organic compounds
Diisopropylammonium hydrogen phenylphosphonate
aLaboratoire de Chimie Minerale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Senegal, and bCNRS, Universite de Bordeaux, ICMCB, 87 Avenue du Dr A. Schweitzer, Pessac F-33608, France
*Correspondence e-mail: mouhasboye@hotmail.com
In the title salt, [(CH3)2CH]2NH2]+·[C6H5PO2(OH)]−, the anions are linked by pairs of O—H⋯O hydrogen bonds, forming inversion dimers. These dimers are bridged by the cations via N—H⋯O hydrogen bonds, leading to a three-dimensional structure.
Related literature
For crystal structures of closely related compounds, see: Diop et al. (2012); Beckmann et al. (2003).
Experimental
Crystal data
|
Refinement
|
Data collection: COLLECT (Hooft, 1998); cell HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).
Supporting information
10.1107/S1600536812041086/pv2589sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041086/pv2589Isup2.hkl
The title compound was synthesized by mixing [(CH3)2CH]2NH and PhPO3H2 in water (1/1 ratio). The precipitate obtained was filtered. The crystals suitable for X-ray crystallographic analysis were grown from a solution of water by slow evaporation at room temperature.
All H atoms were located from difference maps and were allowed to refine freely with Uiso.
Data collection: COLLECT (Hooft, 1998); cell
HKL DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: publCIF (Westrip, 2010).C6H16N+·C6H6O3P− | F(000) = 560 |
Mr = 259.28 | Dx = 1.259 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 4223 reflections |
a = 11.9166 (2) Å | θ = 0.4–30.0° |
b = 9.0982 (1) Å | µ = 0.20 mm−1 |
c = 12.8539 (1) Å | T = 293 K |
β = 101.013 (1)° | Prism, colourless |
V = 1367.95 (3) Å3 | 0.88 × 0.63 × 0.25 mm |
Z = 4 |
Nonius KappaCCD diffractometer | 3990 independent reflections |
Radiation source: fine-focus sealed tube | 3626 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.013 |
ϕ scans, and ω scans with κ | θmax = 30.1°, θmin = 3.2° |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | h = −16→16 |
Tmin = 0.845, Tmax = 0.952 | k = −12→12 |
7738 measured reflections | l = −18→18 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.029 | All H-atom parameters refined |
wR(F2) = 0.080 | w = 1/[σ2(Fo2) + (0.0397P)2 + 0.4747P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max = 0.001 |
3990 reflections | Δρmax = 0.38 e Å−3 |
243 parameters | Δρmin = −0.33 e Å−3 |
0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.013 (2) |
C6H16N+·C6H6O3P− | V = 1367.95 (3) Å3 |
Mr = 259.28 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 11.9166 (2) Å | µ = 0.20 mm−1 |
b = 9.0982 (1) Å | T = 293 K |
c = 12.8539 (1) Å | 0.88 × 0.63 × 0.25 mm |
