ent-3β,16-Dihydroxy­isopimar-7-ene-2,15-dione: a new tricyclic diterpenoid from the roots of Euphorbia wallichii

The title compound, C₂₀H₃₀O₄, is an ent-isopimarane diterpenoid which was isolated from the roots of Euphorbia wallichii. The mol­ecule contains three six-membered rings, which adopt chair and half-chair conformations. In addition to an intra­molecular O—H...O hydrogen bond, an inter­molecular O—H...O hydrogen bond connects the mol­ecules into chains.

Key indicators

• Single-crystal X-ray study
• T = 296 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.043
• wR factor = 0.101
• Data-to-parameter ratio = 9.0

checkCIF/PLATON results

No syntax errors found



Alert level C
CELLV02_ALERT_1_C  The supplied cell volume s.u. differs from that
            calculated from the cell parameter s.u.'s by > 2
            Calculated cell volume su =      38.08
            Cell volume su given      =      36.00
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C15
PLAT731_ALERT_1_C Bond    Calc     0.82(4), Rep   0.818(10) ......       4.00 su-Rat
              O2   -H2O     1.555   1.555

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           26.99
           From the CIF: _reflns_number_total               2077
           Count of symmetry unique reflns         2074
           Completeness (_total/calc)            100.14%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured         3
           Fraction of Friedel pairs measured     0.001
           Are heavy atom types Z>Si present         no

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   4 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   2 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
   0 ALERT type 3 Indicator that the structure quality may be low
   2 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: XSCANS (Siemens, 1994); cell refinement: XSCANS; data reduction: SHELXTL (Siemens, 1994); program(s) used to solve structure: SHELXTL; program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

ent-3β,16-Dihydroxyisopimar-7-ene-2,15-dione

Crystal data

C20H30O4	Dx = 1.234 Mg m^−3
Mr = 334.44	Melting point = 529–531 K
Monoclinic, P21	Mo Kα radiation, λ = 0.71073 Å
a = 9.238 (2) Å	Cell parameters from 29 reflections
b = 10.124 (3) Å	θ = 3.5–14.5°
c = 9.696 (2) Å	µ = 0.08 mm^−1
β = 97.03 (2)°	T = 296 K
V = 900.0 (4) Å^3	Prism, colourless
Z = 2	0.60 × 0.54 × 0.24 mm
F(000) = 364

Data collection

Siemens P4 diffractometer	Rint = 0.016
Radiation source: normal-focus sealed tube	θmax = 27.0°, θmin = 2.1°
Graphite monochromator	h = 0→11
ω scans	k = 0→12
2281 measured reflections	l = −12→12
2077 independent reflections	3 standard reflections every 97 reflections
1419 reflections with I > 2σ(I)	intensity decay: 3.1%

Refinement

Refinement on F^2	Hydrogen site location: inferred from neighbouring sites
Least-squares matrix: full	H atoms treated by a mixture of independent and constrained refinement
R[F^2 > 2σ(F^2)] = 0.043	w = 1/[σ^2(Fo^2) + (0.0526P)^2] where P = (Fo^2 + 2Fc^2)/3
wR(F^2) = 0.102	(Δ/σ)max < 0.001
S = 0.93	Δρmax = 0.16 e Å^−3
2077 reflections	Δρmin = −0.14 e Å^−3
230 parameters	Extinction correction: SHELXTL, Fc^*=kFc[1+0.001xFc^2λ^3/sin(2θ)]^-1/4
3 restraints	Extinction coefficient: 0.011 (3)
Primary atom site location: structure-invariant direct methods	Absolute structure: calculation of Flack Parameter suppressed
Secondary atom site location: difference Fourier map

