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The molecule of the title compound, C19H27NO3, is essentially planar, with all non-H atoms within 0.2 Å of the nine-membered indole plane, except for the three tert-butyl C atoms. The C5 pentyl chain is in an extended conformation, with three torsion angles of 179.95 (13), 179.65 (13) and −178.95 (15)° (the latter two angles include the C atoms of the C5 chain only). Three intramolecular C—H...O=C contacts are present (C...O < 3.05 Å and C—H...O > 115°), and an intermolecular C—H...O=C contact and π–π stacking complete the intermolecular interactions.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270103028154/gd1287sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270103028154/gd1287Isup2.hkl
Contains datablock I

CCDC reference: 233138

Comment top

The key biochemical roles played by the indole ring in nature ensure that this heterocyclic system continues to attract scrutiny from medicinal and synthetic chemists. It is a common motif for drug targets, and as such the development of new diversity-tolerant routes to this privileged biological scaffold continue to be of significant benefit (Gribble, 1996). It forms the basis of a wide variety of drugs, including the anti-inflammatory agent Indomethacin, Reserpine (exploited as a hypotensive agent) and Sumatriptan (used for the treatment of migraine). Historically, interest in indoles arose from the isolation and characterization of indole alkaloids, which, along with their semi-synthetic derivatives, have potent central nervous system activity. Many recent advances in indole synthesis have focused on metal-mediated procedures, with copper, palladium, tin, titanium and zirconium being the most prevalent (Sundberg, 1996: Gribble, 2000).

Recently, we reported a new approach for the synthesis of the indole scaffold exploiting a controlled organolithium addition to functionalized styrenes, with the C—C-bond formation reaction as the key synthetic step. A significant benefit of this strategy is that it can provide a direct route for the introduction of further structural diversity onto the ring system (Coleman & O'Shea, 2003), which may be of benefit for combinatorial library generations. Despite the prevalence of indole structures in the Cambridge Structural Database (Allen, 2002), there are no structures that contain the indolyl skeleton and atoms substituted at the 1- (C), 3- (C) and 5- (O) positions for direct comparison with (I). Many derivatives are present, though, which contain the tryptophan residue.

Pertinent bond lengths and angles for (I) are listed in Table 1 and the molecular structure is depicted in Fig. 1. The bond lengths and angles are as expected for indole systems (Fig. 1). Localization in the aromatic rings is discernible in (I), with bond lengths of 1.3481 (19) Å for C1A—C2A [the other NC4 ring C—C lengths are 1.4496 (19) and 1.4090 (18) Å], and with C—N distances of 1.4022 (16) and 1.4076 (18) Å: the C6 distances for the C13—C14 and C15—C16 bonds are 1.379 (2) and 1.386 (2) Å, respectively. In the C5 pentyl chain, the C—C bond lengths for atoms C1–C5 are in a narrow range from 1.509 (2) to 1.5195 (19) Å; the C2A—C1—C2 angle opens to 114.98 (12)°, and the remaining C—C—C angles along the chain are in the range 113.71 (12)–113.86 (12)°, indicating a slight opening up by 4° from the ideal 109.5° tetrahedral angle. The pentyl chain is in an extended conformation, with three torsion angles of 179.95 (13) (C2A—C1—C2—C3), 179.65 (13) (C1—C2—C3—C4) and −178.95 (15)° (C2—C3—C4—C5). Indeed, the C5 pentyl chain is at an angle of 4.41 (13)° to the NC4 ring, and the largest deviation of an atom from the C5 plane is 0.011 (1) Å for atom C3. In the tert-butyl ester group, the three C—C bond lengths lie between 1.511 (2) and 1.515 (2) Å, while the three O—C—C angles are 102.60 (12), 109.89 (12) and 108.92 (13)°, the lowest being that involving atom C8 atom, which is not involved in an intramolecular contact; the three tert-butyl C—C—C angles are in the range 109.58 (14)–113.28 (15)°.

