Racemic (1SR,2SR,7aRS)-1,2,7a-trihydr­oxy-2-methyl­perhydro-1-phosphaindene 1-oxide monohydrate

In the title racemic compound, C₉H₁₉O₅P, all inter­atomic C—C and C—OH distances can be considered normal. The P—O and P=O distances are 1.5583 (8) and 1.5003 (7) Å, respectively. The rings are cis-fused, the phospho­lane ring exists in a slightly distorted envelope conformation and the cyclo­hexane ring adopts an almost ideal chair conformation. All hydroxyl groups are anti to the P=O bond. Mol­ecules are linked via medium-strength inter­molecular O—H...O hydrogen bonds into a three-dimensional network.

Key indicators

• Single-crystal X-ray study
• T = 291 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.028
• wR factor = 0.079
• Data-to-parameter ratio = 20.7

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT201_ALERT_2_B Isotropic non-H Atoms in Main Residue(s) .......          1
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1O    ..  H99O    ..       2.01 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H1O    ..  H99P    ..       2.09 Ang.

Alert level C
PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given .......          ?
PLAT222_ALERT_3_C Large Non-Solvent    H     Ueq(max)/Ueq(min) ...       3.17 Ratio

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

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

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Computing details

Data collection: CrysAlis CCD (UNIL IC & Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Version 1.4; Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

(1S,2S,7aR)-1,2,7a-trihydroxy-2-methylperhydro-1-phosphaindene 1-oxide hydrate

Crystal data

C9H17O4P·H2O	Z = 2
Mr = 238.21	F(000) = 256
Triclinic, P1	Dx = 1.441 Mg m^−3
a = 6.4427 (3) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.1772 (5) Å	Cell parameters from 5990 reflections
c = 11.3794 (6) Å	θ = 2–25°
α = 69.954 (5)°	µ = 0.25 mm^−1
β = 77.247 (4)°	T = 291 K
γ = 83.521 (4)°	Prism, colourless
V = 548.84 (5) Å^3	0.38 × 0.30 × 0.26 mm

Data collection

Kuma KM-4-CCD diffractometer	3130 independent reflections
Radiation source: fine-focus sealed tube	2936 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.018
ω scans	θmax = 30.7°, θmin = 3.2°
Absorption correction: numerical (X-RED; Stoe & Cie, 1999)	h = −9→8
Tmin = 0.912, Tmax = 0.938	k = −11→11
10280 measured reflections	l = −16→15

