Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010943/cv6309sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010943/cv6309Isup2.hkl |
CCDC reference: 242321
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989); cell refinement: MSC/AFC Software Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1998); software used to prepare material for publication: SHELXL97, PARST97 (Nardelli, 1996) and WinGX (Farrugia, 1999).
C13H15N2O4PS | F(000) = 680 |
Mr = 326.30 | Dx = 1.403 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 20 reflections |
a = 8.5760 (9) Å | θ = 20.1–28.6° |
b = 14.9072 (9) Å | µ = 3.00 mm−1 |
c = 12.0912 (5) Å | T = 293 K |
β = 92.146 (7)° | Plate, colorless |
V = 1544.7 (2) Å3 | 0.2 × 0.2 × 0.05 mm |
Z = 4 |
Rigaku AFC-5S diffractometer | 1105 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.025 |
Graphite monochromator | θmax = 68.5°, θmin = 4.7° |
ω scans | h = −2→10 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = −1→17 |
Tmin = 0.530, Tmax = 0.725 | l = −14→14 |
2930 measured reflections | 3 standard reflections every 150 reflections |
2751 independent reflections | intensity decay: none |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.047 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.127 | w = [exp{4.20(sinθ/λ)2}]/[σ2(Fo2) + (0.0533P)2]
where P = 0.33Fo2 + 0.67Fc2 |
S = 1.01 | (Δ/σ)max < 0.001 |
2751 reflections | Δρmax = 0.62 e Å−3 |
230 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0009 (2) |
Experimental. 1H NMR spectrum at 100 MHz was recorded on a Tesla BS 567 A, and 31P NMR was recorded on a Bruker HX360 spectrometer with H3PO4 as external standard. |
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 | 0.44353 (14) | 0.37743 (8) | 0.14102 (10) | 0.0600 (4) | |
O11 | 0.3762 (4) | 0.2994 (2) | 0.2082 (3) | 0.0890 (11) | |
C12 | 0.4304 (8) | 0.2867 (4) | 0.3208 (4) | 0.136 (3) | |
H121 | 0.5414 | 0.2780 | 0.3233 | 0.163* | |
H122 | 0.3807 | 0.2349 | 0.3509 | 0.163* | |
H123 | 0.4053 | 0.3387 | 0.3635 | 0.163* | |
O13 | 0.3394 (4) | 0.3626 (2) | 0.0286 (3) | 0.0807 (10) | |
C14 | 0.1785 (6) | 0.3672 (4) | 0.0244 (4) | 0.0901 (17) | |
H141 | 0.1370 | 0.3186 | 0.0664 | 0.108* | |
H142 | 0.1406 | 0.3628 | −0.0511 | 0.108* | |
H143 | 0.1459 | 0.4232 | 0.0550 | 0.108* | |
S2 | 0.43411 (15) | 0.49539 (9) | 0.20234 (11) | 0.0807 (5) | |