The five- and six-membered rings are coplanar, with an interplanar angle of 1.74 (8)°. In (I), an essentially planar molecule, the largest deviations for non-H atoms from the indole plane are for the two atoms of the tert-butyl group [1.110 (3) Å for atom C10 and 1.402 (3) Å for atom C9]; all other atoms are within 0.2 Å of the nine-membered indole plane (apart from the three tert-butyl C atoms). The MeO group at atom C14 displays an O—C—C distortion, with O3—C14—C13/C15 angles of 115.60 (13) and 123.34 (13)° (transoid to C13 and the C5 chain), which has been commented on previously (Baggio et al., 2001; Gallagher et al., 2001; Wiedenfeld et al., 2003), especially the MeC—O—C—C torsion angle orientation with respect to the O—C—C angle.

A review of the Cambridge Structural Database, (Version 5.24 of July 2003; Allen, 2002) was undertaken for structures containing an aromatic MeO group (analysed for para-C6H4—O—CH3 with three-dimensional coordinates, R < 0.10 and not disordered). In the Fig. 2, 2299 structures are plotted along the x axis (12299), with both MeO—C—C angles plotted (between 100 and 140°, y axis) and correlated with their corresponding C—O—C—C angles. The overall trend is that when the C—O—C—C torsion angles (triangles) are ~0 or ~180°, corresponding to a nearly planar C—O—C—C fragment, the methoxy group usually exhibits a 5–10° difference between the two O—C—C angles; when the disposition of the C—O—C—C torsion angle tends towards 90° [mid-table on the x axis (abscissa)] for structures 1100–1300 and 60–120° on the y axis (ordinate), both O—C—C angles are usually ~120°. For structures 1–1100/1300–2299, the O—C—C angles differ from 120° as the C—O—C—C angle tends towards 0°/180°. The majority of para-anisole derivatives have a C—O—C—C angle close to planarity (<15° or >165°), with a significant difference in their O—C—C angles that can be attributed to steric and electronic effects. Two related examples have been reported by Weidenfeld et al. (2003).

There are three C—H···O=Cester intramolecular contacts present, involving atoms C9, C10 and C16 (with C···O distances < 3.050 (2) Å and C—H···O angles > 115°; Table 2). A direction-specific C15—H15···O1i contact about inversion centres generates a weakly bonded dimer, C15···O15i = 3.4812 (19) Å. These dimeric units stack through aryl π stacking interactions. The mean planes of the indole units in these ππ stacks lie within 3.54 Å of one another, and the separations of the aromatic ring centroids are 3.6843 (9) and 3.6846 (9) Å for Cg1···Cg1ii and Cg1···Cg2ii, respectively, [symmetry code: (ii) 1 − x,1 − y,1 − z; Cg1 and Cg2 are the centroids of the five- and six-membered rings; Fig. 3]. These interactions are 0.2 Å longer than, although similar in nature to, the ππ stacking in graphite, where the interplanar spacing is 3.35 Å (Wells, 1984). Examination of the structure with PLATON (Spek, 2002) showed that there were no solvent-accessible voids in the crystal lattice.

Experimental top

(4-Methoxy)-2-vinyl-phenyl)-carbamic acid tert-butyl ester (0.4 g, 1.6 mmol) and TMEDA (0.48 ml, 3.2 mmol) were dissolved in dry diethyl ether (25 ml) and cooled to 195 K under N2. n-BuLi (3.3 ml, 1.87 M in pentane, 6.4 mmol) was added dropwise via a syringe over a period of 30 min. The temperature was raised to 248 K and the mixture was stirred for 2 h, during which time an orange–red colour developed. The solution was cooled to 195 K, anhydrous dimethylformamide (1.5 ml, 20 mmol) was added and the solution warmed to room temperature. The diethyl ether was evaporated and replaced by tetrahydrofuran (THF, 25 ml), and the mixture was stirred at room temperature under N2 for 5 h. The THF was then evaporated, and the residue was extracted with diethyl ether (2 x 30 ml) and dried over sodium sulfate. The solvent was evaporated to give a dark-yellow oil. Flash chromatography eluting with hexane/diethyl ether (9:1) gave the product as a white solid (yield 0.40 g, 80%; m.p. 327–328 K). Colourless crystals were obtained by slow evaporation of an ethanol solution. IR (νCO cm−1): 1721 (KBr); 1H NMR (300 MHz, d6-DMSO): δ 0.88 (t, J = 7 Hz, 3H), 1.24–1.37 (m, 4H), 1.61 (s, 9H), 1.62–1.68 (m, 2H), 2.62 (t, J = 7.3 Hz, 2H), 3.80 (s, 3H), 6.93 (dd, J = 2.5 Hz, 8.9 Hz, 1H), 7.06 (d, J = 2.5 Hz, 1H), 7.38 (s, 1H), 7.90 (d, j = 8.9 Hz, 1H); 13C NMR (75 MHz, CDCl3): δ 14.2, 22.7, 25.1, 28.5, 29.0, 32.0 56.0, 83.2, 102.3, 112.6, 116.1, 125.3, 130.1, 133.2, 150.1, 155.9; EI—MS: m/z 317.3. HRMS: (M+H)+ 318.2080 found; C19H28NO3 requires 318.2069. Analysis calculated for C19H27NO3: C 71.89, H 8.57, N 4.41%; found: C 71.94, H 8.60, N 4.33%.

