



Supporting information
![]() | Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807067414/hg2360sup1.cif |
![]() | Structure factor file (CIF format) https://doi.org/10.1107/S1600536807067414/hg2360Isup2.hkl |
CCDC reference: 677526
Key indicators
- Single-crystal X-ray study
- T = 150 K
- Mean
(C-C)= 0.002 Å
- R factor = 0.030
- wR factor = 0.077
- Data-to-parameter ratio = 13.6
checkCIF/PLATON results
No syntax errors found No errors found in this datablock
Crystals of the title compound (I), were obtained by slow evaporation of equimolecular quantities of HQ (1.826 g, 0.017 mol) and TPPO (4.725 g) in 150 ml of dry acetonitrile. After three days, colourless plates of a good quality suitable for X-ray analysis were obtained. Its melting point is 425 (1) K.
All non-hydrogen atoms were identified by direct methods and the positions of all the hydrogen atoms were obtained from the use of difference Fourier maps. In the final refinement, all hydrogen atoms were constrained to geometrically sensible positions with a riding model (SHELX97), C—H= 0.95 Å, and Uiso(H)= 1.5Ueq(C), apart from H25 and H26, which were allowed to refine freely.
Data collection: CrysAlis CCD (Oxford Diffraction, 2006); cell refinement: CrysAlis RED (Oxford Diffraction, 2006); data reduction: CrysAlis RED (Oxford Diffraction, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: PARST95 (Nardelli, 1995).
C18H15OP·C6H6O2 | Z = 2 |
Mr = 388.38 | F(000) = 408 |
Triclinic, P1 | Dx = 1.284 Mg m−3 |
Hall symbol: -P 1 | Melting point: 425(1) K |
a = 8.927 (4) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.3576 (10) Å | Cell parameters from 6084 reflections |
c = 14.459 (4) Å | θ = 2.5–28.6° |
α = 71.157 (7)° | µ = 0.16 mm−1 |
β = 73.826 (6)° | T = 150 K |
γ = 62.83 (2)° | Plate, colourless |
V = 1004.6 (6) Å3 | 0.20 × 0.20 × 0.10 mm |
Oxford Diffraction Gemini diffractometer | 3560 independent reflections |
Radiation source: fine-focus sealed tube | 2837 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.025 |
Detector resolution: 15.975 pixels mm-1 | θmax = 25.0°, θmin = 2.5° |
ω and π scans | h = −10→10 |
Absorption correction: multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2006)] | k = −11→11 |
Tmin = 0.97, Tmax = 0.98 | l = −14→17 |
10150 measured reflections |
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)] = 0.030 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | w = 1/[σ2(Fo2) + (0.0364P)2 + 0.182P] where P = (Fo2 + 2Fc2)/3 |
3560 reflections | (Δ/σ)max < 0.001 |
261 parameters | Δρmax = 0.36 e Å−3 |
0 restraints | Δρmin = −0.32 e Å−3 |
C18H15OP·C6H6O2 | γ = 62.83 (2)° |
Mr = 388.38 | V = 1004.6 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.927 (4) Å | Mo Kα radiation |
b = 9.3576 (10) Å | µ = 0.16 mm−1 |
c = 14.459 (4) Å | T = 150 K |
