Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802001150/ya6085sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802001150/ya6085Isup2.hkl |
CCDC reference: 180813
Key indicators
- Single-crystal X-ray study
- T = 295 K
- Mean (C-C) = 0.006 Å
- R factor = 0.051
- wR factor = 0.149
- Data-to-parameter ratio = 14.9
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
ABSTM_02 When printed, the submitted absorption T values will be replaced by the scaled T values. Since the ratio of scaled T's is identical to the ratio of reported T values, the scaling does not imply a change to the absorption corrections used in the study. Ratio of Tmax expected/reported 0.899 Tmax scaled 0.890 Tmin scaled 0.809 REFLT_03 From the CIF: _diffrn_reflns_theta_max 73.90 From the CIF: _reflns_number_total 3092 Count of symmetry unique reflns 1802 Completeness (_total/calc) 171.59% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 1290 Fraction of Friedel pairs measured 0.716 Are heavy atom types Z>Si present yes Please check that the estimate of the number of Friedel pairs is correct. If it is not, please give the correct count in the _publ_section_exptl_refinement section of the submitted CIF.
Data collection: CAD-4 Software (Enraf-Nonius, 1989); cell refinement: CAD-4 Software; data reduction: CORINC (Dräger & Gattow, 1971); program(s) used to solve structure: SIR92 (Altomare et al., 1994); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997).
C5H6N+·C10H15O4S−·0.5H2O | F(000) = 684 |
Mr = 320.40 | Dx = 1.311 Mg m−3 |
Monoclinic, C2 | Cu Kα radiation, λ = 1.54178 Å |
a = 24.244 (8) Å | Cell parameters from 25 reflections |
b = 6.8638 (3) Å | θ = 26–40° |
c = 10.415 (3) Å | µ = 1.94 mm−1 |
β = 110.54 (1)° | T = 295 K |
V = 1622.9 (7) Å3 | Needle, colourless |
Z = 4 | 0.45 × 0.10 × 0.06 mm |
Enraf-Nonius CAD-4 diffractometer | 2748 reflections with I > 2σ(I) |
Radiation source: rotating anode | Rint = 0.023 |
Graphite monochromator | θmax = 73.9°, θmin = 3.9° |
θ/2ω scans | h = −30→30 |
Absorption correction: ψ scan (CORINC; Dräger & Gattow, 1971) | k = −8→8 |
Tmin = 0.90, Tmax = 0.99 | l = −12→12 |
3574 measured reflections | 3 standard reflections every 60 min |
3092 independent reflections | intensity decay: 3% |
Refinement on F2 | Secondary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.051 | H-atom parameters constrained |
