organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890

Di­methyl (1-hydr­­oxy-1,2-di­phenyl­ethyl)phospho­nate

aDepartment of Physics, University of Sargodha, Sargodha, Pakistan, bDepartment of Chemistry, Faculty of Science, University of Ankara, Ankara, Turkey, and cInstitute of Chemical and Pharmaceutical Sciences, The University of Faisalabad, Faisalabad, Pakistan
*Correspondence e-mail: dmntahir_uos@yahoo.com

(Received 25 July 2009; accepted 27 July 2009; online 31 July 2009)

In the crystal of the title compound, C16H19O4P, the mol­ecules are dimerized with R22(10) ring motifs through the hydr­oxy and P=O O atoms. The dihedral angle between the aromatic rings is 66.89 (9)°. There are ππ inter­actions [centroid–centroid distance = 3.9669 (16) Å] between the benzene rings of adjacent benzyl groups. A C—H⋯π inter­action between the aromatic rings where C—H is from a benzyl group is also present.

Related literature

For the preparation and crystal structures of α-hydr­oxy phospho­nates, see: Acar et al. (2009a[Acar, N., Tahir, M. N., Yılmaz, H., Chishti, M. S. A. & Malik, M. A. (2009a). Acta Cryst. E65, o481.],b[Acar, N., Tahir, M. N., Tariq, R. H. & Yilmaz, H. (2009b). Acta Cryst. E65, o1203.]); Tahir et al. (2007[Tahir, M. N., Acar, N., Yilmaz, H., Danish, M. & Ülkü, D. (2007). Acta Cryst. E63, o3817-o3818.], 2009a[Tahir, M. N., Acar, N., Yilmaz, H., Tariq, M. I. & Hussain, G. (2009a). Acta Cryst. E65, o939.],b[Tahir, M. N., Acar, N., Yilmaz, H., Tariq, M. I. & Ülkü, D. (2009b). Acta Cryst. E65, o562.]). For an isomer of the title compouns, see: Acar et al. (2009a[Acar, N., Tahir, M. N., Yılmaz, H., Chishti, M. S. A. & Malik, M. A. (2009a). Acta Cryst. E65, o481.]). For ring-motifs, see: Bernstein et al. (1995[Bernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555-1573.]).

[Scheme 1]

Experimental

Crystal data
  • C16H19O4P

  • Mr = 306.28

  • Monoclinic, P 21 /c

  • a = 8.4767 (5) Å

  • b = 15.8978 (10) Å

  • c = 13.3888 (7) Å

  • β = 119.397 (3)°

  • V = 1571.97 (17) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.19 mm−1

  • T = 296 K

  • 0.25 × 0.18 × 0.15 mm

Data collection
  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.963, Tmax = 0.974

  • 16757 measured reflections

  • 3861 independent reflections

  • 2183 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.047

  • wR(F2) = 0.126

  • S = 1.01

  • 3861 reflections

  • 195 parameters

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.27 e Å−3

  • Δρmin = −0.28 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
O1—H1⋯O2i 0.79 (2) 1.92 (2) 2.684 (2) 164 (3)
C12—H12⋯CgAii 0.93 2.86 3.755 (4) 163
Symmetry codes: (i) -x+2, -y+1, -z+1; (ii) [x-1, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]. CgA is the centroid of the C1–C6 ring.

Data collection: APEX2 (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2007[Bruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON .

Supporting information


Comment top

We have reported preparation and crystal structures containing α-Hydroxy phosphonates (Tahir et al., 2007, 2009a,b) and (Acar et al. 2009a,b). The title compound (I, Fig. 1) is chemically isomer of (II) (Acar et al., 2009a). The crystals of title compound were selected from the sample of Acar et al., 2009a present at low yield.

