8α,9α-Ep­oxy-7-oxoroyleanon

The title compound, C₂₀H₂₆O₅, is a naturally occurring diterpenoid epoxy­quinone. Its geometrical parameters are normal. The hydr­oxy group forms an inter­molecular O—H...O hydrogen bond which links the mol­ecules into infinite chains extended along the b axis.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.006 Å
• R factor = 0.060
• wR factor = 0.152
• Data-to-parameter ratio = 9.1

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT241_ALERT_2_C Check High      Ueq as Compared to Neighbors for         C6
PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ...          6
PLAT412_ALERT_2_C Short Intra XH3 .. XHn     H19B   ..  H20A    ..       1.86 Ang.

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           27.10
           From the CIF: _reflns_number_total               2066
           Count of symmetry unique reflns         2118
           Completeness (_total/calc)             97.54%
           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
   2 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

Data collection: DENZO (Otwinowski & Minor, 1997); cell refinement: SCALEPACK (Otwinowski & Minor, 1997); data reduction: SCALEPACK; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEPII (Johnson, 1976) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.

8α,9α-Epoxy-7-oxoroyleanon

Crystal data

C20H26O5	F(000) = 372
Mr = 346.41	Dx = 1.292 Mg m^−3
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2yb	Cell parameters from 5289 reflections
a = 10.336 (2) Å	θ = 2.4–27.1°
b = 7.4770 (15) Å	µ = 0.09 mm^−1
c = 11.760 (2) Å	T = 296 K
β = 101.61 (3)°	Block, yellow
V = 890.2 (3) Å^3	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection

MAC DIP 2030K diffractometer	1845 reflections with I > 2σ(I)
Radiation source: rotating anode	Rint = 0.038
Graphite monochromator	θmax = 27.1°, θmin = 2.4°
ω scans	h = −13→13
5289 measured reflections	k = −9→9
2066 independent reflections	l = −15→14

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F^2 > 2σ(F^2)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.152	H-atom parameters constrained
S = 1.09	w = 1/[σ^2(Fo^2) + (0.071P)^2 + 0.3757P] where P = (Fo^2 + 2Fc^2)/3
2066 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.25 e Å^−3
1 restraint	Δρmin = −0.18 e Å^−3

Special details

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 (Ų)

