(1R*,4R*,5S*,12S*,13R*)-9-Acetoxy­cembra-8(E),15(17)-dien-16,4-olide monohydrate

The title compound, C₂₀H₃₂O₅.H₂O, crystallizes in the non-centrosymmetric space group C2. The molecular skeleton consists of an irregular 14-membered ring and a nearly twist–boat seven-membered γ-lactone ring with a trans connection. In the solid-state structure, cembradienolide and water mol­ecules form an R₂²(7) motif through O—H...OW and OW—H...O hydrogen bonds, while adjacent mol­ecules form an infinite chain, described by graph-set motif C₂²(12), along the c axis via O—H...O hydrogen bonds.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.004 Å
• R factor = 0.039
• wR factor = 0.111
• Data-to-parameter ratio = 10.1

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H2     ..  H2C     ..       1.83 Ang.

Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT601_ALERT_2_C Structure Contains Solvent Accessible VOIDS of .      48.00 A   3  

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           27.19
           From the CIF: _reflns_number_total               2451
           Count of symmetry unique reflns         2485
           Completeness (_total/calc)             98.63%
           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
   1 ALERT level B = Potentially serious problem
   2 ALERT level C = Check and explain
   1 ALERT level G = General alerts; check

   1 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
   0 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SMART; data reduction: SAINT (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.

(1R*,4R*,5S*,12S*,13R*)-9-Acetoxycembra-8(E),15 (17)-dien-16,4-olide monohydrate

Crystal data

C20H32O5·H2O	F(000) = 808
Mr = 370.47	Dx = 1.161 Mg m^−3
Monoclinic, C2	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C 2y	Cell parameters from 990 reflections
a = 15.6359 (17) Å	θ = 2.6–26.9°
b = 12.1299 (17) Å	µ = 0.08 mm^−1
c = 11.5236 (14) Å	T = 293 K
β = 104.111 (3)°	Block, colorless
V = 2119.6 (5) Å^3	0.50 × 0.50 × 0.48 mm
Z = 4

Data collection

Bruker SMART CCD diffractometer	2451 independent reflections
Radiation source: fine-focus sealed tube	2072 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.039
ω scans	θmax = 27.2°, θmin = 1.8°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→19
Tmin = 0.959, Tmax = 0.961	k = −15→15
9058 measured reflections	l = −14→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.111	H-atom parameters constrained
S = 1.07	w = 1/[σ^2(Fo^2) + (0.0547P)^2 + 0.3649P] where P = (Fo^2 + 2Fc^2)/3
2451 reflections	(Δ/σ)max < 0.001
243 parameters	Δρmax = 0.16 e Å^−3
1 restraint	Δρmin = −0.12 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. All H atoms were placed in calculated positions and refined as riding atoms.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Ų)