Refinement top

Compound (I) crystallized in the triclinic system; space group P1 was assumed and confirmed by the analysis. All H atoms were treated as riding atoms using the SHELXL97 defaults (for 294 K), the C—H distances ranging from 0.93 to 0.98 Å. The three largest peaks in the final difference map are in the vicinity of the C11 atom.

Computing details top

Data collection: XSCANS (Bruker, 1994); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97 and PREP8 (Ferguson, 1998).

Figures top
[Figure 1] Fig. 1. A view of (I), with the atomic numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
[Figure 2] Fig. 2. A graph of MeO—C—C angle differences plotted against their corresponding C—O—C—C torsion angle for 2299 [–C6H4—O—CH3] structures (x axis) (CSD; Version 5.24 of July 2003; Allens, 2002). The intersect of the O—C—C lines (\sim120°) correlates well with the C—O—C—C angles (triangles) between 60 and 120° (y axis).
[Figure 3] Fig. 3. A view of the overlay of the alternating indole rings in the ππ stacking arrangement.
5-Methoxy-3-pentyl-indole-1-carboxylic acid tert-butyl ester top
Crystal data top
C19H27NO3F(000) = 344
Mr = 317.42? #Insert any comments here.
Triclinic, P1Dx = 1.176 Mg m3
Hall symbol: -P 1Melting point: 328 K
a = 8.9414 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 8.9955 (6) ÅCell parameters from 63 reflections
c = 11.7433 (6) Åθ = 5.5–21.5°
α = 105.001 (4)°µ = 0.08 mm1
β = 93.265 (6)°T = 294 K
γ = 98.902 (6)°Block, colourless
V = 896.69 (10) Å30.52 × 0.20 × 0.15 mm
Z = 2
Data collection top
Bruker P4
diffractometer
Rint = 0.044
Radiation source: X-ray tubeθmax = 27.5°, θmin = 2.3°
Graphite monochromatorh = 111
ω scansk = 1111
4895 measured reflectionsl = 1515
4071 independent reflections4 standard reflections every 296 reflections
3004 reflections with I > 2σ(I) intensity decay: 1%
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)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.133H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0687P)2 + 0.12P]
where P = (Fo2 + 2Fc2)/3
4071 reflections(Δ/σ)max = 0.001
213 parametersΔρmax = 0.38 e Å3
0 restraintsΔρmin = 0.19 e Å3
Crystal data top
C19H27NO3γ = 98.902 (6)°
Mr = 317.42V = 896.69 (10) Å3
Triclinic, P1Z = 2
a = 8.9414 (6) ÅMo Kα radiation
b = 8.9955 (6) ŵ = 0.08 mm1
c = 11.7433 (6) ÅT = 294 K
α = 105.001 (4)°0.52 × 0.20 × 0.15 mm
β = 93.265 (6)°
Data collection top
Bruker P4
diffractometer
Rint = 0.044
4895 measured reflections4 standard reflections every 296 reflections
4071 independent reflections intensity decay: 1%
3004 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0480 restraints
wR(F2) = 0.133H-atom parameters constrained
S = 1.03Δρmax = 0.38 e Å3
4071 reflectionsΔρmin = 0.19 e Å3
213 parameters
Special details top

Experimental. ? #Insert any special details here.

