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.
Supporting information
CCDC reference: 232163
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.002 Å
- R factor = 0.044
- wR factor = 0.132
- Data-to-parameter ratio = 21.6
checkCIF/PLATON results
No syntax errors found
No errors found in this datablock
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
top
Crystal data top
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) Å3 | 0.4 × 0.3 × 0.2 mm |
Data collection top
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 top
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.044 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.132 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.10 | w = 1/[σ2(Fo2) + (0.0758P)2 + 0.1891P] where P = (Fo2 + 2Fc2)/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 top
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 (Å2) top | 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 (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
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) top
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) top
D—H···A | D—H | H···A | D···A | D—H···A |
O6—H2···O4i | 0.84 (4) | 2.06 (4) | 2.894 (2) | 171 (3) |
O6—H1···O1ii | 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. |