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
O1	0.2998 (3)	−0.0751 (3)	0.8398 (3)	0.0835 (9)
O2	0.1608 (3)	−0.0515 (3)	1.0622 (3)	0.0692 (7)
O3	0.1785 (3)	0.7028 (3)	0.2864 (2)	0.0760 (8)
O4	0.1908 (4)	0.9572 (3)	0.3671 (3)	0.0878 (10)
C1	0.2166 (4)	0.1299 (3)	0.7356 (3)	0.0502 (8)
H1A	0.1152	0.1355	0.6960	0.060*
H1B	0.2732	0.1042	0.6621	0.060*
C2	0.2318 (4)	0.0266 (3)	0.8453 (3)	0.0545 (9)
C3	0.1519 (4)	0.0559 (3)	0.9685 (3)	0.0495 (8)
H3	0.0488	0.0692	0.9337	0.059*
C4	0.2098 (3)	0.1861 (3)	1.0401 (3)	0.0408 (7)
C5	0.2026 (3)	0.2963 (3)	0.9281 (3)	0.0354 (7)
H5	0.0984	0.3111	0.8998	0.042*
C6	0.2612 (3)	0.4290 (3)	0.9870 (3)	0.0422 (7)
H6A	0.2062	0.4558	1.0613	0.051*
H6B	0.3623	0.4186	1.0260	0.051*
C7	0.2505 (3)	0.5348 (3)	0.8774 (3)	0.0409 (7)
H7	0.2641	0.6220	0.9063	0.049*
C8	0.2231 (3)	0.5117 (3)	0.7437 (3)	0.0358 (7)
C9	0.2062 (3)	0.3728 (3)	0.6848 (3)	0.0374 (7)
H9	0.1010	0.3564	0.6677	0.045*
C10	0.2682 (3)	0.2678 (3)	0.7908 (3)	0.0364 (7)
C11	0.2635 (4)	0.3604 (3)	0.5418 (3)	0.0576 (9)
H11A	0.3691	0.3556	0.5560	0.069*
H11B	0.2274	0.2787	0.4980	0.069*
C12	0.2174 (4)	0.4759 (3)	0.4438 (3)	0.0562 (10)
H12A	0.2602	0.4647	0.3581	0.067*
H12B	0.1121	0.4753	0.4212	0.067*
C13	0.2648 (3)	0.6074 (3)	0.5087 (3)	0.0390 (7)
C14	0.1931 (3)	0.6243 (3)	0.6420 (3)	0.0433 (7)
H14A	0.2278	0.7058	0.6873	0.052*
H14B	0.0885	0.6325	0.6174	0.052*
C15	0.2173 (3)	0.7208 (3)	0.4075 (3)	0.0436 (7)
C16	0.2237 (5)	0.8581 (3)	0.4626 (4)	0.0664 (11)
H16A	0.1570	0.8646	0.5322	0.080*
H16B	0.3212	0.8736	0.5092	0.080*
C17	0.4315 (3)	0.6156 (4)	0.5418 (4)	0.0611 (9)
H17A	0.4640	0.5539	0.6142	0.073*
H17B	0.4589	0.7034	0.5719	0.073*
H17C	0.4759	0.5947	0.4600	0.073*
C18	0.1067 (4)	0.2227 (4)	1.1466 (3)	0.0600 (9)
H18A	0.0142	0.2497	1.0988	0.072*
H18B	0.1482	0.2939	1.2037	0.072*
H18C	0.0932	0.1474	1.2038	0.072*
C19	0.3617 (4)	0.1596 (4)	1.1180 (3)	0.0578 (9)
H19A	0.3532	0.1014	1.1949	0.069*
H19B	0.4048	0.2414	1.1519	0.069*
H19C	0.4221	0.1192	1.0560	0.069*
C20	0.4359 (3)	0.2698 (3)	0.8116 (3)	0.0494 (8)
