Supporting information
Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536804010645/wn6246sup1.cif | |
Structure factor file (CIF format) https://doi.org/10.1107/S1600536804010645/wn6246Isup2.hkl |
CCDC reference: 242320
Key indicators
- Single-crystal X-ray study
- T = 293 K
- Mean (C-C) = 0.004 Å
- R factor = 0.056
- wR factor = 0.099
- Data-to-parameter ratio = 17.7
checkCIF/PLATON results
No syntax errors found
Alert level B PLAT242_ALERT_2_B Check Low U(eq) as Compared to Neighbors .... S1
Alert level C PLAT042_ALERT_1_C Calc. and Rep. MoietyFormula Strings Differ .... ? PLAT125_ALERT_4_C No _symmetry_space_group_name_Hall Given ....... ?
0 ALERT level A = In general: serious problem 1 ALERT level B = Potentially serious problem 2 ALERT level C = Check and explain 0 ALERT level G = General alerts; check 1 ALERT type 1 CIF construction/syntax error, inconsistent or missing data 1 ALERT type 2 Indicator that the structure model may be wrong or deficient 0 ALERT type 3 Indicator that the structure quality may be low 1 ALERT type 4 Improvement, methodology, query or suggestion
Data collection: CrysAlis CCD (Kuma, 2000); cell refinement: CrysAlis RED (Kuma, 2000); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: DIAMOND (Brandenburg, 2001); software used to prepare material for publication: SHELXL97.
2C6H16N+·SO42− | F(000) = 664 |
Mr = 300.46 | Dx = 1.169 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
a = 8.7869 (8) Å | Cell parameters from 1569 reflections |
b = 8.8329 (8) Å | θ = 5.1–18.9° |
c = 22.095 (2) Å | µ = 0.20 mm−1 |
β = 95.21 (1)° | T = 293 K |
V = 1707.8 (3) Å3 | Isometric, colourless |
Z = 4 | 0.30 × 0.20 × 0.15 mm |
Stoe CCD diffractometer | 2834 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.043 |
Graphite monochromator | θmax = 27.0°, θmin = 4.2° |
ω scans | h = −10→11 |
17529 measured reflections | k = −11→11 |
3699 independent reflections | l = −25→28 |
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)] = 0.056 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.099 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.01 | w = 1/[σ2(Fo2) + (0.01P)2 + 1.7P] where P = (Fo2 + 2Fc2)/3 |
3699 reflections | (Δ/σ)max = 0.005 |
209 parameters | Δρmax = 0.50 e Å−3 |
4 restraints | Δρmin = −0.27 e Å−3 |
Experimental. A single-crystal cut from the raw material of the title compound was mounted on a Stoe four-circle diffractometer equipped with a CCD-detector. For the data collection 13 ω scans (1.0°) with different χ, φ and 2θ settings and a detector-to-crystal distance of 80 mm were performed. Integration procedures using variable and intensity-dependent integration masks and integration width of 1.00° yielded a data completeness of more than 99.0% for the refined data. the IR spectrum was recorded on a DigiLab, formerly known as