β = 101.013 (1)° |
Nonius KappaCCD diffractometer | 3990 independent reflections |
Absorption correction: multi-scan (SCALEPACK; Otwinowski & Minor, 1997) | 3626 reflections with I > 2σ(I) |
Tmin = 0.845, Tmax = 0.952 | Rint = 0.013 |
7738 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.080 | All H-atom parameters refined |
S = 1.03 | Δρmax = 0.38 e Å−3 |
3990 reflections | Δρmin = −0.33 e Å−3 |
243 parameters |
Experimental. The analytical data - % calculated (% found): C: 55.59 (55.64); H: 8.55 (8.91); N: 5.40 (5.58). Infrared data (cm-1) [br= broad; s= strong; m=medium] 2694br νNH; 1148m, 1129 s, 1059, 1027m νPO3; 898 s δPO3; 752 m νPC; 708 s, 696 s νPh. Melting point = 437–438 K |
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.966159 (19) | 0.40247 (2) | 0.846319 (17) | 0.01271 (8) | |
O2 | 1.04330 (6) | 0.32302 (7) | 0.94386 (5) | 0.01729 (14) | |
N1 | 0.66048 (7) | 0.51553 (9) | 0.78554 (6) | 0.01430 (15) | |
C1 | 1.06532 (7) | 0.49048 (10) | 0.77593 (7) | 0.01453 (17) | |
C6 | 1.14485 (9) | 0.59178 (11) | 0.82778 (8) | 0.0222 (2) | |
C12 | 0.62928 (8) | 0.41946 (10) | 0.68876 (8) | 0.01742 (18) | |
C13 | 0.69808 (9) | 0.47210 (12) | 0.60787 (8) | 0.0225 (2) | |
C2 | 1.06337 (9) | 0.46114 (11) | 0.66912 (8) | 0.01979 (19) | |
C4 | 1.21864 (9) | 0.63037 (13) | 0.66783 (9) | 0.0270 (2) | |
C3 | 1.13968 (9) | 0.53095 (13) | 0.61530 (9) | 0.0256 (2) | |
C5 | 1.22118 (10) | 0.66111 (13) | 0.77426 (10) | 0.0287 (2) | |
O1 | 0.89926 (6) | 0.29081 (8) | 0.77497 (5) | 0.02025 (15) | |
C8 | 0.60257 (8) | 0.48352 (11) | 0.87717 (8) | 0.01757 (18) | |
C9 | 0.64492 (9) | 0.59615 (12) | 0.96314 (8) | 0.0215 (2) | |
C11 | 0.50164 (9) | 0.42810 (13) | 0.64537 (9) | 0.0245 (2) | |
C10 | 0.62574 (10) | 0.32619 (12) | 0.91508 (9) | 0.0257 (2) | |
O3 | 0.89542 (5) | 0.52144 (7) | 0.88605 (5) | 0.01657 (14) | |
H6 | 1.0624 (16) | 0.376 (2) | 0.9984 (15) | 0.054 (5)* | |
H17 | 0.7362 (12) | 0.5109 (14) | 0.8110 (11) | 0.022 (3)* | |
H16 | 0.6429 (12) | 0.6104 (16) | 0.7649 (11) | 0.028 (3)* | |
H21 | 0.5218 (11) | 0.4980 (14) | 0.8513 (10) | 0.018 (3)* | |
H18 | 0.6510 (11) | 0.3197 (15) | 0.7094 (10) | 0.020 (3)* | |
H10 | 0.6767 (12) | 0.5719 (16) | 0.5864 (11) | 0.029 (4)* | |
H7 | 0.7279 (12) | 0.5857 (15) | 0.9907 (11) | 0.027 (3)* | |
H12 | 0.6818 (13) | 0.4116 (16) | 0.5460 (12) | 0.034 (4)* | |
H9 | 0.6088 (13) | 0.5821 (17) | 1.0245 (12) | 0.036 (4)* | |
H11 | 0.7788 (13) | 0.4705 (16) | 0.6362 (12) | 0.032 (4)* | |
H8 | 0.6298 (13) | 0.6961 (18) | 0.9372 (12) | 0.035 (4)* | |
H13 | 0.4820 (12) | 0.3727 (17) | 0.5783 (12) | 0.034 (4)* | |
H20 | 0.7076 (13) | 0.3059 (16) | 0.9306 (11) | 0.029 (3)* | |
H19 | 0.5963 (13) | 0.3128 (18) | 0.9806 (13) | 0.041 (4)* | |
