Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100001517/qa0216sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100001517/qa0216Isup2.hkl |
CCDC reference: 143329
According to Fluck et al. (1973), a solution of ethyldiphenylphosphine in benzene was slowly dropped into a suspension of pyridine-dithiomonometaphosphoryl fluoride in benzene with stirring. After 1 h, the solid product was filtered and recrystallized from a solution in benzene/acetonitrile.
For the studied crystal, a ΔF2-based absorption correction was carried out. The calculation made with ABSCOR (Stoe & Cie, 1997), a modification of DIFABS (Walker & Stuart, 1983). Unlike DIFABS, ABSCOR works with F2 values instead of F. All H atoms were refined [C—H 0.89 (2)–0.91 (2) Å].
Data collection: IPDS2.87 (Stoe & Cie, 1997); cell refinement: IPDS2.87 (Stoe & Cie, 1997); data reduction: IPDS2.87 (Stoe & Cie, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: XSTEP-2.18 (Stoe & Cie, 1997); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
C5H6N+·H2PSO3− | F(000) = 400 |
Mr = 193.15 | Dx = 1.612 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 6.7837 (13) Å | Cell parameters from 1775 reflections |
b = 9.0268 (11) Å | θ = 2.5–25.0° |
c = 13.237 (2) Å | µ = 0.56 mm−1 |
β = 101.02 (2)° | T = 180 K |
V = 795.7 (2) Å3 | Plate, yellow |
Z = 4 | 0.40 × 0.28 × 0.12 mm |
Stoe IPDS diffractometer | 1540 independent reflections |
Radiation source: fine-focus sealed X-ray tube | 1260 reflections with I > 2σ(I) |
Planar graphite monochromator | Rint = 0.038 |
Detector resolution: 6.667 pixels mm-1 | θmax = 26.0°, θmin = 2.8° |
ϕ–oscill., ϕ–incr. = 1.5°, 133 exposures scans | h = −8→8 |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | k = −11→10 |
Tmin = 0.806, Tmax = 0.935 | l = −16→16 |
4980 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)] = 0.029 | Hydrogen site location: difference Fourier map |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.04 | Calculated w = 1/[σ2(Fo2) + (0.0472P)2] where P = (Fo2 + 2Fc2)/3 |
1538 reflections | (Δ/σ)max = 0.001 |
126 parameters | Δρmax = 0.34 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C5H6N+·H2PSO3− | V = 795.7 (2) Å3 |
Mr = 193.15 | Z = 4 |
Monoclinic, P21/n | Mo Kα radiation |
a = 6.7837 (13) Å | µ = 0.56 mm−1 |
b = 9.0268 (11) Å | T = 180 K |
c = 13.237 (2) Å | 0.40 × 0.28 × 0.12 mm |
β = 101.02 (2)° |
Stoe IPDS diffractometer | 1540 independent reflections |
Absorption correction: part of the refinement model (ΔF) see _publ_section_exptl_prep | 1260 reflections with I > 2σ(I) |
Tmin = 0.806, Tmax = 0.935 | Rint = 0.038 |
4980 measured reflections |
R[F2 > 2σ(F2)] = 0.029 | 0 restraints |
wR(F2) = 0.077 | All H-atom parameters refined |
S = 1.04 | Δρmax = 0.34 e Å−3 |
1538 reflections | Δρmin = −0.35 e Å−3 |
126 parameters |
Experimental. During data collection the crystal was in cold N2 gas of the Cryostream Cooler (Oxford Cryosystems, 1992) mounted on a ϕ-axis diffractometer supplied with an area detector. |
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 on F2 for ALL reflections except for 2 with very negative F2 or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating R-factors 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 | ||
C2 | 0.2976 (3) | 1.1222 (2) | 1.04011 (14) | 0.0223 (4) | |
H2 | 0.309 (3) | 1.214 (2) | 1.0178 (15) | 0.028 (5)* | |
C3 | 0.3346 (3) | 1.0828 (2) | 1.14227 (14) | 0.0238 (4) | |
H3 | 0.381 (3) | 1.152 (2) | 1.1909 (16) | 0.027 (5)* | |
C4 | 0.3066 (2) | 0.9365 (2) | 1.16783 (14) | 0.0237 (4) | |
H4 | 0.337 (3) | 0.912 (2) | 1.2350 (17) | 0.026 (5)* | |
C5 | 0.2420 (3) | 0.8338 (2) | 1.09145 (14) | 0.0231 (4) | |
H5 | 0.218 (3) | 0.739 (2) | 1.1057 (15) | 0.022 (5)* | |
