Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536801019730/cv6079sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536801019730/cv6079Isup2.hkl |
CCDC reference: 177224
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.005 Å
- R factor = 0.054
- wR factor = 0.141
- Data-to-parameter ratio = 14.7
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry
Alert Level C:
REFLT_03 From the CIF: _diffrn_reflns_theta_max 72.60 From the CIF: _reflns_number_total 4266 TEST2: Reflns within _diffrn_reflns_theta_max Count of symmetry unique reflns 4506 Completeness (_total/calc) 94.67% Alert C: < 95% complete
0 Alert Level A = Potentially serious problem
0 Alert Level B = Potential problem
1 Alert Level C = Please check
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a); cell refinement: MSC/AFC Diffractometer Control Software; data reduction: TEXSAN (Molecular Structure Corporation, 1989b); program(s) used to solve structure: SHELXS86 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: ORTEX (McArdle, 1995) and PLUTON92 (Spek, 1992); software used to prepare material for publication: PARST97 (Nardelli, 1996).
C23H25N2O3PS | F(000) = 928 |
Mr = 440.48 | Dx = 1.290 Mg m−3 Dm = 1.289 Mg m−3 Dm measured by flotation in xylene, bromobenzene, heptane & toluene |
Monoclinic, P21/n | Cu Kα radiation, λ = 1.54178 Å |
a = 10.061 (1) Å | Cell parameters from 25 reflections |
b = 20.561 (1) Å | θ = 22.5–30.3° |
c = 11.375 (1) Å | µ = 2.15 mm−1 |
β = 105.38 (1)° | T = 293 K |
V = 2268.8 (3) Å3 | Plate, colourless |
Z = 4 | 0.45 × 0.4 × 0.2 mm |
Rigaku AFC-5S diffractometer | 3042 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.066 |
Graphite monochromator | θmax = 72.6°, θmin = 4.3° |
ω scans | h = 0→12 |
Absorption correction: analytical (de Meulenaer & Tompa, 1965) | k = 0→24 |
Tmin = 0.405, Tmax = 0.671 | l = −14→13 |
4505 measured reflections | 3 standard reflections every 150 reflections |
4266 independent reflections | intensity decay: <2% |
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)] = 0.054 | w = 1/[σ2(Fo2) + (0.0998P)2] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.141 | (Δ/σ)max = 0.001 |
S = 0.92 | Δρmax = 0.43 e Å−3 |
4266 reflections | Δρmin = −0.42 e Å−3 |
291 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
0 restraints | Extinction coefficient: 0.0159 (8) |