H20A	0.4694	0.3564	0.8405	0.059*
H20B	0.4719	0.2476	0.7257	0.059*
H20C	0.4712	0.2065	0.8815	0.059*
H2O	0.211 (4)	−0.105 (4)	1.026 (5)	0.096 (19)*
H4O	0.183 (5)	0.928 (5)	0.288 (2)	0.107 (19)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.138 (3)	0.0378 (14)	0.0746 (18)	0.0162 (17)	0.0115 (16)	0.0018 (14)
O2	0.096 (2)	0.0453 (16)	0.0648 (16)	−0.0141 (16)	0.0063 (15)	0.0173 (14)
O3	0.123 (2)	0.0619 (17)	0.0386 (12)	0.0043 (16)	−0.0066 (13)	0.0110 (13)
O4	0.152 (3)	0.0442 (18)	0.0654 (18)	−0.0022 (17)	0.0054 (18)	0.0215 (15)
C1	0.071 (2)	0.0358 (18)	0.0421 (17)	−0.0035 (17)	0.0019 (15)	0.0011 (15)
C2	0.080 (2)	0.0277 (17)	0.053 (2)	−0.0096 (17)	−0.0044 (18)	−0.0003 (15)
C3	0.059 (2)	0.0397 (19)	0.0476 (18)	−0.0095 (15)	−0.0022 (15)	0.0154 (15)
C4	0.0439 (17)	0.0399 (17)	0.0387 (15)	−0.0021 (14)	0.0062 (12)	0.0071 (14)
C5	0.0330 (15)	0.0386 (17)	0.0349 (15)	0.0000 (12)	0.0053 (12)	0.0063 (13)
C6	0.0555 (18)	0.0356 (15)	0.0366 (15)	−0.0005 (15)	0.0102 (13)	−0.0014 (14)
C7	0.0532 (18)	0.0278 (15)	0.0444 (17)	−0.0056 (14)	0.0165 (13)	−0.0038 (14)
C8	0.0386 (16)	0.0320 (16)	0.0390 (15)	0.0013 (13)	0.0145 (13)	0.0047 (13)
C9	0.0433 (17)	0.0338 (15)	0.0354 (14)	−0.0031 (13)	0.0059 (12)	0.0018 (13)
C10	0.0442 (17)	0.0294 (15)	0.0357 (15)	0.0019 (13)	0.0051 (13)	0.0038 (13)
C11	0.096 (3)	0.0399 (18)	0.0381 (16)	0.0023 (18)	0.0154 (16)	0.0014 (15)
C12	0.087 (3)	0.050 (2)	0.0325 (16)	−0.0079 (18)	0.0111 (17)	0.0020 (16)
C13	0.0405 (16)	0.0417 (17)	0.0360 (15)	−0.0008 (14)	0.0098 (12)	0.0060 (14)
C14	0.0538 (19)	0.0362 (17)	0.0418 (16)	0.0029 (15)	0.0133 (13)	0.0051 (15)
C15	0.0405 (17)	0.0496 (19)	0.0417 (16)	−0.0016 (15)	0.0087 (13)	0.0096 (15)
C16	0.092 (3)	0.044 (2)	0.059 (2)	−0.0041 (19)	−0.009 (2)	0.0108 (19)
C17	0.0459 (19)	0.076 (3)	0.0622 (19)	0.0052 (19)	0.0093 (15)	0.021 (2)
C18	0.078 (2)	0.056 (2)	0.0512 (18)	0.0030 (19)	0.0288 (17)	0.0171 (17)
C19	0.059 (2)	0.056 (2)	0.0540 (18)	−0.0061 (17)	−0.0082 (15)	0.0168 (17)
C20	0.0500 (18)	0.0507 (18)	0.0502 (17)	0.0085 (15)	0.0170 (14)	0.0043 (16)

