Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270100011100/qa0372sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S0108270100011100/qa0372Isup2.hkl |
CCDC reference: 150750
Data collection: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); cell refinement: MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1999a); data reduction: TEXSAN PROCESS (Molecular Structure Corporation, 1999b); program(s) used to solve structure: SIR88 (Burla et al., 1989) and DIRDIF (Beurskens et al., 1994); program(s) used to refine structure: TEXSAN LS; software used to prepare material for publication: TEXSAN.
C10H14N2O32+·SO42−·2H2O | Dx = 1.534 Mg m−3 |
Mr = 342.32 | Mo Kα radiation, λ = 0.71069 Å |
Orthorhombic, P212121 | Cell parameters from 25 reflections |
a = 11.353 (5) Å | θ = 10.3–14.5° |
b = 22.134 (5) Å | µ = 0.27 mm−1 |
c = 5.897 (7) Å | T = 296 K |
V = 1481 (1) Å3 | Needle, light yellow |
Z = 4 | 0.50 × 0.10 × 0.05 mm |
Rigaku AFC-5R diffractometer | Rint = 0.058 |
ω–2θ scans | θmax = 27.5° |
Absorption correction: ψ scan (North et al., 1968) | h = −14→14 |
Tmin = 0.972, Tmax = 0.998 | k = −28→28 |
4128 measured reflections | l = −7→7 |
2072 independent reflections | 3 standard reflections every 150 reflections |
1088 reflections with F2 > 2σ(F2) | intensity decay: 0.1% |
Refinement on F2 | H-atom parameters not refined |
R[F2 > 2σ(F2)] = 0.057 | w = 1/[σ2(Fo2) + (0.06100(Max(Fo2,0) + 2Fc2)/3)2] |
wR(F2) = 0.163 | (Δ/σ)max = 0.004 |
S = 1.15 | Δρmax = 0.81 e Å−3 |
2071 reflections | Δρmin = −0.90 e Å−3 |
200 parameters |
Refinement. Refinement using reflections with F2 > -10.0 σ(F2). The weighted R-factor (wR) and goodness of fit (S) are based on F2. R-factor (gt) are based on F. The threshold expression of F2 > 2.0 σ(F2) is used only for calculating R-factor (gt). |
x | y | z | Uiso*/Ueq | ||
S | 0.1157 (1) | 0.10868 (7) | 0.0645 (3) | 0.0328 (4) | |
O1 | 0.3674 (4) | 0.0657 (2) | 0.4722 (7) | 0.044 (1) | |
O2 | 0.5063 (4) | 0.2318 (2) | 0.9046 (9) | 0.053 (1) | |
O3 | 0.3324 (4) | 0.2748 (2) | 0.8345 (9) | 0.053 (1) | |
O4 | 0.1080 (4) | 0.1037 (2) | 0.3108 (7) | 0.042 (1) | |
O5 | 0.1170 (5) | 0.1721 (2) | −0.0005 (8) | 0.057 (1) | |
O6 | 0.0108 (4) | 0.0798 (2) | −0.0396 (9) | 0.059 (2) | |
O7 | 0.2182 (4) | 0.0787 (2) | −0.0293 (9) | 0.053 (2) | |
O8 | 0.7406 (5) | 0.2143 (2) | 0.6611 (9) | 0.065 (2) | |
O9 | 0.9181 (8) | 0.1402 (5) | 0.588 (1) | 0.168 (4) | |
N1 | 0.3908 (5) | −0.0003 (2) | 0.0929 (8) | 0.029 (1) | |
N2 | 0.2493 (4) | 0.1814 (2) | 0.6008 (9) | 0.030 (1) | |
C1 | 0.5284 (5) | 0.0801 (2) | 0.223 (1) | 0.029 (1) | |
C2 | 0.5027 (5) | 0.0335 (2) | 0.071 (1) | 0.028 (1) | |