Geometry. Specified hydrogen bonds (with e.s.d.'s except fixed and riding H) ##############################################################

# D H A D—H H···A D···A D—H···A symm publ # - - - — —– —– ——- —- —- C9 H9C O1 0.96 2.36 2.944 (2) 119 1_555 yes C10 H10A O1 0.96 2.46 3.033 (2) 118 1_555 yes C16 H16 O1 0.93 2.42 2.9356 (19) 115 1_555 yes C15 H15 O1 0.93 2.66 3.4812 (19) 148 2_566 yes

# Cg1 -> Cg1 [2666] 3.6843 (9) 0.02 3.537 3.537 # Cg1 -> Cg2 [2666] 3.6846 (9) 1.74 3.535 3.506

Planes data ###########

Least-squares planes (x,y,z in crystal coordinates) and deviations from them (* indicates atom used to define plane)

3.6371(0.0048)x + 7.3702(0.0031)y − 5.2849(0.0061)z = 1.0797(0.0030)

* 0.0098 (0.0009) C11 * −0.0041 (0.0009) C12 * −0.0056 (0.0010) C13 * 0.0097 (0.0010) C14 * −0.0040 (0.0010) C15 * −0.0058 (0.0010) C16 0.0509 (0.0020) N1 0.0290 (0.0028) C1 − 0.0234 (0.0035) C2 − 0.0145 (0.0041) C3 − 0.0584 (0.0048) C4 − 0.0241 (0.0056) C5

Rms deviation of fitted atoms = 0.0069

3.6059(0.0066)x + 7.4657(0.0062)y − 4.8000(0.0186)z = 1.3670(0.0090)

Angle to previous plane (with approximate e.s.d.) = 2.69 (12)

* 0.0039 (0.0008) C1 * 0.0034 (0.0011) C2 * −0.0112 (0.0013) C3 * −0.0034 (0.0011) C4 * 0.0073 (0.0009) C5 0.1074 (0.0052) N1 0.0037 (0.0037) C11 − 0.0483 (0.0026) C12 0.1202 (0.0043) C1A 0.0171 (0.0025) C2A

Rms deviation of fitted atoms = 0.0066

3.6084(0.0056)x + 7.3263(0.0036)y − 5.6001(0.0070)z = 0.8990(0.0049)

Angle to previous plane (with approximate e.s.d.) = 4.41 (13)

* −0.0008 (0.0008) C11 * 0.0032 (0.0008) C12 * −0.0020 (0.0008) N1 * 0.0041 (0.0008) C1A * −0.0045 (0.0008) C2A 0.0228 (0.0023) C6 0.1161 (0.0035) C7 0.2816 (0.0042) C8 1.3278 (0.0040) C9 − 1.1875 (0.0040) C10

Rms deviation of fitted atoms = 0.0032

3.6371(0.0048)x + 7.3702(0.0031)y − 5.2849(0.0061)z = 1.0797(0.0030)

Angle to previous plane (with approximate e.s.d.) = 1.74 (8)

* 0.0098 (0.0009) C11 * −0.0041 (0.0009) C12 * −0.0056 (0.0010) C13 * 0.0097 (0.0010) C14 * −0.0040 (0.0010) C15 * −0.0058 (0.0010) C16 0.0509 (0.0020) N1 0.0290 (0.0028) C1 − 0.0234 (0.0035) C2 − 0.0145 (0.0041) C3 − 0.0584 (0.0048) C4 − 0.0241 (0.0056) C5

Rms deviation of fitted atoms = 0.0069

3.6127(0.0036)x + 7.3602(0.0026)y − 5.4201(0.0034)z = 1.0181(0.0019)

Angle to previous plane (with approximate e.s.d.) = 0.74 (7)

* −0.0112 (0.0012) C11 * −0.0195 (0.0012) C12 * −0.0033 (0.0011) C13 * 0.0236 (0.0011) C14 * 0.0041 (0.0012) C15 * −0.0152 (0.0011) C16 * 0.0117 (0.0010) N1 * 0.0198 (0.0011) C1A * −0.0102 (0.0011) C2A −0.0014 (0.0021) C1 − 0.0714 (0.0024) C2 − 0.0619 (0.0029) C3 − 0.1233 (0.0033) C4 − 0.0883 (0.0039) C5 0.0582 (0.0018) O3 0.2998 (0.0028) C31

Rms deviation of fitted atoms = 0.0147

3.6059(0.0066)x + 7.4657(0.0062)y − 4.8000(0.0186)z = 1.3670(0.0090)

