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The structure of the title compound [systematic name: (1R,4aS,7R,8S,E)-8-cinnamox­yloxy-7-isopropyl-4a-methyl­deca­hydro­naphthalene-1-carboxylic acid], C24H32O4, isolated from Verbesina turbacensis collected in Costa Rica, shows a eudesman sesquiterpene skeleton with normal values of bond lengths and angles. In the crystal structure, the hydr­oxy group is involved in the formation of inter­molecular O—H...O hydrogen bonds, which link the mol­ecules into zigzag chains extended along the [001] direction.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680702301X/cv2242sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680702301X/cv2242Isup2.hkl
Contains datablock I

CCDC reference: 651472

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.008 Å
  • R factor = 0.045
  • wR factor = 0.098
  • Data-to-parameter ratio = 6.7

checkCIF/PLATON results

No syntax errors found



Alert level A REFLT03_ALERT_1_A Reflection count < 85% complete (theta max?) From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _diffrn_reflns_theta_full 24.99 From the CIF: _reflns_number_total 1697 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 2195 Completeness (_total/calc) 77.31%
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data.
PLAT022_ALERT_3_A Ratio Unique / Expected Reflections too Low ....       0.77
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data.
PLAT029_ALERT_3_A _diffrn_measured_fraction_theta_full Low .......       0.77
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data.

Alert level B PLAT027_ALERT_3_B _diffrn_reflns_theta_full (too) Low ............ 24.99 Deg.
Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 6.71 PLAT241_ALERT_2_C Check High Ueq as Compared to Neighbors for C9 PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 7
Alert level G REFLT03_ALERT_1_G ALERT: Expected hkl max differ from CIF values From the CIF: _diffrn_reflns_theta_max 24.99 From the CIF: _reflns_number_total 1697 From the CIF: _diffrn_reflns_limit_ max hkl 10. 20. 10. From the CIF: _diffrn_reflns_limit_ min hkl -3. -3. -3. TEST1: Expected hkl limits for theta max Calculated maximum hkl 16. 20. 10. Calculated minimum hkl -16. -20. -10.
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data.
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           24.99
           From the CIF: _reflns_number_total               1697
           Count of symmetry unique reflns         2195
           Completeness (_total/calc)             77.31%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         0
           Fraction of Friedel pairs measured     0.000
           Are heavy atom types Z>Si present         no
Author Response: The data collection was performed in 2000, and the Rigaku instrument used in that moment does not physically allow a full coverage of the high angle data.
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K
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     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10    = .          S

3 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 9 ALERT level G = General alerts; check 9 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 5 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Comment top

Sesquiterpene derivatives are natural products responsible for the anti-inflammatory activity of a variety of medicinal plants, mainly from the Asteraceae family (Castro et al., 2000; Amaro-Luis et al., 2002; Wagner et al., 2004; Stefani et al., 2006). In particular, from the Verbesina turbacensis plant, collected in Costa Rica, were isolated the sesquiterpenes 15 ol derivate and the 15 oic derivate (I). The title compound (I), was reported in its esther's form, extracted from the Verbesina eggersii collected in Ecuador (Bohlmann & Lonitz, 1978) and later from Verbesina turbacensis collected in Venezuela (Amaro-Luis et al., 2002). In the molecule, all bond lengths and angles are normal. The molecular structure of (I) (Fig. 1) shows that the A and B rings adopt the chair conformations [ΔC2(2–3)min = 1.7 (6), ΔC2(3–4)max = 2.6 (6), ΔCs(2)min = 1.1 (4), ΔCs(1)max = 2.3 (5)] for A and [ΔC2(6–7))min = 3.9 (6), ΔC2(5–6))max = 5.2 (6), ΔCs(7)min = 0.5 (5), ΔCs(6)max = 4.6 (5)] for B, respectively [Griffin, J. F., Duax, W. & Weeks, M. (1984). "Atlas of Steroid Structure". New York: Plenum Publishing corporation]. The crystal packing is stabilized by an O—H···O hydrogen bond (Table 1). In the extended zigzag chains which run along the [001] direction, as depicted in Fig. 2, molecules are related by 21 screw axis, and are linked by hydrogen bonds; each molecule acting as a donor of a hydrogen atom through the carboxylic acid group, and as an acceptor of a hydrogen atom through the oxygen atom in the esther group. Hydrophobic groups are located in the outer region of each chain.

Related literature top

The title compound was isolated in its esther and acid forms by Bohlmann & Lonitz (1978) and Amaro-Luis et al. (2002), respectively. For related literature concerning the sesquiterpene derivatives extracted from the Asteraceae family of plant, see: Castro et al. (2000); Amaro-Luis et al. (2002); Wagner et al. (2004); Stefani et al. (2006).

