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A series of diaminium thiosulfates, derivatives of diamines: NH2CH2CH(CH3)NH2 (1) and NH2(CH2)nNH2, n = 3–6 [(2)–(5)] and thiosulfuric acid were prepared and their structures determined by single-crystal X-ray diffraction analysis. Compounds (1), (2) and (4) turned out to be hydrates. The crystal structure of 1,2-propylenediaminium thiosulfate is chiral and exhibits spontaneous resolution. Crystals for both enantiomers [(1a) and (1b)] were obtained with high enantiometric excess and examined. An extended network of strong, charge-assisted hydrogen bonding of the +N—H
O− type (also O—HO and O—HS for hydrates) is most likely the main factor defining crystal packing and the variable conformation of the cations. The formation of chiral hydrogen-bond motifs – distorted cubans – seems to induce the formation of chiral solid-state structure from achiral components in the case of (4). Diaminium thiosulfates with an odd number of C atoms in the alkyl chain [compounds (1), (2) and (4)] form three-dimensional supramolecular networks, while in the case of diaminium salts with an even number of C atoms [(3) and (5)], two-dimensional layers of hydrogen-bond domains are observed. The aminium thiosulfates were also characterized by elemental analysis, NMR and Fourier transform (FT)–IR spectroscopy. The conformations of α,ω-alkyldiaminium cations in the solid state are discussed and rationalized by DFT calculations.
O− type (also O—HO and O—HS for hydrates) is most likely the main factor defining crystal packing and the variable conformation of the cations. The formation of chiral hydrogen-bond motifs – distorted cubans – seems to induce the formation of chiral solid-state structure from achiral components in the case of (4). Diaminium thiosulfates with an odd number of C atoms in the alkyl chain [compounds (1), (2) and (4)] form three-dimensional supramolecular networks, while in the case of diaminium salts with an even number of C atoms [(3) and (5)], two-dimensional layers of hydrogen-bond domains are observed. The aminium thiosulfates were also characterized by elemental analysis, NMR and Fourier transform (FT)–IR spectroscopy. The conformations of α,ω-alkyldiaminium cations in the solid state are discussed and rationalized by DFT calculations.Keywords: charge-assisted hydrogen bonding; single-crystal diffraction analysis; alkyldiaminium cation; thiosulfate.
Supporting information
 | Crystallographic Information File (CIF) https://doi.org/10.1107/S2052520617004802/eb5057sup1.cif |
 | Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_1asup2.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_1bsup3.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_2sup4.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_3sup5.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_4sup6.hkl |
| Structure factor file (CIF format) https://doi.org/10.1107/S2052520617004802/eb5057Comp_5sup7.hkl |
CCDC references: 1484873; 1484874; 1484875; 1484876; 1484877; 1484878
Computing details top
Data collection: CrysAlis PRO, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) for Comp_1a; CrysAlis PRO (Agilent Technologies, 2011), Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) for Comp_1b; CrysAlis PRO (Agilent Technologies, 2011) for Comp_3; STOE X-AREA for Comp_4, Comp_5. Cell refinement: CrysAlis PRO, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) for Comp_1a; CrysAlis PRO (Agilent Technologies, 2011), Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) for Comp_1b; CrysAlis PRO (Agilent Technologies, 2011) for Comp_3; STOE X-AREA for Comp_4, Comp_5. Data reduction: CrysAlis PRO, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) for Comp_1a; CrysAlis PRO (Agilent Technologies, 2011), Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) for Comp_1b; CrysAlis PRO (Agilent Technologies, 2011) for Comp_3; STOE X-RED for Comp_4, Comp_5. Program(s) used to solve structure: SHELXS2013 (Sheldrick, 2013) for Comp_1a, Comp_3; SHELXS2014 (Sheldrick, 2014) for Comp_1b. For all compounds, program(s) used to refine structure: SHELXL2014 (Sheldrick, 2014); molecular graphics: ORTEP for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX publication routines (Farrugia, 2012).
