Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804026108/hg6090sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804026108/hg6090Isup2.hkl |
CCDC reference: 255926
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.008 Å
- R factor = 0.059
- wR factor = 0.171
- Data-to-parameter ratio = 8.6
checkCIF/PLATON results
No syntax errors found
Alert level A PLAT052_ALERT_1_A (Proper) Absorption Correction Method Missing .. ? PLAT242_ALERT_2_A Check Low U(eq) as Compared to Neighbors for S
Alert level B PLAT417_ALERT_2_B Short Inter D-H..H-D H1B .. HW2 .. 2.03 Ang.
Alert level C PLAT034_ALERT_1_C No Flack Parameter Given. Z .GT. Si, NonCentro . ? PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical . ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 8 PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........ 3
Alert level G REFLT03_ALERT_4_G WARNING: Large fraction of Friedel related reflns may be needed to determine absolute structure From the CIF: _diffrn_reflns_theta_max 25.00 From the CIF: _reflns_number_total 1172 Count of symmetry unique reflns 1176 Completeness (_total/calc) 99.66% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 0 Fraction of Friedel pairs measured 0.000 Are heavy atom types Z>Si present yes
2 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 5 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 4 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 2 ALERT type 2 Indicator that the structure model may be wrong or deficient 1 ALERT type 3 Indicator that the structure quality may be low 2 ALERT type 4 Improvement, methodology, query or suggestion
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: ORTEP-3 (Farrugia, 1997) and PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C5H14N2O22+·SO42−·H2O | F(000) = 528 |
Mr = 248.26 | Dx = 1.478 Mg m−3 Dm = 1.475 (5) Mg m−3 Dm measured by flotation, using a mixture of CCl4 and xylene |
Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2ac 2ab | Cell parameters from 25 reflections |
a = 6.1589 (2) Å | θ = 11.3–14.2° |
b = 9.682 (6) Å | µ = 0.31 mm−1 |
c = 18.714 (6) Å | T = 293 K |
V = 1115.9 (8) Å3 | Needle, colourless |
Z = 4 | 0.3 × 0.3 × 0.2 mm |
Nonius MACH 3 diffractometer | 1043 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.029 |
Graphite monochromator | θmax = 25°, θmin = 2.2° |
ω/2θ scans | h = 0→7 |
Absorption correction: ψ scan (North et al., 1968) | k = −1→11 |
Tmin = 0.911, Tmax = 0.940 | l = −1→22 |
1399 measured reflections | 3 standard reflections every 60 min |
1172 independent reflections | intensity decay: none |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.171 | H-atom parameters constrained |
S = 1.06 | w = 1/[σ2(Fo2) + (0.112P)2 + 1.3829P] where P = (Fo2 + 2Fc2)/3 |
1172 reflections | (Δ/σ)max = 0.005 |
