (4)N1'—C5'1.461 (4)
C16—C171.374 (7)C16'—C17'1.344 (7)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
C10—H10···Cl10.982.713.061 (3)102
C10'—H10'···Cl1'0.982.703.065 (3)103
 

Subscribe to Acta Crystallographica Section C: Structural Chemistry

The full text of this article is available to subscribers to the journal.

If you have already registered and are using a computer listed in your registration details, please email support@iucr.org for assistance.

Buy online

You may purchase this article in PDF and/or HTML formats. For purchasers in the European Community who do not have a VAT number, VAT will be added at the local rate. Payments to the IUCr are handled by WorldPay, who will accept payment by credit card in several currencies. To purchase the article, please complete the form below (fields marked * are required), and then click on `Continue'.
E-mail address* 
Repeat e-mail address* 
(for error checking) 

Format*   PDF (US $40)
   HTML (US $40)
   PDF+HTML (US $50)
In order for VAT to be shown for your country javascript needs to be enabled.

VAT number 
(non-UK EC countries only) 
Country* 
 

Terms and conditions of use
Contact us

Follow Acta Cryst. C
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds