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In the title compound, C
18H
15OP·C
11H
8O
2, co-crystallization of triphenylphosphine oxide with 1-naphthoic acid yields a supramolecular structure held together by one O-H
O and three C-H
O hydrogen bonds. The O-H
O hydrogen bond [O
O = 2.592 (2) Å] has little effect on the O=P bond distance.
Supporting information
CCDC reference: 245930
The title compound was prepared by mixing equimolar amounts of TPPO and 1-naphthoic acid in CCl4. Slow evaporation of the solvent afforded colourless crystals suitable for X-ray analysis.
H atoms bonded to C atoms were placed geometrically (C—H = 0.96 Å) and allowed to ride during structure refinement, with isotropic displacement parameters fixed at 1.2Ueq of the parent atoms. The H atom of the carboxyl group was located in a difference Fourier map and was allowed to refine freely.
Data collection: XSCANS (Siemens, 1995); cell refinement: XSCANS; data reduction: XSCANS; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1995); software used to prepare material for publication: SHELXL97.
Triphenylphosphine oxide–1-naphthoic acid (1/1)
top
Crystal data top
C18H15OP·C11H8O2 | F(000) = 944 |
Mr = 450.44 | Dx = 1.270 Mg m−3 |
Monoclinic, P21/n | Melting point: 353 K |
Hall symbol: -P 2yn | Mo Kα radiation, λ = 0.71073 Å |
a = 8.963 (1) Å | Cell parameters from 25 reflections |
b = 16.303 (1) Å | θ = 17.2–17.9° |
c = 16.673 (1) Å | µ = 0.15 mm−1 |
β = 104.784 (7)° | T = 296 K |
V = 2355.7 (3) Å3 | Plate, colourless |
Z = 4 | 0.30 × 0.28 × 0.12 mm |
Data collection top
Siemens P4 diffractometer | Rint = 0.021 |
Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 1.8° |
Graphite monochromator | h = −3→10 |
θ–2θ scans | k = −8→19 |
5488 measured reflections | l = −19→19 |
4083 independent reflections | 3 standard reflections every 200 reflections |
2933 reflections with I > 2σ(I) | intensity decay: none |
Refinement top
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.0476P)2 + 0.545P] where P = (Fo2 + 2Fc2)/3 |
4083 reflections | (Δ/σ)max = 0.001 |
302 parameters | Δρmax = 0.21 e Å−3 |
0 restraints | Δρmin = −0.22 e Å−3 |
Crystal data top
C18H15OP·C11H8O2 | V = 2355.7 (3) Å3 |
Mr = 450.44 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.963 (1) Å | µ = 0.15 mm−1 |
b = 16.303 (1) Å | T = 296 K |
c = 16.673 (1) Å | 0.30 × 0.28 × 0.12 mm |
β = 104.784 (7)° | |
Data collection top
Siemens P4 diffractometer | Rint = 0.021 |
5488 measured reflections | 3 standard reflections every 200 reflections |
4083 independent reflections | intensity decay: none |
2933 reflections with I > 2σ(I) | |
Refinement top
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.111 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | Δρmax = 0.21 e Å−3 |
4083 reflections | Δρmin = −0.22 e Å−3 |
302 parameters | |
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. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top | x | y | z | Uiso*/Ueq | |
P1 | 0.33131 (7) | 0.89507 (3) | 0.64862 (3) | 0.05938 (17) | |
O1 | 0.3885 (2) | 0.86498 (9) | 0.57765 (10) | 0.0822 (5) | |
C1 | 0.3848 (2) | 0.82843 (12) | 0.73735 (13) | 0.0605 (5) | |
C2 | 0.3139 (3) | 0.83248 (14) | 0.80250 (15) | 0.0745 (6) | |
H2 | 0.2326 | 0.8714 | 0.8003 | 0.089* | |
C3 | 0.3593 (3) | 0.78113 (15) | 0.87018 (16) | 0.0872 (7) | |
H3 | 0.3102 | 0.7848 | 0.9149 | 0.105* | |
C4 | 0.4743 (3) | 0.72499 (16) | 0.87352 (18) | 0.0904 (8) | |
H4 | 0.5061 | 0.6894 | 0.9206 | 0.109* | |
C5 | 0.5443 (3) | 0.71973 (15) | 0.80935 (18) | 0.0891 (8) | |
H5 | 0.6244 | 0.6800 | 0.8118 | 0.107* | |
C6 | 0.5006 (3) | 0.77131 (13) | 0.74101 (15) | 0.0740 (6) | |
H6 | 0.5504 | 0.7674 | 0.6966 | 0.089* | |
C7 | 0.4076 (2) | 0.99553 (12) | 0.67865 (12) | 0.0562 (5) | |
C8 | 0.4058 (3) | 1.03138 (14) | 0.75291 (16) | 0.0862 (8) | |
H8 | 0.3607 | 1.0027 | 0.7912 | 0.103* | |
C9 | 0.4686 (4) | 1.10855 (16) | 0.77296 (19) | 0.1023 (9) | |
H9 | 0.4686 | 1.1326 | 0.8255 | 0.123* | |
C10 | 0.5298 (3) | 1.15025 (16) | 0.7190 (2) | 0.0982 (9) | |
H10 | 0.5697 | 1.2046 | 0.7323 | 0.118* | |
C11 | 0.5350 (4) | 1.11519 (18) | 0.6459 (2) | 0.1011 (9) | |
H11 | 0.5812 | 1.1442 | 0.6083 | 0.121* | |
C12 | 0.4740 (3) | 1.03797 (15) | 0.62551 (15) | 0.0783 (7) | |
H12 | 0.4781 | 1.0137 | 0.5737 | 0.094* | |
C13 | 0.1248 (2) | 0.90161 (14) | 0.62433 (12) | 0.0626 (5) | |
C14 | 0.0439 (3) | 0.97432 (16) | 0.60884 (14) | 0.0748 (6) | |
H14 | 0.0983 | 1.0256 | 0.6146 | 0.090* | |
C15 | −0.1159 (3) | 0.9735 (2) | 0.58502 (17) | 0.0959 (8) | |
H15 | −0.1721 | 1.0241 | 0.5737 | 0.115* | |
C16 | −0.1943 (3) | 0.9001 (3) | 0.57749 (16) | 0.1057 (10) | |
H16 | −0.3050 | 0.8995 | 0.5610 | 0.127* | |
C17 | −0.1149 (4) | 0.8284 (2) | 0.59346 (19) | 0.1112 (10) | |
H17 | −0.1699 | 0.7773 | 0.5888 | 0.133* | |
C18 | 0.0428 (3) | 0.82848 (17) | 0.61611 (17) | 0.0937 (8) | |
H18 | 0.0975 | 0.7774 | 0.6265 | 0.112* | |
O2 | 0.3853 (2) | 0.73940 (11) | 0.48186 (11) | 0.0885 (5) | |
