2-Hydr­oxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphospho­rinan-2-one monohydrate

The title compound, C₁₁H₁₅O₄P·H₂O, commonly called (S)-phencyphos monohydrate, belongs to a class of phosphori­nanes. Mol­ecules form a hydrogen-bond network of corrugated ribbons.

Key indicators

• Single-crystal X-ray study
• T = 173 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.034
• wR factor = 0.085
• Data-to-parameter ratio = 18.0

checkCIF/PLATON results

No syntax errors found



Alert level B
PLAT417_ALERT_2_B Short Inter D-H..H-D       H99A   ..  H99C    ..       1.92 Ang.
PLAT417_ALERT_2_B Short Inter D-H..H-D       H99B   ..  H99C    ..       1.96 Ang.

Alert level C
PLAT063_ALERT_3_C Crystal Probably too Large for Beam Size .......       0.61 mm
PLAT480_ALERT_4_C Long H...A H-Bond Reported H9     ..  O4      ..       2.68 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           28.20
           From the CIF: _reflns_number_total               3004
           Count of symmetry unique reflns         1818
           Completeness (_total/calc)            165.24%
           TEST3: Check Friedels for noncentro structure
           Estimate of Friedel pairs measured      1186
           Fraction of Friedel pairs measured     0.652
           Are heavy atom types Z>Si present        yes
PLAT791_ALERT_1_G Confirm the Absolute Configuration of P1     = .          R
PLAT791_ALERT_1_G Confirm the Absolute Configuration of C2     = .          S

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

   2 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
   2 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

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Computing details

Data collection: SMART (Bruker, 2003); cell refinement: SAINT (Bruker, 2003); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: Mercury (Bruno et al., 2002); software used to prepare material for publication: SHELXL97.

2-Hydroxy-5,5-dimethyl-4-phenyl-1,3,2-dioxaphosphorinan-2-one monohydrate

Crystal data

C11H15O4P·H2O	Dx = 1.372 Mg m^−3
Mr = 260.22	Melting point: 86.5 K
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 983 reflections
a = 6.017 (2) Å	θ = 2.6–27.3°
b = 8.219 (3) Å	µ = 0.23 mm^−1
c = 25.475 (10) Å	T = 173 K
V = 1259.7 (8) Å^3	Columnar, colourless
Z = 4	0.61 × 0.09 × 0.04 mm
F(000) = 552

Data collection

Bruker SMART CCD area-detector diffractometer	3004 independent reflections
Radiation source: fine-focus sealed tube	2899 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 28.2°, θmin = 1.6°
Absorption correction: multi-scan (SADABS; Sheldrick, 2003)	h = −7→7
Tmin = 0.861, Tmax = 0.991	k = −10→10
23045 measured reflections	l = −32→33

Refinement

Refinement on F^2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F^2 > 2σ(F^2)] = 0.034	H atoms treated by a mixture of independent and constrained refinement
wR(F^2) = 0.085	w = 1/[σ^2(Fo^2) + (0.0515P)^2 + 0.1668P] where P = (Fo^2 + 2Fc^2)/3
S = 1.11	(Δ/σ)max < 0.001
3004 reflections	Δρmax = 0.45 e Å^−3
167 parameters	Δρmin = −0.23 e Å^−3
1 restraint	Absolute structure: Flack (1983), 1213 friedel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: −0.03 (8)

