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The title compound, C18H14O3, also known as 1,2-di­hydro­tanshin­quinone, contains a four-ring system. No classical hydrogen bonds are found in the structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805005581/ww6359sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536805005581/ww6359Isup2.hkl
Contains datablock I

CCDC reference: 270578

Key indicators

  • Single-crystal X-ray study
  • T = 293 K
  • Mean [sigma](C-C) = 0.002 Å
  • R factor = 0.040
  • wR factor = 0.126
  • Data-to-parameter ratio = 15.2

checkCIF/PLATON results

No syntax errors found



Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT333_ALERT_2_C Large Average Benzene C-C Dist. C8 -C14 1.45 Ang. PLAT335_ALERT_2_C Large Benzene C-C Range C8 -C14 0.20 Ang. PLAT369_ALERT_2_C Long C(sp2)-C(sp2) Bond C11 - C12 ... 1.56 Ang. PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C18 PLAT380_ALERT_4_C Check Incorrectly? Oriented X(sp2)-Methyl Moiety C17
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 6 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 3 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: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1998); software used to prepare material for publication: SHELXTL.

8,9-Dihydro-1,6-dimethylphenanthro[1,2-b]furan-10,11-dione top
Crystal data top
C18H14O3Z = 2
Mr = 278.29F(000) = 292.0
Triclinic, P1Dx = 1.382 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9225 (11) ÅCell parameters from 999 reflections
b = 8.0119 (10) Åθ = 2.8–26.0°
c = 11.7565 (14) ŵ = 0.09 mm1
α = 83.979 (2)°T = 293 K
β = 86.251 (2)°Block, red
γ = 64.422 (2)°0.50 × 0.41 × 0.21 mm
V = 669.22 (15) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer
2897 independent reflections
Radiation source: fine-focus sealed tube2409 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.013
φ and ω scansθmax = 27.1°, θmin = 2.8°
Absorption correction: multi-scan
(SADABS; Sheldrick, 1996)
h = 1010
Tmin = 0.955, Tmax = 0.980k = 1010
7564 measured reflectionsl = 1515
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)] = 0.040Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.04 w = 1/[σ2(Fo2) + (0.0731P)2 + 0.1042P]
where P = (Fo2 + 2Fc2)/3
2897 reflections(Δ/σ)max < 0.001
190 parametersΔρmax = 0.26 e Å3
0 restraintsΔρmin = 0.16 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·All H atoms were placed in calculated positions and refined a riding atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
O10.43422 (13)0.76152 (13)1.27599 (8)0.0493 (3)
C80.47464 (16)0.76202 (15)1.06875 (10)0.0372 (3)
C90.58849 (15)0.67123 (15)0.97551 (10)0.0361 (3)
O30.85833 (15)0.39747 (13)0.93063 (9)0.0631 (3)
C100.53361 (16)0.74373 (15)0.86310 (10)0.0371 (3)
C50.35897 (16)0.90082 (16)0.84509 (11)0.0392 (3)
C130.70103 (17)0.53941 (17)1.21521 (11)0.0425 (3)
C110.76294 (16)0.49864 (16)1.00195 (11)0.0405 (3)
O20.97464 (13)0.29844 (14)1.14610 (10)0.0621 (3)
C60.25025 (17)0.98456 (17)0.93923 (11)0.0437 (3)
H6A0.13621.08740.92710.052*
C70.30766 (16)0.91881 (16)1.04920 (11)0.0420 (3)
H7A0.23480.97921.11050.050*
C140.53853 (16)0.68679 (16)1.18276 (11)0.0398 (3)
C10.64998 (17)0.66180 (17)0.75878 (11)0.0438 (3)
H1A0.61880.56530.73690.053*
H1B0.78130.60480.77790.053*
C120.82761 (17)0.43377 (17)1.12817 (12)0.0431 (3)
C40.29400 (18)0.97353 (18)0.72767 (12)0.0463 (3)
C20.61910 (19)0.8060 (2)0.65810 (12)0.0527 (3)
H2A0.68110.88310.67170.063*
H2B0.67480.74380.58950.063*
C30.4168 (2)0.9256 (2)0.63984 (12)0.0551 (4)
H3A0.37460.96800.56570.066*
C160.5374 (2)0.6573 (2)1.36903 (12)0.0540 (3)
H16A0.49850.67891.44460.065*
C150.70083 (19)0.5207 (2)1.33808 (12)0.0498 (3)
C180.0923 (2)1.1035 (2)0.70972 (14)0.0670 (4)
H18A0.07141.13860.62940.101*
H18B0.06101.21240.74930.101*
H18C0.01511.04290.73890.101*
C170.8494 (2)0.3809 (3)1.41446 (15)0.0694 (5)
H17A0.81140.40161.49290.104*
H17B0.96420.39321.39910.104*
H17C0.86810.25821.40040.104*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
O10.0450 (5)0.0482 (5)0.0445 (5)0.0093 (4)0.0057 (4)0.0127 (4)
C80.0319 (6)0.0310 (5)0.0457 (6)0.0105 (5)0.0050 (5)0.0083 (5)
C90.0302 (5)0.0290 (5)0.0461 (6)0.0096 (5)0.0044 (5)0.0085 (4)
O30.0568 (6)0.0440 (5)0.0576 (6)0.0073 (4)0.0112 (5)0.0114 (4)
C100.0315 (5)0.0319 (5)0.0466 (6)0.0120 (5)0.0054 (4)0.0091 (5)
C50.0331 (6)0.0338 (6)0.0470 (7)0.0110 (5)0.0027 (5)0.0050 (5)
C130.0364 (6)0.0404 (6)0.0480 (7)0.0136 (5)0.0006 (5)0.0050 (5)
C110.0329 (6)0.0323 (6)0.0511 (7)0.0091 (5)0.0065 (5)0.0076 (5)
O20.0392 (5)0.0521 (6)0.0709 (7)0.0035 (4)0.0046 (4)0.0058 (5)
C60.0322 (6)0.0331 (6)0.0547 (7)0.0039 (5)0.0044 (5)0.0057 (5)
C70.0347 (6)0.0348 (6)0.0476 (7)0.0065 (5)0.0094 (5)0.0103 (5)
C140.0360 (6)0.0368 (6)0.0440 (6)0.0128 (5)0.0060 (5)0.0099 (5)
C10.0367 (6)0.0416 (6)0.0472 (7)0.0105 (5)0.0055 (5)0.0107 (5)
C120.0322 (6)0.0365 (6)0.0563 (7)0.0104 (5)0.0013 (5)0.0061 (5)
C40.0400 (6)0.0414 (6)0.0506 (7)0.0115 (5)0.0005 (5)0.0018 (5)
C20.0458 (7)0.0575 (8)0.0467 (7)0.0150 (6)0.0100 (6)0.0085 (6)
C30.0509 (8)0.0577 (8)0.0444 (7)0.0131 (6)0.0001 (6)0.0008 (6)
C160.0556 (8)0.0584 (8)0.0423 (7)0.0182 (7)0.0005 (6)0.0089 (6)
C150.0463 (7)0.0526 (7)0.0486 (7)0.0193 (6)0.0035 (5)0.0042 (6)
C180.0473 (8)0.0693 (10)0.0577 (9)0.0013 (7)0.0039 (6)0.0035 (7)
C170.0589 (9)0.0763 (11)0.0592 (9)0.0160 (8)0.0131 (7)0.0020 (8)
Geometric parameters (Å, º) top
O1—C141.3545 (14)C7—H7A0.9300
O1—C161.3779 (17)C1—C21.5174 (19)
C8—C71.3875 (16)C1—H1A0.9700
C8—C91.4198 (15)C1—H1B0.9700
C8—C141.4394 (18)C4—C31.3375 (19)
C9—C101.4032 (17)C4—C181.4982 (19)
C9—C111.4949 (16)C2—C31.4865 (19)
O3—C111.2092 (15)C2—H2A0.9700
C10—C51.4220 (16)C2—H2B0.9700
C10—C11.5111 (16)C3—H3A0.9300
C5—C61.3960 (16)C16—C151.343 (2)