Angle to previous plane (with approximate e.s.d.) = 3.40 (12)

* 0.0039 (0.0008) C1 * 0.0034 (0.0011) C2 * −0.0112 (0.0013) C3 * −0.0034 (0.0011) C4 * 0.0073 (0.0009) C5 0.1074 (0.0052) N1 0.0037 (0.0037) C11 − 0.0483 (0.0026) C12 0.1202 (0.0043) C1A 0.0171 (0.0025) C2A

Rms deviation of fitted atoms = 0.0066

3.6127(0.0036)x + 7.3602(0.0026)y − 5.4201(0.0034)z = 1.0181(0.0019)

Angle to previous plane (with approximate e.s.d.) = 3.40 (12)

* −0.0112 (0.0012) C11 * −0.0195 (0.0012) C12 * −0.0033 (0.0011) C13 * 0.0236 (0.0011) C14 * 0.0041 (0.0012) C15 * −0.0152 (0.0011) C16 * 0.0117 (0.0010) N1 * 0.0198 (0.0011) C1A * −0.0102 (0.0011) C2A 0.0545 (0.0020) C6 0.0292 (0.0021) O1 0.1264 (0.0019) O2 0.1905 (0.0025) C7 0.3745 (0.0029) C8 1.4022 (0.0031) C9 − 1.1101 (0.0031) C10

Rms deviation of fitted atoms = 0.0147

3.5033(0.0090)x + 7.2958 (0.0065)y − 6.0122(0.0074)z = 0.5716(0.0072)

Angle to previous plane (with approximate e.s.d.) = 3.31 (12)

