Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536805021021/cv6532sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536805021021/cv6532Isup2.hkl |
CCDC reference: 282299
Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL/PC (Bruker, 2000) and PLATON (Spek, 2003); software used to prepare material for publication: SHELXL97.
C6H11N3O22+·SO42− | F(000) = 528 |
Mr = 253.25 | Dx = 1.643 Mg m−3 Dm = 1.632 Mg m−3 Dm measured by flotation in a liquid mixture of CCl4 and bromoform |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
a = 6.8616 (6) Å | Cell parameters from 25 reflections |
b = 5.8084 (6) Å | θ = 9.6–11.8° |
c = 25.6901 (18) Å | µ = 0.34 mm−1 |
β = 90.733 (8)° | T = 293 K |
V = 1023.79 (16) Å3 | Block, colourless |
Z = 4 | 0.22 × 0.16 × 0.12 mm |
Nonius MACH-3 sealed-tube diffractometer | 2161 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.094 |
Graphite monochromator | θmax = 25.0°, θmin = 2.4° |
ω–2θ scans | h = 0→8 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→6 |
Tmin = 0.774, Tmax = 0.999 | l = −30→30 |
2571 measured reflections | 3 standard reflections every 60 min |
2368 independent reflections | intensity decay: none |
Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
Least-squares matrix: full | H-atom parameters constrained |
R[F2 > 2σ(F2)] = 0.047 | w = 1/[σ2(Fo2) + (0.1269P)2 + 1.9828P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.189 | (Δ/σ)max < 0.001 |
S = 1.15 | Δρmax = 0.44 e Å−3 |
2368 reflections | Δρmin = −0.51 e Å−3 |
294 parameters | Extinction correction: SHELXL97, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
1 restraint | Extinction coefficient: 0.131 (13) |
Primary atom site location: structure-invariant direct methods | Absolute structure: Flack (1983) |
Secondary atom site location: difference Fourier map | Absolute structure parameter: −0.09 (18) |
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 | ||
O1A | 0.8595 (8) | 0.7098 (12) | 0.4952 (2) | 0.0399 (15) | |
O1B | 0.6669 (8) | 0.4012 (12) | 0.4855 (2) | 0.0405 (16) | |
H1B | 0.6364 | 0.4637 | 0.4580 | 0.061* | |
C11 | 0.7867 (9) | 0.5338 (16) | 0.5116 (2) | 0.0254 (16) | |
C12 | 0.8271 (8) | 0.4508 (14) | 0.5668 (2) | 0.0200 (13) | |
H12 | 0.8211 | 0.2823 | 0.5678 | 0.024* | |
N11 | 1.0260 (7) | 0.5288 (12) | 0.5821 (2) | 0.0227 (12) | |
H11A | 1.1083 | 0.4992 | 0.5565 | 0.034* | |
H11B | 1.0646 | 0.4545 | 0.6107 | 0.034* | |
H11C | 1.0243 | 0.6796 | 0.5883 | 0.034* | |
