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The crystal structure of a known spiro­lactone, hyperolactone C [systematic name: (5S,9S)-9-methyl-2-phenyl-9-vinyl-1,7-dioxa­spiro­[4.4]­non-2-ene-4,6-dione], isolated from Hypericum lloydii (Svenson) P. Adams (Sandhill St John's Wort, Clusiaceae), native to the southeastern USA, is presented.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026819/is6009sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026819/is6009Isup2.hkl
Contains datablock I

CCDC reference: 259091

Key indicators

  • Single-crystal X-ray study
  • T = 95 K
  • Mean [sigma](C-C) = 0.009 Å
  • R factor = 0.068
  • wR factor = 0.154
  • Data-to-parameter ratio = 7.3

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT089_ALERT_3_C Poor Data / Parameter Ratio (Zmax .LT. 18) ..... 7.26 PLAT165_ALERT_3_C Nr. of Status R Flagged Non-Hydrogen Atoms ..... 6 PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 9
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 25.00 From the CIF: _reflns_number_total 1270 Count of symmetry unique reflns 1277 Completeness (_total/calc) 99.45% 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
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 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 3 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: local software; cell refinement: local software; data reduction: local software; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP (Johnson, 1965); software used to prepare material for publication: SHELXL97.

(5S,9S)-9-methyl-2-phenyl-9-vinyl-1,7-dioxaspiro[4.4]non-2-ene-4,6-dione top
Crystal data top
C16H14O4F(000) = 284
Mr = 270.27Dx = 1.349 Mg m3
Monoclinic, P21Melting point: 370 K
Hall symbol: P 2ybMo Kα radiation, λ = 0.71069 Å
a = 6.215 (7) ÅCell parameters from 35 reflections
b = 7.491 (7) Åθ = 4.4–10.6°
c = 14.461 (15) ŵ = 0.10 mm1
β = 98.68 (8)°T = 95 K
V = 665.5 (12) Å3Needle, colorless
Z = 20.42 × 0.25 × 0.12 mm
Data collection top
Stoe
diffractometer
Rint = 0.087
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.9°
Graphite monochromatorh = 77
ω scansk = 38
1612 measured reflectionsl = 117
1270 independent reflections3 standard reflections every 100 reflections
943 reflections with I > 2σ(I) intensity decay: 0.1%
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)] = 0.068Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.154H-atom parameters constrained
S = 1.08 w = 1/[σ2(Fo2) + (0.0556P)2 + 0.1091P]
where P = (Fo2 + 2Fc2)/3
1270 reflections(Δ/σ)max < 0.001
175 parametersΔρmax = 0.28 e Å3
1 restraintΔρmin = 0.28 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.

The non-hydrogen atoms were refined with anisotropic displacement parameters.

The C atoms of the phenyl rings were fitted to a regular hexagon with C—C distances of 1.39 Å (AFIX 66 of SHELXL97). The H atoms of the phenyl rings were put at the external bisector of the C—C—C angle at a C—H distance of 0.95 Å and common isotropic displacement parameters were refined for the H atoms of the same phenyl group (AFIX 43 of SHELXL97).

The H-atoms H3 and H92 were put at the external bisector of the C—C—C angle at a C—H distance of 0.95 Å (AFIX 43 of SHELXL97). The H-atoms bonded to C8 were refined with an idealized geometry with approximately tetrahedral angles and C—H distances of 0.99 Å (AFIX 23 of SHELXL97). The H-atoms bonded to C3 and C8 were refined with a common isotropic displacement parameter. The individual isotropic displacement parameter of H92 was free to refine.

The H-atoms bonded to C93 were refined with common isotropic displacement parameters and idealized geometry with the H-atoms in the C9—C92—C93 plane, angles of 120°, and C—H distances of 0.95 Å (AFIX 93 of SHELXL97).

The H-atoms of the methyl group were refined with one common isotropic displacement parameter and idealized geometry with tetrahedral angles, enabling rotation around the X—C bond, and C—H distances of 0.98 Å (AFIX 137 of SHELXL97).