H1 | 0.398 (4) | 0.786 (2) | 0.522 (2) | 0.153 (13)* | |
O3 | 0.6091 (2) | 0.69781 (12) | 0.56096 (14) | 0.1119 (7) | |
C19 | 0.5054 (3) | 0.68998 (14) | 0.49871 (16) | 0.0722 (6) | |
C20 | 0.4975 (3) | 0.62408 (13) | 0.43539 (14) | 0.0681 (6) | |
C21 | 0.3790 (3) | 0.62752 (16) | 0.36478 (15) | 0.0845 (7) | |
H21 | 0.3072 | 0.6723 | 0.3574 | 0.101* | |
C22 | 0.3603 (4) | 0.5673 (2) | 0.30327 (16) | 0.1011 (9) | |
H22 | 0.2774 | 0.5714 | 0.2539 | 0.121* | |
C23 | 0.4593 (4) | 0.50337 (19) | 0.31352 (17) | 0.0962 (9) | |
H23 | 0.4451 | 0.4620 | 0.2713 | 0.115* | |
C24 | 0.5825 (3) | 0.49611 (14) | 0.38462 (15) | 0.0757 (7) | |
C25 | 0.6837 (4) | 0.42814 (17) | 0.3952 (2) | 0.0941 (9) | |
H25 | 0.6675 | 0.3866 | 0.3530 | 0.113* | |
C26 | 0.8024 (4) | 0.42052 (19) | 0.4632 (2) | 0.1019 (9) | |
H26 | 0.8703 | 0.3741 | 0.4692 | 0.122* | |
C27 | 0.8258 (4) | 0.4807 (2) | 0.5249 (2) | 0.0990 (8) | |
H27 | 0.9104 | 0.4752 | 0.5733 | 0.119* | |
C28 | 0.7303 (3) | 0.54723 (16) | 0.51765 (17) | 0.0819 (7) | |
H28 | 0.7489 | 0.5876 | 0.5610 | 0.098* | |
C29 | 0.6048 (3) | 0.55750 (14) | 0.44734 (14) | 0.0678 (6) | |
Atomic displacement parameters (Å2) top | U11 | U22 | U33 | U12 | U13 | U23 |
P1 | 0.0665 (3) | 0.0520 (3) | 0.0647 (3) | −0.0007 (3) | 0.0259 (3) | −0.0049 (3) |
O1 | 0.1055 (13) | 0.0719 (10) | 0.0834 (10) | 0.0000 (9) | 0.0499 (9) | −0.0135 (8) |
C1 | 0.0607 (12) | 0.0467 (10) | 0.0744 (13) | −0.0012 (9) | 0.0178 (10) | −0.0031 (9) |
C2 | 0.0821 (15) | 0.0625 (13) | 0.0854 (15) | 0.0108 (12) | 0.0332 (13) | 0.0118 (12) |
C3 | 0.107 (2) | 0.0750 (16) | 0.0835 (16) | 0.0081 (15) | 0.0323 (15) | 0.0136 (13) |
C4 | 0.108 (2) | 0.0671 (15) | 0.0865 (18) | 0.0047 (15) | 0.0069 (16) | 0.0094 (13) |
C5 | 0.0827 (18) | 0.0640 (15) | 0.110 (2) | 0.0200 (13) | 0.0044 (16) | −0.0016 (15) |
C6 | 0.0696 (14) | 0.0626 (13) | 0.0889 (16) | 0.0054 (12) | 0.0185 (12) | −0.0092 (12) |
C7 | 0.0548 (11) | 0.0536 (11) | 0.0638 (12) | 0.0025 (9) | 0.0216 (9) | 0.0028 (9) |
C8 | 0.120 (2) | 0.0642 (14) | 0.0904 (17) | −0.0264 (14) | 0.0572 (16) | −0.0126 (13) |
C9 | 0.139 (3) | 0.0724 (16) | 0.108 (2) | −0.0297 (17) | 0.0553 (19) | −0.0240 (15) |
C10 | 0.108 (2) | 0.0644 (15) | 0.126 (2) | −0.0254 (15) | 0.0371 (19) | −0.0011 (16) |
C11 | 0.117 (2) | 0.0866 (19) | 0.107 (2) | −0.0305 (17) | 0.0419 (18) | 0.0209 (17) |
C12 | 0.0894 (17) | 0.0788 (16) | 0.0710 (14) | −0.0112 (13) | 0.0285 (13) | 0.0080 (12) |
