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Crystals of the title compound, C26H31NO3, were obtained by the reaction of 1-naphthyl­methyl­amine with parthenolide. X-ray crystal structure determination reveals a stacked conformation between the cyclo­decane ring of the parthenol­ide moiety and the pendant naphthalene ring. The configuration of the new chiral center at C11 (the point of attachment of the naphthyl­methyl­amino side group) in the title compound is R, establishing the stereospecificity of the amination reaction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046983/hg2301sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046983/hg2301Isup2.hkl
Contains datablock I

CCDC reference: 667322

Key indicators

  • Single-crystal X-ray study
  • T = 90 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.034
  • wR factor = 0.080
  • Data-to-parameter ratio = 13.0

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.97 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C14 PLAT420_ALERT_2_C D-H Without Acceptor N1' - H1N' ... ? PLAT480_ALERT_4_C Long H...A H-Bond Reported H1N' .. O3 .. 2.71 Ang. PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 7
Alert level G REFLT03_ALERT_4_G Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF. From the CIF: _diffrn_reflns_theta_max 67.28 From the CIF: _reflns_number_total 3576 Count of symmetry unique reflns 2141 Completeness (_total/calc) 167.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1435 Fraction of Friedel pairs measured 0.670 Are heavy atom types Z>Si present no PLAT791_ALERT_1_G Confirm the Absolute Configuration of C4 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C11 = . R
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 6 ALERT level G = General alerts; check 5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 4 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

The title compound was synthesized as part of our ongoing drug discovery effort (Crooks et al., 2005), by the reaction of 1-naphthylmethylamine with parthenolide, and was shown to be a single diastereomer by NMR spectroscopic analysis. The crystal structure of the title compound was determined to obtain the configuration of the newly formed chiral center at C-11. An R absolute configuration was found.

The naphthalene ring of the amino side-chain is stacked against the cyclodecene ring of the parthenolide backbone. We believe that such a stacked structure is also consistent with the conformation of the title compound in the solution state (CDCl3), due to the unusual upfield resonance (4.66 p.p.m.) of the C-1 olefinic hydrogen as opposed to the usual value (ca 5.1–5.2 p.p.m.), in the NMR spectrum. This upfield shift is likely to be a result of anisotropic shielding of the C-1 hydrogen by the Pi cloud of the naphthalene ring. An intramolecular H-bonding is observed between N-1H and O3 (2.70 (17) A°, 3.07 (17) A°, 104.9 (12)°) of the carbonyl oxygen of the 5-membered lactone ring (Desiraju & Steiner, 1999). Other bond distances and angles within the molecule are quite regular (Allen et al., 1987).

Related literature top

For related literature, see: Allen et al. (1987); Crooks et al. (2005); Desiraju & Steiner (1999); Nasim et al. (2007); Parsons & Flack (2004).

Experimental top

The title compound was prepared acording to the previously reported procedure of Nasim et al. (2007). Crystals suitable for X-ray diffraction were obtained by slow evaporation of a chloroform/hexane solution at room temperature. The title compound was obtained as white crystals. 1H NMR (CDCl3, p.p.m.): δ 8.29 (d, 1H, J = 8.4 Hz), 7.83 (m, 2H), 7.57 (m, 4H), 4.66 (app. d, 1H, J = 10.2 Hz), 4.45 (d, 1H, J = 13.2 Hz) 4.10 (d, 1H, J = 13.2 Hz), 3.73 (t, 1H, J = 9.0 Hz), 3.24 (dd, 1H, J = 3.6, 12.6 Hz), 2.70 (dd, 1H, J = 12.6, 4.8 Hz), 2.51 (d, 1H, J = 9.0 Hz), 2.40–2.24 (m, 2H), 2.11–1.86 (m, 7H), 1.58 (s, 3H), 1.53–1.09 (m, 2H), 1.22 (s, 3H); 13C NMR (CDCl3, δ, p.p.m.): 176.7, 135.0, 134.3, 134.1, 132.1, 128.8, 128.2, 126.9, 126.0, 125.8, 125.3, 124.9, 124.6, 82.7, 66.4, 61.6, 51.9, 48.8, 45.8, 45.1, 40.7, 36.7, 30.2, 24.2, 17.4, 17.0.