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.3240 (6)0.3111 (7)0.7857 (3)0.0168 (11)
C20.1557 (10)0.3580 (9)0.8335 (4)0.0139 (15)
C30.0286 (9)0.4063 (10)0.7776 (4)0.0173 (15)
H30.16120.43960.79800.015 (10)*
C40.0084 (9)0.3990 (9)0.6818 (4)0.0124 (14)
O40.1047 (6)0.4382 (7)0.6077 (3)0.0191 (11)
C50.2496 (10)0.3299 (10)0.6881 (4)0.0143 (14)
C60.3834 (9)0.4642 (10)0.6422 (4)0.0156 (15)
O60.4724 (7)0.5938 (7)0.6773 (3)0.0212 (12)
O70.3816 (6)0.4185 (7)0.5531 (3)0.0199 (12)
C80.2756 (10)0.2424 (10)0.5343 (5)0.0157 (15)
H810.36000.16690.49650.015 (10)*
H820.12620.25680.50000.015 (10)*
C90.2700 (9)0.1581 (10)0.6303 (4)0.0134 (15)
C210.2012 (6)0.3355 (6)0.93493 (19)0.0152 (14)
C220.0536 (5)0.4003 (6)0.9900 (2)0.0211 (16)
H220.07570.45810.96160.027 (9)*
C230.0953 (6)0.3805 (7)1.0866 (2)0.0242 (18)
H230.00560.42481.12430.027 (9)*
C240.2845 (7)0.2960 (8)1.12818 (19)0.0222 (17)
H240.31300.28251.19420.027 (9)*
C250.4321 (5)0.2312 (7)1.0731 (3)0.0227 (17)
H250.56150.17341.10150.027 (9)*
C260.3904 (6)0.2509 (6)0.9765 (2)0.0199 (16)
H260.49130.20660.93880.027 (9)*
C910.4927 (10)0.0702 (11)0.6664 (5)0.0212 (17)
H9110.49910.03880.73250.031 (12)*
H9120.61010.15420.65940.031 (12)*
H9130.50960.03800.63000.031 (12)*
C920.0759 (10)0.0367 (10)0.6315 (5)0.0174 (16)
H920.05730.06990.59430.03 (2)*
C930.0785 (11)0.1152 (10)0.6815 (4)0.0190 (16)
H9310.20880.15260.71950.030 (14)*
H9320.05010.18480.67880.030 (14)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.013 (2)0.026 (3)0.013 (2)0.003 (2)0.0068 (17)0.003 (2)
C20.020 (3)0.006 (4)0.019 (3)0.000 (3)0.010 (3)0.002 (3)
C30.019 (3)0.019 (4)0.016 (3)0.002 (3)0.013 (3)0.003 (3)
C40.017 (3)0.006 (3)0.013 (3)0.001 (3)0.003 (3)0.002 (3)
O40.020 (2)0.023 (3)0.016 (2)0.006 (2)0.0053 (18)0.003 (2)
C50.021 (3)0.016 (4)0.006 (3)0.004 (3)0.004 (2)0.003 (3)
C60.017 (3)0.014 (4)0.014 (4)0.002 (3)0.002 (3)0.003 (3)
O60.020 (2)0.021 (3)0.023 (3)0.001 (2)0.007 (2)0.006 (2)
O70.020 (2)0.024 (3)0.019 (3)0.007 (2)0.0118 (18)0.000 (2)
C80.017 (3)0.018 (4)0.014 (3)0.003 (3)0.008 (3)0.002 (3)
C90.013 (3)0.018 (4)0.010 (3)0.005 (3)0.005 (2)0.003 (3)
C210.016 (3)0.013 (4)0.018 (3)0.006 (3)0.008 (3)0.004 (3)
C220.023 (3)0.021 (4)0.020 (4)0.002 (3)0.005 (3)0.001 (4)
C230.032 (3)0.028 (5)0.015 (4)0.000 (4)0.010 (3)0.008 (3)
C240.038 (4)0.021 (5)0.007 (3)0.004 (3)0.000 (3)0.002 (3)
C250.025 (3)0.021 (4)0.022 (4)0.001 (3)0.003 (3)0.002 (3)
C260.023 (3)0.019 (4)0.019 (4)0.004 (3)0.010 (3)0.002 (3)
C910.019 (3)0.027 (5)0.018 (4)0.001 (3)0.005 (3)0.011 (3)
C920.017 (3)0.018 (4)0.018 (4)0.006 (3)0.008 (3)0.002 (3)
C930.026 (3)0.016 (4)0.017 (4)0.004 (3)0.011 (3)0.003 (3)
Geometric parameters (Å, º) top
