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The title compounds, C20H21F2NO3 and C21H23F2NO3, respectively, belong to a class of 1,4-dihydro­pyridines whose members sometimes display calcium modulatory properties. The 1,4-dihydro­pyridine rings have the usual shallow boat conformation. In each structure, the 2,3-difluoro­phenyl ring is oriented such that the fluoro substituents are in a synperi­planar orientation with respect to the 1,4-dihydro­pyridine ring plane and the oxocyclo­hexene ring has a slightly distorted envelope conformation. Both structures exhibit the same inter­molecular N-H...O hydrogen-bonding motif, in which the mol­ecules are linked into chains by inter­actions involving the carbonyl O atom of the oxocyclo­hexene ring.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270105037066/sk1884sup1.cif
Contains datablocks I, II, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105037066/sk1884Isup2.hkl
Contains datablock I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270105037066/sk1884IIsup3.hkl
Contains datablock II

CCDC references: 294340; 294341

Comment top

1,4-Dihydropyridine (1,4-DHP) derivatives have yielded many drugs that act as calcium channel agonists. Nifedipine is the prototype of this group, and both it and its structural analogues are used as antianginal and antihypertensive drugs (Janis & Triggle, 1984). Many active derivatives have been synthesized by making various modifications to the nifedipine structure, which yield compounds with calcium agonist or antagonist properties (Rose, 1989, 1990). It is thought that the activity displayed by these compounds may be influenced by their stereochemistry (Langs & Triggle, 1985). Our interest is in the structure and calcium antagonistic behaviour of condensed derivatives of 1,4-DHP (Şimşek et al., 2003; Kısmetli et al., 2004). The crystal structures of some of these derivatives have already been reported (Linden et al., 1998, 2002, 2004; Şimşek et al., 2000) and the title compounds, (I) and (II), respectively, have been prepared as further potentially active 1,4-DHP derivatives. Their structures were confirmed by IR, 1H NMR and 13C NMR spectra, mass spectrometry and elemental analyses. Details of the antagonistic activities of these and related compounds will be published elsewhere. The determination of the three-dimensional conformations of the title compounds, presented here, is important in order to obtain further insight into the structure–activity relationships of these compounds.

The switch from the methyl ester in compound (I) to the corresponding ethyl ester in compound (II) has no major influence on the conformations of the molecules. The 1,4-DHP rings (Figs. 1 and 2, respectively) have shallow boat conformations. In (I), atoms N1 and C4 are 0.159 (2) and 0.348 (2) Å, respectively, from the plane defined by atoms C2, C3, C4A and C8A. The corresponding displacements in compound (II) are 0.142 (1) and 0.287 (1) Å, respectively. The shallowness of the boat is indicated by the ring-puckering parameters (Cremer & Pople, 1975). For compound (I), Q = 0.2986 (15) Å, θ = 75.4 (3)° and ϕ2 = 183.5 (3)° for the atom sequence N1—C2—C3—C4—C4A—C8A. For the corresponding atom sequence in compound (II), Q = 0.2507 (13) Å, θ = 76.7 (3)° and ϕ2 = 182.8 (3)°. For an ideal boat, θ and ϕ2 are 90° and n × 60°, respectively. The conformations of 4-aryl-1,4-DHP rings have been discussed previously (Goldmann & Stoltefuss, 1991; Linden et al. 1998, 2002; Şimşek et al., 2000) and it is usual for the ring to have a shallow boat conformation, although considerable variation in the shallowness of the boat is evident. The displacement of atom C4 from the base of the boat in (I) and (II) corresponds with the values of around 0.30 Å found most frequently for this atom in 1,4-DHP rings (Şimşek et al., 2000). The deviations shown by atom N1 are generally smaller and spread fairly evenly over the range 0.00–0.19 Å (Linden et al., 2000, 2002). The deviation shown by atom N1 in (I) and (II) falls well within this range. In contrast, the 1,4-DHP ring in N,N-diethyl-2,6,6-trimethyl-4-(3-nitrophenyl)-5-oxo- 1,4,5,6,7,8-hexahydroquinoline-3-carboxamide was found to be completely planar (Linden et al., 2002).

Another measure of the planarity of 1,4-DHP rings is the sum of the magnitudes of the six intraring torsion angles, P, around the ring (Fossheim et al., 1988). For compounds (I) and (II), P is 101.8 (5) and 85.5 (5)°, respectively, which demonstrates that the boat conformations are somewhat deeper than usual. A mean value of 77 (2)° was found previously for reported 1,4-DHP rings (Linden et al., 2002), although the P values generally vary over a wide range from 4 to 130°. For nifedipine itself, P is 72° (Miyamae et al., 1986).

The plane of the 2,3-difluorophenyl ring in each of the title compounds deviates just slightly from being parallel to the N1···C4 axis. Compound (I) has a N1···C4—C13—C18 torsion angle of 12.19 (16)°, while the corresponding torsion angle, N1···C4—C14—C19, in compound (II) is 14.26 (15)°. These values are quite normal. The corresponding torsion angle in related structures is clustered around 0° and rarely exceeds ±30° (Linden et al., 2002). The fluoro substituents lie above the C4—H bond in a synperiplanar orientation and not over the 1,4-DHP ring, which, because of the substituent in the 2-position of the phenyl ring, would be sterically unfavourable.

The Cambridge Structural Database (CSD; Release 5.26 with August 2005 updates; Allen, 2002) contains only five examples of 4-aryl-1,4-DHP compounds with 2,3-disubstitution in the phenyl ring. Three of these compounds are 4-(2,3-dichlorophenyl)-2,6-dimethyl-3,5-dicarboxy-1,4-DHP derivatives (Fossheim, 1986; Lamm et al., 1989; Caignan & Holt, 2000), while there is one 4-(2-chloro-3-nitrophenyl)- (Rovnyak et al., 1988) and one 4-(2,3-methylenedioxyphenyl)- analogue (Fonseca et al., 1986). In each of these compounds, the 2,3-disubstituted phenyl ring has a synperiplanar orientation, similar to that found in compounds (I) and (II), and the 1,4-DHP ring has a shallow boat conformation. The 1,4-DHP ring in compound (I) actually has the most pronounced boat conformation of all of these compounds.

