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The title structure, 15,18-di­methyl-5-dioxo-14-oxapenta­cyclo­[11.4.1.02,15.04,13.06,11]­octadeca-3,6,8,10-tetraene-18-carb­aldehyde, C20H18O4, is a novel naphtho­quinone, isolated from Stereospermum personatum. In the bicyclic system, all three six-membered rings adopt a boat conformation. Two intermolecular C=O...H—C interactions link the mol­ecules into a chain.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S160053680500259X/bt6594sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S160053680500259X/bt6594Isup2.hkl
Contains datablock I

CCDC reference: 264098

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.003 Å
  • R factor = 0.039
  • wR factor = 0.105
  • Data-to-parameter ratio = 8.9

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT029_ALERT_3_C _diffrn_measured_fraction_theta_full Low ....... 0.98 PLAT220_ALERT_2_C Large Non-Solvent O Ueq(max)/Ueq(min) ... 3.09 Ratio
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 27.96 From the CIF: _reflns_number_total 1954 Count of symmetry unique reflns 2005 Completeness (_total/calc) 97.46% 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 2 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 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 1 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 and PARST (Nardelli, 1995).

15,18-dimethyl-5-dioxo-14- oxapentacyclo[11.4.1.02,15.04,13.06,11]octadeca-3,6,8,10-tetraene- 18-carbaldehyde top
Crystal data top
C20H18O4F(000) = 680
Mr = 322.34Dx = 1.338 Mg m3
Orthorhombic, Pna21Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2c -2nCell parameters from 6143 reflections
a = 13.3078 (19) Åθ = 2.7–27.9°
b = 7.9299 (11) ŵ = 0.09 mm1
c = 15.168 (2) ÅT = 273 K
V = 1600.7 (4) Å3Needle, pale yellow
Z = 40.25 × 0.13 × 0.10 mm
Data collection top
CCD Area Detector
diffractometer
1879 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.017
Graphite monochromatorθmax = 28.0°, θmin = 3.0°
ω scansh = 1713
9248 measured reflectionsk = 1010
1954 independent reflectionsl = 1919
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)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.105H-atom parameters constrained
S = 1.03 w = 1/[σ2(Fo2) + (0.0762P)2 + 0.1221P]
where P = (Fo2 + 2Fc2)/3
1954 reflections(Δ/σ)max < 0.001
219 parametersΔρmax = 0.20 e Å3
1 restraintΔρmin = 0.24 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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.87648 (14)0.0283 (2)0.75882 (12)0.0437 (4)
