Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S2053229616020556/fn3226sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H1sup2.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H2sup3.hkl | |
Structure factor file (CIF format) https://doi.org/10.1107/S2053229616020556/fn3226H3sup4.hkl |
CCDC references: 1524668; 1524667; 1524666
For all compounds, data collection: APEX2 (Bruker, 2002); cell refinement: SAINT-Plus (Bruker, 2003); data reduction: SAINT-Plus (Bruker, 2003); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008a). Program(s) used to refine structure: SHELXL2014/7 (Sheldrick, 2015) for H1; SHELXL97 (Sheldrick, 2008a) for H2, H3. For all compounds, molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006). Software used to prepare material for publication: PLATON (Spek, 2009), publCIF (Westrip, 2010) for H1; PLATON (Spek, 2009) for H2, H3.
C12H16N2O2S2 | Dx = 1.315 Mg m−3 |
Mr = 284.39 | Cu Kα radiation, λ = 1.54178 Å |
Orthorhombic, Pna21 | Cell parameters from 9640 reflections |
a = 12.8212 (5) Å | θ = 4.2–70.6° |
b = 10.5085 (4) Å | µ = 3.34 mm−1 |
c = 10.6608 (5) Å | T = 293 K |
V = 1436.35 (10) Å3 | Block, colourless |
Z = 4 | 0.9 × 0.2 × 0.2 mm |
F(000) = 600 |
Bruker SMART APEXII CCD diffractometer | 2688 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.030 |
ω scan | θmax = 70.8°, θmin = 5.4° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2003) | h = −15→14 |
Tmin = 0.347, Tmax = 0.753 | k = −12→12 |
15904 measured reflections | l = −12→12 |
2705 independent reflections |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.029 | w = 1/[σ2(Fo2) + (0.0507P)2 + 0.1855P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.081 | (Δ/σ)max < 0.001 |
S = 1.06 | Δρmax = 0.19 e Å−3 |
2705 reflections | Δρmin = −0.23 e Å−3 |
178 parameters | Absolute structure: Refined as an inversion twin. |
1 restraint | Absolute structure parameter: 0.12 (2) |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
C1 | 0.5649 (2) | 0.0333 (2) | 0.0188 (3) | 0.0463 (5) | |
C4 | 0.51569 (17) | 0.3097 (2) | 0.1828 (2) | 0.0403 (4) | |
C11 | 0.4970 (2) | −0.2228 (3) | 0.0545 (3) | 0.0604 (7) | |
H11 | 0.5238 | −0.2287 | −0.0314 | 0.072* | |
C12 | 0.3955 (3) | −0.2975 (3) | 0.0636 (4) | 0.0775 (9) | |
H12A | 0.4093 | −0.3862 | 0.0496 | 0.116* | |
H12B | 0.3474 | −0.2671 | 0.0015 | 0.116* | |
H12C | 0.3659 | −0.2864 | 0.1456 | 0.116* | |
C13 | 0.5782 (4) | −0.2704 (5) | 0.1436 (6) | 0.1068 (17) | |
H13A | 0.5536 | −0.2610 | 0.2281 | 0.160* | |
H13B | 0.6411 | −0.2222 | 0.1328 | 0.160* | |
H13C | 0.5919 | −0.3586 | 0.1269 | 0.160* | |
C21 | 0.7370 (3) | 0.0840 (4) | −0.1270 (4) | 0.0827 (11) | |
H21A | 0.6954 | 0.1531 | −0.1582 | 0.124* | |
H21B | 0.7833 | 0.0552 | −0.1918 | 0.124* | |
H21C | 0.7769 | 0.1124 | −0.0562 | 0.124* | |
C41 | 0.42548 (18) | 0.3731 (2) | 0.2449 (2) | 0.0399 (5) | |
C42 | 0.4488 (2) | 0.4766 (3) | 0.3224 (3) | 0.0511 (6) | |
H42 | 0.5182 | 0.5000 | 0.3332 | 0.061* | |
C43 | 0.3726 (3) | 0.5448 (3) | 0.3832 (3) | 0.0645 (8) | |
H43 | 0.3904 | 0.6130 | 0.4344 | 0.077* | |
C44 | 0.2698 (3) | 0.5112 (3) | 0.3673 (3) | 0.0642 (7) | |
H44 | 0.2178 | 0.5578 | 0.4070 | 0.077* | |
C45 | 0.2433 (2) | 0.4085 (3) | 0.2928 (3) | 0.0574 (6) | |
H45 | 0.1736 | 0.3860 | 0.2835 | 0.069* | |
C46 | 0.32026 (18) | 0.3383 (2) | 0.2315 (2) | 0.0423 (5) | |
N2 | 0.57494 (15) | 0.15203 (19) | 0.0424 (2) | 0.0490 (5) | |
N3 | 0.49568 (16) | 0.20479 (19) | 0.1147 (2) | 0.0473 (5) | |
H3 | 0.4347 | 0.1708 | 0.1158 | 0.057* | |
O4 | 0.60509 (13) | 0.35168 (18) | 0.1945 (2) | 0.0556 (5) | |
O46 | 0.29514 (12) | 0.23761 (18) | 0.1576 (2) | 0.0534 (4) | |
H46 | 0.2344 | 0.2171 | 0.1705 | 0.080* | |
S1A | 0.4675 (5) | −0.0580 (3) | 0.0899 (4) | 0.0572 (10) | 0.67 (2) |
S1B | 0.4509 (7) | −0.0583 (9) | 0.0534 (19) | 0.080 (3) | 0.33 (2) |