The oxocyclohexene ring in each of the title compounds has a slightly distorted C7-envelope conformation, as demonstrated by the ring puckering parameters (Cremer & Pople, 1975). For compound (I), Q = 0.4832 (17) Å, θ = 59.10 (19)° and ϕ2 = 173.9 (2)° for the atom sequence C4A—C5—C6—C7—C8—C8A. Atom C7 is 0.658 (2) Å from the plane defined by atoms C4A, C5, C6, C8 and C8A. The maximum deviation of these latter five atoms from their mean plane is 0.043 (1) Å for atom C8A. For the corresponding atom sequence in compound (II), Q = 0.4448 (15) Å, θ = 62.18 (18)° and ϕ2 = 185.2 (2)°, atom C7 is 0.606 (1) Å from the plane defined by the remaining ring atoms, and the maximum deviation of these latter five atoms from their mean plane is 0.051 (1) Å for atom C5. In both structures, atom C7 of the ring flips up on the same side of the oxocyclohexene ring plane as the 2,3-difluorophenyl substituent of the adjacent 1,4-DHP ring. It has been found that atom C7 is always the out-of-plane atom in structures involving the 5-oxoquinoline or 1,8-dioxoacridine moiety and that the side of the oxocyclohexene ring to which C7 deviates is, in the majority, but not all, of these structures, the same as that in (I) and (II) (Linden et al., 2002).

Most of the bond lengths and angles in (I) and (II) have normal values. There are small angular distortions about atoms C2 and C10 (Tables 1 and 3) which result from steric interactions between the methyl substituent at C2 and atom O1O of the ester substituent at C3 [O10···C9 = 2.8248 (19) and 2.8736 (19) Å for (I) and (II), respectively)]. The presence of π-electron conjugation keeps the ester group at C3 almost coplanar [C2C3—C10O10 = −10.6 (2) and 4.4 (2)° for (I) and (II), respectively] with the endocyclic double bond and prevents the ester group from rotating into a sterically more amenable orientation. These properties are consistent with those of the related compound, methyl 4-(2-chloro-5-nitrophenyl)-2,7,7-trimethyl-5-oxo- 1,4,5,6,7,8-hexahydroquinoline-3-carboxylate (Linden et al., 2004), and the many other 2-methyl-3-carboxy-4-aryl-1,4-DHP compounds archived in the CSD.

In compounds (I) and (II), an intermolecular hydrogen bond between the amine group and the carbonyl O atom of the oxocyclohexene ring of a neighbouring molecule (Tables 2 and 4) links the molecules into extended chains which run parallel to the [100] direction and can be described by a graph-set motif of C(6) (Bernstein et al., 1995). The same C(6) motif has been observed in the crystal structures of several other closely related 1,4-DHP compounds (Linden et al., 1998, 2002, 2004; Şimşek et al., 2000).

Experimental top

For the synthesis of the title compounds, equimolar amounts of 2,3-difluorobenzaldehyde, 4,4-dimethylcyclohexanedione and methyl acetoacetate [for (I)] or ethyl acetoacetate [for (II)], together with ammonia (1 ml), were refluxed in methanol for 6 h. The solution was then poured into water, and the precipitate was filtered, dried and recrystallized from ethanol (m.p. 519 and 484 K, respectively).

Refinement top

For each structure, the position of the amine H atom was determined from a difference Fourier map and refined freely along with its isotropic displacement parameter. The methyl H atoms were constrained to an ideal geometry with C—H = 0.98 Å and Uiso(H) = 1.5Ueq(C), but were allowed to rotate freely about the C—C bonds. All remaining H atoms were placed in geometrically idealized positions (C—H = 0.95–1.00 Å) and constrained to ride on their parent atoms with Uiso(H) = 1.2Ueq(C). For (I) and (II), four and two low angle reflections, respectively, were omitted from the final cycles of refinement because their observed intensities were much lower than the calculated values as a result of being partially obscured by the beam stop.

Computing details top

For both compounds, data collection: COLLECT (Nonius, 2000); cell refinement: DENZO-SMN (Otwinowski & Minor, 1997); data reduction: DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. View of the molecule of (I), showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
[Figure 2] Fig. 2. View of the molecule of (II) showing the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level.
(I) (±)-methyl 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo- 1,4,5,6,7,8-hexahydroquinoline-3-carboxylate top
Crystal data top
C20H21F2NO3Z = 2
Mr = 361.39F(000) = 380
Triclinic, P1Dx = 1.403 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.2055 (2) ÅCell parameters from 4905 reflections
b = 9.6702 (4) Åθ = 2.0–30.0°
c = 12.9606 (6) ŵ = 0.11 mm1
α = 93.9639 (19)°T = 160 K
β = 92.624 (2)°Prism, colourless
γ = 107.904 (2)°0.27 × 0.22 × 0.20 mm
V = 855.15 (6) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
3409 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.053
Horizontally mounted graphite crystal monochromatorθmax = 30.0°, θmin = 3.0°
Detector resolution: 9 pixels mm-1h = 010
ϕ and ω scans with κ offsetsk = 1312
21670 measured reflectionsl = 1818
4980 independent reflections
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: geom & difmap
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0583P)2 + 0.1694P]
where P = (Fo2 + 2Fc2)/3
4976 reflections(Δ/σ)max = 0.001
243 parametersΔρmax = 0.32 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C20H21F2NO3γ = 107.904 (2)°
Mr = 361.39V = 855.15 (6) Å3
Triclinic, P1Z = 2
a = 7.2055 (2) ÅMo Kα radiation
b = 9.6702 (4) ŵ = 0.11 mm1
c = 12.9606 (6) ÅT = 160 K
α = 93.9639 (19)°0.27 × 0.22 × 0.20 mm
β = 92.624 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3409 reflections with I > 2σ(I)
21670 measured reflectionsRint = 0.053
4980 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0530 restraints
wR(F2) = 0.137H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.32 e Å3
4976 reflectionsΔρmin = 0.27 e Å3
243 parameters
Special details top