Primary atom site location: structure-invariant direct methods |
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 | ||
S1 | 0.85090 (7) | 0.68277 (3) | 0.22868 (6) | 0.0679 (2) | |
C1 | 0.8652 (2) | 0.63555 (11) | 0.3501 (2) | 0.0526 (5) | |
N1 | 0.8621 (2) | 0.65816 (10) | 0.46099 (19) | 0.0657 (6) | |
H1 | 0.873 (3) | 0.6285 (13) | 0.514 (3) | 0.073 (8)* | |
N2 | 0.8840 (2) | 0.57020 (10) | 0.34981 (19) | 0.0559 (5) | |
H2 | 0.883 (3) | 0.5539 (12) | 0.412 (2) | 0.057 (7)* | |
C2 | 0.8923 (2) | 0.53202 (11) | 0.2447 (2) | 0.0533 (5) | |
H201 | 0.893 (2) | 0.5608 (11) | 0.182 (2) | 0.057 (6)* | |
C3 | 0.7740 (3) | 0.48257 (13) | 0.2048 (3) | 0.0623 (6) | |
H301 | 0.797 (3) | 0.4645 (13) | 0.141 (3) | 0.078 (9)* | |
C4 | 0.6367 (3) | 0.51791 (16) | 0.1682 (3) | 0.0812 (8) | |
H401 | 0.6195 | 0.5383 | 0.2387 | 0.122* | |
H402 | 0.5645 | 0.4874 | 0.1346 | 0.122* | |
H403 | 0.6394 | 0.5505 | 0.1084 | 0.122* | |
C5 | 0.7735 (3) | 0.43064 (14) | 0.2999 (3) | 0.0864 (9) | |
H501 | 0.7592 | 0.4507 | 0.3718 | 0.130* | |
H502 | 0.8603 | 0.4082 | 0.3203 | 0.130* | |
H503 | 0.7006 | 0.4002 | 0.2678 | 0.130* | |
P1 | 1.06335 (6) | 0.49781 (3) | 0.28039 (5) | 0.0529 (2) | |
O1 | 1.11124 (17) | 0.46577 (8) | 0.39965 (13) | 0.0591 (4) | |
O3 | 1.15910 (18) | 0.55448 (9) | 0.26064 (15) | 0.0683 (5) | |
O2 | 1.05368 (18) | 0.45215 (8) | 0.16681 (14) | 0.0646 (4) | |
C11 | 0.8512 (3) | 0.72463 (11) | 0.4928 (2) | 0.0578 (6) | |
C12 | 0.9622 (3) | 0.75495 (13) | 0.5699 (2) | 0.0671 (6) | |
H12 | 1.0459 | 0.7331 | 0.5954 | 0.081* | |
C13 | 0.9505 (3) | 0.81720 (14) | 0.6095 (3) | 0.0796 (8) | |
H13 | 1.0261 | 0.8373 | 0.6621 | 0.096* | |
C14 | 0.8280 (4) | 0.84991 (14) | 0.5719 (3) | 0.0818 (8) | |
H14 | 0.8202 | 0.8920 | 0.5992 | 0.098* | |
C15 | 0.7168 (4) | 0.82031 (15) | 0.4939 (3) | 0.0885 (9) | |
H15 | 0.6337 | 0.8426 | 0.4680 | 0.106* | |
C16 | 0.7276 (3) | 0.75759 (14) | 0.4537 (3) | 0.0753 (7) | |
H16 | 0.6521 | 0.7377 | 0.4007 | 0.090* | |
C21 | 1.1569 (2) | 0.40546 (12) | 0.1674 (2) | 0.0574 (6) | |
C22 | 1.1438 (3) | 0.34487 (13) | 0.2134 (2) | 0.0692 (7) | |
H22 | 1.0697 | 0.3352 | 0.2448 | 0.083* | |
C23 | 1.2421 (3) | 0.29857 (14) | 0.2122 (3) | 0.0797 (8) | |
H23 | 1.2354 | 0.2574 | 0.2441 | 0.096* | |
C24 | 1.3495 (3) | 0.31283 (15) | 0.1642 (3) | 0.0820 (8) | |
H24 | 1.4157 | 0.2814 | 0.1635 | 0.098* | |