S2 | 0.65384 (6) | −0.04348 (7) | −0.08043 (12) | 0.0631 (2) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0410 (11) | 0.0445 (12) | 0.0535 (13) | 0.0061 (9) | 0.0012 (10) | 0.0015 (10) |
C4 | 0.0360 (10) | 0.0352 (10) | 0.0496 (11) | 0.0000 (8) | −0.0013 (9) | 0.0062 (9) |
C11 | 0.0702 (16) | 0.0436 (13) | 0.0673 (16) | −0.0016 (12) | 0.0036 (14) | −0.0014 (12) |
C12 | 0.083 (2) | 0.0596 (17) | 0.090 (2) | −0.0188 (15) | −0.0050 (19) | 0.0004 (16) |
C13 | 0.082 (3) | 0.096 (3) | 0.142 (4) | −0.007 (2) | −0.020 (3) | 0.047 (3) |
C21 | 0.071 (2) | 0.080 (2) | 0.096 (2) | 0.0040 (18) | 0.0401 (19) | 0.0049 (19) |
C41 | 0.0420 (11) | 0.0339 (10) | 0.0437 (11) | 0.0003 (9) | 0.0003 (9) | 0.0025 (9) |
C42 | 0.0530 (13) | 0.0440 (12) | 0.0561 (13) | −0.0046 (11) | −0.0027 (11) | −0.0032 (11) |
C43 | 0.082 (2) | 0.0513 (15) | 0.0603 (16) | −0.0019 (13) | 0.0036 (14) | −0.0186 (12) |
C44 | 0.0685 (17) | 0.0564 (16) | 0.0676 (16) | 0.0086 (14) | 0.0165 (14) | −0.0155 (13) |
C45 | 0.0448 (13) | 0.0600 (14) | 0.0673 (15) | 0.0041 (12) | 0.0083 (11) | −0.0064 (14) |
C46 | 0.0405 (11) | 0.0391 (11) | 0.0472 (11) | 0.0036 (9) | 0.0020 (9) | −0.0008 (9) |
N2 | 0.0384 (9) | 0.0435 (10) | 0.0649 (12) | 0.0046 (7) | 0.0088 (9) | −0.0023 (9) |
N3 | 0.0338 (9) | 0.0408 (10) | 0.0672 (12) | 0.0003 (7) | 0.0071 (8) | −0.0077 (9) |
O4 | 0.0350 (8) | 0.0511 (10) | 0.0807 (13) | −0.0031 (7) | −0.0003 (8) | −0.0072 (9) |
O46 | 0.0320 (7) | 0.0546 (10) | 0.0736 (10) | 0.0004 (7) | 0.0015 (8) | −0.0186 (9) |
S1A | 0.0505 (16) | 0.0415 (8) | 0.0794 (18) | −0.0032 (9) | 0.0222 (12) | −0.0042 (8) |
S1B | 0.0432 (18) | 0.052 (2) | 0.146 (7) | −0.0021 (11) | −0.010 (3) | −0.022 (3) |
S2 | 0.0638 (4) | 0.0546 (4) | 0.0709 (4) | 0.0131 (3) | 0.0199 (3) | −0.0048 (3) |
C1—N2 | 1.280 (3) | C21—S2 | 1.782 (4) |
C1—S1A | 1.747 (4) | C21—H21A | 0.9600 |
C1—S2 | 1.752 (3) | C21—H21B | 0.9600 |
C1—S1B | 1.789 (9) | C21—H21C | 0.9600 |
C4—O4 | 1.234 (3) | C41—C42 | 1.397 (4) |
C4—N3 | 1.345 (3) | C41—C46 | 1.405 (3) |
C4—C41 | 1.490 (3) | C42—C43 | 1.374 (4) |
C11—C13 | 1.495 (5) | C42—H42 | 0.9300 |
C11—C12 | 1.522 (4) | C43—C44 | 1.375 (5) |
C11—S1A | 1.813 (4) | C43—H43 | 0.9300 |
C11—S1B | 1.827 (10) | C44—C45 | 1.383 (4) |
C11—H11 | 0.9800 | C44—H44 | 0.9300 |
C12—H12A | 0.9600 | C45—C46 | 1.395 (3) |
C12—H12B | 0.9600 | C45—H45 | 0.9300 |
C12—H12C | 0.9600 | C46—O46 | 1.358 (3) |
C13—H13A | 0.9600 | N2—N3 | 1.390 (3) |
C13—H13B | 0.9600 | N3—H3 | 0.8600 |
C13—H13C | 0.9600 | O46—H46 | 0.8200 |
N2—C1—S1A | 121.4 (2) | H21A—C21—H21B | 109.5 |
N2—C1—S2 | 120.2 (2) | S2—C21—H21C | 109.5 |
S1A—C1—S2 | 118.32 (18) | H21A—C21—H21C | 109.5 |
N2—C1—S1B | 124.5 (4) | H21B—C21—H21C | 109.5 |
S2—C1—S1B | 114.1 (4) | C42—C41—C46 | 117.9 (2) |
O4—C4—N3 | 121.6 (2) | C42—C41—C4 | 116.4 (2) |
O4—C4—C41 | 121.1 (2) | C46—C41—C4 | 125.7 (2) |
N3—C4—C41 | 117.29 (19) | C43—C42—C41 | 122.2 (3) |
C13—C11—C12 | 112.4 (3) | C43—C42—H42 | 118.9 |
C13—C11—S1A | 109.4 (4) | C41—C42—H42 | 118.9 |
C12—C11—S1A | 107.6 (3) | C42—C43—C44 | 119.3 (3) |
C13—C11—S1B | 123.1 (6) | C42—C43—H43 | 120.3 |
C12—C11—S1B | 102.2 (3) | C44—C43—H43 | 120.3 |
C13—C11—H11 | 109.1 | C43—C44—C45 | 120.5 (3) |
C12—C11—H11 | 109.1 | C43—C44—H44 | 119.8 |
S1A—C11—H11 | 109.1 | C45—C44—H44 | 119.8 |
C11—C12—H12A | 109.5 | C44—C45—C46 | 120.5 (3) |
C11—C12—H12B | 109.5 | C44—C45—H45 | 119.7 |
H12A—C12—H12B | 109.5 | C46—C45—H45 | 119.7 |
C11—C12—H12C | 109.5 | O46—C46—C45 | 121.1 (2) |
H12A—C12—H12C | 109.5 | O46—C46—C41 | 119.3 (2) |
H12B—C12—H12C | 109.5 | C45—C46—C41 | 119.6 (2) |
C11—C13—H13A | 109.5 | C1—N2—N3 | 115.1 (2) |
C11—C13—H13B | 109.5 | C4—N3—N2 | 119.11 (19) |
H13A—C13—H13B | 109.5 | C4—N3—H3 | 120.4 |
C11—C13—H13C | 109.5 | N2—N3—H3 | 120.4 |
H13A—C13—H13C | 109.5 | C46—O46—H46 | 109.5 |
H13B—C13—H13C | 109.5 | C1—S1A—C11 | 106.6 (2) |
S2—C21—H21A | 109.5 | C1—S1B—C11 | 104.2 (4) |
