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The title compound, C15H22O4, obtained from the dehydration of dihydro­artemisinin, has retained the endoperoxide bridge of the parent compound along with the C=C bond. The six-membered rings exhibit chair, twist-boat and envelope conformations.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806013109/tk2026sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806013109/tk2026Isup2.hkl
Contains datablock I

CCDC reference: 608511

Key indicators

  • Single-crystal X-ray study
  • T = 295 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.035
  • wR factor = 0.101
  • Data-to-parameter ratio = 10.8

checkCIF/PLATON results

No syntax errors found



Alert level B PLAT024_ALERT_4_B Merging of Friedel Pairs is STRONGLY Indicated . !
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 27.40 From the CIF: _reflns_number_total 1896 Count of symmetry unique reflns 1889 Completeness (_total/calc) 100.37% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 7 Fraction of Friedel pairs measured 0.004 Are heavy atom types Z>Si present no
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 0 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 0 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

Computing details top

Data collection: RAPID-AUTO (Rigaku Corporation, 1998); cell refinement: RAPID-AUTO; data reduction: CrystalStructure (Rigaku/MSC, 2002); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976); software used to prepare material for publication: SHELXL97.

9,10-Dehydrodeoxyartemisinin top
Crystal data top
C15H22O4F(000) = 576
Mr = 266.33Dx = 1.246 Mg m3
Orthorhombic, P212121Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2abCell parameters from 12144 reflections
a = 6.2460 (12) Åθ = 3.3–27.4°
b = 9.0416 (18) ŵ = 0.09 mm1
c = 25.132 (5) ÅT = 295 K
V = 1419.3 (5) Å3Prism, colorless
Z = 40.36 × 0.25 × 0.18 mm
Data collection top
Rigaku R-AXIS RAPID
diffractometer
1896 independent reflections
Radiation source: fine-focus sealed tube1658 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.021
Detector resolution: 10.000 pixels mm-1θmax = 27.4°, θmin = 3.2°
ω scansh = 68
Absorption correction: multi-scan
(ABSCOR; Higashi, 1995)
k = 1111
Tmin = 0.962, Tmax = 0.978l = 3232
13861 measured 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)] = 0.035Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.101H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.0671P)2 + 0.0449P]
where P = (Fo2 + 2Fc2)/3
1896 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.11 e Å3
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
O10.5740 (3)0.57592 (14)0.19525 (5)0.0578 (4)
O20.9047 (2)0.36439 (17)0.18730 (5)0.0553 (4)
O30.82582 (18)0.35851 (16)0.13236 (5)0.0507 (3)
O40.5713 (2)0.34360 (14)0.22712 (4)0.0451 (3)
C10.6289 (4)0.6678 (2)0.15433 (9)0.0585 (5)
H10.67310.76280.16340.070*
C20.6254 (3)0.6349 (2)0.10339 (9)0.0559 (5)