C13 | 0.0643 (12) | 0.0684 (13) | 0.0542 (11) | −0.0065 (11) | 0.0134 (9) | −0.0010 (10) |
C14 | 0.0682 (15) | 0.0799 (16) | 0.0767 (15) | 0.0024 (12) | 0.0191 (12) | 0.0110 (12) |
C15 | 0.0691 (17) | 0.125 (2) | 0.0898 (18) | 0.0177 (17) | 0.0133 (14) | 0.0225 (17) |
C16 | 0.0651 (16) | 0.171 (3) | 0.0726 (16) | −0.021 (2) | 0.0022 (13) | 0.010 (2) |
C17 | 0.089 (2) | 0.123 (3) | 0.107 (2) | −0.044 (2) | −0.0015 (18) | −0.001 (2) |
C18 | 0.0843 (19) | 0.0784 (16) | 0.108 (2) | −0.0220 (15) | 0.0057 (16) | −0.0053 (15) |
O2 | 0.1228 (15) | 0.0644 (10) | 0.0789 (11) | 0.0064 (11) | 0.0268 (10) | −0.0061 (9) |
O3 | 0.0828 (12) | 0.1111 (15) | 0.1352 (16) | −0.0169 (11) | 0.0156 (12) | −0.0631 (13) |
C19 | 0.0793 (16) | 0.0651 (14) | 0.0801 (15) | −0.0293 (13) | 0.0348 (13) | −0.0139 (12) |
C20 | 0.0880 (16) | 0.0591 (13) | 0.0681 (13) | −0.0210 (12) | 0.0397 (12) | −0.0070 (10) |
C21 | 0.108 (2) | 0.0791 (16) | 0.0693 (15) | −0.0089 (15) | 0.0279 (14) | −0.0054 (12) |
C22 | 0.130 (3) | 0.106 (2) | 0.0661 (16) | −0.019 (2) | 0.0214 (16) | −0.0152 (15) |
C23 | 0.134 (3) | 0.0879 (19) | 0.0771 (17) | −0.0266 (19) | 0.0465 (18) | −0.0269 (15) |
C24 | 0.0996 (18) | 0.0657 (14) | 0.0784 (16) | −0.0253 (13) | 0.0530 (15) | −0.0124 (12) |
C25 | 0.119 (2) | 0.0724 (17) | 0.116 (2) | −0.0190 (17) | 0.076 (2) | −0.0144 (16) |
C26 | 0.105 (2) | 0.088 (2) | 0.132 (3) | −0.0034 (18) | 0.065 (2) | 0.001 (2) |
C27 | 0.0868 (19) | 0.102 (2) | 0.115 (2) | −0.0078 (17) | 0.0395 (17) | 0.0030 (19) |
C28 | 0.0818 (17) | 0.0800 (17) | 0.0932 (18) | −0.0213 (14) | 0.0390 (15) | −0.0105 (14) |
C29 | 0.0798 (15) | 0.0649 (13) | 0.0714 (14) | −0.0269 (12) | 0.0427 (12) | −0.0060 (11) |
Geometric parameters (Å, º) top
P1—O1 | 1.4880 (15) | C15—C16 | 1.377 (4) |
P1—C1 | 1.799 (2) | C15—H15 | 0.9600 |
P1—C7 | 1.796 (2) | C16—C17 | 1.359 (5) |
P1—C13 | 1.794 (2) | C16—H16 | 0.9600 |
C1—C6 | 1.384 (3) | C17—C18 | 1.366 (4) |
C1—C2 | 1.393 (3) | C17—H17 | 0.9600 |
C2—C3 | 1.380 (3) | C18—H18 | 0.9600 |
C2—H2 | 0.9600 | C19—C20 | 1.495 (3) |
C3—C4 | 1.369 (4) | O2—C19 | 1.316 (3) |
C3—H3 | 0.9600 | O2—H1 | 1.00 (4) |
C4—C5 | 1.374 (4) | O3—C19 | 1.210 (3) |
C4—H4 | 0.9600 | C20—C21 | 1.371 (3) |
C5—C6 | 1.390 (3) | C20—C29 | 1.430 (3) |
C5—H5 | 0.9600 | C21—C22 | 1.398 (4) |
C6—H6 | 0.9600 | C21—H21 | 0.9600 |
C7—C8 | 1.373 (3) | C22—C23 | 1.351 (4) |
C7—C12 | 1.374 (3) | C22—H22 | 0.9600 |
C8—C9 | 1.384 (3) | C23—C24 | 1.404 (4) |
C8—H8 | 0.9600 | C23—H23 | 0.9600 |