Refinement top

H atoms were found in difference Fourier maps and those attached to carbon atoms were subsequently placed in idealized positions with constrained C—H distances of 0.98 Å (RCH3), 0.99 Å (R2CH2), 1.00 Å (R3CH) and 0.95 Å (CArH) with Uiso(H) values set to either 1.5Ueq (methyl) or 1.2Ueq of the attached C atom respectively. Since the NH hydrogen was clearly not planar, and there being no suitable riding model available, the coordinates of this H atom were refined but its Uiso was set to 1.5Ueq of the attached N atom. Since this crystal structure was known to be of an all light-atom chiral compound, Cu Kα X-rays were used so that the absolute configuration could be determined from the anomalous scattering of the oxygen atoms. The value of the Flack parameter (Flack, 1983) based on refinement with unmerged Friedel pairs, as determined by the Parsons' quotient method (Parsons & Flack, 2004) was x(u) = 0.13 (6).

Structure description top

The title compound was synthesized as part of our ongoing drug discovery effort (Crooks et al., 2005), by the reaction of 1-naphthylmethylamine with parthenolide, and was shown to be a single diastereomer by NMR spectroscopic analysis. The crystal structure of the title compound was determined to obtain the configuration of the newly formed chiral center at C-11. An R absolute configuration was found.

The naphthalene ring of the amino side-chain is stacked against the cyclodecene ring of the parthenolide backbone. We believe that such a stacked structure is also consistent with the conformation of the title compound in the solution state (CDCl3), due to the unusual upfield resonance (4.66 p.p.m.) of the C-1 olefinic hydrogen as opposed to the usual value (ca 5.1–5.2 p.p.m.), in the NMR spectrum. This upfield shift is likely to be a result of anisotropic shielding of the C-1 hydrogen by the Pi cloud of the naphthalene ring. An intramolecular H-bonding is observed between N-1H and O3 (2.70 (17) A°, 3.07 (17) A°, 104.9 (12)°) of the carbonyl oxygen of the 5-membered lactone ring (Desiraju & Steiner, 1999). Other bond distances and angles within the molecule are quite regular (Allen et al., 1987).

For related literature, see: Allen et al. (1987); Crooks et al. (2005); Desiraju & Steiner (1999); Nasim et al. (2007); Parsons & Flack (2004).

Computing details top

Data collection: APEX2 (Bruker, 2006); cell refinement: APEX2 (Bruker, 2006); data reduction: APEX2 (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL (Sheldrick, 1995); software used to prepare material for publication: SHELX97 (Sheldrick, 1997) and local procedures.