	x	y	z	Uiso*/Ueq
C1	0.5603 (4)	0.5027 (6)	−0.1434 (3)	0.0601 (10)
H1A	0.5932	0.3828	−0.1237	0.072*
H1B	0.5013	0.5338	−0.0919	0.072*
C2	0.4829 (5)	0.5047 (7)	−0.2694 (4)	0.0724 (13)
H2A	0.5398	0.4633	−0.3203	0.087*
H2B	0.4089	0.4229	−0.2769	0.087*
C3	0.4323 (4)	0.6895 (8)	−0.3067 (4)	0.0660 (12)
H3A	0.3693	0.7257	−0.2602	0.079*
H3B	0.3861	0.6848	−0.3871	0.079*
C4	0.5423 (4)	0.8313 (6)	−0.2948 (3)	0.0548 (9)
C5	0.6237 (3)	0.8211 (5)	−0.1668 (3)	0.0456 (8)
H5A	0.5595	0.8498	−0.1184	0.055*
C6	0.7271 (5)	0.9698 (7)	−0.1404 (3)	0.0694 (13)
H6A	0.7746	0.9755	−0.2035	0.083*
H6B	0.6817	1.0830	−0.1385	0.083*
C7	0.8254 (4)	0.9487 (6)	−0.0286 (3)	0.0536 (9)
C8	0.7966 (3)	0.8170 (5)	0.0587 (3)	0.0412 (7)
C9	0.7334 (3)	0.6482 (5)	0.0077 (3)	0.0406 (7)
C10	0.6777 (3)	0.6346 (5)	−0.1240 (3)	0.0417 (8)
C11	0.7819 (4)	0.4836 (6)	0.0789 (3)	0.0474 (8)
C12	0.8710 (4)	0.5051 (5)	0.1954 (3)	0.0461 (8)
C13	0.9102 (4)	0.6617 (6)	0.2471 (3)	0.0467 (8)
C14	0.8759 (3)	0.8261 (6)	0.1823 (3)	0.0442 (8)
C15	0.9810 (4)	0.6684 (7)	0.3734 (3)	0.0607 (10)
H15A	0.9994	0.5434	0.3961	0.073*
C16	0.8894 (5)	0.7348 (9)	0.4491 (4)	0.0799 (17)
H16A	0.9356	0.7379	0.5285	0.120*
H16B	0.8149	0.6558	0.4419	0.120*
H16C	0.8593	0.8529	0.4250	0.120*
C17	1.1124 (4)	0.7584 (9)	0.3949 (4)	0.0761 (14)
H17A	1.1497	0.7570	0.4766	0.114*
H17B	1.1020	0.8799	0.3682	0.114*
H17C	1.1701	0.6963	0.3538	0.114*
C18	0.4767 (6)	1.0156 (8)	−0.3122 (5)	0.0850 (17)
H18A	0.4262	1.0248	−0.3900	0.127*
H18B	0.5434	1.1068	−0.2995	0.127*
H18C	0.4193	1.0308	−0.2581	0.127*
C19	0.6226 (5)	0.8076 (9)	−0.3901 (3)	0.0745 (14)
H19A	0.5648	0.8153	−0.4648	0.112*
H19B	0.6651	0.6929	−0.3819	0.112*
H19C	0.6883	0.9000	−0.3832	0.112*
C20	0.7906 (4)	0.5657 (8)	−0.1790 (3)	0.0662 (13)
H20A	0.7606	0.5558	−0.2615	0.099*
H20B	0.8185	0.4504	−0.1473	0.099*
H20C	0.8634	0.6477	−0.1626	0.099*
O21	0.9324 (3)	1.0220 (6)	−0.0125 (3)	0.0772 (10)
O22	0.6612 (2)	0.7711 (4)	0.0659 (2)	0.0488 (6)
O23	0.7526 (3)	0.3336 (4)	0.0465 (3)	0.0703 (9)
O24	0.9033 (3)	0.3505 (4)	0.2517 (2)	0.0622 (8)
H24A	0.8703	0.2670	0.2107	0.093*
O25	0.8999 (3)	0.9757 (4)	0.2247 (2)	0.0606 (8)