C13 | 0.6709 (9) | 0.5518 (16) | 0.6022 (3) | 0.0286 (16) | |
H13A | 0.6787 | 0.7184 | 0.6007 | 0.034* | |
H13B | 0.5436 | 0.5073 | 0.5888 | 0.034* | |
C14 | 0.6867 (8) | 0.4786 (15) | 0.6575 (2) | 0.0223 (15) | |
C15 | 0.7591 (9) | 0.2871 (15) | 0.6802 (3) | 0.0243 (15) | |
H15 | 0.8212 | 0.1660 | 0.6635 | 0.029* | |
N12 | 0.7242 (7) | 0.3041 (12) | 0.7320 (2) | 0.0224 (13) | |
H12A | 0.7568 | 0.2032 | 0.7550 | 0.027* | |
C16 | 0.6329 (9) | 0.4985 (14) | 0.7415 (3) | 0.0252 (16) | |
H16 | 0.5920 | 0.5491 | 0.7740 | 0.030* | |
N13 | 0.6094 (7) | 0.6089 (11) | 0.6970 (2) | 0.0231 (13) | |
H13 | 0.5546 | 0.7412 | 0.6933 | 0.028* | |
O2A | 0.3835 (9) | 0.2315 (14) | 0.9980 (2) | 0.0498 (19) | |
O2B | 0.1415 (7) | 0.4673 (13) | 1.01944 (19) | 0.0371 (14) | |
H2B | 0.1580 | 0.4115 | 1.0485 | 0.056* | |
C21 | 0.2661 (9) | 0.3805 (15) | 0.9878 (3) | 0.0248 (16) | |
C22 | 0.2551 (8) | 0.4796 (15) | 0.9332 (2) | 0.0216 (14) | |
H22 | 0.1882 | 0.6287 | 0.9338 | 0.026* | |
N21 | 0.4578 (7) | 0.5110 (10) | 0.9148 (2) | 0.0205 (12) | |
H21A | 0.5324 | 0.5621 | 0.9410 | 0.031* | |
H21B | 0.4585 | 0.6128 | 0.8890 | 0.031* | |
H21C | 0.5038 | 0.3769 | 0.9036 | 0.031* | |
C23 | 0.1437 (10) | 0.3128 (16) | 0.8970 (3) | 0.0299 (17) | |
H23A | 0.1985 | 0.1598 | 0.9010 | 0.036* | |
H23B | 0.0087 | 0.3063 | 0.9076 | 0.036* | |
C24 | 0.1503 (8) | 0.3791 (14) | 0.8404 (3) | 0.0234 (15) | |
C25 | 0.2247 (9) | 0.2690 (14) | 0.8000 (3) | 0.0262 (16) | |
H25 | 0.2878 | 0.1273 | 0.8006 | 0.031* | |
N22 | 0.1904 (7) | 0.4052 (12) | 0.7568 (2) | 0.0244 (14) | |
H22A | 0.2234 | 0.3730 | 0.7255 | 0.029* | |
C26 | 0.0985 (9) | 0.5934 (14) | 0.7717 (3) | 0.0257 (16) | |
H26 | 0.0595 | 0.7139 | 0.7501 | 0.031* | |
N23 | 0.0716 (7) | 0.5810 (12) | 0.8224 (2) | 0.0226 (13) | |
H23 | 0.0141 | 0.6829 | 0.8410 | 0.027* | |
S1 | 0.2631 (2) | 0.0470 (3) | 0.64646 (6) | 0.0232 (5) | |
O11 | 0.4123 (7) | 0.0128 (12) | 0.60718 (19) | 0.0371 (15) | |
O12 | 0.0779 (8) | −0.0443 (14) | 0.6272 (3) | 0.0529 (18) | |
O13 | 0.2379 (7) | 0.2988 (10) | 0.65572 (19) | 0.0259 (11) | |
O14 | 0.3275 (9) | −0.0596 (13) | 0.6952 (2) | 0.0463 (16) | |
S2 | 0.6944 (2) | 0.9604 (3) | 0.84857 (6) | 0.0198 (5) | |
O21 | 0.7928 (8) | 0.9489 (12) | 0.7987 (2) | 0.0348 (13) | |
O22 | 0.5024 (7) | 0.8511 (12) | 0.8439 (2) | 0.0420 (16) | |
O23 | 0.6758 (8) | 1.2003 (11) | 0.8651 (3) | 0.0443 (16) | |
O24 | 0.8172 (6) | 0.8270 (11) | 0.88683 (18) | 0.0272 (12) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.047 (3) | 0.039 (4) | 0.034 (3) | −0.018 (3) | −0.007 (2) | 0.019 (3) |
