Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270101006710/de1168sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270101006710/de1168Isup2.hkl |
CCDC reference: 173362
Data collection: SMART (Siemens, 1996); cell refinement: SMART; data reduction: SHELXTL (Sheldrick, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.
Fig. 1. The structure of (I) showing hydrogen bonds between symmetry-related species. The displacement ellipsoids are shown at 30% probability level. |
C36H30NP2+·HO4S−·CHCl3 | Z = 4 |
Mr = 754.99 | F(000) = 1560 |
Monoclinic, P21/n | Dx = 1.397 Mg m−3 |
a = 15.3399 (13) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 16.2211 (13) Å | µ = 0.44 mm−1 |
c = 15.6888 (13) Å | T = 173 K |
β = 113.101 (1)° | Prism, colorless |
V = 3590.8 (5) Å3 | 0.43 × 0.20 × 0.20 mm |
CCD area detector diffractometer | 6269 independent reflections |
Radiation source: fine-focus sealed tube | 4010 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.058 |
ϕ and ω scans | θmax = 25.0°, θmin = 2.5° |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | h = −18→16 |
Tmin = 0.832, Tmax = 0.917 | k = −19→19 |
27441 measured reflections | l = −18→18 |
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)] = 0.061 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 0.99 | w = 1/[σ2(Fo2) + (0.084P)2] where P = (Fo2 + 2Fc2)/3 |
6269 reflections | (Δ/σ)max = 0.001 |
434 parameters | Δρmax = 0.45 e Å−3 |
0 restraints | Δρmin = −0.42 e Å−3 |
C36H30NP2+·HO4S−·CHCl3 | V = 3590.8 (5) Å3 |
Mr = 754.99 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 15.3399 (13) Å | µ = 0.44 mm−1 |
b = 16.2211 (13) Å | T = 173 K |
c = 15.6888 (13) Å | 0.43 × 0.20 × 0.20 mm |
β = 113.101 (1)° |
CCD area detector diffractometer | 6269 independent reflections |
Absorption correction: empirical (using intensity measurements) (SADABS; Blessing, 1995) | 4010 reflections with I > 2σ(I) |
Tmin = 0.832, Tmax = 0.917 | Rint = 0.058 |
27441 measured reflections |
R[F2 > 2σ(F2)] = 0.061 | 0 restraints |
wR(F2) = 0.153 | H-atom parameters constrained |
S = 0.99 | Δρmax = 0.45 e Å−3 |
6269 reflections | Δρmin = −0.42 e Å−3 |
434 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 | ||
S | 0.62658 (8) | 1.06605 (8) | 0.54548 (8) | 0.0474 (3) | |
Cl1 | 0.65012 (9) | 0.38986 (8) | 0.07487 (9) | 0.0670 (4) | |
Cl2 | 0.54802 (11) | 0.47980 (9) | −0.09140 (15) | 0.1184 (7) | |