137 parameters | Δρmax = 0.73 e Å−3 |
0 restraints | Δρmin = −0.37 e Å−3 |
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 | ||
S | 0.8970 (2) | 1.08983 (15) | 0.38083 (7) | 0.0351 (4) | |
O1 | 0.9854 (11) | 0.9625 (6) | 0.4097 (3) | 0.0727 (17) | |
O2 | 1.0139 (15) | 1.1997 (7) | 0.4173 (4) | 0.115 (3) | |
O3 | 0.6680 (9) | 1.0937 (11) | 0.3919 (3) | 0.113 (3) | |
O4 | 0.9426 (8) | 1.0964 (5) | 0.3028 (2) | 0.0601 (13) | |
O1B | 0.2449 (8) | 0.7737 (5) | 0.3687 (2) | 0.0521 (12) | |
H1 | 0.1294 | 0.8153 | 0.3654 | 0.078* | |
O1A | 0.3372 (7) | 0.8776 (4) | 0.2665 (2) | 0.0484 (11) | |
C1 | 0.3527 (10) | 0.7842 (5) | 0.3081 (3) | 0.0348 (12) | |
C2 | 0.5051 (9) | 0.6633 (5) | 0.2972 (3) | 0.0339 (12) | |
H2 | 0.4232 | 0.5770 | 0.3018 | 0.041* | |
N1 | 0.5922 (8) | 0.6736 (5) | 0.2243 (2) | 0.0386 (11) | |
H1A | 0.6823 | 0.6034 | 0.2162 | 0.058* | |
H1B | 0.6637 | 0.7529 | 0.2195 | 0.058* | |
H1C | 0.4834 | 0.6707 | 0.1930 | 0.058* | |
C3 | 0.6955 (10) | 0.6628 (6) | 0.3514 (3) | 0.0445 (15) | |
H3A | 0.8313 | 0.6545 | 0.3255 | 0.053* | |
H3B | 0.6974 | 0.7502 | 0.3767 | 0.053* | |
C4 | 0.6799 (10) | 0.5474 (7) | 0.4048 (3) | 0.0402 (14) | |
H4A | 0.6739 | 0.4599 | 0.3797 | 0.048* | |
H4B | 0.5467 | 0.5573 | 0.4320 | 0.048* | |
C5 | 0.8739 (10) | 0.5466 (6) | 0.4563 (3) | 0.0387 (13) | |
H5A | 1.0081 | 0.5514 | 0.4292 | 0.046* | |
H5B | 0.8668 | 0.6269 | 0.4872 | 0.046* | |
N2 | 0.8728 (8) | 0.4213 (5) | 0.4996 (2) | 0.0411 (11) | |
H2A | 0.9861 | 0.4222 | 0.5291 | 0.062* | |
H2B | 0.8809 | 0.3478 | 0.4712 | 0.062* | |
H2C | 0.7506 | 0.4177 | 0.5249 | 0.062* | |
OW | 0.8602 (8) | 0.9016 (5) | 0.2011 (3) | 0.0576 (12) | |
HW1 | 0.8924 | 0.9492 | 0.2398 | 0.050* | |
HW2 | 0.9610 | 0.8420 | 0.2106 | 0.050* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S | 0.0301 (6) | 0.0376 (7) | 0.0377 (7) | 0.0008 (6) | −0.0022 (6) | −0.0016 (6) |
O1 | 0.091 (5) | 0.066 (3) | 0.060 (3) | 0.023 (3) | 0.008 (3) | 0.007 (3) |
O2 | 0.122 (7) | 0.079 (4) | 0.143 (6) | −0.001 (4) | −0.041 (6) | −0.062 (4) |
O3 | 0.036 (3) | 0.242 (10) | 0.061 (3) | 0.025 (5) | 0.012 (2) | 0.048 (5) |
O4 | 0.059 (3) | 0.071 (3) | 0.050 (2) | −0.009 (3) | 0.012 (2) | 0.001 (2) |
O1B | 0.050 (3) | 0.053 (3) | 0.054 (3) | 0.010 (2) | 0.013 (2) | 0.012 (2) |
O1A | 0.045 (2) | 0.038 (2) | 0.062 (3) | 0.0102 (19) | 0.004 (2) | 0.014 (2) |
C1 | 0.034 (3) | 0.031 (2) | 0.040 (3) | −0.002 (2) | −0.002 (2) | 0.000 (2) |
C2 | 0.031 (3) | 0.022 (2) | 0.050 (3) | −0.002 (2) | −0.010 (3) | 0.004 (2) |
N1 | 0.033 (2) | 0.035 (2) | 0.048 (2) | 0.007 (2) | −0.006 (2) | −0.007 (2) |
C3 | 0.041 (3) | 0.034 (3) | 0.059 (4) | −0.003 (3) | −0.020 (3) | 0.004 (3) |
C4 | 0.030 (3) | 0.055 (3) | 0.036 (3) | −0.002 (3) | −0.006 (2) | 0.006 (3) |