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.573 (2) Frames collected: 406 Seconds exposure per frame: 10 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 35.0

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
xyzUiso*/Ueq
F10.55963 (12)0.41606 (10)0.29982 (7)0.0313 (2)
F20.55884 (13)0.30670 (10)0.48190 (7)0.0348 (2)
O50.60328 (14)0.73105 (11)0.24549 (8)0.0258 (2)
O100.09097 (16)0.21379 (12)0.02186 (9)0.0356 (3)
O110.22881 (14)0.27902 (11)0.06998 (8)0.0273 (3)
N10.07918 (17)0.60996 (13)0.19709 (10)0.0228 (3)
H10.187 (3)0.641 (2)0.2032 (14)0.043 (5)*
C20.0968 (2)0.47989 (15)0.13909 (11)0.0208 (3)
C30.05715 (19)0.42745 (15)0.13928 (11)0.0201 (3)
C40.24052 (19)0.50149 (15)0.21054 (11)0.0193 (3)
H40.35690.49450.17390.023*
C4a0.2606 (2)0.66214 (15)0.23426 (11)0.0197 (3)
C50.4540 (2)0.76767 (15)0.25426 (11)0.0195 (3)
C60.4723 (2)0.92792 (15)0.28174 (12)0.0229 (3)
C70.2881 (2)0.93810 (17)0.33260 (13)0.0271 (3)
H710.28220.89620.40040.033*
H720.29641.04200.34540.033*
C80.1023 (2)0.85787 (16)0.26556 (13)0.0274 (3)
H810.01310.85540.30500.033*
H820.09570.91040.20330.033*
C8a0.0982 (2)0.70525 (15)0.23318 (11)0.0214 (3)
C90.2905 (2)0.41411 (17)0.07901 (12)0.0259 (3)
H910.27000.38080.00860.039*
H920.35850.48750.07580.039*
H930.36980.33110.11340.039*
C100.0510 (2)0.29734 (15)0.07182 (11)0.0222 (3)
C120.2413 (2)0.16022 (17)0.00046 (13)0.0309 (4)
H1210.16590.06750.02540.046*
H1220.37840.16380.00240.046*
H1230.18810.16840.06900.046*
C130.2361 (2)0.42794 (15)0.31152 (11)0.0198 (3)
C140.3958 (2)0.39328 (15)0.35196 (11)0.0220 (3)
C150.3952 (2)0.33561 (16)0.44632 (12)0.0248 (3)
C160.2364 (2)0.30959 (17)0.50472 (12)0.0285 (4)
H160.23850.27200.57040.034*
C170.0721 (2)0.33991 (18)0.46493 (13)0.0297 (4)
H170.04120.32080.50310.036*
C180.0724 (2)0.39750 (17)0.37044 (12)0.0259 (3)
H180.04170.41710.34460.031*
C190.6511 (2)1.00115 (18)0.35628 (14)0.0357 (4)
H1910.76880.99370.32440.054*
H1920.63720.95260.42070.054*
H1930.66231.10420.37170.054*
C200.4957 (3)1.00363 (18)0.18072 (14)0.0343 (4)
H2010.48461.10170.19370.051*
H2020.39320.94680.12840.051*
H2030.62421.01070.15560.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0243 (5)0.0426 (6)0.0328 (5)0.0172 (4)0.0055 (4)0.0086 (4)
F20.0344 (5)0.0418 (6)0.0352 (6)0.0222 (4)0.0048 (4)0.0070 (4)
O50.0191 (5)0.0238 (5)0.0351 (6)0.0085 (4)0.0008 (4)0.0002 (5)
O100.0258 (6)0.0310 (6)0.0452 (7)0.0067 (5)0.0083 (5)0.0119 (5)
O110.0223 (5)0.0258 (6)0.0330 (6)0.0089 (4)0.0011 (4)0.0081 (5)
N10.0166 (6)0.0238 (6)0.0293 (7)0.0085 (5)0.0017 (5)0.0006 (5)
C20.0190 (7)0.0225 (7)0.0203 (7)0.0047 (6)0.0030 (5)0.0047 (6)
C30.0195 (7)0.0205 (7)0.0194 (7)0.0051 (6)0.0014 (5)0.0018 (6)
C40.0169 (7)0.0204 (7)0.0208 (7)0.0064 (5)0.0005 (5)0.0000 (6)
C4a0.0188 (7)0.0201 (7)0.0208 (7)0.0074 (6)0.0009 (5)0.0012 (6)
C50.0197 (7)0.0210 (7)0.0183 (7)0.0076 (6)0.0005 (5)0.0017 (6)
C60.0216 (7)0.0204 (7)0.0270 (8)0.0074 (6)0.0007 (6)0.0000 (6)
C70.0276 (8)0.0225 (8)0.0318 (9)0.0093 (6)0.0029 (6)0.0019 (6)
C80.0216 (7)0.0233 (8)0.0398 (9)0.0110 (6)0.0033 (6)0.0001 (7)
C8a0.0195 (7)0.0219 (7)0.0224 (7)0.0057 (6)0.0024 (6)0.0024 (6)
C90.0188 (7)0.0288 (8)0.0292 (8)0.0061 (6)0.0004 (6)0.0030 (7)
