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organic compounds
(RP)-Menthyl (1-hydroxycyclohexyl)phenylphosphinate
aCollege of Chemistry and Chemical Engineering, Liaocheng University, Shandong 252059, People's Republic of China
*Correspondence e-mail: literabc@hotmail.com
The title compound, C22H35O3P, features a tetrahedral P atom bonded to a phenyl ring, a hydroxycyclohexyl unit and the O atom of a menthyl group. The axial at phosphorus is RP. In the crystal, molecules are connected through O—H⋯O hydrogen bonds involving the hydroxy and P=O groups, forming chains along the 21 screw axis. The methyl groups of the isopropyl fragment in the menthyl unit are disordered over two sites of equal occupancy.
Related literature
For general background to α-hydroxy alkylphosphonates, see: Kim & Wiemer (2003). For the structures of related phenylphosphinates, see: Sheldrick et al. (1981
); Chaloner et al. (1991
); Grice et al. (2004
).
Experimental
Crystal data
|
|
Data collection: SMART (Siemens, 1996); cell SAINT (Siemens, 1996
); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008
); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008
); molecular graphics: SHELXTL (Sheldrick, 2008
); software used to prepare material for publication: SHELXTL.
Supporting information
10.1107/S1600536810009219/bh2267sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536810009219/bh2267Isup2.hkl
Cyclohexanone was added to a stirred DMF solution of (RP)-menthyl-phenylphosphinate in a flask and the mixture was stirred for 48 h at room temperature. After washing with water, the resulting solid was dried, and recrystallized from diethyl ether, to afford the pure title product.
Atoms C14 and C15 were found to be disordered over two sites, and the ratio of the occupancy factors was fixed to 0.50:0.50 and 0.50:0.50 for atoms C14:C14'and C15:C15', respectively. All H atoms attached to C atoms were fixed geometrically and treated as riding with C—H = 0.93–0.98 Å, and with Uiso(H) = 1.2 Ueq(C) or 1.5 Ueq(C) for the methyl groups. Atom H3 was found in a difference map and refined with free coordinates, converging to O—H = 0.76 (3) Å. Assignment of
is based on measurement of 1685 Friedel pairs.Data collection: SMART (Siemens, 1996); cell
SAINT (Siemens, 1996); data reduction: SAINT (Siemens, 1996); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008). ![]() | Fig. 1. The molecular structure of the title compound. H atoms have been omitted for clarity. Primed atoms C14' and C15' are disordered with C14 and C15, respectively. |