C3 | 0.5777 (6) | 0.0176 (3) | −0.098 (1) | 0.039 (2) | |
C4 | 0.6861 (6) | 0.0476 (3) | −0.118 (1) | 0.046 (2) | |
C5 | 0.7152 (5) | 0.0921 (3) | 0.031 (1) | 0.045 (2) | |
C6 | 0.6368 (5) | 0.1092 (3) | 0.196 (1) | 0.037 (2) | |
C7 | 0.4444 (5) | 0.0992 (3) | 0.406 (1) | 0.031 (1) | |
C8 | 0.4585 (6) | 0.1615 (3) | 0.503 (1) | 0.036 (2) | |
C9 | 0.3688 (5) | 0.1759 (2) | 0.6883 (10) | 0.027 (1) | |
C10 | 0.4004 (6) | 0.2341 (3) | 0.8165 (10) | 0.032 (1) | |
H1 | 0.5594 | −0.0150 | −0.1918 | 0.0440* | |
H2 | 0.7419 | 0.0347 | −0.2218 | 0.0591* | |
H3 | 0.7892 | 0.1112 | 0.0127 | 0.0633* | |
H4 | 0.6569 | 0.1415 | 0.2949 | 0.0373* | |
H5 | 0.5359 | 0.1668 | 0.5558 | 0.0397* | |
H6 | 0.4464 | 0.1894 | 0.3760 | 0.0397* | |
H7 | 0.3703 | 0.1434 | 0.7935 | 0.0280* | |
H8 | 0.5064 | 0.2873 | 0.8871 | 0.0610* | |
H9 | 0.1954 | 0.1671 | 0.7149 | 0.0327* | |
H10 | 0.2327 | 0.2230 | 0.5731 | 0.0327* | |
H11 | 0.2405 | 0.1588 | 0.4685 | 0.0327* | |
H12 | 0.3892 | −0.0197 | 0.2445 | 0.0415* | |
H13 | 0.3264 | 0.0253 | 0.0833 | 0.0415* | |
H14 | 0.3874 | −0.0317 | −0.0147 | 0.0415* | |
H15 | 0.6970 | 0.2428 | 0.7383 | 0.0610* | |
H16 | 0.8016 | 0.2228 | 0.7087 | 0.0610* | |
H17 | 0.9535 | 0.1831 | 0.5596 | 0.0610* | |
H18 | 0.9376 | 0.1241 | 0.7491 | 0.0610* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0401 (9) | 0.0300 (7) | 0.0283 (7) | 0.0087 (8) | 0.0104 (8) | 0.0074 (7) |
O1 | 0.046 (3) | 0.036 (2) | 0.048 (3) | −0.013 (2) | 0.018 (3) | −0.012 (2) |
O2 | 0.049 (2) | 0.038 (2) | 0.072 (4) | 0.006 (2) | −0.016 (3) | −0.013 (3) |
O3 | 0.052 (3) | 0.040 (3) | 0.068 (3) | 0.009 (2) | −0.014 (3) | −0.023 (3) |
O4 | 0.052 (3) | 0.042 (2) | 0.031 (1) | −0.014 (3) | 0.010 (3) | 0.003 (2) |
O5 | 0.075 (3) | 0.030 (2) | 0.065 (3) | 0.017 (3) | 0.041 (3) | 0.011 (2) |
O6 | 0.056 (3) | 0.077 (4) | 0.045 (3) | −0.015 (3) | −0.011 (3) | −0.007 (3) |
O7 | 0.054 (3) | 0.044 (3) | 0.060 (4) | 0.031 (2) | 0.028 (3) | 0.015 (3) |
O8 | 0.068 (4) | 0.059 (3) | 0.069 (4) | 0.017 (3) | 0.009 (3) | 0.012 (3) |
O9 | 0.173 (9) | 0.25 (1) | 0.076 (5) | 0.159 (8) | 0.029 (6) | 0.063 (7) |
N1 | 0.033 (2) | 0.025 (2) | 0.029 (2) | −0.001 (2) | 0.001 (3) | −0.006 (2) |
N2 | 0.033 (2) | 0.023 (2) | 0.034 (3) | −0.008 (2) | 0.016 (2) | −0.007 (2) |
C1 | 0.030 (3) | 0.027 (3) | 0.031 (3) | 0.000 (2) | −0.002 (2) | −0.002 (2) |
C2 | 0.030 (3) | 0.026 (3) | 0.029 (3) | −0.001 (2) | −0.003 (3) | 0.004 (2) |
C3 | 0.041 (3) | 0.041 (4) | 0.036 (4) | −0.002 (3) | 0.006 (3) | −0.014 (3) |
C4 | 0.038 (3) | 0.053 (5) | 0.048 (5) | 0.001 (3) | 0.022 (3) | −0.008 (3) |
C5 | 0.025 (3) | 0.052 (4) | 0.057 (5) | −0.006 (3) | 0.012 (3) | −0.006 (3) |