S2—C21—H21B | 109.5 | C1—S2—C21 | 102.21 (15) |
O4—C4—C41—C42 | −3.8 (3) | S2—C1—N2—N3 | 175.43 (18) |
N3—C4—C41—C42 | 175.6 (2) | S1B—C1—N2—N3 | 8.9 (9) |
O4—C4—C41—C46 | 175.7 (2) | O4—C4—N3—N2 | −8.6 (3) |
N3—C4—C41—C46 | −4.9 (3) | C41—C4—N3—N2 | 172.0 (2) |
C46—C41—C42—C43 | −0.9 (4) | C1—N2—N3—C4 | 155.3 (2) |
C4—C41—C42—C43 | 178.7 (2) | N2—C1—S1A—C11 | −169.2 (3) |
C41—C42—C43—C44 | −0.3 (5) | S2—C1—S1A—C11 | 7.5 (5) |
C42—C43—C44—C45 | 1.1 (5) | C13—C11—S1A—C1 | 81.5 (4) |
C43—C44—C45—C46 | −0.7 (5) | C12—C11—S1A—C1 | −156.1 (3) |
C44—C45—C46—O46 | −179.7 (3) | N2—C1—S1B—C11 | −159.8 (5) |
C44—C45—C46—C41 | −0.5 (4) | S2—C1—S1B—C11 | 32.9 (11) |
C42—C41—C46—O46 | −179.5 (2) | C13—C11—S1B—C1 | 61.1 (12) |
C4—C41—C46—O46 | 1.0 (3) | C12—C11—S1B—C1 | −171.5 (8) |
C42—C41—C46—C45 | 1.2 (4) | N2—C1—S2—C21 | −2.3 (3) |
C4—C41—C46—C45 | −178.3 (2) | S1A—C1—S2—C21 | −179.1 (3) |
S1A—C1—N2—N3 | −7.9 (4) | S1B—C1—S2—C21 | 165.6 (7) |
D—H···A | D—H | H···A | D···A | D—H···A |
O46—H46···O4i | 0.82 | 1.83 | 2.640 (2) | 172 |
N3—H3···O46 | 0.86 | 1.97 | 2.634 (2) | 133 |
C13—H13B···S2 | 0.96 | 2.95 | 3.511 (5) | 118 |
C11—H11···S2 | 0.98 | 2.62 | 3.109 (3) | 111 |
Symmetry code: (i) x−1/2, −y+1/2, z. |
C16H16N2O2S2 | F(000) = 696 |
Mr = 332.43 | Dx = 1.367 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
a = 13.2762 (2) Å | Cell parameters from 9883 reflections |
b = 12.6138 (2) Å | θ = 3.5–70.5° |
c = 10.1742 (2) Å | µ = 3.06 mm−1 |
β = 108.5970 (9)° | T = 293 K |
V = 1614.84 (5) Å3 | Plate, colourless |
Z = 4 | 1.00 × 0.30 × 0.04 mm |
Bruker SMART APEXII CCD diffractometer | 2931 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.040 |
ω scan | θmax = 70.6°, θmin = 3.5° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008b) | h = −16→15 |
Tmin = 0.567, Tmax = 0.753 | k = 0→15 |
32181 measured reflections | l = 0→12 |
3055 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.035 | H-atom parameters constrained |
wR(F2) = 0.104 | w = 1/[σ2(Fo2) + (0.0645P)2 + 0.2643P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.001 |
3055 reflections | Δρmax = 0.31 e Å−3 |
202 parameters | Δρmin = −0.31 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. Statistics for all single and composite reflections ————————————————— Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -35.0 0.0348 6.159 -12.430 0.892 - 1.172 0.829 1181 1063 2 -35.0 0.0341 5.755 - 8.396 0.897 - 1.170 0.763 1390 1287 3 -35.0 0.0369 3.224 - 6.474 0.913 - 1.176 0.915 1316 1216 4 -70.0 0.0557 0.727 - 1.132 0.890 - 1.176 1.117 2139 1912 5 -70.0 0.0401 0.809 - 1.984 0.912 - 1.176 0.971 1841 1641 6 -70.0 0.0337 0.940 - 1.927 0.892 - 1.156 0.780 1787 1562 7 -70.0 0.0352 0.888 - 1.314 0.891 - 1.154 0.745 1949 1821 8 -70.0 0.0305 0.673 - 0.953 0.891 - 1.176 0.711 1961 1835 9 -70.0 0.0375 0.537 - 0.988 0.912 - 1.176 0.810 1868 1723 10 -110.0 0.0545 0.125 - 0.333 0.909 - 1.176 1.018 1865 1564 11 -110.0 0.0416 0.131 - 0.279 0.908 - 1.176 0.859 1833 1582 12 -110.0 0.0349 0.174 - 0.355 0.894 - 1.158 0.747 1874 1557 13 -110.0 0.0341 0.133 - 0.230 0.892 - 1.155 0.708 1850 1634 14 -110.0 0.0344 0.130 - 0.188 0.891 - 1.166 0.686 1796 1639 15 -110.0 0.0367 0.192 - 0.269 0.891 - 1.176 0.687 1840 1648 16 -110.0 0.0425 0.206 - 0.359 0.909 - 1.176 0.815 1810 1587 17 -110.0 0.0512 0.174 - 0.356 0.906 - 1.176 0.993 1849 1581 All scans 0.0374 0.125 -12.430 0.890 - 1.176 0.833 30149 26852 su = K * Sqrt[ sigma2(I) + (g<I>)2 ] where sigma(I) is estimated by SAINT The above statistics are based on all non-rejected data, ignoring reflections without equivalents when estimating R(int) and K. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.25504 (12) | 0.77077 (14) | 0.09649 (17) | 0.0436 (4) | |
C4 | 0.07133 (13) | 0.84530 (13) | 0.26026 (19) | 0.0429 (4) | |
C11 | 0.35229 (19) | 0.59595 (17) | 0.0138 (3) | 0.0677 (6) | |