Cl3 | 0.63338 (10) | 0.32483 (10) | −0.10125 (9) | 0.0806 (4) | |
P1 | 0.76240 (7) | 1.07083 (6) | 0.09653 (6) | 0.0264 (2) | |
P2 | 0.81761 (6) | 0.90164 (5) | 0.07528 (6) | 0.0253 (2) | |
O1 | 0.5433 (2) | 1.09141 (18) | 0.4556 (2) | 0.0535 (8) | |
H1 | 0.5129 | 1.0492 | 0.4293 | 0.080* | |
O2 | 0.5849 (2) | 1.02619 (18) | 0.60232 (19) | 0.0534 (8) | |
O3 | 0.6862 (3) | 1.0120 (3) | 0.5218 (3) | 0.1013 (15) | |
O4 | 0.6717 (2) | 1.1414 (2) | 0.5866 (2) | 0.0760 (10) | |
N | 0.8105 (2) | 0.98327 (17) | 0.12825 (19) | 0.0269 (7) | |
C1 | 0.8511 (2) | 1.1492 (2) | 0.1124 (2) | 0.0293 (8) | |
C2 | 0.8233 (3) | 1.2309 (2) | 0.0915 (3) | 0.0503 (12) | |
H2 | 0.7587 | 1.2456 | 0.0744 | 0.060* | |
C3 | 0.8884 (3) | 1.2905 (3) | 0.0955 (3) | 0.0544 (12) | |
H3 | 0.8687 | 1.3460 | 0.0797 | 0.065* | |
C4 | 0.9828 (3) | 1.2695 (2) | 0.1226 (3) | 0.0416 (10) | |
H4 | 1.0280 | 1.3103 | 0.1249 | 0.050* | |
C5 | 1.0110 (3) | 1.1898 (3) | 0.1460 (3) | 0.0415 (10) | |
H5 | 1.0761 | 1.1758 | 0.1660 | 0.050* | |
C6 | 0.9454 (3) | 1.1292 (2) | 0.1410 (3) | 0.0345 (9) | |
H6 | 0.9656 | 1.0739 | 0.1573 | 0.041* | |
C7 | 0.6957 (2) | 1.0986 (2) | 0.1645 (3) | 0.0301 (8) | |
C8 | 0.6251 (3) | 1.1578 (2) | 0.1326 (3) | 0.0430 (10) | |
H8 | 0.6109 | 1.1833 | 0.0742 | 0.052* | |
C9 | 0.5751 (3) | 1.1798 (3) | 0.1862 (3) | 0.0510 (12) | |
H9 | 0.5265 | 1.2201 | 0.1644 | 0.061* | |
C10 | 0.5962 (3) | 1.1429 (3) | 0.2714 (3) | 0.0488 (11) | |
H10 | 0.5623 | 1.1584 | 0.3082 | 0.059* | |
C11 | 0.6657 (3) | 1.0842 (3) | 0.3031 (3) | 0.0466 (11) | |
H11 | 0.6792 | 1.0587 | 0.3613 | 0.056* | |
C12 | 0.7166 (3) | 1.0619 (2) | 0.2507 (3) | 0.0366 (9) | |
H12 | 0.7655 | 1.0218 | 0.2733 | 0.044* | |
C13 | 0.6795 (2) | 1.0750 (2) | −0.0222 (2) | 0.0267 (8) | |
C14 | 0.6999 (3) | 1.1116 (2) | −0.0916 (2) | 0.0307 (9) | |
H14 | 0.7579 | 1.1405 | −0.0765 | 0.037* | |
C15 | 0.6360 (3) | 1.1066 (2) | −0.1837 (3) | 0.0376 (10) | |
H15 | 0.6506 | 1.1314 | −0.2313 | 0.045* | |
C16 | 0.5513 (3) | 1.0654 (2) | −0.2052 (3) | 0.0386 (10) | |
H16 | 0.5076 | 1.0616 | −0.2679 | 0.046* | |
C17 | 0.5299 (3) | 1.0296 (2) | −0.1361 (3) | 0.0369 (9) | |
H17 | 0.4711 | 1.0019 | −0.1514 | 0.044* | |
C18 | 0.5932 (3) | 1.0337 (2) | −0.0450 (3) | 0.0323 (9) | |
H18 | 0.5782 | 1.0085 | 0.0023 | 0.039* | |
C19 | 0.9351 (2) | 0.8591 (2) | 0.1341 (2) | 0.0261 (8) | |
C20 | 0.9878 (3) | 0.8797 (2) | 0.2259 (3) | 0.0344 (9) | |