wR(F2) = 0.149 | w = 1/[σ2(Fo2) + (0.0968P)2 + 0.7053P] where P = (Fo2 + 2Fc2)/3 |
S = 1.03 | (Δ/σ)max < 0.001 |
3092 reflections | Δρmax = 0.40 e Å−3 |
208 parameters | Δρmin = −0.32 e Å−3 |
1 restraint | Absolute structure: Flack (1983); 1293 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.03 (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 | ||
S1 | 0.94769 (4) | 0.58774 (12) | 0.74229 (8) | 0.0534 (2) | |
O1 | 1.00896 (12) | 0.6438 (4) | 0.8012 (4) | 0.0794 (9) | |
O2 | 0.93865 (12) | 0.3813 (4) | 0.7611 (3) | 0.0629 (6) | |
O3 | 0.92056 (17) | 0.6432 (5) | 0.5997 (3) | 0.0840 (10) | |
C1 | 0.84446 (14) | 0.7061 (5) | 0.7876 (3) | 0.0480 (7) | |
C2 | 0.81672 (17) | 0.5020 (6) | 0.7399 (4) | 0.0644 (10) | |
H2A | 0.8131 | 0.4771 | 0.6456 | 0.071 (9)* | |
H2B | 0.8404 | 0.3999 | 0.7977 | 0.071 (9)* | |
C3 | 0.75499 (17) | 0.5132 (7) | 0.7541 (5) | 0.0761 (12) | |
H3A | 0.7239 | 0.4840 | 0.6678 | 0.095 (11)* | |
H3B | 0.7522 | 0.4242 | 0.8239 | 0.095 (11)* | |
C4 | 0.75192 (15) | 0.7246 (7) | 0.7960 (4) | 0.0664 (10) | |
H4 | 0.7212 | 0.7509 | 0.8349 | 0.074 (12)* | |
C5 | 0.74763 (18) | 0.8487 (9) | 0.6713 (5) | 0.0834 (14) | |
H5A | 0.7348 | 0.9802 | 0.6805 | 0.099 (12)* | |
H5B | 0.7208 | 0.7915 | 0.5875 | 0.099 (12)* | |
C6 | 0.81140 (16) | 0.8462 (7) | 0.6738 (4) | 0.0645 (10) | |
C7 | 0.81562 (13) | 0.7644 (6) | 0.8954 (3) | 0.0540 (8) | |
C8 | 0.82747 (19) | 0.9772 (7) | 0.9412 (5) | 0.0749 (11) | |
H8A | 0.8160 | 1.0604 | 0.8621 | 0.089 (9)* | |
H8B | 0.8687 | 0.9942 | 0.9921 | 0.089 (9)* | |
H8C | 0.8051 | 1.0103 | 0.9982 | 0.089 (9)* | |
C9 | 0.83463 (17) | 0.6363 (8) | 1.0219 (4) | 0.0710 (12) | |
H9A | 0.8274 | 0.5023 | 0.9949 | 0.088 (9)* | |
H9B | 0.8126 | 0.6707 | 1.0794 | 0.088 (9)* | |
H9C | 0.8759 | 0.6548 | 1.0716 | 0.088 (9)* | |
O4 | 0.83008 (13) | 0.9428 (5) | 0.6031 (3) | 0.0825 (9) | |
C10 | 0.91162 (13) | 0.7223 (5) | 0.8362 (3) | 0.0473 (7) | |
H10A | 0.9275 | 0.6805 | 0.9311 | 0.062 (8)* | |
H10B | 0.9217 | 0.8587 | 0.8339 | 0.062 (8)* | |
N12 | 0.91664 (12) | 0.9774 (5) | 0.4569 (3) | 0.0584 (8) | |
H12 | 0.9091 | 0.9095 | 0.5178 | 0.11 (2)* | |
C13 | 0.90693 (17) | 1.1627 (7) | 0.4748 (4) | 0.0656 (10) | |
H13 | 0.8944 | 1.2000 | 0.5459 | 0.111 (19)* | |
C14 | 0.91546 (18) | 1.2999 (7) | 0.3880 (5) | 0.0741 (11) | |
H14 | 0.9081 | 1.4307 | 0.3988 | 0.13 (2)* | |
C15 | 0.93484 (17) | 1.2427 (6) | 0.2850 (5) | 0.0671 (10) | |