C20.93689 (14)0.0353 (3)0.67646 (12)0.0425 (4)
C31.00326 (16)0.0978 (3)0.66023 (15)0.0558 (5)
H31.00740.18760.69950.067*
C41.06305 (17)0.0951 (4)0.58516 (18)0.0675 (7)
H41.10750.18330.57440.081*
C51.05701 (18)0.0371 (4)0.52658 (16)0.0708 (8)
H51.09760.03760.47670.085*
C60.9914 (2)0.1687 (3)0.54110 (16)0.0639 (6)
H60.98770.25690.50080.077*
C70.93012 (16)0.1701 (3)0.61678 (13)0.0493 (4)
C80.8620 (2)0.3162 (3)0.63272 (16)0.0620 (6)
C90.80118 (17)0.3133 (3)0.71384 (13)0.0470 (4)
C100.79883 (13)0.1672 (2)0.77739 (10)0.0361 (3)
C110.68926 (14)0.0927 (2)0.77901 (12)0.0398 (4)
C120.62095 (14)0.2372 (2)0.81775 (14)0.0446 (4)
H120.56020.25050.78190.053*
C130.68179 (15)0.4045 (2)0.81941 (15)0.0452 (4)
H130.63860.50030.83450.054*
C140.73881 (18)0.4377 (2)0.73770 (15)0.0515 (5)
H140.73200.53680.70550.062*
C150.6543 (2)0.0400 (3)0.68666 (16)0.0594 (6)
H15A0.70040.04120.66280.089*
H15B0.65210.13720.64900.089*
H15C0.58850.00910.69040.089*
C160.68555 (15)0.0594 (2)0.84040 (16)0.0481 (4)
H160.71820.05180.89450.058*
C170.59298 (16)0.2195 (3)0.91621 (16)0.0532 (5)
H17A0.53310.28420.92980.064*
H17B0.58120.10240.93140.064*
C180.68435 (15)0.2893 (3)0.96651 (13)0.0490 (4)
H18A0.66370.37661.00750.059*
H18B0.71750.20010.99930.059*
C190.75483 (14)0.3617 (2)0.89646 (13)0.0417 (4)
C200.82098 (19)0.5065 (3)0.92709 (18)0.0591 (5)
H20A0.86450.46810.97340.089*
H20B0.77950.59660.94870.089*
H20C0.86070.54640.87850.089*
O10.88646 (16)0.0859 (2)0.81077 (12)0.0710 (6)
O20.8574 (3)0.4315 (3)0.58089 (18)0.1188 (12)
O30.64282 (18)0.1887 (2)0.82283 (18)0.0806 (6)
O40.82152 (9)0.22651 (15)0.86547 (8)0.0384 (3)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0510 (9)0.0439 (9)0.0361 (8)0.0132 (7)0.0001 (7)0.0008 (7)
C20.0410 (8)0.0526 (9)0.0339 (8)0.0018 (7)0.0045 (6)0.0074 (7)
C30.0491 (10)0.0732 (13)0.0451 (10)0.0127 (10)0.0040 (8)0.0116 (10)
C40.0489 (11)0.099 (2)0.0551 (12)0.0112 (11)0.0020 (10)0.0245 (14)
C50.0532 (12)0.112 (2)0.0471 (12)0.0166 (13)0.0117 (9)0.0255 (13)
C60.0703 (14)0.0821 (15)0.0394 (9)0.0220 (12)0.0067 (10)0.0054 (11)
C70.0530 (10)0.0590 (11)0.0360 (8)0.0096 (8)0.0001 (8)0.0042 (8)
C80.0854 (16)0.0563 (13)0.0442 (10)0.0034 (12)0.0090 (11)0.0130 (10)
C90.0638 (11)0.0384 (9)0.0387 (8)0.0047 (8)0.0018 (8)0.0091 (7)
C100.0467 (8)0.0319 (7)0.0297 (7)0.0068 (6)0.0018 (6)0.0027 (6)
C110.0468 (8)0.0326 (7)0.0400 (8)0.0051 (6)0.0085 (7)0.0024 (6)
C120.0414 (8)0.0404 (8)0.0520 (10)0.0096 (7)0.0088 (8)0.0041 (8)
C130.0536 (10)0.0315 (8)0.0505 (9)0.0114 (7)0.0067 (8)0.0017 (7)
C140.0717 (12)0.0353 (8)0.0477 (10)0.0095 (8)0.0091 (9)0.0086 (7)