H20 | 0.9609 | 0.9148 | 0.2576 | 0.041* | |
C21 | 1.0785 (3) | 0.8501 (2) | 0.2715 (3) | 0.0396 (10) | |
H21 | 1.1142 | 0.8655 | 0.3340 | 0.048* | |
C22 | 1.1174 (3) | 0.7979 (2) | 0.2263 (3) | 0.0396 (10) | |
H22 | 1.1800 | 0.7776 | 0.2576 | 0.048* | |
C23 | 1.0649 (3) | 0.7751 (2) | 0.1352 (3) | 0.0425 (10) | |
H23 | 1.0913 | 0.7386 | 0.1043 | 0.051* | |
C24 | 0.9736 (3) | 0.8057 (2) | 0.0890 (3) | 0.0354 (9) | |
H24 | 0.9376 | 0.7901 | 0.0267 | 0.043* | |
C25 | 0.8036 (2) | 0.9188 (2) | −0.0427 (2) | 0.0265 (8) | |
C26 | 0.8717 (3) | 0.9693 (2) | −0.0550 (3) | 0.0331 (9) | |
H26 | 0.9244 | 0.9882 | −0.0026 | 0.040* | |
C27 | 0.8626 (3) | 0.9918 (2) | −0.1432 (3) | 0.0417 (10) | |
H27 | 0.9091 | 1.0259 | −0.1512 | 0.050* | |
C28 | 0.7853 (3) | 0.9645 (3) | −0.2199 (3) | 0.0435 (11) | |
H28 | 0.7790 | 0.9798 | −0.2805 | 0.052* | |
C29 | 0.7181 (3) | 0.9152 (2) | −0.2078 (3) | 0.0422 (10) | |
H29 | 0.6651 | 0.8968 | −0.2603 | 0.051* | |
C30 | 0.7268 (3) | 0.8922 (2) | −0.1196 (3) | 0.0337 (9) | |
H30 | 0.6800 | 0.8582 | −0.1120 | 0.040* | |
C31 | 0.7331 (2) | 0.8259 (2) | 0.0769 (2) | 0.0293 (9) | |
C32 | 0.7270 (3) | 0.7497 (2) | 0.0337 (3) | 0.0369 (10) | |
H32 | 0.7670 | 0.7377 | 0.0020 | 0.044* | |
C33 | 0.6629 (3) | 0.6919 (3) | 0.0372 (3) | 0.0486 (11) | |
H33 | 0.6585 | 0.6400 | 0.0077 | 0.058* | |
C34 | 0.6048 (3) | 0.7089 (3) | 0.0834 (3) | 0.0578 (13) | |
H34 | 0.5607 | 0.6687 | 0.0857 | 0.069* | |
C35 | 0.6106 (3) | 0.7835 (3) | 0.1260 (4) | 0.0624 (14) | |
H35 | 0.5705 | 0.7949 | 0.1579 | 0.075* | |
C36 | 0.6742 (3) | 0.8422 (3) | 0.1229 (3) | 0.0455 (11) | |
H36 | 0.6776 | 0.8939 | 0.1524 | 0.055* | |
C37 | 0.6432 (3) | 0.4145 (3) | −0.0361 (4) | 0.0650 (14) | |
H37 | 0.7028 | 0.4437 | −0.0300 | 0.078* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0450 (7) | 0.0622 (8) | 0.0416 (6) | 0.0159 (6) | 0.0240 (6) | 0.0122 (6) |
Cl1 | 0.0726 (9) | 0.0568 (8) | 0.0678 (9) | 0.0134 (7) | 0.0233 (7) | −0.0080 (6) |
Cl2 | 0.0750 (10) | 0.0618 (10) | 0.1699 (18) | −0.0057 (8) | −0.0044 (11) | 0.0618 (10) |
Cl3 | 0.0753 (10) | 0.1052 (12) | 0.0591 (9) | −0.0124 (8) | 0.0238 (8) | −0.0106 (8) |
P1 | 0.0283 (5) | 0.0266 (5) | 0.0269 (5) | −0.0005 (4) | 0.0136 (4) | −0.0018 (4) |
P2 | 0.0273 (5) | 0.0244 (5) | 0.0269 (5) | −0.0001 (4) | 0.0134 (4) | 0.0011 (4) |
O1 | 0.0511 (18) | 0.063 (2) | 0.0432 (18) | 0.0076 (15) | 0.0155 (15) | 0.0158 (15) |