C6 | 0.033 (3) | 0.034 (3) | 0.042 (3) | −0.006 (3) | 0.002 (3) | −0.005 (3) |
C7 | 0.033 (3) | 0.028 (3) | 0.032 (3) | 0.004 (2) | −0.001 (2) | −0.004 (2) |
C8 | 0.033 (3) | 0.032 (3) | 0.043 (4) | −0.004 (3) | 0.015 (3) | −0.016 (3) |
C9 | 0.037 (3) | 0.018 (2) | 0.027 (3) | −0.001 (3) | 0.008 (2) | 0.006 (2) |
C10 | 0.046 (3) | 0.029 (3) | 0.022 (3) | −0.009 (2) | 0.007 (3) | −0.004 (2) |
S—O4 | 1.461 (4) | C1—C6 | 1.397 (9) |
S—O5 | 1.455 (5) | C1—C7 | 1.500 (9) |
S—O6 | 1.486 (5) | C2—C3 | 1.357 (9) |
S—O7 | 1.447 (5) | C3—C4 | 1.405 (10) |
O1—C7 | 1.212 (8) | C4—C5 | 1.36 (1) |
O2—C10 | 1.309 (8) | C5—C6 | 1.374 (9) |
O3—C10 | 1.189 (8) | C7—C8 | 1.503 (9) |
N1—C2 | 1.480 (8) | C8—C9 | 1.527 (9) |
N2—C9 | 1.458 (8) | C9—C10 | 1.537 (9) |
C1—C2 | 1.398 (8) | ||
O4—S—O5 | 109.8 (3) | C3—C4—C5 | 119.9 (6) |
O4—S—O6 | 109.3 (3) | C4—C5—C6 | 120.1 (6) |
O4—S—O7 | 113.1 (3) | C1—C6—C5 | 121.7 (7) |
O5—S—O6 | 108.3 (4) | O1—C7—C1 | 121.3 (5) |
O5—S—O7 | 109.4 (3) | O1—C7—C8 | 121.1 (6) |
O6—S—O7 | 106.8 (3) | C1—C7—C8 | 117.6 (5) |
C2—C1—C6 | 116.8 (6) | C7—C8—C9 | 113.1 (5) |
C2—C1—C7 | 122.3 (6) | N2—C9—C8 | 112.6 (5) |
C6—C1—C7 | 120.9 (6) | N2—C9—C10 | 108.8 (5) |
N1—C2—C1 | 119.8 (6) | C8—C9—C10 | 111.9 (5) |
N1—C2—C3 | 118.2 (5) | O2—C10—O3 | 126.1 (6) |
C1—C2—C3 | 122.0 (6) | O2—C10—C9 | 112.2 (6) |
C2—C3—C4 | 119.5 (6) | O3—C10—C9 | 121.7 (6) |
O1—C7—C1—C2 | 21.2 (10) | C1—C6—C5—C4 | 2 (1) |
O1—C7—C1—C6 | −159.6 (7) | C1—C7—C8—C9 | −179.6 (5) |
O1—C7—C8—C9 | 0.7 (9) | C2—C1—C6—C5 | −1 (1) |
O2—C10—C9—N2 | 178.6 (5) | C2—C1—C7—C8 | −158.4 (6) |
O2—C10—C9—C8 | −56.5 (7) | C2—C3—C4—C5 | −0 (1) |
O3—C10—C9—N2 | 0.4 (8) | C3—C2—C1—C6 | −1.1 (9) |
O3—C10—C9—C8 | 125.3 (7) | C3—C2—C1—C7 | 178.1 (6) |
N1—C2—C1—C6 | 178.6 (5) | C3—C4—C5—C6 | −1 (1) |
N1—C2—C1—C7 | −2.2 (9) | C5—C6—C1—C7 | 179.7 (6) |
N1—C2—C3—C4 | −177.9 (6) | C6—C1—C7—C8 | 20.8 (9) |
N2—C9—C8—C7 | −68.7 (7) | C7—C8—C9—C10 | 168.4 (5) |
C1—C2—C3—C4 | 1 (1) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H12···O1 | 0.991 | 2.334 | 2.688 (7) | 99.928 |
N2—H11···O1 | 0.929 | 2.514 | 2.992 (7) | 112.188 |
N2—H10···O3 | 0.949 | 2.225 | 2.655 (7) | 106.467 |
N1—H13···O7 | 0.929 | 1.826 | 2.723 (7) | 161.424 |
N1—H12···O6i | 0.991 | 2.162 | 3.004 (8) | 141.845 |
N1—H12···O7i | 0.991 | 2.234 | 3.086 (7) | 143.381 |
N1—H14···O4ii | 0.939 | 1.893 | 2.822 (6) | 169.482 |
N2—H11···O4 | 0.929 | 2.150 | 2.906 (7) | 137.703 |
N2—H9···O5iii | 0.964 | 1.903 | 2.799 (8) | 153.490 |
N2—H9···O7iii | 0.964 | 2.488 | 3.178 (8) | 128.416 |
N1—H13···O1ii | 0.929 | 3.055 | 3.345 (7) | 100.033 |
Symmetry codes: (i) −x+1/2, −y, z+1/2; (ii) −x+1/2, −y, z−1/2; (iii) x, y, z+1. |