C100.0203 (7)0.0219 (7)0.0238 (8)0.0057 (6)0.0004 (6)0.0028 (6)
C120.0311 (8)0.0271 (8)0.0350 (9)0.0132 (7)0.0033 (7)0.0092 (7)
C130.0209 (7)0.0168 (7)0.0207 (7)0.0053 (5)0.0009 (5)0.0013 (5)
C140.0204 (7)0.0202 (7)0.0255 (8)0.0070 (6)0.0015 (6)0.0005 (6)
C150.0264 (8)0.0221 (7)0.0283 (8)0.0124 (6)0.0053 (6)0.0004 (6)
C160.0351 (9)0.0291 (8)0.0224 (8)0.0110 (7)0.0015 (6)0.0055 (6)
C170.0281 (8)0.0322 (9)0.0293 (9)0.0087 (7)0.0060 (7)0.0059 (7)
C180.0221 (7)0.0283 (8)0.0282 (8)0.0091 (6)0.0002 (6)0.0035 (6)
C190.0300 (9)0.0276 (9)0.0469 (11)0.0101 (7)0.0089 (7)0.0117 (8)
C200.0410 (9)0.0262 (8)0.0391 (10)0.0132 (7)0.0102 (8)0.0087 (7)
Geometric parameters (Å, º) top
F1—C141.3540 (16)C8—C8a1.497 (2)
F2—C151.3607 (16)C8—H810.9900
O5—C51.2388 (16)C8—H820.9900
O10—C101.2155 (17)C9—H910.9800
O11—C101.3474 (16)C9—H920.9800
O11—C121.4379 (18)C9—H930.9800
N1—C8a1.3651 (18)C12—H1210.9800
N1—C21.3878 (18)C12—H1220.9800
N1—H10.915 (19)C12—H1230.9800
C2—C31.3537 (19)C13—C141.3842 (19)
C2—C91.499 (2)C13—C181.401 (2)
C3—C101.470 (2)C14—C151.378 (2)
C3—C41.5253 (19)C15—C161.369 (2)
C4—C4a1.5234 (19)C16—C171.390 (2)
C4—C131.5292 (19)C16—H160.9500
C4—H41.0000C17—C181.380 (2)
C4a—C8a1.3570 (19)C17—H170.9500
C4a—C51.452 (2)C18—H180.9500
C5—C61.5296 (19)C19—H1910.9800
C6—C191.525 (2)C19—H1920.9800
C6—C201.535 (2)C19—H1930.9800
C6—C71.535 (2)C20—H2010.9800
C7—C81.520 (2)C20—H2020.9800
C7—H710.9900C20—H2030.9800
C7—H720.9900
C10—O11—C12115.61 (11)C2—C9—H92109.5
C8a—N1—C2122.11 (12)H91—C9—H92109.5
C8a—N1—H1117.6 (12)C2—C9—H93109.5
C2—N1—H1119.6 (12)H91—C9—H93109.5
N1—C2—C3119.21 (13)H92—C9—H93109.5
N1—C2—C9113.94 (12)O10—C10—O11121.76 (13)
C3—C2—C9126.83 (13)O10—C10—C3126.97 (13)
C2—C3—C10120.94 (13)O11—C10—C3111.28 (12)
C2—C3—C4120.62 (12)O11—C12—H121109.5
C10—C3—C4118.44 (11)O11—C12—H122109.5
C3—C4—C4a109.74 (11)H121—C12—H122109.5
C4a—C4—C13109.92 (11)O11—C12—H123109.5
C3—C4—C13111.54 (11)H121—C12—H123109.5
C4a—C4—H4108.5H122—C12—H123109.5
C3—C4—H4108.5C14—C13—C18116.31 (13)
C13—C4—H4108.5C14—C13—C4122.08 (12)
C8a—C4a—C5120.92 (13)C18—C13—C4121.57 (12)
C4—C4a—C8a119.69 (12)F1—C14—C15117.50 (12)
C5—C4a—C4119.36 (11)F1—C14—C13120.73 (13)
O5—C5—C4a121.20 (12)C15—C14—C13121.77 (13)
O5—C5—C6119.80 (12)F2—C15—C16119.98 (13)
C4a—C5—C6118.94 (12)F2—C15—C14118.42 (13)
C19—C6—C5110.60 (12)C16—C15—C14121.59 (13)
C19—C6—C20109.23 (13)C15—C16—C17117.95 (14)
C5—C6—C20107.55 (12)C15—C16—H16121.0
C19—C6—C7109.27 (13)C17—C16—H16121.0
C5—C6—C7109.55 (12)C18—C17—C16120.50 (14)
C20—C6—C7110.63 (12)C18—C17—H17119.8
C8—C7—C6112.17 (13)C16—C17—H17119.8
C8—C7—H71109.2C17—C18—C13121.85 (13)
C6—C7—H71109.2C17—C18—H18119.1
C8—C7—H72109.2C13—C18—H18119.1
C6—C7—H72109.2C6—C19—H191109.5
H71—C7—H72107.9C6—C19—H192109.5
C8a—C8—C7110.47 (12)H191—C19—H192109.5
C8a—C8—H81109.6C6—C19—H193109.5
C7—C8—H81109.6H191—C19—H193109.5
C8a—C8—H82109.6H192—C19—H193109.5
C7—C8—H82109.6C6—C20—H201109.5
H81—C8—H82108.1C6—C20—H202109.5
C4a—C8a—N1120.38 (13)H201—C20—H202109.5
C4a—C8a—C8123.26 (13)C6—C20—H203109.5
N1—C8a—C8116.30 (12)H201—C20—H203109.5
C2—C9—H91109.5H202—C20—H203109.5
C8a—N1—C2—C316.7 (2)C5—C4a—C8a—C88.3 (2)
C8a—N1—C2—C9161.59 (13)C4—C4a—C8a—C8173.82 (13)
