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The title compound [systematic name: (3S,5S,6R,7R,10S)-7-(2-hydr­oxy-2-prop­yl)-10-methyl-4-methyl­eneperhydro­naph­thal­ene-3,5,6-triol methanol solvate], C15H26O4·CH4O, is a new sesquiterpenoid which was isolated from Chrysanthemum indicum L. The mol­ecule contains two fused six-membered rings in chair conformations. There are methanol solvent mol­ecules in the crystal structure. All mol­ecules are linked by hydrogen bonds to give the three-dimensional structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806028522/jh2020sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806028522/jh2020Isup2.hkl
Contains datablock I

CCDC reference: 618974

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.004 Å
  • R factor = 0.033
  • wR factor = 0.068
  • Data-to-parameter ratio = 8.7

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ? PLAT731_ALERT_1_C Bond Calc 0.82(3), Rep 0.823(10) ...... 3.00 su-Ra O5 -H5O 1.555 1.555 PLAT735_ALERT_1_C D-H Calc 0.82(3), Rep 0.823(10) ...... 3.00 su-Ra O5 -H5O 1.555 1.555 PLAT736_ALERT_1_C H...A Calc 1.97(4), Rep 1.968(11) ...... 3.64 su-Ra H5O -O3 1.555 6.555
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 27.19 From the CIF: _reflns_number_total 1881 Count of symmetry unique reflns 1880 Completeness (_total/calc) 100.05% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1 Fraction of Friedel pairs measured 0.001 Are heavy atom types Z>Si present no 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 C3 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C5 = . S PLAT791_ALERT_1_G Confirm the Absolute Configuration of C6 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C7 = . R PLAT791_ALERT_1_G Confirm the Absolute Configuration of C10 = . S
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 8 ALERT level G = General alerts; check 11 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 0 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion 0 ALERT type 5 Informative message, check