H15 | 0.4790 (13) | 0.5297 (17) | 0.6277 (12) | 0.034 (4)* | |
H14 | 0.4571 (13) | 0.3869 (16) | 0.6953 (12) | 0.034 (4)* | |
H22 | 0.5884 (13) | 0.2571 (18) | 0.8637 (13) | 0.038 (4)* | |
H5 | 1.1462 (12) | 0.6131 (15) | 0.9024 (11) | 0.028 (3)* | |
H3 | 1.2709 (13) | 0.6789 (17) | 0.6323 (12) | 0.037 (4)* | |
H4 | 1.2746 (13) | 0.7291 (18) | 0.8131 (12) | 0.040 (4)* | |
H2 | 1.1388 (13) | 0.5080 (17) | 0.5413 (12) | 0.034 (4)* | |
H1 | 1.0101 (12) | 0.3924 (16) | 0.6328 (11) | 0.027 (3)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.01307 (12) | 0.01214 (12) | 0.01264 (12) | −0.00065 (7) | 0.00175 (8) | −0.00020 (7) |
O2 | 0.0219 (3) | 0.0150 (3) | 0.0141 (3) | 0.0025 (2) | 0.0012 (2) | 0.0012 (2) |
N1 | 0.0134 (3) | 0.0143 (3) | 0.0154 (3) | 0.0003 (3) | 0.0031 (3) | 0.0005 (3) |
C1 | 0.0141 (4) | 0.0135 (4) | 0.0161 (4) | 0.0019 (3) | 0.0032 (3) | 0.0015 (3) |
C6 | 0.0229 (5) | 0.0226 (5) | 0.0214 (5) | −0.0063 (4) | 0.0051 (4) | −0.0012 (4) |
C12 | 0.0184 (4) | 0.0157 (4) | 0.0179 (4) | 0.0004 (3) | 0.0027 (3) | −0.0029 (3) |
C13 | 0.0214 (5) | 0.0297 (5) | 0.0171 (4) | 0.0020 (4) | 0.0049 (4) | −0.0015 (4) |
C2 | 0.0207 (4) | 0.0222 (5) | 0.0171 (4) | 0.0005 (4) | 0.0052 (3) | −0.0001 (3) |
C4 | 0.0241 (5) | 0.0279 (5) | 0.0321 (6) | 0.0004 (4) | 0.0129 (4) | 0.0102 (4) |
C3 | 0.0275 (5) | 0.0309 (6) | 0.0209 (5) | 0.0033 (4) | 0.0110 (4) | 0.0049 (4) |
C5 | 0.0262 (5) | 0.0280 (5) | 0.0326 (6) | −0.0105 (4) | 0.0077 (4) | 0.0014 (4) |
O1 | 0.0231 (3) | 0.0169 (3) | 0.0193 (3) | −0.0056 (3) | 0.0003 (3) | −0.0021 (3) |
C8 | 0.0148 (4) | 0.0209 (4) | 0.0182 (4) | 0.0006 (3) | 0.0064 (3) | 0.0026 (3) |
C9 | 0.0228 (5) | 0.0247 (5) | 0.0179 (4) | 0.0034 (4) | 0.0065 (4) | −0.0007 (4) |
C11 | 0.0190 (4) | 0.0267 (5) | 0.0263 (5) | −0.0035 (4) | 0.0005 (4) | −0.0067 (4) |
C10 | 0.0306 (5) | 0.0215 (5) | 0.0264 (5) | −0.0017 (4) | 0.0089 (4) | 0.0066 (4) |
O3 | 0.0137 (3) | 0.0197 (3) | 0.0161 (3) | 0.0026 (2) | 0.0023 (2) | −0.0017 (2) |
P1—O1 | 1.4932 (7) | C2—C3 | 1.3962 (14) |
P1—O3 | 1.5191 (7) | C2—H1 | 0.948 (14) |
P1—O2 | 1.5809 (7) | C4—C3 | 1.3845 (17) |
P1—C1 | 1.8068 (9) | C4—C5 | 1.3910 (16) |
O2—H6 | 0.847 (19) | C4—H3 | 0.949 (15) |
N1—C8 | 1.5030 (12) | C3—H2 | 0.972 (15) |
N1—C12 | 1.5077 (12) | C5—H4 | 0.957 (16) |
N1—H17 | 0.900 (14) | C8—C10 | 1.5202 (14) |
N1—H16 | 0.916 (15) | C8—C9 | 1.5208 (14) |
C1—C2 | 1.3945 (13) | C8—H21 | 0.965 (13) |
C1—C6 | 1.3966 (13) | C9—H7 | 0.989 (15) |
C6—C5 | 1.3920 (14) | C9—H9 | 0.976 (15) |
C6—H5 | 0.976 (14) | C9—H8 | 0.973 (16) |
C12—C11 | 1.5188 (14) | C11—H13 | 0.987 (15) |
C12—C13 | 1.5193 (14) | C11—H15 | 0.977 (16) |
C12—H18 | 0.967 (13) | C11—H14 | 0.982 (15) |