* 0.0011 (0.0009) C6 * −0.0006 (0.0005) O1 * −0.0010 (0.0008) O2 * 0.0004 (0.0003) C7 0.0065 (0.0027) N1

Rms deviation of fitted atoms = 0.0008

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.18351 (13)0.57366 (14)0.70809 (10)0.0684 (3)
O20.38764 (12)0.57975 (12)0.83449 (9)0.0532 (3)
O30.25088 (13)0.14710 (15)0.16841 (10)0.0673 (3)
N10.37007 (13)0.43482 (13)0.64714 (10)0.0455 (3)
C10.67422 (16)0.20729 (17)0.54329 (13)0.0497 (3)
C20.78016 (17)0.22680 (18)0.65333 (13)0.0518 (4)
C30.91578 (16)0.14424 (17)0.62986 (13)0.0490 (3)
C41.02222 (19)0.1643 (2)0.73931 (14)0.0601 (4)
C51.1590 (2)0.0842 (2)0.71528 (17)0.0708 (5)
C60.30237 (17)0.53506 (16)0.73022 (13)0.0487 (3)
C70.33847 (18)0.68863 (17)0.93773 (13)0.0538 (4)
C80.4711 (2)0.7175 (2)1.03145 (15)0.0727 (5)
C90.3223 (2)0.8400 (2)0.90901 (16)0.0707 (5)
C100.1937 (2)0.6085 (2)0.97243 (18)0.0834 (6)
C110.31383 (15)0.37091 (15)0.52707 (12)0.0430 (3)
C120.41810 (15)0.27905 (15)0.47337 (12)0.0422 (3)
C130.39325 (16)0.20448 (16)0.35256 (12)0.0479 (3)
C140.26678 (16)0.22288 (17)0.28829 (13)0.0498 (3)
C150.16288 (16)0.31148 (17)0.34293 (14)0.0521 (4)
C160.18555 (16)0.38630 (17)0.46320 (13)0.0496 (3)
C1A0.50678 (15)0.38203 (16)0.66506 (12)0.0461 (3)
C2A0.53905 (15)0.28740 (16)0.56361 (12)0.0442 (3)
C310.1372 (2)0.1832 (3)0.09702 (16)0.0829 (6)
H1A0.73180.24730.48670.060*
H1B0.63810.09650.50780.060*
H2A0.72310.18660.71000.062*
H2B0.81700.33740.68890.062*
H3A0.87880.03360.59470.059*
H3B0.97240.18400.57270.059*
H4A0.96610.12270.79590.072*
H4B1.05770.27500.77530.072*
H5A1.12510.02620.68250.106*
H5B1.22240.10260.78810.106*
H5C1.21600.12540.66010.106*
H8A0.48190.62101.04910.109*
H8B0.45290.79171.10200.109*
H8C0.56280.75811.00270.109*
H9A0.41520.88150.88230.106*
H9B0.30110.91390.97870.106*
H9C0.24030.82090.84780.106*
H10A0.11340.58910.90980.125*
H10B0.16610.67451.04350.125*
H10C0.20950.51110.98600.125*
H130.46080.14320.31580.058*
H150.07730.32050.29810.063*
H160.11620.44520.49980.060*
H1A10.56690.40860.73710.055*
H31A0.03890.14770.11880.124*
H31B0.14360.13220.01530.124*
H31C0.15170.29420.10830.124*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0610 (7)0.0837 (8)0.0620 (7)0.0416 (6)0.0078 (5)0.0050 (6)
O20.0623 (6)0.0568 (6)0.0441 (6)0.0302 (5)0.0112 (5)0.0074 (4)
O30.0660 (7)0.0849 (8)0.0471 (6)0.0251 (6)0.0019 (5)0.0055 (5)
N10.0458 (6)0.0501 (6)0.0436 (6)0.0199 (5)0.0085 (5)0.0105 (5)
C10.0482 (8)0.0571 (8)0.0477 (8)0.0238 (6)0.0096 (6)0.0117 (6)
C20.0517 (8)0.0563 (8)0.0503 (8)0.0230 (7)0.0076 (6)0.0112 (6)
C30.0461 (7)0.0553 (8)0.0498 (8)0.0188 (6)0.0075 (6)0.0151 (6)
C40.0589 (9)0.0654 (10)0.0558 (9)0.0215 (8)0.0004 (7)0.0111 (7)
C50.0579 (10)0.0847 (12)0.0751 (12)0.0270 (9)0.0025 (8)0.0247 (10)
C60.0517 (8)0.0485 (7)0.0497 (8)0.0200 (6)0.0118 (6)0.0121 (6)
C70.0653 (9)0.0509 (8)0.0485 (8)0.0256 (7)0.0179 (7)0.0076 (6)
C80.0936 (13)0.0735 (11)0.0513 (9)0.0357 (10)0.0048 (9)0.0059 (8)
C90.0901 (13)0.0541 (9)0.0706 (11)0.0311 (9)0.0104 (9)0.0106 (8)
C100.0931 (14)0.0822 (13)0.0733 (12)0.0135 (11)0.0406 (11)0.0124 (10)
C110.0431 (7)0.0436 (7)0.0457 (7)0.0125 (6)0.0103 (6)0.0138 (6)
C120.0402 (7)0.0444 (7)0.0460 (7)0.0126 (5)0.0096 (6)0.0150 (6)
C130.0468 (7)0.0511 (8)0.0480 (8)0.0159 (6)0.0108 (6)0.0116 (6)
C140.0486 (8)0.0531 (8)0.0464 (8)0.0089 (6)0.0043 (6)0.0116 (6)
C150.0433 (7)0.0580 (9)0.0561 (9)0.0125 (6)0.0001 (6)0.0164 (7)
C160.0438 (7)0.0523 (8)0.0564 (9)0.0170 (6)0.0103 (6)0.0148 (7)
C1A0.0462 (7)0.0516 (8)0.0450 (7)0.0194 (6)0.0078 (6)0.0143 (6)
C2A0.0445 (7)0.0471 (7)0.0453 (7)0.0160 (6)0.0096 (6)0.0144 (6)
