Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536802010656/ya6110sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536802010656/ya6110Isup2.hkl |
CCDC reference: 189911
Key indicators
- Single-crystal X-ray study
- T = 105 K
- Mean (C-C) = 0.002 Å
- R factor = 0.029
- wR factor = 0.086
- Data-to-parameter ratio = 40.1
checkCIF results
No syntax errors found ADDSYM reports no extra symmetry General Notes
REFLT_03 From the CIF: _diffrn_reflns_theta_max 37.60 From the CIF: _reflns_number_total 9018 Count of symmetry unique reflns 5304 Completeness (_total/calc) 170.02% TEST3: Check Friedels for noncentro structure Estimate of Friedel pairs measured 3714 Fraction of Friedel pairs measured 0.700 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: SMART (Bruker, 1998); cell refinement: SAINT (Bruker, 1998); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: PLATON (Spek, 1999); software used to prepare material for publication: SHELXL97.
C5H12NO2S+·ClO4−·C5H11NO2S·H2O | F(000) = 440 |
Mr = 416.89 | Dx = 1.493 Mg m−3 Dm = 1.472 Mg m−3 Dm measured by flotation in carbon tetrachloride and xylene |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71070 Å |
a = 11.3720 (15) Å | Cell parameters from 7529 reflections |
b = 5.5876 (8) Å | θ = 2.7–37.6° |
c = 15.323 (2) Å | µ = 0.48 mm−1 |
β = 107.782 (5)° | T = 105 K |
V = 927.1 (2) Å3 | Plate, colorless |
Z = 2 | 0.8 × 0.4 × 0.2 mm |
Bruker SMART CCD diffractometer | 9018 independent reflections |
Radiation source: fine-focus sealed tube | 8635 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 8.33 pixels mm-1 | θmax = 37.6°, θmin = 1.4° |
ω scans | h = −19→18 |
Absorption correction: multi-scan (SADABS; Sheldrick, 1996) | k = −9→9 |
Tmin = 0.677, Tmax = 0.913 | l = −26→26 |
17119 measured reflections |
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)] = 0.029 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.086 | w = 1/[σ2(Fo2) + (0.0501P)2 + 0.1368P] where P = (Fo2 + 2Fc2)/3 |
S = 1.07 | (Δ/σ)max = 0.002 |
9018 reflections | Δρmax = 0.62 e Å−3 |
225 parameters | Δρmin = −0.60 e Å−3 |
1 restraint | Absolute structure: Flack (1983), 3692 Friedel pairs |
Primary atom site location: structure-invariant direct methods | Absolute structure parameter: 0.05 (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 | ||
Cl | 0.521360 (19) | 0.65794 (4) | 0.605643 (14) | 0.01177 (4) | |
O1 | 0.56965 (9) | 0.6632 (2) | 0.52947 (6) | 0.02188 (15) | |
O2 | 0.57325 (8) | 0.45792 (17) | 0.66442 (6) | 0.01972 (15) | |
O3 | 0.55157 (8) | 0.87874 (17) | 0.65699 (6) | 0.02051 (15) | |
O4 | 0.38773 (7) | 0.63508 (16) | 0.57392 (6) | 0.01849 (14) | |
O1A | 0.11741 (7) | 1.42468 (17) | 0.59291 (6) | 0.01835 (14) | |
O1B | 0.12625 (8) | 1.41499 (17) | 0.74137 (6) | 0.01938 (14) | |
