Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804007238/ci6349sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804007238/ci6349Isup2.hkl |
CCDC reference: 239144
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.006 Å
- R factor = 0.039
- wR factor = 0.098
- Data-to-parameter ratio = 9.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... N3
Alert level C STRVA01_ALERT_4_C Flack test results are ambiguous. From the CIF: _refine_ls_abs_structure_Flack 0.420 From the CIF: _refine_ls_abs_structure_Flack_su 0.130 PLAT033_ALERT_2_C Flack Parameter Value Deviates from Zero ....... 0.42 PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT340_ALERT_3_C Low Bond Precision on C-C bonds (x 1000) Ang ... 6
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 26.94 From the CIF: _reflns_number_total 1288 Count of symmetry unique reflns 1153 Completeness (_total/calc) 111.71% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 135 Fraction of Friedel pairs measured 0.117 Are heavy atom types Z>Si present yes
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 4 ALERT level C = Check and explain 1 ALERT level G = General alerts; check 1 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 (Enraf Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); program(s) used to solve structure: SHELXS97 (Sheldrick, 1990); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
2C5H14N2O22+·Cl−·NO3−·SO42− | F(000) = 488 |
Mr = 461.88 | Dx = 1.542 Mg m−3 Dm = 1.540 Mg m−3 Dm measured by Flotation technique using mixture of carbon tetrachloride and xylene |
Monoclinic, C2 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: C 2y | Cell parameters from 25 reflections |
a = 13.872 (5) Å | θ = 9.2–14.3° |
b = 9.578 (6) Å | µ = 0.36 mm−1 |
c = 9.178 (1) Å | T = 293 K |
β = 125.350 (14)° | Block, colorless |
V = 994.6 (7) Å3 | 0.3 × 0.2 × 0.15 mm |
Z = 2 |
MACH3-Nonius sealed tube diffractometer | 1125 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.021 |
Graphite monochromator | θmax = 26.9°, θmin = 2.7° |
ω–2θ scans | h = −17→15 |
Absorption correction: ψ scan [North et al., 1968] | k = −1→12 |
Tmin = 0.902, Tmax = 0.999 | l = −1→11 |
1524 measured reflections | 3 standard reflections every 60 min |
1288 independent reflections | intensity decay: none |
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)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.097 | w = 1/[σ2(Fo2) + (0.0351P)2 + 1.3881P] where P = (Fo2 + 2Fc2)/3 |
S = 1.18 | (Δ/σ)max < 0.001 |
1288 reflections | Δρmax = 0.30 e Å−3 |
133 parameters | Δρmin = −0.29 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 214 Friedels pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.01 (13) |
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 | 0.7128 (3) | −0.3802 (3) | 0.3590 (4) | 0.0386 (8) | |