Computing details top

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

(3S,5S,6R,7R,10S)-7-(2-hydroxy-2-propyl)-10-methyl-4- methyleneperhydronaphthalene-3,5,6-triol top
Crystal data top
C15H26O4·CH4OMelting point = 470–473 K
Mr = 302.40Mo Kα radiation, λ = 0.71073 Å
Hexagonal, P61Cell parameters from 28 reflections
a = 9.9315 (8) Åθ = 2.5–14.0°
c = 29.113 (5) ŵ = 0.09 mm1
V = 2486.8 (5) Å3T = 293 K
Z = 6Prism, colourless
F(000) = 9960.56 × 0.52 × 0.48 mm
Dx = 1.212 Mg m3
Data collection top
Siemens P4
diffractometer
Rint = 0.023
Radiation source: normal-focus sealed tubeθmax = 27.2°, θmin = 2.4°
Graphite monochromatorh = 012
ω scansk = 121
4581 measured reflectionsl = 037
1881 independent reflections3 standard reflections every 97 reflections
1495 reflections with I > 2σ(I) intensity decay: 2.3%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.033H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.068 w = 1/[σ2(Fo2) + (0.0336P)2]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max < 0.001
1881 reflectionsΔρmax = 0.13 e Å3
215 parametersΔρmin = 0.13 e Å3
6 restraintsExtinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0041 (6)
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
O10.1023 (2)0.1275 (2)0.00378 (6)0.0453 (4)
O20.35992 (18)0.27657 (18)0.07951 (5)0.0314 (4)
O30.55770 (19)0.44747 (19)0.02950 (5)0.0343 (4)
O40.7805 (2)0.7433 (2)0.01151 (6)0.0408 (4)
O50.2077 (3)0.4610 (3)0.06041 (7)0.0640 (6)
C10.4649 (3)0.0612 (3)0.06914 (8)0.0377 (6)
H1A0.54010.02840.07540.045*
H1B0.42370.07150.09830.045*
C20.3333 (3)0.0623 (3)0.04038 (9)0.0425 (6)
H2A0.37630.08140.01290.051*
H2B0.28130.15850.05770.051*
C30.2152 (3)0.0150 (3)0.02672 (8)0.0361 (6)
H30.15980.01690.05480.043*
C40.2887 (2)0.1497 (3)0.00746 (8)0.0296 (5)
C50.4257 (2)0.2718 (2)0.03506 (7)0.0259 (5)
C60.4999 (2)0.4388 (2)0.01634 (7)0.0262 (5)
H60.41860.46720.01490.031*
C70.6289 (2)0.5552 (2)0.04837 (7)0.0276 (5)
H70.57920.54930.07800.033*
C80.7500 (3)0.5065 (3)0.05744 (8)0.0345 (5)
H8A0.80440.51300.02910.041*
H8B0.82570.57710.07950.041*
C90.6740 (3)0.3409 (3)0.07602 (9)0.0347 (5)
H9A0.62920.33820.10590.042*
H9B0.75360.31280.08040.042*
C100.5467 (2)0.2195 (2)0.04493 (7)0.0291 (5)
C110.6998 (3)0.7257 (3)0.03157 (8)0.0331 (5)
C120.5747 (3)0.7659 (3)0.02096 (10)0.0457 (6)
H12A0.62230.87330.01230.055*
H12B0.51140.74790.04770.055*
H12C0.51110.70180.00380.055*
C130.8120 (3)0.8405 (3)0.06685 (9)0.0456 (6)
H13A0.89070.81450.07400.055*
H13B0.75600.83530.09430.055*
H13C0.86000.94390.05450.055*
C140.6205 (3)0.2028 (3)0.00014 (8)0.0384 (6)
H14A0.67920.15220.00670.046*
H14B0.68830.30400.01250.046*
H14C0.54000.14200.02160.046*
C150.2262 (3)0.1830 (3)0.02738 (9)0.0417 (6)
H15A0.26560.28580.03640.050*
H15B0.14250.10360.04310.050*
C160.1028 (4)0.4442 (5)0.02632 (11)0.0812 (11)