C150.0729 (14)0.0558 (12)0.0494 (11)0.0061 (10)0.0193 (10)0.0122 (10)
C160.0523 (9)0.0352 (8)0.0568 (11)0.0031 (7)0.0025 (8)0.0027 (8)
C170.0453 (9)0.0534 (10)0.0609 (13)0.0062 (8)0.0087 (9)0.0049 (9)
C180.0532 (10)0.0514 (10)0.0422 (9)0.0078 (8)0.0048 (7)0.0067 (8)
C190.0500 (9)0.0342 (7)0.0408 (8)0.0045 (7)0.0041 (7)0.0053 (7)
C200.0698 (13)0.0456 (10)0.0618 (12)0.0063 (9)0.0108 (11)0.0112 (10)
O10.0960 (13)0.0626 (9)0.0543 (9)0.0444 (9)0.0204 (9)0.0193 (8)
O20.184 (3)0.0931 (17)0.0792 (16)0.0420 (19)0.0494 (18)0.0518 (14)
O30.1012 (14)0.0407 (8)0.0999 (15)0.0144 (9)0.0171 (13)0.0032 (9)
O40.0420 (6)0.0392 (6)0.0339 (5)0.0057 (4)0.0052 (5)0.0007 (5)
Geometric parameters (Å, º) top
C1—O11.207 (2)C12—C171.545 (3)
C1—C21.487 (3)C12—C131.554 (3)
C1—C101.536 (2)C12—H120.9800
C2—C31.398 (3)C13—C141.477 (3)
C2—C71.404 (3)C13—C191.557 (3)
C3—C41.389 (3)C13—H130.9800
C3—H30.9300C14—H140.9300
C4—C51.377 (4)C15—H15A0.9600
C4—H40.9300C15—H15B0.9600
C5—C61.378 (4)C15—H15C0.9600
C5—H50.9300C16—O31.202 (3)
C6—C71.408 (3)C16—H160.9300
C6—H60.9300C17—C181.538 (3)
C7—C81.490 (3)C17—H17A0.9700
C8—O21.208 (3)C17—H17B0.9700
C8—C91.473 (3)C18—C191.529 (3)
C9—C141.339 (3)C18—H18A0.9700
C9—C101.507 (2)C18—H18B0.9700
C10—O41.448 (2)C19—O41.469 (2)
C10—C111.573 (3)C19—C201.520 (3)
C11—C161.525 (3)C20—H20A0.9600
C11—C151.534 (3)C20—H20B0.9600
C11—C121.576 (3)C20—H20C0.9600
O1—C1—C2121.12 (17)C11—C12—H12110.3
O1—C1—C10119.45 (17)C14—C13—C12113.98 (17)
C2—C1—C10119.42 (16)C14—C13—C19110.35 (16)
C3—C2—C7120.13 (19)C12—C13—C1998.71 (14)
C3—C2—C1117.49 (19)C14—C13—H13111.1
C7—C2—C1122.37 (17)C12—C13—H13111.1
C4—C3—C2119.7 (2)C19—C13—H13111.1
C4—C3—H3120.2C9—C14—C13114.44 (17)
C2—C3—H3120.2C9—C14—H14122.8
C5—C4—C3120.5 (2)C13—C14—H14122.8
C5—C4—H4119.8C11—C15—H15A109.5
C3—C4—H4119.8C11—C15—H15B109.5
C4—C5—C6120.7 (2)H15A—C15—H15B109.5
C4—C5—H5119.6C11—C15—H15C109.5
C6—C5—H5119.6H15A—C15—H15C109.5
C5—C6—C7120.2 (3)H15B—C15—H15C109.5
C5—C6—H6119.9O3—C16—C11123.7 (2)
C7—C6—H6119.9O3—C16—H16118.2
C2—C7—C6118.8 (2)C11—C16—H16118.2
C2—C7—C8121.76 (18)C18—C17—C12104.85 (16)
C6—C7—C8119.4 (2)C18—C17—H17A110.8
O2—C8—C9121.8 (2)C12—C17—H17A110.8
O2—C8—C7120.9 (2)C18—C17—H17B110.8
C9—C8—C7117.24 (18)C12—C17—H17B110.8
C14—C9—C8123.70 (19)H17A—C17—H17B108.9
C14—C9—C10112.38 (18)C19—C18—C17105.97 (17)
C8—C9—C10123.88 (18)C19—C18—H18A110.5
O4—C10—C9109.62 (14)C17—C18—H18A110.5
O4—C10—C1105.18 (13)C19—C18—H18B110.5
C9—C10—C1114.82 (16)C17—C18—H18B110.5
O4—C10—C11107.50 (13)H18A—C18—H18B108.7
C9—C10—C11108.51 (15)O4—C19—C20107.43 (16)