O1B | 0.048 (3) | 0.045 (4) | 0.028 (3) | −0.023 (3) | −0.017 (2) | 0.010 (3) |
C11 | 0.023 (3) | 0.030 (4) | 0.023 (3) | −0.001 (3) | −0.001 (2) | 0.005 (3) |
C12 | 0.023 (3) | 0.018 (3) | 0.020 (3) | −0.002 (3) | −0.004 (2) | 0.002 (3) |
N11 | 0.021 (2) | 0.022 (3) | 0.025 (3) | 0.005 (3) | −0.0024 (19) | −0.001 (3) |
C13 | 0.024 (3) | 0.031 (4) | 0.030 (3) | 0.009 (4) | 0.003 (2) | 0.007 (4) |
C14 | 0.016 (3) | 0.029 (4) | 0.023 (3) | 0.005 (3) | 0.005 (2) | 0.007 (3) |
C15 | 0.022 (3) | 0.020 (4) | 0.031 (4) | 0.002 (3) | 0.002 (3) | 0.004 (3) |
N12 | 0.021 (2) | 0.025 (3) | 0.021 (3) | 0.001 (3) | 0.001 (2) | 0.007 (3) |
C16 | 0.019 (3) | 0.028 (5) | 0.029 (3) | −0.002 (3) | 0.004 (2) | 0.000 (3) |
N13 | 0.020 (2) | 0.020 (3) | 0.030 (3) | 0.005 (2) | 0.004 (2) | −0.002 (3) |
O2A | 0.058 (3) | 0.059 (5) | 0.033 (3) | 0.035 (4) | 0.008 (3) | 0.020 (3) |
O2B | 0.036 (2) | 0.050 (4) | 0.026 (2) | 0.013 (3) | 0.0069 (19) | 0.005 (3) |
C21 | 0.023 (3) | 0.030 (4) | 0.022 (3) | −0.001 (3) | −0.004 (2) | 0.003 (3) |
C22 | 0.019 (3) | 0.024 (4) | 0.022 (3) | 0.007 (3) | 0.004 (2) | 0.003 (3) |
N21 | 0.018 (2) | 0.018 (3) | 0.026 (2) | −0.001 (2) | −0.0013 (18) | 0.002 (2) |
C23 | 0.024 (3) | 0.033 (5) | 0.032 (4) | −0.009 (3) | −0.004 (3) | 0.007 (4) |
C24 | 0.011 (2) | 0.024 (4) | 0.035 (4) | −0.002 (3) | −0.005 (2) | 0.001 (3) |
C25 | 0.017 (3) | 0.021 (4) | 0.040 (4) | 0.002 (3) | −0.005 (3) | −0.003 (3) |
N22 | 0.017 (2) | 0.032 (4) | 0.024 (3) | 0.003 (3) | −0.001 (2) | −0.006 (3) |
C26 | 0.021 (3) | 0.029 (4) | 0.028 (3) | 0.001 (3) | −0.006 (2) | 0.001 (3) |
N23 | 0.018 (2) | 0.027 (4) | 0.023 (3) | 0.007 (3) | −0.0005 (19) | −0.003 (3) |
S1 | 0.0213 (8) | 0.0182 (9) | 0.0301 (9) | 0.0085 (7) | −0.0044 (6) | −0.0069 (7) |
O11 | 0.030 (2) | 0.048 (4) | 0.033 (2) | 0.017 (3) | −0.0081 (19) | −0.017 (3) |
O12 | 0.030 (3) | 0.045 (4) | 0.084 (5) | 0.001 (3) | −0.007 (3) | −0.031 (4) |
O13 | 0.030 (2) | 0.013 (3) | 0.035 (3) | 0.009 (2) | −0.0037 (19) | −0.006 (2) |
O14 | 0.065 (4) | 0.039 (4) | 0.035 (3) | 0.030 (4) | 0.006 (3) | 0.007 (3) |
S2 | 0.0183 (7) | 0.0152 (9) | 0.0260 (8) | 0.0034 (7) | 0.0023 (5) | 0.0013 (7) |
O21 | 0.042 (3) | 0.027 (3) | 0.036 (3) | 0.014 (3) | 0.006 (2) | 0.007 (3) |
O22 | 0.022 (2) | 0.038 (4) | 0.066 (4) | −0.009 (3) | −0.010 (2) | 0.023 (3) |
O23 | 0.038 (3) | 0.020 (3) | 0.076 (4) | 0.011 (3) | 0.009 (3) | −0.017 (3) |