O1B | 0.5376 (2) | −0.2727 (4) | 0.2054 (4) | 0.0372 (7) | |
H1 | 0.507 (4) | −0.358 (6) | 0.174 (6) | 0.041 (14)* | |
C1 | 0.6545 (3) | −0.2753 (4) | 0.3167 (5) | 0.0243 (8) | |
C2 | 0.7064 (3) | −0.1302 (4) | 0.3816 (5) | 0.0253 (9) | |
H2 | 0.6732 | −0.0891 | 0.4415 | 0.030* | |
N1 | 0.8367 (3) | −0.1465 (4) | 0.5155 (4) | 0.0303 (8) | |
H1D | 0.8674 | −0.1878 | 0.4641 | 0.046* | |
H1B | 0.8507 | −0.1987 | 0.6061 | 0.046* | |
H1C | 0.8696 | −0.0629 | 0.5559 | 0.046* | |
C3 | 0.6782 (3) | −0.0345 (4) | 0.2295 (5) | 0.0295 (9) | |
H3A | 0.7185 | 0.0537 | 0.2796 | 0.035* | |
H3B | 0.5939 | −0.0158 | 0.1557 | 0.035* | |
C4 | 0.7130 (3) | −0.0921 (5) | 0.1101 (5) | 0.0289 (8) | |
H4A | 0.7978 | −0.1065 | 0.1806 | 0.035* | |
H4B | 0.6747 | −0.1815 | 0.0609 | 0.035* | |
C5 | 0.6766 (4) | 0.0089 (5) | −0.0401 (5) | 0.0378 (10) | |
H5A | 0.5937 | 0.0320 | −0.1001 | 0.045* | |
H5B | 0.7218 | 0.0943 | 0.0099 | 0.045* | |
N2 | 0.6946 (3) | −0.0470 (5) | −0.1724 (4) | 0.0392 (9) | |
H2A | 0.6726 | 0.0167 | −0.2570 | 0.059* | |
H2B | 0.6514 | −0.1239 | −0.2217 | 0.059* | |
H2C | 0.7706 | −0.0674 | −0.1186 | 0.059* | |
Cl1 | 0.5000 | −0.86710 (18) | 0.5000 | 0.0425 (4) | |
N3 | 1.0000 | −0.8399 (6) | 0.5000 | 0.0340 (12) | |
O1 | 1.0000 | −0.9673 (6) | 0.5000 | 0.0615 (16) | |
O2 | 0.9061 (4) | −0.7758 (6) | 0.4130 (6) | 0.0829 (16) | |
S1 | 0.5000 | −0.60577 (15) | 0.0000 | 0.0265 (3) | |
O3 | 0.5986 (3) | −0.6916 (4) | 0.1386 (4) | 0.0419 (8) | |
O4 | 0.4534 (2) | −0.5163 (4) | 0.0774 (4) | 0.0364 (7) |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1A | 0.0293 (15) | 0.0269 (16) | 0.0448 (17) | 0.0000 (14) | 0.0130 (13) | −0.0001 (15) |
O1B | 0.0244 (13) | 0.0298 (17) | 0.0392 (17) | −0.0022 (14) | 0.0081 (12) | −0.0067 (15) |
C1 | 0.0279 (18) | 0.025 (2) | 0.0208 (16) | −0.0048 (18) | 0.0147 (15) | −0.0030 (16) |
C2 | 0.0260 (16) | 0.027 (2) | 0.0220 (15) | 0.0000 (16) | 0.0131 (14) | −0.0007 (15) |
N1 | 0.0266 (15) | 0.0306 (19) | 0.0211 (14) | −0.0045 (14) | 0.0064 (12) | −0.0030 (13) |
C3 | 0.0279 (17) | 0.027 (2) | 0.0276 (18) | 0.0002 (18) | 0.0128 (15) | 0.0023 (18) |
C4 | 0.0302 (17) | 0.031 (2) | 0.0223 (16) | −0.0014 (19) | 0.0132 (14) | 0.0072 (18) |
C5 | 0.041 (2) | 0.044 (3) | 0.031 (2) | 0.000 (2) | 0.0224 (19) | 0.009 (2) |
N2 | 0.0373 (17) | 0.054 (3) | 0.0284 (17) | 0.004 (2) | 0.0204 (15) | 0.0075 (18) |
Cl1 | 0.0271 (8) | 0.0399 (10) | 0.0446 (9) | 0.000 | 0.0116 (7) | 0.000 |
N3 | 0.034 (3) | 0.031 (3) | 0.048 (3) | 0.000 | 0.030 (3) | 0.000 |
O1 | 0.065 (3) | 0.035 (3) | 0.102 (4) | 0.000 | 0.058 (3) | 0.000 |
O2 | 0.077 (3) | 0.094 (4) | 0.108 (3) | 0.048 (3) | 0.071 (3) | 0.054 (3) |
S1 | 0.0263 (6) | 0.0247 (7) | 0.0186 (6) | 0.000 | 0.0072 (5) | 0.000 |