H11A | 0.3223 | 0.6193 | −0.0816 | 0.081* | |
H11B | 0.4202 | 0.6311 | 0.0540 | 0.081* | |
C12 | 0.36823 (14) | 0.47773 (15) | 0.0178 (2) | 0.0515 (4) | |
C13 | 0.43092 (16) | 0.42485 (19) | 0.1348 (2) | 0.0647 (5) | |
H13 | 0.4615 | 0.4619 | 0.2169 | 0.078* | |
C14 | 0.44807 (18) | 0.3165 (2) | 0.1294 (3) | 0.0775 (7) | |
H14 | 0.4901 | 0.2809 | 0.2077 | 0.093* | |
C15 | 0.40272 (18) | 0.26240 (19) | 0.0079 (3) | 0.0781 (7) | |
H15 | 0.4149 | 0.1901 | 0.0037 | 0.094* | |
C16 | 0.34046 (19) | 0.3136 (2) | −0.1057 (3) | 0.0738 (7) | |
H16 | 0.3095 | 0.2760 | −0.1873 | 0.089* | |
C17 | 0.32243 (16) | 0.42093 (18) | −0.1017 (2) | 0.0608 (5) | |
H17 | 0.2790 | 0.4552 | −0.1804 | 0.073* | |
C21 | 0.2886 (2) | 0.96643 (17) | −0.0016 (3) | 0.0731 (6) | |
H21A | 0.2127 | 0.9687 | −0.0424 | 0.110* | |
H21B | 0.3209 | 1.0073 | −0.0570 | 0.110* | |
H21C | 0.3084 | 0.9954 | 0.0904 | 0.110* | |
C41 | 0.00117 (12) | 0.79433 (13) | 0.33090 (18) | 0.0420 (4) | |
C42 | −0.05349 (15) | 0.86329 (15) | 0.3924 (2) | 0.0519 (4) | |
H42 | −0.0439 | 0.9360 | 0.3872 | 0.062* | |
C43 | −0.12076 (16) | 0.82651 (17) | 0.4602 (2) | 0.0588 (5) | |
H43 | −0.1565 | 0.8738 | 0.4997 | 0.071* | |
C44 | −0.13501 (15) | 0.71880 (16) | 0.4693 (2) | 0.0560 (5) | |
H44 | −0.1802 | 0.6935 | 0.5156 | 0.067* | |
C45 | −0.08279 (14) | 0.64853 (15) | 0.4102 (2) | 0.0492 (4) | |
H45 | −0.0929 | 0.5760 | 0.4169 | 0.059* | |
C46 | −0.01471 (12) | 0.68559 (14) | 0.34047 (17) | 0.0406 (3) | |
N2 | 0.19609 (11) | 0.82948 (11) | 0.14342 (16) | 0.0453 (3) | |
N3 | 0.13186 (10) | 0.78164 (10) | 0.20946 (15) | 0.0430 (3) | |
H3 | 0.1305 | 0.7139 | 0.2179 | 0.052* | |
O4 | 0.07656 (11) | 0.94196 (10) | 0.25163 (16) | 0.0611 (4) | |
O46 | 0.03793 (10) | 0.61603 (9) | 0.28344 (15) | 0.0507 (3) | |
H46 | 0.0089 | 0.5579 | 0.2749 | 0.076* | |
S1 | 0.26284 (4) | 0.63121 (4) | 0.11120 (6) | 0.05753 (17) | |
S2 | 0.33320 (4) | 0.83151 (4) | 0.00634 (6) | 0.05742 (17) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0431 (7) | 0.0463 (9) | 0.0474 (8) | −0.0026 (6) | 0.0229 (7) | −0.0036 (7) |
C4 | 0.0440 (8) | 0.0381 (8) | 0.0516 (9) | 0.0018 (6) | 0.0224 (7) | −0.0021 (7) |
C11 | 0.0753 (13) | 0.0578 (11) | 0.0929 (16) | 0.0068 (10) | 0.0591 (13) | 0.0001 (11) |
C12 | 0.0451 (8) | 0.0518 (10) | 0.0699 (11) | 0.0034 (7) | 0.0358 (8) | 0.0022 (9) |
C13 | 0.0546 (10) | 0.0798 (14) | 0.0619 (12) | −0.0012 (10) | 0.0219 (9) | −0.0037 (10) |
C14 | 0.0601 (12) | 0.0808 (16) | 0.1001 (19) | 0.0161 (11) | 0.0374 (13) | 0.0339 (15) |
C15 | 0.0650 (12) | 0.0520 (12) | 0.138 (2) | −0.0003 (10) | 0.0620 (15) | −0.0053 (14) |
C16 | 0.0639 (12) | 0.0810 (15) | 0.0915 (17) | −0.0113 (12) | 0.0459 (12) | −0.0285 (14) |
C17 | 0.0523 (10) | 0.0783 (14) | 0.0603 (11) | 0.0060 (9) | 0.0298 (9) | 0.0014 (10) |
C21 | 0.0929 (16) | 0.0491 (11) | 0.0975 (17) | −0.0121 (11) | 0.0587 (14) | −0.0036 (11) |
C41 | 0.0400 (8) | 0.0443 (9) | 0.0466 (9) | 0.0020 (6) | 0.0209 (7) | −0.0036 (7) |
C42 | 0.0557 (10) | 0.0449 (9) | 0.0647 (11) | 0.0058 (8) | 0.0327 (9) | −0.0053 (8) |
C43 | 0.0578 (10) | 0.0639 (12) | 0.0671 (12) | 0.0097 (9) | 0.0375 (10) | −0.0080 (10) |
C44 | 0.0492 (9) | 0.0676 (12) | 0.0620 (11) | −0.0025 (8) | 0.0330 (8) | −0.0017 (9) |
C45 | 0.0469 (9) | 0.0513 (9) | 0.0565 (10) | −0.0042 (7) | 0.0266 (8) | −0.0013 (8) |
C46 | 0.0388 (7) | 0.0420 (8) | 0.0456 (9) | 0.0009 (6) | 0.0199 (7) | −0.0025 (7) |
N2 | 0.0464 (7) | 0.0440 (7) | 0.0541 (8) | −0.0035 (6) | 0.0281 (7) | −0.0019 (6) |
N3 | 0.0470 (7) | 0.0351 (7) | 0.0565 (8) | 0.0007 (5) | 0.0302 (6) | −0.0009 (6) |
O4 | 0.0730 (8) | 0.0362 (7) | 0.0923 (10) | 0.0039 (6) | 0.0518 (8) | 0.0013 (6) |
O46 | 0.0561 (7) | 0.0379 (6) | 0.0729 (9) | −0.0018 (5) | 0.0413 (6) | −0.0052 (6) |
S1 | 0.0727 (3) | 0.0465 (3) | 0.0735 (3) | 0.0054 (2) | 0.0517 (3) | 0.0009 (2) |