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
C1	0.063 (2)	0.055 (2)	0.053 (2)	−0.016 (2)	−0.0118 (17)	0.0048 (19)
C2	0.067 (3)	0.066 (3)	0.069 (3)	−0.016 (2)	−0.023 (2)	0.005 (2)
C3	0.0452 (19)	0.083 (3)	0.060 (2)	−0.002 (2)	−0.0131 (16)	0.008 (2)
C4	0.060 (2)	0.055 (2)	0.0413 (17)	0.007 (2)	−0.0084 (14)	0.0052 (18)
C5	0.0489 (17)	0.048 (2)	0.0361 (15)	0.0046 (17)	−0.0003 (12)	0.0018 (15)
C6	0.092 (3)	0.058 (3)	0.047 (2)	−0.021 (2)	−0.013 (2)	0.010 (2)
C7	0.065 (2)	0.050 (2)	0.0436 (18)	−0.0144 (19)	0.0050 (16)	0.0002 (17)
C8	0.0428 (16)	0.0426 (19)	0.0354 (15)	−0.0028 (15)	0.0010 (12)	0.0004 (14)
C9	0.0410 (15)	0.0418 (18)	0.0366 (16)	0.0028 (15)	0.0019 (12)	−0.0002 (14)
C10	0.0417 (16)	0.046 (2)	0.0340 (15)	0.0028 (14)	−0.0012 (12)	−0.0024 (14)
C11	0.0509 (19)	0.046 (2)	0.0425 (17)	−0.0007 (17)	0.0029 (14)	−0.0019 (16)
C12	0.0477 (17)	0.047 (2)	0.0401 (17)	0.0042 (17)	0.0006 (14)	0.0037 (16)
C13	0.0485 (18)	0.052 (2)	0.0368 (17)	−0.0017 (18)	0.0028 (14)	0.0007 (16)
C14	0.0455 (16)	0.048 (2)	0.0377 (16)	−0.0012 (17)	0.0053 (13)	−0.0040 (15)
C15	0.077 (3)	0.058 (2)	0.0399 (18)	−0.002 (2)	−0.0067 (17)	0.0035 (19)
C16	0.080 (3)	0.116 (5)	0.045 (2)	−0.032 (3)	0.0162 (19)	−0.020 (3)
C17	0.056 (2)	0.102 (4)	0.064 (2)	−0.001 (3)	−0.0056 (18)	−0.007 (3)
C18	0.100 (4)	0.074 (3)	0.067 (3)	0.030 (3)	−0.016 (3)	0.012 (3)
C19	0.080 (3)	0.099 (4)	0.0387 (18)	0.001 (3)	−0.0018 (17)	0.008 (2)
C20	0.056 (2)	0.097 (4)	0.0423 (18)	0.025 (2)	0.0020 (16)	−0.010 (2)
O21	0.0695 (18)	0.094 (3)	0.0645 (17)	−0.0275 (19)	0.0041 (14)	0.0131 (18)
O22	0.0502 (13)	0.0533 (15)	0.0429 (12)	0.0029 (12)	0.0092 (10)	−0.0047 (12)
O23	0.098 (2)	0.0409 (15)	0.0573 (17)	−0.0057 (17)	−0.0207 (15)	−0.0002 (13)
O24	0.083 (2)	0.0443 (14)	0.0480 (15)	0.0025 (15)	−0.0127 (13)	0.0021 (13)
O25	0.082 (2)	0.0460 (16)	0.0466 (14)	−0.0063 (15)	−0.0051 (13)	−0.0062 (13)

Geometric parameters (Å, º)