Experimental top

The title compound (II) was isolated from aerial parts of Verbesina turbacensis (Asteraceae) in San José, Costa Rica in 2000. Crystals of (II) suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution at room temperature. 1H NMR (400 MHz, DMSO-d6): δ 1.39 (H1a, m), 1.00 (H1b, m), 1.88 (H2a, m), 1.24 (H2b, m), 1.48 (H3a, m), 1.14 (H3b, m), 2.32 (H4, m), 1.55 (H5, dd), 5.42 (H6, dd), 1.14 (H7, m), 1.50 (H8a, m), 1.60 (H8b, m), 1.55 (H9a, m) 1.12 (H9b, m), 1.42 (H11, m), 1.00 (H12, d), 0.81 (H13, d), 1.24 (H14, s), 6.33 (H17, d), 7.62 (H18, d)7.50 (H20–24, m), 7.33 (H21–23, m), 7.33 (H22, m); 13C NMR (100 MHz, DMSO-d6): δ 44.1 (C1, t), 18.6 (C2, t), 29.8 (C3, t), 42.4 (C4, d), 50.4 (C5, d), 74.1 (C6, d), 51.0 (C7, d), 20.7 (C8, d), 44.4 (C9, t), 34.3(C10, s), 28.2 (C11, d), 22.3 (C12, q), 202, (C13, q), 20.6 (C14, q), 166.7 (C16, s), 118.6 (C17, d), 144.1 (C18, d), 134.7 (C19, s), 128.1 (C20–24, d), 128.6 (C21–23, d), 129.7 (C22, d).

Refinement top

All H atom attached to C atoms were positioned geometrically like idealized group and isotropic displacement parameters were set equal to 1.2 times Ueq(parent) or 1.5 Ueq(parent) (methyls). The hydroxy H atom was positioned geometrically [O—H 0.82 Å], and refined with Uiso(H)= 1.2Ueq(O). The absolute configuration was not established because of the absence of significant anomalous scatterers. 915 Friedel pairs were merged before the final refinement.

Structure description top

?

# Following replaced by publCIF - lun 23. abr 23:01:28 2007

The stucture of the title compound, (I), is shown below. Dimensions are available in the archived CIF.

For related literature, see [type here to add references to related ].

Computing details top

Data collection: MSC/AFC Difractometer Control Software (Molecular Structure Corporation, 1993); cell refinement: MSC/AFC Difractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: PLATON (Spek, 2003).

Figures top
[Figure 1] Fig. 1. View of (I) with the atom labelling scheme. Displacement ellipsoids are drawn at the 30% probability level and H atoms are shown with an arbitrary radius.
[Figure 2] Fig. 2. A partial packing view of (I). Hydrogen bonds are marked with green, dashed lines. H atoms not involved in hydrogen bonding have been omitted for clarity.
(1R,4aS,7R,8S,E)-8-cinnamoxyloxy-7-isopropyl-4a-methyldecahydronaphthalene- 1-carboxylic acid top
Crystal data top
C24H32O4F(000) = 832
Mr = 384.50Dx = 1.174 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71069 Å
Hall symbol: P 2ac 2abCell parameters from 20 reflections
a = 14.252 (3) Åθ = 1.8–24.8°
b = 17.312 (3) ŵ = 0.08 mm1
c = 8.820 (4) ÅT = 293 K
V = 2176.1 (11) Å3Rectangular, colourless
Z = 40.40 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC-7S
diffractometer
Rint = 0.025
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 1.9°
Graphite monochromatorh = 310
ω–2θ scansk = 320
3559 measured reflectionsl = 310
1697 independent reflections3 standard reflections every 150 reflections
1060 reflections with I > 2σ(I) intensity decay: none
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)] = 0.045Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.098H-atom parameters constrained
S = 1.01 w = 1/[σ2(Fo2) + (0.0389P)2 + 0.3391P]
where P = (Fo2 + 2Fc2)/3
1697 reflections(Δ/σ)max < 0.001
253 parametersΔρmax = 0.11 e Å3
0 restraintsΔρmin = 0.15 e Å3
Crystal data top
C24H32O4V = 2176.1 (11) Å3
Mr = 384.50Z = 4
Orthorhombic, P212121Mo Kα radiation
a = 14.252 (3) ŵ = 0.08 mm1
b = 17.312 (3) ÅT = 293 K
c = 8.820 (4) Å0.40 × 0.20 × 0.10 mm
Data collection top
Rigaku AFC-7S
diffractometer
Rint = 0.025
3559 measured reflections3 standard reflections every 150 reflections
1697 independent reflections intensity decay: none
1060 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0450 restraints
wR(F2) = 0.098H-atom parameters constrained
S = 1.01Δρmax = 0.11 e Å3
1697 reflectionsΔρmin = 0.15 e Å3
253 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.