	x	y	z	Uiso*/Ueq
O1	0.22465 (19)	−0.08579 (17)	0.86221 (19)	0.0926 (7)
H1	0.2199	−0.0490	0.9200	0.139*
O2	0.30102 (14)	0.52143 (17)	0.94647 (13)	0.0746 (5)
H2	0.2721	0.5771	0.9234	0.112*
O3	0.20161 (13)	0.54837 (16)	0.70284 (15)	0.0696 (5)
H3	0.2283	0.5825	0.6613	0.104*
O4	0.21627 (18)	0.1742 (2)	0.43955 (16)	0.1004 (8)
O5	0.21469 (13)	0.06120 (16)	0.58338 (15)	0.0724 (5)
C1	0.18333 (13)	0.2531 (2)	0.72674 (16)	0.0485 (4)
H1A	0.2439	0.2258	0.7532	0.058*
C2	0.12414 (16)	0.1740 (2)	0.7756 (2)	0.0616 (6)
H2A	0.1534	0.1552	0.8575	0.074*
H2B	0.0697	0.2118	0.7770	0.074*
C3	0.10160 (17)	0.0679 (2)	0.7042 (3)	0.0703 (7)
H3A	0.0726	0.0191	0.7493	0.084*
H3B	0.0588	0.0859	0.6304	0.084*
C4	0.17570 (18)	0.0036 (2)	0.6714 (2)	0.0647 (6)
C5	0.25415 (18)	−0.0172 (2)	0.7795 (2)	0.0660 (6)
H5	0.2728	0.0536	0.8184	0.079*
C6	0.3337 (2)	−0.0709 (3)	0.7479 (3)	0.0844 (9)
H6A	0.3283	−0.0631	0.6626	0.101*
H6B	0.3338	−0.1491	0.7658	0.101*
C7	0.4216 (2)	−0.0203 (3)	0.8162 (3)	0.0946 (11)
H7A	0.4246	−0.0221	0.9013	0.114*
H7B	0.4697	−0.0646	0.8023	0.114*
C8	0.43255 (18)	0.0959 (3)	0.7794 (3)	0.0833 (9)
C9	0.42468 (18)	0.1809 (3)	0.8494 (3)	0.0776 (8)
H9	0.4197	0.1631	0.9260	0.093*
C10	0.42277 (18)	0.3009 (3)	0.8203 (3)	0.0762 (8)
H10A	0.3926	0.3117	0.7370	0.091*
H10B	0.4827	0.3278	0.8317	0.091*
C11	0.37570 (17)	0.3668 (3)	0.8997 (2)	0.0675 (6)
H11A	0.3321	0.3190	0.9209	0.081*
H11B	0.4187	0.3850	0.9732	0.081*
C12	0.32965 (16)	0.4730 (2)	0.84819 (18)	0.0611 (6)
C13	0.24814 (15)	0.4492 (2)	0.74479 (18)	0.0532 (5)
H13	0.2688	0.4170	0.6785	0.064*
C14	0.18172 (15)	0.3693 (2)	0.77715 (19)	0.0543 (5)
H14A	0.1934	0.3645	0.8636	0.065*
H14B	0.1229	0.3995	0.7481	0.065*
C15	0.19602 (17)	0.1595 (2)	0.53340 (19)	0.0624 (6)
C16	0.15829 (13)	0.2496 (2)	0.59139 (18)	0.0543 (5)
C17	0.10737 (17)	0.3228 (3)	0.5219 (2)	0.0731 (7)
H17A	0.0963	0.3166	0.4392	0.088*
H17B	0.0827	0.3804	0.5559	0.088*
C18	0.1410 (3)	−0.1033 (3)	0.6080 (3)	0.0896 (9)
H18A	0.0956	−0.0870	0.5376	0.134*
H18B	0.1173	−0.1488	0.6607	0.134*
H18C	0.1883	−0.1416	0.5857	0.134*
C19	0.4488 (2)	0.1123 (4)	0.6565 (3)	0.1026 (12)
H19A	0.4513	0.1898	0.6405	0.154*
H19B	0.4016	0.0793	0.5975	0.154*
H19C	0.5036	0.0784	0.6534	0.154*
C20	0.3923 (2)	0.5527 (3)	0.8094 (3)	0.0857 (9)