C9—C10 | 1.351 (4) | C24—C25 | 1.414 (4) |
C9—H9 | 0.9600 | C24—C29 | 1.424 (3) |
C10—C11 | 1.357 (4) | C25—C26 | 1.348 (4) |
C10—H10 | 0.9600 | C25—H25 | 0.9600 |
C11—C12 | 1.380 (4) | C26—C27 | 1.398 (4) |
C11—H11 | 0.9600 | C26—H26 | 0.9600 |
C12—H12 | 0.9600 | C27—C28 | 1.368 (4) |
C13—C14 | 1.379 (3) | C27—H27 | 0.9600 |
C13—C18 | 1.389 (3) | C28—C29 | 1.412 (3) |
C14—C15 | 1.385 (3) | C28—H28 | 0.9600 |
C14—H14 | 0.9600 | | |
| | | |
O1—P1—C1 | 112.42 (10) | C15—C14—H14 | 120.0 |
O1—P1—C7 | 109.77 (9) | C16—C15—C14 | 120.1 (3) |
O1—P1—C13 | 112.66 (10) | C16—C15—H15 | 120.0 |
C1—P1—C7 | 108.59 (9) | C14—C15—H15 | 120.0 |
C1—P1—C13 | 105.34 (10) | C17—C16—C15 | 120.0 (3) |
C7—P1—C13 | 107.83 (10) | C17—C16—H16 | 120.0 |
C6—C1—C2 | 118.9 (2) | C15—C16—H16 | 120.0 |
C2—C1—P1 | 122.26 (16) | C16—C17—C18 | 120.4 (3) |
C6—C1—P1 | 118.82 (17) | C16—C17—H17 | 119.8 |
C3—C2—C1 | 120.7 (2) | C18—C17—H17 | 119.8 |
C3—C2—H2 | 119.6 | C17—C18—C13 | 120.8 (3) |
C1—C2—H2 | 119.6 | C17—C18—H18 | 119.6 |
C4—C3—C2 | 120.0 (3) | C13—C18—H18 | 119.6 |
C4—C3—H3 | 120.0 | C19—O2—H1 | 112 (2) |
C2—C3—H3 | 120.0 | O3—C19—O2 | 121.7 (2) |
C3—C4—C5 | 119.9 (2) | O3—C19—C20 | 124.7 (3) |
C3—C4—H4 | 120.0 | O2—C19—C20 | 113.6 (2) |
C5—C4—H4 | 120.0 | C21—C20—C29 | 119.8 (2) |
C4—C5—C6 | 120.7 (2) | C21—C20—C19 | 117.6 (2) |
C4—C5—H5 | 119.6 | C29—C20—C19 | 122.6 (2) |
C6—C5—H5 | 119.6 | C20—C21—C22 | 121.5 (3) |
C1—C6—C5 | 119.7 (2) | C20—C21—H21 | 119.2 |
C1—C6—H6 | 120.2 | C22—C21—H21 | 119.2 |
C5—C6—H6 | 120.2 | C23—C22—C21 | 119.8 (3) |
C8—C7—C12 | 118.3 (2) | C23—C22—H22 | 120.1 |
C8—C7—P1 | 123.26 (16) | C21—C22—H22 | 120.1 |
C12—C7—P1 | 118.45 (17) | C22—C23—C24 | 121.4 (3) |
C7—C8—C9 | 120.5 (2) | C22—C23—H23 | 119.3 |
C7—C8—H8 | 119.7 | C24—C23—H23 | 119.3 |
C9—C8—H8 | 119.8 | C23—C24—C25 | 120.8 (3) |
C10—C9—C8 | 120.4 (3) | C23—C24—C29 | 119.6 (3) |
C10—C9—H9 | 119.8 | C25—C24—C29 | 119.6 (3) |
C8—C9—H9 | 119.8 | C26—C25—C24 | 121.3 (3) |
C9—C10—C11 | 119.9 (3) | C26—C25—H25 | 119.3 |
C9—C10—H10 | 120.0 | C24—C25—H25 | 119.3 |
C11—C10—H10 | 120.0 | C25—C26—C27 | 119.5 (3) |
C10—C11—C12 | 120.2 (2) | C25—C26—H26 | 120.2 |
C10—C11—H11 | 119.9 | C27—C26—H26 | 120.2 |
C12—C11—H11 | 119.9 | C28—C27—C26 | 121.2 (3) |
C7—C12—C11 | 120.7 (2) | C28—C27—H27 | 119.4 |
C7—C12—H12 | 119.7 | C26—C27—H27 | 119.4 |
C11—C12—H12 | 119.7 | C27—C28—C29 | 121.0 (3) |
C14—C13—C18 | 118.6 (2) | C27—C28—H28 | 119.5 |
C14—C13—P1 | 123.81 (17) | C29—C28—H28 | 119.5 |