The difference of (I) with (II) exist due to various reasons. In (I) the dihedral angle between the aromatic rings A (C1–C6) and B (C9–C14) is 66.89 (9)° compared to 72.28 (11)°. The distorted tetrahedral geometry around C7 have range of angles 104.15 (13)° to 113.43 (16)° instead of 104.4 (2)° to 112.8 (2)°. There exist small variations in bond lengths e.g, P1—C7 is 1.835 (2) Å compared to 1.845 (3) Å. In (I) the molecules form dimers only and dimers are not linked to each other as observed in (II). The dimers (Fig. 2) are formed due to intermolecular H-bonding of O—H···O type with ring motif R22(10) (Bernstein et al., 1995). There exist C—H···π interaction between the two aromatic rings (Table 1) and ππ interaction at a distance of 3.9669 (16) Å between the centroids of aromatic ring B with CgB···CgBi [symmetry code: (i) 1 - x, 1 - y, -z].

Related literature top

For the preparation and crystal structures of α-hydroxy phosphonates, see: Acar et al. (2009a,b); Tahir et al. (2007, 2009a,b). For an isomer of the title compouns, see: Acar et al. (2009a). For ring-motifs, see: Bernstein et al. (1995).

Experimental top

The preparation is reported in Acar et al., 2009a.

Refinement top

The H-atom of hydroxy group were refined freely. The other H-atoms were positioned geometrically, with C—H = 0.93, 0.96 and 0.97 Å for aromatic, methyl and methylene H, and constrained to ride on their parent atoms, with Uiso(H) = xUeq(C,O), where x = 1.5 for methyl H, and x = 1.2 for all other H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2007); cell refinement: SAINT (Bruker, 2007); data reduction: SAINT (Bruker, 2007); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with the atom numbering scheme. The thermal ellipsoids are drawn at the 50% probability level. H-atoms are shown by small circles of arbitrary radii.
[Figure 2] Fig. 2. The partial packing (PLATON; Spek, 2009) which shows that molecules form dimers.
Dimethyl (1-hydroxy-1,2-diphenylethyl)phosphonate top
Crystal data top
C16H19O4PF(000) = 648
Mr = 306.28Dx = 1.294 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 3861 reflections
a = 8.4767 (5) Åθ = 2.8–28.3°
b = 15.8978 (10) ŵ = 0.19 mm1
c = 13.3888 (7) ÅT = 296 K
β = 119.397 (3)°Prismatic, colourless
V = 1571.97 (17) Å30.25 × 0.18 × 0.15 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3861 independent reflections
Radiation source: fine-focus sealed tube2183 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 7.40 pixels mm-1θmax = 28.3°, θmin = 2.8°
ω scansh = 1110
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
k = 2121
Tmin = 0.963, Tmax = 0.974l = 1717
16757 measured reflections
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)] = 0.047Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.01 w = 1/[σ2(Fo2) + (0.0517P)2 + 0.2804P]
where P = (Fo2 + 2Fc2)/3
3861 reflections(Δ/σ)max < 0.001
195 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.28 e Å3
Crystal data top
C16H19O4PV = 1571.97 (17) Å3
Mr = 306.28Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.4767 (5) ŵ = 0.19 mm1
b = 15.8978 (10) ÅT = 296 K
c = 13.3888 (7) Å0.25 × 0.18 × 0.15 mm
β = 119.397 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer
3861 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)
2183 reflections with I > 2σ(I)
Tmin = 0.963, Tmax = 0.974Rint = 0.043
16757 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0470 restraints
wR(F2) = 0.126H atoms treated by a mixture of independent and constrained refinement
S = 1.01Δρmax = 0.27 e Å3
3861 reflectionsΔρmin = 0.28 e Å3
195 parameters
Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

