5,6,6a,7,8,8a-Hexahydro-6a,7-dihydroxy-13bH-indeno[2,1-c]phenanthren-9(13cH)-one hemihydrate

In the title compound, C₂₁H₂₀O₃·0.5H₂O, the water mol­ecule lies on a crystallographic twofold rotation axis. The cyclo­hexa­ne ring adopts a twist–boat conformation and the cyclo­hexene ring is in an envelope conformation. In the crystal structure, the mol­ecules are linked via strong O—H...O inter­molecular hydrogen bonds to form chains along the c axis.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.043
• wR factor = 0.102
• Data-to-parameter ratio = 14.9

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT041_ALERT_1_C Calc. and Rep. SumFormula Strings    Differ ....          ?
PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ ....          ?
PLAT045_ALERT_1_C Calculated and Reported Z Differ by ............       0.50 Ratio
PLAT199_ALERT_1_C Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_C Check the Reported _diffrn_ambient_temperature .        293 K

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

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   0 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
   0 ALERT type 4 Improvement, methodology, query or suggestion

---

Computing details

Data collection: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Bruker, 1999); software used to prepare material for publication: SHELXTL.

5,6,6a,7,8,8a-Hexahydro-6a,7-dihydroxy-13bH-indeno[2,1-c]phenanthren- 9(13 cH)-one hemihydrate

Crystal data

C21H20O3·0.5H2O	F(000) = 1400
Mr = 329.38	Dx = 1.320 Mg m^−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 768 reflections
a = 27.942 (9) Å	θ = 2.9–26.0°
b = 14.203 (6) Å	µ = 0.09 mm^−1
c = 8.353 (3) Å	T = 293 K
β = 90.291 (6)°	Prism, colourless
V = 3315 (2) Å^3	0.30 × 0.15 × 0.12 mm
Z = 8

Data collection

Bruker SMART 1000 CCD area-detector diffractometer	2194 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.028
Graphite monochromator	θmax = 26.4°, θmin = 2.6°
φ and ω scans	h = −27→34
8142 measured reflections	k = −15→17
3388 independent reflections	l = −10→7