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	0.04332 (6)	0.02404 (5)	0.062277 (15)	0.02174 (11)
O4	0.13990 (18)	0.06124 (12)	0.11859 (4)	0.0216 (2)
O5	0.1019 (2)	0.17828 (14)	0.02882 (4)	0.0273 (3)
O1	0.5676 (2)	0.77298 (15)	0.05308 (5)	0.0285 (2)
O2	0.1509 (2)	−0.12296 (15)	0.03994 (5)	0.0303 (3)
O3	−0.20975 (18)	0.01727 (15)	0.06703 (5)	0.0334 (3)
H99C	−0.277 (4)	−0.0890 (17)	0.0584 (9)	0.050*
C1	0.0706 (3)	0.52093 (19)	0.12726 (6)	0.0287 (3)
H1A	0.1057	0.6075	0.1022	0.043*
H1B	0.1422	0.5445	0.1610	0.043*
H1C	−0.0908	0.5150	0.1322	0.043*
C2	0.0789 (2)	0.21820 (17)	0.14251 (5)	0.0191 (3)
H2	−0.0867	0.2230	0.1454	0.023*
C3	0.0473 (3)	0.33505 (18)	0.05212 (5)	0.0259 (3)
H3A	−0.1161	0.3439	0.0558	0.031*
H3B	0.0974	0.4230	0.0284	0.031*
C4	0.1558 (3)	0.35813 (18)	0.10614 (6)	0.0207 (3)
C5	0.0658 (3)	0.30463 (19)	0.23693 (6)	0.0283 (3)
H5	−0.0710	0.3579	0.2297	0.034*
C6	0.4105 (3)	0.3620 (2)	0.10073 (6)	0.0265 (3)
H6A	0.4532	0.4477	0.0760	0.040*
H6B	0.4631	0.2566	0.0877	0.040*
H6C	0.4775	0.3842	0.1351	0.040*
C7	0.1749 (3)	0.21961 (19)	0.19719 (6)	0.0220 (3)
C8	0.3730 (3)	0.1395 (2)	0.20878 (6)	0.0297 (4)
H8	0.4478	0.0799	0.1822	0.036*
C9	0.1567 (4)	0.3118 (2)	0.28727 (6)	0.0352 (4)
H9	0.0820	0.3706	0.3141	0.042*
C10	0.4618 (3)	0.1465 (2)	0.25917 (6)	0.0367 (4)
H10	0.5965	0.0911	0.2668	0.044*
C11	0.3549 (4)	0.2338 (2)	0.29832 (6)	0.0378 (4)
H11	0.4174	0.2400	0.3325	0.045*
H99A	0.588 (4)	0.725 (3)	0.0258 (9)	0.050 (7)*
H99B	0.435 (5)	0.802 (3)	0.0525 (9)	0.056 (7)*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P1	0.01937 (18)	0.02179 (18)	0.02406 (18)	−0.00055 (14)	−0.00106 (14)	−0.00604 (14)
O4	0.0261 (5)	0.0180 (5)	0.0208 (5)	0.0002 (4)	−0.0004 (4)	−0.0023 (4)
O5	0.0345 (6)	0.0287 (6)	0.0185 (5)	−0.0015 (5)	−0.0003 (5)	−0.0027 (4)
O1	0.0240 (6)	0.0282 (6)	0.0333 (6)	−0.0021 (5)	0.0020 (5)	−0.0075 (5)
O2	0.0264 (6)	0.0295 (6)	0.0350 (6)	0.0019 (5)	−0.0021 (5)	−0.0132 (5)
O3	0.0201 (5)	0.0275 (6)	0.0527 (7)	−0.0007 (5)	−0.0012 (5)	−0.0121 (6)
C1	0.0363 (8)	0.0201 (7)	0.0297 (7)	0.0035 (7)	−0.0010 (6)	−0.0005 (6)
C2	0.0186 (7)	0.0178 (6)	0.0210 (6)	0.0009 (5)	0.0016 (5)	−0.0016 (5)
C3	0.0331 (8)	0.0227 (7)	0.0218 (7)	−0.0002 (7)	−0.0029 (7)	0.0024 (5)
C4	0.0234 (7)	0.0192 (7)	0.0194 (6)	−0.0008 (6)	0.0007 (6)	0.0000 (5)
C5	0.0330 (8)	0.0269 (7)	0.0250 (7)	−0.0007 (7)	0.0066 (7)	0.0002 (6)
C6	0.0251 (8)	0.0252 (7)	0.0293 (7)	−0.0057 (6)	0.0021 (6)	0.0015 (6)
C7	0.0270 (7)	0.0204 (7)	0.0187 (6)	−0.0032 (6)	0.0014 (6)	0.0002 (5)
C8	0.0337 (9)	0.0306 (8)	0.0249 (7)	0.0039 (7)	−0.0017 (7)	−0.0007 (6)
C9	0.0538 (12)	0.0312 (9)	0.0205 (7)	−0.0058 (8)	0.0083 (7)	−0.0024 (6)
C10	0.0401 (10)	0.0389 (9)	0.0311 (8)	0.0027 (9)	−0.0108 (8)	0.0045 (7)
C11	0.0565 (12)	0.0356 (9)	0.0212 (7)	−0.0101 (9)	−0.0062 (8)	0.0026 (7)

Geometric parameters (Å, º)