S2 | 0.0619 (3) | 0.0552 (3) | 0.0717 (3) | −0.0051 (2) | 0.0446 (3) | −0.0011 (2) |
C1—N2 | 1.276 (2) | C17—H17 | 0.9300 |
C1—S2 | 1.7641 (16) | C21—S2 | 1.795 (2) |
C1—S1 | 1.7669 (18) | C21—H21A | 0.9600 |
C4—O4 | 1.226 (2) | C21—H21B | 0.9600 |
C4—N3 | 1.350 (2) | C21—H21C | 0.9600 |
C4—C41 | 1.491 (2) | C41—C46 | 1.396 (2) |
C11—C12 | 1.505 (3) | C41—C42 | 1.402 (2) |
C11—S1 | 1.8276 (19) | C42—C43 | 1.371 (3) |
C11—H11A | 0.9700 | C42—H42 | 0.9300 |
C11—H11B | 0.9700 | C43—C44 | 1.379 (3) |
C12—C17 | 1.375 (3) | C43—H43 | 0.9300 |
C12—C13 | 1.387 (3) | C44—C45 | 1.376 (3) |
C13—C14 | 1.389 (4) | C44—H44 | 0.9300 |
C13—H13 | 0.9300 | C45—C46 | 1.396 (2) |
C14—C15 | 1.372 (4) | C45—H45 | 0.9300 |
C14—H14 | 0.9300 | C46—O46 | 1.3615 (19) |
C15—C16 | 1.352 (4) | N2—N3 | 1.3813 (18) |
C15—H15 | 0.9300 | N3—H3 | 0.8600 |
C16—C17 | 1.378 (3) | O46—H46 | 0.8200 |
C16—H16 | 0.9300 | ||
N2—C1—S2 | 118.38 (13) | S2—C21—H21B | 109.5 |
N2—C1—S1 | 124.96 (13) | H21A—C21—H21B | 109.5 |
S2—C1—S1 | 116.65 (9) | S2—C21—H21C | 109.5 |
O4—C4—N3 | 120.66 (16) | H21A—C21—H21C | 109.5 |
O4—C4—C41 | 121.44 (15) | H21B—C21—H21C | 109.5 |
N3—C4—C41 | 117.87 (14) | C46—C41—C42 | 117.86 (16) |
C12—C11—S1 | 109.67 (14) | C46—C41—C4 | 126.06 (14) |
C12—C11—H11A | 109.7 | C42—C41—C4 | 116.07 (15) |
S1—C11—H11A | 109.7 | C43—C42—C41 | 121.83 (17) |
C12—C11—H11B | 109.7 | C43—C42—H42 | 119.1 |
S1—C11—H11B | 109.7 | C41—C42—H42 | 119.1 |
H11A—C11—H11B | 108.2 | C42—C43—C44 | 119.49 (17) |
C17—C12—C13 | 118.93 (19) | C42—C43—H43 | 120.3 |
C17—C12—C11 | 118.3 (2) | C44—C43—H43 | 120.3 |
C13—C12—C11 | 122.7 (2) | C45—C44—C43 | 120.44 (17) |
C12—C13—C14 | 120.0 (2) | C45—C44—H44 | 119.8 |
C12—C13—H13 | 120.0 | C43—C44—H44 | 119.8 |
C14—C13—H13 | 120.0 | C44—C45—C46 | 120.29 (17) |
C15—C14—C13 | 119.7 (2) | C44—C45—H45 | 119.9 |
C15—C14—H14 | 120.2 | C46—C45—H45 | 119.9 |
C13—C14—H14 | 120.2 | O46—C46—C41 | 119.61 (14) |
C16—C15—C14 | 120.4 (2) | O46—C46—C45 | 120.30 (15) |
C16—C15—H15 | 119.8 | C41—C46—C45 | 120.08 (15) |
C14—C15—H15 | 119.8 | C1—N2—N3 | 118.43 (14) |
C15—C16—C17 | 120.6 (2) | C4—N3—N2 | 117.48 (13) |
C15—C16—H16 | 119.7 | C4—N3—H3 | 121.3 |
C17—C16—H16 | 119.7 | N2—N3—H3 | 121.3 |
C12—C17—C16 | 120.4 (2) | C46—O46—H46 | 109.5 |
C12—C17—H17 | 119.8 | C1—S1—C11 | 103.13 (9) |
C16—C17—H17 | 119.8 | C1—S2—C21 | 101.24 (9) |
S2—C21—H21A | 109.5 | ||
S1—C11—C12—C17 | 108.74 (18) | C43—C44—C45—C46 | 0.0 (3) |
S1—C11—C12—C13 | −74.3 (2) | C42—C41—C46—O46 | −179.22 (17) |
C17—C12—C13—C14 | 1.1 (3) | C4—C41—C46—O46 | 1.0 (3) |
C11—C12—C13—C14 | −175.86 (19) | C42—C41—C46—C45 | −0.3 (3) |
C12—C13—C14—C15 | 0.0 (3) | C4—C41—C46—C45 | 179.87 (16) |
C13—C14—C15—C16 | −0.8 (3) | C44—C45—C46—O46 | 179.23 (17) |
C14—C15—C16—C17 | 0.6 (3) | C44—C45—C46—C41 | 0.3 (3) |
C13—C12—C17—C16 | −1.3 (3) | S2—C1—N2—N3 | 177.60 (12) |
C11—C12—C17—C16 | 175.75 (18) | S1—C1—N2—N3 | −0.9 (2) |
C15—C16—C17—C12 | 0.5 (3) | O4—C4—N3—N2 | −2.4 (3) |
O4—C4—C41—C46 | 176.59 (18) | C41—C4—N3—N2 | 179.59 (14) |
N3—C4—C41—C46 | −5.4 (3) | C1—N2—N3—C4 | 178.99 (16) |
O4—C4—C41—C42 | −3.2 (3) | N2—C1—S1—C11 | 176.14 (17) |
N3—C4—C41—C42 | 174.76 (17) | S2—C1—S1—C11 | −2.39 (14) |
C46—C41—C42—C43 | 0.0 (3) | C12—C11—S1—C1 | 179.41 (16) |
C4—C41—C42—C43 | 179.77 (18) | N2—C1—S2—C21 | −5.47 (17) |
C41—C42—C43—C44 | 0.4 (3) | S1—C1—S2—C21 | 173.16 (12) |
C42—C43—C44—C45 | −0.4 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
O46—H46···O4i | 0.82 | 1.82 | 2.6293 (17) | 170 |
N3—H3···O46 | 0.86 | 2.00 | 2.6616 (17) | 133 |
C45—H45···O4i | 0.93 | 2.47 | 3.098 (2) | 125 |
C21—H21A···O46ii | 0.96 | 2.65 | 3.507 (3) | 148 |
Symmetry codes: (i) −x, y−1/2, −z+1/2; (ii) x, −y+3/2, z−1/2. |
C22H20N2O2S2·C3H8O | Z = 2 |
Mr = 468.61 | F(000) = 496 |
Triclinic, P1 | Dx = 1.309 Mg m−3 |
a = 8.7950 (18) Å | Cu Kα radiation, λ = 1.54178 Å |