α = 71.157 (7)° | 0.20 × 0.20 × 0.10 mm |
β = 73.826 (6)° |
Oxford Diffraction Gemini diffractometer | 3560 independent reflections |
Absorption correction: multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2006)] | 2837 reflections with I > 2σ(I) |
Tmin = 0.97, Tmax = 0.98 | Rint = 0.025 |
10150 measured reflections |
R[F2 > 2σ(F2)] = 0.030 | 0 restraints |
wR(F2) = 0.077 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.11 | Δρmax = 0.36 e Å−3 |
3560 reflections | Δρmin = −0.32 e Å−3 |
261 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
P1 | 0.95138 (5) | 0.39823 (5) | 0.27946 (3) | 0.01905 (11) | |
O1 | 1.12889 (12) | 0.37744 (12) | 0.27829 (7) | 0.0236 (2) | |
O2 | 0.31558 (16) | 0.56334 (14) | 0.18170 (8) | 0.0330 (3) | |
O3 | 0.43737 (16) | 0.13741 (16) | 0.30698 (8) | 0.0390 (3) | |
C19 | 0.40534 (19) | 0.52905 (18) | 0.09190 (10) | 0.0225 (3) | |
C13 | 0.95218 (18) | 0.23915 (17) | 0.23485 (10) | 0.0198 (3) | |
C18 | 1.0897 (2) | 0.08595 (18) | 0.24493 (11) | 0.0265 (4) | |
H18 | 1.1811 | 0.0670 | 0.2750 | 0.040* | |
C24 | 0.3343 (2) | 0.09996 (18) | 0.48323 (11) | 0.0269 (4) | |
H24 | 0.2203 | 0.1685 | 0.4719 | 0.040* | |
C21 | 0.59840 (19) | 0.58783 (18) | −0.05380 (11) | 0.0240 (3) | |
H21 | 0.6654 | 0.6487 | −0.0905 | 0.036* | |
C10 | 0.6658 (2) | 0.37566 (19) | 0.59682 (11) | 0.0277 (4) | |
H10 | 0.6091 | 0.3701 | 0.6632 | 0.042* | |
C14 | 0.81782 (19) | 0.26512 (19) | 0.19154 (11) | 0.0254 (3) | |
H14 | 0.7230 | 0.3688 | 0.1848 | 0.038* | |
C1 | 0.84087 (18) | 0.59192 (17) | 0.19937 (10) | 0.0195 (3) | |
C8 | 0.7437 (2) | 0.29020 (19) | 0.44432 (11) | 0.0274 (4) | |
H8 | 0.7401 | 0.2258 | 0.4065 | 0.041* | |
C7 | 0.83224 (18) | 0.39133 (17) | 0.40226 (10) | 0.0200 (3) | |
C6 | 0.9123 (2) | 0.61763 (18) | 0.09972 (11) | 0.0250 (3) | |
H6 | 1.0129 | 0.5328 | 0.0765 | 0.037* | |
C3 | 0.6205 (2) | 0.86657 (19) | 0.16682 (12) | 0.0303 (4) | |
H3 | 0.5207 | 0.9524 | 0.1897 | 0.046* | |
C20 | 0.50465 (19) | 0.61583 (18) | 0.03765 (11) | 0.0237 (3) | |
H20 | 0.5086 | 0.6953 | 0.0633 | 0.035* | |
C9 | 0.6605 (2) | 0.2829 (2) | 0.54123 (11) | 0.0310 (4) | |
H9 | 0.5998 | 0.2140 | 0.5695 | 0.047* | |
C16 | 0.9609 (2) | −0.01175 (19) | 0.16781 (12) | 0.0306 (4) | |
H16 | 0.9642 | −0.0972 | 0.1443 | 0.046* | |
C5 | 0.8378 (2) | 0.76576 (19) | 0.03425 (11) | 0.0281 (4) | |
H5 | 0.8866 | 0.7821 | −0.0336 | 0.042* | |
C12 | 0.8361 (2) | 0.48507 (19) | 0.45913 (11) | 0.0273 (4) | |
H12 | 0.8958 | 0.5550 | 0.4312 | 0.041* | |
C15 | 0.8228 (2) | 0.1395 (2) | 0.15826 (12) | 0.0308 (4) | |
H15 | 0.7311 | 0.1572 | 0.1288 | 0.046* | |
C17 | 1.0939 (2) | −0.03884 (19) | 0.21136 (12) | 0.0310 (4) | |
H17 | 1.1881 | −0.1430 | 0.2183 | 0.046* | |
C22 | 0.6308 (2) | −0.02875 (18) | 0.42058 (11) | 0.0262 (4) | |
H22 | 0.7207 | −0.0489 | 0.3663 | 0.039* | |