C30.6984 (6)0.7434 (3)0.06167 (11)0.0882 (8)
H3A0.74100.83410.07850.132*
H3B0.58310.76270.03740.132*
H3C0.81770.70270.04250.132*
C40.5542 (3)0.4835 (2)0.08580 (7)0.0478 (4)
H40.64280.45490.05530.057*
C50.3192 (3)0.4827 (2)0.06747 (8)0.0569 (5)
H5A0.22870.51700.09630.068*
H5B0.30230.55040.03780.068*
C60.2485 (4)0.3297 (3)0.05064 (7)0.0594 (5)
H6A0.33080.29920.01980.071*
H6B0.09890.33290.04040.071*
C70.2776 (3)0.2164 (2)0.09480 (7)0.0499 (4)
H70.18320.24460.12430.060*
C80.2079 (5)0.0633 (3)0.07545 (11)0.0780 (7)
H8A0.06650.06930.06060.117*
H8B0.20770.00450.10480.117*
H8C0.30590.02900.04870.117*
C90.5094 (3)0.21567 (18)0.11603 (7)0.0435 (4)
H90.59980.17840.08710.052*
C100.5330 (3)0.1064 (2)0.16236 (8)0.0507 (4)
H10A0.41310.12020.18640.061*
H10B0.52340.00680.14820.061*
C110.7394 (3)0.1190 (2)0.19436 (8)0.0531 (4)
H11A0.85950.09720.17120.064*
H11B0.73770.04520.22240.064*
C120.7736 (3)0.2715 (2)0.21945 (7)0.0487 (4)
C130.8872 (4)0.2674 (3)0.27263 (9)0.0679 (6)
H13A1.01260.20650.26990.102*
H13B0.79290.22730.29910.102*
H13C0.92810.36590.28260.102*
C140.5086 (3)0.42841 (18)0.18326 (6)0.0411 (4)
H140.35180.42710.18160.049*
C150.5940 (2)0.37081 (18)0.13012 (6)0.0394 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0830 (10)0.0412 (6)0.0491 (7)0.0018 (7)0.0046 (7)0.0016 (5)
O20.0394 (6)0.0659 (8)0.0607 (8)0.0025 (7)0.0076 (6)0.0142 (7)
O30.0337 (6)0.0678 (8)0.0506 (7)0.0059 (6)0.0046 (5)0.0098 (6)
O40.0483 (6)0.0485 (6)0.0384 (6)0.0019 (6)0.0002 (5)0.0029 (5)
C10.0635 (12)0.0418 (9)0.0702 (12)0.0020 (9)0.0099 (10)0.0103 (8)
C20.0557 (10)0.0514 (9)0.0607 (11)0.0008 (9)0.0038 (9)0.0167 (9)
C30.105 (2)0.0755 (15)0.0839 (17)0.0142 (17)0.0030 (16)0.0338 (13)
C40.0466 (9)0.0549 (9)0.0419 (8)0.0033 (8)0.0041 (8)0.0090 (7)
C50.0541 (10)0.0654 (11)0.0512 (10)0.0093 (9)0.0086 (9)0.0120 (9)
C60.0537 (10)0.0813 (13)0.0433 (9)0.0029 (11)0.0079 (8)0.0000 (9)
C70.0462 (9)0.0581 (10)0.0453 (9)0.0001 (8)0.0008 (8)0.0063 (8)
C80.0845 (17)0.0728 (14)0.0766 (14)0.0150 (14)0.0167 (14)0.0125 (12)
C90.0427 (9)0.0472 (8)0.0406 (8)0.0067 (7)0.0061 (7)0.0051 (7)
C100.0572 (11)0.0403 (8)0.0546 (10)0.0011 (8)0.0001 (9)0.0006 (7)
C110.0529 (10)0.0483 (9)0.0581 (10)0.0114 (9)0.0008 (9)0.0088 (8)
C120.0415 (8)0.0536 (9)0.0511 (9)0.0013 (8)0.0062 (8)0.0105 (8)
C130.0649 (12)0.0733 (13)0.0655 (12)0.0077 (12)0.0231 (11)0.0151 (10)
C140.0410 (8)0.0423 (8)0.0401 (8)0.0036 (7)0.0012 (6)0.0003 (6)
C150.0327 (7)0.0461 (8)0.0395 (8)0.0056 (7)0.0040 (6)0.0038 (7)
Geometric parameters (Å, º) top
O1—C11.366 (2)C6—H6B0.9700
O1—C141.427 (2)C7—C81.531 (3)
O2—C121.424 (2)C7—C91.543 (3)
O2—O31.4670 (18)C7—H70.9800
O3—C151.4536 (19)C8—H8A0.9600
O4—C141.3989 (19)C8—H8B0.9600
O4—C121.434 (2)C8—H8C0.9600
C1—C21.314 (3)C9—C101.534 (2)
C1—H10.9300C9—C151.540 (2)
C2—C41.506 (3)C9—H90.9800
C2—C31.507 (3)C10—C111.523 (3)
C3—H3A0.9600C10—H10A0.9700
C3—H3B0.9600C10—H10B0.9700
C3—H3C0.9600C11—C121.531 (3)
C4—C151.530 (2)C11—H11A0.9700
C4—C51.538 (3)C11—H11B0.9700
C4—H40.9800C12—C131.514 (3)