C1—C2	1.536 (5)	C10—C20	1.533 (5)
C1—C10	1.544 (5)	C11—O23	1.204 (5)
C1—H1A	0.9700	C11—C12	1.498 (5)
C1—H1B	0.9700	C12—O24	1.341 (5)
C2—C3	1.511 (8)	C12—C13	1.343 (6)
C2—H2A	0.9700	C13—C14	1.452 (6)
C2—H2B	0.9700	C13—C15	1.519 (5)
C3—C4	1.540 (7)	C14—O25	1.229 (5)
C3—H3A	0.9700	C15—C17	1.491 (6)
C3—H3B	0.9700	C15—C16	1.508 (7)
C4—C18	1.532 (7)	C15—H15A	0.9800
C4—C19	1.534 (6)	C16—H16A	0.9600
C4—C5	1.572 (4)	C16—H16B	0.9600
C5—C6	1.530 (6)	C16—H16C	0.9600
C5—C10	1.547 (5)	C17—H17A	0.9600
C5—H5A	0.9800	C17—H17B	0.9600
C6—C7	1.499 (5)	C17—H17C	0.9600
C6—H6A	0.9700	C18—H18A	0.9600
C6—H6B	0.9700	C18—H18B	0.9600
C7—O21	1.215 (5)	C18—H18C	0.9600
C7—C8	1.495 (5)	C19—H19A	0.9600
C8—O22	1.460 (4)	C19—H19B	0.9600
C8—C9	1.491 (5)	C19—H19C	0.9600
C8—C14	1.520 (4)	C20—H20A	0.9600
C9—O22	1.441 (4)	C20—H20B	0.9600
C9—C11	1.517 (5)	C20—H20C	0.9600
C9—C10	1.543 (4)	O24—H24A	0.8200
C2—C1—C10	112.1 (3)	C20—C10—C5	114.9 (3)
C2—C1—H1A	109.2	C9—C10—C5	107.7 (3)
C10—C1—H1A	109.2	C1—C10—C5	107.9 (3)
C2—C1—H1B	109.2	O23—C11—C12	117.4 (4)
C10—C1—H1B	109.2	O23—C11—C9	123.1 (3)
H1A—C1—H1B	107.9	C12—C11—C9	119.5 (3)
C3—C2—C1	111.8 (4)	O24—C12—C13	120.4 (3)
C3—C2—H2A	109.3	O24—C12—C11	113.9 (3)
C1—C2—H2A	109.3	C13—C12—C11	125.5 (3)
C3—C2—H2B	109.3	C12—C13—C14	118.8 (3)
C1—C2—H2B	109.3	C12—C13—C15	120.8 (4)
H2A—C2—H2B	107.9	C14—C13—C15	120.3 (4)
C2—C3—C4	113.4 (3)	O25—C14—C13	123.3 (3)
C2—C3—H3A	108.9	O25—C14—C8	117.0 (3)
C4—C3—H3A	108.9	C13—C14—C8	119.4 (3)
C2—C3—H3B	108.9	C17—C15—C16	114.2 (4)
C4—C3—H3B	108.9	C17—C15—C13	115.1 (4)
H3A—C3—H3B	107.7	C16—C15—C13	110.6 (4)
C18—C4—C19	107.2 (4)	C17—C15—H15A	105.3
C18—C4—C3	108.0 (4)	C16—C15—H15A	105.3
C19—C4—C3	110.6 (4)	C13—C15—H15A	105.3
C18—C4—C5	108.0 (4)	C15—C16—H16A	109.5
C19—C4—C5	115.5 (3)	C15—C16—H16B	109.5
C3—C4—C5	107.3 (3)	H16A—C16—H16B	109.5
C6—C5—C10	113.4 (3)	C15—C16—H16C	109.5
C6—C5—C4	112.1 (3)	H16A—C16—H16C	109.5
C10—C5—C4	116.3 (3)	H16B—C16—H16C	109.5
C6—C5—H5A	104.5	C15—C17—H17A	109.5
C10—C5—H5A	104.5	C15—C17—H17B	109.5
C4—C5—H5A	104.5	H17A—C17—H17B	109.5
C7—C6—C5	115.1 (3)	C15—C17—H17C	109.5
C7—C6—H6A	108.5	H17A—C17—H17C	109.5
C5—C6—H6A	108.5	H17B—C17—H17C	109.5
C7—C6—H6B	108.5	C4—C18—H18A	109.5
C5—C6—H6B	108.5	C4—C18—H18B	109.5
H6A—C6—H6B	107.5	H18A—C18—H18B	109.5
O21—C7—C8	119.4 (3)	C4—C18—H18C	109.5
O21—C7—C6	121.7 (4)	H18A—C18—H18C	109.5
C8—C7—C6	118.5 (3)	H18B—C18—H18C	109.5
O22—C8—C9	58.5 (2)	C4—C19—H19A	109.5
O22—C8—C7	121.4 (3)	C4—C19—H19B	109.5
C9—C8—C7	114.4 (3)	H19A—C19—H19B	109.5
