Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801010157/cv6030sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801010157/cv6030Isup2.hkl |
CCDC reference: 170775
The title compound was prepared according to the method of Pietrusiewicz et al. (1998) and stored in the dark at 293 K for four years.
Data collection: CrysAlis CCD (UNIL IC & Kuma, 2000); cell refinement: CrysAlis RED (UNIL IC & Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1990a); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997); software used to prepare material for publication: SHELXL97.
C45H39O3P3·C2H3N·H2O | F(000) = 820 |
Mr = 779.74 | Dx = 1.266 Mg m−3 |
Monoclinic, Pn | Mo Kα radiation, λ = 0.71073 Å |
a = 15.3382 (14) Å | Cell parameters from 8473 reflections |
b = 8.6418 (9) Å | θ = 2–22° |
c = 15.9748 (11) Å | µ = 0.19 mm−1 |
β = 105.034 (10)° | T = 291 K |
V = 2045.0 (3) Å3 | Pyramid, pale pink |
Z = 2 | 0.60 × 0.40 × 0.40 mm |
Kuma KM4-CCD diffractometer | 6643 independent reflections |
Radiation source: fine-focus sealed tube | 6532 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.060 |
ω scans | θmax = 25.2°, θmin = 3.5° |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | h = −18→18 |
Tmin = 0.894, Tmax = 0.928 | k = −10→10 |
20214 measured reflections | l = −19→18 |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.079 | w = 1/[σ2(Fo2) + (0.0113P)2 + 5.8292P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.164 | (Δ/σ)max = 0.003 |
S = 1.08 | Δρmax = 0.29 e Å−3 |
6643 reflections | Δρmin = −0.42 e Å−3 |
497 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
2 restraints | Extinction coefficient: 0.0083 (5) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: 0.24 (15) |
C45H39O3P3·C2H3N·H2O | V = 2045.0 (3) Å3 |
Mr = 779.74 | Z = 2 |
Monoclinic, Pn | Mo Kα radiation |
a = 15.3382 (14) Å | µ = 0.19 mm−1 |
b = 8.6418 (9) Å | T = 291 K |
c = 15.9748 (11) Å | 0.60 × 0.40 × 0.40 mm |
β = 105.034 (10)° |
Kuma KM4-CCD diffractometer | 6643 independent reflections |
Absorption correction: numerical (X-RED; Stoe & Cie, 1999) | 6532 reflections with I > 2σ(I) |
Tmin = 0.894, Tmax = 0.928 | Rint = 0.060 |
20214 measured reflections |
R[F2 > 2σ(F2)] = 0.079 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.164 | Δρmax = 0.29 e Å−3 |
S = 1.08 | Δρmin = −0.42 e Å−3 |
6643 reflections | Absolute structure: Flack (1983) |
497 parameters | Absolute structure parameter: 0.24 (15) |
2 restraints |
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 | −0.89339 (10) | −0.96860 (17) | −0.31681 (10) | 0.0421 (3) | |
P2 | −0.74371 (11) | −0.77740 (19) | −0.71926 (11) | 0.0489 (4) | |
P3 | −0.62228 (12) | −0.43955 (18) | −0.34069 (13) | 0.0543 (4) | |
O1 | −0.8595 (3) | −0.8535 (5) | −0.2459 (3) | 0.0549 (11) | |
O2 | −0.6797 (4) | −0.6471 (7) | −0.6904 (4) | 0.0841 (18) | |
O3 | −0.6191 (3) | −0.5182 (5) | −0.2568 (3) | 0.0649 (13) | |
C1 | −0.8119 (4) | −0.8575 (7) | −0.4433 (4) | 0.0409 (12) | |