C11 | 0.16270 (9) | 1.35608 (17) | 0.67458 (7) | 0.01322 (14) | |
C12 | 0.27300 (8) | 1.18507 (17) | 0.69587 (6) | 0.01156 (14) | |
H12 | 0.2478 | 1.0303 | 0.7144 | 0.014* | |
N11 | 0.30826 (7) | 1.15005 (18) | 0.61010 (5) | 0.01364 (12) | |
H11A | 0.2435 | 1.0955 | 0.5657 | 0.020* | |
H11B | 0.3697 | 1.0448 | 0.6206 | 0.020* | |
H11C | 0.3325 | 1.2891 | 0.5930 | 0.020* | |
C13 | 0.38321 (9) | 1.27857 (19) | 0.77340 (7) | 0.01450 (15) | |
H13A | 0.4587 | 1.2132 | 0.7662 | 0.017* | |
H13B | 0.3870 | 1.4514 | 0.7687 | 0.017* | |
C14 | 0.37581 (11) | 1.2128 (2) | 0.86843 (7) | 0.01780 (18) | |
H14A | 0.2983 | 1.2714 | 0.8743 | 0.021* | |
H14B | 0.4421 | 1.2932 | 0.9143 | 0.021* | |
S11 | 0.38650 (3) | 0.89384 (6) | 0.891692 (18) | 0.01910 (5) | |
C15 | 0.54450 (12) | 0.8390 (3) | 0.89445 (9) | 0.0247 (2) | |
H15A | 0.5636 | 0.6725 | 0.9063 | 0.037* | |
H15B | 0.5992 | 0.9336 | 0.9421 | 0.037* | |
H15C | 0.5545 | 0.8819 | 0.8365 | 0.037* | |
O2A | 0.84774 (9) | −0.28937 (18) | 0.63593 (8) | 0.0265 (2) | |
O2B | 1.02666 (8) | −0.18599 (18) | 0.74094 (7) | 0.02335 (17) | |
H2B | 1.0484 | −0.3205 | 0.7310 | 0.035* | |
C21 | 0.91375 (9) | −0.14753 (19) | 0.68887 (7) | 0.01533 (16) | |
C22 | 0.86929 (9) | 0.10138 (18) | 0.70495 (7) | 0.01375 (15) | |
H22 | 0.9359 | 0.2167 | 0.7099 | 0.016* | |
N21 | 0.76185 (8) | 0.1652 (2) | 0.62420 (6) | 0.01641 (14) | |
H21A | 0.7345 | 0.3101 | 0.6324 | 0.025* | |
H21B | 0.7018 | 0.0584 | 0.6182 | 0.025* | |
H21C | 0.7852 | 0.1650 | 0.5738 | 0.025* | |
C23 | 0.83376 (10) | 0.1067 (2) | 0.79420 (7) | 0.01655 (17) | |
H23A | 0.7499 | 0.0487 | 0.7820 | 0.020* | |
H23B | 0.8880 | 0.0009 | 0.8389 | 0.020* | |
C24 | 0.84328 (11) | 0.3598 (2) | 0.83367 (8) | 0.01893 (18) | |
H24A | 0.7990 | 0.4685 | 0.7855 | 0.023* | |
H24B | 0.9294 | 0.4078 | 0.8532 | 0.023* | |
S21 | 0.78281 (3) | 0.39046 (6) | 0.92960 (2) | 0.02403 (6) | |
C25 | 0.87637 (14) | 0.1791 (3) | 1.00959 (9) | 0.0299 (3) | |
H25A | 0.8527 | 0.1787 | 1.0646 | 0.045* | |
H25B | 0.9617 | 0.2236 | 1.0240 | 0.045* | |
H25C | 0.8647 | 0.0221 | 0.9829 | 0.045* | |
OW | 0.12675 (8) | 1.83730 (16) | 0.50284 (6) | 0.01686 (13) | |
H1W | 0.115 (2) | 1.718 (4) | 0.5277 (16) | 0.027 (5)* | |
H2W | 0.058 (2) | 1.875 (5) | 0.4691 (15) | 0.032 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl | 0.01113 (8) | 0.01132 (8) | 0.01329 (8) | 0.00050 (6) | 0.00437 (6) | 0.00080 (7) |
O1 | 0.0263 (4) | 0.0247 (4) | 0.0196 (3) | 0.0015 (3) | 0.0143 (3) | 0.0023 (3) |
O2 | 0.0186 (3) | 0.0191 (4) | 0.0226 (4) | 0.0075 (3) | 0.0079 (3) | 0.0091 (3) |
O3 | 0.0206 (3) | 0.0160 (4) | 0.0227 (4) | −0.0016 (3) | 0.0032 (3) | −0.0062 (3) |
O4 | 0.0095 (3) | 0.0165 (4) | 0.0276 (4) | −0.0004 (2) | 0.0029 (2) | 0.0002 (3) |
O1A | 0.0151 (3) | 0.0201 (4) | 0.0179 (3) | 0.0041 (3) | 0.0020 (2) | 0.0041 (3) |