C13—H10 | 0.969 (15) | C10—H20 | 0.976 (15) |
C13—H12 | 0.957 (15) | C10—H19 | 0.980 (16) |
C13—H11 | 0.961 (15) | C10—H22 | 0.957 (16) |
O1—P1—O3 | 115.20 (4) | C3—C4—C5 | 119.74 (9) |
O1—P1—O2 | 109.72 (4) | C3—C4—H3 | 121.1 (9) |
O3—P1—O2 | 109.58 (4) | C5—C4—H3 | 119.1 (9) |
O1—P1—C1 | 108.51 (4) | C4—C3—C2 | 120.12 (10) |
O3—P1—C1 | 108.10 (4) | C4—C3—H2 | 119.8 (9) |
O2—P1—C1 | 105.24 (4) | C2—C3—H2 | 120.1 (9) |
P1—O2—H6 | 114.8 (12) | C4—C5—C6 | 120.10 (10) |
C8—N1—C12 | 117.16 (7) | C4—C5—H4 | 122.1 (10) |
C8—N1—H17 | 106.5 (8) | C6—C5—H4 | 117.8 (10) |
C12—N1—H17 | 110.1 (8) | N1—C8—C10 | 110.56 (8) |
C8—N1—H16 | 107.3 (9) | N1—C8—C9 | 107.49 (8) |
C12—N1—H16 | 107.5 (9) | C10—C8—C9 | 112.76 (9) |
H17—N1—H16 | 107.9 (12) | N1—C8—H21 | 106.3 (7) |
C2—C1—C6 | 118.58 (9) | C10—C8—H21 | 110.3 (8) |
C2—C1—P1 | 121.24 (7) | C9—C8—H21 | 109.2 (7) |
C6—C1—P1 | 120.17 (7) | C8—C9—H7 | 111.5 (8) |
C5—C6—C1 | 120.74 (10) | C8—C9—H9 | 111.2 (9) |
C5—C6—H5 | 120.4 (8) | H7—C9—H9 | 105.2 (12) |
C1—C6—H5 | 118.8 (8) | C8—C9—H8 | 111.5 (9) |
N1—C12—C11 | 110.17 (8) | H7—C9—H8 | 108.6 (12) |
N1—C12—C13 | 107.55 (8) | H9—C9—H8 | 108.5 (12) |
C11—C12—C13 | 111.46 (9) | C12—C11—H13 | 110.3 (8) |
N1—C12—H18 | 107.9 (8) | C12—C11—H15 | 110.3 (9) |
C11—C12—H18 | 110.2 (8) | H13—C11—H15 | 105.8 (12) |
C13—C12—H18 | 109.5 (7) | C12—C11—H14 | 111.6 (9) |
C12—C13—H10 | 110.1 (8) | H13—C11—H14 | 108.0 (12) |
C12—C13—H12 | 109.8 (9) | H15—C11—H14 | 110.7 (12) |
H10—C13—H12 | 107.5 (12) | C8—C10—H20 | 110.9 (8) |
C12—C13—H11 | 111.6 (9) | C8—C10—H19 | 108.6 (9) |
H10—C13—H11 | 108.2 (12) | H20—C10—H19 | 108.0 (12) |
H12—C13—H11 | 109.6 (12) | C8—C10—H22 | 111.4 (9) |
C1—C2—C3 | 120.72 (10) | H20—C10—H22 | 109.3 (12) |
C1—C2—H1 | 119.7 (8) | H19—C10—H22 | 108.3 (13) |
C3—C2—H1 | 119.6 (8) | ||
O1—P1—C1—C2 | 6.07 (9) | C8—N1—C12—C13 | −179.89 (8) |
O3—P1—C1—C2 | −119.51 (8) | C6—C1—C2—C3 | 0.34 (14) |
O2—P1—C1—C2 | 123.46 (8) | P1—C1—C2—C3 | 179.35 (8) |
O1—P1—C1—C6 | −174.93 (8) | C5—C4—C3—C2 | −0.39 (17) |
O3—P1—C1—C6 | 59.48 (8) | C1—C2—C3—C4 | 0.11 (16) |
O2—P1—C1—C6 | −57.55 (8) | C3—C4—C5—C6 | 0.21 (18) |
C2—C1—C6—C5 | −0.53 (15) | C1—C6—C5—C4 | 0.26 (17) |
P1—C1—C6—C5 | −179.55 (8) | C12—N1—C8—C10 | 58.07 (11) |
C8—N1—C12—C11 | 58.44 (11) | C12—N1—C8—C9 | −178.48 (8) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H17···O3 | 0.900 (14) | 1.960 (14) | 2.8510 (10) | 170.3 (12) |
O2—H6···O3i | 0.847 (19) | 1.744 (19) | 2.5895 (10) | 177.4 (19) |
N1—H16···O1ii | 0.916 (15) | 1.764 (15) | 2.6782 (10) | 176.7 (13) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+3/2, y+1/2, −z+3/2. |
Experimental details
Crystal data | |
Chemical formula | C6H16N+·C6H6O3P− |