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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.102	H atoms treated by a mixture of independent and constrained refinement
S = 1.02	w = 1/[σ^2(Fo^2) + (0.0428P)^2 + 0.6586P] where P = (Fo^2 + 2Fc^2)/3
3388 reflections	(Δ/σ)max = 0.001
227 parameters	Δρmax = 0.18 e Å^−3
1 restraint	Δρmin = −0.16 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
O1	0.47109 (4)	0.14976 (9)	0.48606 (13)	0.0458 (3)
H1	0.4919	0.1527	0.4173	0.069*
O2	0.44705 (4)	0.10416 (9)	0.18440 (13)	0.0480 (3)
H2	0.4587	0.0564	0.2234	0.072*
O3	0.28716 (5)	0.10478 (10)	0.14601 (17)	0.0703 (4)
C1	0.42801 (5)	0.19265 (11)	0.42698 (18)	0.0347 (4)
C2	0.40888 (6)	0.13597 (11)	0.28232 (19)	0.0380 (4)
H2A	0.3898	0.1796	0.2172	0.046*
C3	0.37572 (6)	0.05697 (12)	0.3318 (2)	0.0467 (4)
H3A	0.3912	0.0178	0.4119	0.056*
H3B	0.3679	0.0180	0.2399	0.056*
C4	0.33007 (6)	0.10043 (11)	0.4004 (2)	0.0438 (4)
H4	0.3110	0.0513	0.4521	0.053*
C5	0.30102 (6)	0.14546 (13)	0.2663 (2)	0.0471 (4)
C6	0.29403 (5)	0.24531 (12)	0.3036 (2)	0.0416 (4)
C7	0.26950 (6)	0.31268 (14)	0.2148 (2)	0.0532 (5)
H7	0.2543	0.2967	0.1193	0.064*
C8	0.26828 (7)	0.40296 (14)	0.2711 (2)	0.0570 (5)
H8	0.2522	0.4492	0.2131	0.068*
C9	0.29069 (6)	0.42614 (13)	0.4132 (2)	0.0551 (5)
H9	0.2896	0.4880	0.4493	0.066*
C10	0.31475 (6)	0.35951 (12)	0.5029 (2)	0.0488 (5)
H10	0.3292	0.3758	0.5996	0.059*
C11	0.31709 (5)	0.26730 (11)	0.4462 (2)	0.0382 (4)
C12	0.33997 (5)	0.18095 (11)	0.52128 (19)	0.0388 (4)
H12	0.3219	0.1665	0.6185	0.047*
C13	0.39361 (5)	0.18779 (11)	0.57021 (18)	0.0360 (4)
H13	0.4010	0.1286	0.6252	0.043*
C14	0.40140 (5)	0.26499 (11)	0.69368 (18)	0.0382 (4)
C15	0.37685 (6)	0.25963 (14)	0.8385 (2)	0.0511 (5)
H15	0.3594	0.2057	0.8620	0.061*
C16	0.37797 (7)	0.33234 (16)	0.9474 (2)	0.0599 (5)
H16	0.3611	0.3276	1.0428	0.072*
C17	0.40411 (7)	0.41213 (15)	0.9145 (2)	0.0622 (6)
H17	0.4040	0.4626	0.9854	0.075*
C18	0.43040 (6)	0.41657 (13)	0.7758 (2)	0.0533 (5)
H18	0.4489	0.4697	0.7558	0.064*
C19	0.43003 (6)	0.34355 (12)	0.66479 (19)	0.0403 (4)
C20	0.46015 (6)	0.34928 (12)	0.5157 (2)	0.0458 (4)
H20A	0.4918	0.3247	0.5386	0.055*
H20B	0.4635	0.4147	0.4844	0.055*
C21	0.43816 (6)	0.29419 (11)	0.37837 (18)	0.0384 (4)
H21A	0.4598	0.2947	0.2881	0.046*
H21B	0.4085	0.3242	0.3451	0.046*
O4	0.5000	0.05323 (12)	0.7500	0.0532 (5)
H4A	0.5067 (8)	0.0903 (12)	0.8283 (18)	0.080*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
O1	0.0385 (6)	0.0614 (8)	0.0375 (6)	0.0135 (6)	0.0019 (5)	0.0073 (6)
O2	0.0464 (7)	0.0556 (8)	0.0422 (7)	0.0082 (6)	0.0085 (6)	−0.0022 (6)
O3	0.0715 (9)	0.0675 (9)	0.0718 (10)	−0.0069 (8)	−0.0165 (8)	−0.0208 (8)
C1	0.0299 (8)	0.0400 (9)	0.0341 (8)	0.0044 (7)	0.0018 (7)	0.0049 (7)
C2	0.0365 (9)	0.0392 (9)	0.0383 (9)	0.0053 (7)	0.0037 (7)	0.0006 (8)
C3	0.0514 (10)	0.0372 (10)	0.0517 (11)	−0.0003 (8)	0.0048 (8)	−0.0023 (8)
C4	0.0414 (10)	0.0372 (9)	0.0527 (11)	−0.0096 (8)	0.0070 (8)	−0.0009 (8)
C5	0.0361 (9)	0.0510 (11)	0.0543 (11)	−0.0113 (8)	0.0026 (8)	−0.0067 (9)
C6	0.0281 (8)	0.0498 (10)	0.0470 (10)	−0.0023 (8)	0.0043 (7)	−0.0030 (8)
C7	0.0394 (10)	0.0712 (14)	0.0489 (11)	0.0091 (9)	0.0000 (8)	−0.0036 (10)
C8	0.0474 (11)	0.0634 (13)	0.0604 (13)	0.0179 (10)	0.0056 (9)	0.0093 (11)
C9	0.0453 (10)	0.0462 (11)	0.0737 (14)	0.0094 (9)	0.0060 (10)	−0.0035 (10)
C10	0.0383 (9)	0.0498 (11)	0.0583 (11)	0.0042 (8)	−0.0008 (8)	−0.0091 (9)
C11	0.0267 (8)	0.0430 (10)	0.0448 (10)	−0.0018 (7)	0.0066 (7)	−0.0007 (8)
C12	0.0353 (9)	0.0406 (9)	0.0408 (9)	−0.0039 (7)	0.0090 (7)	0.0021 (8)
C13	0.0362 (9)	0.0372 (9)	0.0345 (8)	0.0025 (7)	0.0040 (7)	0.0083 (7)
C14	0.0350 (9)	0.0458 (10)	0.0338 (8)	0.0061 (8)	−0.0017 (7)	0.0046 (8)
C15	0.0517 (11)	0.0628 (12)	0.0389 (10)	0.0021 (9)	0.0048 (8)	0.0033 (9)
C16	0.0605 (12)	0.0845 (15)	0.0348 (10)	0.0081 (12)	0.0064 (9)	−0.0046 (10)
C17	0.0638 (13)	0.0742 (15)	0.0486 (12)	0.0064 (11)	−0.0047 (10)	−0.0188 (10)
C18	0.0523 (11)	0.0565 (12)	0.0509 (11)	−0.0026 (9)	−0.0082 (9)	−0.0065 (9)
C19	0.0359 (9)	0.0481 (10)	0.0370 (9)	0.0019 (8)	−0.0055 (7)	0.0009 (8)
C20	0.0424 (10)	0.0455 (10)	0.0496 (10)	−0.0069 (8)	0.0033 (8)	0.0003 (8)
C21	0.0354 (8)	0.0438 (10)	0.0361 (9)	−0.0017 (7)	0.0053 (7)	0.0052 (8)
O4	0.0745 (12)	0.0425 (11)	0.0426 (11)	0.000	−0.0106 (9)	0.000