H20A	0.3654	0.6242	0.7960	0.129*
H20B	0.4051	0.5266	0.7368	0.129*
H20C	0.4460	0.5576	0.8710	0.129*
O1W	0.3155 (2)	0.1946 (2)	0.1124 (2)	0.1120 (9)
H1B	0.3190	0.261	0.130	0.134*
H2C	0.3173	0.1551	0.1748	0.134*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.171 (2)	0.0559 (11)	0.0650 (11)	0.0030 (13)	0.0568 (14)	0.0022 (9)
O2	0.1244 (14)	0.0627 (11)	0.0411 (7)	0.0036 (10)	0.0286 (8)	−0.0052 (7)
O3	0.0904 (11)	0.0648 (11)	0.0574 (9)	0.0062 (9)	0.0252 (8)	0.0137 (8)
O4	0.181 (2)	0.0840 (15)	0.0522 (9)	0.0047 (15)	0.0588 (12)	−0.0037 (10)
O5	0.0993 (12)	0.0689 (12)	0.0610 (9)	0.0063 (10)	0.0429 (9)	0.0045 (9)
C1	0.0521 (10)	0.0582 (12)	0.0396 (9)	0.0036 (9)	0.0196 (7)	0.0018 (9)
C2	0.0718 (13)	0.0616 (14)	0.0620 (12)	0.0034 (12)	0.0366 (10)	0.0061 (11)
C3	0.0760 (15)	0.0659 (16)	0.0788 (16)	−0.0106 (13)	0.0379 (12)	0.0036 (13)
C4	0.0829 (15)	0.0592 (14)	0.0600 (13)	−0.0072 (12)	0.0331 (11)	−0.0015 (11)
C5	0.0992 (18)	0.0506 (13)	0.0558 (12)	0.0063 (12)	0.0333 (12)	−0.0018 (11)
C6	0.108 (2)	0.0676 (18)	0.0827 (18)	0.0226 (16)	0.0325 (16)	−0.0076 (15)
C7	0.095 (2)	0.095 (2)	0.091 (2)	0.0433 (19)	0.0168 (17)	−0.0051 (19)
C8	0.0637 (15)	0.100 (2)	0.0833 (18)	0.0210 (15)	0.0119 (13)	−0.0135 (17)
C9	0.0673 (14)	0.095 (2)	0.0636 (14)	0.0171 (15)	0.0029 (11)	−0.0073 (15)
C10	0.0631 (14)	0.097 (2)	0.0687 (16)	0.0040 (15)	0.0152 (12)	−0.0116 (15)
C11	0.0723 (14)	0.0793 (17)	0.0479 (11)	0.0017 (13)	0.0092 (10)	−0.0069 (12)
C12	0.0766 (14)	0.0672 (15)	0.0422 (10)	−0.0044 (12)	0.0199 (10)	−0.0049 (10)
C13	0.0690 (13)	0.0577 (13)	0.0383 (9)	−0.0006 (10)	0.0235 (8)	−0.0011 (9)
C14	0.0612 (12)	0.0604 (14)	0.0474 (10)	0.0050 (10)	0.0249 (9)	−0.0001 (10)
C15	0.0810 (14)	0.0676 (15)	0.0400 (10)	−0.0095 (12)	0.0175 (9)	−0.0055 (10)
C16	0.0566 (11)	0.0662 (14)	0.0415 (9)	−0.0055 (11)	0.0151 (8)	0.0023 (10)
C17	0.0718 (14)	0.090 (2)	0.0555 (13)	0.0004 (14)	0.0126 (11)	0.0122 (13)
C18	0.115 (2)	0.075 (2)	0.0814 (19)	−0.0171 (18)	0.0288 (17)	−0.0170 (16)
C19	0.103 (2)	0.110 (3)	0.107 (3)	0.004 (2)	0.050 (2)	−0.024 (2)
C20	0.0873 (18)	0.099 (2)	0.0697 (15)	−0.0284 (18)	0.0169 (13)	−0.0042 (17)
O1W	0.185 (3)	0.0633 (13)	0.1015 (18)	−0.0125 (16)	0.0613 (18)	−0.0026 (13)