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
O10.1910 (3)0.0954 (2)0.4197 (4)0.078 (1)
H10.21650.07790.49560.117*
O20.1115 (3)0.1614 (2)0.5900 (4)0.0927 (14)
O30.0645 (2)0.00138 (16)0.2568 (3)0.0465 (9)
O40.2036 (2)0.02560 (16)0.1437 (4)0.0560 (10)
C10.1312 (4)0.1924 (3)0.3740 (7)0.0755 (19)
H1A0.15080.22050.28430.091*
H1B0.18650.18350.43560.091*
C20.0636 (4)0.2423 (3)0.4624 (7)0.0770 (18)
H2A0.04880.21730.55800.092*
H2B0.09290.29150.48470.092*
C30.0262 (4)0.2557 (3)0.3736 (6)0.0727 (18)
H3A0.06960.28520.43540.087*
H3B0.01210.28590.28390.087*
C40.0734 (4)0.1798 (2)0.3256 (6)0.0545 (15)
H40.12200.19390.25210.065*
C50.0021 (4)0.1291 (2)0.2386 (6)0.0488 (13)
H50.01830.16380.15720.059*
C60.0416 (3)0.0607 (2)0.1502 (5)0.0435 (13)
H60.09860.07670.09640.052*
C70.0299 (3)0.0289 (3)0.0360 (5)0.0507 (13)
H70.04560.07160.03230.061*
C80.1198 (4)0.0090 (3)0.1220 (6)0.0691 (16)
H8A0.16670.00870.05020.083*
H8B0.10700.03310.19150.083*
C90.1592 (4)0.0771 (4)0.2109 (6)0.0789 (18)
H9A0.21460.05990.26540.095*
H9B0.17900.11650.13960.095*
C100.0909 (4)0.1135 (3)0.3245 (6)0.0573 (15)
C110.0080 (4)0.0369 (3)0.0645 (6)0.0602 (15)
H110.03420.07680.00210.072*
C120.0695 (4)0.0744 (3)0.1611 (6)0.093 (2)
H12A0.11910.09220.09620.139*
H12B0.04390.11730.21640.139*
H12C0.09400.03700.23110.139*
C130.0865 (4)0.0087 (3)0.1692 (5)0.0769 (17)
H13A0.10970.05120.22820.115*
H13B0.13670.01230.10930.115*
H13C0.06250.03050.23560.115*
C140.0817 (3)0.0609 (3)0.4648 (5)0.0715 (17)
H14A0.05560.01210.43510.107*
H14B0.14260.05290.50870.107*
H14C0.04130.08500.53790.107*
C150.1245 (4)0.1448 (3)0.4604 (7)0.0604 (15)
C160.1471 (4)0.0392 (3)0.2424 (6)0.0440 (13)
C170.1552 (3)0.0980 (2)0.3611 (5)0.0480 (13)
H170.10900.10190.43510.058*
C180.2278 (4)0.1457 (2)0.3642 (5)0.0501 (14)
H180.27420.13730.29180.060*
C190.2432 (4)0.2099 (2)0.4681 (6)0.0481 (13)
C200.1829 (4)0.2284 (3)0.5827 (6)0.0736 (17)
H200.13040.19770.60020.088*
C210.1989 (5)0.2928 (3)0.6737 (6)0.087 (2)
H210.15740.30480.75160.105*
C220.2754 (5)0.3382 (3)0.6487 (7)0.080 (2)
H220.28560.38150.70870.096*
C230.3363 (4)0.3203 (3)0.5370 (7)0.0721 (17)
H230.38850.35150.52090.086*
C240.3221 (4)0.2563 (3)0.4465 (6)0.0582 (15)
H240.36510.24420.37090.070*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.079 (3)0.081 (2)0.073 (3)0.030 (2)0.018 (2)0.011 (2)
O20.089 (3)0.125 (3)0.063 (2)0.037 (3)0.007 (3)0.015 (3)
O30.039 (2)0.0480 (17)0.0520 (19)0.0044 (18)0.0016 (19)0.0176 (17)
O40.048 (3)0.059 (2)0.061 (2)0.0099 (18)0.007 (2)0.0085 (19)
C10.068 (5)0.078 (4)0.081 (4)0.031 (4)0.019 (4)0.022 (3)
C20.080 (5)0.063 (3)0.088 (4)0.030 (3)0.023 (4)0.000 (4)
C30.081 (5)0.049 (3)0.089 (4)0.015 (3)0.013 (4)0.007 (3)