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
P11.16204 (7)0.38185 (3)0.45831 (5)0.0440 (2)
O10.83863 (19)0.37902 (9)0.43056 (13)0.0455 (5)
O21.20677 (18)0.46360 (9)0.51545 (14)0.0587 (5)
O31.25054 (19)0.36505 (11)0.38159 (14)0.0660 (6)
O41.2208 (2)0.30558 (10)0.54132 (14)0.0762 (6)
C10.8814 (2)0.27486 (12)0.31946 (16)0.0393 (6)
C20.9200 (3)0.24523 (14)0.23689 (18)0.0528 (8)
C30.8833 (3)0.16197 (17)0.2000 (2)0.0636 (9)
C40.8104 (3)0.10853 (16)0.2456 (2)0.0684 (9)
C50.7733 (3)0.13707 (15)0.3286 (2)0.0658 (9)
C60.8080 (3)0.21952 (13)0.3647 (2)0.0512 (8)
C70.9192 (2)0.36591 (12)0.36066 (16)0.0371 (6)
C80.8505 (3)0.43043 (13)0.26211 (17)0.0444 (7)
C90.6550 (3)0.41928 (13)0.17226 (18)0.0456 (7)
C100.6074 (4)0.38734 (16)0.0652 (2)0.0691 (9)
C110.4283 (5)0.37485 (19)0.0165 (2)0.0922 (11)
C120.2939 (4)0.39384 (18)0.0079 (3)0.0883 (11)
C130.3378 (3)0.42615 (17)0.1120 (3)0.0762 (10)
C140.5166 (3)0.43991 (14)0.1941 (2)0.0565 (8)
C151.4435 (3)0.36510 (19)0.4291 (3)0.0795 (11)
C161.3067 (5)0.3068 (2)0.6594 (3)0.1003 (15)
H10.844 (3)0.4272 (14)0.4467 (19)0.0546*
H20.970880.281150.205610.0634*
H30.908910.142850.143840.0763*
H40.785830.053020.220770.0821*
H50.724450.100610.360550.0789*
H60.781410.238140.420660.0615*
H8A0.866290.486510.294190.0533*
H8B0.924630.426290.225560.0533*
H100.697870.373960.047650.0829*
H110.399360.353490.088200.1106*
H120.173270.384690.046330.1061*
H130.246290.439340.128620.0914*
H140.543680.463210.264430.0678*
H15A1.488690.421330.450950.1196*
H15B1.473290.344720.372940.1196*
H15C1.497590.329260.495350.1196*
H16A1.424830.282230.689690.1505*
H16B1.236950.275180.685160.1505*
H16C1.318020.363880.685490.1505*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0404 (3)0.0400 (3)0.0461 (3)0.0007 (2)0.0169 (2)0.0084 (3)
O10.0601 (9)0.0362 (8)0.0526 (9)0.0011 (7)0.0373 (8)0.0051 (7)
O20.0475 (8)0.0454 (9)0.0735 (10)0.0043 (7)0.0221 (8)0.0213 (8)
O30.0412 (8)0.0905 (13)0.0680 (10)0.0029 (8)0.0282 (8)0.0230 (9)
O40.0837 (12)0.0515 (11)0.0533 (10)0.0049 (8)0.0027 (9)0.0020 (8)
C10.0361 (10)0.0373 (11)0.0383 (11)0.0022 (8)0.0134 (9)0.0029 (9)
C20.0604 (13)0.0521 (14)0.0467 (12)0.0047 (10)0.0268 (11)0.0044 (11)
C30.0687 (16)0.0608 (17)0.0498 (14)0.0114 (12)0.0203 (12)0.0182 (13)
C40.0593 (14)0.0453 (15)0.0803 (19)0.0029 (11)0.0185 (14)0.0198 (14)
C50.0632 (15)0.0430 (14)0.0912 (19)0.0100 (11)0.0380 (15)0.0106 (14)
C60.0529 (12)0.0425 (13)0.0643 (14)0.0049 (10)0.0334 (11)0.0079 (11)
C70.0403 (10)0.0355 (11)0.0379 (10)0.0005 (8)0.0211 (9)0.0020 (9)
C80.0472 (12)0.0397 (12)0.0494 (12)0.0004 (9)0.0261 (10)0.0038 (10)