C22H35O3P | F(000) = 412 |
Mr = 378.47 | Dx = 1.115 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 2598 reflections |
a = 10.1808 (11) Å | θ = 2.5–24.8° |
b = 11.0611 (13) Å | µ = 0.14 mm−1 |
c = 10.4207 (12) Å | T = 298 K |
β = 106.201 (1)° | Block, colorless |
V = 1126.9 (2) Å3 | 0.42 × 0.32 × 0.26 mm |
Z = 2 |
Siemens SMART CCD area-detector diffractometer | 3787 independent reflections |
Radiation source: fine-focus sealed tube | 3248 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.019 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | h = −8→12 |
Tmin = 0.944, Tmax = 0.965 | k = −13→13 |
5667 measured reflections | l = −12→10 |
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)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | w = 1/[σ2(Fo2) + (0.0437P)2 + 0.1698P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
3787 reflections | Δρmax = 0.16 e Å−3 |
263 parameters | Δρmin = −0.24 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 1685 Friedel pairs |
0 constraints | Absolute structure parameter: 0.14 (10) |
Primary atom site location: structure-invariant direct methods |
C22H35O3P | V = 1126.9 (2) Å3 |
Mr = 378.47 | Z = 2 |
Monoclinic, P21 | Mo Kα radiation |
a = 10.1808 (11) Å | µ = 0.14 mm−1 |
b = 11.0611 (13) Å | T = 298 K |
c = 10.4207 (12) Å | 0.42 × 0.32 × 0.26 mm |
β = 106.201 (1)° |
Siemens SMART CCD area-detector diffractometer | 3787 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3248 reflections with I > 2σ(I) |
Tmin = 0.944, Tmax = 0.965 | Rint = 0.019 |
5667 measured reflections |
R[F2 > 2σ(F2)] = 0.039 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.096 | Δρmax = 0.16 e Å−3 |
S = 1.06 | Δρmin = −0.24 e Å−3 |
3787 reflections | Absolute structure: Flack (1983), 1685 Friedel pairs |
263 parameters | Absolute structure parameter: 0.14 (10) |
1 restraint |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
O1 | 0.95710 (16) | 0.72151 (14) | 0.74639 (14) | 0.0404 (4) | |
O2 | 0.97738 (18) | 0.87366 (15) | 0.56708 (17) | 0.0462 (4) | |
O3 | 0.8831 (2) | 0.52789 (16) | 0.54628 (18) | 0.0454 (5) | |
H3 | 0.930 (3) | 0.488 (3) | 0.520 (3) | 0.056 (10)* | |
P1 | 0.99001 (6) | 0.74570 (6) | 0.60864 (6) | 0.03512 (16) | |
C1 | 1.1586 (3) | 0.6871 (2) | 0.6245 (2) | 0.0410 (6) | |
C2 | 1.2450 (3) | 0.7469 (3) | 0.5653 (3) | 0.0561 (7) | |
H2 | 1.2159 | 0.8181 | 0.5184 | 0.067* | |
C3 | 1.3736 (4) | 0.7031 (3) | 0.5743 (4) | 0.0805 (11) | |
H3A | 1.4317 | 0.7456 | 0.5359 | 0.097* | |
C4 | 1.4161 (3) | 0.5965 (4) | 0.6402 (4) | 0.0815 (11) | |