Refinement

Refinement on F^2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: structure-invariant direct methods
R[F^2 > 2σ(F^2)] = 0.028	Hydrogen site location: structure-invariant direct methods
wR(F^2) = 0.079	H atoms treated by a mixture of independent and constrained refinement
S = 1.11	w = 1/[σ^2(Fo^2) + (0.0413P)^2 + 0.1433P] where P = (Fo^2 + 2Fc^2)/3
3130 reflections	(Δ/σ)max = 0.001
151 parameters	Δρmax = 0.27 e Å^−3
3 restraints	Δρmin = −0.44 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
P1	0.73188 (3)	0.68020 (3)	0.63173 (2)	0.01651 (7)
O1	0.80825 (12)	0.69437 (10)	0.48889 (7)	0.02546 (16)
H1O	0.7288	0.7657	0.4307	0.076 (7)*
O2	0.52769 (11)	0.77964 (9)	0.66064 (8)	0.02400 (16)
O3	1.14181 (11)	0.72916 (12)	0.59406 (8)	0.02883 (17)
H3O	1.2572	0.7428	0.6197	0.050 (5)*
O4	0.72505 (12)	0.33449 (10)	0.65168 (7)	0.02497 (16)
H4O	0.8417	0.3475	0.5893	0.056 (5)*
C1	0.95503 (14)	0.73461 (12)	0.68860 (9)	0.01906 (18)
C2	0.95989 (15)	0.57838 (13)	0.81168 (10)	0.02117 (18)
H2A	1.0934	0.5721	0.8394	0.025*
H2B	0.8442	0.5912	0.8792	0.025*
C3	0.93611 (15)	0.41196 (12)	0.78212 (10)	0.01988 (18)
H3	1.0559	0.4043	0.7139	0.024*
C4	0.73010 (14)	0.44307 (12)	0.72650 (9)	0.01690 (17)
C5	0.93950 (18)	0.24110 (14)	0.89378 (11)	0.0284 (2)
H5A	0.9633	0.1445	0.8607	0.034*
H5B	1.0582	0.2401	0.9337	0.034*
C6	0.7350 (2)	0.21352 (15)	0.99489 (11)	0.0312 (2)
H6A	0.7424	0.0994	1.0587	0.037*
H6B	0.7195	0.3005	1.0370	0.037*
C7	0.54296 (18)	0.22759 (15)	0.93349 (11)	0.0284 (2)
H7A	0.4139	0.2111	0.9984	0.034*
H7B	0.5550	0.1366	0.8954	0.034*
C8	0.52887 (15)	0.40562 (13)	0.83110 (10)	0.02259 (19)
H8A	0.5060	0.4955	0.8709	0.027*
H8B	0.4072	0.4104	0.7926	0.027*
C9	0.92442 (19)	0.90978 (14)	0.71070 (12)	0.0289 (2)
H9A	1.0431	0.9276	0.7425	0.043*
H9B	0.7955	0.9112	0.7718	0.043*
H9C	0.9153	1.0010	0.6317	0.043*
O99	0.58743 (13)	0.88192 (11)	0.33297 (8)	0.02909 (17)
H99O	0.483 (3)	0.822 (2)	0.3398 (18)	0.053 (5)*
H99P	0.538 (3)	0.978 (2)	0.3442 (18)	0.051 (5)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01366 (11)	0.01659 (12)	0.02060 (12)	0.00026 (8)	−0.00438 (8)	−0.00737 (9)
O1	0.0260 (4)	0.0300 (4)	0.0206 (3)	0.0030 (3)	−0.0062 (3)	−0.0087 (3)
O2	0.0161 (3)	0.0219 (3)	0.0356 (4)	0.0034 (3)	−0.0063 (3)	−0.0119 (3)
O3	0.0146 (3)	0.0438 (5)	0.0307 (4)	−0.0057 (3)	−0.0004 (3)	−0.0166 (3)
O4	0.0286 (4)	0.0239 (4)	0.0278 (4)	−0.0063 (3)	−0.0029 (3)	−0.0153 (3)
C1	0.0150 (4)	0.0206 (4)	0.0239 (4)	−0.0022 (3)	−0.0034 (3)	−0.0100 (3)
C2	0.0198 (4)	0.0219 (4)	0.0260 (4)	0.0006 (3)	−0.0092 (3)	−0.0106 (4)
C3	0.0162 (4)	0.0195 (4)	0.0263 (4)	0.0027 (3)	−0.0065 (3)	−0.0100 (4)
C4	0.0156 (4)	0.0166 (4)	0.0207 (4)	−0.0004 (3)	−0.0039 (3)	−0.0088 (3)
C5	0.0277 (5)	0.0212 (5)	0.0364 (6)	0.0051 (4)	−0.0137 (4)	−0.0068 (4)
C6	0.0398 (6)	0.0260 (5)	0.0256 (5)	−0.0001 (4)	−0.0102 (4)	−0.0038 (4)
C7	0.0274 (5)	0.0258 (5)	0.0262 (5)	−0.0047 (4)	−0.0007 (4)	−0.0029 (4)
C8	0.0172 (4)	0.0229 (5)	0.0253 (5)	0.0001 (3)	−0.0011 (3)	−0.0070 (4)
C9	0.0312 (5)	0.0209 (5)	0.0397 (6)	−0.0043 (4)	−0.0092 (4)	−0.0138 (4)

Geometric parameters (Å, º)