O1B | 0.0188 (3) | 0.0205 (4) | 0.0212 (3) | 0.0073 (3) | 0.0095 (3) | 0.0009 (3) |
C11 | 0.0108 (3) | 0.0114 (4) | 0.0175 (4) | 0.0008 (2) | 0.0043 (3) | 0.0008 (3) |
C12 | 0.0117 (3) | 0.0111 (4) | 0.0122 (3) | 0.0010 (2) | 0.0041 (2) | 0.0001 (3) |
N11 | 0.0141 (3) | 0.0138 (3) | 0.0138 (3) | 0.0017 (3) | 0.0054 (2) | −0.0007 (3) |
C13 | 0.0140 (4) | 0.0147 (4) | 0.0135 (3) | −0.0004 (3) | 0.0023 (3) | 0.0007 (3) |
C14 | 0.0211 (4) | 0.0188 (5) | 0.0131 (4) | 0.0034 (3) | 0.0047 (3) | 0.0000 (3) |
S11 | 0.01965 (11) | 0.02054 (12) | 0.01728 (10) | 0.00042 (9) | 0.00588 (8) | 0.00526 (9) |
C15 | 0.0231 (5) | 0.0283 (6) | 0.0230 (5) | 0.0080 (4) | 0.0073 (4) | 0.0064 (4) |
O2A | 0.0213 (4) | 0.0207 (4) | 0.0327 (5) | 0.0017 (3) | 0.0009 (3) | −0.0102 (3) |
O2B | 0.0169 (3) | 0.0203 (4) | 0.0280 (4) | 0.0074 (3) | −0.0003 (3) | −0.0056 (3) |
C21 | 0.0140 (4) | 0.0156 (4) | 0.0169 (4) | 0.0018 (3) | 0.0054 (3) | −0.0017 (3) |
C22 | 0.0124 (3) | 0.0138 (4) | 0.0151 (4) | 0.0014 (3) | 0.0043 (3) | −0.0003 (3) |
N21 | 0.0144 (3) | 0.0186 (4) | 0.0163 (3) | 0.0032 (3) | 0.0049 (2) | 0.0030 (3) |
C23 | 0.0196 (4) | 0.0158 (4) | 0.0149 (4) | 0.0016 (3) | 0.0064 (3) | −0.0006 (3) |
C24 | 0.0215 (4) | 0.0176 (5) | 0.0181 (4) | 0.0013 (3) | 0.0066 (3) | −0.0035 (3) |
S21 | 0.02551 (13) | 0.02760 (15) | 0.01996 (11) | 0.00908 (11) | 0.00839 (9) | −0.00393 (10) |
C25 | 0.0317 (6) | 0.0393 (8) | 0.0181 (4) | 0.0092 (5) | 0.0066 (4) | 0.0022 (5) |
OW | 0.0155 (3) | 0.0173 (3) | 0.0165 (3) | 0.0003 (2) | 0.0029 (2) | 0.0017 (2) |
Cl—O1 | 1.4339 (8) | O2A—C21 | 1.2156 (14) |
Cl—O2 | 1.4435 (9) | O2B—C21 | 1.3060 (14) |
Cl—O3 | 1.4471 (9) | O2B—H2B | 0.8200 |
Cl—O4 | 1.4529 (8) | C21—C22 | 1.5254 (15) |
O1A—C11 | 1.2587 (13) | C22—N21 | 1.4925 (13) |
O1B—C11 | 1.2596 (13) | C22—C23 | 1.5400 (14) |
C11—C12 | 1.5306 (13) | C22—H22 | 0.9800 |
C12—N11 | 1.4994 (12) | N21—H21A | 0.8900 |
C12—C13 | 1.5316 (14) | N21—H21B | 0.8900 |
C12—H12 | 0.9800 | N21—H21C | 0.8900 |
N11—H11A | 0.8900 | C23—C24 | 1.5290 (16) |
N11—H11B | 0.8900 | C23—H23A | 0.9700 |
N11—H11C | 0.8900 | C23—H23B | 0.9700 |
C13—C14 | 1.5289 (15) | C24—S21 | 1.8112 (11) |
C13—H13A | 0.9700 | C24—H24A | 0.9700 |
C13—H13B | 0.9700 | C24—H24B | 0.9700 |
C14—S11 | 1.8140 (12) | S21—C25 | 1.7979 (15) |
C14—H14A | 0.9700 | C25—H25A | 0.9600 |
C14—H14B | 0.9700 | C25—H25B | 0.9600 |
S11—C15 | 1.8105 (14) | C25—H25C | 0.9600 |
C15—H15A | 0.9600 | OW—H1W | 0.80 (2) |
C15—H15B | 0.9600 | OW—H2W | 0.82 (2) |
C15—H15C | 0.9600 | ||
O1—Cl—O2 | 109.79 (6) | H15A—C15—H15C | 109.5 |
O1—Cl—O3 | 109.80 (6) | H15B—C15—H15C | 109.5 |
O2—Cl—O3 | 109.69 (6) | C21—O2B—H2B | 109.5 |
O1—Cl—O4 | 110.55 (5) | O2A—C21—O2B | 126.30 (11) |
O2—Cl—O4 | 109.10 (5) | O2A—C21—C22 | 122.32 (10) |
