Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805040365/sj6177sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805040365/sj6177Isup2.hkl |
CCDC reference: 296664
All H atoms were fixed geometrically and treated as riding, with C—H distances = 0.96–0.98 Å and N—H distances = 0.86 Å. Uiso(H)=1.2Ueq(C) [For the methyl H atoms Uiso(H)=1.5Ueq(C)] and Uiso(H)=1.2Ueq(N).
Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 1997); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
C15H23N3O9S | F(000) = 888 |
Mr = 421.42 | Dx = 1.369 Mg m−3 |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 3602 reflections |
a = 7.5445 (11) Å | θ = 2.4–22.3° |
b = 8.6792 (13) Å | µ = 0.21 mm−1 |
c = 31.229 (5) Å | T = 293 K |
V = 2044.9 (5) Å3 | Needle, colourless |
Z = 4 | 0.30 × 0.14 × 0.11 mm |
Simens SMART CCD area-detector diffractometer | 4041 independent reflections |
Radiation source: fine-focus sealed tube | 3407 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 8.33 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −9→9 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −7→10 |
Tmin = 0.940, Tmax = 0.977 | l = −37→38 |
11659 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.127 | w = 1/[σ2(Fo2) + (0.0739P)2 + 0.2979P] where P = (Fo2 + 2Fc2)/3 |
S = 1.02 | (Δ/σ)max < 0.001 |
4041 reflections | Δρmax = 0.22 e Å−3 |
263 parameters | Δρmin = −0.25 e Å−3 |
0 restraints | Absolute structure: Flack (1983), 1690 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.03 (12) |
C15H23N3O9S | V = 2044.9 (5) Å3 |
Mr = 421.42 | Z = 4 |
Orthorhombic, P212121 | Mo Kα radiation |
a = 7.5445 (11) Å | µ = 0.21 mm−1 |
b = 8.6792 (13) Å | T = 293 K |
c = 31.229 (5) Å | 0.30 × 0.14 × 0.11 mm |
Simens SMART CCD area-detector diffractometer | 4041 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | 3407 reflections with I > 2σ(I) |
Tmin = 0.940, Tmax = 0.977 | Rint = 0.024 |
11659 measured reflections |
R[F2 > 2σ(F2)] = 0.047 | H-atom parameters constrained |
wR(F2) = 0.127 | Δρmax = 0.22 e Å−3 |
S = 1.02 | Δρmin = −0.25 e Å−3 |
4041 reflections | Absolute structure: Flack (1983), 1690 Friedel pairs |
263 parameters | Absolute structure parameter: 0.03 (12) |
0 restraints |
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 | Occ. (<1) | |
S1 | 0.31442 (12) | 0.74323 (11) | 0.22479 (3) | 0.0739 (3) | |
O1 | 0.2707 (2) | 0.37388 (19) | 0.17692 (5) | 0.0434 (4) | |
O2 | −0.1450 (3) | 0.1768 (3) | 0.17125 (7) | 0.0624 (6) | |