P1—O2	1.5003 (7)	C4—C8	1.5329 (13)
P1—O1	1.5583 (8)	C5—C6	1.5267 (17)
P1—C1	1.8537 (9)	C5—H5A	0.9700
P1—C4	1.8679 (10)	C5—H5B	0.9700
O1—H1O	0.9264	C6—C7	1.5251 (16)
O3—C1	1.4341 (12)	C6—H6A	0.9700
O3—H3O	0.8875	C6—H6B	0.9700
O4—C4	1.4323 (11)	C7—C8	1.5294 (15)
O4—H4O	0.9007	C7—H7A	0.9700
C1—C9	1.5216 (14)	C7—H7B	0.9700
C1—C2	1.5422 (14)	C8—H8A	0.9700
C2—C3	1.5402 (13)	C8—H8B	0.9700
C2—H2A	0.9700	C9—H9A	0.9600
C2—H2B	0.9700	C9—H9B	0.9600
C3—C5	1.5347 (14)	C9—H9C	0.9600
C3—C4	1.5528 (13)	O99—H99O	0.850 (14)
C3—H3	0.9800	O99—H99P	0.856 (14)
O2—P1—O1	115.11 (4)	C3—C4—P1	103.36 (6)
O2—P1—C1	113.38 (4)	C6—C5—C3	113.71 (9)
O1—P1—C1	108.51 (4)	C6—C5—H5A	108.8
O2—P1—C4	114.28 (4)	C3—C5—H5A	108.8
O1—P1—C4	106.91 (4)	C6—C5—H5B	108.8
C1—P1—C4	96.99 (4)	C3—C5—H5B	108.8
P1—O1—H1O	118.0	H5A—C5—H5B	107.7
C1—O3—H3O	110.3	C7—C6—C5	110.18 (9)
C4—O4—H4O	110.8	C7—C6—H6A	109.6
O3—C1—C9	111.35 (8)	C5—C6—H6A	109.6
O3—C1—C2	110.42 (8)	C7—C6—H6B	109.6
C9—C1—C2	113.40 (8)	C5—C6—H6B	109.6
O3—C1—P1	105.80 (6)	H6A—C6—H6B	108.1
C9—C1—P1	113.99 (7)	C6—C7—C8	110.77 (9)
C2—C1—P1	101.23 (6)	C6—C7—H7A	109.5
C3—C2—C1	107.75 (8)	C8—C7—H7A	109.5
C3—C2—H2A	110.2	C6—C7—H7B	109.5
C1—C2—H2A	110.2	C8—C7—H7B	109.5
C3—C2—H2B	110.2	H7A—C7—H7B	108.1
C1—C2—H2B	110.2	C7—C8—C4	112.55 (8)
H2A—C2—H2B	108.5	C7—C8—H8A	109.1
C5—C3—C2	115.43 (8)	C4—C8—H8A	109.1
C5—C3—C4	113.24 (8)	C7—C8—H8B	109.1
C2—C3—C4	105.90 (7)	C4—C8—H8B	109.1
C5—C3—H3	107.3	H8A—C8—H8B	107.8
C2—C3—H3	107.3	C1—C9—H9A	109.5
C4—C3—H3	107.3	C1—C9—H9B	109.5
O4—C4—C8	106.02 (7)	H9A—C9—H9B	109.5
O4—C4—C3	112.77 (7)	C1—C9—H9C	109.5
C8—C4—C3	112.24 (8)	H9A—C9—H9C	109.5
O4—C4—P1	112.97 (6)	H9B—C9—H9C	109.5
C8—C4—P1	109.60 (6)	H99O—O99—H99P	108.4 (16)
P1—C1—C2—C3	43.86 (8)	C5—C6—C7—C8	−58.56 (12)
C1—C2—C3—C4	−54.42 (9)	C6—C7—C8—C4	57.80 (12)
C2—C3—C4—P1	35.92 (8)	C7—C8—C4—C3	−50.59 (11)
C3—C4—P1—C1	−9.52 (6)	C8—C4—C3—C5	45.38 (11)
C4—P1—C1—C2	−19.04 (6)	C2—C3—C4—C8	−82.09 (9)
C4—C3—C5—C6	−48.11 (12)	C5—C3—C4—P1	163.38 (7)
C3—C5—C6—C7	54.41 (13)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1O···O99	0.93	1.58	2.5062 (11)	178
O3—H3O···O2^i	0.89	1.98	2.8640 (10)	175
O4—H4O···O1^ii	0.90	2.27	3.1033 (11)	154
O4—H4O···O3^ii	0.90	2.35	2.9435 (11)	123
O99—H99O···O4^iii	0.85 (1)	1.92 (1)	2.7662 (11)	173 (2)
O99—H99P···O2^iv	0.86 (1)	1.96 (1)	2.8045 (11)	168 (2)

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