Geometric parameters (Å, º)

O1—C5	1.423 (3)	C8—C19	1.511 (5)
O1—H1	0.8200	C9—C10	1.493 (5)
O2—C12	1.441 (3)	C9—H9	0.9300
O2—H2	0.8200	C10—C11	1.532 (4)
O3—C13	1.428 (3)	C10—H10A	0.9700
O3—H3	0.8200	C10—H10B	0.9700
O4—C15	1.212 (3)	C11—C12	1.524 (4)
O5—C15	1.325 (3)	C11—H11A	0.9700
O5—C4	1.480 (3)	C11—H11B	0.9700
C1—C16	1.513 (3)	C12—C20	1.518 (4)
C1—C14	1.527 (3)	C12—C13	1.545 (3)
C1—C2	1.533 (3)	C13—C14	1.532 (3)
C1—H1A	0.9800	C13—H13	0.9800
C2—C3	1.521 (4)	C14—H14A	0.9700
C2—H2A	0.9700	C14—H14B	0.9700
C2—H2B	0.9700	C15—C16	1.477 (4)
C3—C4	1.519 (4)	C16—C17	1.324 (4)
C3—H3A	0.9700	C17—H17A	0.9300
C3—H3B	0.9700	C17—H17B	0.9300
C4—C18	1.522 (4)	C18—H18A	0.9600
C4—C5	1.541 (4)	C18—H18B	0.9600
C5—C6	1.525 (4)	C18—H18C	0.9600
C5—H5	0.9800	C19—H19A	0.9600
C6—C7	1.536 (5)	C19—H19B	0.9600
C6—H6A	0.9700	C19—H19C	0.9600
C6—H6B	0.9700	C20—H20A	0.9600
C7—C8	1.494 (6)	C20—H20B	0.9600
C7—H7A	0.9700	C20—H20C	0.9600
C7—H7B	0.9700	O1W—H1B	0.83
C8—C9	1.332 (5)	O1W—H2C	0.8596
C5—O1—H1	109.5	C9—C10—H10B	109.4
C12—O2—H2	109.5	C11—C10—H10B	109.4
C13—O3—H3	109.5	H10A—C10—H10B	108.0
C15—O5—C4	129.7 (2)	C12—C11—C10	117.3 (2)
C16—C1—C14	113.21 (19)	C12—C11—H11A	108.0
C16—C1—C2	109.46 (19)	C10—C11—H11A	108.0
C14—C1—C2	111.78 (16)	C12—C11—H11B	108.0
C16—C1—H1A	107.4	C10—C11—H11B	108.0
C14—C1—H1A	107.4	H11A—C11—H11B	107.2
C2—C1—H1A	107.4	O2—C12—C20	108.6 (2)
C3—C2—C1	114.32 (17)	O2—C12—C11	104.25 (18)
C3—C2—H2A	108.7	C20—C12—C11	112.0 (2)
C1—C2—H2A	108.7	O2—C12—C13	109.06 (19)
C3—C2—H2B	108.7	C20—C12—C13	111.2 (2)
C1—C2—H2B	108.7	C11—C12—C13	111.4 (2)
H2A—C2—H2B	107.6	O3—C13—C14	107.21 (18)
C4—C3—C2	118.6 (2)	O3—C13—C12	111.1 (2)
C4—C3—H3A	107.7	C14—C13—C12	114.29 (18)
C2—C3—H3A	107.7	O3—C13—H13	108.0
C4—C3—H3B	107.7	C14—C13—H13	108.0
C2—C3—H3B	107.7	C12—C13—H13	108.0
H3A—C3—H3B	107.1	C1—C14—C13	114.61 (16)
O5—C4—C3	113.2 (2)	C1—C14—H14A	108.6
O5—C4—C18	103.4 (2)	C13—C14—H14A	108.6
C3—C4—C18	110.7 (2)	C1—C14—H14B	108.6
O5—C4—C5	104.6 (2)	C13—C14—H14B	108.6
C3—C4—C5	112.8 (2)	H14A—C14—H14B	107.6
C18—C4—C5	111.6 (2)	O4—C15—O5	116.3 (3)
O1—C5—C6	109.1 (2)	O4—C15—C16	121.0 (3)
O1—C5—C4	108.2 (2)	O5—C15—C16	122.62 (18)
C6—C5—C4	114.3 (2)	C17—C16—C15	118.1 (2)
O1—C5—H5	108.4	C17—C16—C1	124.8 (2)
C6—C5—H5	108.4	C15—C16—C1	117.1 (2)