O3 | −0.1156 (4) | −0.0515 (3) | 0.20197 (12) | 0.1051 (10) | |
O4 | 0.2116 (2) | 0.14298 (18) | 0.11188 (6) | 0.0455 (4) | |
O5A | −0.0234 (19) | 0.0254 (18) | 0.0862 (18) | 0.078 (7) | 0.32 (6) |
O5B | 0.023 (3) | 0.0456 (16) | 0.0633 (10) | 0.100 (7) | 0.68 (6) |
O6 | 0.2609 (2) | 0.3429 (2) | 0.04584 (5) | 0.0470 (4) | |
O7 | 0.0654 (4) | 0.4995 (4) | 0.01537 (8) | 0.1018 (10) | |
O8 | 0.4767 (2) | 0.56774 (19) | 0.08519 (6) | 0.0444 (4) | |
O9 | 0.7509 (3) | 0.4849 (3) | 0.10133 (7) | 0.0616 (5) | |
N1 | 0.5056 (3) | 0.5449 (3) | 0.17836 (7) | 0.0477 (5) | |
H1A | 0.6066 | 0.5061 | 0.1715 | 0.057* | |
N2 | 0.6524 (3) | 0.6699 (3) | 0.23097 (7) | 0.0568 (6) | |
H2A | 0.6550 | 0.7271 | 0.2534 | 0.068* | |
N3 | 0.8091 (4) | 0.6027 (3) | 0.21635 (8) | 0.0613 (7) | |
H3A | 0.8079 | 0.5453 | 0.1939 | 0.074* | |
H3B | 0.9069 | 0.6188 | 0.2298 | 0.074* | |
C1 | 0.3539 (3) | 0.4987 (3) | 0.15507 (8) | 0.0409 (6) | |
H1B | 0.2709 | 0.5854 | 0.1535 | 0.049* | |
C2 | 0.3979 (3) | 0.4443 (3) | 0.10951 (8) | 0.0372 (5) | |
H2B | 0.4766 | 0.3545 | 0.1102 | 0.045* | |
C3 | 0.2238 (3) | 0.4047 (3) | 0.08758 (7) | 0.0390 (6) | |
H3C | 0.1531 | 0.4988 | 0.0845 | 0.047* | |
C4 | 0.1188 (3) | 0.2877 (3) | 0.11283 (8) | 0.0379 (5) | |
H4A | 0.0010 | 0.2753 | 0.1001 | 0.045* | |
C5 | 0.1008 (3) | 0.3405 (3) | 0.15916 (8) | 0.0419 (6) | |
H5A | 0.0266 | 0.4331 | 0.1603 | 0.050* | |
C6 | 0.0242 (4) | 0.2193 (4) | 0.18814 (9) | 0.0541 (7) | |
H6A | 0.1017 | 0.1302 | 0.1891 | 0.065* | |
H6B | 0.0112 | 0.2595 | 0.2170 | 0.065* | |
C7 | −0.1999 (5) | 0.0364 (4) | 0.17996 (12) | 0.0731 (9) | |
C8 | −0.3802 (6) | 0.0061 (6) | 0.16217 (16) | 0.1152 (18) | |
H8A | −0.4149 | −0.0976 | 0.1688 | 0.173* | |
H8B | −0.3782 | 0.0195 | 0.1317 | 0.173* | |
H8C | −0.4634 | 0.0768 | 0.1746 | 0.173* | |
C9 | 0.1405 (5) | 0.0281 (4) | 0.08892 (13) | 0.0723 (10) | |
C10 | 0.2534 (6) | −0.1120 (4) | 0.09034 (17) | 0.1056 (17) | |
H10A | 0.1999 | −0.1918 | 0.0734 | 0.158* | |
H10B | 0.2646 | −0.1464 | 0.1194 | 0.158* | |
H10C | 0.3687 | −0.0884 | 0.0791 | 0.158* | |
C11 | 0.1620 (4) | 0.3929 (4) | 0.01282 (9) | 0.0533 (7) | |
C12 | 0.1868 (5) | 0.2940 (5) | −0.02565 (9) | 0.0753 (10) | |
H12A | 0.1159 | 0.3331 | −0.0488 | 0.113* | |
H12B | 0.1511 | 0.1905 | −0.0191 | 0.113* | |
H12C | 0.3094 | 0.2948 | −0.0339 | 0.113* | |
C13 | 0.6576 (4) | 0.5724 (3) | 0.08259 (9) | 0.0482 (6) | |
C14 | 0.7158 (5) | 0.6992 (4) | 0.05388 (13) | 0.0801 (11) | |
H14A | 0.8429 | 0.7004 | 0.0523 | 0.120* | |