Geometric parameters (Å, º)

O1—C2	1.211 (4)	C9—H9	0.9800
O2—C3	1.413 (4)	C10—C20	1.538 (4)
O2—H2O	0.818 (10)	C11—C12	1.533 (4)
O3—C15	1.199 (3)	C11—H11A	0.9700
O4—C16	1.374 (4)	C11—H11B	0.9700
O4—H4O	0.819 (10)	C12—C13	1.515 (4)
C1—C2	1.486 (4)	C12—H12A	0.9700
C1—C10	1.549 (4)	C12—H12B	0.9700
C1—H1A	0.9700	C13—C14	1.533 (4)
C1—H1B	0.9700	C13—C17	1.536 (4)
C2—C3	1.508 (5)	C13—C15	1.538 (4)
C3—C4	1.554 (4)	C14—H14A	0.9700
C3—H3	0.9800	C14—H14B	0.9700
C4—C18	1.533 (4)	C15—C16	1.488 (5)
C4—C19	1.534 (4)	C16—H16A	0.9700
C4—C5	1.553 (4)	C16—H16B	0.9700
C5—C6	1.532 (4)	C17—H17A	0.9600
C5—C10	1.555 (4)	C17—H17B	0.9600
C5—H5	0.9800	C17—H17C	0.9600
C6—C7	1.504 (4)	C18—H18A	0.9600
C6—H6A	0.9700	C18—H18B	0.9600
C6—H6B	0.9700	C18—H18C	0.9600
C7—C8	1.312 (4)	C19—H19A	0.9600
C7—H7	0.9300	C19—H19B	0.9600
C8—C14	1.510 (4)	C19—H19C	0.9600
C8—C9	1.518 (4)	C20—H20A	0.9600
C9—C10	1.540 (4)	C20—H20B	0.9600
C9—C11	1.549 (4)	C20—H20C	0.9600
C3—O2—H2O	103 (3)	C9—C11—H11A	108.9
C16—O4—H4O	111 (4)	C12—C11—H11B	108.9
C2—C1—C10	112.9 (2)	C9—C11—H11B	108.9
C2—C1—H1A	109.0	H11A—C11—H11B	107.8
C10—C1—H1A	109.0	C13—C12—C11	111.6 (2)
C2—C1—H1B	109.0	C13—C12—H12A	109.3
C10—C1—H1B	109.0	C11—C12—H12A	109.3
H1A—C1—H1B	107.8	C13—C12—H12B	109.3
O1—C2—C1	124.8 (3)	C11—C12—H12B	109.3
O1—C2—C3	120.6 (3)	H12A—C12—H12B	108.0
C1—C2—C3	114.6 (3)	C12—C13—C14	108.4 (2)
O2—C3—C2	111.3 (3)	C14—C13—C17	110.1 (2)
O2—C3—C4	112.0 (2)	C12—C13—C15	110.2 (2)
C2—C3—C4	110.2 (2)	C14—C13—C15	109.6 (2)
O2—C3—H3	107.7	C17—C13—C15	107.1 (2)
C2—C3—H3	107.7	C8—C14—C13	113.7 (2)
C4—C3—H3	107.7	C8—C14—H14A	108.8
C18—C4—C19	108.5 (2)	C13—C14—H14A	108.8
C18—C4—C5	108.7 (2)	C8—C14—H14B	108.8
C19—C4—C5	115.4 (2)	C13—C14—H14B	108.8
C18—C4—C3	107.3 (3)	H14A—C14—H14B	107.7
C19—C4—C3	108.4 (3)	O3—C15—C16	119.2 (3)
C5—C4—C3	108.3 (2)	O3—C15—C13	122.6 (3)
C6—C5—C4	112.7 (2)	C16—C15—C13	118.2 (3)
C6—C5—C10	109.0 (2)	O4—C16—C15	116.4 (3)
C4—C5—C10	118.5 (2)	O4—C16—H16A	108.2
C6—C5—H5	105.1	C15—C16—H16A	108.2
C4—C5—H5	105.1	O4—C16—H16B	108.2
C10—C5—H5	105.1	C15—C16—H16B	108.2
C7—C6—C5	111.8 (2)	H16A—C16—H16B	107.3
C7—C6—H6A	109.3	C13—C17—H17A	109.5
C5—C6—H6A	109.3	C13—C17—H17B	109.5
C7—C6—H6B	109.3	H17A—C17—H17B	109.5
C5—C6—H6B	109.3	C13—C17—H17C	109.5
H6A—C6—H6B	107.9	H17A—C17—H17C	109.5
C8—C7—C6	124.0 (3)	H17B—C17—H17C	109.5