C2 | −0.8334 (4) | −0.8705 (7) | −0.5331 (4) | 0.0451 (14) | |
H2 | −0.8548 | −0.9642 | −0.5591 | 0.054* | |
C3 | −0.8236 (4) | −0.7484 (7) | −0.5838 (4) | 0.0460 (14) | |
C4 | −0.7914 (4) | −0.6084 (7) | −0.5443 (4) | 0.0486 (14) | |
H4 | −0.7857 | −0.5240 | −0.5786 | 0.058* | |
C5 | −0.7679 (4) | −0.5925 (7) | −0.4557 (4) | 0.0447 (13) | |
C6 | −0.7793 (4) | −0.7163 (6) | −0.4047 (4) | 0.0460 (14) | |
H6 | −0.7653 | −0.7057 | −0.3448 | 0.055* | |
C7 | −0.8193 (4) | −0.9931 (7) | −0.3874 (4) | 0.0462 (14) | |
H7A | −0.7594 | −1.0177 | −0.3519 | 0.055* | |
H7B | −0.8402 | −1.0814 | −0.4247 | 0.055* | |
C8 | −0.8437 (4) | −0.7613 (8) | −0.6824 (4) | 0.0539 (16) | |
H8A | −0.8773 | −0.6706 | −0.7085 | 0.065* | |
H8B | −0.8814 | −0.8513 | −0.7015 | 0.065* | |
C9 | −0.7334 (4) | −0.4362 (7) | −0.4158 (4) | 0.0514 (15) | |
H9A | −0.7760 | −0.3961 | −0.3857 | 0.062* | |
H9B | −0.7322 | −0.3647 | −0.4623 | 0.062* | |
C10 | −0.8994 (4) | −1.1607 (7) | −0.2757 (3) | 0.0399 (12) | |
C11 | −0.9778 (6) | −1.2482 (9) | −0.2949 (7) | 0.088 (3) | |
H11 | −1.0321 | −1.2063 | −0.3268 | 0.105* | |
C12 | −0.9733 (7) | −1.3976 (10) | −0.2658 (8) | 0.119 (4) | |
H12 | −1.0256 | −1.4571 | −0.2803 | 0.143* | |
C13 | −0.8980 (6) | −1.4623 (9) | −0.2179 (6) | 0.073 (2) | |
H13 | −0.8982 | −1.5640 | −0.1989 | 0.087* | |
C14 | −0.8217 (6) | −1.3783 (9) | −0.1977 (5) | 0.073 (2) | |
H14 | −0.7681 | −1.4226 | −0.1658 | 0.088* | |
C15 | −0.8232 (5) | −1.2258 (9) | −0.2243 (5) | 0.073 (2) | |
H15 | −0.7711 | −1.1664 | −0.2068 | 0.088* | |
C16 | −1.0023 (4) | −0.9187 (7) | −0.3845 (4) | 0.0441 (13) | |
C17 | −1.0510 (5) | −0.8008 (8) | −0.3574 (6) | 0.068 (2) | |
H17 | −1.0262 | −0.7486 | −0.3058 | 0.082* | |
C18 | −1.1356 (6) | −0.7621 (11) | −0.4071 (7) | 0.094 (3) | |
H18 | −1.1683 | −0.6842 | −0.3889 | 0.113* | |
C19 | −1.1724 (6) | −0.8396 (12) | −0.4849 (6) | 0.086 (3) | |
H19 | −1.2290 | −0.8114 | −0.5190 | 0.103* | |
C20 | −1.1273 (6) | −0.9531 (13) | −0.5103 (6) | 0.094 (3) | |
H20 | −1.1541 | −1.0068 | −0.5609 | 0.113* | |
C21 | −1.0414 (5) | −0.9937 (9) | −0.4634 (5) | 0.0639 (19) | |
H21 | −1.0096 | −1.0702 | −0.4839 | 0.077* | |
C22 | −0.6971 (5) | −0.9642 (9) | −0.6866 (4) | 0.0587 (18) | |
C23 | −0.6045 (6) | −0.9815 (15) | −0.6644 (6) | 0.106 (4) | |
H23 | −0.5683 | −0.8940 | −0.6605 | 0.128* | |
C24 | −0.5641 (11) | −1.124 (2) | −0.6480 (10) | 0.167 (9) | |
H24 | −0.5016 | −1.1346 | −0.6331 | 0.201* | |
C25 | −0.6174 (17) | −1.248 (2) | −0.6541 (9) | 0.182 (12) | |
H25 | −0.5903 | −1.3447 | −0.6449 | 0.218* | |
C26 | −0.7071 (13) | −1.2407 (13) | −0.6725 (7) | 0.134 (6) | |
H26 | −0.7415 | −1.3298 | −0.6740 | 0.161* | |
C27 | −0.7477 (7) | −1.0970 (8) | −0.6894 (5) | 0.075 (2) | |
H27 | −0.8103 | −1.0899 | −0.7029 | 0.090* | |
C28 | −0.7794 (4) | −0.7865 (7) | −0.8352 (4) | 0.0504 (15) | |
C29 | −0.7380 (6) | −0.6925 (10) | −0.8824 (5) | 0.073 (2) | |
H29 | −0.6934 | −0.6234 | −0.8546 | 0.087* | |
C30 | −0.7632 (6) | −0.7014 (12) | −0.9715 (6) | 0.087 (3) | |