N3 | 0.6186 (4) | 0.3491 (2) | 0.1028 (3) | 0.0571 (10) | |
C31 | 0.7495 (7) | 0.4106 (4) | 0.0942 (6) | 0.0736 (16) | |
H311 | 0.844 (6) | 0.383 (3) | 0.134 (4) | 0.100 (19)* | |
H312 | 0.722 (6) | 0.469 (3) | 0.132 (4) | 0.100 (18)* | |
H313 | 0.765 (6) | 0.416 (4) | 0.016 (5) | 0.11 (2)* | |
N4 | 0.6286 (4) | 0.2618 (2) | 0.0635 (3) | 0.0570 (9) | |
C5 | 0.7543 (5) | 0.2367 (3) | 0.0201 (4) | 0.0548 (12) | |
O61 | 0.6861 (3) | −0.00697 (19) | −0.0240 (2) | 0.0599 (8) | |
C62 | 0.6787 (5) | 0.0789 (3) | 0.0108 (4) | 0.0572 (12) | |
H62 | 0.589 (5) | 0.089 (3) | 0.065 (3) | 0.092 (16)* | |
C63 | 0.7734 (5) | 0.1444 (3) | −0.0192 (3) | 0.0494 (10) | |
C64 | 0.8989 (5) | 0.1264 (3) | −0.0948 (3) | 0.0533 (11) | |
O641 | 0.9890 (4) | 0.1847 (2) | −0.1258 (3) | 0.0765 (10) | |
C65 | 1.0254 (5) | 0.0026 (4) | −0.1985 (4) | 0.0607 (12) | |
H65 | 1.104 (5) | 0.043 (3) | −0.212 (3) | 0.062 (14)* | |
C66 | 1.0287 (6) | −0.0846 (4) | −0.2342 (4) | 0.0680 (14) | |
H66 | 1.112 (6) | −0.103 (3) | −0.278 (4) | 0.11 (2)* | |
C67 | 0.9151 (6) | −0.1443 (3) | −0.2012 (4) | 0.0681 (14) | |
H67 | 0.919 (5) | −0.208 (3) | −0.221 (4) | 0.087 (17)* | |
C68 | 0.8014 (6) | −0.1179 (3) | −0.1302 (4) | 0.0651 (13) | |
H68 | 0.718 (5) | −0.162 (3) | −0.106 (3) | 0.074 (14)* | |
C69 | 0.8010 (5) | −0.0295 (3) | −0.0963 (3) | 0.0528 (11) | |
C70 | 0.9101 (5) | 0.0326 (3) | −0.1288 (3) | 0.0494 (10) | |
H51 | 0.847 (4) | 0.274 (2) | 0.022 (3) | 0.041 (10)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
P1 | 0.0585 (7) | 0.0583 (7) | 0.0640 (7) | −0.0095 (7) | 0.0149 (6) | −0.0090 (6) |
O11 | 0.094 (3) | 0.082 (2) | 0.092 (3) | −0.025 (2) | 0.027 (2) | −0.001 (2) |
C12 | 0.198 (8) | 0.123 (5) | 0.080 (4) | −0.029 (5) | −0.085 (5) | 0.018 (4) |
O13 | 0.065 (2) | 0.097 (3) | 0.080 (2) | −0.005 (2) | −0.0048 (18) | −0.030 (2) |
C14 | 0.067 (3) | 0.099 (4) | 0.102 (4) | −0.011 (3) | −0.016 (3) | 0.008 (4) |
S2 | 0.0767 (9) | 0.0708 (8) | 0.0958 (10) | −0.0071 (7) | 0.0190 (8) | −0.0305 (8) |
N3 | 0.046 (2) | 0.052 (2) | 0.073 (3) | −0.0095 (17) | 0.0040 (19) | −0.0088 (18) |
C31 | 0.058 (3) | 0.067 (4) | 0.097 (5) | −0.016 (3) | 0.012 (3) | −0.022 (3) |
N4 | 0.054 (2) | 0.050 (2) | 0.067 (2) | −0.0053 (18) | 0.0016 (19) | −0.0032 (19) |
C5 | 0.047 (3) | 0.052 (3) | 0.065 (3) | −0.003 (2) | −0.003 (2) | 0.000 (2) |