N1—C2—C3—C10174.48 (12)C2—N1—C8a—C4a15.2 (2)
C9—C2—C3—C103.6 (2)C2—N1—C8a—C8162.02 (13)
N1—C2—C3—C46.1 (2)C7—C8—C8a—C4a19.8 (2)
C9—C2—C3—C4175.77 (13)C7—C8—C8a—N1163.05 (13)
C2—C3—C4—C4a26.57 (17)C12—O11—C10—O103.7 (2)
C10—C3—C4—C4a154.03 (12)C12—O11—C10—C3175.85 (12)
C2—C3—C4—C1395.50 (15)C2—C3—C10—O1010.6 (2)
C10—C3—C4—C1383.90 (15)C4—C3—C10—O10168.80 (14)
C3—C4—C4a—C8a28.03 (18)C2—C3—C10—O11168.94 (13)
C13—C4—C4a—C8a95.00 (15)C4—C3—C10—O1111.67 (18)
C3—C4—C4a—C5149.88 (12)C4a—C4—C13—C14104.31 (15)
C13—C4—C4a—C587.09 (15)C3—C4—C13—C14133.73 (13)
C8a—C4a—C5—O5172.93 (13)C4a—C4—C13—C1872.98 (16)
C4—C4a—C5—O55.0 (2)C3—C4—C13—C1848.98 (17)
C8a—C4a—C5—C64.2 (2)C18—C13—C14—F1178.76 (13)
C4—C4a—C5—C6177.88 (12)C4—C13—C14—F13.8 (2)
O5—C5—C6—C1935.44 (19)C18—C13—C14—C151.7 (2)
C4a—C5—C6—C19147.35 (14)C4—C13—C14—C15175.76 (13)
O5—C5—C6—C2083.75 (16)F1—C14—C15—F20.7 (2)
C4a—C5—C6—C2093.45 (15)C13—C14—C15—F2178.85 (12)
O5—C5—C6—C7155.95 (13)F1—C14—C15—C16179.66 (13)
C4a—C5—C6—C726.84 (18)C13—C14—C15—C160.1 (2)
C19—C6—C7—C8176.00 (13)F2—C15—C16—C17179.59 (13)
C5—C6—C7—C854.69 (16)C14—C15—C16—C171.5 (2)
C20—C6—C7—C863.71 (16)C15—C16—C17—C181.4 (2)
C6—C7—C8—C8a51.46 (17)C16—C17—C18—C130.2 (2)
C5—C4a—C8a—N1168.68 (13)C14—C13—C18—C171.7 (2)
C4—C4a—C8a—N19.2 (2)C4—C13—C18—C17175.70 (14)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.915 (19)2.04 (2)2.9456 (15)168.0 (17)
Symmetry code: (i) x1, y, z.
(II) (±)-ethyl 4-(2,3-difluorophenyl)-2,6,6-trimethyl-5-oxo- 1,4,5,6,7,8-hexahydroquinoline-3-carboxylate top
Crystal data top
C21H23F2NO3Z = 2
Mr = 375.41F(000) = 396
Triclinic, P1Dx = 1.358 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.0677 (2) ÅCell parameters from 5288 reflections
b = 11.2167 (4) Åθ = 2.0–30.0°
c = 12.1844 (4) ŵ = 0.10 mm1
α = 83.6482 (15)°T = 160 K
β = 86.333 (2)°Plate, colourless
γ = 73.2481 (18)°0.22 × 0.17 × 0.05 mm
V = 918.74 (5) Å3
Data collection top
Nonius KappaCCD area-detector
diffractometer
3911 reflections with I > 2σ(I)
Radiation source: Nonius FR590 sealed tube generatorRint = 0.055
Horizontally mounted graphite crystal monochromatorθmax = 30.1°, θmin = 3.1°
Detector resolution: 9 pixels mm-1h = 09
ϕ and ω scans with κ offsetsk = 1415
25434 measured reflectionsl = 1617
5368 independent reflections
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)] = 0.052Hydrogen site location: geom & difmap
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0643P)2 + 0.1979P]
where P = (Fo2 + 2Fc2)/3
5366 reflections(Δ/σ)max = 0.001
252 parametersΔρmax = 0.31 e Å3
0 restraintsΔρmin = 0.23 e Å3
Crystal data top
C21H23F2NO3γ = 73.2481 (18)°
Mr = 375.41V = 918.74 (5) Å3
Triclinic, P1Z = 2
a = 7.0677 (2) ÅMo Kα radiation
b = 11.2167 (4) ŵ = 0.10 mm1
c = 12.1844 (4) ÅT = 160 K
α = 83.6482 (15)°0.22 × 0.17 × 0.05 mm
β = 86.333 (2)°
Data collection top
Nonius KappaCCD area-detector
diffractometer
3911 reflections with I > 2σ(I)
25434 measured reflectionsRint = 0.055
5368 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0520 restraints
wR(F2) = 0.143H atoms treated by a mixture of independent and constrained refinement
S = 1.04Δρmax = 0.31 e Å3
5366 reflectionsΔρmin = 0.23 e Å3
252 parameters
Special details top