O2 | 0.062 (2) | 0.068 (2) | 0.0311 (16) | −0.0005 (16) | 0.0187 (15) | 0.0097 (14) |
O3 | 0.104 (3) | 0.139 (4) | 0.085 (3) | 0.083 (3) | 0.064 (3) | 0.036 (2) |
O4 | 0.055 (2) | 0.092 (3) | 0.080 (3) | −0.024 (2) | 0.0251 (19) | −0.001 (2) |
N | 0.0297 (17) | 0.0275 (17) | 0.0243 (17) | 0.0013 (13) | 0.0116 (14) | 0.0028 (13) |
C1 | 0.030 (2) | 0.031 (2) | 0.027 (2) | 0.0005 (17) | 0.0119 (18) | −0.0051 (16) |
C2 | 0.034 (2) | 0.036 (2) | 0.075 (3) | −0.002 (2) | 0.014 (2) | −0.002 (2) |
C3 | 0.054 (3) | 0.026 (2) | 0.073 (3) | −0.006 (2) | 0.014 (3) | 0.000 (2) |
C4 | 0.047 (3) | 0.039 (2) | 0.041 (2) | −0.019 (2) | 0.018 (2) | −0.0107 (19) |
C5 | 0.031 (2) | 0.045 (3) | 0.049 (3) | −0.004 (2) | 0.016 (2) | −0.004 (2) |
C6 | 0.033 (2) | 0.033 (2) | 0.036 (2) | 0.0008 (18) | 0.0122 (19) | 0.0009 (18) |
C7 | 0.029 (2) | 0.030 (2) | 0.032 (2) | −0.0023 (17) | 0.0134 (18) | −0.0055 (17) |
C8 | 0.057 (3) | 0.035 (2) | 0.048 (3) | 0.003 (2) | 0.033 (2) | −0.0024 (19) |
C9 | 0.058 (3) | 0.042 (3) | 0.065 (3) | 0.007 (2) | 0.038 (3) | −0.008 (2) |
C10 | 0.060 (3) | 0.052 (3) | 0.049 (3) | −0.010 (2) | 0.037 (3) | −0.022 (2) |
C11 | 0.052 (3) | 0.064 (3) | 0.028 (2) | −0.011 (2) | 0.021 (2) | −0.011 (2) |
C12 | 0.036 (2) | 0.046 (2) | 0.027 (2) | −0.0066 (19) | 0.0105 (19) | −0.0032 (18) |
C13 | 0.029 (2) | 0.0254 (19) | 0.029 (2) | 0.0026 (16) | 0.0141 (17) | −0.0012 (16) |
C14 | 0.031 (2) | 0.030 (2) | 0.032 (2) | 0.0035 (17) | 0.0146 (19) | 0.0016 (17) |
C15 | 0.043 (2) | 0.036 (2) | 0.037 (2) | 0.0042 (19) | 0.020 (2) | 0.0084 (18) |
C16 | 0.039 (2) | 0.046 (2) | 0.028 (2) | 0.008 (2) | 0.010 (2) | 0.0011 (19) |
C17 | 0.031 (2) | 0.040 (2) | 0.040 (3) | −0.0018 (18) | 0.013 (2) | −0.0040 (19) |
C18 | 0.033 (2) | 0.036 (2) | 0.034 (2) | 0.0013 (17) | 0.020 (2) | 0.0003 (18) |
C19 | 0.0265 (19) | 0.0226 (19) | 0.030 (2) | 0.0007 (15) | 0.0120 (17) | 0.0070 (16) |
C20 | 0.038 (2) | 0.034 (2) | 0.036 (2) | 0.0005 (18) | 0.019 (2) | 0.0060 (18) |
C21 | 0.037 (2) | 0.044 (2) | 0.031 (2) | 0.001 (2) | 0.006 (2) | 0.0090 (19) |
C22 | 0.032 (2) | 0.036 (2) | 0.048 (3) | 0.0075 (18) | 0.013 (2) | 0.014 (2) |
C23 | 0.039 (2) | 0.040 (2) | 0.051 (3) | 0.0100 (19) | 0.021 (2) | 0.001 (2) |
C24 | 0.035 (2) | 0.035 (2) | 0.036 (2) | 0.0019 (18) | 0.014 (2) | −0.0010 (18) |
C25 | 0.032 (2) | 0.026 (2) | 0.025 (2) | 0.0061 (16) | 0.0144 (18) | 0.0013 (15) |