C40.061 (4)0.045 (3)0.057 (3)0.008 (3)0.006 (3)0.014 (3)
C50.043 (4)0.047 (3)0.056 (3)0.008 (3)0.001 (3)0.020 (3)
C60.035 (3)0.046 (3)0.049 (3)0.001 (2)0.006 (3)0.017 (3)
C70.037 (4)0.060 (3)0.055 (3)0.008 (3)0.013 (3)0.019 (3)
C80.040 (4)0.088 (4)0.079 (4)0.012 (3)0.014 (3)0.012 (4)
C90.044 (5)0.110 (5)0.083 (4)0.006 (4)0.001 (4)0.023 (4)
C100.035 (4)0.071 (3)0.065 (3)0.012 (3)0.004 (4)0.019 (3)
C110.063 (4)0.059 (3)0.058 (3)0.009 (3)0.010 (3)0.005 (3)
C120.093 (5)0.104 (4)0.081 (4)0.030 (4)0.029 (4)0.005 (4)
C130.079 (5)0.090 (4)0.062 (3)0.013 (4)0.001 (4)0.003 (3)
C140.065 (4)0.079 (3)0.070 (3)0.001 (3)0.019 (4)0.031 (3)
C150.056 (5)0.054 (3)0.071 (4)0.002 (3)0.001 (4)0.004 (3)
C160.034 (4)0.041 (3)0.057 (3)0.000 (3)0.008 (3)0.008 (3)
C170.048 (4)0.041 (3)0.055 (3)0.003 (3)0.001 (3)0.010 (3)
C180.059 (4)0.042 (3)0.049 (3)0.001 (3)0.006 (3)0.006 (3)
C190.055 (4)0.044 (3)0.045 (3)0.010 (3)0.016 (3)0.006 (3)
C200.092 (5)0.066 (3)0.063 (4)0.030 (3)0.013 (4)0.012 (3)
C210.112 (6)0.087 (4)0.062 (4)0.029 (4)0.018 (4)0.026 (4)
C220.112 (6)0.060 (3)0.068 (4)0.016 (4)0.020 (4)0.013 (4)
C230.077 (5)0.059 (3)0.080 (4)0.021 (3)0.028 (4)0.001 (4)
C240.059 (4)0.058 (3)0.058 (3)0.004 (3)0.012 (3)0.001 (3)
Geometric parameters (Å, º) top
O1—C151.326 (6)C9—H9A0.9700
O1—H10.8200C9—H9B0.9700
O2—C151.194 (6)C10—C141.542 (6)
O3—C161.353 (5)C11—C131.531 (6)
O3—C61.465 (4)C11—C121.539 (6)
O4—C161.209 (5)C11—H110.9800
C1—C21.510 (7)C12—H12A0.9600
C1—C101.545 (6)C12—H12B0.9600
C1—H1A0.9700C12—H12C0.9600
C1—H1B0.9700C13—H13A0.9600
C2—C31.519 (7)C13—H13B0.9600
C2—H2A0.9700C13—H13C0.9600
C2—H2B0.9700C14—H14A0.9600
C3—C41.535 (6)C14—H14B0.9600
C3—H3A0.9700C14—H14C0.9600
C3—H3B0.9700C16—C171.465 (6)
C4—C151.521 (7)C17—C181.324 (6)
C4—C51.546 (6)C17—H170.9300
C4—H40.9800C18—C191.457 (6)
C5—C61.526 (6)C18—H180.9300
C5—C101.550 (6)C19—C201.366 (6)
C5—H50.9800C19—C241.395 (6)
C6—C71.535 (6)C20—C211.393 (7)
C6—H60.9800C20—H200.9300
C7—C81.527 (6)C21—C221.361 (7)
C7—C111.542 (6)C21—H210.9300
C7—H70.9800C22—C231.349 (7)
C8—C91.523 (6)C22—H220.9300
C8—H8A0.9700C23—C241.381 (6)
C8—H8B0.9700C23—H230.9300
C9—C101.533 (7)C24—H240.9300
C15—O1—H1109.5C14—C10—C1109.0 (4)
C16—O3—C6119.2 (4)C9—C10—C5107.2 (4)
C2—C1—C10114.5 (5)C14—C10—C5115.0 (4)
C2—C1—H1A108.6C1—C10—C5107.5 (4)
C10—C1—H1A108.6C13—C11—C12109.0 (4)
C2—C1—H1B108.6C13—C11—C7111.5 (4)
C10—C1—H1B108.6C12—C11—C7112.2 (4)
H1A—C1—H1B107.6C13—C11—H11108.0
C1—C2—C3111.0 (5)C12—C11—H11108.0
C1—C2—H2A109.4C7—C11—H11108.0
C3—C2—H2A109.4C11—C12—H12A109.5
C1—C2—H2B109.4C11—C12—H12B109.5
C3—C2—H2B109.4H12A—C12—H12B109.5
H2A—C2—H2B108.0C11—C12—H12C109.5