H14B | 0.6744 | 0.7959 | 0.0650 | 0.120* | |
H14C | 0.6676 | 0.6833 | 0.0258 | 0.120* | |
C15 | 0.4988 (4) | 0.6473 (3) | 0.21088 (8) | 0.0497 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0666 (5) | 0.0749 (6) | 0.0802 (6) | −0.0066 (5) | 0.0207 (4) | −0.0332 (5) |
O1 | 0.0424 (9) | 0.0477 (10) | 0.0400 (9) | −0.0079 (8) | −0.0049 (7) | 0.0031 (7) |
O2 | 0.0496 (11) | 0.0709 (13) | 0.0668 (12) | −0.0188 (10) | −0.0058 (9) | 0.0268 (11) |
O3 | 0.0782 (18) | 0.0683 (17) | 0.169 (3) | −0.0155 (14) | −0.0136 (18) | 0.0364 (19) |
O4 | 0.0448 (10) | 0.0320 (9) | 0.0596 (10) | 0.0033 (8) | −0.0109 (8) | −0.0014 (8) |
O5A | 0.056 (6) | 0.058 (5) | 0.119 (18) | −0.013 (5) | −0.017 (7) | −0.038 (7) |
O5B | 0.092 (8) | 0.074 (4) | 0.133 (12) | 0.025 (4) | −0.062 (9) | −0.049 (6) |
O6 | 0.0515 (10) | 0.0506 (10) | 0.0389 (9) | 0.0057 (9) | −0.0021 (8) | −0.0069 (8) |
O7 | 0.112 (2) | 0.137 (2) | 0.0563 (13) | 0.066 (2) | −0.0145 (13) | 0.0068 (15) |
O8 | 0.0417 (10) | 0.0378 (9) | 0.0536 (10) | −0.0003 (8) | 0.0025 (8) | 0.0047 (8) |
O9 | 0.0424 (10) | 0.0682 (13) | 0.0742 (13) | 0.0098 (10) | 0.0014 (9) | 0.0058 (11) |
N1 | 0.0449 (11) | 0.0525 (13) | 0.0459 (12) | −0.0054 (10) | 0.0002 (9) | −0.0154 (10) |
N2 | 0.0677 (16) | 0.0561 (14) | 0.0467 (12) | −0.0144 (13) | −0.0027 (11) | −0.0182 (11) |
N3 | 0.0596 (14) | 0.0679 (16) | 0.0563 (14) | −0.0044 (13) | −0.0109 (12) | −0.0225 (12) |
C1 | 0.0410 (13) | 0.0370 (13) | 0.0446 (13) | −0.0025 (11) | 0.0006 (10) | −0.0039 (10) |
C2 | 0.0380 (12) | 0.0318 (12) | 0.0417 (12) | 0.0016 (10) | 0.0010 (10) | −0.0001 (10) |
C3 | 0.0451 (14) | 0.0343 (12) | 0.0376 (12) | 0.0065 (10) | −0.0034 (10) | −0.0042 (9) |
C4 | 0.0347 (11) | 0.0348 (13) | 0.0441 (12) | 0.0031 (9) | −0.0071 (10) | 0.0003 (10) |
C5 | 0.0384 (12) | 0.0427 (14) | 0.0446 (13) | −0.0009 (11) | −0.0006 (10) | 0.0008 (11) |
C6 | 0.0491 (15) | 0.0623 (18) | 0.0510 (15) | −0.0115 (14) | −0.0054 (12) | 0.0135 (13) |
C7 | 0.0617 (19) | 0.071 (2) | 0.087 (2) | −0.0219 (18) | −0.0004 (18) | 0.0176 (19) |
C8 | 0.089 (3) | 0.122 (4) | 0.135 (4) | −0.055 (3) | −0.041 (3) | 0.036 (3) |
C9 | 0.068 (2) | 0.0428 (16) | 0.106 (3) | 0.0037 (15) | −0.032 (2) | −0.0128 (17) |
C10 | 0.102 (3) | 0.0494 (19) | 0.166 (5) | 0.024 (2) | −0.045 (3) | −0.033 (2) |
C11 | 0.0415 (14) | 0.075 (2) | 0.0430 (14) | −0.0014 (15) | −0.0017 (12) | 0.0047 (14) |
C12 | 0.0673 (19) | 0.116 (3) | 0.0429 (15) | −0.014 (2) | 0.0021 (14) | −0.0133 (16) |