C26 | 0.028 (2) | 0.037 (2) | 0.036 (2) | 0.0013 (17) | 0.0140 (19) | 0.0025 (18) |
C27 | 0.039 (2) | 0.049 (3) | 0.046 (3) | 0.012 (2) | 0.026 (2) | 0.017 (2) |
C28 | 0.058 (3) | 0.045 (3) | 0.036 (3) | 0.017 (2) | 0.028 (2) | 0.011 (2) |
C29 | 0.052 (3) | 0.039 (2) | 0.029 (2) | 0.010 (2) | 0.009 (2) | −0.0004 (18) |
C30 | 0.040 (2) | 0.026 (2) | 0.034 (2) | −0.0009 (18) | 0.014 (2) | −0.0002 (17) |
C31 | 0.028 (2) | 0.029 (2) | 0.028 (2) | 0.0024 (16) | 0.0082 (17) | 0.0076 (16) |
C32 | 0.043 (2) | 0.034 (2) | 0.033 (2) | −0.0043 (19) | 0.014 (2) | 0.0042 (18) |
C33 | 0.054 (3) | 0.034 (2) | 0.050 (3) | −0.009 (2) | 0.012 (2) | 0.003 (2) |
C34 | 0.040 (3) | 0.052 (3) | 0.080 (4) | −0.017 (2) | 0.022 (3) | 0.009 (3) |
C35 | 0.059 (3) | 0.056 (3) | 0.094 (4) | −0.008 (2) | 0.053 (3) | 0.001 (3) |
C36 | 0.045 (3) | 0.040 (2) | 0.064 (3) | −0.003 (2) | 0.035 (2) | 0.002 (2) |
C37 | 0.048 (3) | 0.052 (3) | 0.086 (4) | −0.013 (2) | 0.016 (3) | 0.017 (3) |
S—O3 | 1.418 (3) | C11—C12 | 1.386 (5) |
S—O4 | 1.428 (4) | C13—C14 | 1.380 (5) |
S—O2 | 1.439 (3) | C13—C18 | 1.399 (5) |
S—O1 | 1.541 (3) | C14—C15 | 1.394 (5) |
Cl1—C37 | 1.749 (5) | C15—C16 | 1.380 (5) |
Cl2—C37 | 1.736 (5) | C16—C17 | 1.378 (5) |
Cl3—C37 | 1.749 (5) | C17—C18 | 1.380 (5) |
P1—N | 1.588 (3) | C19—C24 | 1.387 (5) |
P1—C13 | 1.798 (4) | C19—C20 | 1.387 (5) |
P1—C7 | 1.801 (4) | C20—C21 | 1.378 (5) |
P1—C1 | 1.807 (4) | C21—C22 | 1.381 (5) |
P2—N | 1.590 (3) | C22—C23 | 1.388 (5) |
P2—C31 | 1.793 (4) | C23—C24 | 1.393 (5) |
P2—C25 | 1.800 (3) | C25—C30 | 1.382 (5) |
P2—C19 | 1.809 (3) | C25—C26 | 1.399 (5) |
C1—C6 | 1.374 (5) | C26—C27 | 1.384 (5) |
C1—C2 | 1.392 (5) | C27—C28 | 1.389 (6) |
C2—C3 | 1.374 (5) | C28—C29 | 1.376 (6) |
C3—C4 | 1.382 (6) | C29—C30 | 1.388 (5) |
C4—C5 | 1.367 (5) | C31—C36 | 1.386 (5) |
C5—C6 | 1.386 (5) | C31—C32 | 1.396 (5) |
C7—C8 | 1.386 (5) | C32—C33 | 1.375 (5) |
C7—C12 | 1.395 (5) | C33—C34 | 1.378 (6) |
C8—C9 | 1.389 (5) | C34—C35 | 1.369 (6) |
C9—C10 | 1.381 (6) | C35—C36 | 1.377 (6) |
C10—C11 | 1.368 (6) | ||
O3—S—O4 | 113.5 (3) | C14—C13—C18 | 119.3 (3) |
O3—S—O2 | 112.0 (2) | C14—C13—P1 | 123.1 (3) |
O4—S—O2 | 111.08 (19) | C18—C13—P1 | 117.4 (3) |
O3—S—O1 | 108.3 (2) | C13—C14—C15 | 120.5 (3) |
O4—S—O1 | 105.38 (19) | C16—C15—C14 | 119.6 (3) |
O2—S—O1 | 106.06 (17) | C17—C16—C15 | 120.2 (4) |
N—P1—C13 | 114.28 (15) | C16—C17—C18 | 120.5 (4) |