Experimental. Solvent used: EtOH Cooling Device: Oxford Cryosystems Cryostream 700 Crystal mount: glued on a glass fibre Mosaicity (°.): 0.465 (2) Frames collected: 441 Seconds exposure per frame: 80 Degrees rotation per frame: 2.0 Crystal-Detector distance (mm): 35.0

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
xyzUiso*/Ueq
F10.59458 (13)0.74050 (9)0.26922 (9)0.0500 (3)
F20.68396 (19)0.54270 (11)0.15493 (12)0.0746 (4)
O50.54219 (14)1.01966 (10)0.21033 (9)0.0376 (3)
O101.09813 (17)0.73249 (11)0.59527 (9)0.0425 (3)
O110.85140 (14)0.70866 (9)0.50152 (8)0.0320 (2)
N11.18550 (16)0.97819 (11)0.31155 (10)0.0285 (3)
H11.303 (3)0.9988 (17)0.2959 (15)0.048 (5)*
C21.17182 (18)0.89818 (12)0.40453 (11)0.0253 (3)
C31.02122 (17)0.84446 (11)0.41586 (10)0.0233 (3)
C40.87715 (17)0.86372 (11)0.32331 (10)0.0227 (3)
H40.74160.87480.35770.027*
C4a0.87535 (17)0.98137 (11)0.24768 (10)0.0229 (3)
C50.69726 (18)1.04836 (12)0.19006 (11)0.0251 (3)
C60.69726 (19)1.16080 (12)0.10602 (11)0.0260 (3)
C70.90844 (19)1.16331 (13)0.07057 (11)0.0284 (3)
H710.96441.09830.01930.034*
H720.90341.24550.02980.034*
C81.0446 (2)1.14116 (13)0.16683 (12)0.0299 (3)
H811.18231.12970.13830.036*
H821.00711.21540.20920.036*
C8a1.03296 (18)1.02829 (12)0.24159 (11)0.0248 (3)
C91.33175 (19)0.88392 (14)0.48450 (12)0.0316 (3)
H911.29900.84210.55500.047*
H921.34280.96670.49620.047*
H931.45780.83370.45440.047*
C100.99982 (19)0.75944 (12)0.51373 (11)0.0270 (3)
C120.8200 (2)0.61824 (16)0.59061 (13)0.0400 (4)
H1210.76800.66060.65790.048*
H1220.94640.55420.60800.048*
C130.6750 (2)0.55821 (16)0.55373 (15)0.0460 (4)
H1310.72700.51770.48650.069*
H1320.54950.62210.53840.069*
H1330.65340.49550.61210.069*
C140.92645 (19)0.74954 (12)0.25832 (10)0.0261 (3)
C150.7836 (2)0.69489 (13)0.23440 (13)0.0351 (3)
C160.8315 (3)0.59033 (15)0.17584 (14)0.0461 (4)
C171.0211 (3)0.53591 (14)0.14110 (13)0.0463 (4)
H171.05220.46350.10210.056*
C181.1666 (3)0.58836 (14)0.16395 (13)0.0404 (4)
H181.29950.55200.14030.049*
C191.1203 (2)0.69377 (13)0.22123 (11)0.0314 (3)
H191.22230.72900.23570.038*
C200.5862 (2)1.15390 (15)0.00419 (12)0.0377 (3)
H2010.58601.22560.04970.057*
H2020.44971.15560.02610.057*
H2030.65171.07610.02900.057*
C210.5874 (2)1.27843 (14)0.16208 (14)0.0395 (4)
H2110.65871.28300.22720.059*
H2120.45351.27470.18480.059*
H2130.57991.35270.11010.059*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
F10.0364 (5)0.0465 (6)0.0750 (7)0.0210 (4)0.0114 (5)0.0090 (5)
F20.0854 (8)0.0519 (7)0.1039 (10)0.0365 (6)0.0372 (7)0.0172 (6)
O50.0239 (5)0.0422 (6)0.0465 (6)0.0149 (4)0.0064 (4)0.0138 (5)
O100.0532 (7)0.0483 (6)0.0313 (6)0.0232 (5)0.0158 (5)0.0058 (5)
O110.0307 (5)0.0383 (6)0.0289 (5)0.0162 (4)0.0038 (4)0.0075 (4)
N10.0213 (5)0.0313 (6)0.0351 (6)0.0118 (4)0.0019 (4)0.0006 (5)
C20.0213 (6)0.0248 (6)0.0293 (7)0.0045 (5)0.0005 (5)0.0061 (5)
C30.0211 (6)0.0233 (6)0.0253 (6)0.0053 (5)0.0010 (5)0.0038 (5)
C40.0209 (6)0.0232 (6)0.0254 (6)0.0083 (5)0.0017 (5)0.0018 (5)
C4a0.0226 (6)0.0208 (6)0.0258 (6)0.0076 (5)0.0011 (5)0.0023 (5)
C50.0232 (6)0.0246 (6)0.0281 (7)0.0080 (5)0.0006 (5)0.0026 (5)
C60.0261 (6)0.0235 (6)0.0287 (7)0.0082 (5)0.0023 (5)0.0008 (5)
C70.0296 (6)0.0269 (6)0.0298 (7)0.0114 (5)0.0011 (5)0.0009 (5)
C80.0266 (6)0.0284 (7)0.0373 (8)0.0134 (5)0.0005 (5)0.0011 (6)
C8a0.0220 (6)0.0239 (6)0.0286 (6)0.0071 (5)0.0003 (5)0.0029 (5)
C90.0251 (6)0.0350 (7)0.0362 (8)0.0087 (5)0.0061 (5)0.0058 (6)
C100.0269 (6)0.0276 (6)0.0264 (7)0.0067 (5)0.0018 (5)0.0040 (5)
C120.0437 (8)0.0454 (9)0.0322 (8)0.0203 (7)0.0010 (6)0.0107 (7)
C130.0437 (9)0.0397 (9)0.0551 (10)0.0179 (7)0.0058 (7)0.0126 (7)
C140.0343 (7)0.0220 (6)0.0228 (6)0.0099 (5)0.0057 (5)0.0027 (5)
C150.0372 (8)0.0305 (7)0.0401 (8)0.0125 (6)0.0106 (6)0.0009 (6)
C160.0676 (11)0.0325 (8)0.0470 (9)0.0245 (8)0.0247 (8)0.0002 (7)
C170.0788 (12)0.0257 (7)0.0329 (8)0.0091 (8)0.0140 (8)0.0048 (6)
C180.0574 (10)0.0290 (7)0.0296 (7)0.0045 (7)0.0008 (7)0.0023 (6)
C190.0402 (8)0.0266 (7)0.0265 (7)0.0087 (6)0.0000 (6)0.0006 (5)
C200.0384 (8)0.0443 (9)0.0340 (8)0.0194 (7)0.0088 (6)0.0061 (6)
C210.0367 (8)0.0273 (7)0.0519 (9)0.0054 (6)0.0039 (7)0.0057 (6)
Geometric parameters (Å, º) top