H30 | −0.7353 | −0.6357 | −1.0028 | 0.104* | |
C31 | −0.8264 (6) | −0.8006 (12) | −1.0156 (5) | 0.089 (3) | |
H31 | −0.8402 | −0.8056 | −1.0757 | 0.107* | |
C32 | −0.8700 (7) | −0.8946 (15) | −0.9698 (6) | 0.113 (4) | |
H32 | −0.9148 | −0.9626 | −0.9985 | 0.136* | |
C33 | −0.8454 (6) | −0.8858 (13) | −0.8778 (5) | 0.094 (3) | |
H33 | −0.8746 | −0.9484 | −0.8462 | 0.113* | |
C34 | −0.5964 (4) | −0.2366 (7) | −0.3248 (5) | 0.0589 (18) | |
C35 | −0.5912 (5) | −0.1390 (8) | −0.3930 (6) | 0.072 (2) | |
H35 | −0.5990 | −0.1800 | −0.4483 | 0.086* | |
C36 | −0.5748 (7) | 0.0162 (10) | −0.3798 (7) | 0.086 (3) | |
H36 | −0.5717 | 0.0803 | −0.4257 | 0.103* | |
C37 | −0.5630 (5) | 0.0758 (9) | −0.2976 (7) | 0.083 (3) | |
H37 | −0.5529 | 0.1813 | −0.2887 | 0.100* | |
C38 | −0.5659 (5) | −0.0181 (9) | −0.2273 (6) | 0.075 (2) | |
H38 | −0.5561 | 0.0224 | −0.1717 | 0.089* | |
C39 | −0.5840 (5) | −0.1739 (8) | −0.2436 (5) | 0.0610 (19) | |
H39 | −0.5879 | −0.2381 | −0.1980 | 0.073* | |
C40 | −0.5428 (4) | −0.5204 (7) | −0.3927 (5) | 0.0570 (18) | |
C41 | −0.5594 (5) | −0.5348 (9) | −0.4825 (5) | 0.071 (2) | |
H41 | −0.6140 | −0.4995 | −0.5176 | 0.085* | |
C42 | −0.4960 (6) | −0.6009 (11) | −0.5211 (7) | 0.089 (3) | |
H42 | −0.5083 | −0.6127 | −0.5809 | 0.107* | |
C43 | −0.4160 (6) | −0.6473 (11) | −0.4679 (8) | 0.091 (3) | |
H43 | −0.3727 | −0.6904 | −0.4923 | 0.109* | |
C44 | −0.3968 (6) | −0.6327 (12) | −0.3801 (8) | 0.095 (3) | |
H44 | −0.3408 | −0.6632 | −0.3457 | 0.114* | |
C45 | −0.4618 (5) | −0.5716 (9) | −0.3418 (6) | 0.075 (2) | |
H45 | −0.4500 | −0.5658 | −0.2817 | 0.090* | |
C98 | −1.0181 (7) | −0.4915 (14) | −0.5388 (7) | 0.103 (3) | |
C99 | −0.9645 (6) | −0.3658 (13) | −0.5603 (6) | 0.084 (3) | |
N99 | −0.9239 (7) | −0.2692 (11) | −0.5813 (8) | 0.122 (4) | |
O99 | −0.6897 (4) | −0.7247 (7) | −0.1543 (3) | 0.0827 (16) | |
H99O | −0.6751 | −0.6597 | −0.1804 | 0.124* | |
H99P | −0.7357 | −0.7767 | −0.1833 | 0.124* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0525 (8) | 0.0398 (7) | 0.0331 (8) | −0.0046 (7) | 0.0093 (7) | −0.0009 (6) |
P2 | 0.0561 (9) | 0.0514 (9) | 0.0383 (9) | −0.0073 (8) | 0.0108 (7) | −0.0018 (7) |
P3 | 0.0556 (9) | 0.0382 (8) | 0.0675 (12) | −0.0049 (7) | 0.0133 (8) | −0.0012 (8) |
O1 | 0.071 (3) | 0.050 (2) | 0.037 (2) | −0.009 (2) | 0.001 (2) | −0.0115 (19) |
O2 | 0.095 (4) | 0.087 (4) | 0.081 (4) | −0.050 (3) | 0.043 (3) | −0.036 (3) |
O3 | 0.081 (3) | 0.048 (3) | 0.061 (3) | −0.010 (2) | 0.010 (3) | 0.011 (2) |
C1 | 0.046 (3) | 0.045 (3) | 0.034 (3) | 0.004 (2) | 0.015 (3) | 0.010 (2) |
C2 | 0.056 (4) | 0.049 (3) | 0.031 (3) | 0.001 (3) | 0.014 (3) | 0.001 (3) |
C3 | 0.051 (3) | 0.052 (3) | 0.035 (3) | 0.006 (3) | 0.012 (3) | 0.010 (3) |
C4 | 0.052 (3) | 0.045 (3) | 0.047 (4) | 0.005 (3) | 0.010 (3) | 0.012 (3) |
C5 | 0.041 (3) | 0.040 (3) | 0.049 (4) | −0.006 (2) | 0.005 (3) | −0.001 (3) |
C6 | 0.052 (3) | 0.039 (3) | 0.048 (4) | −0.009 (3) | 0.015 (3) | −0.005 (3) |