N—P1—C7 | 109.91 (16) | C17—C18—C13 | 119.9 (3) |
C13—P1—C7 | 105.57 (17) | C24—C19—C20 | 119.3 (3) |
N—P1—C1 | 110.71 (16) | C24—C19—P2 | 121.1 (3) |
C13—P1—C1 | 107.73 (16) | C20—C19—P2 | 119.6 (3) |
C7—P1—C1 | 108.37 (16) | C21—C20—C19 | 120.9 (4) |
N—P2—C31 | 111.41 (16) | C20—C21—C22 | 119.9 (4) |
N—P2—C25 | 113.83 (15) | C21—C22—C23 | 120.0 (4) |
C31—P2—C25 | 108.98 (17) | C22—C23—C24 | 119.9 (4) |
N—P2—C19 | 108.06 (16) | C19—C24—C23 | 120.0 (4) |
C31—P2—C19 | 108.20 (16) | C30—C25—C26 | 119.3 (3) |
C25—P2—C19 | 106.07 (16) | C30—C25—P2 | 124.5 (3) |
P1—N—P2 | 134.42 (19) | C26—C25—P2 | 115.9 (3) |
C6—C1—C2 | 119.2 (3) | C27—C26—C25 | 120.3 (4) |
C6—C1—P1 | 121.2 (3) | C26—C27—C28 | 120.0 (4) |
C2—C1—P1 | 119.5 (3) | C29—C28—C27 | 119.8 (4) |
C3—C2—C1 | 120.6 (4) | C28—C29—C30 | 120.6 (4) |
C2—C3—C4 | 119.7 (4) | C25—C30—C29 | 120.1 (4) |
C5—C4—C3 | 119.9 (4) | C36—C31—C32 | 119.2 (3) |
C4—C5—C6 | 120.6 (4) | C36—C31—P2 | 120.0 (3) |
C1—C6—C5 | 119.8 (4) | C32—C31—P2 | 120.8 (3) |
C8—C7—C12 | 119.7 (3) | C33—C32—C31 | 119.8 (4) |
C8—C7—P1 | 120.3 (3) | C32—C33—C34 | 120.3 (4) |
C12—C7—P1 | 119.9 (3) | C35—C34—C33 | 120.1 (4) |
C7—C8—C9 | 119.9 (4) | C34—C35—C36 | 120.3 (4) |
C10—C9—C8 | 119.9 (4) | C35—C36—C31 | 120.2 (4) |
C11—C10—C9 | 120.4 (4) | Cl2—C37—Cl1 | 110.3 (3) |
C10—C11—C12 | 120.4 (4) | Cl2—C37—Cl3 | 110.6 (3) |
C11—C12—C7 | 119.6 (4) | Cl1—C37—Cl3 | 110.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.85 | 2.633 (4) | 155.2 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C36H30NP2+·HO4S−·CHCl3 |
Mr | 754.99 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 173 |
a, b, c (Å) | 15.3399 (13), 16.2211 (13), 15.6888 (13) |
β (°) | 113.101 (1) |
V (Å3) | 3590.8 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.44 |
Crystal size (mm) | 0.43 × 0.20 × 0.20 |
Data collection | |
Diffractometer | CCD area detector diffractometer |
Absorption correction | Empirical (using intensity measurements) (SADABS; Blessing, 1995) |
Tmin, Tmax | 0.832, 0.917 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 27441, 6269, 4010 |
Rint | 0.058 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.061, 0.153, 0.99 |
No. of reflections | 6269 |
No. of parameters | 434 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.45, −0.42 |
Computer programs: SMART (Siemens, 1996), SMART, SHELXTL (Sheldrick, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), SHELXTL.