C13 | 0.0421 (15) | 0.0462 (15) | 0.0563 (15) | −0.0026 (13) | 0.0099 (12) | −0.0074 (12) |
C14 | 0.063 (2) | 0.071 (2) | 0.107 (3) | −0.0025 (17) | 0.027 (2) | 0.0204 (19) |
C15 | 0.0601 (16) | 0.0452 (15) | 0.0438 (14) | −0.0175 (13) | 0.0091 (12) | −0.0046 (12) |
S1—C15 | 1.679 (3) | C2—C3 | 1.521 (3) |
O1—C1 | 1.426 (3) | C2—H2B | 0.9800 |
O1—C5 | 1.427 (3) | C3—C4 | 1.510 (3) |
O2—C7 | 1.316 (4) | C3—H3C | 0.9800 |
O2—C6 | 1.429 (3) | C4—C5 | 1.524 (3) |
O3—C7 | 1.208 (4) | C4—H4A | 0.9800 |
O4—C9 | 1.340 (3) | C5—C6 | 1.504 (4) |
O4—C4 | 1.438 (3) | C5—H5A | 0.9800 |
O5A—C9 | 1.240 (14) | C6—H6A | 0.9700 |
O5B—C9 | 1.205 (8) | C6—H6B | 0.9700 |
O6—C11 | 1.345 (3) | C7—C8 | 1.492 (5) |
O6—C3 | 1.437 (3) | C8—H8A | 0.9600 |
O7—C11 | 1.181 (4) | C8—H8B | 0.9600 |
O8—C13 | 1.368 (3) | C8—H8C | 0.9600 |
O8—C2 | 1.441 (3) | C9—C10 | 1.486 (5) |
O9—C13 | 1.189 (3) | C10—H10A | 0.9600 |
N1—C15 | 1.350 (3) | C10—H10B | 0.9600 |
N1—C1 | 1.414 (3) | C10—H10C | 0.9600 |
N1—H1A | 0.8600 | C11—C12 | 1.488 (4) |
N2—C15 | 1.332 (4) | C12—H12A | 0.9600 |
N2—N3 | 1.395 (4) | C12—H12B | 0.9600 |
N2—H2A | 0.8600 | C12—H12C | 0.9600 |
N3—H3A | 0.8600 | C13—C14 | 1.486 (4) |
N3—H3B | 0.8600 | C14—H14A | 0.9600 |
C1—C2 | 1.536 (3) | C14—H14B | 0.9600 |
C1—H1B | 0.9800 | C14—H14C | 0.9600 |
C1—O1—C5 | 111.33 (18) | C5—C6—H6A | 110.2 |
C7—O2—C6 | 116.4 (3) | O2—C6—H6B | 110.2 |
C9—O4—C4 | 117.8 (2) | C5—C6—H6B | 110.2 |
C11—O6—C3 | 117.9 (2) | H6A—C6—H6B | 108.5 |
C13—O8—C2 | 117.7 (2) | O3—C7—O2 | 122.4 (3) |
C15—N1—C1 | 122.9 (2) | O3—C7—C8 | 125.5 (4) |
C15—N1—H1A | 118.6 | O2—C7—C8 | 111.9 (4) |
C1—N1—H1A | 118.6 | C7—C8—H8A | 109.5 |
C15—N2—N3 | 121.4 (2) | C7—C8—H8B | 109.5 |
C15—N2—H2A | 119.3 | H8A—C8—H8B | 109.5 |
N3—N2—H2A | 119.3 | C7—C8—H8C | 109.5 |
N2—N3—H3A | 120.0 | H8A—C8—H8C | 109.5 |
N2—N3—H3B | 120.0 | H8B—C8—H8C | 109.5 |
H3A—N3—H3B | 120.0 | O5B—C9—O5A | 38.8 (8) |
N1—C1—O1 | 109.0 (2) | O5B—C9—O4 | 123.8 (5) |
N1—C1—C2 | 112.9 (2) | O5A—C9—O4 | 116.8 (14) |
O1—C1—C2 | 107.74 (19) | O5B—C9—C10 | 123.1 (5) |
N1—C1—H1B | 109.1 | O5A—C9—C10 | 123.9 (8) |
O1—C1—H1B | 109.1 | O4—C9—C10 | 111.3 (3) |
C2—C1—H1B | 109.1 | C9—C10—H10A | 109.5 |
O8—C2—C3 | 106.67 (18) | C9—C10—H10B | 109.5 |
O8—C2—C1 | 110.41 (19) | H10A—C10—H10B | 109.5 |
C3—C2—C1 | 107.45 (18) | C9—C10—H10C | 109.5 |
O8—C2—H2B | 110.7 | H10A—C10—H10C | 109.5 |
C3—C2—H2B | 110.7 | H10B—C10—H10C | 109.5 |
C1—C2—H2B | 110.7 | O7—C11—O6 | 122.9 (3) |
O6—C3—C4 | 108.95 (19) | O7—C11—C12 | 125.7 (3) |