C2 | 0.69447 (19) | 0.71779 (18) | 0.23265 (11) | 0.0247 (3) | |
H2 | 0.6450 | 0.7021 | 0.3004 | 0.037* | |
C23 | 0.4649 (2) | 0.07154 (18) | 0.40370 (11) | 0.0258 (4) | |
C11 | 0.7535 (2) | 0.4765 (2) | 0.55590 (11) | 0.0306 (4) | |
H11 | 0.7570 | 0.5401 | 0.5943 | 0.046* | |
C4 | 0.6920 (2) | 0.88961 (19) | 0.06822 (12) | 0.0284 (4) | |
H4 | 0.6407 | 0.9912 | 0.0234 | 0.043* | |
H25 | 0.251 (3) | 0.509 (3) | 0.2108 (15) | 0.059 (6)* | |
H26 | 0.332 (3) | 0.209 (3) | 0.3043 (14) | 0.055 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0199 (2) | 0.0200 (2) | 0.0180 (2) | −0.00858 (16) | −0.00232 (15) | −0.00511 (15) |
O1 | 0.0217 (6) | 0.0269 (6) | 0.0236 (6) | −0.0118 (5) | −0.0035 (4) | −0.0044 (4) |
O2 | 0.0419 (7) | 0.0360 (7) | 0.0268 (6) | −0.0243 (6) | 0.0089 (5) | −0.0137 (5) |
O3 | 0.0303 (7) | 0.0430 (7) | 0.0287 (7) | −0.0009 (6) | −0.0079 (5) | −0.0079 (5) |
C19 | 0.0222 (8) | 0.0216 (7) | 0.0213 (8) | −0.0071 (7) | −0.0030 (6) | −0.0050 (6) |
C13 | 0.0221 (8) | 0.0213 (7) | 0.0157 (7) | −0.0094 (6) | −0.0019 (6) | −0.0036 (6) |
C18 | 0.0281 (9) | 0.0236 (8) | 0.0263 (8) | −0.0063 (7) | −0.0097 (7) | −0.0056 (6) |
C24 | 0.0214 (8) | 0.0224 (8) | 0.0357 (9) | −0.0062 (7) | −0.0060 (7) | −0.0077 (7) |
C21 | 0.0226 (8) | 0.0233 (8) | 0.0275 (9) | −0.0122 (7) | −0.0038 (7) | −0.0035 (6) |
C10 | 0.0300 (9) | 0.0298 (9) | 0.0183 (8) | −0.0113 (7) | 0.0001 (7) | −0.0036 (7) |
C14 | 0.0242 (9) | 0.0232 (8) | 0.0288 (9) | −0.0076 (7) | −0.0063 (7) | −0.0071 (6) |
C1 | 0.0211 (8) | 0.0205 (7) | 0.0210 (8) | −0.0111 (6) | −0.0025 (6) | −0.0064 (6) |
C8 | 0.0330 (9) | 0.0284 (8) | 0.0258 (9) | −0.0170 (7) | 0.0010 (7) | −0.0103 (7) |
C7 | 0.0203 (8) | 0.0191 (7) | 0.0199 (8) | −0.0075 (6) | −0.0044 (6) | −0.0032 (6) |
C6 | 0.0261 (9) | 0.0241 (8) | 0.0237 (8) | −0.0086 (7) | −0.0023 (7) | −0.0077 (6) |
C3 | 0.0247 (9) | 0.0232 (8) | 0.0414 (10) | −0.0052 (7) | −0.0054 (7) | −0.0119 (7) |
C20 | 0.0259 (8) | 0.0205 (7) | 0.0268 (8) | −0.0099 (7) | −0.0053 (7) | −0.0062 (6) |
C9 | 0.0366 (10) | 0.0299 (9) | 0.0288 (9) | −0.0211 (8) | 0.0051 (7) | −0.0066 (7) |
C16 | 0.0424 (10) | 0.0259 (9) | 0.0303 (9) | −0.0175 (8) | −0.0048 (8) | −0.0099 (7) |
C5 | 0.0356 (10) | 0.0302 (9) | 0.0209 (8) | −0.0169 (8) | −0.0047 (7) | −0.0032 (7) |
C12 | 0.0335 (9) | 0.0325 (9) | 0.0238 (8) | −0.0206 (8) | −0.0017 (7) | −0.0075 (7) |
C15 | 0.0324 (9) | 0.0339 (9) | 0.0339 (9) | −0.0162 (8) | −0.0090 (7) | −0.0099 (7) |
C17 | 0.0349 (10) | 0.0202 (8) | 0.0325 (9) | −0.0047 (7) | −0.0080 (8) | −0.0066 (7) |
C22 | 0.0235 (8) | 0.0236 (8) | 0.0297 (9) | −0.0089 (7) | 0.0003 (7) | −0.0084 (7) |
C2 | 0.0220 (8) | 0.0256 (8) | 0.0260 (8) | −0.0095 (7) | −0.0001 (7) | −0.0086 (7) |
C23 | 0.0281 (9) | 0.0205 (8) | 0.0288 (9) | −0.0088 (7) | −0.0064 (7) | −0.0055 (6) |
C11 | 0.0384 (10) | 0.0366 (9) | 0.0242 (9) | −0.0194 (8) | −0.0024 (7) | −0.0118 (7) |