H16A0.08320.52950.02780.097*
H16B0.00720.34830.03080.097*
H16C0.14540.44330.00320.097*
H2O0.306 (2)0.317 (2)0.0763 (8)0.026 (6)*
H1O0.148 (3)0.125 (3)0.0270 (6)0.051 (9)*
H3O0.633 (2)0.5345 (17)0.0339 (9)0.047 (8)*
H4O0.8731 (14)0.777 (3)0.0070 (11)0.062 (10)*
H5O0.184 (5)0.491 (4)0.0838 (8)0.105 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0326 (10)0.0406 (10)0.0453 (10)0.0053 (8)0.0054 (8)0.0150 (8)
O20.0344 (9)0.0358 (9)0.0282 (9)0.0207 (8)0.0045 (7)0.0028 (7)
O30.0363 (9)0.0350 (10)0.0243 (8)0.0123 (8)0.0017 (7)0.0033 (7)
O40.0354 (11)0.0421 (10)0.0345 (9)0.0115 (9)0.0017 (8)0.0040 (8)
O50.0731 (14)0.1070 (18)0.0431 (11)0.0685 (14)0.0097 (11)0.0010 (12)
C10.0417 (14)0.0344 (13)0.0424 (14)0.0230 (11)0.0011 (11)0.0001 (11)
C20.0444 (14)0.0295 (13)0.0497 (15)0.0157 (12)0.0022 (13)0.0005 (12)
C30.0302 (13)0.0308 (12)0.0391 (13)0.0092 (11)0.0028 (11)0.0099 (10)
C40.0231 (11)0.0357 (12)0.0309 (11)0.0154 (10)0.0010 (9)0.0085 (10)
C50.0258 (11)0.0290 (11)0.0237 (10)0.0142 (9)0.0004 (9)0.0046 (9)
C60.0252 (11)0.0337 (12)0.0238 (10)0.0177 (10)0.0004 (9)0.0042 (9)
C70.0272 (11)0.0309 (12)0.0236 (10)0.0137 (10)0.0001 (9)0.0028 (9)
C80.0289 (12)0.0352 (13)0.0379 (12)0.0149 (10)0.0092 (10)0.0053 (11)
C90.0346 (12)0.0374 (13)0.0379 (12)0.0224 (11)0.0091 (10)0.0018 (11)
C100.0285 (11)0.0305 (12)0.0312 (12)0.0168 (10)0.0032 (10)0.0045 (10)
C110.0318 (12)0.0300 (12)0.0343 (13)0.0130 (10)0.0011 (10)0.0017 (10)
C120.0462 (16)0.0340 (13)0.0603 (16)0.0226 (12)0.0028 (13)0.0010 (12)
C130.0437 (15)0.0356 (14)0.0460 (14)0.0111 (12)0.0041 (12)0.0056 (11)
C140.0399 (14)0.0418 (14)0.0410 (14)0.0260 (12)0.0038 (11)0.0049 (11)
C150.0358 (14)0.0417 (14)0.0458 (14)0.0181 (12)0.0126 (12)0.0141 (12)
C160.083 (3)0.135 (3)0.058 (2)0.078 (3)0.0010 (19)0.009 (2)
Geometric parameters (Å, º) top
O1—C31.429 (3)C7—C111.553 (3)
O1—H1O0.810 (10)C7—H70.9800
O2—C51.461 (2)C8—C91.525 (3)
O2—H2O0.820 (10)C8—H8A0.9700
O3—C61.438 (2)C8—H8B0.9700
O3—H3O0.822 (10)C9—C101.532 (3)
O4—C111.451 (3)C9—H9A0.9700
O4—H4O0.818 (10)C9—H9B0.9700
O5—C161.387 (4)C10—C141.545 (3)
O5—H5O0.823 (10)C11—C121.514 (3)
C1—C21.520 (3)C11—C131.525 (3)
C1—C101.533 (3)C12—H12A0.9600
C1—H1A0.9700C12—H12B0.9600
C1—H1B0.9700C12—H12C0.9600
C2—C31.518 (3)C13—H13A0.9600
C2—H2A0.9700C13—H13B0.9600
C2—H2B0.9700C13—H13C0.9600
C3—C41.526 (3)C14—H14A0.9600
C3—H30.9800C14—H14B0.9600
C4—C151.315 (3)C14—H14C0.9600
C4—C51.522 (3)C15—H15A0.9300
C5—C61.539 (3)C15—H15B0.9300
C5—C101.555 (3)C16—H16A0.9600
C6—C71.538 (3)C16—H16B0.9600
C6—H60.9800C16—H16C0.9600
C7—C81.528 (3)
C3—O1—H1O106.5 (19)C7—C8—H8B109.4
C5—O2—H2O109.0 (16)H8A—C8—H8B108.0
C6—O3—H3O109.4 (19)C8—C9—C10114.09 (19)
C11—O4—H4O111 (2)C8—C9—H9A108.7
C16—O5—H5O107 (3)C10—C9—H9A108.7
C2—C1—C10112.03 (19)C8—C9—H9B108.7
C2—C1—H1A109.2C10—C9—H9B108.7
C10—C1—H1A109.2H9A—C9—H9B107.6