C6 | 0.2090 (2) | 0.8782 (2) | 0.99048 (14) | 0.0207 (4) | |
H6 | 0.163 (3) | 0.817 (2) | 0.9381 (16) | 0.024 (5)* | |
P1 | 0.13611 (6) | 1.00598 (4) | 0.68966 (3) | 0.01481 (15) | |
S1 | 0.31967 (6) | 0.99166 (5) | 0.59164 (3) | 0.02010 (15) | |
N1 | 0.2376 (2) | 1.0202 (2) | 0.96762 (12) | 0.0191 (3) | |
H1N | 0.213 (3) | 1.050 (3) | 0.9044 (19) | 0.032 (6)* | |
O1 | 0.1059 (2) | 0.85400 (13) | 0.74198 (10) | 0.0236 (3) | |
H1Y | 0.1897 (19) | 0.7923 (6) | 0.7282 (13) | 0.026* | |
O2 | −0.0836 (2) | 1.0518 (2) | 0.63523 (9) | 0.0274 (3) | |
H2Y | −0.1075 (11) | 1.0184 (19) | 0.5749 (5) | 0.030* | |
O3 | 0.1920 (2) | 1.11798 (13) | 0.77550 (9) | 0.0209 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C2 | 0.0226 (8) | 0.0212 (9) | 0.0228 (9) | 0.0007 (7) | 0.0036 (7) | 0.0015 (8) |
C3 | 0.0241 (9) | 0.0281 (11) | 0.0184 (9) | −0.0008 (7) | 0.0018 (7) | −0.0050 (8) |
C4 | 0.0214 (8) | 0.0356 (11) | 0.0143 (9) | 0.0049 (8) | 0.0040 (7) | 0.0037 (8) |
C5 | 0.0233 (9) | 0.0217 (10) | 0.0245 (9) | 0.0025 (7) | 0.0047 (7) | 0.0059 (8) |
C6 | 0.0205 (8) | 0.0226 (9) | 0.0186 (9) | 0.0009 (7) | 0.0028 (7) | −0.0047 (8) |
P1 | 0.0208 (2) | 0.0118 (3) | 0.0111 (2) | 0.00026 (15) | 0.0013 (2) | −0.0010 (2) |
S1 | 0.0233 (2) | 0.0231 (3) | 0.0140 (2) | −0.0012 (2) | 0.0038 (2) | −0.0012 (2) |
N1 | 0.0192 (7) | 0.0257 (8) | 0.0125 (7) | 0.0029 (6) | 0.0030 (5) | 0.0018 (6) |
O1 | 0.0320 (7) | 0.0137 (6) | 0.0286 (7) | 0.0017 (5) | 0.0142 (5) | 0.0017 (5) |
O2 | 0.0264 (6) | 0.0388 (8) | 0.0154 (6) | 0.0102 (6) | 0.0002 (5) | −0.0049 (6) |
O3 | 0.0335 (7) | 0.0166 (6) | 0.0122 (6) | −0.0048 (5) | 0.0033 (5) | −0.0028 (5) |
C2—N1 | 1.336 (2) | C6—N1 | 1.339 (2) |
C2—C3 | 1.374 (3) | C6—H6 | 0.90 (2) |
C2—H2 | 0.89 (2) | P1—O3 | 1.5141 (12) |
C3—C4 | 1.385 (3) | P1—O1 | 1.5678 (12) |
C3—H3 | 0.91 (2) | P1—O2 | 1.5816 (13) |
C4—C5 | 1.380 (3) | P1—S1 | 1.9669 (7) |
C4—H4 | 0.90 (2) | N1—H1N | 0.86 (2) |
C5—C6 | 1.372 (3) | O1—H1Y | 0.84 |
C5—H5 | 0.90 (2) | O2—H2Y | 0.84 |
N1—C2—C3 | 120.1 (2) | N1—C6—H6 | 117.4 (13) |
N1—C2—H2 | 116.0 (13) | C5—C6—H6 | 122.8 (13) |
C3—C2—H2 | 123.9 (13) | O3—P1—O1 | 106.73 (7) |
C2—C3—C4 | 118.6 (2) | O3—P1—O2 | 104.26 (7) |
C2—C3—H3 | 119.6 (13) | O1—P1—O2 | 103.82 (7) |
C4—C3—H3 | 121.7 (13) | O3—P1—S1 | 116.08 (5) |
C5—C4—C3 | 120.1 (2) | O1—P1—S1 | 112.74 (5) |
C5—C4—H4 | 122.4 (14) | O2—P1—S1 | 112.15 (5) |
C3—C4—H4 | 117.5 (14) | C2—N1—C6 | 122.3 (2) |
C6—C5—C4 | 119.1 (2) | C2—N1—H1N | 117.2 (16) |
C6—C5—H5 | 118.7 (13) | C6—N1—H1N | 120.5 (16) |
C4—C5—H5 | 122.1 (12) | P1—O1—H1Y | 109.47 (5) |
N1—C6—C5 | 119.7 (2) | P1—O2—H2Y | 109.47 (5) |
N1—C2—C3—C4 | −0.6 (2) | C4—C5—C6—N1 | −0.8 (2) |
C2—C3—C4—C5 | −0.3 (2) | C3—C2—N1—C6 | 0.8 (2) |
C3—C4—C5—C6 | 0.9 (2) | C5—C6—N1—C2 | −0.1 (2) |
Experimental details
Crystal data | |
Chemical formula | C5H6N+·H2PSO3− |
Mr | 193.15 |
Crystal system, space group | Monoclinic, P21/n |
Temperature (K) | 180 |
a, b, c (Å) | 6.7837 (13), 9.0268 (11), 13.237 (2) |
β (°) | 101.02 (2) |
V (Å3) | 795.7 (2) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.56 |
Crystal size (mm) | 0.40 × 0.28 × 0.12 |
Data collection | |
Diffractometer | Stoe IPDS diffractometer |
Absorption correction | Part of the refinement model (ΔF) see _publ_section_exptl_prep |
Tmin, Tmax | 0.806, 0.935 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 4980, 1540, 1260 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.029, 0.077, 1.04 |
No. of reflections | 1538 |
No. of parameters | 126 |
H-atom treatment | All H-atom parameters refined |
Δρmax, Δρmin (e Å−3) | 0.34, −0.35 |
Computer programs: IPDS2.87 (Stoe & Cie, 1997), SHELXS97 (Sheldrick, 1990), SHELXL97 (Sheldrick, 1997), XSTEP-2.18 (Stoe & Cie, 1997).