C25 | 1.3600 (3) | 0.37311 (16) | 0.1173 (3) | 0.0808 (8) | |
H25 | 1.4331 | 0.3823 | 0.0842 | 0.097* | |
C26 | 1.2633 (3) | 0.42068 (14) | 0.1184 (3) | 0.0722 (7) | |
H26 | 1.2704 | 0.4618 | 0.0867 | 0.087* | |
C31 | 1.2672 (3) | 0.58269 (14) | 0.3519 (2) | 0.0641 (6) | |
C32 | 1.3957 (3) | 0.55548 (19) | 0.3739 (3) | 0.0919 (10) | |
H32 | 1.4103 | 0.5177 | 0.3340 | 0.110* | |
C33 | 1.5026 (4) | 0.5856 (3) | 0.4568 (4) | 0.1196 (14) | |
H33 | 1.5908 | 0.5681 | 0.4729 | 0.144* | |
C34 | 1.4809 (5) | 0.6406 (3) | 0.5156 (4) | 0.1189 (16) | |
H34 | 1.5539 | 0.6603 | 0.5720 | 0.143* | |
C35 | 1.3517 (5) | 0.66689 (19) | 0.4915 (3) | 0.1088 (13) | |
H35 | 1.3370 | 0.7044 | 0.5318 | 0.131* | |
C36 | 1.2420 (3) | 0.63786 (15) | 0.4070 (3) | 0.0817 (8) | |
H36 | 1.1541 | 0.6558 | 0.3890 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0804 (5) | 0.0627 (4) | 0.0604 (4) | 0.0028 (3) | 0.0182 (3) | 0.0103 (3) |
C1 | 0.0474 (12) | 0.0559 (13) | 0.0545 (12) | 0.0016 (9) | 0.0136 (9) | −0.0002 (9) |
N1 | 0.0887 (16) | 0.0544 (11) | 0.0551 (11) | 0.0083 (11) | 0.0213 (11) | 0.0022 (9) |
N2 | 0.0664 (12) | 0.0554 (11) | 0.0481 (10) | 0.0041 (9) | 0.0193 (9) | 0.0027 (8) |
C2 | 0.0563 (13) | 0.0571 (13) | 0.0478 (12) | 0.0006 (10) | 0.0160 (10) | 0.0016 (9) |
C3 | 0.0577 (14) | 0.0665 (15) | 0.0628 (15) | −0.0020 (11) | 0.0161 (12) | −0.0050 (11) |
C4 | 0.0541 (15) | 0.097 (2) | 0.088 (2) | 0.0010 (14) | 0.0123 (14) | 0.0010 (16) |
C5 | 0.082 (2) | 0.0759 (19) | 0.099 (2) | −0.0190 (16) | 0.0212 (18) | 0.0107 (16) |
P1 | 0.0524 (3) | 0.0619 (4) | 0.0459 (3) | 0.0027 (3) | 0.0157 (2) | 0.0017 (2) |
O1 | 0.0650 (10) | 0.0654 (10) | 0.0476 (8) | 0.0069 (8) | 0.0160 (7) | 0.0063 (7) |
O3 | 0.0593 (10) | 0.0866 (13) | 0.0556 (9) | −0.0138 (9) | 0.0094 (8) | 0.0106 (8) |
O2 | 0.0640 (10) | 0.0774 (11) | 0.0519 (9) | 0.0126 (8) | 0.0148 (8) | −0.0078 (8) |
C11 | 0.0650 (14) | 0.0549 (12) | 0.0554 (13) | 0.0003 (11) | 0.0192 (11) | 0.0004 (10) |
C12 | 0.0598 (15) | 0.0710 (16) | 0.0722 (16) | −0.0049 (12) | 0.0203 (13) | −0.0013 (12) |
C13 | 0.088 (2) | 0.0698 (17) | 0.0796 (18) | −0.0179 (16) | 0.0199 (16) | −0.0075 (14) |
C14 | 0.111 (3) | 0.0598 (15) | 0.0757 (18) | 0.0005 (16) | 0.0271 (17) | −0.0066 (13) |
C15 | 0.090 (2) | 0.0749 (18) | 0.094 (2) | 0.0235 (16) | 0.0128 (18) | −0.0002 (16) |
C16 | 0.0682 (17) | 0.0698 (16) | 0.0795 (17) | 0.0069 (13) | 0.0048 (14) | −0.0033 (13) |