O61 | 0.0569 (18) | 0.0479 (17) | 0.076 (2) | −0.0092 (15) | 0.0128 (16) | −0.0025 (17) |
C62 | 0.047 (2) | 0.060 (3) | 0.065 (3) | −0.006 (2) | 0.005 (2) | −0.005 (2) |
C63 | 0.043 (2) | 0.053 (3) | 0.052 (3) | 0.000 (2) | −0.002 (2) | −0.003 (2) |
C64 | 0.049 (2) | 0.053 (3) | 0.058 (3) | −0.006 (2) | 0.000 (2) | 0.003 (2) |
O641 | 0.074 (2) | 0.0560 (19) | 0.102 (3) | −0.0160 (17) | 0.0319 (19) | 0.0028 (18) |
C65 | 0.056 (3) | 0.067 (3) | 0.059 (3) | 0.006 (3) | 0.007 (2) | 0.004 (3) |
C66 | 0.059 (3) | 0.081 (4) | 0.064 (3) | 0.012 (3) | 0.003 (3) | −0.004 (3) |
C67 | 0.075 (3) | 0.053 (3) | 0.076 (3) | 0.006 (3) | −0.003 (3) | −0.007 (3) |
C68 | 0.069 (3) | 0.056 (3) | 0.070 (3) | −0.002 (3) | 0.004 (3) | −0.002 (3) |
C69 | 0.052 (3) | 0.054 (3) | 0.053 (3) | 0.003 (2) | −0.003 (2) | 0.002 (2) |
C70 | 0.048 (2) | 0.048 (2) | 0.052 (3) | 0.000 (2) | −0.003 (2) | 0.003 (2) |
P1—O11 | 1.543 (3) | C5—H51 | 0.97 (3) |
P1—O13 | 1.613 (3) | O61—C62 | 1.349 (5) |
P1—N3 | 1.643 (3) | O61—C69 | 1.383 (5) |
P1—S2 | 1.911 (2) | C62—C63 | 1.330 (5) |
O11—C12 | 1.435 (5) | C62—H62 | 1.04 (4) |
C12—H121 | 0.9600 | C63—C64 | 1.462 (5) |
C12—H122 | 0.9600 | C64—O641 | 1.231 (5) |
C12—H123 | 0.9600 | C64—C70 | 1.462 (6) |
O13—C14 | 1.381 (5) | C65—C66 | 1.371 (7) |
C14—H141 | 0.9600 | C65—C70 | 1.396 (6) |
C14—H142 | 0.9600 | C65—H65 | 0.92 (4) |
C14—H143 | 0.9600 | C66—C67 | 1.390 (7) |
N3—N4 | 1.389 (4) | C66—H66 | 0.94 (5) |
N3—C31 | 1.456 (6) | C67—C68 | 1.381 (6) |
C31—H311 | 1.02 (5) | C67—H67 | 0.98 (4) |
C31—H312 | 1.02 (5) | C68—C69 | 1.380 (6) |
C31—H313 | 0.96 (5) | C68—H68 | 1.02 (4) |
N4—C5 | 1.272 (5) | C69—C70 | 1.384 (5) |
C5—C63 | 1.467 (5) | ||
O11—P1—O13 | 97.7 (2) | N4—C5—H51 | 122 (2) |
O11—P1—N3 | 108.6 (2) | C63—C5—H51 | 116 (2) |
O13—P1—N3 | 102.1 (2) | C62—O61—C69 | 118.1 (3) |
O11—P1—S2 | 117.9 (2) | C63—C62—O61 | 125.1 (4) |
O13—P1—S2 | 115.0 (2) | C63—C62—H62 | 123 (3) |
N3—P1—S2 | 113.5 (1) | O61—C62—H62 | 112 (3) |
C12—O11—P1 | 119.0 (3) | C62—C63—C64 | 120.5 (4) |
O11—C12—H121 | 109.5 | C62—C63—C5 | 121.5 (4) |
O11—C12—H122 | 109.5 | C64—C63—C5 | 118.0 (4) |
H121—C12—H122 | 109.5 | O641—C64—C70 | 122.7 (4) |
O11—C12—H123 | 109.5 | O641—C64—C63 | 123.1 (4) |
H121—C12—H123 | 109.5 | C70—C64—C63 | 114.2 (4) |
H122—C12—H123 | 109.5 | C66—C65—C70 | 121.2 (5) |