O3 | 0.0468 (17) | 0.0401 (19) | 0.0228 (13) | 0.0164 (16) | 0.0109 (13) | 0.0069 (14) |
O4 | 0.0292 (13) | 0.0411 (18) | 0.0411 (15) | −0.0060 (14) | 0.0215 (13) | −0.0115 (15) |
O1A—C1 | 1.205 (5) | C4—H4B | 0.9700 |
O1B—C1 | 1.325 (4) | C5—N2 | 1.474 (6) |
O1B—H1 | 0.89 (6) | C5—H5A | 0.9700 |
C1—C2 | 1.519 (5) | C5—H5B | 0.9700 |
C2—N1 | 1.494 (4) | N2—H2A | 0.8900 |
C2—C3 | 1.520 (5) | N2—H2B | 0.8900 |
C2—H2 | 0.9800 | N2—H2C | 0.8900 |
N1—H1D | 0.8900 | N3—O1 | 1.220 (8) |
N1—H1B | 0.8900 | N3—O2 | 1.228 (5) |
N1—H1C | 0.8900 | N3—O2i | 1.228 (5) |
C3—C4 | 1.533 (5) | S1—O3ii | 1.466 (3) |
C3—H3A | 0.9700 | S1—O3 | 1.466 (3) |
C3—H3B | 0.9700 | S1—O4 | 1.479 (3) |
C4—C5 | 1.512 (6) | S1—O4ii | 1.479 (3) |
C4—H4A | 0.9700 | ||
C1—O1B—H1 | 112 (3) | C5—C4—H4B | 109.6 |
O1A—C1—O1B | 123.9 (4) | C3—C4—H4B | 109.6 |
O1A—C1—C2 | 124.0 (3) | H4A—C4—H4B | 108.1 |
O1B—C1—C2 | 112.1 (3) | N2—C5—C4 | 113.1 (4) |
N1—C2—C1 | 107.5 (3) | N2—C5—H5A | 109.0 |
N1—C2—C3 | 111.4 (3) | C4—C5—H5A | 109.0 |
C1—C2—C3 | 112.3 (3) | N2—C5—H5B | 109.0 |
N1—C2—H2 | 108.5 | C4—C5—H5B | 109.0 |
C1—C2—H2 | 108.5 | H5A—C5—H5B | 107.8 |
C3—C2—H2 | 108.5 | C5—N2—H2A | 109.5 |
C2—N1—H1D | 109.5 | C5—N2—H2B | 109.5 |
C2—N1—H1B | 109.5 | H2A—N2—H2B | 109.5 |
H1D—N1—H1B | 109.5 | C5—N2—H2C | 109.5 |
C2—N1—H1C | 109.5 | H2A—N2—H2C | 109.5 |
H1D—N1—H1C | 109.5 | H2B—N2—H2C | 109.5 |
H1B—N1—H1C | 109.5 | O1—N3—O2 | 120.0 (4) |
C2—C3—C4 | 114.8 (3) | O1—N3—O2i | 120.0 (4) |
C2—C3—H3A | 108.6 | O2—N3—O2i | 119.9 (7) |
C4—C3—H3A | 108.6 | O3ii—S1—O3 | 111.8 (3) |
C2—C3—H3B | 108.6 | O3ii—S1—O4 | 107.10 (17) |
C4—C3—H3B | 108.6 | O3—S1—O4 | 110.81 (17) |
H3A—C3—H3B | 107.5 | O3ii—S1—O4ii | 110.81 (17) |
C5—C4—C3 | 110.1 (4) | O3—S1—O4ii | 107.10 (17) |
C5—C4—H4A | 109.6 | O4—S1—O4ii | 109.2 (3) |
C3—C4—H4A | 109.6 | ||
O1A—C1—C2—N1 | −5.3 (5) | N1—C2—C3—C4 | 66.7 (4) |
O1B—C1—C2—N1 | 175.9 (3) | C1—C2—C3—C4 | −53.9 (4) |
O1A—C1—C2—C3 | 117.5 (4) | C2—C3—C4—C5 | 177.8 (3) |
O1B—C1—C2—C3 | −61.3 (4) | C3—C4—C5—N2 | −173.2 (3) |
Symmetry codes: (i) −x+2, y, −z+1; (ii) −x+1, y, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
O1B—H1···O4 | 0.89 (6) | 1.69 (6) | 2.569 (5) | 167 (5) |
N1—H1B···O3iii | 0.89 | 2.02 | 2.788 (4) | 144 |
N1—H1C···O1iv | 0.89 | 2.33 | 2.911 (5) | 123 |
N1—H1C···O1Aiii | 0.89 | 2.45 | 3.036 (5) | 124 |
N1—H1D···Cl1v | 0.89 | 2.40 | 3.160 (4) | 144 |
N2—H2A···Cl1vi | 0.89 | 2.40 | 3.147 (4) | 141 |
N2—H2B···O2vii | 0.89 | 2.05 | 2.839 (6) | 147 |
N2—H2C···O4v | 0.89 | 2.15 | 2.951 (5) | 149 |
N2—H2C···O3vii | 0.89 | 2.26 | 3.036 (5) | 145 |
Symmetry codes: (iii) −x+3/2, y+1/2, −z+1; (iv) x, y+1, z; (v) x+1/2, y+1/2, z; (vi) x, y+1, z−1; (vii) −x+3/2, y+1/2, −z. |
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