C7 | 0.048 (3) | 0.041 (3) | 0.051 (4) | 0.000 (2) | 0.014 (3) | 0.016 (3) |
C8 | 0.054 (4) | 0.074 (4) | 0.031 (3) | 0.007 (3) | 0.006 (3) | 0.015 (3) |
C9 | 0.052 (3) | 0.043 (3) | 0.058 (4) | −0.003 (3) | 0.012 (3) | −0.002 (3) |
C10 | 0.048 (3) | 0.046 (3) | 0.025 (3) | 0.000 (3) | 0.009 (2) | 0.008 (2) |
C11 | 0.064 (5) | 0.053 (4) | 0.139 (9) | −0.005 (4) | 0.015 (5) | 0.032 (5) |
C12 | 0.087 (6) | 0.052 (5) | 0.191 (13) | −0.014 (5) | −0.012 (7) | 0.045 (6) |
C13 | 0.089 (6) | 0.049 (4) | 0.082 (6) | 0.003 (4) | 0.027 (5) | 0.019 (4) |
C14 | 0.088 (6) | 0.068 (5) | 0.057 (5) | 0.010 (4) | 0.005 (4) | 0.019 (4) |
C15 | 0.068 (5) | 0.079 (5) | 0.058 (5) | −0.016 (4) | −0.009 (4) | 0.033 (4) |
C16 | 0.051 (3) | 0.045 (3) | 0.038 (3) | 0.000 (3) | 0.017 (3) | 0.004 (3) |
C17 | 0.073 (5) | 0.058 (4) | 0.078 (6) | 0.007 (4) | 0.024 (4) | −0.011 (4) |
C18 | 0.068 (5) | 0.107 (7) | 0.105 (8) | 0.035 (5) | 0.017 (5) | −0.010 (6) |
C19 | 0.066 (5) | 0.104 (7) | 0.075 (6) | 0.010 (5) | −0.006 (5) | −0.005 (5) |
C20 | 0.076 (6) | 0.116 (8) | 0.077 (6) | 0.014 (5) | −0.006 (5) | −0.014 (6) |
C21 | 0.062 (4) | 0.073 (5) | 0.046 (4) | 0.005 (3) | −0.004 (3) | −0.021 (3) |
C22 | 0.061 (4) | 0.082 (5) | 0.026 (3) | 0.015 (4) | −0.002 (3) | −0.006 (3) |
C23 | 0.073 (6) | 0.164 (11) | 0.067 (6) | 0.046 (6) | −0.010 (5) | −0.037 (6) |
C24 | 0.136 (12) | 0.26 (2) | 0.076 (8) | 0.136 (15) | −0.034 (8) | −0.045 (13) |
C25 | 0.31 (3) | 0.174 (17) | 0.048 (7) | 0.16 (2) | 0.015 (13) | 0.012 (9) |
C26 | 0.281 (19) | 0.081 (7) | 0.059 (6) | 0.058 (10) | 0.075 (10) | 0.039 (5) |
C27 | 0.114 (7) | 0.049 (4) | 0.061 (5) | 0.000 (4) | 0.022 (5) | 0.010 (3) |
C28 | 0.061 (4) | 0.050 (3) | 0.042 (3) | 0.002 (3) | 0.015 (3) | 0.010 (3) |
C29 | 0.078 (5) | 0.080 (5) | 0.061 (5) | −0.013 (4) | 0.019 (4) | 0.016 (4) |
C30 | 0.080 (6) | 0.117 (7) | 0.064 (6) | −0.003 (5) | 0.018 (5) | 0.037 (5) |
C31 | 0.080 (6) | 0.141 (8) | 0.045 (4) | 0.007 (6) | 0.013 (4) | 0.034 (5) |
C32 | 0.094 (7) | 0.165 (11) | 0.064 (6) | −0.039 (7) | −0.010 (5) | 0.010 (7) |
C33 | 0.089 (6) | 0.145 (9) | 0.035 (4) | −0.047 (6) | −0.010 (4) | 0.028 (5) |
C34 | 0.048 (4) | 0.036 (3) | 0.088 (5) | −0.007 (3) | 0.010 (4) | −0.009 (3) |
C35 | 0.082 (5) | 0.048 (4) | 0.095 (6) | −0.013 (4) | 0.040 (5) | −0.001 (4) |
C36 | 0.101 (7) | 0.061 (5) | 0.105 (7) | −0.008 (5) | 0.046 (6) | 0.007 (5) |
C37 | 0.072 (5) | 0.042 (4) | 0.135 (9) | −0.007 (4) | 0.028 (6) | −0.003 (5) |
C38 | 0.074 (5) | 0.051 (4) | 0.093 (6) | −0.001 (4) | 0.011 (5) | −0.018 (4) |
C39 | 0.065 (4) | 0.042 (3) | 0.059 (4) | −0.006 (3) | −0.013 (4) | 0.002 (3) |
C40 | 0.051 (4) | 0.031 (3) | 0.088 (6) | −0.003 (3) | 0.018 (4) | −0.001 (3) |
C41 | 0.057 (4) | 0.082 (5) | 0.077 (5) | 0.013 (4) | 0.024 (4) | 0.001 (4) |
C42 | 0.085 (6) | 0.092 (6) | 0.105 (7) | −0.003 (5) | 0.050 (6) | −0.022 (5) |
C43 | 0.070 (6) | 0.091 (7) | 0.119 (9) | 0.022 (5) | 0.037 (6) | 0.007 (6) |
C44 | 0.056 (5) | 0.102 (7) | 0.119 (9) | 0.017 (5) | 0.009 (5) | 0.013 (6) |