C5—C61.512 (3)C13—H13A0.9600
C5—H5A0.9700C13—H13B0.9600
C5—H5B0.9700C13—H13C0.9600
C6—C71.521 (3)C14—C151.529 (2)
C6—H6A0.9700C14—H140.9800
C1—O1—C14118.78 (15)H8A—C8—H8C109.5
C12—O2—O3108.63 (13)H8B—C8—H8C109.5
C15—O3—O2111.60 (12)C10—C9—C15112.28 (14)
C14—O4—C12112.95 (13)C10—C9—C7110.82 (15)
C2—C1—O1126.26 (19)C15—C9—C7113.42 (14)
C2—C1—H1116.9C10—C9—H9106.6
O1—C1—H1116.9C15—C9—H9106.6
C1—C2—C4119.78 (17)C7—C9—H9106.6
C1—C2—C3121.7 (2)C11—C10—C9115.70 (16)
C4—C2—C3118.5 (2)C11—C10—H10A108.4
C2—C3—H3A109.5C9—C10—H10A108.4
C2—C3—H3B109.5C11—C10—H10B108.4
H3A—C3—H3B109.5C9—C10—H10B108.4
C2—C3—H3C109.5H10A—C10—H10B107.4
H3A—C3—H3C109.5C10—C11—C12113.76 (15)
H3B—C3—H3C109.5C10—C11—H11A108.8
C2—C4—C15110.11 (15)C12—C11—H11A108.8
C2—C4—C5111.96 (17)C10—C11—H11B108.8
C15—C4—C5111.69 (15)C12—C11—H11B108.8
C2—C4—H4107.6H11A—C11—H11B107.7
C15—C4—H4107.6O2—C12—O4108.35 (14)
C5—C4—H4107.6O2—C12—C13104.22 (16)
C6—C5—C4111.51 (18)O4—C12—C13107.77 (17)
C6—C5—H5A109.3O2—C12—C11112.18 (16)
C4—C5—H5A109.3O4—C12—C11109.98 (15)
C6—C5—H5B109.3C13—C12—C11114.02 (16)
C4—C5—H5B109.3C12—C13—H13A109.5
H5A—C5—H5B108.0C12—C13—H13B109.5
C5—C6—C7112.15 (15)H13A—C13—H13B109.5
C5—C6—H6A109.2C12—C13—H13C109.5
C7—C6—H6A109.2H13A—C13—H13C109.5
C5—C6—H6B109.2H13B—C13—H13C109.5
C7—C6—H6B109.2O4—C14—O1105.40 (13)
H6A—C6—H6B107.9O4—C14—C15113.81 (13)
C6—C7—C8110.08 (17)O1—C14—C15113.75 (14)
C6—C7—C9111.54 (16)O4—C14—H14107.9
C8—C7—C9111.90 (18)O1—C14—H14107.9
C6—C7—H7107.7C15—C14—H14107.9
C8—C7—H7107.7O3—C15—C14109.87 (14)
C9—C7—H7107.7O3—C15—C4103.92 (13)
C7—C8—H8A109.5C14—C15—C4110.63 (13)
C7—C8—H8B109.5O3—C15—C9106.31 (14)
H8A—C8—H8B109.5C14—C15—C9113.03 (14)
C7—C8—H8C109.5C4—C15—C9112.56 (14)
C12—O2—O3—C1544.96 (19)C10—C11—C12—O425.3 (2)
C14—O1—C1—C21.0 (3)C10—C11—C12—C13146.47 (18)
O1—C1—C2—C40.4 (4)C12—O4—C14—O196.29 (16)
O1—C1—C2—C3177.4 (2)C12—O4—C14—C1529.0 (2)
C1—C2—C4—C1526.1 (3)C1—O1—C14—O4149.55 (17)
C3—C2—C4—C15151.8 (2)C1—O1—C14—C1524.2 (2)
C1—C2—C4—C598.8 (2)O2—O3—C15—C1415.61 (18)
C3—C2—C4—C583.3 (3)O2—O3—C15—C4134.01 (14)
C2—C4—C5—C6179.19 (16)O2—O3—C15—C9107.02 (15)
C15—C4—C5—C655.2 (2)O4—C14—C15—O355.39 (19)
C4—C5—C6—C757.1 (2)O1—C14—C15—O365.36 (18)
C5—C6—C7—C8178.9 (2)O4—C14—C15—C4169.56 (14)
C5—C6—C7—C954.1 (2)O1—C14—C15—C448.8 (2)
C6—C7—C9—C10177.18 (15)O4—C14—C15—C963.18 (19)
C8—C7—C9—C1059.0 (2)O1—C14—C15—C9176.07 (14)
C6—C7—C9—C1549.82 (19)C2—C4—C15—O369.53 (19)
C8—C7—C9—C15173.64 (18)C5—C4—C15—O3165.42 (16)
C15—C9—C10—C1139.4 (2)C2—C4—C15—C1448.3 (2)
C7—C9—C10—C11167.39 (15)C5—C4—C15—C1476.7 (2)
C9—C10—C11—C1258.7 (2)C2—C4—C15—C9175.86 (15)
O3—O2—C12—O473.64 (17)C5—C4—C15—C950.8 (2)
O3—O2—C12—C13171.79 (15)C10—C9—C15—O371.56 (17)
O3—O2—C12—C1147.95 (18)C7—C9—C15—O3161.85 (13)
C14—O4—C12—O233.15 (19)C10—C9—C15—C1449.05 (19)
C14—O4—C12—C13145.37 (16)C7—C9—C15—C1477.54 (17)
C14—O4—C12—C1189.79 (17)C10—C9—C15—C4175.30 (14)
C10—C11—C12—O295.36 (19)C7—C9—C15—C448.71 (19)
 

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