H4 | 1.5020 | 0.5657 | 0.6438 | 0.098* | |
C5 | 1.3327 (3) | 0.5355 (3) | 0.7005 (4) | 0.0720 (9) | |
H5 | 1.3626 | 0.4641 | 0.7465 | 0.086* | |
C6 | 1.2035 (3) | 0.5802 (3) | 0.6929 (3) | 0.0551 (7) | |
H6 | 1.1466 | 0.5386 | 0.7336 | 0.066* | |
C7 | 0.8846 (3) | 0.8021 (3) | 0.9295 (3) | 0.0561 (7) | |
H7 | 0.8856 | 0.7192 | 0.9628 | 0.067* | |
C8 | 0.9937 (3) | 0.8099 (3) | 0.8559 (2) | 0.0452 (6) | |
H8 | 0.9926 | 0.8912 | 0.8181 | 0.054* | |
C9 | 1.1352 (3) | 0.7835 (3) | 0.9449 (3) | 0.0571 (8) | |
H9A | 1.2009 | 0.7927 | 0.8937 | 0.068* | |
H9B | 1.1391 | 0.7004 | 0.9752 | 0.068* | |
C10 | 1.1745 (3) | 0.8673 (3) | 1.0659 (3) | 0.0697 (9) | |
H10 | 1.1755 | 0.9504 | 1.0336 | 0.084* | |
C11 | 1.0682 (4) | 0.8595 (4) | 1.1413 (3) | 0.0788 (10) | |
H11A | 1.0902 | 0.9170 | 1.2145 | 0.095* | |
H11B | 1.0699 | 0.7791 | 1.1791 | 0.095* | |
C12 | 0.9261 (4) | 0.8856 (4) | 1.0522 (3) | 0.0797 (11) | |
H12A | 0.9222 | 0.9689 | 1.0222 | 0.096* | |
H12B | 0.8608 | 0.8763 | 1.1037 | 0.096* | |
C13 | 0.7400 (3) | 0.8263 (4) | 0.8383 (3) | 0.0776 (11) | |
H13 | 0.7166 | 0.7564 | 0.7786 | 0.093* | |
C14 | 0.627 (3) | 0.8350 (16) | 0.911 (3) | 0.095 (5) | 0.50 |
H14A | 0.6335 | 0.9114 | 0.9559 | 0.143* | 0.50 |
H14B | 0.6381 | 0.7707 | 0.9749 | 0.143* | 0.50 |
H14C | 0.5388 | 0.8282 | 0.8467 | 0.143* | 0.50 |
C15 | 0.714 (4) | 0.938 (4) | 0.748 (3) | 0.108 (6) | 0.50 |
H15A | 0.7745 | 0.9366 | 0.6920 | 0.162* | 0.50 |
H15B | 0.7302 | 1.0094 | 0.8022 | 0.162* | 0.50 |
H15C | 0.6209 | 0.9371 | 0.6934 | 0.162* | 0.50 |
C14' | 0.635 (3) | 0.7783 (17) | 0.912 (3) | 0.095 (5) | 0.50 |
H14D | 0.6474 | 0.8216 | 0.9944 | 0.143* | 0.50 |
H14E | 0.6507 | 0.6936 | 0.9306 | 0.143* | 0.50 |
H14F | 0.5438 | 0.7903 | 0.8562 | 0.143* | 0.50 |
C15' | 0.735 (4) | 0.959 (4) | 0.789 (3) | 0.108 (6) | 0.50 |
H15D | 0.7474 | 1.0123 | 0.8642 | 0.162* | 0.50 |
H15E | 0.6473 | 0.9740 | 0.7266 | 0.162* | 0.50 |
H15R | 0.8057 | 0.9717 | 0.7467 | 0.162* | 0.50 |
C16 | 1.3180 (4) | 0.8374 (5) | 1.1542 (4) | 0.1122 (16) | |
H16A | 1.3206 | 0.7549 | 1.1833 | 0.168* | |
H16B | 1.3403 | 0.8899 | 1.2306 | 0.168* | |
H16C | 1.3831 | 0.8487 | 1.1040 | 0.168* | |
C17 | 0.8687 (2) | 0.6464 (2) | 0.4925 (2) | 0.0352 (5) | |
C18 | 0.8980 (3) | 0.6531 (2) | 0.3562 (2) | 0.0448 (6) | |
H18A | 0.8993 | 0.7372 | 0.3301 | 0.054* | |
H18B | 0.9877 | 0.6192 | 0.3638 | 0.054* | |
C19 | 0.7919 (3) | 0.5853 (3) | 0.2483 (3) | 0.0588 (8) | |
H19A | 0.8104 | 0.5973 | 0.1628 | 0.071* | |
H19B | 0.7987 | 0.4995 | 0.2681 | 0.071* | |