b = 10.254 (2) Å | Cell parameters from 9800 reflections |
c = 14.044 (3) Å | θ = 3.4–72.3° |
α = 74.95 (3)° | µ = 2.26 mm−1 |
β = 76.74 (3)° | T = 100 K |
γ = 88.99 (3)° | Block, colourless |
V = 1189.3 (5) Å3 | 0.42 × 0.18 × 0.16 mm |
Bruker SMART APEXII CCD diffractometer | 4606 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.036 |
ω scan | θmax = 72.6°, θmin = 3.4° |
Absorption correction: multi-scan (TWINABS; Sheldrick, 2008b) | h = −10→10 |
Tmin = 0.450, Tmax = 0.713 | k = −12→12 |
33855 measured reflections | l = 0→17 |
4709 independent reflections |
Refinement on F2 | 0 restraints |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.033 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.128 | w = 1/[σ2(Fo2) + (0.067P)2] where P = (Fo2 + 2Fc2)/3 |
S = 1.76 | (Δ/σ)max < 0.001 |
4709 reflections | Δρmax = 0.39 e Å−3 |
301 parameters | Δρmin = −0.44 e Å−3 |
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. Statistics for all single and composite reflections ————————————————— Scan 2-theta R(int) Incid. factors Diffr. factors K Total I>2sig(I) 1 -119.0 0.0166 0.494 - 0.736 0.937 - 1.189 0.987 1442 1344 2 -119.0 0.0202 0.364 - 0.591 0.935 - 1.211 0.946 1637 1557 3 -119.0 0.0258 0.479 - 0.953 0.952 - 1.211 1.058 1234 1145 4 -119.0 0.0213 0.233 - 0.404 0.954 - 1.210 0.967 1531 1428 5 -119.0 0.0173 0.453 - 0.638 0.935 - 1.210 0.838 1646 1559 6 -119.0 0.0192 0.395 - 0.556 0.936 - 1.147 0.865 1679 1606 7 -119.0 0.0174 0.915 - 1.501 0.937 - 1.075 0.784 1618 1547 8 -119.0 0.0233 0.678 - 1.014 0.937 - 1.054 1.154 1269 1177 9 -70.0 0.0180 1.336 - 1.977 0.936 - 1.130 0.871 1755 1699 10 -70.0 0.0189 0.857 - 1.221 0.935 - 1.211 0.829 1760 1698 11 -70.0 0.0303 1.148 - 2.413 0.953 - 1.207 1.212 1511 1443 12 -70.0 0.0207 1.435 - 2.472 0.942 - 1.211 0.896 1820 1746 13 -70.0 0.0180 1.940 - 2.783 0.935 - 1.181 0.802 1837 1777 14 -70.0 0.0201 1.290 - 2.166 0.936 - 1.067 0.875 1727 1658 15 -35.0 0.0233 4.074 - 7.577 0.937 - 1.207 1.079 1014 987 16 -35.0 0.0207 4.757 - 7.034 0.935 - 1.210 1.005 1097 1065 17 -35.0 0.0302 4.825 - 8.043 0.936 - 1.054 1.196 973 929 18 -118.1 0.0224 0.212 - 0.402 0.936 - 1.209 0.821 1715 1558 19 -59.8 0.0277 1.473 - 1.994 0.953 - 1.129 1.144 304 281 20 -116.1 0.0256 0.232 - 0.593 0.937 - 1.087 0.906 1253 1140 21 -113.2 0.0221 1.047 - 1.272 0.952 - 1.120 0.879 816 764 22 -114.1 0.0269 0.208 - 0.238 0.946 - 1.127 0.929 325 309 23 -114.9 0.0289 0.400 - 0.449 0.972 - 1.035 1.128 205 187 24 -117.7 0.0201 0.218 - 0.243 0.958 - 1.124 0.866 291 268 25 -115.8 0.0215 0.271 - 0.602 0.937 - 1.210 0.812 1733 1586 26 -117.3 0.0274 0.402 - 0.519 0.952 - 1.208 0.953 1377 1246 All scans 0.0222 0.208 - 8.043 0.935 - 1.211 0.954 33569 31704 su = K * Sqrt[ sigma2(I) + (g<I>)2 ] where sigma(I) is estimated by SAINT The above statistics are based on all non-rejected data, ignoring reflections without equivalents when estimating R(int) and K. |
x | y | z | Uiso*/Ueq | ||
C1 | 0.61659 (12) | 0.39221 (11) | 0.05969 (8) | 0.0146 (2) | |
C4 | 0.86236 (12) | 0.67654 (11) | 0.01322 (8) | 0.0147 (2) | |
C11 | 0.55672 (13) | 0.19784 (11) | −0.04122 (9) | 0.0197 (2) | |
H11A | 0.5672 | 0.1254 | 0.0168 | 0.024* | |
H11B | 0.4481 | 0.2217 | −0.0320 | 0.024* | |
C12 | 0.60978 (13) | 0.15447 (11) | −0.13763 (9) | 0.0188 (2) | |
C13 | 0.71955 (13) | 0.05532 (12) | −0.14395 (10) | 0.0215 (3) | |
H13 | 0.7598 | 0.0153 | −0.0881 | 0.026* | |
C14 | 0.76892 (15) | 0.01612 (12) | −0.23306 (11) | 0.0266 (3) | |
H14 | 0.8414 | −0.0507 | −0.2365 | 0.032* | |
C15 | 0.71063 (15) | 0.07613 (13) | −0.31702 (10) | 0.0280 (3) | |
H15 | 0.7433 | 0.0495 | −0.3767 | 0.034* | |
C16 | 0.60296 (16) | 0.17648 (14) | −0.31150 (10) | 0.0291 (3) | |
H16 | 0.5647 | 0.2179 | −0.3680 | 0.035* | |
C17 | 0.55240 (14) | 0.21501 (12) | −0.22227 (10) | 0.0234 (3) | |
H17 | 0.4798 | 0.2817 | −0.2190 | 0.028* | |