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1···O2i | 0.84 | 1.85 | 2.633 (4) | 155.2 |
Symmetry code: (i) −x+1, −y+2, −z+1. |
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Herein we report the structure of [Ph3P=N=PPh3]+[HSO4]-·CHCl3, (I), solated from chloroform and heptane as a by-product of the recrystallization of (PPN)[Re3Cl9(SO4)], which was prepared from the reaction of (Re3Cl9)x, PPNCl, and H2SO4 in water. \sch
The structure consists of discrete ions and well separated solvate molecules of chloroform. The location of the H atom on atom O(1) of the hydrosulfate is unequivocal as indicated by the longer S—O1 distance [1.541 (3) Å] compared with the other S—O bond lengths [average 1.428 (11) Å]. In 30 hydrosulfate ions reported in the Cambridge Structural Database (CSD; Allen & Kennard, 1993) the corresponding values averaged 1.53 (3) and 1.43 (2) Å, respectively. The central feature of the structure is hydrogen bonding between two hydrosulfate ions related by a crystallographic inversion centre (Fig. 1). Due to the symmetry considerations both hydrogen bonds have identical parameters. The O1···O2 (1 - x, 2 - y, 1 - z) distance is 2.633 (4) Å while the O—H···O angle is 155 (1)°. The corresponding values for 23 similar HSO4-—HSO4- hydrogen-bonding interactions in structures reported to the CSD comprised 2.58 (4) Å and 164 (10)°. The only structure with two symmetrical hydrogen bonds between two hydrosulfate moieties [average O···O separation 2.63 (1) Å, O—H.·O angle 150 (2)°] was reported for [Fe(TTP)(HSO4)].1/2C6H6 (TTP = tetraphenylporphinato) (Scheidt et al., 1988). The environment about the S atom is distorted tetrahedral with the O—S—O angles ranging from 105.38 (19)–113.5 (3)°. The [Ph3P═ N═PPh3]+ cation is rather typical. The P—N distance [average 1.589 (3) Å] is slightly longer than the average P═N distance of 1.576 (18) Å obtained by averaging 562 P—N distances in PPN+ ions reported to the CSD. The P—N—P angle in (I) [134.42 (19)°] is noticeably smaller than the average angle of 143 (8)° found in the same 562 PPN+ cations. The large s.u.'s calculated for the two parameters for complexes reported to the CSD reveal that the geometry about the N atom in PPN+ ions may vary substantially. Both phosphorus atoms in (I) are tetrahedral with the average C—P—C and C—P—N angles averaging 109 (3)°.