O24 | 0.028 (2) | 0.032 (3) | 0.021 (2) | 0.012 (2) | 0.0005 (18) | −0.003 (2) |
O1A—C11 | 1.216 (10) | C22—N21 | 1.486 (7) |
O1B—C11 | 1.305 (9) | C22—C23 | 1.540 (10) |
O1B—H1B | 0.8200 | C22—H22 | 0.9800 |
C11—C12 | 1.519 (9) | N21—H21A | 0.8900 |
C12—N11 | 1.487 (8) | N21—H21B | 0.8900 |
C12—C13 | 1.532 (9) | N21—H21C | 0.8900 |
C12—H12 | 0.9800 | C23—C24 | 1.504 (10) |
N11—H11A | 0.8900 | C23—H23A | 0.9700 |
N11—H11B | 0.8900 | C23—H23B | 0.9700 |
N11—H11C | 0.8900 | C24—C25 | 1.328 (11) |
C13—C14 | 1.486 (9) | C24—N23 | 1.370 (10) |
C13—H13A | 0.9700 | C25—N22 | 1.379 (10) |
C13—H13B | 0.9700 | C25—H25 | 0.9300 |
C14—C15 | 1.348 (11) | N22—C26 | 1.321 (10) |
C14—N13 | 1.377 (9) | N22—H22A | 0.8600 |
C15—N12 | 1.358 (9) | C26—N23 | 1.320 (9) |
C15—H15 | 0.9300 | C26—H26 | 0.9300 |
N12—C16 | 1.316 (10) | N23—H23 | 0.8600 |
N12—H12A | 0.8600 | S1—O12 | 1.458 (6) |
C16—N13 | 1.319 (9) | S1—O11 | 1.460 (5) |
C16—H16 | 0.9300 | S1—O14 | 1.460 (6) |
N13—H13 | 0.8600 | S1—O13 | 1.492 (6) |
O2A—C21 | 1.208 (10) | S2—O21 | 1.458 (5) |
O2B—C21 | 1.289 (9) | S2—O23 | 1.462 (7) |
O2B—H2B | 0.8200 | S2—O22 | 1.466 (5) |
C21—C22 | 1.518 (9) | S2—O24 | 1.502 (5) |
C11—O1B—H1B | 109.5 | C21—C22—C23 | 109.8 (6) |
O1A—C11—O1B | 125.3 (6) | N21—C22—H22 | 109.7 |
O1A—C11—C12 | 121.3 (6) | C21—C22—H22 | 109.7 |
O1B—C11—C12 | 113.4 (7) | C23—C22—H22 | 109.7 |
N11—C12—C11 | 107.9 (5) | C22—N21—H21A | 109.5 |
N11—C12—C13 | 111.9 (6) | C22—N21—H21B | 109.5 |
C11—C12—C13 | 108.2 (5) | H21A—N21—H21B | 109.5 |
N11—C12—H12 | 109.6 | C22—N21—H21C | 109.5 |
C11—C12—H12 | 109.6 | H21A—N21—H21C | 109.5 |
C13—C12—H12 | 109.6 | H21B—N21—H21C | 109.5 |
C12—N11—H11A | 109.5 | C24—C23—C22 | 113.7 (6) |
C12—N11—H11B | 109.5 | C24—C23—H23A | 108.8 |
H11A—N11—H11B | 109.5 | C22—C23—H23A | 108.8 |
C12—N11—H11C | 109.5 | C24—C23—H23B | 108.8 |
H11A—N11—H11C | 109.5 | C22—C23—H23B | 108.8 |
H11B—N11—H11C | 109.5 | H23A—C23—H23B | 107.7 |
C14—C13—C12 | 114.6 (6) | C25—C24—N23 | 107.6 (6) |
C14—C13—H13A | 108.6 | C25—C24—C23 | 130.5 (8) |
C12—C13—H13A | 108.6 | N23—C24—C23 | 122.0 (7) |
C14—C13—H13B | 108.6 | C24—C25—N22 | 106.8 (7) |
C12—C13—H13B | 108.6 | C24—C25—H25 | 126.6 |
H13A—C13—H13B | 107.6 | N22—C25—H25 | 126.6 |
C15—C14—N13 | 106.2 (6) | C26—N22—C25 | 108.7 (6) |
C15—C14—C13 | 132.2 (7) | C26—N22—H22A | 125.7 |
N13—C14—C13 | 121.5 (7) | C25—N22—H22A | 125.7 |
C14—C15—N12 | 107.1 (7) | N23—C26—N22 | 108.3 (7) |
C14—C15—H15 | 126.4 | N23—C26—H26 | 125.9 |
N12—C15—H15 | 126.4 | N22—C26—H26 | 125.9 |