C90.0516 (12)0.0355 (12)0.0430 (12)0.0005 (9)0.0181 (10)0.0072 (10)
C100.0815 (18)0.0677 (17)0.0464 (14)0.0126 (14)0.0223 (13)0.0061 (13)
C110.108 (2)0.074 (2)0.0480 (16)0.0089 (18)0.0023 (17)0.0025 (15)
C120.0672 (18)0.0561 (18)0.084 (2)0.0079 (14)0.0073 (16)0.0017 (16)
C130.0484 (14)0.0614 (18)0.096 (2)0.0007 (12)0.0179 (14)0.0064 (16)
C140.0518 (13)0.0459 (14)0.0631 (15)0.0036 (10)0.0215 (12)0.0023 (12)
C150.0484 (14)0.101 (2)0.093 (2)0.0057 (14)0.0377 (14)0.0070 (17)
C160.121 (3)0.102 (3)0.0607 (18)0.000 (2)0.0312 (19)0.0099 (18)
Geometric parameters (Å, º) top
P1—O21.4606 (16)C12—C131.355 (5)
P1—O31.5639 (19)C13—C141.385 (4)
P1—O41.5524 (17)C2—H20.9300
P1—C71.835 (2)C3—H30.9300
O1—C71.419 (3)C4—H40.9300
O3—C151.435 (4)C5—H50.9300
O4—C161.378 (4)C6—H60.9300
O1—H10.79 (2)C8—H8A0.9700
C1—C61.378 (3)C8—H8B0.9700
C1—C71.526 (3)C10—H100.9300
C1—C21.381 (3)C11—H110.9300
C2—C31.394 (3)C12—H120.9300
C3—C41.359 (4)C13—H130.9300
C4—C51.372 (4)C14—H140.9300
C5—C61.378 (3)C15—H15A0.9600
C7—C81.542 (3)C15—H15B0.9600
C8—C91.506 (3)C15—H15C0.9600
C9—C141.381 (4)C16—H16A0.9600
C9—C101.381 (3)C16—H16B0.9600
C10—C111.382 (5)C16—H16C0.9600
C11—C121.364 (6)
O1···O23.059 (2)C5···H16Av2.9000
O1···O43.056 (3)C6···H16Av2.9300
O1···C143.151 (3)C8···H22.8300
O1···C15i3.347 (4)C13···H5vii2.8800
O1···O2ii2.684 (2)C14···H15Bi3.0000
O2···O1ii2.684 (2)H1···O22.80 (3)
O2···O13.059 (2)H1···H8A2.3400
O3···C23.147 (3)H1···H142.5800
O4···C63.404 (3)H1···O2ii1.92 (2)
O4···C12iii3.303 (3)H2···O32.7300
O4···O13.056 (3)H2···C82.8300
O1···H62.2800H2···H8B2.3800
O1···H142.7400H2···H16Bviii2.5600
O1···H15Bi2.8500H3···O1viii2.6400
O1···H3iv2.6400H5···C13ix2.8800
O2···H12.80 (3)H5···H13ix2.5700
O2···H1ii1.92 (2)H6···O12.2800
O2···H16C2.5500H8A···H12.3400
O2···H14ii2.9000H8A···H142.5900
O3···H8B2.7000H8B···O32.7000
O3···H22.7300H8B···C22.8800
O4···H15C2.7300H8B···H22.3800
C1···C103.524 (3)H8B···H102.3600
C2···O33.147 (3)H10···C23.0800
C2···C93.398 (3)H10···H8B2.3600
C2···C103.381 (4)H12···C4v2.9700
C5···C16v3.574 (5)H12···C5v2.9700
C6···O43.404 (3)H13···H5vii2.5700
C9···C23.398 (3)H14···O12.7400
C10···C23.381 (4)H14···H12.5800
C10···C13.524 (3)H14···H8A2.5900
C12···O4v3.303 (3)H14···O2ii2.9000
C14···O13.151 (3)H15B···O1vi2.8500
C15···O1vi3.347 (4)H15B···C14vi3.0000
C16···C5iii3.574 (5)H15C···O42.7300
C2···H103.0800H15C···C3iii3.0700
C2···H8B2.8800H16A···C5iii2.9000
C3···H15Cv3.0700H16A···C6iii2.9300
C4···H12iii2.9700H16B···H2iv2.5600
C5···H12iii2.9700H16C···O22.5500
O2—P1—O3114.27 (10)C4—C3—H3120.00