O3—Cl—O4 | 107.89 (5) | O2B—C21—C22 | 111.34 (9) |
O1B—C11—O1A | 126.29 (9) | N21—C22—C21 | 108.16 (9) |
O1B—C11—C12 | 116.20 (9) | N21—C22—C23 | 111.17 (8) |
O1A—C11—C12 | 117.51 (9) | C21—C22—C23 | 110.54 (8) |
N11—C12—C11 | 108.41 (7) | N21—C22—H22 | 109.0 |
N11—C12—C13 | 110.47 (8) | C21—C22—H22 | 109.0 |
C11—C12—C13 | 112.06 (8) | C23—C22—H22 | 109.0 |
N11—C12—H12 | 108.6 | C22—N21—H21A | 109.5 |
C11—C12—H12 | 108.6 | C22—N21—H21B | 109.5 |
C13—C12—H12 | 108.6 | H21A—N21—H21B | 109.5 |
C12—N11—H11A | 109.5 | C22—N21—H21C | 109.5 |
C12—N11—H11B | 109.5 | H21A—N21—H21C | 109.5 |
H11A—N11—H11B | 109.5 | H21B—N21—H21C | 109.5 |
C12—N11—H11C | 109.5 | C24—C23—C22 | 111.28 (9) |
H11A—N11—H11C | 109.5 | C24—C23—H23A | 109.4 |
H11B—N11—H11C | 109.5 | C22—C23—H23A | 109.4 |
C14—C13—C12 | 112.74 (9) | C24—C23—H23B | 109.4 |
C14—C13—H13A | 109.0 | C22—C23—H23B | 109.4 |
C12—C13—H13A | 109.0 | H23A—C23—H23B | 108.0 |
C14—C13—H13B | 109.0 | C23—C24—S21 | 114.20 (8) |
C12—C13—H13B | 109.0 | C23—C24—H24A | 108.7 |
H13A—C13—H13B | 107.8 | S21—C24—H24A | 108.7 |
C13—C14—S11 | 113.80 (8) | C23—C24—H24B | 108.7 |
C13—C14—H14A | 108.8 | S21—C24—H24B | 108.7 |
S11—C14—H14A | 108.8 | H24A—C24—H24B | 107.6 |
C13—C14—H14B | 108.8 | C25—S21—C24 | 101.47 (6) |
S11—C14—H14B | 108.8 | S21—C25—H25A | 109.5 |
H14A—C14—H14B | 107.7 | S21—C25—H25B | 109.5 |
C15—S11—C14 | 100.21 (6) | H25A—C25—H25B | 109.5 |
S11—C15—H15A | 109.5 | S21—C25—H25C | 109.5 |
S11—C15—H15B | 109.5 | H25A—C25—H25C | 109.5 |
H15A—C15—H15B | 109.5 | H25B—C25—H25C | 109.5 |
S11—C15—H15C | 109.5 | H1W—OW—H2W | 104 (2) |
O1A—C11—C12—N11 | 3.82 (12) | O2A—C21—C22—N21 | −21.62 (15) |
O1B—C11—C12—N11 | −176.01 (9) | O2B—C21—C22—N21 | 160.75 (10) |
O1B—C11—C12—C13 | −53.83 (12) | O2A—C21—C22—C23 | 100.30 (13) |
O1A—C11—C12—C13 | 126.01 (10) | O2B—C21—C22—C23 | −77.33 (12) |
N11—C12—C13—C14 | −153.83 (9) | N21—C22—C23—C24 | −84.52 (11) |
C11—C12—C13—C14 | 85.17 (11) | C21—C22—C23—C24 | 155.34 (9) |
C12—C13—C14—S11 | 65.58 (11) | C22—C23—C24—S21 | 171.84 (7) |
C13—C14—S11—C15 | 67.02 (9) | C23—C24—S21—C25 | 58.75 (10) |
D—H···A | D—H | H···A | D···A | D—H···A |
N11—H11A···OWi | 0.89 | 2.00 | 2.818 (1) | 153 |
N11—H11B···O3 | 0.89 | 2.18 | 3.042 (1) | 164 |
N11—H11C···O4ii | 0.89 | 2.08 | 2.962 (1) | 171 |
O2B—H2B···O1Biii | 0.82 | 1.71 | 2.500 (1) | 163 |
N21—H21A···O2 | 0.89 | 2.20 | 2.909 (1) | 137 |
N21—H21A···O2Aii | 0.89 | 2.57 | 3.189 (2) | 127 |
N21—H21B···O3i | 0.89 | 2.21 | 3.044 (1) | 155 |
N21—H21C···OWiv | 0.89 | 2.01 | 2.798 (1) | 147 |
OW—H1W···O1A | 0.80 (2) | 1.92 (3) | 2.706 (1) | 169 (2) |
OW—H2W···O1Av | 0.82 (2) | 1.95 (2) | 2.759 (1) | 168 (2) |
Symmetry codes: (i) x, y−1, z; (ii) x, y+1, z; (iii) x+1, y−2, z; (iv) −x+1, y−3/2, −z+1; (v) −x, y+1/2, −z+1. |