Figures top
[Figure 1] Fig. 1. A view of the asymmetric unit of the title compound, with displacement ellipsoids drawn at the 50% probability level; H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. A packing diagram, viewed down the a axis, hydrogen atoms have been omitted for clarity.
(11R)-13-(1-Naphthylmethylamino)-4,5-epoxy-11,13-dihydrocostunolide top
Crystal data top
C26H31NO3F(000) = 872
Mr = 405.52Dx = 1.294 Mg m3
Orthorhombic, P212121Cu Kα radiation, λ = 1.54178 Å
Hall symbol: P 2ac 2abCell parameters from 7441 reflections
a = 9.3842 (6) Åθ = 4.4–67.0°
b = 11.9025 (7) ŵ = 0.66 mm1
c = 18.6386 (13) ÅT = 90 K
V = 2081.8 (2) Å3Cut block, colourless
Z = 40.30 × 0.28 × 0.25 mm
Data collection top
Bruker X8 Proteum
diffractometer
3576 independent reflections
Radiation source: fine-focus rotating anode3503 reflections with I > 2σ(I)
Graded multilayer optics monochromatorRint = 0.034
Detector resolution: 18 pixels mm-1θmax = 67.3°, θmin = 4.4°
φ and ω scansh = 1110
Absorption correction: multi-scan
(SADABS in APEX2; Bruker, 2006)
k = 1414
Tmin = 0.826, Tmax = 0.852l = 2022
16527 measured reflections
Refinement top
Refinement on F2Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: fullH atoms treated by a mixture of independent and constrained refinement
R[F2 > 2σ(F2)] = 0.034 w = 1/[σ2(Fo2) + (0.0495P)2 + 0.31P]
where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.081(Δ/σ)max = 0.003
S = 1.11Δρmax = 0.28 e Å3
3576 reflectionsΔρmin = 0.33 e Å3
276 parametersExtinction correction: SHELXL97 (Sheldrick, 1997), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
0 restraintsExtinction coefficient: 0.0179 (7)
Primary atom site location: structure-invariant direct methodsAbsolute structure: Flack (1983), with 1490 Friedel pairs
Secondary atom site location: difference Fourier mapAbsolute structure parameter: 0.09 (5)
Crystal data top
C26H31NO3V = 2081.8 (2) Å3
Mr = 405.52Z = 4
Orthorhombic, P212121Cu Kα radiation
a = 9.3842 (6) ŵ = 0.66 mm1
b = 11.9025 (7) ÅT = 90 K
c = 18.6386 (13) Å0.30 × 0.28 × 0.25 mm
Data collection top
Bruker X8 Proteum
diffractometer
3576 independent reflections
Absorption correction: multi-scan
(SADABS in APEX2; Bruker, 2006)
3503 reflections with I > 2σ(I)
Tmin = 0.826, Tmax = 0.852Rint = 0.034
16527 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.034H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.081Δρmax = 0.28 e Å3
S = 1.11Δρmin = 0.33 e Å3
3576 reflectionsAbsolute structure: Flack (1983), with 1490 Friedel pairs
276 parametersAbsolute structure parameter: 0.09 (5)
0 restraints
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.

