3-Chloro­methyl-5-methoxy-4-methoxy­carbonyl-3-oxo-2,3-di­hydro-[1,3]­oxa­phospho­le monohydrate

The title compound crystallizes as a monohydrate, C₇H₁₀PO₅Cl·H₂O. In the crystal structure, two symmetry-related oxa­phospho­le mol­ecules are linked through hydrogen bonds with the water mol­ecule of crystallization.

Key indicators

• Single-crystal X-ray study
• T = 293 K
• Mean [sigma](C-C) = 0.002 Å
• R factor = 0.044
• wR factor = 0.132
• Data-to-parameter ratio = 21.6

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Computing details

Data collection: CrysAlis CCD (Oxford Diffraction, 2001); cell refinement: CrysAlis RED (Oxford Diffraction, 2001); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: SHELXL97.

3-Chloromethyl-5-methoxy-4-methoxycarbonyl-3-oxo-2,3-dihydro-[1,3]oxaphosphole monohydrate

Crystal data

C7H10ClO5P·H2O	Z = 2
Mr = 258.59	F(000) = 268
Triclinic, P1	Dx = 1.601 Mg m^−3
Hall symbol: -P 1	Melting point = 138–141 K
a = 7.6307 (7) Å	Mo Kα radiation, λ = 0.71073 Å
b = 8.5404 (8) Å	Cell parameters from 9001 reflections
c = 9.1204 (10) Å	θ = 3.5–30.1°
α = 71.019 (9)°	µ = 0.51 mm^−1
β = 81.102 (8)°	T = 293 K
γ = 72.999 (8)°	Platelet, colourless
V = 536.32 (10) Å^3	0.4 × 0.3 × 0.2 mm

Data collection

Xcalibur CCD diffractometer	2695 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.040
Graphite monochromator	θmax = 30.1°, θmin = 3.5°
ω scans	h = −10→10
9001 measured reflections	k = −12→11
3113 independent reflections	l = −12→12

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)] = 0.044	Hydrogen site location: inferred from neighbouring sites
wR(F^2) = 0.132	H atoms treated by a mixture of independent and constrained refinement
S = 1.10	w = 1/[σ^2(Fo^2) + (0.0758P)^2 + 0.1891P] where P = (Fo^2 + 2Fc^2)/3
3113 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.47 e Å^−3
0 restraints	Δρmin = −0.45 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
P	0.36759 (5)	0.69408 (4)	0.82745 (4)	0.02557 (13)
Cl	−0.00672 (8)	0.80604 (7)	0.96993 (7)	0.05509 (18)
O1	0.50776 (17)	0.53792 (15)	0.80730 (16)	0.0361 (3)
O5	0.22169 (18)	0.74863 (15)	0.52642 (14)	0.0346 (3)
O3	0.32144 (19)	1.17011 (14)	0.61276 (14)	0.0353 (3)
O2	0.40360 (17)	0.98834 (14)	0.84540 (13)	0.0319 (3)
O4	0.2231 (2)	1.02359 (18)	0.41208 (15)	0.0466 (4)
C4	0.3177 (2)	0.88087 (18)	0.66978 (16)	0.0258 (3)
O6	0.1405 (2)	0.3935 (2)	0.2929 (2)	0.0510 (4)
H1	0.239 (4)	0.420 (4)	0.286 (3)	0.056 (8)*
H2	0.170 (4)	0.287 (5)	0.335 (4)	0.077 (10)*
C3	0.3476 (2)	1.01447 (18)	0.70581 (17)	0.0259 (3)
C2	0.4349 (3)	0.8095 (2)	0.93891 (19)	0.0355 (4)
H21	0.3621	0.8001	1.0370	0.043*
H22	0.5634	0.7614	0.9605	0.043*
C6	0.2507 (2)	0.89749 (19)	0.52336 (17)	0.0271 (3)
C1	0.1581 (2)	0.6352 (2)	0.91731 (19)	0.0321 (3)
H11	0.1065	0.6008	0.8456	0.039*
H12	0.1866	0.5378	1.0094	0.039*
C7	0.1483 (3)	0.7476 (3)	0.3904 (2)	0.0413 (4)
H71	0.1331	0.6357	0.4050	0.050*
H72	0.2315	0.7758	0.3015	0.050*
H73	0.0315	0.8305	0.3742	0.050*
C5	0.3362 (3)	1.3083 (2)	0.6659 (2)	0.0435 (4)
H51	0.3142	1.4133	0.5822	0.052*
H52	0.4572	1.2826	0.6997	0.052*
H53	0.2471	1.3203	0.7508	0.052*

Atomic displacement parameters (Ų)