C20 | 0.6479 (3) | 0.6285 (3) | 0.2392 (3) | 0.0709 (9) | |
H20A | 0.6380 | 0.7123 | 0.2105 | 0.085* | |
H20B | 0.5823 | 0.5807 | 0.1733 | 0.085* | |
C21 | 0.6187 (3) | 0.6171 (3) | 0.3728 (3) | 0.0657 (9) | |
H21A | 0.6223 | 0.5326 | 0.3983 | 0.079* | |
H21B | 0.5272 | 0.6467 | 0.3654 | 0.079* | |
C22 | 0.7219 (3) | 0.6887 (3) | 0.4808 (3) | 0.0492 (7) | |
H22A | 0.7022 | 0.6777 | 0.5660 | 0.059* | |
H22B | 0.7136 | 0.7741 | 0.4590 | 0.059* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0456 (9) | 0.0393 (11) | 0.0388 (8) | −0.0032 (8) | 0.0161 (7) | −0.0047 (7) |
O2 | 0.0508 (11) | 0.0335 (10) | 0.0567 (10) | −0.0007 (8) | 0.0190 (8) | 0.0038 (8) |
O3 | 0.0580 (12) | 0.0339 (10) | 0.0494 (11) | −0.0026 (9) | 0.0233 (9) | −0.0016 (8) |
P1 | 0.0363 (3) | 0.0318 (3) | 0.0396 (3) | −0.0007 (3) | 0.0144 (2) | 0.0000 (3) |
C1 | 0.0396 (14) | 0.0410 (14) | 0.0434 (14) | 0.0005 (11) | 0.0132 (11) | −0.0020 (12) |
C2 | 0.0513 (15) | 0.0501 (15) | 0.0746 (17) | 0.0069 (17) | 0.0305 (13) | 0.0119 (19) |
C3 | 0.058 (2) | 0.078 (3) | 0.119 (3) | 0.0097 (17) | 0.048 (2) | 0.018 (2) |
C4 | 0.0510 (19) | 0.082 (3) | 0.119 (3) | 0.0225 (19) | 0.035 (2) | 0.012 (2) |
C5 | 0.059 (2) | 0.063 (2) | 0.093 (2) | 0.0203 (17) | 0.0181 (18) | 0.0197 (18) |
C6 | 0.0487 (17) | 0.0538 (18) | 0.0643 (18) | 0.0038 (14) | 0.0184 (14) | 0.0140 (15) |
C7 | 0.0615 (18) | 0.0665 (18) | 0.0429 (15) | 0.0104 (15) | 0.0191 (14) | −0.0072 (13) |
C8 | 0.0591 (17) | 0.0389 (14) | 0.0371 (14) | −0.0023 (14) | 0.0128 (13) | −0.0048 (12) |
C9 | 0.0543 (17) | 0.065 (2) | 0.0514 (16) | −0.0048 (13) | 0.0134 (13) | −0.0063 (13) |
C10 | 0.082 (2) | 0.069 (2) | 0.0504 (17) | −0.0200 (18) | 0.0051 (16) | −0.0067 (16) |
C11 | 0.094 (3) | 0.092 (3) | 0.0444 (17) | −0.004 (2) | 0.0104 (18) | −0.0162 (18) |
C12 | 0.095 (3) | 0.096 (3) | 0.0519 (18) | 0.014 (2) | 0.0266 (18) | −0.0245 (19) |
C13 | 0.062 (2) | 0.114 (3) | 0.0585 (19) | 0.029 (2) | 0.0188 (17) | −0.015 (2) |
C14 | 0.067 (7) | 0.137 (16) | 0.090 (7) | 0.030 (11) | 0.034 (5) | −0.024 (13) |
C15 | 0.099 (12) | 0.131 (17) | 0.072 (14) | 0.055 (11) | −0.012 (11) | −0.015 (12) |
C14' | 0.067 (6) | 0.137 (16) | 0.089 (7) | 0.030 (12) | 0.034 (5) | −0.024 (13) |
C15' | 0.099 (12) | 0.130 (17) | 0.072 (14) | 0.055 (11) | −0.012 (11) | −0.014 (12) |
C16 | 0.089 (3) | 0.148 (4) | 0.078 (3) | −0.027 (3) | −0.011 (2) | −0.026 (3) |
C17 | 0.0406 (14) | 0.0327 (13) | 0.0352 (12) | −0.0009 (10) | 0.0155 (11) | −0.0018 (10) |
C18 | 0.0491 (15) | 0.0478 (16) | 0.0400 (13) | 0.0045 (12) | 0.0163 (12) | 0.0001 (12) |
