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The title compound, C9H13O4P, has been obtained by the reaction of dimethyl phosphite and benzaldehyde. In the crystal structure, inter­molecular O—H...O hydrogen bonds link the mol­ecules into infinite chains.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536806008294/dn2009sup1.cif
Contains datablocks I, global

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S1600536806008294/dn2009Isup2.hkl
Contains datablock I

CCDC reference: 605054

Key indicators

  • Single-crystal X-ray study
  • T = 273 K
  • Mean [sigma](C-C) = 0.005 Å
  • R factor = 0.067
  • wR factor = 0.186
  • Data-to-parameter ratio = 17.2

checkCIF/PLATON results

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Alert level C PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT331_ALERT_2_C Small Average Phenyl C-C Dist. C2 -C7 1.37 Ang. PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 5
0 ALERT level A = In general: serious problem 0 ALERT level B = Potentially serious problem 3 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 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 0 ALERT type 4 Improvement, methodology, query or suggestion

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SMART; data reduction: SAINT (Bruker, 2001); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 (Farrugia, 1997) and ViewerPro (Accelrys, 2001); software used to prepare material for publication: SHELXL97.

Dimethyl [hydroxy(phenyl)methyl]phosphonate top
Crystal data top
C9H13O4PF(000) = 456
Mr = 216.16Dx = 1.357 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 1831 reflections
a = 8.400 (3) Åθ = 2.3–25.6°
b = 7.737 (3) ŵ = 0.25 mm1
c = 16.477 (6) ÅT = 273 K
β = 98.949 (7)°Chunk, colorless
V = 1057.8 (7) Å30.46 × 0.20 × 0.18 mm
Z = 4
Data collection top
Bruker SMART APEX area-detector
diffractometer
2179 independent reflections
Radiation source: fine-focus sealed tube1728 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.044
φ and ω scansθmax = 26.5°, θmin = 2.5°
Absorption correction: multi-scan
(SADABS; Bruker, 2001)
h = 1010
Tmin = 0.895, Tmax = 0.957k = 99
5687 measured reflectionsl = 1220
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.067Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.186H-atom parameters constrained
S = 1.09 w = 1/[σ2(Fo2) + (0.1044P)2 + 0.0871P]
where P = (Fo2 + 2Fc2)/3
2179 reflections(Δ/σ)max < 0.001
127 parametersΔρmax = 0.49 e Å3
0 restraintsΔρmin = 0.33 e Å3
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
xyzUiso*/Ueq
P10.11340 (9)0.78363 (9)0.13207 (4)0.0453 (3)
O10.0949 (2)0.9695 (3)0.13511 (10)0.0504 (5)
C10.1471 (3)0.6782 (3)0.23049 (18)0.0466 (7)
H1A0.15460.55340.22150.056*
C20.0165 (4)0.7096 (3)0.27919 (18)0.0465 (7)
O20.0328 (3)0.6813 (3)0.08706 (13)0.0618 (6)
O30.2521 (3)0.7254 (3)0.08536 (14)0.0620 (6)
C30.1212 (4)0.6096 (4)0.2685 (2)0.0677 (9)
H3A0.13230.52250.22920.081*
O40.3003 (2)0.7388 (2)0.26797 (14)0.0544 (6)
H4B0.34410.66500.29950.082*
C40.2396 (5)0.6348 (6)0.3135 (3)0.0848 (12)
H4A0.33160.56630.30410.102*
C50.2269 (6)0.7580 (7)0.3720 (3)0.0901 (14)