C45 | 0.053 (4) | 0.066 (5) | 0.094 (6) | −0.001 (4) | −0.001 (4) | 0.009 (4) |
C98 | 0.097 (7) | 0.123 (9) | 0.085 (7) | −0.010 (6) | 0.020 (6) | 0.017 (6) |
C99 | 0.076 (6) | 0.095 (7) | 0.064 (5) | 0.029 (5) | −0.011 (4) | −0.028 (5) |
N99 | 0.114 (8) | 0.072 (5) | 0.160 (10) | 0.008 (5) | 0.000 (7) | 0.004 (6) |
O99 | 0.096 (4) | 0.090 (4) | 0.060 (3) | −0.019 (3) | 0.015 (3) | 0.020 (3) |
P1—O1 | 1.496 (4) | C20—H20 | 0.9300 |
P1—C16 | 1.791 (6) | C21—H21 | 0.9300 |
P1—C10 | 1.796 (6) | C22—C27 | 1.380 (11) |
P1—C7 | 1.809 (6) | C22—C23 | 1.381 (11) |
P2—O2 | 1.486 (5) | C23—C24 | 1.376 (18) |
P2—C8 | 1.785 (6) | C23—H23 | 0.9300 |
P2—C22 | 1.787 (7) | C24—C25 | 1.33 (3) |
P2—C28 | 1.792 (7) | C24—H24 | 0.9300 |
P3—O3 | 1.492 (5) | C25—C26 | 1.33 (2) |
P3—C40 | 1.786 (7) | C25—H25 | 0.9300 |
P3—C34 | 1.801 (6) | C26—C27 | 1.384 (13) |
P3—C9 | 1.812 (6) | C26—H26 | 0.9300 |
C1—C2 | 1.392 (8) | C27—H27 | 0.9300 |
C1—C6 | 1.400 (8) | C28—C33 | 1.366 (10) |
C1—C7 | 1.496 (7) | C28—C29 | 1.371 (9) |
C2—C3 | 1.361 (8) | C29—C30 | 1.377 (11) |
C2—H2 | 0.9300 | C29—H29 | 0.9300 |
C3—C4 | 1.395 (9) | C30—C31 | 1.347 (12) |
C3—C8 | 1.529 (8) | C30—H30 | 0.9300 |
C4—C5 | 1.374 (9) | C31—C32 | 1.377 (12) |
C4—H4 | 0.9300 | C31—H31 | 0.9300 |
C5—C6 | 1.382 (8) | C32—C33 | 1.421 (11) |
C5—C9 | 1.529 (8) | C32—H32 | 0.9300 |
C6—H6 | 0.9300 | C33—H33 | 0.9300 |
C7—H7A | 0.9700 | C34—C39 | 1.373 (10) |
C7—H7B | 0.9700 | C34—C35 | 1.397 (10) |
C8—H8A | 0.9700 | C35—C36 | 1.370 (11) |
C8—H8B | 0.9700 | C35—H35 | 0.9300 |
C9—H9A | 0.9700 | C36—C37 | 1.379 (13) |
C9—H9B | 0.9700 | C36—H36 | 0.9300 |
C10—C15 | 1.363 (9) | C37—C38 | 1.395 (12) |
C10—C11 | 1.385 (9) | C37—H37 | 0.9300 |
C11—C12 | 1.368 (10) | C38—C39 | 1.386 (10) |
C11—H11 | 0.9300 | C38—H38 | 0.9300 |
C12—C13 | 1.333 (12) | C39—H39 | 0.9300 |
C12—H12 | 0.9300 | C40—C45 | 1.370 (10) |
C13—C14 | 1.343 (11) | C40—C41 | 1.396 (10) |
C13—H13 | 0.9300 | C41—C42 | 1.400 (10) |
C14—C15 | 1.384 (10) | C41—H41 | 0.9300 |
C14—H14 | 0.9300 | C42—C43 | 1.360 (13) |
C15—H15 | 0.9300 | C42—H42 | 0.9300 |
C16—C17 | 1.396 (9) | C43—C44 | 1.362 (13) |
C16—C21 | 1.405 (9) | C43—H43 | 0.9300 |
C17—C18 | 1.376 (11) | C44—C45 | 1.402 (12) |
C17—H17 | 0.9300 | C44—H44 | 0.9300 |
C18—C19 | 1.395 (12) | C45—H45 | 0.9300 |
C18—H18 | 0.9300 | C98—C99 | 1.457 (15) |
C19—C20 | 1.323 (13) | C99—N99 | 1.142 (13) |
C19—H19 | 0.9300 | O99—H99O | 0.7674 |
C20—C21 | 1.382 (11) | O99—H99P | 0.8627 |
O1—P1—C16 | 112.5 (3) | C20—C19—H19 | 119.8 |
O1—P1—C10 | 112.3 (3) | C18—C19—H19 | 119.8 |
C16—P1—C10 | 108.4 (3) | C19—C20—C21 | 121.5 (9) |
O1—P1—C7 | 113.5 (3) | C19—C20—H20 | 119.2 |
C16—P1—C7 | 106.9 (3) | C21—C20—H20 | 119.2 |
C10—P1—C7 | 102.7 (3) | C20—C21—C16 | 119.6 (7) |
O2—P2—C8 | 113.2 (3) | C20—C21—H21 | 120.2 |
O2—P2—C22 | 114.3 (4) | C16—C21—H21 | 120.2 |
C8—P2—C22 | 106.7 (3) | C27—C22—C23 | 116.8 (8) |
O2—P2—C28 | 110.7 (3) | C27—C22—P2 | 124.3 (6) |
C8—P2—C28 | 106.6 (3) | C23—C22—P2 | 118.7 (8) |