C310.0771 (12)0.1139 (16)0.0556 (11)0.0325 (11)0.0078 (9)0.0129 (10)
Geometric parameters (Å, º) top
O1—C61.2029 (17)C2—H2A0.9700
O2—C61.3365 (18)C2—H2B0.9700
O2—C71.4838 (16)C3—H3A0.9700
O3—C141.3846 (18)C3—H3B0.9700
O3—C311.410 (2)C4—H4A0.9700
N1—C61.3829 (17)C4—H4B0.9700
N1—C111.4076 (18)C5—H5A0.9600
N1—C1A1.4022 (16)C5—H5B0.9600
C1—C2A1.5001 (18)C5—H5C0.9600
C1A—C2A1.3481 (19)C8—H8A0.9600
C1—C21.513 (2)C8—H8B0.9600
C2—C31.5195 (19)C8—H8C0.9600
C3—C41.509 (2)C9—H9A0.9600
C4—C51.517 (2)C9—H9B0.9600
C7—C81.515 (2)C9—H9C0.9600
C7—C91.511 (2)C10—H10A0.9600
C7—C101.512 (2)C10—H10B0.9600
C11—C121.4090 (18)C10—H10C0.9600
C11—C161.3792 (19)C13—H130.9300
C12—C2A1.4496 (19)C15—H150.9300
C12—C131.392 (2)C16—H160.9300
C13—C141.379 (2)C1A—H1A10.9300
C14—C151.394 (2)C31—H31A0.9600
C15—C161.386 (2)C31—H31B0.9600
C1—H1A0.9700C31—H31C0.9600
C1—H1B0.9700
C6—O2—C7120.16 (11)C4—C3—H3B108.8
C14—O3—C31116.97 (13)C2—C3—H3B108.8
C6—N1—C1A127.03 (12)H3A—C3—H3B107.7
C6—N1—C11125.12 (11)C3—C4—H4A108.8
C1A—N1—C11107.83 (11)C5—C4—H4A108.8
C2—C1—C2A114.98 (12)C3—C4—H4B108.8
C1—C2—C3113.71 (12)C5—C4—H4B108.8
C2—C3—C4113.86 (12)H4A—C4—H4B107.7
C3—C4—C5113.75 (14)C4—C5—H5A109.5
O1—C6—O2126.73 (13)C4—C5—H5B109.5
O1—C6—N1123.03 (14)H5A—C5—H5B109.5
O2—C6—N1110.24 (12)C4—C5—H5C109.5
O2—C7—C8102.60 (12)H5A—C5—H5C109.5
O2—C7—C9109.89 (12)H5B—C5—H5C109.5
O2—C7—C10108.92 (13)C7—C8—H8A109.5
C9—C7—C10113.28 (15)C7—C8—H8B109.5
C9—C7—C8109.58 (14)H8A—C8—H8B109.5
C8—C7—C10112.03 (15)C7—C8—H8C109.5
N1—C11—C12106.87 (11)H8A—C8—H8C109.5
N1—C11—C16131.59 (12)H8B—C8—H8C109.5
C12—C11—C16121.54 (13)C7—C9—H9A109.5
C11—C12—C2A107.87 (12)C7—C9—H9B109.5
C13—C12—C2A132.65 (12)H9A—C9—H9B109.5
O3—C14—C13115.60 (13)C7—C9—H9C109.5
O3—C14—C15123.34 (13)H9A—C9—H9C109.5
C11—C12—C13119.46 (13)H9B—C9—H9C109.5
C12—C13—C14118.92 (13)C7—C10—H10A109.5
C13—C14—C15121.05 (14)C7—C10—H10B109.5
C14—C15—C16120.83 (14)H10A—C10—H10B109.5
C11—C16—C15118.17 (13)C7—C10—H10C109.5
C2A—C1A—N1110.69 (12)H10A—C10—H10C109.5
C1A—C2A—C12106.73 (11)H10B—C10—H10C109.5
C1A—C2A—C1128.14 (13)C14—C13—H13120.5
C12—C2A—C1125.11 (12)C12—C13—H13120.5
C2A—C1—H1A108.5C16—C15—H15119.6
C2—C1—H1A108.5C14—C15—H15119.6
C2A—C1—H1B108.5C11—C16—H16120.9
C2—C1—H1B108.5C15—C16—H16120.9
H1A—C1—H1B107.5C2A—C1A—H1A1124.7
C1—C2—H2A108.8N1—C1A—H1A1124.7
C3—C2—H2A108.8O3—C31—H31A109.5
C1—C2—H2B108.8O3—C31—H31B109.5
C3—C2—H2B108.8H31A—C31—H31B109.5
H2A—C2—H2B107.7H31A—C31—H31C109.5
C4—C3—H3A108.8H31B—C31—H31C109.5
C2—C3—H3A108.8O3—C31—H31C109.5
C7—O2—C6—O10.3 (2)N1—C11—C12—C2A0.37 (15)
C31—O3—C14—C1510.4 (2)C11—C12—C13—C140.1 (2)
C11—N1—C6—O12.7 (2)C2A—C12—C13—C14177.98 (14)
C2—C1—C2A—C1A5.0 (2)C12—C13—C14—O3179.09 (12)
C2A—C1—C2—C3179.95 (13)C12—C13—C14—C151.5 (2)
C1—C2—C3—C4179.65 (13)C31—O3—C14—C13170.20 (15)
C2—C3—C4—C5178.95 (15)C13—C14—C15—C161.3 (2)
C7—O2—C6—N1179.68 (12)O3—C14—C15—C16179.26 (14)
C1A—N1—C6—O1179.17 (14)N1—C11—C16—C15177.91 (14)
C1A—N1—C6—O20.9 (2)C12—C11—C16—C151.5 (2)
C11—N1—C6—O2177.26 (12)C14—C15—C16—C110.2 (2)
C6—O2—C7—C959.04 (18)C6—N1—C1A—C2A179.01 (13)
C6—O2—C7—C1065.59 (18)C11—N1—C1A—C2A0.62 (16)
C6—O2—C7—C8175.53 (13)N1—C1A—C2A—C120.84 (16)
C6—N1—C11—C160.9 (2)N1—C1A—C2A—C1179.41 (13)
C1A—N1—C11—C16179.34 (14)C13—C12—C2A—C1A177.53 (15)
C6—N1—C11—C12178.56 (13)C11—C12—C2A—C1A0.75 (15)
C1A—N1—C11—C120.12 (15)C13—C12—C2A—C11.1 (2)
C16—C11—C12—C131.4 (2)C11—C12—C2A—C1179.38 (13)
N1—C11—C12—C13178.17 (12)C2—C1—C2A—C12176.70 (13)
C16—C11—C12—C2A179.90 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9C···O10.962.362.944 (2)119
C10—H10A···O10.962.463.033 (2)118
C16—H16···O10.932.422.9356 (19)115