C1—C10—C11110.94 (14)O4—C19—C18108.60 (14)
C16—C11—C15109.38 (16)C20—C19—C18115.24 (18)
C16—C11—C10109.65 (14)O4—C19—C13107.21 (14)
C15—C11—C10111.66 (17)C20—C19—C13115.23 (17)
C16—C11—C12109.20 (16)C18—C19—C13102.73 (16)
C15—C11—C12111.33 (16)C19—C20—H20A109.5
C10—C11—C12105.53 (14)C19—C20—H20B109.5
C17—C12—C13100.79 (17)H20A—C20—H20B109.5
C17—C12—C11115.67 (16)C19—C20—H20C109.5
C13—C12—C11109.02 (15)H20A—C20—H20C109.5
C17—C12—H12110.3H20B—C20—H20C109.5
C13—C12—H12110.3C10—O4—C19113.98 (12)
O1—C1—C2—C31.9 (3)C1—C10—C11—C1570.41 (19)
C10—C1—C2—C3177.07 (17)O4—C10—C11—C1253.98 (17)
O1—C1—C2—C7177.1 (2)C9—C10—C11—C1264.49 (18)
C10—C1—C2—C73.9 (3)C1—C10—C11—C12168.48 (15)
C7—C2—C3—C40.5 (3)C16—C11—C12—C1717.4 (2)
C1—C2—C3—C4178.54 (19)C15—C11—C12—C17138.31 (18)
C2—C3—C4—C50.3 (3)C10—C11—C12—C17100.37 (18)
C3—C4—C5—C60.2 (4)C16—C11—C12—C13130.10 (17)
C4—C5—C6—C70.5 (4)C15—C11—C12—C13109.02 (19)
C3—C2—C7—C60.3 (3)C10—C11—C12—C1312.3 (2)
C1—C2—C7—C6178.76 (19)C17—C12—C13—C14167.05 (16)
C3—C2—C7—C8178.6 (2)C11—C12—C13—C1444.9 (2)
C1—C2—C7—C80.4 (3)C17—C12—C13—C1950.10 (16)
C5—C6—C7—C20.3 (3)C11—C12—C13—C1972.05 (19)
C5—C6—C7—C8178.1 (2)C8—C9—C14—C13177.3 (2)
C2—C7—C8—O2179.7 (3)C10—C9—C14—C130.4 (3)
C6—C7—C8—O21.4 (4)C12—C13—C14—C954.9 (2)
C2—C7—C8—C90.3 (3)C19—C13—C14—C955.1 (2)
C6—C7—C8—C9178.6 (2)C15—C11—C16—O313.7 (3)
O2—C8—C9—C141.8 (5)C10—C11—C16—O3136.5 (2)
C7—C8—C9—C14178.2 (2)C12—C11—C16—O3108.3 (3)
O2—C8—C9—C10175.6 (3)C13—C12—C17—C1835.32 (18)
C7—C8—C9—C104.4 (3)C11—C12—C17—C1882.0 (2)
C14—C9—C10—O456.0 (2)C12—C17—C18—C196.2 (2)
C8—C9—C10—O4126.4 (2)C17—C18—C19—O488.02 (18)
C14—C9—C10—C1174.09 (18)C17—C18—C19—C20151.45 (18)
C8—C9—C10—C18.2 (3)C17—C18—C19—C1325.31 (19)
C14—C9—C10—C1161.2 (2)C14—C13—C19—O451.98 (19)
C8—C9—C10—C11116.5 (2)C12—C13—C19—O467.71 (17)
O1—C1—C10—O452.6 (2)C14—C13—C19—C2067.5 (2)
C2—C1—C10—O4128.35 (16)C12—C13—C19—C20172.78 (18)
O1—C1—C10—C9173.2 (2)C14—C13—C19—C18166.33 (15)
C2—C1—C10—C97.8 (2)C12—C13—C19—C1846.64 (17)
O1—C1—C10—C1163.3 (3)C9—C10—O4—C1956.08 (19)
C2—C1—C10—C11115.71 (18)C1—C10—O4—C19179.97 (14)
O4—C10—C11—C1663.52 (17)C11—C10—O4—C1961.68 (16)
C9—C10—C11—C16178.00 (16)C20—C19—O4—C10127.16 (17)
C1—C10—C11—C1650.98 (19)C18—C19—O4—C10107.58 (16)
O4—C10—C11—C15175.09 (15)C13—C19—O4—C102.77 (19)
C9—C10—C11—C1556.61 (19)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C5—H5···O1i0.932.553.381 (3)148
C13—H13···O3ii0.982.473.268 (3)138
Symmetry codes: (i) x+2, y, z1/2; (ii) x, y+1, z.
 

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