O6—C3—C2 | 108.92 (19) | O6—C11—C12 | 111.3 (3) |
C4—C3—C2 | 111.70 (19) | C11—C12—H12A | 109.5 |
O6—C3—H3C | 109.1 | C11—C12—H12B | 109.5 |
C4—C3—H3C | 109.1 | H12A—C12—H12B | 109.5 |
C2—C3—H3C | 109.1 | C11—C12—H12C | 109.5 |
O4—C4—C3 | 108.75 (19) | H12A—C12—H12C | 109.5 |
O4—C4—C5 | 109.03 (19) | H12B—C12—H12C | 109.5 |
C3—C4—C5 | 109.89 (19) | O9—C13—O8 | 122.9 (2) |
O4—C4—H4A | 109.7 | O9—C13—C14 | 126.5 (3) |
C3—C4—H4A | 109.7 | O8—C13—C14 | 110.6 (3) |
C5—C4—H4A | 109.7 | C13—C14—H14A | 109.5 |
O1—C5—C6 | 104.7 (2) | C13—C14—H14B | 109.5 |
O1—C5—C4 | 110.48 (19) | H14A—C14—H14B | 109.5 |
C6—C5—C4 | 113.3 (2) | C13—C14—H14C | 109.5 |
O1—C5—H5A | 109.4 | H14A—C14—H14C | 109.5 |
C6—C5—H5A | 109.4 | H14B—C14—H14C | 109.5 |
C4—C5—H5A | 109.4 | N2—C15—N1 | 114.7 (3) |
O2—C6—C5 | 107.6 (2) | N2—C15—S1 | 121.7 (2) |
O2—C6—H6A | 110.2 | N1—C15—S1 | 123.5 (2) |
C15—N1—C1—O1 | −86.2 (3) | C1—O1—C5—C6 | −174.4 (2) |
C15—N1—C1—C2 | 154.2 (2) | C1—O1—C5—C4 | 63.3 (3) |
C5—O1—C1—N1 | 169.66 (19) | O4—C4—C5—O1 | 65.6 (3) |
C5—O1—C1—C2 | −67.5 (2) | C3—C4—C5—O1 | −53.5 (3) |
C13—O8—C2—C3 | −146.7 (2) | O4—C4—C5—C6 | −51.5 (3) |
C13—O8—C2—C1 | 96.9 (2) | C3—C4—C5—C6 | −170.6 (2) |
N1—C1—C2—O8 | −61.7 (3) | C7—O2—C6—C5 | 152.8 (3) |
O1—C1—C2—O8 | 177.87 (18) | O1—C5—C6—O2 | −178.2 (2) |
N1—C1—C2—C3 | −177.7 (2) | C4—C5—C6—O2 | −57.7 (3) |
O1—C1—C2—C3 | 61.9 (2) | C6—O2—C7—O3 | 2.0 (6) |
C11—O6—C3—C4 | 102.1 (2) | C6—O2—C7—C8 | 178.0 (3) |
C11—O6—C3—C2 | −135.9 (2) | C4—O4—C9—O5B | 14 (2) |
O8—C2—C3—O6 | 65.6 (2) | C4—O4—C9—O5A | −31 (3) |
C1—C2—C3—O6 | −175.96 (18) | C4—O4—C9—C10 | 178.8 (3) |
O8—C2—C3—C4 | −173.97 (17) | C3—O6—C11—O7 | 11.2 (4) |
C1—C2—C3—C4 | −55.6 (3) | C3—O6—C11—C12 | −166.9 (2) |
C9—O4—C4—C3 | −109.6 (3) | C2—O8—C13—O9 | −4.3 (4) |
C9—O4—C4—C5 | 130.6 (3) | C2—O8—C13—C14 | 175.8 (2) |
O6—C3—C4—O4 | 52.6 (2) | N3—N2—C15—N1 | 5.7 (4) |
C2—C3—C4—O4 | −67.8 (2) | N3—N2—C15—S1 | −172.9 (2) |
O6—C3—C4—C5 | 171.87 (19) | C1—N1—C15—N2 | 175.9 (2) |
C2—C3—C4—C5 | 51.5 (3) | C1—N1—C15—S1 | −5.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 2.58 | 3.427 (3) | 168 |
C12—H12C···O5Bii | 0.96 | 2.31 | 3.12 (2) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z. |
Experimental details
Crystal data | |
Chemical formula | C15H23N3O9S |
Mr | 421.42 |
Crystal system, space group | Orthorhombic, P212121 |
Temperature (K) | 293 |
a, b, c (Å) | 7.5445 (11), 8.6792 (13), 31.229 (5) |
V (Å3) | 2044.9 (5) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.21 |