P1—O2	1.4841 (13)	C3—H3A	0.9900
P1—O3	1.5284 (13)	C3—H3B	0.9900
P1—O5	1.5678 (12)	C4—C6	1.539 (2)
P1—O4	1.5778 (12)	C5—C7	1.394 (2)
O4—C2	1.4731 (17)	C5—C9	1.395 (2)
O5—C3	1.4564 (18)	C5—H5	0.9500
O1—H99A	0.81 (3)	C6—H6A	0.9800
O1—H99B	0.83 (3)	C6—H6B	0.9800
O3—H99C	0.988 (10)	C6—H6C	0.9800
C1—C4	1.531 (2)	C7—C8	1.393 (2)
C1—H1A	0.9800	C8—C10	1.392 (2)
C1—H1B	0.9800	C8—H8	0.9500
C1—H1C	0.9800	C9—C11	1.383 (3)
C2—C7	1.5080 (19)	C9—H9	0.9500
C2—C4	1.548 (2)	C10—C11	1.387 (3)
C2—H2	1.0000	C10—H10	0.9500
C3—C4	1.535 (2)	C11—H11	0.9500
O2—P1—O3	115.80 (7)	C1—C4—C6	110.31 (12)
O2—P1—O5	110.59 (7)	C3—C4—C6	110.24 (12)
O3—P1—O5	107.25 (7)	C1—C4—C2	109.81 (12)
O2—P1—O4	110.23 (7)	C3—C4—C2	108.52 (12)
O3—P1—O4	107.58 (7)	C6—C4—C2	111.52 (12)
O5—P1—O4	104.76 (6)	C7—C5—C9	120.26 (17)
C2—O4—P1	117.00 (9)	C7—C5—H5	119.9
C3—O5—P1	116.29 (9)	C9—C5—H5	119.9
H99A—O1—H99B	106 (2)	C4—C6—H6A	109.5
P1—O3—H99C	115.1 (14)	C4—C6—H6B	109.5
C4—C1—H1A	109.5	H6A—C6—H6B	109.5
C4—C1—H1B	109.5	C4—C6—H6C	109.5
H1A—C1—H1B	109.5	H6A—C6—H6C	109.5
C4—C1—H1C	109.5	H6B—C6—H6C	109.5
H1A—C1—H1C	109.5	C8—C7—C5	119.06 (15)
H1B—C1—H1C	109.5	C8—C7—C2	121.32 (13)
O4—C2—C7	107.06 (11)	C5—C7—C2	119.61 (14)
O4—C2—C4	109.18 (11)	C10—C8—C7	120.29 (16)
C7—C2—C4	115.63 (12)	C10—C8—H8	119.9
O4—C2—H2	108.3	C7—C8—H8	119.9
C7—C2—H2	108.3	C11—C9—C5	120.37 (16)
C4—C2—H2	108.3	C11—C9—H9	119.8
O5—C3—C4	112.25 (12)	C5—C9—H9	119.8
O5—C3—H3A	109.2	C11—C10—C8	120.46 (18)
C4—C3—H3A	109.2	C11—C10—H10	119.8
O5—C3—H3B	109.2	C8—C10—H10	119.8
C4—C3—H3B	109.2	C9—C11—C10	119.55 (16)
H3A—C3—H3B	107.9	C9—C11—H11	120.2
C1—C4—C3	106.29 (12)	C10—C11—H11	120.2
O2—P1—O4—C2	169.94 (10)	C7—C2—C4—C3	178.55 (12)
O3—P1—O4—C2	−62.95 (11)	O4—C2—C4—C6	−63.82 (14)
O5—P1—O4—C2	50.95 (11)	C7—C2—C4—C6	56.93 (16)
O2—P1—O5—C3	−167.49 (10)	C9—C5—C7—C8	1.3 (2)
O3—P1—O5—C3	65.40 (12)	C9—C5—C7—C2	−177.73 (15)
O4—P1—O5—C3	−48.74 (12)	O4—C2—C7—C8	32.12 (19)
P1—O4—C2—C7	175.61 (10)	C4—C2—C7—C8	−89.78 (18)
P1—O4—C2—C4	−58.53 (14)	O4—C2—C7—C5	−148.88 (13)
P1—O5—C3—C4	56.37 (16)	C4—C2—C7—C5	89.22 (17)
O5—C3—C4—C1	−175.98 (13)	C5—C7—C8—C10	−0.9 (3)
O5—C3—C4—C6	64.48 (16)	C2—C7—C8—C10	178.12 (15)
O5—C3—C4—C2	−57.92 (16)	C7—C5—C9—C11	−0.5 (3)
O4—C2—C4—C1	173.59 (12)	C7—C8—C10—C11	−0.4 (3)
C7—C2—C4—C1	−65.65 (17)	C5—C9—C11—C10	−0.8 (3)
O4—C2—C4—C3	57.79 (15)	C8—C10—C11—C9	1.2 (3)

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O1—H99B···O2^i	0.83 (3)	1.85 (3)	2.670 (2)	171 (2)
O1—H99A···O2^ii	0.81 (3)	1.91 (3)	2.7179 (19)	176 (2)
C9—H9···O4^iii	0.95	2.68	3.625 (2)	174
O3—H99C···O1^iv	0.99 (1)	1.48 (1)	2.4395 (18)	164 (2)

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