F1—C151.3446 (18)C8—H810.9900
F2—C161.3505 (18)C8—H820.9900
O5—C51.2316 (15)C9—H910.9800
O10—C101.2092 (16)C9—H920.9800
O11—C101.3528 (16)C9—H930.9800
O11—C121.4531 (17)C12—C131.493 (2)
N1—C8a1.3664 (17)C12—H1210.9900
N1—C21.3819 (17)C12—H1220.9900
N1—H10.925 (19)C13—H1310.9800
C2—C31.3592 (17)C13—H1320.9800
C2—C91.5016 (18)C13—H1330.9800
C3—C101.4706 (18)C14—C151.3834 (19)
C3—C41.5236 (17)C14—C191.4005 (19)
C4—C4a1.5210 (17)C15—C161.387 (2)
C4—C141.5234 (18)C16—C171.363 (3)
C4—H41.0000C17—C181.379 (2)
C4a—C8a1.3572 (17)C17—H170.9500
C4a—C51.4467 (18)C18—C191.387 (2)
C5—C61.5341 (17)C18—H180.9500
C6—C201.5305 (19)C19—H190.9500
C6—C211.533 (2)C20—H2010.9800
C6—C71.5344 (18)C20—H2020.9800
C7—C81.5182 (19)C20—H2030.9800
C7—H710.9900C21—H2110.9800
C7—H720.9900C21—H2120.9800
C8—C8a1.4949 (18)C21—H2130.9800
C10—O11—C12116.25 (11)H91—C9—H93109.5
C8a—N1—C2122.71 (11)H92—C9—H93109.5
C8a—N1—H1118.5 (11)O10—C10—O11121.63 (12)
C2—N1—H1118.8 (11)O10—C10—C3127.76 (12)
N1—C2—C3119.50 (12)O11—C10—C3110.59 (11)
N1—C2—C9112.95 (11)O11—C12—C13107.98 (12)
C3—C2—C9127.53 (12)O11—C12—H121110.1
C2—C3—C10121.43 (12)C13—C12—H121110.1
C2—C3—C4120.62 (11)O11—C12—H122110.1
C10—C3—C4117.82 (11)C13—C12—H122110.1
C4a—C4—C14111.06 (10)H121—C12—H122108.4
C3—C4—C4a110.81 (10)C12—C13—H131109.5
C14—C4—C3110.86 (10)C12—C13—H132109.5
C4a—C4—H4108.0H131—C13—H132109.5
C14—C4—H4108.0C12—C13—H133109.5
C3—C4—H4108.0H131—C13—H133109.5
C8a—C4a—C5120.46 (11)H132—C13—H133109.5
C4—C4a—C8a120.26 (11)C15—C14—C19116.80 (13)
C5—C4a—C4119.05 (10)C15—C14—C4121.94 (12)
O5—C5—C4a121.04 (11)C19—C14—C4121.26 (11)
O5—C5—C6118.95 (11)F1—C15—C14120.75 (13)
C4a—C5—C6119.96 (11)F1—C15—C16118.11 (13)
C20—C6—C21109.44 (12)C14—C15—C16121.13 (15)
C20—C6—C5109.26 (11)F2—C16—C17120.59 (15)
C21—C6—C5106.78 (11)F2—C16—C15117.76 (17)
C20—C6—C7109.26 (11)C17—C16—C15121.64 (15)
C21—C6—C7110.65 (11)C16—C17—C18118.46 (14)
C5—C6—C7111.41 (10)C16—C17—H17120.8
C8—C7—C6113.37 (11)C18—C17—H17120.8
C8—C7—H71108.9C17—C18—C19120.49 (16)
C6—C7—H71108.9C17—C18—H18119.8
C8—C7—H72108.9C19—C18—H18119.8
C6—C7—H72108.9C18—C19—C14121.49 (14)
H71—C7—H72107.7C18—C19—H19119.3
C8a—C8—C7111.16 (11)C14—C19—H19119.3
C8a—C8—H81109.4C6—C20—H201109.5
C7—C8—H81109.4C6—C20—H202109.5
C8a—C8—H82109.4H201—C20—H202109.5
C7—C8—H82109.4C6—C20—H203109.5
H81—C8—H82108.0H201—C20—H203109.5
C4a—C8a—N1120.28 (12)H202—C20—H203109.5
C4a—C8a—C8123.35 (11)C6—C21—H211109.5
N1—C8a—C8116.19 (11)C6—C21—H212109.5
C2—C9—H91109.5H211—C21—H212109.5
C2—C9—H92109.5C6—C21—H213109.5
H91—C9—H92109.5H211—C21—H213109.5
C2—C9—H93109.5H212—C21—H213109.5
C8a—N1—C2—C314.89 (19)C4—C4a—C8a—C8178.14 (11)
C8a—N1—C2—C9163.86 (12)C2—N1—C8a—C4a13.8 (2)
N1—C2—C3—C10179.55 (11)C2—N1—C8a—C8161.54 (12)
C9—C2—C3—C101.0 (2)C7—C8—C8a—C4a22.91 (18)
N1—C2—C3—C44.71 (18)C7—C8—C8a—N1161.89 (12)
C9—C2—C3—C4176.74 (12)C12—O11—C10—O101.29 (19)
C2—C3—C4—C4a22.06 (16)C12—O11—C10—C3177.37 (12)
C10—C3—C4—C4a162.05 (11)C2—C3—C10—O104.4 (2)
C2—C3—C4—C14101.74 (13)C4—C3—C10—O10179.70 (13)
C10—C3—C4—C1474.16 (14)C2—C3—C10—O11174.11 (11)
C14—C4—C4a—C8a100.53 (14)C4—C3—C10—O111.74 (16)
C3—C4—C4a—C8a23.14 (16)C10—O11—C12—C13170.78 (12)
C14—C4—C4a—C584.85 (14)C4a—C4—C14—C15104.94 (14)
C3—C4—C4a—C5151.48 (11)C3—C4—C14—C15131.41 (13)
C8a—C4a—C5—O5166.69 (13)C4a—C4—C14—C1975.99 (14)
C4—C4a—C5—O57.92 (19)C3—C4—C14—C1947.66 (15)
C8a—C4a—C5—C610.50 (19)C19—C14—C15—F1178.36 (12)
C4—C4a—C5—C6174.89 (11)C4—C14—C15—F10.7 (2)
O5—C5—C6—C2045.38 (17)C19—C14—C15—C160.4 (2)
C4a—C5—C6—C20137.37 (13)C4—C14—C15—C16179.50 (13)
O5—C5—C6—C2172.89 (16)F1—C15—C16—F21.7 (2)
C4a—C5—C6—C21104.36 (14)C14—C15—C16—F2179.54 (14)
O5—C5—C6—C7166.19 (12)F1—C15—C16—C17177.66 (14)
C4a—C5—C6—C716.55 (17)C14—C15—C16—C171.1 (2)
C20—C6—C7—C8167.20 (11)F2—C16—C17—C18179.68 (14)
C21—C6—C7—C872.24 (14)C15—C16—C17—C181.0 (2)
C5—C6—C7—C846.38 (15)C16—C17—C18—C190.2 (2)
C6—C7—C8—C8a49.59 (15)C17—C18—C19—C140.5 (2)
C5—C4a—C8a—N1167.69 (12)C15—C14—C19—C180.4 (2)
C4—C4a—C8a—N16.86 (19)C4—C14—C19—C18178.71 (12)
C5—C4a—C8a—C87.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.925 (19)1.990 (19)2.8712 (14)158.8 (16)
Symmetry code: (i) x+1, y, z.