Mr | 259.28 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 293 |
a, b, c (Å) | 11.9166 (2), 9.0982 (1), 12.8539 (1) |
β (°) | 101.013 (1) |
V (Å3) | 1367.95 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.20 |
Crystal size (mm) | 0.88 × 0.63 × 0.25 |
Data collection | |
Diffractometer | Nonius KappaCCD diffractometer |
Absorption correction | Multi-scan (SCALEPACK; Otwinowski & Minor, 1997) |
Tmin, Tmax | 0.845, 0.952 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 7738, 3990, 3626 |
Rint | 0.013 |
(sin θ/λ)max (Å−1) | 0.705 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.080, 1.03 |
No. of reflections | 3990 |
No. of parameters | 243 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.38, −0.33 |
Computer programs: COLLECT (Hooft, 1998), HKL DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), publCIF (Westrip, 2010).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H17···O3 | 0.900 (14) | 1.960 (14) | 2.8510 (10) | 170.3 (12) |
O2—H6···O3i | 0.847 (19) | 1.744 (19) | 2.5895 (10) | 177.4 (19) |
N1—H16···O1ii | 0.916 (15) | 1.764 (15) | 2.6782 (10) | 176.7 (13) |
Symmetry codes: (i) −x+2, −y+1, −z+2; (ii) −x+3/2, y+1/2, −z+3/2. |
References
Beckmann, J., Dakternieks, D. & Duthie, A. (2003). Appl. Organomet. Chem. 17, 817–818. Web of Science CSD CrossRef CAS Google Scholar
Diop, T., Diop, L., Maris, T. & Stoeckli-Evans, H. (2012). Acta Cryst. E68, o1432. CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Hooft, R. (1998). COLLECT. Nonius BV, Delft, The Netherlands. Google Scholar
Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307–326. New York: Academic Press. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS 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.
In the assymmetric unit of the title salt (Fig. 1), the anion, hydrogen phenylphosphonate (PhPO3H-), adopts a tetrahedral geometry, with three oxygen atoms and a benzene group with O—P—O and O—P—C angles in the ranges 109.58 (4) - 115.20 (4) and 105.24 (4) - 108.51 (4)°, respectively. Two P—O distances in the anion are close, (P1—O1 = 1.4932 (7) and P1—O3 = 1.5191 (7) Å) indicating the presence of extensive π-delocalization of the P═O double bonds. The bond distance P1—O2 (1.5809 (7) Å for P—OH bond) is significantly longer than the other two P—O bonds. The P—O bond distances in the title salt agree very well with the corresponding bond distances reported in closely related compounds (Diop et al., 2012; Beckmann et al., 2003).
In the crystal, the anions are connected by O2—H6···O3 hydrogen bonds forming dimers about inversion centers. These pairs are then bridged through cations via N—H···O hydrogen bonds leading to a three-dimensional structure (Tab. 1 & Fig. 2).