Bio-Rad, FTS-3500 F T—IR spectrometer with a resolution of 4 cm-1. A single-crystal was fixed on the ZnSe plate of the single reflection ATR (attenuated total reflectance)-accessory unit (MIRacle, PIKE-Technologies, Madison). The Raman spectrum was recorded on the FT-Raman Accessory (DigiLab (BioRad), Krefeld, Germany), which is attached to the IR-Spectrometer FTS-3500. The FT–Raman contains a YAG-laser and a germanium detector. The resolution was 4 cm-1 and the power 379 mW. |
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 | 0.27840 (6) | 0.47867 (6) | 0.37369 (2) | 0.03142 (14) | |
N1 | 0.3003 (2) | 0.4585 (2) | 0.54755 (9) | 0.0383 (5) | |
H11 | 0.293 (2) | 0.480 (3) | 0.5087 (8) | 0.040 (6)* | |
H12 | 0.390 (2) | 0.487 (3) | 0.5640 (10) | 0.050 (7)* | |
N2 | 0.2864 (2) | 0.0732 (2) | 0.29931 (9) | 0.0348 (4) | |
H21 | 0.268 (3) | 0.163 (2) | 0.3124 (10) | 0.046 (7)* | |
H22 | 0.275 (2) | 0.075 (3) | 0.2600 (8) | 0.038 (7)* | |
C7 | 0.4529 (3) | 0.0403 (3) | 0.31541 (10) | 0.0403 (5) | |
H7 | 0.4741 | 0.0451 | 0.3597 | 0.046 (7)* | |
C8 | 0.4931 (3) | −0.1166 (3) | 0.29420 (12) | 0.0524 (7) | |
H8A | 0.4408 | −0.1910 | 0.3163 | 0.064 (5)* | |
H8B | 0.6014 | −0.1318 | 0.3013 | 0.064 (5)* | |
H8C | 0.4625 | −0.1263 | 0.2515 | 0.064 (5)* | |
C9 | 0.5430 (3) | 0.1631 (3) | 0.28723 (12) | 0.0544 (7) | |
H9A | 0.5146 | 0.2599 | 0.3024 | 0.063 (5)* | |
H9B | 0.5214 | 0.1609 | 0.2439 | 0.063 (5)* | |
H9C | 0.6502 | 0.1466 | 0.2975 | 0.063 (5)* | |
C10 | 0.1722 (3) | −0.0358 (3) | 0.32045 (11) | 0.0430 (6) | |
H10 | 0.1889 | −0.1350 | 0.3023 | 0.042 (6)* | |
C11 | 0.0148 (3) | 0.0201 (3) | 0.29717 (14) | 0.0612 (7) | |
H11A | 0.0088 | 0.0296 | 0.2537 | 0.073 (5)* | |
H11B | −0.0034 | 0.1170 | 0.3149 | 0.073 (5)* | |
H11C | −0.0608 | −0.0508 | 0.3082 | 0.073 (5)* | |
C12 | 0.1912 (4) | −0.0516 (4) | 0.38889 (13) | 0.0689 (9) | |
H12A | 0.2924 | −0.0874 | 0.4014 | 0.095 (6)* | |
H12B | 0.1175 | −0.1226 | 0.4015 | 0.095 (6)* | |
H12C | 0.1758 | 0.0450 | 0.4073 | 0.095 (6)* | |
O1 | 0.2203 (2) | 0.5361 (2) | 0.42925 (7) | 0.0547 (5) | |
O2 | 0.4428 (2) | 0.4589 (3) | 0.38257 (11) | 0.0931 (8) | |
O3 | 0.2073 (2) | 0.33291 (19) | 0.35722 (9) | 0.0610 (5) | |
O4 | 0.2400 (3) | 0.5865 (2) | 0.32480 (8) | 0.0687 (6) | |
C1 | 0.2901 (3) | 0.2905 (3) | 0.55347 (12) | 0.0497 (6) | |
H1 | 0.3006 | 0.2639 | 0.5967 | 0.056 (7)* | |
C2 | 0.4222 (3) | 0.2221 (3) | 0.52352 (14) | 0.0668 (8) | |
H2A | 0.4224 | 0.1143 | 0.5290 | 0.086 (6)* | |
H2B | 0.5166 | 0.2635 | 0.5417 | 0.086 (6)* | |
H2C | 0.4115 | 0.2452 | 0.4809 | 0.086 (6)* | |
C3 | 0.1367 (3) | 0.2344 (3) | 0.52538 (14) | 0.0668 (8) | |
H3A | 0.1236 | 0.2631 | 0.4833 | 0.080 (6)* | |
H3B | 0.0566 | 0.2783 | 0.5464 | 0.080 (6)* | |
H3C | 0.1326 | 0.1261 | 0.5286 | 0.080 (6)* | |
C4 | 0.1828 (3) | 0.5537 (3) | 0.57548 (11) | 0.0481 (6) | |