C5—C41.4749 (18)C16—H16A0.9300
C13—C141.3617 (17)C15—C171.495 (2)
C13—C151.4365 (19)C18—H18A0.9600
C13—C121.4434 (17)C18—H18B0.9600
C11—C121.5628 (19)C18—H18C0.9600
O2—C121.2126 (15)C17—H17A0.9600
C6—C71.3722 (18)C17—H17B0.9600
C6—H6A0.9300C17—H17C0.9600
C14—O1—C16105.68 (10)O2—C12—C13125.18 (13)
C7—C8—C9120.37 (11)O2—C12—C11118.76 (11)
C7—C8—C14121.67 (11)C13—C12—C11116.03 (10)
C9—C8—C14117.96 (10)C3—C4—C5119.47 (12)
C10—C9—C8119.60 (10)C3—C4—C18121.40 (13)
C10—C9—C11122.48 (10)C5—C4—C18119.11 (12)
C8—C9—C11117.92 (11)C3—C2—C1111.73 (11)
C9—C10—C5119.00 (10)C3—C2—H2A109.3
C9—C10—C1123.32 (10)C1—C2—H2A109.3
C5—C10—C1117.68 (11)C3—C2—H2B109.3
C6—C5—C10119.45 (11)C1—C2—H2B109.3
C6—C5—C4120.61 (11)H2A—C2—H2B107.9
C10—C5—C4119.94 (11)C4—C3—C2121.47 (13)
C14—C13—C15107.25 (11)C4—C3—H3A119.3
C14—C13—C12118.91 (12)C2—C3—H3A119.3
C15—C13—C12133.77 (12)C15—C16—O1112.25 (12)
O3—C11—C9123.76 (12)C15—C16—H16A123.9
O3—C11—C12115.72 (11)O1—C16—H16A123.9
C9—C11—C12120.46 (10)C16—C15—C13104.55 (12)
C7—C6—C5121.58 (11)C16—C15—C17127.70 (14)
C7—C6—H6A119.2C13—C15—C17127.75 (13)
C5—C6—H6A119.2C4—C18—H18A109.5
C6—C7—C8119.89 (11)C4—C18—H18B109.5
C6—C7—H7A120.1H18A—C18—H18B109.5
C8—C7—H7A120.1C4—C18—H18C109.5
O1—C14—C13110.26 (11)H18A—C18—H18C109.5
O1—C14—C8121.36 (10)H18B—C18—H18C109.5
C13—C14—C8128.38 (11)C15—C17—H17A109.5
C10—C1—C2112.52 (10)C15—C17—H17B109.5
C10—C1—H1A109.1H17A—C17—H17B109.5
C2—C1—H1A109.1C15—C17—H17C109.5
C10—C1—H1B109.1H17A—C17—H17C109.5
C2—C1—H1B109.1H17B—C17—H17C109.5
H1A—C1—H1B107.8
C7—C8—C9—C101.63 (17)C9—C8—C14—O1177.46 (10)
C14—C8—C9—C10178.10 (10)C7—C8—C14—C13177.32 (12)
C7—C8—C9—C11177.60 (10)C9—C8—C14—C132.40 (19)
C14—C8—C9—C112.67 (16)C9—C10—C1—C2151.04 (12)
C8—C9—C10—C53.70 (17)C5—C10—C1—C229.75 (15)
C11—C9—C10—C5175.49 (10)C14—C13—C12—O2178.80 (12)
C8—C9—C10—C1177.10 (10)C15—C13—C12—O22.3 (2)
C11—C9—C10—C13.71 (18)C14—C13—C12—C110.87 (17)
C9—C10—C5—C62.96 (17)C15—C13—C12—C11175.64 (13)
C1—C10—C5—C6177.79 (11)O3—C11—C12—O26.32 (18)
C9—C10—C5—C4176.88 (10)C9—C11—C12—O2176.32 (11)
C1—C10—C5—C42.36 (17)O3—C11—C12—C13171.75 (11)
C10—C9—C11—O38.56 (19)C9—C11—C12—C135.61 (16)
C8—C9—C11—O3170.64 (12)C6—C5—C4—C3162.53 (13)
C10—C9—C11—C12174.30 (10)C10—C5—C4—C317.63 (19)
C8—C9—C11—C126.50 (16)C6—C5—C4—C1815.98 (19)
C10—C5—C6—C70.09 (19)C10—C5—C4—C18163.86 (13)
C4—C5—C6—C7179.76 (11)C10—C1—C2—C346.82 (16)
C5—C6—C7—C82.0 (2)C5—C4—C3—C22.3 (2)
C9—C8—C7—C61.27 (19)C18—C4—C3—C2176.17 (15)
C14—C8—C7—C6179.02 (11)C1—C2—C3—C434.7 (2)
C16—O1—C14—C130.60 (14)C14—O1—C16—C150.22 (16)
C16—O1—C14—C8179.51 (11)O1—C16—C15—C130.23 (16)
C15—C13—C14—O10.75 (15)O1—C16—C15—C17179.60 (14)
C12—C13—C14—O1176.62 (10)C14—C13—C15—C160.58 (15)
C15—C13—C14—C8179.37 (12)C12—C13—C15—C16176.22 (14)
C12—C13—C14—C83.3 (2)C14—C13—C15—C17179.25 (14)
C7—C8—C14—O12.81 (18)C12—C13—C15—C173.9 (3)
 

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