C22—P2—C28 | 104.7 (3) | C24—C23—C22 | 121.9 (13) |
O3—P3—C40 | 111.8 (3) | C24—C23—H23 | 119.0 |
O3—P3—C34 | 111.2 (3) | C22—C23—H23 | 119.0 |
C40—P3—C34 | 107.1 (3) | C25—C24—C23 | 117.8 (16) |
O3—P3—C9 | 114.1 (3) | C25—C24—H24 | 121.1 |
C40—P3—C9 | 109.7 (3) | C23—C24—H24 | 121.1 |
C34—P3—C9 | 102.3 (3) | C24—C25—C26 | 124.1 (17) |
C2—C1—C6 | 119.1 (5) | C24—C25—H25 | 118.0 |
C2—C1—C7 | 121.2 (6) | C26—C25—H25 | 118.0 |
C6—C1—C7 | 119.6 (5) | C25—C26—C27 | 118.0 (16) |
C3—C2—C1 | 121.2 (6) | C25—C26—H26 | 121.0 |
C3—C2—H2 | 119.4 | C27—C26—H26 | 121.0 |
C1—C2—H2 | 119.4 | C22—C27—C26 | 121.3 (11) |
C2—C3—C4 | 119.0 (5) | C22—C27—H27 | 119.3 |
C2—C3—C8 | 122.2 (6) | C26—C27—H27 | 119.3 |
C4—C3—C8 | 118.8 (5) | C33—C28—C29 | 119.2 (7) |
C5—C4—C3 | 121.3 (5) | C33—C28—P2 | 122.0 (5) |
C5—C4—H4 | 119.3 | C29—C28—P2 | 118.8 (6) |
C3—C4—H4 | 119.3 | C28—C29—C30 | 119.3 (8) |
C4—C5—C6 | 119.4 (5) | C28—C29—H29 | 120.3 |
C4—C5—C9 | 119.2 (6) | C30—C29—H29 | 120.3 |
C6—C5—C9 | 121.4 (6) | C31—C30—C29 | 123.1 (8) |
C5—C6—C1 | 120.0 (6) | C31—C30—H30 | 118.4 |
C5—C6—H6 | 120.0 | C29—C30—H30 | 118.4 |
C1—C6—H6 | 120.0 | C30—C31—C32 | 118.7 (8) |
C1—C7—P1 | 116.0 (4) | C30—C31—H31 | 120.7 |
C1—C7—H7A | 108.3 | C32—C31—H31 | 120.7 |
P1—C7—H7A | 108.3 | C31—C32—C33 | 118.9 (9) |
C1—C7—H7B | 108.3 | C31—C32—H32 | 120.6 |
P1—C7—H7B | 108.3 | C33—C32—H32 | 120.6 |
H7A—C7—H7B | 107.4 | C28—C33—C32 | 120.8 (8) |
C3—C8—P2 | 112.6 (4) | C28—C33—H33 | 119.6 |
C3—C8—H8A | 109.1 | C32—C33—H33 | 119.6 |
P2—C8—H8A | 109.1 | C39—C34—C35 | 118.5 (6) |
C3—C8—H8B | 109.1 | C39—C34—P3 | 119.3 (6) |
P2—C8—H8B | 109.1 | C35—C34—P3 | 122.2 (6) |
H8A—C8—H8B | 107.8 | C36—C35—C34 | 121.1 (8) |
C5—C9—P3 | 115.3 (4) | C36—C35—H35 | 119.5 |
C5—C9—H9A | 108.5 | C34—C35—H35 | 119.5 |
P3—C9—H9A | 108.5 | C35—C36—C37 | 119.1 (9) |
C5—C9—H9B | 108.5 | C35—C36—H36 | 120.5 |
P3—C9—H9B | 108.5 | C37—C36—H36 | 120.5 |
H9A—C9—H9B | 107.5 | C36—C37—C38 | 121.7 (8) |
C15—C10—C11 | 117.8 (6) | C36—C37—H37 | 119.1 |
C15—C10—P1 | 119.0 (5) | C38—C37—H37 | 119.1 |
C11—C10—P1 | 123.2 (5) | C39—C38—C37 | 117.4 (8) |
C12—C11—C10 | 118.5 (8) | C39—C38—H38 | 121.3 |
C12—C11—H11 | 120.8 | C37—C38—H38 | 121.3 |
C10—C11—H11 | 120.8 | C34—C39—C38 | 122.2 (8) |
C13—C12—C11 | 123.4 (9) | C34—C39—H39 | 118.9 |
C13—C12—H12 | 118.3 | C38—C39—H39 | 118.9 |
C11—C12—H12 | 118.3 | C45—C40—C41 | 118.5 (7) |
C12—C13—C14 | 118.9 (7) | C45—C40—P3 | 118.3 (7) |
C12—C13—H13 | 120.6 | C41—C40—P3 | 123.2 (5) |
C14—C13—H13 | 120.6 | C40—C41—C42 | 121.7 (8) |
C13—C14—C15 | 119.8 (8) | C40—C41—H41 | 119.1 |
C13—C14—H14 | 120.1 | C42—C41—H41 | 119.1 |
C15—C14—H14 | 120.1 | C43—C42—C41 | 117.5 (9) |
C10—C15—C14 | 121.5 (7) | C43—C42—H42 | 121.2 |
C10—C15—H15 | 119.3 | C41—C42—H42 | 121.2 |
C14—C15—H15 | 119.3 | C42—C43—C44 | 122.3 (9) |
C17—C16—C21 | 118.4 (6) | C42—C43—H43 | 118.8 |
C17—C16—P1 | 118.6 (5) | C44—C43—H43 | 118.8 |
C21—C16—P1 | 123.0 (5) | C43—C44—C45 | 119.8 (8) |