	U^11	U^22	U^33	U^12	U^13	U^23
P	0.0310 (2)	0.01978 (19)	0.0254 (2)	−0.00599 (14)	−0.00493 (14)	−0.00516 (14)
Cl	0.0516 (3)	0.0480 (3)	0.0578 (3)	−0.0046 (2)	0.0133 (2)	−0.0203 (2)
O1	0.0363 (6)	0.0241 (5)	0.0454 (7)	−0.0033 (4)	−0.0053 (5)	−0.0100 (5)
O5	0.0506 (7)	0.0271 (5)	0.0315 (6)	−0.0122 (5)	−0.0118 (5)	−0.0098 (4)
O3	0.0542 (7)	0.0218 (5)	0.0325 (6)	−0.0139 (5)	−0.0125 (5)	−0.0033 (4)
O2	0.0461 (6)	0.0256 (5)	0.0276 (5)	−0.0110 (5)	−0.0104 (5)	−0.0075 (4)
O4	0.0778 (10)	0.0357 (7)	0.0292 (6)	−0.0233 (7)	−0.0183 (6)	0.0006 (5)
C4	0.0336 (7)	0.0220 (6)	0.0231 (6)	−0.0095 (5)	−0.0038 (5)	−0.0054 (5)
O6	0.0514 (9)	0.0412 (8)	0.0561 (9)	−0.0189 (7)	−0.0115 (7)	0.0011 (7)
C3	0.0298 (7)	0.0239 (6)	0.0249 (6)	−0.0082 (5)	−0.0044 (5)	−0.0063 (5)
C2	0.0511 (9)	0.0276 (7)	0.0289 (7)	−0.0105 (6)	−0.0159 (7)	−0.0037 (6)
C6	0.0327 (7)	0.0256 (6)	0.0250 (6)	−0.0091 (5)	−0.0023 (5)	−0.0085 (5)
C1	0.0378 (8)	0.0266 (7)	0.0305 (7)	−0.0107 (6)	−0.0007 (6)	−0.0051 (6)
C7	0.0494 (10)	0.0441 (10)	0.0401 (9)	−0.0122 (8)	−0.0130 (8)	−0.0205 (8)
C5	0.0596 (11)	0.0260 (8)	0.0510 (11)	−0.0156 (7)	−0.0086 (9)	−0.0132 (7)

Geometric parameters (Å, º)

P—O1	1.4903 (12)	C4—C6	1.453 (2)
P—C4	1.7549 (15)	O6—H1	0.83 (3)
P—C1	1.8099 (17)	O6—H2	0.84 (4)
P—C2	1.8382 (17)	C2—H21	0.9700
Cl—C1	1.7709 (18)	C2—H22	0.9700
O5—C6	1.3437 (18)	C1—H11	0.9700
O5—C7	1.441 (2)	C1—H12	0.9700
O3—C3	1.3001 (18)	C7—H71	0.9600
O3—C5	1.451 (2)	C7—H72	0.9600
O2—C3	1.3345 (17)	C7—H73	0.9600
O2—C2	1.4558 (19)	C5—H51	0.9600
O4—C6	1.2070 (19)	C5—H52	0.9600
C4—C3	1.371 (2)	C5—H53	0.9600
O1—P—C4	120.36 (7)	O4—C6—O5	122.81 (14)
O1—P—C1	108.78 (8)	O4—C6—C4	127.01 (14)
C4—P—C1	110.15 (7)	O5—C6—C4	110.18 (12)
O1—P—C2	115.76 (8)	Cl—C1—P	112.11 (9)
C4—P—C2	91.11 (7)	Cl—C1—H11	109.2
C1—P—C2	109.48 (9)	P—C1—H11	109.2
C6—O5—C7	116.44 (13)	Cl—C1—H12	109.2
C3—O3—C5	120.72 (13)	P—C1—H12	109.2
C3—O2—C2	112.11 (12)	H11—C1—H12	107.9
C3—C4—C6	123.79 (13)	O5—C7—H71	109.5
C3—C4—P	109.59 (10)	O5—C7—H72	109.5
C6—C4—P	126.60 (11)	H71—C7—H72	109.5
H1—O6—H2	103 (3)	O5—C7—H73	109.5
O3—C3—O2	116.22 (13)	H71—C7—H73	109.5
O3—C3—C4	124.17 (13)	H72—C7—H73	109.5
O2—C3—C4	119.60 (13)	O3—C5—H51	109.5
O2—C2—P	107.46 (10)	O3—C5—H52	109.5
O2—C2—H21	110.2	H51—C5—H52	109.5
P—C2—H21	110.2	O3—C5—H53	109.5
O2—C2—H22	110.2	H51—C5—H53	109.5
P—C2—H22	110.2	H52—C5—H53	109.5
H21—C2—H22	108.5

Hydrogen-bond geometry (Å, º)

D—H···A	D—H	H···A	D···A	D—H···A
O6—H2···O4^i	0.84 (4)	2.06 (4)	2.894 (2)	171 (3)
O6—H1···O1^ii	0.83 (3)	2.06 (4)	2.863 (2)	159 (3)

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