O2—P1—O4114.23 (9)C3—C4—H4120.00
O2—P1—C7114.08 (10)C5—C4—H4120.00
O3—P1—O4104.36 (10)C4—C5—H5120.00
O3—P1—C7103.91 (9)C6—C5—H5120.00
O4—P1—C7104.81 (10)C1—C6—H6119.00
P1—O3—C15121.25 (18)C5—C6—H6119.00
P1—O4—C16127.83 (17)C7—C8—H8A109.00
C7—O1—H1109.9 (19)C7—C8—H8B109.00
C2—C1—C6118.02 (19)C9—C8—H8A109.00
C6—C1—C7120.45 (18)C9—C8—H8B109.00
C2—C1—C7121.52 (18)H8A—C8—H8B108.00
C1—C2—C3120.6 (2)C9—C10—H10119.00
C2—C3—C4120.4 (2)C11—C10—H10119.00
C3—C4—C5119.5 (2)C10—C11—H11120.00
C4—C5—C6120.3 (2)C12—C11—H11120.00
C1—C6—C5121.2 (2)C11—C12—H12120.00
P1—C7—C1110.58 (13)C13—C12—H12120.00
P1—C7—C8109.76 (15)C12—C13—H13119.00
O1—C7—C1107.11 (15)C14—C13—H13119.00
O1—C7—C8111.40 (17)C9—C14—H14120.00
C1—C7—C8113.43 (16)C13—C14—H14120.00
P1—C7—O1104.15 (13)O3—C15—H15A109.00
C7—C8—C9114.24 (19)O3—C15—H15B109.00
C8—C9—C10121.2 (3)O3—C15—H15C109.00
C10—C9—C14117.5 (2)H15A—C15—H15B110.00
C8—C9—C14121.3 (2)H15A—C15—H15C109.00
C9—C10—C11121.5 (3)H15B—C15—H15C109.00
C10—C11—C12120.0 (3)O4—C16—H16A109.00
C11—C12—C13119.4 (3)O4—C16—H16B109.00
C12—C13—C14121.2 (3)O4—C16—H16C109.00
C9—C14—C13120.5 (2)H16A—C16—H16B110.00
C1—C2—H2120.00H16A—C16—H16C109.00
C3—C2—H2120.00H16B—C16—H16C109.00
C2—C3—H3120.00
O2—P1—O3—C1559.8 (2)C2—C1—C7—C847.6 (3)
O4—P1—O3—C1565.7 (2)C6—C1—C7—P1103.4 (2)
C7—P1—O3—C15175.28 (19)C6—C1—C7—O19.5 (3)
O2—P1—O4—C160.5 (3)C6—C1—C7—C8132.8 (2)
O3—P1—O4—C16126.0 (3)C1—C2—C3—C40.6 (4)
C7—P1—O4—C16125.1 (3)C2—C3—C4—C50.1 (4)
O2—P1—C7—O156.34 (15)C3—C4—C5—C60.6 (4)
O2—P1—C7—C1171.09 (13)C4—C5—C6—C10.5 (4)
O2—P1—C7—C863.03 (17)P1—C7—C8—C9176.07 (16)
O3—P1—C7—O1178.59 (12)O1—C7—C8—C969.1 (2)
O3—P1—C7—C163.84 (15)C1—C7—C8—C951.8 (3)
O3—P1—C7—C862.04 (16)C7—C8—C9—C10106.8 (2)
O4—P1—C7—O169.34 (14)C7—C8—C9—C1472.6 (3)
O4—P1—C7—C145.42 (15)C8—C9—C10—C11178.2 (2)
O4—P1—C7—C8171.30 (14)C14—C9—C10—C111.2 (4)
C6—C1—C2—C30.8 (3)C8—C9—C14—C13177.5 (2)
C7—C1—C2—C3179.6 (2)C10—C9—C14—C132.0 (3)
C2—C1—C6—C50.2 (3)C9—C10—C11—C120.3 (4)
C7—C1—C6—C5179.9 (2)C10—C11—C12—C131.0 (4)
C2—C1—C7—P176.2 (2)C11—C12—C13—C140.2 (4)
C2—C1—C7—O1170.90 (19)C12—C13—C14—C91.3 (4)
Symmetry codes: (i) x1, y, z; (ii) x+2, y+1, z+1; (iii) x+1, y+1/2, z+1/2; (iv) x, y+1/2, z+1/2; (v) x1, y+1/2, z1/2; (vi) x+1, y, z; (vii) x+1, y+1/2, z+1/2; (viii) x, y+1/2, z1/2; (ix) x+1, y1/2, z+1/2.
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2ii0.79 (2)1.92 (2)2.684 (2)164 (3)
C6—H6···O10.932.282.655 (3)103.00
C16—H16C···O20.962.553.007 (4)110.00
C12—H12···CgAv0.932.863.755 (4)163.00
Symmetry codes: (ii) x+2, y+1, z+1; (v) x1, y+1/2, z1/2.