H15 | 0.9406 | 1.3341 | 0.2250 | 0.108 (19)* | |
C16 | 0.94561 (15) | 1.0480 (6) | 0.2714 (4) | 0.0638 (11) | |
H16 | 0.9592 | 1.0064 | 0.2029 | 0.077 (13)* | |
C17 | 0.93612 (16) | 0.9180 (6) | 0.3594 (4) | 0.0606 (9) | |
H17 | 0.9433 | 0.7863 | 0.3513 | 0.099 (17)* | |
O1W | 1.0000 | 0.1558 (8) | 1.0000 | 0.132 (3) | |
H1W | 0.9801 | 0.2459 | 0.9205 | 0.197* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0674 (4) | 0.0458 (4) | 0.0595 (4) | 0.0040 (4) | 0.0377 (3) | 0.0014 (4) |
O1 | 0.0691 (15) | 0.0678 (18) | 0.124 (2) | −0.0028 (12) | 0.0623 (17) | −0.0096 (16) |
O2 | 0.0762 (15) | 0.0471 (14) | 0.0724 (16) | 0.0034 (11) | 0.0348 (13) | 0.0029 (12) |
O3 | 0.140 (3) | 0.0671 (18) | 0.0626 (16) | 0.0212 (17) | 0.0577 (18) | 0.0035 (13) |
C1 | 0.0484 (15) | 0.0542 (19) | 0.0446 (15) | −0.0022 (13) | 0.0202 (13) | 0.0015 (14) |
C2 | 0.063 (2) | 0.071 (2) | 0.062 (2) | −0.0207 (18) | 0.0261 (17) | −0.0127 (19) |
C3 | 0.059 (2) | 0.090 (3) | 0.080 (3) | −0.026 (2) | 0.0241 (19) | −0.004 (2) |
C4 | 0.0464 (17) | 0.085 (3) | 0.070 (2) | −0.0003 (17) | 0.0235 (15) | 0.009 (2) |
C5 | 0.055 (2) | 0.115 (4) | 0.078 (3) | 0.007 (2) | 0.0202 (19) | 0.026 (3) |
C6 | 0.0587 (19) | 0.079 (3) | 0.056 (2) | 0.0051 (17) | 0.0206 (16) | 0.0131 (18) |
C7 | 0.0494 (16) | 0.063 (2) | 0.0547 (18) | 0.0025 (14) | 0.0246 (14) | −0.0009 (15) |
C8 | 0.077 (2) | 0.071 (3) | 0.089 (3) | 0.006 (2) | 0.044 (2) | −0.015 (2) |
C9 | 0.0617 (19) | 0.105 (4) | 0.0527 (19) | 0.002 (2) | 0.0281 (16) | 0.0085 (19) |
O4 | 0.0777 (16) | 0.097 (2) | 0.0785 (17) | 0.0044 (16) | 0.0341 (14) | 0.0351 (17) |
C10 | 0.0519 (15) | 0.0475 (16) | 0.0481 (15) | −0.0005 (13) | 0.0246 (13) | −0.0032 (14) |
N12 | 0.0553 (15) | 0.069 (2) | 0.0500 (15) | −0.0035 (14) | 0.0172 (12) | 0.0065 (15) |
C13 | 0.061 (2) | 0.079 (3) | 0.062 (2) | −0.0072 (18) | 0.0283 (17) | −0.0130 (19) |
C14 | 0.070 (2) | 0.052 (2) | 0.104 (3) | −0.0081 (18) | 0.036 (2) | −0.013 (2) |
C15 | 0.061 (2) | 0.061 (2) | 0.083 (3) | −0.0112 (17) | 0.0294 (19) | 0.009 (2) |
C16 | 0.0599 (18) | 0.079 (3) | 0.0568 (19) | 0.0027 (17) | 0.0260 (15) | −0.0011 (18) |
C17 | 0.067 (2) | 0.054 (2) | 0.063 (2) | 0.0037 (16) | 0.0251 (17) | 0.0036 (17) |
O1W | 0.230 (8) | 0.061 (3) | 0.076 (3) | 0.000 | 0.019 (4) | 0.000 |
S1—O1 | 1.446 (3) | C4—C7 | 1.552 (5) |
S1—O2 | 1.458 (3) | C5—C6 | 1.537 (5) |
S1—O3 | 1.448 (3) | C6—O4 | 1.192 (5) |
S1—C10 | 1.782 (3) | C7—C9 | 1.515 (5) |