C18—C13—P1 | 117.46 (19) | C28—C29—C24 | 117.3 (2) |
C13—C14—C15 | 120.1 (2) | C28—C29—C20 | 124.8 (2) |
C13—C14—H14 | 120.0 | C24—C29—C20 | 117.9 (2) |
| | | |
O1—P1—C1—C6 | 16.3 (2) | C18—C13—C14—C15 | −0.5 (3) |
C13—P1—C1—C6 | 139.37 (17) | P1—C13—C14—C15 | 175.61 (18) |
C7—P1—C1—C6 | −105.33 (18) | C13—C14—C15—C16 | 0.6 (4) |
O1—P1—C1—C2 | −163.81 (18) | C14—C15—C16—C17 | 0.0 (4) |
C13—P1—C1—C2 | −40.8 (2) | C15—C16—C17—C18 | −0.7 (5) |
C7—P1—C1—C2 | 74.5 (2) | C16—C17—C18—C13 | 0.8 (5) |
C6—C1—C2—C3 | 0.7 (4) | C14—C13—C18—C17 | −0.2 (4) |
P1—C1—C2—C3 | −179.11 (19) | P1—C13—C18—C17 | −176.6 (2) |
C1—C2—C3—C4 | −0.5 (4) | O3—C19—C20—C21 | −174.7 (2) |
C2—C3—C4—C5 | −0.1 (4) | O2—C19—C20—C21 | 6.8 (3) |
C3—C4—C5—C6 | 0.5 (4) | O3—C19—C20—C29 | 7.4 (3) |
C2—C1—C6—C5 | −0.4 (3) | O2—C19—C20—C29 | −171.15 (18) |
P1—C1—C6—C5 | 179.50 (18) | C29—C20—C21—C22 | −0.3 (4) |
C4—C5—C6—C1 | −0.3 (4) | C19—C20—C21—C22 | −178.3 (2) |
O1—P1—C7—C8 | −164.4 (2) | C20—C21—C22—C23 | 1.0 (4) |
C13—P1—C7—C8 | 72.6 (2) | C21—C22—C23—C24 | −0.6 (4) |
C1—P1—C7—C8 | −41.1 (2) | C22—C23—C24—C25 | 178.9 (3) |
O1—P1—C7—C12 | 14.2 (2) | C22—C23—C24—C29 | −0.4 (4) |
C13—P1—C7—C12 | −108.85 (19) | C23—C24—C25—C26 | −180.0 (3) |
C1—P1—C7—C12 | 137.48 (18) | C29—C24—C25—C26 | −0.7 (4) |
C12—C7—C8—C9 | 0.5 (4) | C24—C25—C26—C27 | 0.3 (4) |
P1—C7—C8—C9 | 179.0 (2) | C25—C26—C27—C28 | 0.1 (4) |
C7—C8—C9—C10 | 1.2 (5) | C26—C27—C28—C29 | −0.1 (4) |
C8—C9—C10—C11 | −2.4 (5) | C27—C28—C29—C24 | −0.2 (3) |
C9—C10—C11—C12 | 1.8 (5) | C27—C28—C29—C20 | 178.6 (2) |
C8—C7—C12—C11 | −1.0 (4) | C23—C24—C29—C28 | 179.9 (2) |
P1—C7—C12—C11 | −179.7 (2) | C25—C24—C29—C28 | 0.6 (3) |
C10—C11—C12—C7 | −0.1 (4) | C23—C24—C29—C20 | 1.0 (3) |
O1—P1—C13—C14 | −104.48 (19) | C25—C24—C29—C20 | −178.32 (19) |
C7—P1—C13—C14 | 16.8 (2) | C21—C20—C29—C28 | −179.5 (2) |
C1—P1—C13—C14 | 132.63 (19) | C19—C20—C29—C28 | −1.6 (3) |
O1—P1—C13—C18 | 71.7 (2) | C21—C20—C29—C24 | −0.7 (3) |
C7—P1—C13—C18 | −167.05 (18) | C19—C20—C29—C24 | 177.23 (18) |
C1—P1—C13—C18 | −51.2 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.00 (3) | 1.60 (3) | 2.592 (2) | 170 (3) |
C11—H11···O2i | 0.96 | 2.49 | 3.383 (4) | 156 |
C17—H17···O3ii | 0.96 | 2.31 | 3.203 (4) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z. |
Experimental details
Crystal data |
Chemical formula | C18H15OP·C11H8O2 |
Mr | 450.44 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 296 |
a, b, c (Å) | 8.963 (1), 16.303 (1), 16.673 (1) |