C4—C5—H5	108.4	C16—C17—H17A	120.0
C5—C6—C7	112.7 (3)	C16—C17—H17B	120.0
C5—C6—H6A	109.0	H17A—C17—H17B	120.0
C7—C6—H6A	109.0	C4—C18—H18A	109.5
C5—C6—H6B	109.0	C4—C18—H18B	109.5
C7—C6—H6B	109.0	H18A—C18—H18B	109.5
H6A—C6—H6B	107.8	C4—C18—H18C	109.5
C8—C7—C6	112.5 (3)	H18A—C18—H18C	109.5
C8—C7—H7A	109.1	H18B—C18—H18C	109.5
C6—C7—H7A	109.1	C8—C19—H19A	109.5
C8—C7—H7B	109.1	C8—C19—H19B	109.5
C6—C7—H7B	109.1	H19A—C19—H19B	109.5
H7A—C7—H7B	107.8	C8—C19—H19C	109.5
C9—C8—C7	121.6 (3)	H19A—C19—H19C	109.5
C9—C8—C19	121.8 (4)	H19B—C19—H19C	109.5
C7—C8—C19	116.6 (3)	C12—C20—H20A	109.5
C8—C9—C10	128.2 (3)	C12—C20—H20B	109.5
C8—C9—H9	115.9	H20A—C20—H20B	109.5
C10—C9—H9	115.9	C12—C20—H20C	109.5
C9—C10—C11	111.2 (3)	H20A—C20—H20C	109.5
C9—C10—H10A	109.4	H20B—C20—H20C	109.5
C11—C10—H10A	109.4	H1B—O1W—H2C	110
C16—C1—C2—C3	37.0 (3)	C10—C11—C12—O2	−173.7 (2)
C14—C1—C2—C3	163.2 (2)	C10—C11—C12—C20	−56.5 (3)
C1—C2—C3—C4	48.3 (3)	C10—C11—C12—C13	68.8 (3)
C15—O5—C4—C3	2.1 (4)	O2—C12—C13—O3	61.2 (2)
C15—O5—C4—C18	121.9 (3)	C20—C12—C13—O3	−58.5 (3)
C15—O5—C4—C5	−121.2 (3)	C11—C12—C13—O3	175.70 (18)
C2—C3—C4—O5	−68.4 (3)	O2—C12—C13—C14	−60.3 (3)
C2—C3—C4—C18	176.1 (2)	C20—C12—C13—C14	180.0 (2)
C2—C3—C4—C5	50.2 (3)	C11—C12—C13—C14	54.2 (2)
O5—C4—C5—O1	−172.17 (19)	C16—C1—C14—C13	−63.2 (2)
C3—C4—C5—O1	64.3 (3)	C2—C1—C14—C13	172.63 (19)
C18—C4—C5—O1	−61.1 (3)	O3—C13—C14—C1	131.89 (18)
O5—C4—C5—C6	−50.4 (3)	C12—C13—C14—C1	−104.5 (2)
C3—C4—C5—C6	−173.9 (2)	C4—O5—C15—O4	−157.9 (3)
C18—C4—C5—C6	60.7 (3)	C4—O5—C15—C16	26.2 (4)
O1—C5—C6—C7	−100.5 (3)	O4—C15—C16—C17	33.4 (4)
C4—C5—C6—C7	138.2 (3)	O5—C15—C16—C17	−150.8 (3)
C5—C6—C7—C8	−67.5 (4)	O4—C15—C16—C1	−144.7 (3)
C6—C7—C8—C9	106.0 (3)	O5—C15—C16—C1	31.0 (3)
C6—C7—C8—C19	−71.2 (4)	C14—C1—C16—C17	−26.2 (3)
C7—C8—C9—C10	−171.9 (3)	C2—C1—C16—C17	99.2 (3)
C19—C8—C9—C10	5.2 (5)	C14—C1—C16—C15	151.80 (19)
C8—C9—C10—C11	156.2 (3)	C2—C1—C16—C15	−82.8 (2)
C9—C10—C11—C12	−151.5 (2)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···O2^i	0.82	1.86	2.673 (3)	173
O2—H2···O1W^ii	0.82	1.95	2.755 (4)	167
O3—H3···O4^ii	0.82	1.96	2.774 (3)	175
O1W—H1B···O1^ii	0.83	1.99	2.769 (3)	156
O1W—H2C···O3^iii	0.86	1.99	2.834 (3)	168

Symmetry codes: (i) −x+1/2, y−1/2, −z+2; (ii) −x+1/2, y+1/2, −z+1; (iii) −x+1/2, y−1/2, −z+1.