C2—C3—C4112.3 (4)H12A—C12—H12C109.5
C2—C3—H3A109.1H12B—C12—H12C109.5
C4—C3—H3A109.1C11—C13—H13A109.5
C2—C3—H3B109.1C11—C13—H13B109.5
C4—C3—H3B109.1H13A—C13—H13B109.5
H3A—C3—H3B107.9C11—C13—H13C109.5
C15—C4—C3109.6 (5)H13A—C13—H13C109.5
C15—C4—C5118.5 (4)H13B—C13—H13C109.5
C3—C4—C5109.6 (4)C10—C14—H14A109.5
C15—C4—H4106.1C10—C14—H14B109.5
C3—C4—H4106.1H14A—C14—H14B109.5
C5—C4—H4106.1C10—C14—H14C109.5
C6—C5—C4116.8 (4)H14A—C14—H14C109.5
C6—C5—C10115.4 (4)H14B—C14—H14C109.5
C4—C5—C10114.7 (4)O2—C15—O1121.7 (5)
C6—C5—H5102.2O2—C15—C4125.4 (5)
C4—C5—H5102.2O1—C15—C4112.8 (5)
C10—C5—H5102.2O4—C16—O3123.5 (4)
O3—C6—C5108.9 (3)O4—C16—C17126.7 (5)
O3—C6—C7107.8 (3)O3—C16—C17109.8 (5)
C5—C6—C7111.6 (4)C18—C17—C16120.6 (5)
O3—C6—H6109.5C18—C17—H17119.7
C5—C6—H6109.5C16—C17—H17119.7
C7—C6—H6109.5C17—C18—C19127.3 (5)
C8—C7—C6108.2 (4)C17—C18—H18116.3
C8—C7—C11114.4 (4)C19—C18—H18116.3
C6—C7—C11114.2 (4)C20—C19—C24118.2 (5)
C8—C7—H7106.5C20—C19—C18123.3 (5)
C6—C7—H7106.5C24—C19—C18118.4 (5)
C11—C7—H7106.5C19—C20—C21120.7 (5)
C9—C8—C7113.0 (4)C19—C20—H20119.6
C9—C8—H8A109.0C21—C20—H20119.6
C7—C8—H8A109.0C22—C21—C20120.0 (6)
C9—C8—H8B109.0C22—C21—H21120.0
C7—C8—H8B109.0C20—C21—H21120.0
H8A—C8—H8B107.8C23—C22—C21120.1 (5)
C8—C9—C10114.8 (4)C23—C22—H22119.9
C8—C9—H9A108.6C21—C22—H22119.9
C10—C9—H9A108.6C22—C23—C24120.7 (6)
C8—C9—H9B108.6C22—C23—H23119.6
C10—C9—H9B108.6C24—C23—H23119.6
H9A—C9—H9B107.5C23—C24—C19120.2 (5)
C9—C10—C14109.6 (4)C23—C24—H24119.9
C9—C10—C1108.2 (5)C19—C24—H24119.9
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.760 (5)167
Symmetry code: (i) x+1/2, y, z+1/2.

Experimental details

Crystal data
Chemical formulaC24H32O4
Mr384.50
Crystal system, space groupOrthorhombic, P212121
Temperature (K)293
a, b, c (Å)14.252 (3), 17.312 (3), 8.820 (4)
V3)2176.1 (11)
Z4
Radiation typeMo Kα
µ (mm1)0.08
Crystal size (mm)0.40 × 0.20 × 0.10
Data collection
DiffractometerRigaku AFC-7S
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
3559, 1697, 1060
Rint0.025
(sin θ/λ)max1)0.594
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.098, 1.01
No. of reflections1697
No. of parameters253
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.11, 0.15

Computer programs: MSC/AFC Difractometer Control Software (Molecular Structure Corporation, 1993), MSC/AFC Difractometer Control Software, TEXSAN (Molecular Structure Corporation, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), DIAMOND (Brandenburg, 2001), PLATON (Spek, 2003).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O4i0.821.962.760 (5)167.1
Symmetry code: (i) x+1/2, y, z+1/2.
 

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