C19 | 0.069 (2) | 0.0644 (19) | 0.0406 (15) | 0.0064 (16) | 0.0124 (14) | −0.0084 (14) |
C20 | 0.061 (2) | 0.085 (2) | 0.0560 (18) | 0.0042 (17) | −0.0025 (15) | −0.0180 (16) |
C21 | 0.0420 (16) | 0.081 (2) | 0.070 (2) | −0.0046 (15) | 0.0094 (15) | −0.0206 (17) |
C22 | 0.0413 (15) | 0.0544 (17) | 0.0514 (15) | 0.0028 (13) | 0.0121 (12) | −0.0086 (13) |
O1—C8 | 1.469 (3) | C13—C15' | 1.55 (5) |
O1—P1 | 1.5853 (16) | C13—C14 | 1.55 (3) |
O2—P1 | 1.4752 (18) | C13—C14' | 1.57 (3) |
O3—C17 | 1.417 (3) | C13—H13 | 0.9800 |
O3—H3 | 0.76 (3) | C14—H14A | 0.9600 |
P1—C1 | 1.799 (3) | C14—H14B | 0.9600 |
P1—C17 | 1.834 (2) | C14—H14C | 0.9600 |
C1—C2 | 1.376 (4) | C15—H15A | 0.9600 |
C1—C6 | 1.390 (4) | C15—H15B | 0.9600 |
C2—C3 | 1.375 (4) | C15—H15C | 0.9600 |
C2—H2 | 0.9300 | C14'—H14D | 0.9600 |
C3—C4 | 1.371 (5) | C14'—H14E | 0.9600 |
C3—H3A | 0.9300 | C14'—H14F | 0.9600 |
C4—C5 | 1.367 (5) | C15'—H15D | 0.9600 |
C4—H4 | 0.9300 | C15'—H15E | 0.9600 |
C5—C6 | 1.387 (4) | C15'—H15R | 0.9600 |
C5—H5 | 0.9300 | C16—H16A | 0.9600 |
C6—H6 | 0.9300 | C16—H16B | 0.9600 |
C7—C8 | 1.518 (4) | C16—H16C | 0.9600 |
C7—C13 | 1.537 (4) | C17—C18 | 1.533 (3) |
C7—C12 | 1.537 (4) | C17—C22 | 1.538 (3) |
C7—H7 | 0.9800 | C18—C19 | 1.522 (4) |
C8—C9 | 1.508 (4) | C18—H18A | 0.9700 |
C8—H8 | 0.9800 | C18—H18B | 0.9700 |
C9—C10 | 1.526 (4) | C19—C20 | 1.520 (4) |
C9—H9A | 0.9700 | C19—H19A | 0.9700 |
C9—H9B | 0.9700 | C19—H19B | 0.9700 |
C10—C11 | 1.507 (5) | C20—C21 | 1.507 (4) |
C10—C16 | 1.529 (5) | C20—H20A | 0.9700 |
C10—H10 | 0.9800 | C20—H20B | 0.9700 |
C11—C12 | 1.513 (5) | C21—C22 | 1.529 (4) |
C11—H11A | 0.9700 | C21—H21A | 0.9700 |
C11—H11B | 0.9700 | C21—H21B | 0.9700 |
C12—H12A | 0.9700 | C22—H22A | 0.9700 |
C12—H12B | 0.9700 | C22—H22B | 0.9700 |
C13—C15 | 1.53 (5) | ||
C8—O1—P1 | 121.25 (15) | C7—C13—C14' | 107.6 (10) |
C17—O3—H3 | 114 (2) | C15'—C13—C14' | 121.0 (17) |
O2—P1—O1 | 113.87 (9) | C15—C13—H13 | 106.1 |
O2—P1—C1 | 112.05 (11) | C7—C13—H13 | 106.1 |
O1—P1—C1 | 107.06 (10) | C14—C13—H13 | 106.1 |
O2—P1—C17 | 113.18 (11) | C13—C14—H14A | 109.5 |
O1—P1—C17 | 102.87 (9) | C13—C14—H14B | 109.5 |
C1—P1—C17 | 107.13 (11) | C13—C14—H14C | 109.5 |
C2—C1—C6 | 118.6 (2) | C13—C15—H15A | 109.5 |
C2—C1—P1 | 119.9 (2) | C13—C15—H15B | 109.5 |
C6—C1—P1 | 121.5 (2) | C13—C15—H15C | 109.5 |
C3—C2—C1 | 121.0 (3) | C13—C14'—H14D | 109.5 |
C3—C2—H2 | 119.5 | C13—C14'—H14E | 109.5 |
C1—C2—H2 | 119.5 | H14D—C14'—H14E | 109.5 |
C4—C3—C2 | 119.9 (3) | C13—C14'—H14F | 109.5 |