O1—C21.383 (7)C21—C221.3900
O1—C51.424 (7)C21—C261.3900
C2—C31.348 (9)C22—C231.3900
C2—C211.462 (7)C22—H220.9500
C3—C41.439 (8)C23—C241.3900
C3—H30.9500C23—H230.9500
C4—O41.225 (7)C24—C251.3900
C4—C51.576 (8)C24—H240.9500
C5—C61.521 (9)C25—C261.3900
C5—C91.551 (9)C25—H250.9500
C6—O61.193 (8)C26—H260.9500
C6—O71.331 (8)C91—H9110.9800
O7—C81.482 (9)C91—H9120.9800
C8—C91.530 (9)C91—H9130.9800
C8—H810.9900C92—C931.347 (10)
C8—H820.9900C92—H920.9500
C9—C911.550 (8)C93—H9310.9500
C9—C921.513 (9)C93—H9320.9500
C2—O1—C5108.2 (5)C91—C9—C5108.2 (5)
C3—C2—O1114.0 (5)C22—C21—C26120.0
C3—C2—C21130.6 (5)C22—C21—C2119.4 (3)
O1—C2—C21115.2 (5)C26—C21—C2120.6 (3)
C2—C3—C4108.8 (5)C21—C22—C23120.0
C2—C3—H3125.6C21—C22—H22120.0
C4—C3—H3125.6C23—C22—H22120.0
O4—C4—C3132.7 (6)C24—C23—C22120.0
O4—C4—C5123.0 (5)C24—C23—H23120.0
C3—C4—C5104.2 (5)C22—C23—H23120.0
O1—C5—C6112.4 (5)C23—C24—C25120.0
O1—C5—C9114.3 (6)C23—C24—H24120.0
C6—C5—C9102.6 (5)C25—C24—H24120.0
O1—C5—C4104.7 (4)C26—C25—C24120.0
C6—C5—C4109.6 (6)C26—C25—H25120.0
C9—C5—C4113.3 (5)C24—C25—H25120.0
O6—C6—O7123.9 (6)C25—C26—C21120.0
O6—C6—C5126.9 (6)C25—C26—H26120.0
O7—C6—C5109.1 (5)C21—C26—H26120.0
C6—O7—C8110.2 (5)C9—C91—H911109.5
O7—C8—C9105.7 (5)C9—C91—H912109.5
O7—C8—H81110.6H911—C91—H912109.5
C9—C8—H81110.6C9—C91—H913109.5
O7—C8—H82110.6H911—C91—H913109.5
C9—C8—H82110.6H912—C91—H913109.5
H81—C8—H82108.7C93—C92—C9124.7 (6)
C92—C9—C8112.7 (5)C93—C92—H92117.7
C92—C9—C91114.4 (6)C9—C92—H92117.7
C8—C9—C91109.8 (5)C92—C93—H931120.0
C92—C9—C5111.3 (5)C92—C93—H932120.0
C8—C9—C599.3 (5)H931—C93—H932120.0
C5—O1—C2—C30.5 (8)O7—C8—C9—C531.3 (5)
C5—O1—C2—C21176.4 (5)O1—C5—C9—C9284.6 (6)
O1—C2—C3—C41.7 (8)C6—C5—C9—C92153.4 (5)
C21—C2—C3—C4176.8 (6)C4—C5—C9—C9235.3 (7)
C2—C3—C4—O4176.0 (7)O1—C5—C9—C8156.5 (5)
C2—C3—C4—C52.0 (8)C6—C5—C9—C834.5 (6)
C2—O1—C5—C6119.7 (6)C4—C5—C9—C883.6 (6)
C2—O1—C5—C9123.8 (5)O1—C5—C9—C9141.9 (7)
C2—O1—C5—C40.8 (7)C6—C5—C9—C9180.1 (6)
O4—C4—C5—O1176.6 (6)C4—C5—C9—C91161.8 (5)
C3—C4—C5—O11.7 (7)C3—C2—C21—C2213.2 (9)
O4—C4—C5—C655.8 (8)O1—C2—C21—C22171.8 (4)
C3—C4—C5—C6122.5 (6)C3—C2—C21—C26167.2 (6)
O4—C4—C5—C958.2 (9)O1—C2—C21—C267.9 (7)
C3—C4—C5—C9123.5 (6)C26—C21—C22—C230.0
O1—C5—C6—O631.2 (9)C2—C21—C22—C23179.7 (5)
C9—C5—C6—O6154.5 (6)C21—C22—C23—C240.0
C4—C5—C6—O684.8 (7)C22—C23—C24—C250.0
O1—C5—C6—O7150.8 (5)C23—C24—C25—C260.0
C9—C5—C6—O727.5 (7)C24—C25—C26—C210.0
C4—C5—C6—O793.1 (6)C22—C21—C26—C250.0
O6—C6—O7—C8174.6 (6)C2—C21—C26—C25179.7 (5)
C5—C6—O7—C87.4 (7)C8—C9—C92—C93144.3 (6)
C6—O7—C8—C916.2 (6)C91—C9—C92—C9317.9 (9)
O7—C8—C9—C92149.1 (5)C5—C9—C92—C93105.2 (7)
O7—C8—C9—C9182.0 (6)
 

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