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 > 2σ(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
O10.73981 (11)0.85246 (8)0.94404 (6)0.0238 (2)
C10.81331 (16)0.62589 (13)0.78893 (8)0.0243 (3)
H1A0.73230.58060.79890.029*
O20.82549 (12)0.70644 (8)1.05639 (5)0.0245 (2)
C20.78375 (17)0.73806 (13)0.75591 (8)0.0261 (3)
H2A0.71510.72930.71600.031*
H2B0.87300.76980.73620.031*
O30.82066 (12)0.62291 (9)1.16246 (6)0.0294 (3)
C30.72219 (16)0.81826 (12)0.81239 (8)0.0241 (3)
H3A0.71750.89520.79230.029*
H3B0.62410.79460.82470.029*
C40.81190 (15)0.81904 (11)0.87883 (8)0.0203 (3)
C50.77511 (15)0.73593 (11)0.93375 (8)0.0205 (3)
H5A0.69210.68710.92120.025*
C60.87838 (15)0.68344 (12)0.98458 (8)0.0205 (3)
H6A0.97520.71690.97810.025*
C70.88646 (15)0.55483 (11)0.98032 (8)0.0199 (3)
H7A0.79020.52550.96700.024*
C80.99634 (16)0.50330 (13)0.92968 (8)0.0269 (3)
H8A1.02920.43160.95090.032*
H8B1.07960.55420.92770.032*
C90.94802 (17)0.48003 (12)0.85268 (8)0.0273 (3)
H9A1.01530.42620.83050.033*
H9B0.85320.44370.85420.033*
C100.93891 (16)0.58185 (12)0.80601 (8)0.0228 (3)
C110.91569 (15)0.52442 (12)1.05852 (8)0.0208 (3)
H11A1.02100.52561.06660.025*
C120.85036 (15)0.61909 (12)1.09992 (8)0.0219 (3)
C130.85856 (15)0.41104 (12)1.08246 (8)0.0217 (3)
H13A0.88960.35221.04830.026*
H13B0.89750.39231.13030.026*
C141.08003 (16)0.62865 (13)0.78347 (9)0.0280 (3)
H14A1.06500.69520.75340.042*
H14B1.13250.57180.75610.042*
H14C1.13510.64960.82610.042*
C150.95707 (16)0.86843 (12)0.87159 (8)0.0237 (3)
H15A1.00670.86380.91770.036*
H15B0.94910.94730.85700.036*
H15C1.01090.82670.83530.036*
N1'0.70323 (13)0.41347 (10)1.08575 (7)0.0206 (3)
H1N'0.6721 (18)0.4342 (14)1.1307 (11)0.028 (4)*
C2'0.63519 (15)0.30803 (12)1.06522 (8)0.0216 (3)
H2'A0.53470.30871.08140.026*
H2'B0.68410.24491.08950.026*
C3'0.63980 (15)0.28988 (11)0.98538 (8)0.0193 (3)
C4'0.56993 (14)0.36495 (11)0.93748 (8)0.0183 (3)
C5'0.48953 (15)0.45765 (11)0.96127 (8)0.0195 (3)
H5'A0.48020.47111.01130.023*
C6'0.42482 (15)0.52852 (12)0.91389 (8)0.0222 (3)
H6'A0.36940.58960.93110.027*
C7'0.43983 (15)0.51149 (13)0.83983 (8)0.0243 (3)
H7'A0.39690.56230.80700.029*
C8'0.51576 (15)0.42240 (12)0.81488 (8)0.0230 (3)
H8'A0.52510.41120.76460.028*
C9'0.58078 (14)0.34651 (11)0.86271 (8)0.0194 (3)
C10'0.65761 (15)0.25253 (13)0.83713 (8)0.0228 (3)
H10A0.66500.23970.78700.027*
C11'0.72056 (16)0.18102 (12)0.88348 (9)0.0252 (3)
H11B0.77100.11760.86590.030*
C12'0.71158 (15)0.20023 (12)0.95787 (8)0.0235 (3)
H12A0.75690.14920.98980.028*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0280 (5)0.0214 (5)0.0221 (5)0.0066 (4)0.0010 (4)0.0003 (4)
C10.0242 (7)0.0244 (7)0.0243 (7)0.0060 (6)0.0018 (6)0.0065 (6)