C4 | 0.0323 (9) | 0.0207 (8) | 0.0350 (10) | −0.0111 (7) | −0.0154 (8) | −0.0007 (7) |
P1—O1 | 1.5016 (13) | C8—C9 | 1.387 (2) |
P1—C7 | 1.7957 (15) | C8—C7 | 1.391 (2) |
P1—C13 | 1.8000 (14) | C8—H8 | 0.9500 |
P1—C1 | 1.8020 (15) | C7—C12 | 1.399 (2) |
O2—C19 | 1.3732 (18) | C6—C5 | 1.386 (2) |
O2—H25 | 0.87 (2) | C6—H6 | 0.9500 |
O3—C23 | 1.3756 (19) | C3—C4 | 1.381 (2) |
O3—H26 | 0.87 (2) | C3—C2 | 1.391 (2) |
C19—C20 | 1.385 (2) | C3—H3 | 0.9500 |
C19—C21i | 1.391 (2) | C20—H20 | 0.9500 |
C13—C18 | 1.393 (2) | C9—H9 | 0.9500 |
C13—C14 | 1.394 (2) | C16—C17 | 1.382 (2) |
C18—C17 | 1.384 (2) | C16—C15 | 1.384 (2) |
C18—H18 | 0.9500 | C16—H16 | 0.9500 |
C24—C23 | 1.386 (2) | C5—C4 | 1.383 (2) |
C24—C22ii | 1.389 (2) | C5—H5 | 0.9500 |
C24—H24 | 0.9500 | C12—C11 | 1.384 (2) |
C21—C20 | 1.387 (2) | C12—H12 | 0.9500 |
C21—C19i | 1.391 (2) | C15—H15 | 0.9500 |
C21—H21 | 0.9500 | C17—H17 | 0.9500 |
C10—C11 | 1.382 (2) | C22—C23 | 1.384 (2) |
C10—C9 | 1.382 (2) | C22—C24ii | 1.389 (2) |
C10—H10 | 0.9500 | C22—H22 | 0.9500 |
C14—C15 | 1.386 (2) | C2—H2 | 0.9500 |
C14—H14 | 0.9500 | C11—H11 | 0.9500 |
C1—C2 | 1.392 (2) | C4—H4 | 0.9500 |
C1—C6 | 1.395 (2) | ||
O1—P1—C7 | 111.26 (6) | C1—C6—H6 | 119.7 |
O1—P1—C13 | 111.76 (7) | C4—C3—C2 | 120.06 (15) |
C7—P1—C13 | 107.64 (7) | C4—C3—H3 | 120.0 |
O1—P1—C1 | 110.35 (7) | C2—C3—H3 | 120.0 |
C7—P1—C1 | 109.06 (7) | C19—C20—C21 | 120.68 (14) |
C13—P1—C1 | 106.61 (7) | C19—C20—H20 | 119.7 |
C19—O2—H25 | 113.3 (14) | C21—C20—H20 | 119.7 |
C23—O3—H26 | 110.4 (13) | C10—C9—C8 | 120.17 (15) |
O2—C19—C20 | 117.57 (13) | C10—C9—H9 | 119.9 |
O2—C19—C21i | 123.33 (14) | C8—C9—H9 | 119.9 |
C20—C19—C21i | 119.10 (14) | C17—C16—C15 | 120.20 (14) |
C18—C13—C14 | 119.35 (14) | C17—C16—H16 | 119.9 |
C18—C13—P1 | 119.06 (11) | C15—C16—H16 | 119.9 |
C14—C13—P1 | 121.58 (11) | C4—C5—C6 | 119.69 (15) |
C17—C18—C13 | 120.39 (15) | C4—C5—H5 | 120.2 |
C17—C18—H18 | 119.8 | C6—C5—H5 | 120.2 |
C13—C18—H18 | 119.8 | C11—C12—C7 | 120.35 (14) |
C23—C24—C22ii | 120.31 (15) | C11—C12—H12 | 119.8 |
C23—C24—H24 | 119.8 | C7—C12—H12 | 119.8 |
C22ii—C24—H24 | 119.8 | C16—C15—C14 | 120.20 (15) |
C20—C21—C19i | 120.21 (14) | C16—C15—H15 | 119.9 |
C20—C21—H21 | 119.9 | C14—C15—H15 | 119.9 |
C19i—C21—H21 | 119.9 | C16—C17—C18 | 119.93 (15) |
C11—C10—C9 | 120.09 (14) | C16—C17—H17 | 120.0 |
C11—C10—H10 | 120.0 | C18—C17—H17 | 120.0 |
C9—C10—H10 | 120.0 | C23—C22—C24ii | 120.06 (14) |
C15—C14—C13 | 119.93 (14) | C23—C22—H22 | 120.0 |
C15—C14—H14 | 120.0 | C24ii—C22—H22 | 120.0 |
C13—C14—H14 | 120.0 | C3—C2—C1 | 120.11 (14) |
C2—C1—C6 | 119.13 (14) | C3—C2—H2 | 119.9 |
C2—C1—P1 | 123.52 (11) | C1—C2—H2 | 119.9 |
C6—C1—P1 | 117.28 (11) | O3—C23—C22 | 117.62 (14) |
C9—C8—C7 | 120.29 (14) | O3—C23—C24 | 122.74 (14) |