H4 | 0.0824 | 0.5318 | 0.5543 | 0.048 (7)* | |
C5 | 0.1777 (3) | 0.5162 (4) | 0.64198 (12) | 0.0724 (9) | |
H5A | 0.1458 | 0.4130 | 0.6460 | 0.078 (5)* | |
H5B | 0.1067 | 0.5823 | 0.6594 | 0.078 (5)* | |
H5C | 0.2776 | 0.5294 | 0.6628 | 0.078 (5)* | |
C6 | 0.2206 (3) | 0.7182 (3) | 0.56484 (13) | 0.0626 (8) | |
H6A | 0.3197 | 0.7410 | 0.5847 | 0.076 (5)* | |
H6B | 0.1454 | 0.7815 | 0.5811 | 0.076 (5)* | |
H6C | 0.2208 | 0.7363 | 0.5220 | 0.076 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
S1 | 0.0341 (3) | 0.0355 (3) | 0.0242 (3) | 0.0000 (2) | 0.00066 (19) | −0.0025 (2) |
N1 | 0.0316 (11) | 0.0575 (13) | 0.0255 (10) | −0.0010 (9) | 0.0013 (8) | 0.0024 (9) |
N2 | 0.0473 (12) | 0.0300 (10) | 0.0273 (10) | 0.0011 (8) | 0.0043 (8) | −0.0018 (8) |
C7 | 0.0438 (13) | 0.0470 (14) | 0.0294 (12) | 0.0008 (11) | −0.0008 (9) | −0.0035 (10) |
C8 | 0.0530 (16) | 0.0479 (15) | 0.0562 (17) | 0.0094 (12) | 0.0049 (13) | 0.0055 (12) |
C9 | 0.0507 (16) | 0.0520 (16) | 0.0616 (18) | −0.0082 (13) | 0.0105 (13) | −0.0087 (13) |
C10 | 0.0504 (14) | 0.0306 (12) | 0.0496 (14) | −0.0029 (11) | 0.0123 (11) | −0.0012 (10) |
C11 | 0.0476 (15) | 0.0529 (16) | 0.084 (2) | −0.0049 (13) | 0.0112 (14) | −0.0077 (15) |
C12 | 0.082 (2) | 0.074 (2) | 0.0547 (18) | −0.0056 (17) | 0.0244 (15) | 0.0212 (15) |
O1 | 0.0771 (12) | 0.0591 (11) | 0.0298 (9) | 0.0110 (10) | 0.0149 (8) | −0.0044 (8) |
O2 | 0.0359 (10) | 0.142 (2) | 0.0975 (17) | 0.0112 (12) | −0.0131 (10) | −0.0489 (16) |
O3 | 0.0699 (12) | 0.0354 (10) | 0.0797 (14) | −0.0099 (9) | 0.0180 (10) | −0.0172 (9) |
O4 | 0.1241 (18) | 0.0517 (11) | 0.0302 (10) | 0.0027 (11) | 0.0069 (10) | 0.0088 (8) |
C1 | 0.0553 (16) | 0.0545 (16) | 0.0389 (14) | 0.0001 (13) | 0.0029 (12) | 0.0128 (12) |
C2 | 0.0620 (18) | 0.0598 (19) | 0.078 (2) | 0.0154 (15) | 0.0011 (16) | −0.0009 (15) |
C3 | 0.0604 (18) | 0.0608 (19) | 0.080 (2) | −0.0154 (15) | 0.0105 (16) | 0.0048 (16) |
C4 | 0.0297 (12) | 0.0767 (19) | 0.0380 (13) | 0.0048 (12) | 0.0037 (10) | −0.0087 (12) |
C5 | 0.0650 (18) | 0.111 (3) | 0.0446 (16) | −0.0012 (19) | 0.0239 (13) | −0.0085 (17) |
C6 | 0.0594 (18) | 0.066 (2) | 0.0620 (19) | 0.0100 (15) | 0.0013 (14) | −0.0163 (15) |
S1—O2 | 1.450 (2) | C11—H11A | 0.9600 |
S1—O4 | 1.456 (2) | C11—H11B | 0.9600 |
S1—O1 | 1.462 (2) | C11—H11C | 0.9600 |
S1—O3 | 1.463 (2) | C12—H12A | 0.9600 |
N1—C1 | 1.493 (3) | C12—H12B | 0.9600 |
N1—C4 | 1.506 (3) | C12—H12C | 0.9600 |
N1—H11 | 0.874 (17) | C1—C3 | 1.515 (4) |
N1—H12 | 0.870 (18) | C1—C2 | 1.514 (4) |
N2—C10 | 1.496 (3) | C1—H1 | 0.9800 |
N2—C7 | 1.502 (3) | C2—H2A | 0.9600 |
N2—H21 | 0.868 (18) | C2—H2B | 0.9600 |
N2—H22 | 0.865 (17) | C2—H2C | 0.9600 |
C7—C8 | 1.514 (3) | C3—H3A | 0.9600 |
C7—C9 | 1.511 (3) | C3—H3B | 0.9600 |
C7—H7 | 0.9800 | C3—H3C | 0.9600 |
C8—H8A | 0.9600 | C4—C6 | 1.513 (4) |
C8—H8B | 0.9600 | C4—C5 | 1.511 (3) |