C4—C3—H3A | 120.0 | H14D—C14'—H14F | 109.5 |
C2—C3—H3A | 120.0 | H14E—C14'—H14F | 109.5 |
C5—C4—C3 | 120.3 (3) | C13—C15'—H15D | 109.5 |
C5—C4—H4 | 119.8 | C13—C15'—H15E | 109.5 |
C3—C4—H4 | 119.8 | H15D—C15'—H15E | 109.5 |
C4—C5—C6 | 119.8 (3) | C13—C15'—H15R | 109.5 |
C4—C5—H5 | 120.1 | H15D—C15'—H15R | 109.5 |
C6—C5—H5 | 120.1 | H15E—C15'—H15R | 109.5 |
C5—C6—C1 | 120.2 (3) | C10—C16—H16A | 109.5 |
C5—C6—H6 | 119.9 | C10—C16—H16B | 109.5 |
C1—C6—H6 | 119.9 | H16A—C16—H16B | 109.5 |
C8—C7—C13 | 112.8 (2) | C10—C16—H16C | 109.5 |
C8—C7—C12 | 108.4 (3) | H16A—C16—H16C | 109.5 |
C13—C7—C12 | 113.8 (3) | H16B—C16—H16C | 109.5 |
C8—C7—H7 | 107.2 | O3—C17—C18 | 112.73 (19) |
C13—C7—H7 | 107.2 | O3—C17—C22 | 107.7 (2) |
C12—C7—H7 | 107.2 | C18—C17—C22 | 110.4 (2) |
O1—C8—C9 | 109.9 (2) | O3—C17—P1 | 108.49 (16) |
O1—C8—C7 | 107.0 (2) | C18—C17—P1 | 108.25 (17) |
C9—C8—C7 | 112.7 (2) | C22—C17—P1 | 109.30 (16) |
O1—C8—H8 | 109.1 | C19—C18—C17 | 112.3 (2) |
C9—C8—H8 | 109.1 | C19—C18—H18A | 109.1 |
C7—C8—H8 | 109.1 | C17—C18—H18A | 109.1 |
C8—C9—C10 | 112.1 (2) | C19—C18—H18B | 109.1 |
C8—C9—H9A | 109.2 | C17—C18—H18B | 109.1 |
C10—C9—H9A | 109.2 | H18A—C18—H18B | 107.9 |
C8—C9—H9B | 109.2 | C20—C19—C18 | 111.4 (2) |
C10—C9—H9B | 109.2 | C20—C19—H19A | 109.3 |
H9A—C9—H9B | 107.9 | C18—C19—H19A | 109.3 |
C11—C10—C9 | 109.6 (3) | C20—C19—H19B | 109.3 |
C11—C10—C16 | 112.2 (3) | C18—C19—H19B | 109.3 |
C9—C10—C16 | 110.6 (3) | H19A—C19—H19B | 108.0 |
C11—C10—H10 | 108.1 | C21—C20—C19 | 110.6 (3) |
C9—C10—H10 | 108.1 | C21—C20—H20A | 109.5 |
C16—C10—H10 | 108.1 | C19—C20—H20A | 109.5 |
C10—C11—C12 | 111.8 (3) | C21—C20—H20B | 109.5 |
C10—C11—H11A | 109.3 | C19—C20—H20B | 109.5 |
C12—C11—H11A | 109.3 | H20A—C20—H20B | 108.1 |
C10—C11—H11B | 109.3 | C20—C21—C22 | 111.4 (3) |
C12—C11—H11B | 109.3 | C20—C21—H21A | 109.3 |
H11A—C11—H11B | 107.9 | C22—C21—H21A | 109.3 |
C11—C12—C7 | 113.0 (3) | C20—C21—H21B | 109.3 |
C11—C12—H12A | 109.0 | C22—C21—H21B | 109.3 |
C7—C12—H12A | 109.0 | H21A—C21—H21B | 108.0 |
C11—C12—H12B | 109.0 | C21—C22—C17 | 110.7 (2) |
C7—C12—H12B | 109.0 | C21—C22—H22A | 109.5 |
H12A—C12—H12B | 107.8 | C17—C22—H22A | 109.5 |
C15—C13—C7 | 119.6 (14) | C21—C22—H22B | 109.5 |
C7—C13—C15' | 108.0 (13) | C17—C22—H22B | 109.5 |
C15—C13—C14 | 103.0 (17) | H22A—C22—H22B | 108.1 |
C7—C13—C14 | 115.1 (11) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.76 (3) | 1.94 (3) | 2.695 (3) | 170 (3) |
Symmetry code: (i) −x+2, y−1/2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C22H35O3P |
Mr | 378.47 |