C18—C17—C16 | 119.9 (8) | C43—C44—H44 | 120.1 |
C18—C17—H17 | 120.0 | C45—C44—H44 | 120.1 |
C16—C17—H17 | 120.0 | C40—C45—C44 | 120.0 (9) |
C17—C18—C19 | 120.0 (8) | C40—C45—H45 | 120.0 |
C17—C18—H18 | 120.0 | C44—C45—H45 | 120.0 |
C19—C18—H18 | 120.0 | N99—C99—C98 | 176.6 (11) |
C20—C19—C18 | 120.4 (8) | H99O—O99—H99P | 113.7 |
C2—C1—C7—P1 | −121.9 (6) | C8—P2—C28—C33 | −49.5 (8) |
C1—C7—P1—C10 | 170.6 (5) | C3—C8—P2—O2 | −56.7 (6) |
C7—P1—C10—C11 | −113.6 (7) | O2—P2—C22—C23 | −20.7 (7) |
C7—P1—C10—C15 | 65.2 (6) | O2—P2—C22—C27 | 165.5 (6) |
C6—C1—C7—P1 | 60.7 (7) | O2—P2—C28—C29 | 8.0 (7) |
C1—C7—P1—C16 | 56.7 (5) | O2—P2—C28—C33 | −173.0 (7) |
C7—P1—C16—C17 | −136.8 (5) | C4—C5—C9—P3 | −122.3 (6) |
C7—P1—C16—C21 | 43.8 (6) | C5—C9—P3—C34 | 169.3 (5) |
C1—C7—P1—O1 | −68.0 (5) | C9—P3—C34—C35 | −60.7 (7) |
O1—P1—C10—C11 | 124.1 (7) | C9—P3—C34—C39 | 117.3 (6) |
O1—P1—C10—C15 | −57.1 (6) | C6—C5—C9—P3 | 60.2 (7) |
O1—P1—C16—C17 | −11.6 (6) | C5—C9—P3—C40 | 55.8 (5) |
O1—P1—C16—C21 | 169.0 (5) | C9—P3—C40—C41 | 17.0 (7) |
C2—C3—C8—P2 | −102.3 (6) | C9—P3—C40—C45 | −162.5 (5) |
C3—C8—P2—C22 | 69.9 (5) | C5—C9—P3—O3 | −70.5 (5) |
C8—P2—C22—C23 | −146.6 (6) | O3—P3—C34—C35 | 177.1 (6) |
C8—P2—C22—C27 | 39.6 (7) | O3—P3—C34—C39 | −4.9 (7) |
C4—C3—C8—P2 | 75.5 (7) | O3—P3—C40—C41 | 144.6 (6) |
C3—C8—P2—C28 | −178.6 (5) | O3—P3—C40—C45 | −34.9 (6) |
C8—P2—C28—C29 | 131.5 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O99—H99P···O1 | 0.86 | 2.02 | 2.861 (7) | 166 |
O99—H99O···O3 | 0.77 | 2.06 | 2.821 (7) | 169 |
C15—H15···O1 | 0.93 | 3.02 | 3.268 (9) | 97 |
C17—H17···O1 | 0.93 | 2.65 | 3.048 (9) | 107 |
C23—H23···O2 | 0.93 | 2.70 | 3.099 (13) | 107 |
C45—H45···O3 | 0.93 | 2.76 | 3.093 (10) | 103 |
C29—H29···O2 | 0.93 | 2.58 | 2.989 (10) | 107 |
C39—H39···O3 | 0.93 | 2.60 | 3.021 (8) | 108 |
Experimental details
Crystal data | |
Chemical formula | C45H39O3P3·C2H3N·H2O |
Mr | 779.74 |
Crystal system, space group | Monoclinic, Pn |
Temperature (K) | 291 |
a, b, c (Å) | 15.3382 (14), 8.6418 (9), 15.9748 (11) |
β (°) | 105.034 (10) |
V (Å3) | 2045.0 (3) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.19 |
Crystal size (mm) | 0.60 × 0.40 × 0.40 |
Data collection | |
Diffractometer | Kuma KM4-CCD diffractometer |
Absorption correction | Numerical (X-RED; Stoe & Cie, 1999) |
Tmin, Tmax | 0.894, 0.928 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 20214, 6643, 6532 |
Rint | 0.060 |
(sin θ/λ)max (Å−1) | 0.600 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.079, 0.164, 1.08 |
No. of reflections | 6643 |
No. of parameters | 497 |
No. of restraints | 2 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.29, −0.42 |
Absolute structure | Flack (1983) |
Absolute structure parameter | 0.24 (15) |
Computer programs: CrysAlis CCD (UNIL IC & Kuma, 2000), CrysAlis RED (UNIL IC & Kuma, 2000), CrysAlis RED, SHELXS97 (Sheldrick, 1990a), SHELXL97 (Sheldrick, 1997), XP in SHELXTL/PC (Sheldrick, 1990b) and ORTEP-3 (Farrugia 1997), SHELXL97.