C9—C8—H8 | 119.9 | C22—C23—C24 | 119.63 (14) |
C7—C8—H8 | 119.9 | C10—C11—C12 | 120.10 (14) |
C8—C7—C12 | 119.00 (14) | C10—C11—H11 | 120.0 |
C8—C7—P1 | 122.40 (11) | C12—C11—H11 | 120.0 |
C12—C7—P1 | 118.52 (11) | C3—C4—C5 | 120.41 (14) |
C5—C6—C1 | 120.60 (14) | C3—C4—H4 | 119.8 |
C5—C6—H6 | 119.7 | C5—C4—H4 | 119.8 |
O1—P1—C13—C18 | 27.30 (14) | P1—C1—C6—C5 | −177.79 (12) |
C7—P1—C13—C18 | −95.15 (13) | O2—C19—C20—C21 | −179.84 (13) |
C1—P1—C13—C18 | 147.95 (12) | C21i—C19—C20—C21 | 0.5 (2) |
O1—P1—C13—C14 | −153.41 (12) | C19i—C21—C20—C19 | −0.5 (2) |
C7—P1—C13—C14 | 84.14 (13) | C11—C10—C9—C8 | 0.2 (2) |
C1—P1—C13—C14 | −32.76 (14) | C7—C8—C9—C10 | −0.3 (2) |
C14—C13—C18—C17 | 0.7 (2) | C1—C6—C5—C4 | 0.5 (2) |
P1—C13—C18—C17 | 179.98 (12) | C8—C7—C12—C11 | 0.3 (2) |
C18—C13—C14—C15 | −0.6 (2) | P1—C7—C12—C11 | −176.59 (12) |
P1—C13—C14—C15 | −179.84 (12) | C17—C16—C15—C14 | 0.6 (2) |
O1—P1—C1—C2 | −117.60 (13) | C13—C14—C15—C16 | −0.1 (2) |
C7—P1—C1—C2 | 4.90 (15) | C15—C16—C17—C18 | −0.5 (2) |
C13—P1—C1—C2 | 120.85 (13) | C13—C18—C17—C16 | −0.2 (2) |
O1—P1—C1—C6 | 59.36 (13) | C4—C3—C2—C1 | 0.1 (2) |
C7—P1—C1—C6 | −178.14 (11) | C6—C1—C2—C3 | 0.4 (2) |
C13—P1—C1—C6 | −62.18 (13) | P1—C1—C2—C3 | 177.30 (11) |
C9—C8—C7—C12 | 0.0 (2) | C24ii—C22—C23—O3 | −179.31 (14) |
C9—C8—C7—P1 | 176.74 (12) | C24ii—C22—C23—C24 | −0.2 (2) |
O1—P1—C7—C8 | −129.66 (13) | C22ii—C24—C23—O3 | 179.27 (14) |
C13—P1—C7—C8 | −6.90 (15) | C22ii—C24—C23—C22 | 0.2 (2) |
C1—P1—C7—C8 | 108.39 (13) | C9—C10—C11—C12 | 0.0 (2) |
O1—P1—C7—C12 | 47.07 (13) | C7—C12—C11—C10 | −0.3 (2) |
C13—P1—C7—C12 | 169.82 (12) | C2—C3—C4—C5 | −0.4 (2) |
C1—P1—C7—C12 | −74.88 (13) | C6—C5—C4—C3 | 0.1 (2) |
C2—C1—C6—C5 | −0.7 (2) |
Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y, −z+1. |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H25···O1iii | 0.87 (2) | 1.87 (2) | 2.7451 (17) | 175 (2) |
O3—H26···O1iii | 0.87 (2) | 1.82 (2) | 2.681 (2) | 170 (2) |
C3—H3···O3iv | 0.95 | 2.54 | 3.300 (2) | 137 |
Symmetry codes: (iii) x−1, y, z; (iv) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C18H15OP·C6H6O2 |
Mr | 388.38 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 150 |
a, b, c (Å) | 8.927 (4), 9.3576 (10), 14.459 (4) |
α, β, γ (°) | 71.157 (7), 73.826 (6), 62.83 (2) |
V (Å3) | 1004.6 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.16 |
Crystal size (mm) | 0.20 × 0.20 × 0.10 |
Data collection | |
Diffractometer | Oxford Diffraction Gemini diffractometer |
Absorption correction | Multi-scan [empirical (using intensity measurements) absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm (Oxford Diffraction, 2006)] |
Tmin, Tmax | 0.97, 0.98 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10150, 3560, 2837 |
Rint | 0.025 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.030, 0.077, 1.11 |
No. of reflections | 3560 |