Experimental details

Crystal data
Chemical formulaC16H19O4P
Mr306.28
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)8.4767 (5), 15.8978 (10), 13.3888 (7)
β (°) 119.397 (3)
V3)1571.97 (17)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.25 × 0.18 × 0.15
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.963, 0.974
No. of measured, independent and
observed [I > 2σ(I)] reflections
16757, 3861, 2183
Rint0.043
(sin θ/λ)max1)0.666
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.047, 0.126, 1.01
No. of reflections3861
No. of parameters195
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.27, 0.28

Computer programs: APEX2 (Bruker, 2007), SAINT (Bruker, 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
O1—H1···O2i0.79 (2)1.92 (2)2.684 (2)164 (3)
C6—H6···O10.932.282.655 (3)103.00
C16—H16C···O20.962.553.007 (4)110.00
C12—H12···CgAii0.932.863.755 (4)163.00
Symmetry codes: (i) x+2, y+1, z+1; (ii) x1, y+1/2, z1/2.
 

Acknowledgements

The authors acknowledge the Higher Education Commission, Islamabad, Pakistan, and Bana International, Karachi, Pakistan, for funding the purchase of the diffractometer and for technical support, respectively.

References

First citationAcar, N., Tahir, M. N., Tariq, R. H. & Yilmaz, H. (2009b). Acta Cryst. E65, o1203.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationAcar, N., Tahir, M. N., Yılmaz, H., Chishti, M. S. A. & Malik, M. A. (2009a). Acta Cryst. E65, o481.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationBernstein, J., Davis, R. E., Shimoni, L. & Chang, N.-L. (1995). Angew. Chem. Int. Ed. Engl. 34, 1555–1573.  CrossRef CAS Web of Science Google Scholar
First citationBruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBruker (2007). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals Google Scholar
First citationFarrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838.  CrossRef CAS IUCr Journals Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationTahir, M. N., Acar, N., Yilmaz, H., Danish, M. & Ülkü, D. (2007). Acta Cryst. E63, o3817–o3818.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTahir, M. N., Acar, N., Yilmaz, H., Tariq, M. I. & Hussain, G. (2009a). Acta Cryst. E65, o939.  Web of Science CSD CrossRef IUCr Journals Google Scholar
First citationTahir, M. N., Acar, N., Yilmaz, H., Tariq, M. I. & Ülkü, D. (2009b). Acta Cryst. E65, o562.  Web of Science CSD CrossRef IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Follow Acta Cryst. E
Sign up for e-alerts
Follow Acta Cryst. on Twitter
Follow us on facebook
Sign up for RSS feeds