C2—C1—H1B109.2C9—C10—C1109.94 (19)
C10—C1—H1B109.2C9—C10—C14109.51 (18)
H1A—C1—H1B107.9C1—C10—C14108.34 (18)
C3—C2—C1112.4 (2)C9—C10—C5108.51 (17)
C3—C2—H2A109.1C1—C10—C5109.00 (17)
C1—C2—H2A109.1C14—C10—C5111.54 (17)
C3—C2—H2B109.1O4—C11—C12105.58 (19)
C1—C2—H2B109.1O4—C11—C13109.80 (19)
H2A—C2—H2B107.9C12—C11—C13109.3 (2)
O1—C3—C2110.27 (19)O4—C11—C7108.99 (17)
O1—C3—C4112.2 (2)C12—C11—C7111.54 (19)
C2—C3—C4113.48 (19)C13—C11—C7111.50 (19)
O1—C3—H3106.8C11—C12—H12A109.5
C2—C3—H3106.8C11—C12—H12B109.5
C4—C3—H3106.8H12A—C12—H12B109.5
C15—C4—C5123.6 (2)C11—C12—H12C109.5
C15—C4—C3121.3 (2)H12A—C12—H12C109.5
C5—C4—C3114.70 (19)H12B—C12—H12C109.5
O2—C5—C4104.90 (16)C11—C13—H13A109.5
O2—C5—C6105.04 (16)C11—C13—H13B109.5
C4—C5—C6115.28 (17)H13A—C13—H13B109.5
O2—C5—C10106.26 (16)C11—C13—H13C109.5
C4—C5—C10111.33 (17)H13A—C13—H13C109.5
C6—C5—C10113.05 (17)H13B—C13—H13C109.5
O3—C6—C7111.11 (17)C10—C14—H14A109.5
O3—C6—C5110.79 (16)C10—C14—H14B109.5
C7—C6—C5111.44 (16)H14A—C14—H14B109.5
O3—C6—H6107.8C10—C14—H14C109.5
C7—C6—H6107.8H14A—C14—H14C109.5
C5—C6—H6107.8H14B—C14—H14C109.5
C8—C7—C6111.00 (18)C4—C15—H15A120.0
C8—C7—C11113.61 (18)C4—C15—H15B120.0
C6—C7—C11112.46 (18)H15A—C15—H15B120.0
C8—C7—H7106.4O5—C16—H16A109.5
C6—C7—H7106.4O5—C16—H16B109.5
C11—C7—H7106.4H16A—C16—H16B109.5
C9—C8—C7111.03 (18)O5—C16—H16C109.5
C9—C8—H8A109.4H16A—C16—H16C109.5
C7—C8—H8A109.4H16B—C16—H16C109.5
C9—C8—H8B109.4
C10—C1—C2—C355.5 (3)C11—C7—C8—C9177.22 (19)
C1—C2—C3—O1174.47 (19)C7—C8—C9—C1056.5 (3)
C1—C2—C3—C447.6 (3)C8—C9—C10—C1173.35 (19)
O1—C3—C4—C1515.0 (3)C8—C9—C10—C1467.7 (2)
C2—C3—C4—C15140.9 (2)C8—C9—C10—C554.2 (2)
O1—C3—C4—C5171.75 (17)C2—C1—C10—C9177.88 (19)
C2—C3—C4—C545.9 (3)C2—C1—C10—C1462.5 (2)
C15—C4—C5—O2108.7 (2)C2—C1—C10—C559.1 (2)
C3—C4—C5—O264.4 (2)O2—C5—C10—C961.7 (2)
C15—C4—C5—C66.3 (3)C4—C5—C10—C9175.39 (19)
C3—C4—C5—C6179.37 (18)C6—C5—C10—C953.0 (2)
C15—C4—C5—C10136.8 (2)O2—C5—C10—C158.0 (2)
C3—C4—C5—C1050.2 (2)C4—C5—C10—C155.7 (2)
O2—C5—C6—O3174.92 (15)C6—C5—C10—C1172.69 (17)
C4—C5—C6—O360.0 (2)O2—C5—C10—C14177.57 (18)
C10—C5—C6—O369.6 (2)C4—C5—C10—C1463.9 (2)
O2—C5—C6—C760.8 (2)C6—C5—C10—C1467.7 (2)
C4—C5—C6—C7175.74 (17)C8—C7—C11—O461.2 (2)
C10—C5—C6—C754.6 (2)C6—C7—C11—O466.0 (2)
O3—C6—C7—C869.6 (2)C8—C7—C11—C12177.3 (2)
C5—C6—C7—C854.5 (2)C6—C7—C11—C1250.2 (2)
O3—C6—C7—C1158.9 (2)C8—C7—C11—C1360.2 (2)
C5—C6—C7—C11176.99 (17)C6—C7—C11—C13172.63 (18)
C6—C7—C8—C954.9 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1O···O2i0.81 (1)2.08 (1)2.884 (2)171 (3)
O2—H2O···O50.82 (1)2.15 (1)2.953 (3)168 (2)
O3—H3O···O40.82 (1)1.96 (2)2.702 (2)150 (3)
O4—H4O···O1ii0.82 (1)1.98 (1)2.795 (3)172 (3)
O5—H5O···O3iii0.82 (1)1.97 (1)2.789 (3)175 (4)
Symmetry codes: (i) y, x+y, z1/6; (ii) x+1, y+1, z; (iii) xy, x, z+1/6.
 

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