C14—O13—P1 | 123.0 (3) | C66—C65—H65 | 123 (3) |
O13—C14—H141 | 109.5 | C70—C65—H65 | 116 (3) |
O13—C14—H142 | 109.5 | C65—C66—C67 | 119.6 (5) |
H141—C14—H142 | 109.5 | C65—C66—H66 | 118 (3) |
O13—C14—H143 | 109.5 | C67—C66—H66 | 122 (3) |
H141—C14—H143 | 109.5 | C68—C67—C66 | 121.0 (5) |
H142—C14—H143 | 109.5 | C68—C67—H67 | 117 (3) |
N4—N3—C31 | 120.5 (4) | C66—C67—H67 | 121 (3) |
N4—N3—P1 | 114.0 (3) | C69—C68—C67 | 117.8 (5) |
C31—N3—P1 | 125.0 (3) | C69—C68—H68 | 121 (2) |
N3—C31—H311 | 108 (3) | C67—C68—H68 | 121 (2) |
N3—C31—H312 | 108 (3) | C68—C69—O61 | 115.4 (4) |
H311—C31—H312 | 109 (4) | C68—C69—C70 | 123.1 (4) |
N3—C31—H313 | 105 (3) | O61—C69—C70 | 121.5 (4) |
H311—C31—H313 | 111 (4) | C69—C70—C65 | 117.3 (4) |
H312—C31—H313 | 114 (4) | C69—C70—C64 | 120.5 (4) |
C5—N4—N3 | 118.7 (4) | C65—C70—C64 | 122.1 (4) |
N4—C5—C63 | 121.1 (4) | ||
O13—P1—O11—C12 | −177.5 (4) | C5—C63—C64—O641 | 0.5 (6) |
N3—P1—O11—C12 | 76.9 (4) | C62—C63—C64—C70 | −1.6 (6) |
S2—P1—O11—C12 | −53.8 (5) | C5—C63—C64—C70 | 179.5 (4) |
O11—P1—O13—C14 | 60.5 (4) | C70—C65—C66—C67 | 0.3 (7) |
N3—P1—O13—C14 | 171.4 (4) | C65—C66—C67—C68 | −2.0 (8) |
S2—P1—O13—C14 | −65.2 (4) | C66—C67—C68—C69 | 2.3 (7) |
O11—P1—N3—N4 | 43.7 (3) | C67—C68—C69—O61 | −179.1 (4) |
O13—P1—N3—N4 | −58.8 (3) | C67—C68—C69—C70 | −1.0 (7) |
S2—P1—N3—N4 | 176.8 (2) | C62—O61—C69—C68 | −179.1 (4) |
O11—P1—N3—C31 | −144.7 (5) | C62—O61—C69—C70 | 2.7 (6) |
O13—P1—N3—C31 | 112.8 (5) | C68—C69—C70—C65 | −0.5 (6) |
S2—P1—N3—C31 | −11.6 (5) | O61—C69—C70—C65 | 177.5 (4) |
C31—N3—N4—C5 | 0.1 (6) | C68—C69—C70—C64 | 176.8 (4) |
P1—N3—N4—C5 | 172.1 (3) | O61—C69—C70—C64 | −5.2 (6) |
N3—N4—C5—C63 | 177.9 (4) | C66—C65—C70—C69 | 0.9 (6) |
C69—O61—C62—C63 | 0.3 (6) | C66—C65—C70—C64 | −176.4 (4) |
O61—C62—C63—C64 | −0.7 (7) | O641—C64—C70—C69 | −176.6 (4) |
O61—C62—C63—C5 | 178.2 (4) | C63—C64—C70—C69 | 4.4 (6) |
N4—C5—C63—C62 | −15.8 (7) | O641—C64—C70—C65 | 0.6 (7) |
N4—C5—C63—C64 | 163.2 (4) | C63—C64—C70—C65 | −178.4 (4) |
C62—C63—C64—O641 | 179.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C65—H65···O641 | 0.92 (4) | 2.56 (4) | 2.873 (6) | 101 (3) |
C62—H62···O61i | 1.04 (5) | 2.69 (5) | 3.316 (5) | 119 (3) |
C67—H67···O641ii | 0.98 (5) | 2.59 (4) | 3.417 (6) | 142 (4) |
Symmetry codes: (i) −x+1, −y, −z; (ii) −x+2, y−1/2, −z−1/2. |