O20.0343 (6)0.0183 (5)0.0208 (5)0.0004 (4)0.0029 (4)0.0007 (4)
C20.0270 (8)0.0314 (8)0.0198 (7)0.0012 (7)0.0046 (6)0.0013 (6)
O30.0378 (6)0.0303 (5)0.0203 (5)0.0011 (5)0.0039 (5)0.0004 (4)
C30.0247 (8)0.0238 (7)0.0239 (7)0.0020 (6)0.0028 (6)0.0024 (6)
C40.0222 (7)0.0170 (6)0.0218 (7)0.0035 (5)0.0001 (6)0.0022 (6)
C50.0199 (6)0.0194 (7)0.0222 (7)0.0011 (6)0.0003 (6)0.0011 (5)
C60.0194 (7)0.0204 (7)0.0216 (7)0.0012 (5)0.0002 (6)0.0012 (6)
C70.0185 (7)0.0187 (6)0.0224 (8)0.0007 (5)0.0003 (6)0.0014 (5)
C80.0260 (7)0.0267 (7)0.0280 (8)0.0064 (6)0.0044 (6)0.0044 (6)
C90.0316 (8)0.0201 (7)0.0302 (8)0.0024 (6)0.0087 (7)0.0038 (6)
C100.0262 (8)0.0227 (7)0.0197 (7)0.0026 (6)0.0039 (6)0.0060 (6)
C110.0187 (6)0.0210 (7)0.0227 (7)0.0006 (6)0.0033 (6)0.0014 (6)
C120.0226 (7)0.0206 (7)0.0223 (8)0.0053 (6)0.0055 (6)0.0007 (6)
C130.0189 (7)0.0207 (6)0.0257 (7)0.0002 (5)0.0033 (6)0.0047 (6)
C140.0250 (7)0.0279 (7)0.0312 (8)0.0001 (6)0.0061 (7)0.0002 (7)
C150.0281 (8)0.0195 (6)0.0236 (7)0.0019 (6)0.0018 (6)0.0002 (6)
N1'0.0191 (6)0.0217 (6)0.0212 (6)0.0008 (5)0.0006 (5)0.0008 (5)
C2'0.0199 (7)0.0219 (7)0.0229 (7)0.0046 (6)0.0010 (6)0.0031 (6)
C3'0.0153 (7)0.0193 (6)0.0231 (7)0.0044 (5)0.0007 (6)0.0009 (5)
C4'0.0146 (6)0.0178 (6)0.0224 (7)0.0043 (5)0.0008 (5)0.0009 (6)
C5'0.0171 (6)0.0198 (7)0.0217 (7)0.0028 (5)0.0007 (5)0.0029 (5)
C6'0.0174 (7)0.0182 (6)0.0309 (8)0.0005 (5)0.0000 (6)0.0031 (6)
C7'0.0186 (7)0.0265 (7)0.0279 (7)0.0014 (6)0.0041 (6)0.0053 (6)
C8'0.0182 (7)0.0303 (7)0.0204 (7)0.0054 (6)0.0009 (6)0.0001 (6)
C9'0.0144 (6)0.0217 (7)0.0220 (7)0.0038 (5)0.0002 (5)0.0026 (5)
C10'0.0198 (7)0.0259 (7)0.0228 (7)0.0034 (6)0.0027 (6)0.0084 (6)
C11'0.0218 (7)0.0207 (7)0.0332 (8)0.0012 (6)0.0028 (6)0.0061 (6)
C12'0.0181 (7)0.0213 (7)0.0312 (8)0.0000 (6)0.0002 (6)0.0026 (6)
Geometric parameters (Å, º) top
O1—C51.4388 (16)C13—N1'1.4592 (19)
O1—C41.4467 (17)C13—H13A0.9900
C1—C101.329 (2)C13—H13B0.9900
C1—C21.496 (2)C14—H14A0.9800
C1—H1A0.9500C14—H14B0.9800
O2—C121.3393 (18)C14—H14C0.9800
O2—C61.4534 (17)C15—H15A0.9800
C2—C31.534 (2)C15—H15B0.9800
C2—H2A0.9900C15—H15C0.9800
C2—H2B0.9900N1'—C2'1.4591 (18)
O3—C121.1994 (18)N1'—H1N'0.92 (2)
C3—C41.497 (2)C2'—C3'1.504 (2)
C3—H3A0.9900C2'—H2'A0.9900
C3—H3B0.9900C2'—H2'B0.9900
C4—C51.465 (2)C3'—C12'1.362 (2)
C4—C151.490 (2)C3'—C4'1.423 (2)
C5—C61.492 (2)C4'—C5'1.408 (2)
C5—H5A1.0000C4'—C9'1.414 (2)
C6—C71.5348 (19)C5'—C6'1.364 (2)
C6—H6A1.0000C5'—H5'A0.9500
C7—C81.527 (2)C6'—C7'1.402 (2)
C7—C111.527 (2)C6'—H6'A0.9500
C7—H7A1.0000C7'—C8'1.360 (2)
C8—C91.530 (2)C7'—H7'A0.9500
C8—H8A0.9900C8'—C9'1.408 (2)
C8—H8B0.9900C8'—H8'A0.9500
C9—C101.494 (2)C9'—C10'1.414 (2)