C16—N12—C15 | 109.6 (6) | C26—N23—C24 | 108.7 (6) |
C16—N12—H12A | 125.2 | C26—N23—H23 | 125.6 |
C15—N12—H12A | 125.2 | C24—N23—H23 | 125.6 |
N12—C16—N13 | 108.0 (6) | O12—S1—O11 | 109.3 (3) |
N12—C16—H16 | 126.0 | O12—S1—O14 | 113.0 (5) |
N13—C16—H16 | 126.0 | O11—S1—O14 | 109.1 (3) |
C16—N13—C14 | 109.1 (6) | O12—S1—O13 | 108.0 (4) |
C16—N13—H13 | 125.5 | O11—S1—O13 | 109.1 (4) |
C14—N13—H13 | 125.5 | O14—S1—O13 | 108.3 (4) |
C21—O2B—H2B | 109.5 | O21—S2—O23 | 110.0 (4) |
O2A—C21—O2B | 126.2 (7) | O21—S2—O22 | 109.5 (4) |
O2A—C21—C22 | 119.7 (6) | O23—S2—O22 | 110.8 (4) |
O2B—C21—C22 | 114.1 (6) | O21—S2—O24 | 106.8 (3) |
N21—C22—C21 | 107.7 (5) | O23—S2—O24 | 110.6 (4) |
N21—C22—C23 | 110.1 (5) | O22—S2—O24 | 109.0 (3) |
O1A—C11—C12—N11 | −30.1 (9) | O2A—C21—C22—N21 | −41.6 (10) |
O1B—C11—C12—N11 | 151.1 (7) | O2B—C21—C22—N21 | 139.3 (7) |
O1A—C11—C12—C13 | 91.1 (8) | O2A—C21—C22—C23 | 78.4 (8) |
O1B—C11—C12—C13 | −87.7 (8) | O2B—C21—C22—C23 | −100.8 (8) |
N11—C12—C13—C14 | −63.5 (9) | N21—C22—C23—C24 | −53.1 (8) |
C11—C12—C13—C14 | 177.9 (7) | C21—C22—C23—C24 | −171.5 (6) |
C12—C13—C14—C15 | −28.0 (12) | C22—C23—C24—C25 | 117.6 (9) |
C12—C13—C14—N13 | 156.3 (6) | C22—C23—C24—N23 | −62.7 (8) |
N13—C14—C15—N12 | 0.3 (7) | N23—C24—C25—N22 | −0.1 (7) |
C13—C14—C15—N12 | −176.0 (7) | C23—C24—C25—N22 | 179.6 (6) |
C14—C15—N12—C16 | 0.2 (8) | C24—C25—N22—C26 | 0.4 (8) |
C15—N12—C16—N13 | −0.6 (8) | C25—N22—C26—N23 | −0.6 (7) |
N12—C16—N13—C14 | 0.7 (7) | N22—C26—N23—C24 | 0.5 (7) |
C15—C14—N13—C16 | −0.6 (7) | C25—C24—N23—C26 | −0.2 (7) |
C13—C14—N13—C16 | 176.1 (6) | C23—C24—N23—C26 | −180.0 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1B···O11i | 0.82 | 1.73 | 2.521 (7) | 163 |
N11—H11A···O1Aii | 0.89 | 2.15 | 2.834 (8) | 133 |
N11—H11B···O13iii | 0.89 | 1.88 | 2.721 (8) | 157 |
N11—H11C···O12iv | 0.89 | 1.92 | 2.757 (10) | 156 |
N12—H12A···O21v | 0.86 | 1.87 | 2.719 (8) | 169 |
N13—H13···O14vi | 0.86 | 1.94 | 2.729 (8) | 152 |
O2B—H2B···O24vii | 0.82 | 1.74 | 2.554 (7) | 173 |
N21—H21A···O2Aviii | 0.89 | 1.93 | 2.790 (8) | 161 |
N21—H21B···O22 | 0.89 | 1.83 | 2.708 (8) | 168 |
N21—H21C···O23v | 0.89 | 1.86 | 2.679 (8) | 152 |
N22—H22A···O13 | 0.86 | 1.85 | 2.694 (8) | 168 |
N23—H23···O24ix | 0.86 | 1.99 | 2.811 (7) | 160 |
Symmetry codes: (i) −x+1, y+1/2, −z+1; (ii) −x+2, y−1/2, −z+1; (iii) x+1, y, z; (iv) x+1, y+1, z; (v) x, y−1, z; (vi) x, y+1, z; (vii) −x+1, y−1/2, −z+2; (viii) −x+1, y+1/2, −z+2; (ix) x−1, y, z. |