Crystal size (mm) | 0.30 × 0.14 × 0.11 |
Data collection | |
Diffractometer | Simens SMART CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Sheldrick, 1996) |
Tmin, Tmax | 0.940, 0.977 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 11659, 4041, 3407 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.047, 0.127, 1.02 |
No. of reflections | 4041 |
No. of parameters | 263 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.22, −0.25 |
Absolute structure | Flack (1983), 1690 Friedel pairs |
Absolute structure parameter | 0.03 (12) |
Computer programs: SMART (Siemens, 1996), SAINT (Siemens, 1996), SAINT, SHELXTL (Sheldrick, 1997), SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003).
S1—C15 | 1.679 (3) | N1—C1 | 1.414 (3) |
O1—C1 | 1.426 (3) | N2—C15 | 1.332 (4) |
O1—C5 | 1.427 (3) | N2—N3 | 1.395 (4) |
N1—C15 | 1.350 (3) | ||
N3—N2—C15—N1 | 5.7 (4) | C1—N1—C15—N2 | 175.9 (2) |
N3—N2—C15—S1 | −172.9 (2) | C1—N1—C15—S1 | −5.5 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2A···O1i | 0.86 | 2.58 | 3.427 (3) | 168 |
C12—H12C···O5Bii | 0.96 | 2.31 | 3.12 (2) | 141 |
Symmetry codes: (i) −x+1, y+1/2, −z+1/2; (ii) x+1/2, −y+1/2, −z. |
Substituted thioureas and thiosemicarbazides have attracted much attention in recent years because of their anti-HIV potential (Venkatachalam et al., 2001) and their importance in the preparation of corresponding semicarbazides (Li et al., 2001) and heterocyclic compounds (Wang et al., 2001). We have reported the synthesis and structure of N-amino-N-(2,3,4,6-tetra-O-acetyl-β-D– xylopyranosyl)thiocarbamide (II) (Yang et al., 2004) and this work has been extended to the synthesis of the title compound (I) whose structure is reported here (Fig. 1, Table 1). All bond lengths and angles in (I) are within normal ranges (Allen et al., 1987), and compare well with those values in compound (II). The acetyl group at C4 occupies an axial position, while all other substituents are equatorial. The pyranosyl ring adopts a chair conformation with the S1 atom in a synperiplanar position with respect to C1. The C1—N1—C15—S1 torsion angle is −5.5 (4)°. Atom O5 is disordered over two positions, with refined site occupancies of 0.32 (6) for O5A and 0.68 (6) for O5B.
In the crystal of (I), molecules are linked into ribbons along the a axis by C12—H12C···O5B hydrogen bonds (Fig. 2). The packing is further stabilized by N2—H2A···O1 interactions (Table 2), forming a three-dimensional framework.