C8—C7—H7	118.0	C4—C18—H18A	109.5
C6—C7—H7	118.0	C4—C18—H18B	109.5
C7—C8—C14	120.5 (3)	H18A—C18—H18B	109.5
C7—C8—C9	122.4 (2)	C4—C18—H18C	109.5
C14—C8—C9	116.9 (2)	H18A—C18—H18C	109.5
C8—C9—C10	112.1 (2)	H18B—C18—H18C	109.5
C8—C9—C11	112.4 (2)	C4—C19—H19A	109.5
C10—C9—C11	113.7 (2)	C4—C19—H19B	109.5
C8—C9—H9	106.0	H19A—C19—H19B	109.5
C10—C9—H9	106.0	C4—C19—H19C	109.5
C11—C9—H9	106.0	H19A—C19—H19C	109.5
C20—C10—C9	111.4 (2)	H19B—C19—H19C	109.5
C20—C10—C1	108.6 (2)	C10—C20—H20A	109.5
C9—C10—C1	108.6 (2)	C10—C20—H20B	109.5
C20—C10—C5	112.2 (2)	H20A—C20—H20B	109.5
C9—C10—C5	106.9 (2)	C10—C20—H20C	109.5
C1—C10—C5	109.1 (2)	H20A—C20—H20C	109.5
C12—C11—C9	113.1 (3)	H20B—C20—H20C	109.5
C12—C11—H11A	108.9
C10—C1—C2—O1	−123.8 (4)	C8—C9—C10—C5	49.9 (3)
C10—C1—C2—C3	57.2 (4)	C11—C9—C10—C5	178.8 (3)
O1—C2—C3—O2	−4.2 (4)	C2—C1—C10—C20	75.8 (4)
C1—C2—C3—O2	174.9 (3)	C2—C1—C10—C9	−162.9 (3)
O1—C2—C3—C4	120.8 (4)	C2—C1—C10—C5	−46.7 (3)
C1—C2—C3—C4	−60.2 (3)	C6—C5—C10—C20	56.2 (3)
O2—C3—C4—C18	−65.5 (4)	C4—C5—C10—C20	−74.4 (3)
C2—C3—C4—C18	170.0 (3)	C6—C5—C10—C9	−66.2 (3)
O2—C3—C4—C19	51.5 (4)	C4—C5—C10—C9	163.2 (2)
C2—C3—C4—C19	−73.0 (3)	C6—C5—C10—C1	176.6 (2)
O2—C3—C4—C5	177.3 (3)	C4—C5—C10—C1	45.9 (3)
C2—C3—C4—C5	52.8 (3)	C8—C9—C11—C12	−43.6 (4)
C18—C4—C5—C6	65.2 (3)	C10—C9—C11—C12	−172.3 (3)
C19—C4—C5—C6	−56.9 (3)	C9—C11—C12—C13	56.2 (4)
C3—C4—C5—C6	−178.5 (2)	C11—C12—C13—C14	−60.3 (3)
C18—C4—C5—C10	−165.9 (3)	C11—C12—C13—C17	61.0 (3)
C19—C4—C5—C10	72.1 (3)	C11—C12—C13—C15	179.8 (3)
C3—C4—C5—C10	−49.5 (3)	C7—C8—C14—C13	139.4 (3)
C4—C5—C6—C7	−178.9 (2)	C9—C8—C14—C13	−46.0 (3)
C10—C5—C6—C7	47.4 (3)	C12—C13—C14—C8	55.0 (3)
C5—C6—C7—C8	−13.1 (4)	C17—C13—C14—C8	−67.2 (3)
C6—C7—C8—C14	171.3 (3)	C15—C13—C14—C8	175.3 (2)
C6—C7—C8—C9	−3.0 (5)	C12—C13—C15—O3	−15.1 (4)
C7—C8—C9—C10	−16.8 (4)	C14—C13—C15—O3	−134.3 (3)
C14—C8—C9—C10	168.7 (2)	C17—C13—C15—O3	106.3 (4)
C7—C8—C9—C11	−146.4 (3)	C12—C13—C15—C16	166.5 (3)
C14—C8—C9—C11	39.2 (4)	C14—C13—C15—C16	47.3 (4)
C8—C9—C10—C20	−72.9 (3)	C17—C13—C15—C16	−72.1 (4)
C11—C9—C10—C20	56.0 (3)	O3—C15—C16—O4	−3.2 (5)
C8—C9—C10—C1	167.6 (2)	C13—C15—C16—O4	175.3 (3)
C11—C9—C10—C1	−63.6 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4O···O2^i	0.82 (1)	2.18 (3)	2.936 (4)	153 (5)

Symmetry code: (i) x, y+1, z−1.