β (°) | 104.784 (7) |
V (Å3) | 2355.7 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.15 |
Crystal size (mm) | 0.30 × 0.28 × 0.12 |
|
Data collection |
Diffractometer | Siemens P4 diffractometer |
Absorption correction | – |
No. of measured, independent and observed [I > 2σ(I)] reflections | 5488, 4083, 2933 |
Rint | 0.021 |
(sin θ/λ)max (Å−1) | 0.594 |
|
Refinement |
R[F2 > 2σ(F2)], wR(F2), S | 0.041, 0.111, 1.01 |
No. of reflections | 4083 |
No. of parameters | 302 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.21, −0.22 |
Selected geometric parameters (Å, º) topP1—O1 | 1.4880 (15) | C19—C20 | 1.495 (3) |
P1—C1 | 1.799 (2) | O2—C19 | 1.316 (3) |
P1—C7 | 1.796 (2) | O2—H1 | 1.00 (4) |
P1—C13 | 1.794 (2) | O3—C19 | 1.210 (3) |
| | | |
O1—P1—C1 | 112.42 (10) | C12—C7—P1 | 118.45 (17) |
O1—P1—C7 | 109.77 (9) | C14—C13—P1 | 123.81 (17) |
O1—P1—C13 | 112.66 (10) | C18—C13—P1 | 117.46 (19) |
C1—P1—C7 | 108.59 (9) | O3—C19—O2 | 121.7 (2) |
C1—P1—C13 | 105.34 (10) | O3—C19—C20 | 124.7 (3) |
C7—P1—C13 | 107.83 (10) | O2—C19—C20 | 113.6 (2) |
C2—C1—P1 | 122.26 (16) | C21—C20—C19 | 117.6 (2) |
C6—C1—P1 | 118.82 (17) | C29—C20—C19 | 122.6 (2) |
C8—C7—P1 | 123.26 (16) | | |
| | | |
O1—P1—C1—C6 | 16.3 (2) | O3—C19—C20—C21 | −174.7 (2) |
O1—P1—C7—C12 | 14.2 (2) | C25—C24—C29—C20 | −178.32 (19) |
O1—P1—C13—C18 | 71.7 (2) | | |
Hydrogen-bond geometry (Å, º) top
D—H···A | D—H | H···A | D···A | D—H···A |
O2—H1···O1 | 1.00 (3) | 1.60 (3) | 2.592 (2) | 170 (3) |
C11—H11···O2i | 0.96 | 2.49 | 3.383 (4) | 156 |
C17—H17···O3ii | 0.96 | 2.31 | 3.203 (4) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y, z. |
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The role of hydrogen bonds in crystal engineering and creation of supramolecular structures has attracted considerable research interest in recent years (Shan et al., 2002; Lehn, 1995). Because of its strong directional interaction, the hydrogen bond can orient molecules into predictable aggregate patterns and often dictate the preferred molecular packing arrangement in organic crystals (Desiraju & Steiner, 1999; Etter et al., 1986, 1988, 1990; Rebek et al., 1987, 1988). On the other hand, the triphenylphosphine oxide (TPPO) molecule has a great conformational flexibility and hydrogen-bond formation ability. The O atom of TPPO can act as a single, double or triple hydrogen-bond acceptor, and the orientation of the phenyl groups is not restricted to certain