C9—H9A0.9900C10'—C11'1.349 (2)
C9—H9B0.9900C10'—H10A0.9500
C10—C141.497 (2)C11'—C12'1.408 (2)
C11—C121.497 (2)C11'—H11B0.9500
C11—C131.5190 (19)C12'—H12A0.9500
C11—H11A1.0000
C5—O1—C461.01 (9)C7—C11—H11A108.5
C10—C1—C2127.96 (14)O3—C12—O2121.26 (14)
C10—C1—H1A116.0O3—C12—C11128.65 (14)
C2—C1—H1A116.0O2—C12—C11110.08 (12)
C12—O2—C6110.62 (11)N1'—C13—C11110.32 (12)
C1—C2—C3110.05 (12)N1'—C13—H13A109.6
C1—C2—H2A109.7C11—C13—H13A109.6
C3—C2—H2A109.7N1'—C13—H13B109.6
C1—C2—H2B109.7C11—C13—H13B109.6
C3—C2—H2B109.7H13A—C13—H13B108.1
H2A—C2—H2B108.2C10—C14—H14A109.5
C4—C3—C2111.08 (12)C10—C14—H14B109.5
C4—C3—H3A109.4H14A—C14—H14B109.5
C2—C3—H3A109.4C10—C14—H14C109.5
C4—C3—H3B109.4H14A—C14—H14C109.5
C2—C3—H3B109.4H14B—C14—H14C109.5
H3A—C3—H3B108.0C4—C15—H15A109.5
O1—C4—C559.23 (9)C4—C15—H15B109.5
O1—C4—C15113.28 (12)H15A—C15—H15B109.5
C5—C4—C15123.04 (13)C4—C15—H15C109.5
O1—C4—C3115.70 (12)H15A—C15—H15C109.5
C5—C4—C3116.19 (13)H15B—C15—H15C109.5
C15—C4—C3116.20 (13)C2'—N1'—C13114.15 (12)
O1—C5—C459.76 (9)C2'—N1'—H1N'109.3 (11)
O1—C5—C6117.93 (12)C13—N1'—H1N'111.1 (11)
C4—C5—C6124.99 (13)N1'—C2'—C3'111.73 (12)
O1—C5—H5A114.3N1'—C2'—H2'A109.3
C4—C5—H5A114.3C3'—C2'—H2'A109.3
C6—C5—H5A114.3N1'—C2'—H2'B109.3
O2—C6—C5106.50 (11)C3'—C2'—H2'B109.3
O2—C6—C7104.62 (11)H2'A—C2'—H2'B107.9
C5—C6—C7114.64 (12)C12'—C3'—C4'118.91 (13)
O2—C6—H6A110.3C12'—C3'—C2'119.94 (13)
C5—C6—H6A110.3C4'—C3'—C2'121.14 (12)
C7—C6—H6A110.3C5'—C4'—C9'118.05 (13)
C8—C7—C11111.95 (12)C5'—C4'—C3'122.77 (13)
C8—C7—C6117.78 (12)C9'—C4'—C3'119.18 (12)
C11—C7—C6101.30 (11)C6'—C5'—C4'121.28 (13)
C8—C7—H7A108.5C6'—C5'—H5'A119.4
C11—C7—H7A108.5C4'—C5'—H5'A119.4
C6—C7—H7A108.5C5'—C6'—C7'120.22 (13)
C7—C8—C9116.90 (13)C5'—C6'—H6'A119.9
C7—C8—H8A108.1C7'—C6'—H6'A119.9
C9—C8—H8A108.1C8'—C7'—C6'120.13 (14)
C7—C8—H8B108.1C8'—C7'—H7'A119.9
C9—C8—H8B108.1C6'—C7'—H7'A119.9
H8A—C8—H8B107.3C7'—C8'—C9'120.73 (14)
C10—C9—C8114.59 (13)C7'—C8'—H8'A119.6
C10—C9—H9A108.6C9'—C8'—H8'A119.6
C8—C9—H9A108.6C8'—C9'—C10'121.00 (13)
C10—C9—H9B108.6C8'—C9'—C4'119.54 (13)
C8—C9—H9B108.6C10'—C9'—C4'119.46 (13)
H9A—C9—H9B107.6C11'—C10'—C9'120.44 (13)
C1—C10—C9120.68 (14)C11'—C10'—H10A119.8
C1—C10—C14124.80 (14)C9'—C10'—H10A119.8
C9—C10—C14114.50 (13)C10'—C11'—C12'120.13 (13)
C12—C11—C13111.88 (12)C10'—C11'—H11B119.9
C12—C11—C7103.89 (11)C12'—C11'—H11B119.9
C13—C11—C7115.32 (12)C3'—C12'—C11'121.85 (14)
C12—C11—H11A108.5C3'—C12'—H12A119.1
C13—C11—H11A108.5C11'—C12'—H12A119.1
C10—C1—C2—C3106.01 (18)C6—O2—C12—O3176.63 (13)
C1—C2—C3—C450.10 (16)C6—O2—C12—C113.70 (16)
C5—O1—C4—C15115.77 (13)C13—C11—C12—O338.6 (2)
C5—O1—C4—C3106.47 (14)C7—C11—C12—O3163.59 (15)