Experimental details

(I)(II)
Crystal data
Chemical formulaC20H21F2NO3C21H23F2NO3
Mr361.39375.41
Crystal system, space groupTriclinic, P1Triclinic, P1
Temperature (K)160160
a, b, c (Å)7.2055 (2), 9.6702 (4), 12.9606 (6)7.0677 (2), 11.2167 (4), 12.1844 (4)
α, β, γ (°)93.9639 (19), 92.624 (2), 107.904 (2)83.6482 (15), 86.333 (2), 73.2481 (18)
V3)855.15 (6)918.74 (5)
Z22
Radiation typeMo KαMo Kα
µ (mm1)0.110.10
Crystal size (mm)0.27 × 0.22 × 0.200.22 × 0.17 × 0.05
Data collection
DiffractometerNonius KappaCCD area-detector
diffractometer
Nonius KappaCCD area-detector
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
21670, 4980, 3409 25434, 5368, 3911
Rint0.0530.055
(sin θ/λ)max1)0.7040.705
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.053, 0.137, 1.05 0.052, 0.143, 1.04
No. of reflections49765366
No. of parameters243252
H-atom treatmentH atoms treated by a mixture of independent and constrained refinementH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.32, 0.270.31, 0.23

Computer programs: COLLECT (Nonius, 2000), DENZO-SMN (Otwinowski & Minor, 1997), DENZO-SMN and SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1994), SHELXL97 (Sheldrick, 1997), ORTEPII (Johnson, 1976), SHELXL97 and PLATON (Spek, 2003).

Selected geometric parameters (Å, º) for (I) top
O10—C101.2155 (17)C3—C101.470 (2)
O11—C101.3474 (16)C3—C41.5253 (19)
N1—C8a1.3651 (18)C4—C4a1.5234 (19)
N1—C21.3878 (18)C4a—C8a1.3570 (19)
C2—C31.3537 (19)
C8a—N1—C2122.11 (12)C4—C4a—C8a119.69 (12)
N1—C2—C3119.21 (13)C4a—C8a—N1120.38 (13)
N1—C2—C9113.94 (12)O10—C10—O11121.76 (13)
C3—C2—C9126.83 (13)O10—C10—C3126.97 (13)
C2—C3—C4120.62 (12)O11—C10—C3111.28 (12)
C3—C4—C4a109.74 (11)
Hydrogen-bond geometry (Å, º) for (I) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.915 (19)2.04 (2)2.9456 (15)168.0 (17)
Symmetry code: (i) x1, y, z.
Selected geometric parameters (Å, º) for (II) top
O10—C101.2092 (16)C3—C101.4706 (18)
O11—C101.3528 (16)C3—C41.5236 (17)
N1—C8a1.3664 (17)C4—C4a1.5210 (17)
N1—C21.3819 (17)C4a—C8a1.3572 (17)
C2—C31.3592 (17)
C8a—N1—C2122.71 (11)C4—C4a—C8a120.26 (11)
N1—C2—C3119.50 (12)C4a—C8a—N1120.28 (12)
N1—C2—C9112.95 (11)O10—C10—O11121.63 (12)
C3—C2—C9127.53 (12)O10—C10—C3127.76 (12)
C2—C3—C4120.62 (11)O11—C10—C3110.59 (11)
C3—C4—C4a110.81 (10)
Hydrogen-bond geometry (Å, º) for (II) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O5i0.925 (19)1.990 (19)2.8712 (14)158.8 (16)
Symmetry code: (i) x+1, y, z.
 

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