torsion-angle values (Llamas-Saiz et al., 1991; Ferguson & Glidewell, 1988). These properties make TPPO a versatile hydrogen-bond acceptor and a very useful crystallization aid (Etter et al., 1988). As part of our studies on the role of hydrogen bonding in the interaction of TPPO with organic acids, the crystal structure determination of the title compound, (I), was undertaken and the results are presented here.
A view of (I) with the atomic numbering scheme is given in Fig. 1 and selected geometric parameters are given in Table 1.
The title compound is isostructural with triphenylphosphine oxide 3-chlorobenzoic acid, (II) (Al-Farhan, 2003). The main hydrogen bond in the crystal structure is the O2—H1···O1 interaction (Table 2); the C19—O2···O1 and P1—O1···O2 angles are 118.2 (2) and 142.97 (10)°. If weak C—H···O interactions are also taken into consideration then the 1-naphthoic acid, through its carboxyl group, is bonded to three TPPO molecules via four hydrogen bonds [O1···H1 = 1.60 Å, O3···H6 = 2.70 Å, O2···H11(-x + 1, −y + 2, −z + 1) = 2.49 Å and O3···H17(x + 1, y, z) = 2.31 Å], which assemble the supramolecule. The above first two O···H interactions are involved in a hydrogen-bonded cyclic arrangement [graph set R22(9); Bernstein et al., 1995] and atom O3 acts as a bifurcated hydrogen-bond acceptor. The main hydrogen bond has little effect on the O═P bond length; the O1═P1 distance [1.492 (2) Å] is only 0.009 Å longer than the corresponding distance in free TPPO (Al-Farhan, 1992). The C═O [1.210 (3) Å] and C—OH [1.316 (3) Å] bond lengths in the carboxyl group are statistically equal to the corresponding bonds [1.214 (3) and 1.312 (3) Å, respectively] in the crystal structure of 1-naphthoic acid (Fitzgerald & Gerkin, 1993).
The O—P—C—C torsion angles of the TPPO moieties are 16.3 (2), 14.2 (2) and 71.7 (2)° in (I), and 21.2 (2), 33.3 (2) and 74.8 (2)° in (II); these values are distinctly different from the minimum-energy conformation threefold symmetry and torsion angles of 40°) deduced from analysis of the observed conformations of a wide range of TPPO derivatives (Bye et al., 1982).
The naphthalene core is planar within ±0.014 (2) Å. The dihedral angle between the plane of the carboxyl group and the plane of the phenyl ring is 8.1 (3) and 3.0 (4)° in (I) and (II), respectively.
Examination of the structure with PLATON (Spek, 2003) showed that there were no solvent-accessible voids in the crystal structure of (I).