C2—C3—C4—O1155.94 (12)C13—C11—C12—O2141.08 (12)
C2—C3—C4—C589.27 (15)C7—C11—C12—O216.04 (15)
C2—C3—C4—C1567.55 (16)C12—C11—C13—N1'48.63 (16)
C4—O1—C5—C6116.24 (15)C7—C11—C13—N1'69.81 (16)
C15—C4—C5—O199.28 (15)C11—C13—N1'—C2'144.82 (13)
C3—C4—C5—O1105.64 (13)C13—N1'—C2'—C3'74.63 (16)
O1—C4—C5—C6104.71 (15)N1'—C2'—C3'—C12'117.47 (15)
C15—C4—C5—C65.4 (2)N1'—C2'—C3'—C4'62.64 (17)
C3—C4—C5—C6149.66 (13)C12'—C3'—C4'—C5'177.91 (13)
C12—O2—C6—C5143.65 (12)C2'—C3'—C4'—C5'2.0 (2)
C12—O2—C6—C721.87 (15)C12'—C3'—C4'—C9'2.02 (19)
O1—C5—C6—O252.48 (16)C2'—C3'—C4'—C9'178.08 (12)
C4—C5—C6—O2123.53 (14)C9'—C4'—C5'—C6'0.60 (19)
O1—C5—C6—C7167.65 (12)C3'—C4'—C5'—C6'179.47 (13)
C4—C5—C6—C7121.30 (15)C4'—C5'—C6'—C7'1.3 (2)
O2—C6—C7—C8152.32 (12)C5'—C6'—C7'—C8'1.8 (2)
C5—C6—C7—C891.42 (16)C6'—C7'—C8'—C9'0.3 (2)
O2—C6—C7—C1129.90 (14)C7'—C8'—C9'—C10'178.80 (13)
C5—C6—C7—C11146.16 (12)C7'—C8'—C9'—C4'1.6 (2)
C11—C7—C8—C9152.93 (13)C5'—C4'—C9'—C8'2.07 (19)
C6—C7—C8—C990.25 (17)C3'—C4'—C9'—C8'177.99 (13)
C7—C8—C9—C1076.25 (17)C5'—C4'—C9'—C10'178.36 (12)
C2—C1—C10—C9166.76 (14)C3'—C4'—C9'—C10'1.57 (19)
C2—C1—C10—C1411.4 (2)C8'—C9'—C10'—C11'179.37 (14)
C8—C9—C10—C1105.11 (17)C4'—C9'—C10'—C11'0.2 (2)
C8—C9—C10—C1473.23 (16)C9'—C10'—C11'—C12'0.8 (2)
C8—C7—C11—C12153.82 (12)C4'—C3'—C12'—C11'1.1 (2)
C6—C7—C11—C1227.45 (14)C2'—C3'—C12'—C11'178.98 (13)
C8—C7—C11—C1383.38 (15)C10'—C11'—C12'—C3'0.3 (2)
C6—C7—C11—C13150.25 (12)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O30.92 (2)2.709 (17)3.0778 (17)104.9 (12)

Experimental details

Crystal data
Chemical formulaC26H31NO3
Mr405.52
Crystal system, space groupOrthorhombic, P212121
Temperature (K)90
a, b, c (Å)9.3842 (6), 11.9025 (7), 18.6386 (13)
V3)2081.8 (2)
Z4
Radiation typeCu Kα
µ (mm1)0.66
Crystal size (mm)0.30 × 0.28 × 0.25
Data collection
DiffractometerBruker X8 Proteum
Absorption correctionMulti-scan
(SADABS in APEX2; Bruker, 2006)
Tmin, Tmax0.826, 0.852
No. of measured, independent and
observed [I > 2σ(I)] reflections
16527, 3576, 3503
Rint0.034
(sin θ/λ)max1)0.598
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.034, 0.081, 1.11
No. of reflections3576
No. of parameters276
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.28, 0.33
Absolute structureFlack (1983), with 1490 Friedel pairs
Absolute structure parameter0.09 (5)

Computer programs: APEX2 (Bruker, 2006), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), XP in SHELXTL (Sheldrick, 1995), SHELX97 (Sheldrick, 1997) and local procedures.

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1'—H1N'···O30.92 (2)2.709 (17)3.0778 (17)104.9 (12)
 

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