No. of parameters | 261 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.36, −0.32 |
Computer programs: CrysAlis CCD (Oxford Diffraction, 2006), CrysAlis RED (Oxford Diffraction, 2006), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), ORTEP-3 for Windows (Farrugia, 1997), PARST95 (Nardelli, 1995).
P1—O1 | 1.5016 (13) | P1—C1 | 1.8020 (15) |
P1—C7 | 1.7957 (15) | O2—C19 | 1.3732 (18) |
P1—C13 | 1.8000 (14) | O3—C23 | 1.3756 (19) |
O1—P1—C7 | 111.26 (6) | O1—P1—C1 | 110.35 (7) |
O1—P1—C13 | 111.76 (7) | ||
O1—P1—C13—C14 | −153.41 (12) | O1—P1—C7—C8 | −129.66 (13) |
O1—P1—C1—C2 | −117.60 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H25···O1i | 0.87 (2) | 1.87 (2) | 2.7451 (17) | 175 (2) |
O3—H26···O1i | 0.87 (2) | 1.82 (2) | 2.681 (2) | 170 (2) |
C3—H3···O3ii | 0.95 | 2.54 | 3.300 (2) | 137.3 |
Symmetry codes: (i) x−1, y, z; (ii) x, y+1, z. |
The title compound, C18H15OP.C6H6O2, belongs to a series of molecular systems based on triphenylphosphine P-oxide (TPPO) with diverse hydrogen-bond donors (Fuquen et al., 1992). In order to expand the crystallographic information of the TPPO complexes, to study the hydrogen bond character of the complex, and to analize its supramolecular arrangement, the structure determination of TPPO + hydroquinone (HQ), (I), system was undertaken. The free HQ molecule in the more stable form at room temperature (Wallwork & Powell, 1980) and the free TPPO molecule (Al-Farhan, 1992) can be taken as a reference systems to compare with the structural characteristics of (I). A displacement ellipsoid plot of the title hydrogen-bonded complex (I), showing the atomic numbering scheme is given in Fig. 1. The O1 atom of the P-oxide group of TPPO acts as an acceptor for hydrogen bonds from O—H groups of two hydroquinone molecules [O1···O2, 2.7451 (17), O1···O3, 2.681 (2) Å and O1···H25—O2, O1···H26—O3 angles of 175 (2) and 170 (2)° respectively, (Table 2)]. These two HQ molecules are each disposed about a centre of symmetry. The title molecule shows a H25—O1—H26 bond angle close to the right angle, seeking an orientation with the minor repulsion between the rings of the molecule. The presence of the three centre hydrogen bond at O1 induces the lengthening of P—O bond length from 1.479 (2) Å in free TPPO molecule (Al-Farhan, 1992) to 1.5016 (13) Å in (I). Other bond lengths and angles of TPPO and HQ remain similar in the complex. The title molecules of (I) are additionally linked by C—H···O hydrogen bonds. Indeed, atom C3 in the molecule at (x, y, z) acts as a hydrogen-bond donor to O3iv atom in the molecule at (x, 1 + y, z), so generating a C21(8) chain (Etter, 1990) which is running parallel to [100] direction (Fig. 2, Supp.material). Other significant intermolecular hydrogen bonds are not observed in the crystalline structure.