Geometric parameters (Å, º)

O1—C1	1.4345 (17)	C10—C11	1.394 (2)
O1—H1	0.82	C10—H10	0.93
O2—C2	1.4209 (19)	C11—C12	1.517 (2)
O2—H2	0.82	C12—C13	1.554 (2)
O3—C5	1.220 (2)	C12—H12	0.98
C1—C21	1.525 (2)	C13—C14	1.520 (2)
C1—C13	1.540 (2)	C13—H13	0.98
C1—C2	1.545 (2)	C14—C19	1.395 (2)
C2—C3	1.514 (2)	C14—C15	1.396 (2)
C2—H2A	0.98	C15—C16	1.376 (3)
C3—C4	1.531 (2)	C15—H15	0.93
C3—H3A	0.97	C16—C17	1.377 (3)
C3—H3B	0.97	C16—H16	0.93
C4—C5	1.521 (2)	C17—C18	1.376 (3)
C4—C12	1.550 (2)	C17—H17	0.93
C4—H4	0.98	C18—C19	1.391 (2)
C5—C6	1.465 (2)	C18—H18	0.93
C6—C11	1.387 (2)	C19—C20	1.509 (2)
C6—C7	1.389 (2)	C20—C21	1.516 (2)
C7—C8	1.366 (3)	C20—H20A	0.97
C7—H7	0.93	C20—H20B	0.97
C8—C9	1.379 (3)	C21—H21A	0.97
C8—H8	0.93	C21—H21B	0.97
C9—C10	1.380 (2)	O4—H4A	0.86 (1)
C9—H9	0.93
C1—O1—H1	109.5	C6—C11—C12	111.48 (14)
C2—O2—H2	109.5	C10—C11—C12	129.73 (15)
O1—C1—C21	109.66 (12)	C11—C12—C4	104.69 (13)
O1—C1—C13	103.87 (12)	C11—C12—C13	117.51 (13)
C21—C1—C13	111.52 (13)	C4—C12—C13	112.72 (13)
O1—C1—C2	109.52 (13)	C11—C12—H12	107.1
C21—C1—C2	110.39 (13)	C4—C12—H12	107.1
C13—C1—C2	111.67 (12)	C13—C12—H12	107.1
O2—C2—C3	112.56 (13)	C14—C13—C1	114.00 (13)
O2—C2—C1	110.99 (13)	C14—C13—C12	110.98 (12)
C3—C2—C1	112.49 (14)	C1—C13—C12	113.79 (13)
O2—C2—H2A	106.8	C14—C13—H13	105.7
C3—C2—H2A	106.8	C1—C13—H13	105.7
C1—C2—H2A	106.8	C12—C13—H13	105.7
C2—C3—C4	108.41 (13)	C19—C14—C15	118.58 (16)
C2—C3—H3A	110.0	C19—C14—C13	122.68 (14)
C4—C3—H3A	110.0	C15—C14—C13	118.65 (15)
C2—C3—H3B	110.0	C16—C15—C14	121.48 (18)
C4—C3—H3B	110.0	C16—C15—H15	119.3
H3A—C3—H3B	108.4	C14—C15—H15	119.3
C5—C4—C3	109.64 (15)	C15—C16—C17	119.74 (18)
C5—C4—C12	105.22 (14)	C15—C16—H16	120.1
C3—C4—C12	113.27 (13)	C17—C16—H16	120.1
C5—C4—H4	109.5	C18—C17—C16	119.46 (18)
C3—C4—H4	109.5	C18—C17—H17	120.3
C12—C4—H4	109.5	C16—C17—H17	120.3
O3—C5—C6	126.23 (18)	C17—C18—C19	121.65 (18)
O3—C5—C4	124.98 (17)	C17—C18—H18	119.2
C6—C5—C4	108.77 (15)	C19—C18—H18	119.2
C11—C6—C7	121.95 (17)	C18—C19—C14	118.91 (16)
C11—C6—C5	109.78 (15)	C18—C19—C20	120.51 (16)
C7—C6—C5	128.26 (17)	C14—C19—C20	120.58 (15)
C8—C7—C6	118.43 (18)	C19—C20—C21	111.78 (13)
C8—C7—H7	120.8	C19—C20—H20A	109.3
C6—C7—H7	120.8	C21—C20—H20A	109.3
C7—C8—C9	120.53 (18)	C19—C20—H20B	109.3
C7—C8—H8	119.7	C21—C20—H20B	109.3