C21 | 0.0579 (13) | 0.0678 (14) | 0.0481 (12) | 0.0056 (11) | 0.0165 (10) | −0.0061 (10) |
C22 | 0.0728 (17) | 0.0751 (17) | 0.0633 (15) | −0.0016 (13) | 0.0243 (13) | −0.0050 (13) |
C23 | 0.102 (2) | 0.0690 (16) | 0.0717 (17) | 0.0128 (16) | 0.0288 (17) | 0.0007 (13) |
C24 | 0.083 (2) | 0.086 (2) | 0.0772 (18) | 0.0238 (16) | 0.0211 (16) | −0.0101 (15) |
C25 | 0.0728 (18) | 0.095 (2) | 0.0848 (19) | 0.0026 (15) | 0.0379 (16) | −0.0168 (16) |
C26 | 0.0775 (18) | 0.0742 (17) | 0.0738 (17) | 0.0000 (14) | 0.0355 (14) | −0.0048 (13) |
C31 | 0.0538 (13) | 0.0806 (17) | 0.0568 (13) | −0.0083 (12) | 0.0131 (11) | 0.0093 (12) |
C32 | 0.0573 (16) | 0.129 (3) | 0.087 (2) | 0.0032 (17) | 0.0150 (15) | −0.0022 (19) |
C33 | 0.0580 (19) | 0.175 (4) | 0.112 (3) | −0.020 (2) | −0.0022 (19) | 0.020 (3) |
C34 | 0.103 (3) | 0.160 (4) | 0.077 (2) | −0.065 (3) | −0.006 (2) | 0.008 (2) |
C35 | 0.134 (4) | 0.099 (2) | 0.089 (2) | −0.044 (3) | 0.022 (2) | −0.0113 (19) |
C36 | 0.0779 (19) | 0.081 (2) | 0.0844 (19) | −0.0084 (15) | 0.0181 (16) | −0.0008 (15) |
S1—C1 | 1.663 (2) | C13—H13 | 0.9300 |
C1—N1 | 1.352 (3) | C14—C15 | 1.372 (4) |
C1—N2 | 1.357 (3) | C14—H14 | 0.9300 |
N1—C11 | 1.425 (3) | C15—C16 | 1.382 (4) |
N1—H1 | 0.85 (3) | C15—H15 | 0.9300 |
N2—C2 | 1.451 (3) | C16—H16 | 0.9300 |
N2—H2 | 0.78 (2) | C21—C26 | 1.368 (3) |
C2—C3 | 1.540 (3) | C21—C22 | 1.371 (4) |
C2—P1 | 1.803 (2) | C22—C23 | 1.375 (4) |
C2—H201 | 0.93 (2) | C22—H22 | 0.9300 |
C3—C4 | 1.518 (4) | C23—C24 | 1.365 (4) |
C3—C5 | 1.521 (4) | C23—H23 | 0.9300 |
C3—H301 | 0.90 (3) | C24—C25 | 1.365 (4) |
C4—H401 | 0.9600 | C24—H24 | 0.9300 |
C4—H402 | 0.9600 | C25—C26 | 1.382 (4) |
C4—H403 | 0.9600 | C25—H25 | 0.9300 |
C5—H501 | 0.9600 | C26—H26 | 0.9300 |
C5—H502 | 0.9600 | C31—C36 | 1.352 (4) |
C5—H503 | 0.9600 | C31—C32 | 1.370 (4) |
P1—O1 | 1.4696 (15) | C32—C33 | 1.374 (5) |
P1—O3 | 1.5656 (17) | C32—H32 | 0.9300 |
P1—O2 | 1.5791 (16) | C33—C34 | 1.361 (6) |
O3—C31 | 1.413 (3) | C33—H33 | 0.9300 |
O2—C21 | 1.413 (3) | C34—C35 | 1.367 (6) |
C11—C12 | 1.373 (3) | C34—H34 | 0.9300 |
C11—C16 | 1.382 (4) | C35—C36 | 1.390 (5) |
C12—C13 | 1.372 (4) | C35—H35 | 0.9300 |
C12—H12 | 0.9300 | C36—H36 | 0.9300 |
C13—C14 | 1.369 (4) | ||
N1—C1—N2 | 112.3 (2) | C14—C13—H13 | 119.9 |
N1—C1—S1 | 123.75 (18) | C12—C13—H13 | 119.9 |