Crystal system, space group | Monoclinic, P21 |
Temperature (K) | 298 |
a, b, c (Å) | 10.1808 (11), 11.0611 (13), 10.4207 (12) |
β (°) | 106.201 (1) |
V (Å3) | 1126.9 (2) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.14 |
Crystal size (mm) | 0.42 × 0.32 × 0.26 |
Data collection | |
Diffractometer | Siemens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.944, 0.965 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5667, 3787, 3248 |
Rint | 0.019 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.039, 0.096, 1.06 |
No. of reflections | 3787 |
No. of parameters | 263 |
No. of restraints | 1 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.16, −0.24 |
Absolute structure | Flack (1983), 1685 Friedel pairs |
Absolute structure parameter | 0.14 (10) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O3—H3···O2i | 0.76 (3) | 1.94 (3) | 2.695 (3) | 170 (3) |
Symmetry code: (i) −x+2, y−1/2, −z+1. |
Acknowledgements
We acknowledge the financial support of the Natural Science Foundation of China (No. 20772055).
References
Chaloner, P. A., Harrison, R. M. & Hitchcock, P. B. (1991). Acta Cryst. C47, 2241–2242. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
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α-Hydroxy alkylphosphonates have received attention both as substrates for the preparation of other α-substituted phosphonates, and because of their potential biological activity. For example, representatives of this class act as inhibitors of farnesyl protein transferase (FPTase), renin, and HIV protease (Kim & Wiemer, 2003).
The P-chiral title compound, which can be synthesized by addition of (RP)-menthyl-phenylphosphinate to cyclohexanone (see Experimental), is comprised of fully extended substituents: phenyl, menthyl and α-hydroxycyclohexyl. The configuration of the central P atom is R and the four groups around the P atom form an irregular tetrahedron as found in tert-butyl diphenylphosphinate (Grice et al., 2004). The bond angles are C1—P—C17 = 107.13 (11)°, O1—P—C1 = 107.06 (10)°, O1—P—C17 = 102.87 (9)°, O2—P—O1 = 113.87 (9)°, O2—P—C17 = 113.18 (11)° and O2—P—C1 = 112.05 (11)°, which compare with angles observed in related phenylphosphinate derivatives bearing a menthyl group (Chaloner et al., 1991; Sheldrick et al., 1981). Part of methyl groups (C14 and C15) were found to be disordered over two sites with equal occupancies.
Intramolecular O3—H3···O2 hydrogen bonds are found in the crystal structure. The crystal packing is further stabilized by van der Waals interactions.