O1—P1—C16 | 112.5 (3) | O2—P2—C28 | 110.7 (3) |
O1—P1—C10 | 112.3 (3) | C8—P2—C28 | 106.6 (3) |
C16—P1—C10 | 108.4 (3) | C22—P2—C28 | 104.7 (3) |
O1—P1—C7 | 113.5 (3) | O3—P3—C40 | 111.8 (3) |
C16—P1—C7 | 106.9 (3) | O3—P3—C34 | 111.2 (3) |
C10—P1—C7 | 102.7 (3) | C40—P3—C34 | 107.1 (3) |
O2—P2—C8 | 113.2 (3) | O3—P3—C9 | 114.1 (3) |
O2—P2—C22 | 114.3 (4) | C40—P3—C9 | 109.7 (3) |
C8—P2—C22 | 106.7 (3) | C34—P3—C9 | 102.3 (3) |
C1—C7—P1—C10 | 170.6 (5) | C8—P2—C28—C33 | −49.5 (8) |
C7—P1—C10—C15 | 65.2 (6) | C3—C8—P2—O2 | −56.7 (6) |
C6—C1—C7—P1 | 60.7 (7) | O2—P2—C22—C27 | 165.5 (6) |
C1—C7—P1—C16 | 56.7 (5) | O2—P2—C28—C33 | −173.0 (7) |
C7—P1—C16—C21 | 43.8 (6) | C5—C9—P3—C34 | 169.3 (5) |
C1—C7—P1—O1 | −68.0 (5) | C9—P3—C34—C35 | −60.7 (7) |
O1—P1—C10—C15 | −57.1 (6) | C6—C5—C9—P3 | 60.2 (7) |
O1—P1—C16—C21 | 169.0 (5) | C5—C9—P3—C40 | 55.8 (5) |
C3—C8—P2—C22 | 69.9 (5) | C9—P3—C40—C41 | 17.0 (7) |
C8—P2—C22—C27 | 39.6 (7) | C5—C9—P3—O3 | −70.5 (5) |
C4—C3—C8—P2 | 75.5 (7) | O3—P3—C34—C35 | 177.1 (6) |
C3—C8—P2—C28 | −178.6 (5) | O3—P3—C40—C41 | 144.6 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O99—H99P···O1 | 0.86 | 2.02 | 2.861 (7) | 166.3 |
O99—H99O···O3 | 0.77 | 2.06 | 2.821 (7) | 168.5 |
C15—H15···O1 | 0.93 | 3.02 | 3.268 (9) | 97.3 |
C17—H17···O1 | 0.93 | 2.65 | 3.048 (9) | 106.7 |
C23—H23···O2 | 0.93 | 2.70 | 3.099 (13) | 106.9 |
C45—H45···O3 | 0.93 | 2.76 | 3.093 (10) | 102.6 |
C29—H29···O2 | 0.93 | 2.58 | 2.989 (10) | 106.9 |
C39—H39···O3 | 0.93 | 2.60 | 3.021 (8) | 108.4 |
The crystal and molecular structures of the title compound crystallizing in the P1 space group were previously determined [(I) hereafter; Cambridge Structural Database (CSD; Allen & Kennard, 1993) refcode GOKQAY (Pietrusiewicz et al., 1998)]. Since the crystal structure of (I) had two pairs of only slightly different molecules in the independent part of the unit cell, and the net constants were close to monoclinic system, we tried to obtain a second polymorph of (I), but all attempts failed. The crystals were stored in the dark at 293 K. After four years, we found that the crystals had changed in appearance. The colourless crystals of (I) had become pale pink. Thus, we decided to redetermine the crystal structure of the (I). Measurement of the unit-cell parameters revealed the monoclinic crystal system (II).
The perspective view of (II) and the atomic numbering scheme are shown in Fig. 1. A l l interatomic distances can be considered as normal. We could not localize the H atoms of the acetonitrile molecule, probably because of the fully disordered methyl group. These H atoms are not involved in any hydrogen bond which will be able to provide additional stabilization [the shortest methyl group carbon to nearest atom distance is 3.645 (12) Å]. The phenyl group including the C22 atom shows signs of disorder, but invoking this model did not improve the quality of the refinement; therefore, the model was not applied. The overall molecular geometry of (II) is similar to that of (I) (Pietrusiewicz et al., 1998). The weighted r.m.s. deviation for all atoms in (II) and the first and second molecules of (I) are 0.146 (3) and 0.154 (4) Å, respectively. Superposition of the two molecules, i.e. (II) and one of the molecules of (I), is shown in Fig. 2. The overall arrangement of the diphenylphosphine oxide substituents (best described by torsion angles, see Table 1) indicated by the P1 and P3 atoms is imposed by strong Owater—H···Ooxide hydrogen bonds (for details, see Table 2). These also affect the dihedral angle between the central benzene ring and P—CH2Cbenzene which amounts to 59.7 (3) and 58.9 (3)° for the branches indicated by the P1 and P3 atoms, and 76.2 (4) for the branch indicated by the P2 atom.
The phenyl rings make angles of 67.0 (3), 78.8 (3) and 76.6 (2)° with the substituents indicated by the P1, P2 and P3 atoms, respectively. All the P atoms adopt distorted tetrahedral geometry, with C—P—C angles equal or smaller than tetrahedral and O—P—C angles greater than tetrahedral (Table 1). It is possible to suggest that the steric effect imposed by the phenyl groups has no greater importance. All three diphenylphosphine oxide substituents are stabilized by weak hydrogen bonds Cphenyl—H···Ooxide (Table 2). For each substituent, one of the phenyl rings is almost coplanar with the P═O bond. The central benzene ring makes dihedral angles of 60.7 (3), 72.1 (2), 78.7 (3), 27.6 (3), 10.5 (2) and 82.8 (2)° with the phenyl rings indicated by the C10, C15, C22, C28, C34 and C40 atoms, respectively; the respective P atoms deviate by 0.14 (1), 0.04 (1), 0.21 (1), 0.07 (1), 0.06 (1) and 0.00 (1) Å from the indicated phenyl rings. There are no unusual intermolecular short contacts except for the hydrogen bonds described in Table 2.