O22—C8—C14	107.1 (2)	C4—C19—H19C	109.5
C9—C8—C14	122.1 (3)	H19A—C19—H19C	109.5
C7—C8—C14	118.9 (3)	H19B—C19—H19C	109.5
O22—C9—C8	59.7 (2)	C10—C20—H20A	109.5
O22—C9—C11	113.6 (3)	C10—C20—H20B	109.5
C8—C9—C11	113.3 (3)	H20A—C20—H20B	109.5
O22—C9—C10	113.2 (3)	C10—C20—H20C	109.5
C8—C9—C10	120.3 (3)	H20A—C20—H20C	109.5
C11—C9—C10	121.1 (3)	H20B—C20—H20C	109.5
C20—C10—C9	106.4 (3)	C9—O22—C8	61.8 (2)
C20—C10—C1	111.4 (4)	C12—O24—H24A	109.5
C9—C10—C1	108.3 (3)
C10—C1—C2—C3	−57.2 (5)	C2—C1—C10—C5	53.7 (5)
C1—C2—C3—C4	57.3 (6)	C6—C5—C10—C20	−61.5 (4)
C2—C3—C4—C18	−169.2 (4)	C4—C5—C10—C20	70.8 (4)
C2—C3—C4—C19	73.8 (5)	C6—C5—C10—C9	57.0 (4)
C2—C3—C4—C5	−53.0 (5)	C4—C5—C10—C9	−170.8 (3)
C18—C4—C5—C6	−57.7 (5)	C6—C5—C10—C1	173.6 (3)
C19—C4—C5—C6	62.3 (5)	C4—C5—C10—C1	−54.2 (4)
C3—C4—C5—C6	−173.9 (4)	O22—C9—C11—O23	121.8 (4)
C18—C4—C5—C10	169.5 (4)	C8—C9—C11—O23	−172.5 (4)
C19—C4—C5—C10	−70.5 (5)	C10—C9—C11—O23	−18.1 (6)
C3—C4—C5—C10	53.3 (4)	O22—C9—C11—C12	−58.4 (4)
C10—C5—C6—C7	−34.5 (5)	C8—C9—C11—C12	7.3 (5)
C4—C5—C6—C7	−168.8 (4)	C10—C9—C11—C12	161.6 (3)
C5—C6—C7—O21	157.9 (5)	O23—C11—C12—O24	−2.4 (6)
C5—C6—C7—C8	−14.8 (6)	C9—C11—C12—O24	177.8 (3)
O21—C7—C8—O22	159.1 (4)	O23—C11—C12—C13	−177.6 (4)
C6—C7—C8—O22	−28.1 (6)	C9—C11—C12—C13	2.6 (6)
O21—C7—C8—C9	−134.2 (4)	O24—C12—C13—C14	178.5 (4)
C6—C7—C8—C9	38.6 (5)	C11—C12—C13—C14	−6.6 (6)
O21—C7—C8—C14	22.1 (6)	O24—C12—C13—C15	−5.6 (6)
C6—C7—C8—C14	−165.0 (4)	C11—C12—C13—C15	169.3 (4)
C7—C8—C9—O22	−113.1 (3)	C12—C13—C14—O25	175.1 (4)
C14—C8—C9—O22	91.3 (3)	C15—C13—C14—O25	−0.8 (5)
O22—C8—C9—C11	−104.7 (3)	C12—C13—C14—C8	0.3 (5)
C7—C8—C9—C11	142.2 (3)	C15—C13—C14—C8	−175.7 (3)
C14—C8—C9—C11	−13.3 (4)	O22—C8—C14—O25	−101.8 (4)
O22—C8—C9—C10	100.8 (3)	C9—C8—C14—O25	−164.9 (3)
C7—C8—C9—C10	−12.3 (4)	C7—C8—C14—O25	40.6 (5)
C14—C8—C9—C10	−167.9 (3)	O22—C8—C14—C13	73.3 (4)
O22—C9—C10—C20	157.5 (4)	C9—C8—C14—C13	10.3 (5)
C8—C9—C10—C20	90.2 (4)	C7—C8—C14—C13	−144.2 (4)
C11—C9—C10—C20	−62.4 (5)	C12—C13—C15—C17	124.0 (5)
O22—C9—C10—C1	−82.6 (4)	C14—C13—C15—C17	−60.2 (6)
C8—C9—C10—C1	−149.9 (3)	C12—C13—C15—C16	−104.8 (5)
C11—C9—C10—C1	57.5 (4)	C14—C13—C15—C16	71.1 (5)
O22—C9—C10—C5	33.8 (4)	C11—C9—O22—C8	104.2 (3)
C8—C9—C10—C5	−33.5 (4)	C10—C9—O22—C8	−112.7 (3)
C11—C9—C10—C5	173.9 (3)	C7—C8—O22—C9	101.1 (4)
C2—C1—C10—C20	−73.3 (5)	C14—C8—O22—C9	−117.6 (3)
C2—C1—C10—C9	170.0 (4)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O24—H24A···O25^i	0.82	2.20	2.820 (4)	132

Symmetry code: (i) x, y−1, z.