C21 | 0.44409 (13) | 0.37663 (12) | 0.25297 (8) | 0.0192 (2) | |
H21A | 0.5469 | 0.3951 | 0.2620 | 0.023* | |
H21B | 0.3933 | 0.4616 | 0.2368 | 0.023* | |
C22 | 0.34803 (13) | 0.28278 (11) | 0.34891 (8) | 0.0171 (2) | |
C23 | 0.18674 (14) | 0.26791 (12) | 0.36483 (9) | 0.0205 (3) | |
H23 | 0.1369 | 0.3153 | 0.3155 | 0.025* | |
C24 | 0.09904 (14) | 0.18268 (13) | 0.45403 (10) | 0.0235 (3) | |
H24 | −0.0089 | 0.1739 | 0.4640 | 0.028* | |
C25 | 0.17187 (15) | 0.11060 (13) | 0.52820 (9) | 0.0239 (3) | |
H25 | 0.1132 | 0.0539 | 0.5878 | 0.029* | |
C26 | 0.33288 (15) | 0.12425 (13) | 0.51229 (9) | 0.0259 (3) | |
H26 | 0.3828 | 0.0760 | 0.5613 | 0.031* | |
C27 | 0.42005 (14) | 0.20971 (13) | 0.42336 (9) | 0.0230 (3) | |
H27 | 0.5280 | 0.2182 | 0.4135 | 0.028* | |
C41 | 0.99012 (12) | 0.75110 (11) | −0.07271 (8) | 0.0149 (2) | |
C42 | 1.05129 (14) | 0.86971 (11) | −0.06127 (9) | 0.0183 (2) | |
H42 | 1.0104 | 0.8965 | −0.0025 | 0.022* | |
C43 | 1.17093 (14) | 0.94877 (12) | −0.13473 (9) | 0.0216 (3) | |
H43 | 1.2091 | 1.0277 | −0.1258 | 0.026* | |
C44 | 1.23235 (14) | 0.90747 (12) | −0.22188 (9) | 0.0221 (3) | |
H44 | 1.3136 | 0.9586 | −0.2714 | 0.027* | |
C45 | 1.17411 (14) | 0.79116 (12) | −0.23601 (9) | 0.0208 (3) | |
H45 | 1.2153 | 0.7658 | −0.2954 | 0.025* | |
C46 | 1.05370 (12) | 0.71125 (11) | −0.16160 (8) | 0.0156 (2) | |
C1P | 0.7824 (2) | 0.50546 (17) | 0.44335 (11) | 0.0403 (4) | |
H1P1 | 0.6743 | 0.4758 | 0.4611 | 0.060* | |
H1P2 | 0.8023 | 0.5501 | 0.4918 | 0.060* | |
H1P3 | 0.8467 | 0.4288 | 0.4436 | 0.060* | |
C2P | 0.82029 (15) | 0.60256 (13) | 0.33882 (9) | 0.0234 (3) | |
H2P | 0.7533 | 0.6799 | 0.3392 | 0.028* | |
C3P | 0.98957 (17) | 0.65390 (17) | 0.30445 (13) | 0.0402 (4) | |
H3P1 | 1.0563 | 0.5787 | 0.3055 | 0.060* | |
H3P2 | 1.0116 | 0.7038 | 0.3492 | 0.060* | |
H3P3 | 1.0082 | 0.7118 | 0.2368 | 0.060* | |
N2 | 0.67780 (10) | 0.49282 (10) | 0.07869 (7) | 0.0158 (2) | |
N3 | 0.80167 (11) | 0.56226 (10) | 0.00335 (7) | 0.0148 (2) | |
H3 | 0.8374 (17) | 0.5377 (15) | −0.0493 (12) | 0.018* | |
O4 | 0.81506 (10) | 0.71966 (8) | 0.08894 (6) | 0.0207 (2) | |
O46 | 0.99837 (10) | 0.59585 (9) | −0.17513 (6) | 0.0180 (2) | |
H46 | 1.060 (2) | 0.5647 (18) | −0.2088 (13) | 0.027* | |
O3P | 0.78273 (10) | 0.53109 (8) | 0.27046 (6) | 0.0208 (2) | |
H3P | 0.779 (2) | 0.5940 (18) | 0.2162 (13) | 0.031* | |
S1 | 0.68242 (3) | 0.34452 (3) | −0.05435 (2) | 0.01616 (13) | |
S2 | 0.46135 (3) | 0.29405 (3) | 0.15092 (2) | 0.01668 (13) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0163 (5) | 0.0142 (5) | 0.0125 (5) | 0.0008 (4) | −0.0019 (4) | −0.0034 (4) |
C4 | 0.0165 (5) | 0.0135 (5) | 0.0148 (5) | 0.0022 (4) | −0.0045 (4) | −0.0041 (4) |
C11 | 0.0217 (5) | 0.0179 (5) | 0.0201 (6) | −0.0049 (4) | −0.0011 (4) | −0.0089 (4) |
C12 | 0.0185 (5) | 0.0177 (5) | 0.0207 (6) | −0.0044 (4) | −0.0006 (4) | −0.0090 (4) |
C13 | 0.0225 (6) | 0.0170 (6) | 0.0251 (6) | −0.0025 (4) | −0.0031 (5) | −0.0073 (5) |
C14 | 0.0260 (6) | 0.0201 (6) | 0.0329 (7) | −0.0017 (5) | 0.0021 (5) | −0.0132 (5) |
C15 | 0.0326 (7) | 0.0289 (7) | 0.0235 (6) | −0.0082 (5) | 0.0032 (5) | −0.0168 (5) |
C16 | 0.0330 (6) | 0.0347 (7) | 0.0224 (6) | −0.0033 (5) | −0.0083 (5) | −0.0108 (5) |
C17 | 0.0241 (6) | 0.0235 (6) | 0.0245 (6) | −0.0001 (5) | −0.0057 (5) | −0.0096 (5) |
C21 | 0.0250 (6) | 0.0183 (6) | 0.0139 (5) | −0.0036 (4) | −0.0017 (4) | −0.0055 (4) |
C22 | 0.0231 (6) | 0.0161 (5) | 0.0126 (5) | −0.0005 (4) | −0.0021 (4) | −0.0062 (4) |
C23 | 0.0224 (6) | 0.0204 (6) | 0.0200 (6) | 0.0012 (4) | −0.0050 (5) | −0.0075 (5) |
C24 | 0.0208 (5) | 0.0243 (6) | 0.0249 (6) | −0.0025 (4) | −0.0008 (5) | −0.0095 (5) |
C25 | 0.0302 (6) | 0.0228 (6) | 0.0152 (5) | −0.0046 (5) | 0.0033 (5) | −0.0059 (4) |
C26 | 0.0318 (6) | 0.0290 (7) | 0.0150 (5) | 0.0012 (5) | −0.0055 (5) | −0.0025 (5) |
C27 | 0.0211 (5) | 0.0296 (6) | 0.0171 (6) | 0.0005 (5) | −0.0031 (4) | −0.0051 (5) |