Experimental details

Crystal data
Chemical formulaC19H27NO3
Mr317.42
Crystal system, space groupTriclinic, P1
Temperature (K)294
a, b, c (Å)8.9414 (6), 8.9955 (6), 11.7433 (6)
α, β, γ (°)105.001 (4), 93.265 (6), 98.902 (6)
V3)896.69 (10)
Z2
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.52 × 0.20 × 0.15
Data collection
DiffractometerBruker P4
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
4895, 4071, 3004
Rint0.044
(sin θ/λ)max1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.048, 0.133, 1.03
No. of reflections4071
No. of parameters213
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.38, 0.19

Computer programs: XSCANS (Bruker, 1994), XSCANS, SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), PLATON (Spek, 1998), SHELXL97 and PREP8 (Ferguson, 1998).

Selected geometric parameters (Å, º) top
O1—C61.2029 (17)N1—C111.4076 (18)
O2—C61.3365 (18)N1—C1A1.4022 (16)
O2—C71.4838 (16)C1—C2A1.5001 (18)
O3—C141.3846 (18)C1A—C2A1.3481 (19)
O3—C311.410 (2)C11—C121.4090 (18)
N1—C61.3829 (17)C12—C2A1.4496 (19)
C6—O2—C7120.16 (11)N1—C11—C16131.59 (12)
C14—O3—C31116.97 (13)C11—C12—C2A107.87 (12)
C6—N1—C1A127.03 (12)C13—C12—C2A132.65 (12)
C6—N1—C11125.12 (11)O3—C14—C13115.60 (13)
C1A—N1—C11107.83 (11)O3—C14—C15123.34 (13)
O1—C6—O2126.73 (13)C2A—C1A—N1110.69 (12)
O1—C6—N1123.03 (14)C1A—C2A—C12106.73 (11)
O2—C6—N1110.24 (12)C1A—C2A—C1128.14 (13)
N1—C11—C12106.87 (11)C12—C2A—C1125.11 (12)
C7—O2—C6—O10.3 (2)C11—N1—C6—O12.7 (2)
C31—O3—C14—C1510.4 (2)C2—C1—C2A—C1A5.0 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C9—H9C···O10.962.362.944 (2)119
C10—H10A···O10.962.463.033 (2)118
C16—H16···O10.932.422.9356 (19)115
 

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