C5 | 0.038 (3) | 0.047 (3) | 0.032 (2) | −0.002 (3) | −0.003 (3) | 0.000 (2) |
N2 | 0.035 (2) | 0.054 (3) | 0.034 (2) | 0.000 (3) | −0.006 (2) | 0.001 (2) |
OW | 0.047 (2) | 0.051 (2) | 0.075 (3) | 0.003 (2) | 0.003 (2) | −0.006 (2) |
S—O3 | 1.426 (6) | C3—C4 | 1.502 (8) |
S—O2 | 1.455 (7) | C3—H3A | 0.9700 |
S—O1 | 1.452 (5) | C3—H3B | 0.9700 |
S—O4 | 1.489 (5) | C4—C5 | 1.535 (8) |
O1B—C1 | 1.319 (7) | C4—H4A | 0.9700 |
O1B—H1 | 0.8200 | C4—H4B | 0.9700 |
O1A—C1 | 1.197 (7) | C5—N2 | 1.458 (7) |
C1—C2 | 1.514 (8) | C5—H5A | 0.9700 |
C2—N1 | 1.469 (7) | C5—H5B | 0.9700 |
C2—C3 | 1.550 (8) | N2—H2A | 0.8900 |
C2—H2 | 0.9800 | N2—H2B | 0.8900 |
N1—H1A | 0.8900 | N2—H2C | 0.8900 |
N1—H1B | 0.8900 | OW—HW1 | 0.881 |
N1—H1C | 0.8900 | OW—HW2 | 0.866 |
O3—S—O2 | 113.7 (6) | C2—C3—H3A | 109.0 |
O3—S—O1 | 109.8 (5) | C4—C3—H3B | 109.0 |
O2—S—O1 | 105.1 (4) | C2—C3—H3B | 109.0 |
O3—S—O4 | 109.2 (3) | H3A—C3—H3B | 107.8 |
O2—S—O4 | 109.6 (4) | C3—C4—C5 | 111.9 (5) |
O1—S—O4 | 109.3 (3) | C3—C4—H4A | 109.2 |
C1—O1B—H1 | 109.5 | C5—C4—H4A | 109.2 |
O1A—C1—O1B | 125.3 (6) | C3—C4—H4B | 109.2 |
O1A—C1—C2 | 123.1 (5) | C5—C4—H4B | 109.2 |
O1B—C1—C2 | 111.6 (5) | H4A—C4—H4B | 107.9 |
N1—C2—C1 | 107.4 (4) | N2—C5—C4 | 110.4 (5) |
N1—C2—C3 | 109.4 (5) | N2—C5—H5A | 109.6 |
C1—C2—C3 | 112.5 (5) | C4—C5—H5A | 109.6 |
N1—C2—H2 | 109.2 | N2—C5—H5B | 109.6 |
C1—C2—H2 | 109.2 | C4—C5—H5B | 109.6 |
C3—C2—H2 | 109.2 | H5A—C5—H5B | 108.1 |
C2—N1—H1A | 109.5 | C5—N2—H2A | 109.5 |
C2—N1—H1B | 109.5 | C5—N2—H2B | 109.5 |
H1A—N1—H1B | 109.5 | H2A—N2—H2B | 109.5 |
C2—N1—H1C | 109.5 | C5—N2—H2C | 109.5 |
H1A—N1—H1C | 109.5 | H2A—N2—H2C | 109.5 |
H1B—N1—H1C | 109.5 | H2B—N2—H2C | 109.5 |
C4—C3—C2 | 112.9 (5) | HW1—OW—HW2 | 91.1 |
C4—C3—H3A | 109.0 | ||
O1A—C1—C2—N1 | −9.3 (8) | N1—C2—C3—C4 | −130.3 (5) |
O1B—C1—C2—N1 | 171.8 (5) | C1—C2—C3—C4 | 110.4 (6) |
O1A—C1—C2—C3 | 111.1 (6) | C2—C3—C4—C5 | 178.2 (5) |
O1B—C1—C2—C3 | −67.8 (7) | C3—C4—C5—N2 | −170.8 (5) |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1···O1i | 0.82 | 1.87 | 2.546 (7) | 139 |
N1—H1A···O1Aii | 0.89 | 2.21 | 2.903 (6) | 134 |
N1—H1A···O4iii | 0.89 | 2.34 | 3.003 (7) | 132 |
N1—H1B···OW | 0.89 | 1.91 | 2.790 (7) | 169 |
N1—H1C···O3ii | 0.89 | 1.99 | 2.810 (7) | 153 |
N2—H2A···O3iv | 0.89 | 1.86 | 2.729 (7) | 165 |
N2—H2B···O2v | 0.89 | 1.94 | 2.781 (8) | 158 |
N2—H2C···O2vi | 0.89 | 2.14 | 2.945 (10) | 150 |
N2—H2C···O1vi | 0.89 | 2.35 | 3.136 (8) | 148 |
OW—HW1···O4 | 0.88 | 1.88 | 2.726 (7) | 162 |
OW—HW2···O4iii | 0.87 | 2.46 | 3.195 (7) | 143 |
OW—HW2···O1Avii | 0.87 | 2.57 | 3.191 (7) | 130 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, y−1/2, −z+1/2; (iii) −x+2, y−1/2, −z+1/2; (iv) x+1/2, −y+3/2, −z+1; (v) x, y−1, z; (vi) x−1/2, −y+3/2, −z+1; (vii) x+1, y, z. |
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