C1—C6 | 1.518 (5) | C7—C8 | 1.532 (6) |
C1—C10 | 1.530 (4) | N12—C13 | 1.318 (6) |
C1—C2 | 1.558 (5) | N12—C17 | 1.326 (5) |
C1—C7 | 1.569 (4) | C13—C14 | 1.371 (7) |
C2—C3 | 1.557 (5) | C14—C15 | 1.371 (6) |
C3—C4 | 1.524 (7) | C15—C16 | 1.378 (6) |
C4—C5 | 1.526 (6) | C16—C17 | 1.355 (6) |
O1—S1—O3 | 113.2 (2) | C4—C5—C6 | 102.2 (3) |
O1—S1—O2 | 112.47 (18) | O4—C6—C1 | 128.6 (3) |
O3—S1—O2 | 110.98 (18) | O4—C6—C5 | 125.5 (4) |
O1—S1—C10 | 104.96 (16) | C1—C6—C5 | 105.8 (3) |
O2—S1—C10 | 107.72 (15) | C9—C7—C8 | 108.4 (3) |
O3—S1—C10 | 107.02 (17) | C9—C7—C4 | 113.9 (3) |
C6—C1—C10 | 114.9 (3) | C8—C7—C4 | 114.2 (3) |
C6—C1—C2 | 105.7 (3) | C9—C7—C1 | 113.5 (3) |
C10—C1—C2 | 117.5 (3) | C8—C7—C1 | 112.6 (3) |
C6—C1—C7 | 98.7 (3) | C4—C7—C1 | 93.8 (3) |
C10—C1—C7 | 115.8 (3) | C1—C10—S1 | 116.8 (2) |
C2—C1—C7 | 101.9 (3) | C13—N12—C17 | 122.3 (4) |
C3—C2—C1 | 104.3 (3) | N12—C13—C14 | 119.6 (4) |
C4—C3—C2 | 102.7 (3) | C15—C14—C13 | 119.5 (4) |
C3—C4—C5 | 106.5 (4) | C14—C15—C16 | 119.1 (4) |
C3—C4—C7 | 102.8 (3) | C17—C16—C15 | 119.1 (4) |
C5—C4—C7 | 102.9 (3) | N12—C17—C16 | 120.4 (4) |
C6—C1—C2—C3 | −72.2 (4) | C6—C1—C7—C9 | 174.4 (3) |
C10—C1—C2—C3 | 158.1 (3) | C10—C1—C7—C9 | −62.5 (4) |
C7—C1—C2—C3 | 30.5 (4) | C2—C1—C7—C9 | 66.2 (4) |
C1—C2—C3—C4 | 4.6 (4) | C6—C1—C7—C8 | −62.0 (4) |
C2—C3—C4—C5 | 69.0 (4) | C10—C1—C7—C8 | 61.2 (4) |
C2—C3—C4—C7 | −38.8 (4) | C2—C1—C7—C8 | −170.1 (3) |
C3—C4—C5—C6 | −76.7 (4) | C6—C1—C7—C4 | 56.2 (3) |
C7—C4—C5—C6 | 31.0 (5) | C10—C1—C7—C4 | 179.4 (3) |
C10—C1—C6—O4 | 13.5 (6) | C2—C1—C7—C4 | −51.9 (3) |
C2—C1—C6—O4 | −117.7 (5) | C6—C1—C10—S1 | −85.5 (4) |
C7—C1—C6—O4 | 137.2 (5) | C2—C1—C10—S1 | 39.7 (4) |
C10—C1—C6—C5 | −163.6 (3) | C7—C1—C10—S1 | 160.3 (2) |
C2—C1—C6—C5 | 65.2 (4) | O1—S1—C10—C1 | 174.7 (3) |
C7—C1—C6—C5 | −39.8 (4) | O3—S1—C10—C1 | 54.2 (3) |
C4—C5—C6—O4 | −171.3 (5) | O2—S1—C10—C1 | −65.2 (3) |
C4—C5—C6—C1 | 5.9 (5) | C17—N12—C13—C14 | 1.9 (6) |
C3—C4—C7—C9 | −61.6 (4) | N12—C13—C14—C15 | −1.0 (6) |
C5—C4—C7—C9 | −172.1 (4) | C13—C14—C15—C16 | −0.3 (6) |
C3—C4—C7—C8 | 173.1 (3) | C14—C15—C16—C17 | 0.7 (6) |
C5—C4—C7—C8 | 62.6 (4) | C13—N12—C17—C16 | −1.5 (6) |
C3—C4—C7—C1 | 56.2 (3) | C15—C16—C17—N12 | 0.1 (6) |
C5—C4—C7—C1 | −54.3 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N12—H12···O3 | 0.86 | 2.00 | 2.718 (5) | 141 |
O1W—H1W···O2 | 1.01 | 1.86 | 2.864 (4) | 172 |