C9—C8—H8	119.7	H20A—C20—H20B	107.9
C8—C9—C10	121.44 (18)	C20—C21—C1	111.21 (13)
C8—C9—H9	119.3	C20—C21—H21A	109.4
C10—C9—H9	119.3	C1—C21—H21A	109.4
C9—C10—C11	118.90 (17)	C20—C21—H21B	109.4
C9—C10—H10	120.5	C1—C21—H21B	109.4
C11—C10—H10	120.5	H21A—C21—H21B	108.0
C6—C11—C10	118.73 (16)
O1—C1—C2—O2	−38.62 (17)	C3—C4—C12—C11	118.27 (15)
C21—C1—C2—O2	82.22 (16)	C5—C4—C12—C13	−130.34 (14)
C13—C1—C2—O2	−153.11 (13)	C3—C4—C12—C13	−10.59 (19)
O1—C1—C2—C3	88.51 (15)	O1—C1—C13—C14	80.81 (15)
C21—C1—C2—C3	−150.65 (13)	C21—C1—C13—C14	−37.22 (17)
C13—C1—C2—C3	−25.98 (18)	C2—C1—C13—C14	−161.25 (12)
O2—C2—C3—C4	−166.40 (13)	O1—C1—C13—C12	−150.54 (13)
C1—C2—C3—C4	67.32 (17)	C21—C1—C13—C12	91.43 (16)
C2—C3—C4—C5	70.81 (17)	C2—C1—C13—C12	−32.60 (18)
C2—C3—C4—C12	−46.37 (19)	C11—C12—C13—C14	60.39 (18)
C3—C4—C5—O3	56.1 (2)	C4—C12—C13—C14	−177.74 (13)
C12—C4—C5—O3	178.24 (16)	C11—C12—C13—C1	−69.79 (18)
C3—C4—C5—C6	−122.09 (15)	C4—C12—C13—C1	52.09 (18)
C12—C4—C5—C6	0.03 (17)	C1—C13—C14—C19	12.4 (2)
O3—C5—C6—C11	−176.57 (17)	C12—C13—C14—C19	−117.62 (16)
C4—C5—C6—C11	1.60 (18)	C1—C13—C14—C15	−171.13 (14)
O3—C5—C6—C7	2.2 (3)	C12—C13—C14—C15	58.81 (18)
C4—C5—C6—C7	−179.66 (16)	C19—C14—C15—C16	4.2 (2)
C11—C6—C7—C8	−0.1 (3)	C13—C14—C15—C16	−172.38 (15)
C5—C6—C7—C8	−178.69 (17)	C14—C15—C16—C17	−0.6 (3)
C6—C7—C8—C9	−0.4 (3)	C15—C16—C17—C18	−2.6 (3)
C7—C8—C9—C10	−0.2 (3)	C16—C17—C18—C19	2.2 (3)
C8—C9—C10—C11	1.3 (3)	C17—C18—C19—C14	1.5 (3)
C7—C6—C11—C10	1.1 (2)	C17—C18—C19—C20	−178.49 (17)
C5—C6—C11—C10	179.97 (14)	C15—C14—C19—C18	−4.6 (2)
C7—C6—C11—C12	178.51 (14)	C13—C14—C19—C18	171.87 (14)
C5—C6—C11—C12	−2.65 (18)	C15—C14—C19—C20	175.40 (15)
C9—C10—C11—C6	−1.7 (2)	C13—C14—C19—C20	−8.2 (2)
C9—C10—C11—C12	−178.54 (16)	C18—C19—C20—C21	−151.38 (15)
C6—C11—C12—C4	2.58 (16)	C14—C19—C20—C21	28.7 (2)
C10—C11—C12—C4	179.58 (16)	C19—C20—C21—C1	−53.89 (18)
C6—C11—C12—C13	128.51 (14)	O1—C1—C21—C20	−55.36 (17)
C10—C11—C12—C13	−54.5 (2)	C13—C1—C21—C20	59.13 (17)
C5—C4—C12—C11	−1.47 (16)	C2—C1—C21—C20	−176.12 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O4—H4A···O1^i	0.86 (1)	1.87 (1)	2.716 (2)	168 (2)
O2—H2···O4^ii	0.82	1.95	2.735 (2)	160
O1—H1···O2^iii	0.82	2.03	2.777 (2)	151

Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1, −y, −z+1; (iii) −x+1, y, −z+1/2.