C8—H8C | 0.9600 | C4—H4 | 0.9800 |
C9—H9A | 0.9600 | C5—H5A | 0.9600 |
C9—H9B | 0.9600 | C5—H5B | 0.9600 |
C9—H9C | 0.9600 | C5—H5C | 0.9600 |
C10—C11 | 1.514 (3) | C6—H6A | 0.9600 |
C10—C12 | 1.513 (3) | C6—H6B | 0.9600 |
C10—H10 | 0.9800 | C6—H6C | 0.9600 |
O2—S1—O4 | 109.88 (15) | C10—C11—H11C | 109.5 |
O2—S1—O1 | 110.34 (12) | H11A—C11—H11C | 109.5 |
O4—S1—O1 | 108.70 (11) | H11B—C11—H11C | 109.5 |
O2—S1—O3 | 108.99 (13) | C10—C12—H12A | 109.5 |
O4—S1—O3 | 109.02 (12) | C10—C12—H12B | 109.5 |
O1—S1—O3 | 109.88 (11) | H12A—C12—H12B | 109.5 |
C1—N1—C4 | 118.01 (19) | C10—C12—H12C | 109.5 |
C1—N1—H11 | 107.4 (15) | H12A—C12—H12C | 109.5 |
C4—N1—H11 | 106.9 (15) | H12B—C12—H12C | 109.5 |
C1—N1—H12 | 107.8 (17) | N1—C1—C3 | 110.3 (2) |
C4—N1—H12 | 107.2 (16) | N1—C1—C2 | 107.7 (2) |
H11—N1—H12 | 109 (2) | C3—C1—C2 | 112.3 (2) |
C10—N2—C7 | 117.87 (18) | N1—C1—H1 | 108.8 |
C10—N2—H21 | 109.5 (16) | C3—C1—H1 | 108.8 |
C7—N2—H21 | 108.0 (16) | C2—C1—H1 | 108.8 |
C10—N2—H22 | 107.8 (15) | C1—C2—H2A | 109.5 |
C7—N2—H22 | 105.4 (15) | C1—C2—H2B | 109.5 |
H21—N2—H22 | 108 (2) | H2A—C2—H2B | 109.5 |
N2—C7—C8 | 110.71 (19) | C1—C2—H2C | 109.5 |
N2—C7—C9 | 107.37 (19) | H2A—C2—H2C | 109.5 |
C8—C7—C9 | 112.6 (2) | H2B—C2—H2C | 109.5 |
N2—C7—H7 | 108.7 | C1—C3—H3A | 109.5 |
C8—C7—H7 | 108.7 | C1—C3—H3B | 109.5 |
C9—C7—H7 | 108.7 | H3A—C3—H3B | 109.5 |
C7—C8—H8A | 109.5 | C1—C3—H3C | 109.5 |
C7—C8—H8B | 109.5 | H3A—C3—H3C | 109.5 |
H8A—C8—H8B | 109.5 | H3B—C3—H3C | 109.5 |
C7—C8—H8C | 109.5 | C6—C4—C5 | 112.8 (2) |
H8A—C8—H8C | 109.5 | C6—C4—N1 | 107.7 (2) |
H8B—C8—H8C | 109.5 | C5—C4—N1 | 111.0 (2) |
C7—C9—H9A | 109.5 | C6—C4—H4 | 108.4 |
C7—C9—H9B | 109.5 | C5—C4—H4 | 108.4 |
H9A—C9—H9B | 109.5 | N1—C4—H4 | 108.4 |
C7—C9—H9C | 109.5 | C4—C5—H5A | 109.5 |
H9A—C9—H9C | 109.5 | C4—C5—H5B | 109.5 |
H9B—C9—H9C | 109.5 | H5A—C5—H5B | 109.5 |
N2—C10—C11 | 107.6 (2) | C4—C5—H5C | 109.5 |
N2—C10—C12 | 110.8 (2) | H5A—C5—H5C | 109.5 |
C11—C10—C12 | 112.6 (2) | H5B—C5—H5C | 109.5 |
N2—C10—H10 | 108.6 | C4—C6—H6A | 109.5 |
C11—C10—H10 | 108.6 | C4—C6—H6B | 109.5 |
C12—C10—H10 | 108.6 | H6A—C6—H6B | 109.5 |
C10—C11—H11A | 109.5 | C4—C6—H6C | 109.5 |
C10—C11—H11B | 109.5 | H6A—C6—H6C | 109.5 |
H11A—C11—H11B | 109.5 | H6B—C6—H6C | 109.5 |
C10—N2—C7—C8 | 54.9 (3) | C4—N1—C1—C3 | 58.7 (3) |
C10—N2—C7—C9 | 178.1 (2) | C4—N1—C1—C2 | −178.4 (2) |
C7—N2—C10—C11 | −178.5 (2) | C1—N1—C4—C6 | 178.4 (2) |
C7—N2—C10—C12 | 58.0 (3) | C1—N1—C4—C5 | 54.5 (3) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···O1 | 0.87 (2) | 1.88 (2) | 2.732 (2) | 164 (2) |
N1—H12···O2i | 0.87 (2) | 1.87 (2) | 2.716 (3) | 165 (2) |
N2—H21···O3 | 0.87 (2) | 1.90 (2) | 2.746 (3) | 166 (2) |
N2—H22···O4ii | 0.87 (2) | 1.87 (2) | 2.733 (3) | 177 (2) |
Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1/2, y−1/2, −z+1/2. |