C41 | 0.0159 (5) | 0.0143 (5) | 0.0142 (5) | 0.0028 (4) | −0.0032 (4) | −0.0036 (4) |
C42 | 0.0223 (5) | 0.0144 (5) | 0.0181 (5) | 0.0019 (4) | −0.0036 (4) | −0.0053 (4) |
C43 | 0.0256 (6) | 0.0143 (5) | 0.0230 (6) | −0.0027 (4) | −0.0050 (5) | −0.0021 (4) |
C44 | 0.0229 (5) | 0.0204 (6) | 0.0179 (5) | −0.0024 (4) | −0.0013 (4) | 0.0009 (4) |
C45 | 0.0225 (5) | 0.0234 (6) | 0.0145 (5) | 0.0021 (4) | −0.0017 (4) | −0.0037 (4) |
C46 | 0.0166 (5) | 0.0156 (5) | 0.0152 (5) | 0.0029 (4) | −0.0046 (4) | −0.0045 (4) |
C1P | 0.0569 (9) | 0.0450 (9) | 0.0208 (7) | −0.0048 (7) | −0.0077 (6) | −0.0126 (6) |
C2P | 0.0266 (6) | 0.0253 (6) | 0.0220 (6) | 0.0013 (5) | −0.0034 (5) | −0.0149 (5) |
C3P | 0.0331 (7) | 0.0464 (9) | 0.0482 (9) | −0.0101 (6) | −0.0032 (6) | −0.0297 (8) |
N2 | 0.0165 (4) | 0.0175 (5) | 0.0126 (4) | −0.0007 (4) | −0.0016 (4) | −0.0036 (4) |
N3 | 0.0168 (4) | 0.0164 (5) | 0.0109 (4) | −0.0007 (3) | −0.0002 (3) | −0.0058 (4) |
O4 | 0.0247 (4) | 0.0181 (4) | 0.0186 (4) | −0.0021 (3) | 0.0019 (3) | −0.0097 (3) |
O46 | 0.0193 (4) | 0.0200 (4) | 0.0160 (4) | 0.0000 (3) | −0.0009 (3) | −0.0098 (3) |
O3P | 0.0246 (4) | 0.0219 (4) | 0.0181 (4) | 0.0007 (3) | −0.0041 (3) | −0.0097 (3) |
S1 | 0.0189 (2) | 0.01553 (19) | 0.01400 (19) | −0.00217 (12) | −0.00015 (13) | −0.00674 (13) |
S2 | 0.0191 (2) | 0.0174 (2) | 0.01252 (19) | −0.00410 (12) | −0.00066 (12) | −0.00447 (14) |
C1—N2 | 1.2860 (15) | C22—C23 | 1.3892 (16) |
C1—S2 | 1.7592 (13) | C23—C24 | 1.3928 (18) |
C1—S1 | 1.7637 (12) | C24—C25 | 1.3897 (18) |
C4—O4 | 1.2386 (15) | C25—C26 | 1.3858 (18) |
C4—N3 | 1.3483 (16) | C26—C27 | 1.3898 (18) |
C4—C41 | 1.4941 (16) | C41—C42 | 1.3995 (17) |
C11—C12 | 1.5048 (16) | C41—C46 | 1.4053 (16) |
C11—S1 | 1.8274 (13) | C42—C43 | 1.3879 (18) |
C12—C17 | 1.3906 (17) | C43—C44 | 1.3882 (18) |
C12—C13 | 1.3953 (17) | C44—C45 | 1.3838 (18) |
C13—C14 | 1.3864 (19) | C45—C46 | 1.4011 (17) |
C14—C15 | 1.386 (2) | C46—O46 | 1.3611 (15) |
C15—C16 | 1.391 (2) | C1P—C2P | 1.5118 (19) |
C16—C17 | 1.3855 (19) | C2P—O3P | 1.4446 (15) |
C21—C22 | 1.5127 (16) | C2P—C3P | 1.5142 (19) |
C21—S2 | 1.8222 (13) | N2—N3 | 1.3858 (14) |
C22—C27 | 1.3914 (16) | ||
N2—C1—S2 | 119.61 (9) | C24—C25—C26 | 119.22 (11) |
N2—C1—S1 | 123.13 (9) | C25—C26—C27 | 120.24 (11) |
S2—C1—S1 | 117.26 (7) | C26—C27—C22 | 120.92 (11) |
O4—C4—N3 | 122.43 (10) | C42—C41—C46 | 118.33 (11) |
O4—C4—C41 | 120.81 (11) | C42—C41—C4 | 115.95 (10) |
N3—C4—C41 | 116.76 (10) | C46—C41—C4 | 125.71 (11) |
C12—C11—S1 | 106.26 (8) | C43—C42—C41 | 122.23 (11) |
C17—C12—C13 | 119.20 (11) | C42—C43—C44 | 118.53 (12) |
C17—C12—C11 | 120.28 (11) | C45—C44—C43 | 120.80 (11) |
C13—C12—C11 | 120.50 (11) | C44—C45—C46 | 120.57 (11) |
C14—C13—C12 | 120.38 (12) | O46—C46—C45 | 120.38 (11) |
C15—C14—C13 | 120.20 (12) | O46—C46—C41 | 120.10 (10) |
C14—C15—C16 | 119.59 (12) | C45—C46—C41 | 119.52 (11) |
C17—C16—C15 | 120.32 (12) | O3P—C2P—C1P | 106.73 (11) |
C16—C17—C12 | 120.30 (11) | O3P—C2P—C3P | 110.53 (11) |
C22—C21—S2 | 107.91 (8) | C1P—C2P—C3P | 112.98 (13) |
C27—C22—C23 | 118.63 (11) | C1—N2—N3 | 115.49 (10) |
C27—C22—C21 | 120.38 (11) | C4—N3—N2 | 119.04 (10) |
C23—C22—C21 | 120.98 (10) | C1—S1—C11 | 104.87 (6) |
C22—C23—C24 | 120.57 (11) | C1—S2—C21 | 100.55 (6) |
C25—C24—C23 | 120.41 (12) |
D—H···A | D—H | H···A | D···A | D—H···A |
O3P—H3P···O4 | 0.867 (17) | 1.874 (17) | 2.7285 (16) | 167.8 (16) |
O46—H46···O3Pi | 0.759 (18) | 1.862 (18) | 2.6131 (14) | 170.1 (17) |
N3—H3···S1 | 0.835 (16) | 2.449 (15) | 2.8554 (13) | 110.9 (12) |
N3—H3···O46 | 0.835 (16) | 1.953 (15) | 2.6416 (16) | 139.1 (14) |
C21—H21B···S1ii | 0.97 | 3.01 | 3.7899 (17) | 139 |
C21—H21A···O3P | 0.97 | 2.56 | 3.4847 (17) | 159 |
C11—H11B···O4ii | 0.97 | 2.63 | 3.5313 (17) | 155 |
Symmetry codes: (i) −x+2, −y+1, −z; (ii) −x+1, −y+1, −z. |