H5A0.30780.77270.40400.108*
C60.0932 (5)0.8608 (6)0.3835 (2)0.0808 (12)
H6A0.08420.94770.42290.097*
C70.0276 (4)0.8377 (4)0.33782 (19)0.0576 (8)
H7A0.11790.90890.34640.069*
C80.3988 (5)0.8239 (5)0.0924 (3)0.0807 (11)
H8A0.47070.77060.05990.121*
H8B0.44890.82730.14890.121*
H8C0.37480.93940.07310.121*
C90.1256 (5)0.7375 (6)0.0130 (3)0.0942 (14)
H9A0.20910.65480.00440.141*
H9B0.05770.74840.02850.141*
H9C0.17320.84750.02160.141*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0481 (5)0.0417 (5)0.0439 (5)0.0026 (3)0.0002 (3)0.0018 (3)
O10.0539 (12)0.0463 (12)0.0481 (11)0.0003 (8)0.0014 (9)0.0034 (8)
C10.0433 (15)0.0379 (14)0.0545 (16)0.0010 (11)0.0049 (13)0.0016 (12)
C20.0468 (16)0.0437 (15)0.0458 (15)0.0020 (12)0.0031 (12)0.0113 (12)
O20.0656 (15)0.0610 (13)0.0525 (13)0.0160 (10)0.0109 (11)0.0021 (10)
O30.0696 (16)0.0580 (13)0.0599 (13)0.0064 (11)0.0142 (11)0.0127 (10)
C30.055 (2)0.070 (2)0.073 (2)0.0163 (16)0.0043 (17)0.0073 (17)
O40.0421 (12)0.0507 (11)0.0657 (13)0.0031 (8)0.0067 (10)0.0102 (9)
C40.053 (2)0.108 (3)0.092 (3)0.018 (2)0.007 (2)0.025 (3)
C50.070 (3)0.129 (4)0.078 (3)0.015 (3)0.030 (2)0.034 (3)
C60.089 (3)0.097 (3)0.059 (2)0.004 (2)0.021 (2)0.001 (2)
C70.0569 (19)0.0642 (19)0.0494 (17)0.0053 (15)0.0012 (14)0.0045 (15)
C80.069 (2)0.092 (3)0.088 (3)0.012 (2)0.031 (2)0.021 (2)
C90.082 (3)0.113 (3)0.075 (3)0.021 (2)0.028 (2)0.017 (2)
Geometric parameters (Å, º) top
P1—O11.448 (2)C4—C51.349 (6)
P1—O21.550 (2)C4—H4A0.9300
P1—O31.559 (2)C5—C61.365 (6)
P1—C11.798 (3)C5—H5A0.9300
C1—O41.418 (3)C6—C71.365 (5)
C1—C21.477 (4)C6—H6A0.9300
C1—H1A0.9800C7—H7A0.9300
C2—C71.377 (4)C8—H8A0.9600
C2—C31.380 (4)C8—H8B0.9600
O2—C91.410 (4)C8—H8C0.9600
O3—C81.438 (4)C9—H9A0.9600
C3—C41.343 (5)C9—H9B0.9600
C3—H3A0.9300C9—H9C0.9600
O4—H4B0.8200
O1—P1—O2116.25 (12)C5—C4—H4A119.6
O1—P1—O3113.35 (12)C4—C5—C6118.9 (4)
O2—P1—O3102.33 (13)C4—C5—H5A120.6
O1—P1—C1114.97 (12)C6—C5—H5A120.6
O2—P1—C1101.64 (13)C5—C6—C7120.9 (4)
O3—P1—C1106.82 (14)C5—C6—H6A119.6
O4—C1—C2114.2 (2)C7—C6—H6A119.6
O4—C1—P1104.33 (19)C6—C7—C2120.4 (3)
C2—C1—P1112.92 (19)C6—C7—H7A119.8
O4—C1—H1A108.4C2—C7—H7A119.8
C2—C1—H1A108.4O3—C8—H8A109.5
P1—C1—H1A108.4O3—C8—H8B109.5
C7—C2—C3117.2 (3)H8A—C8—H8B109.5
C7—C2—C1121.7 (3)O3—C8—H8C109.5
C3—C2—C1121.1 (3)H8A—C8—H8C109.5
C9—O2—P1123.2 (2)H8B—C8—H8C109.5
C8—O3—P1120.3 (2)O2—C9—H9A109.5
C4—C3—C2121.7 (4)O2—C9—H9B109.5
C4—C3—H3A119.1H9A—C9—H9B109.5
C2—C3—H3A119.1O2—C9—H9C109.5
C1—O4—H4B109.5H9A—C9—H9C109.5
C3—C4—C5120.9 (4)H9B—C9—H9C109.5
C3—C4—H4A119.6
O1—P1—C1—O466.3 (2)C1—P1—O2—C9166.7 (3)
O2—P1—C1—O4167.24 (17)O1—P1—O3—C837.0 (3)
O3—P1—C1—O460.4 (2)O2—P1—O3—C8163.0 (3)
O1—P1—C1—C258.2 (2)C1—P1—O3—C890.6 (3)
O2—P1—C1—C268.2 (2)C7—C2—C3—C40.3 (5)
O3—P1—C1—C2175.08 (19)C1—C2—C3—C4178.8 (3)
O4—C1—C2—C722.7 (4)C2—C3—C4—C51.1 (6)
P1—C1—C2—C796.3 (3)C3—C4—C5—C61.9 (6)
O4—C1—C2—C3156.3 (3)C4—C5—C6—C71.3 (6)
P1—C1—C2—C384.7 (3)C5—C6—C7—C20.0 (5)
O1—P1—O2—C941.1 (4)C3—C2—C7—C60.8 (5)
O3—P1—O2—C983.0 (3)C1—C2—C7—C6178.2 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O4—H4B···O1i0.821.882.689 (3)168
Symmetry code: (i) x+1/2, y1/2, z+1/2.
 

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