N2—C1—S1 | 123.90 (17) | C13—C14—C15 | 119.8 (3) |
C1—N1—C11 | 126.1 (2) | C13—C14—H14 | 120.1 |
C1—N1—H1 | 113.1 (19) | C15—C14—H14 | 120.1 |
C11—N1—H1 | 120.8 (19) | C14—C15—C16 | 120.4 (3) |
C1—N2—C2 | 125.2 (2) | C14—C15—H15 | 119.8 |
C1—N2—H2 | 112.9 (18) | C16—C15—H15 | 119.8 |
C2—N2—H2 | 121.7 (18) | C11—C16—C15 | 119.6 (3) |
N2—C2—C3 | 113.0 (2) | C11—C16—H16 | 120.2 |
N2—C2—P1 | 106.62 (16) | C15—C16—H16 | 120.2 |
C3—C2—P1 | 115.19 (17) | C26—C21—C22 | 121.9 (2) |
N2—C2—H201 | 107.6 (14) | C26—C21—O2 | 119.8 (2) |
C3—C2—H201 | 110.7 (15) | C22—C21—O2 | 118.3 (2) |
P1—C2—H201 | 103.0 (14) | C21—C22—C23 | 118.9 (3) |
C4—C3—C5 | 110.9 (2) | C21—C22—H22 | 120.5 |
C4—C3—C2 | 109.9 (2) | C23—C22—H22 | 120.5 |
C5—C3—C2 | 113.7 (2) | C24—C23—C22 | 120.2 (3) |
C4—C3—H301 | 112.5 (19) | C24—C23—H23 | 119.9 |
C5—C3—H301 | 109.6 (18) | C22—C23—H23 | 119.9 |
C2—C3—H301 | 99.8 (18) | C25—C24—C23 | 120.2 (3) |
C3—C4—H401 | 109.5 | C25—C24—H24 | 119.9 |
C3—C4—H402 | 109.5 | C23—C24—H24 | 119.9 |
H401—C4—H402 | 109.5 | C24—C25—C26 | 120.8 (3) |
C3—C4—H403 | 109.5 | C24—C25—H25 | 119.6 |
H401—C4—H403 | 109.5 | C26—C25—H25 | 119.6 |
H402—C4—H403 | 109.5 | C21—C26—C25 | 118.1 (3) |
C3—C5—H501 | 109.5 | C21—C26—H26 | 121.0 |
C3—C5—H502 | 109.5 | C25—C26—H26 | 121.0 |
H501—C5—H502 | 109.5 | C36—C31—C32 | 122.8 (3) |
C3—C5—H503 | 109.5 | C36—C31—O3 | 118.8 (2) |
H501—C5—H503 | 109.5 | C32—C31—O3 | 118.2 (3) |
H502—C5—H503 | 109.5 | C31—C32—C33 | 118.1 (4) |
O1—P1—O3 | 113.74 (10) | C31—C32—H32 | 121.0 |
O1—P1—O2 | 115.01 (9) | C33—C32—H32 | 121.0 |
O3—P1—O2 | 103.40 (10) | C34—C33—C32 | 120.9 (4) |
O1—P1—C2 | 116.26 (10) | C34—C33—H33 | 119.6 |
O3—P1—C2 | 105.32 (11) | C32—C33—H33 | 119.6 |
O2—P1—C2 | 101.53 (10) | C33—C34—C35 | 119.9 (4) |
C31—O3—P1 | 125.67 (15) | C33—C34—H34 | 120.1 |
C21—O2—P1 | 120.96 (14) | C35—C34—H34 | 120.1 |
C12—C11—C16 | 119.5 (2) | C34—C35—C36 | 120.4 (4) |
C12—C11—N1 | 119.5 (2) | C34—C35—H35 | 119.8 |
C16—C11—N1 | 120.8 (2) | C36—C35—H35 | 119.8 |
C13—C12—C11 | 120.5 (3) | C31—C36—C35 | 118.0 (3) |
C13—C12—H12 | 119.8 | C31—C36—H36 | 121.0 |
C11—C12—H12 | 119.8 | C35—C36—H36 | 121.0 |
C14—C13—C12 | 120.3 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O1i | 0.85 (3) | 2.16 (3) | 2.975 (3) | 162 (3) |
N2—H2···O1i | 0.78 (3) | 2.17 (3) | 2.932 (3) | 165 (3) |
Symmetry code: (i) −x+2, −y+1, −z+1. |