(Comp_1a) top
Crystal data top
| O3S22−·C3H12N22+·H2O | F(000) = 440 |
| Mr = 206.28 | Dx = 1.507 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 2143 reflections |
| a = 8.4086 (5) Å | θ = 2.8–28.6° |
| b = 9.7870 (5) Å | µ = 0.56 mm−1 |
| c = 11.0477 (6) Å | T = 293 K |
| V = 909.17 (9) Å3 | Fragment, colourless |
| Z = 4 | 0.52 × 0.34 × 0.12 mm |
Data collection top
| KUMA KM4CCD, Sapphire2, large Be window diffractometer | 1497 reflections with I > 2σ(I) |
| Graphite monochromator | Rint = 0.032 |
| ω scans | θmax = 25.1°, θmin = 2.8° |
| Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −10→7 |
| Tmin = 0.890, Tmax = 1 | k = −11→10 |
| 3135 measured reflections | l = −8→13 |
| 1620 independent reflections |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.038 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.093 | w = 1/[σ2(Fo2) + (0.0504P)2] where P = (Fo2 + 2Fc2)/3 |
| S = 1.06 | (Δ/σ)max < 0.001 |
| 1620 reflections | Δρmax = 0.40 e Å−3 |
| 108 parameters | Δρmin = −0.22 e Å−3 |
| 2 restraints | Absolute structure: Flack x determined using 577 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.09 (9) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.4586 (4) | 0.8918 (4) | 0.4035 (3) | 0.0272 (9) | |
| H1A | 0.3656 | 0.9338 | 0.4135 | 0.041* | |
| H1B | 0.4475 | 0.8032 | 0.4197 | 0.041* | |
| H1C | 0.491 | 0.9022 | 0.3274 | 0.041* | |
| N2 | 0.6737 (4) | 1.1714 (3) | 0.5697 (3) | 0.0299 (9) | |
| H2A | 0.6108 | 1.1546 | 0.6327 | 0.045* | |
| H2B | 0.6795 | 1.2611 | 0.5575 | 0.045* | |
| H2C | 0.7705 | 1.1386 | 0.5844 | 0.045* | |
| C1 | 0.5793 (6) | 0.9527 (5) | 0.4878 (4) | 0.0297 (10) | |
| H1D | 0.6788 | 0.9034 | 0.4804 | 0.036* | |
| H1E | 0.5424 | 0.9439 | 0.5706 | 0.036* | |
| C2 | 0.6064 (6) | 1.1033 (4) | 0.4585 (4) | 0.0279 (10) | |
| H2 | 0.5034 | 1.1453 | 0.4399 | 0.033* | |
| C3 | 0.7182 (6) | 1.1271 (5) | 0.3513 (4) | 0.0395 (12) | |
| H3A | 0.6755 | 1.0838 | 0.2805 | 0.059* | |
| H3B | 0.7287 | 1.2234 | 0.337 | 0.059* | |
| H3C | 0.8208 | 1.089 | 0.3693 | 0.059* | |
| O4 | 0.4637 (5) | 1.1248 (4) | 0.7586 (3) | 0.0470 (10) | |
| H4A | 0.416 (6) | 1.051 (4) | 0.756 (5) | 0.056* | |
| H4B | 0.504 (7) | 1.139 (6) | 0.823 (3) | 0.056* | |
| S1 | 0.58065 (14) | 0.52359 (11) | 0.42411 (8) | 0.0227 (3) | |
| S2 | 0.71520 (15) | 0.62866 (13) | 0.30848 (10) | 0.0345 (3) | |
| O1 | 0.4704 (4) | 0.6186 (3) | 0.4861 (3) | 0.0320 (8) | |
| O2 | 0.4877 (4) | 0.4177 (3) | 0.3584 (3) | 0.0315 (8) | |
| O3 | 0.6842 (4) | 0.4564 (3) | 0.5152 (3) | 0.0313 (8) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.026 (2) | 0.025 (2) | 0.0307 (19) | 0.0008 (16) | 0.0015 (15) | −0.0006 (15) |
| N2 | 0.030 (2) | 0.028 (2) | 0.0324 (19) | −0.0012 (17) | 0.0004 (16) | −0.0009 (17) |
| C1 | 0.028 (2) | 0.032 (3) | 0.029 (2) | 0.003 (2) | −0.0028 (19) | 0.0031 (19) |
| C2 | 0.028 (3) | 0.028 (3) | 0.028 (2) | 0.002 (2) | −0.0042 (18) | −0.0014 (18) |
| C3 | 0.038 (3) | 0.044 (3) | 0.037 (2) | −0.003 (3) | 0.002 (2) | 0.006 (2) |
| O4 | 0.052 (3) | 0.058 (2) | 0.0309 (18) | −0.013 (2) | −0.0007 (17) | 0.0057 (19) |
| S1 | 0.0241 (5) | 0.0237 (5) | 0.0204 (5) | −0.0005 (5) | −0.0008 (4) | 0.0005 (4) |
| S2 | 0.0345 (7) | 0.0368 (7) | 0.0322 (6) | −0.0021 (6) | 0.0086 (5) | 0.0060 (5) |
| O1 | 0.0352 (19) | 0.0282 (17) | 0.0325 (16) | 0.0063 (15) | 0.0087 (13) | 0.0004 (14) |
| O2 | 0.0310 (18) | 0.0339 (18) | 0.0296 (15) | −0.0085 (15) | −0.0013 (14) | −0.0054 (13) |
| O3 | 0.0355 (19) | 0.0273 (17) | 0.0311 (15) | 0.0003 (15) | −0.0073 (13) | 0.0051 (13) |
Geometric parameters (Å, º) top
| N1—C1 | 1.501 (5) | C2—C3 | 1.530 (6) |
| N1—H1A | 0.89 | C2—H2 | 0.98 |
| N1—H1B | 0.89 | C3—H3A | 0.96 |
| N1—H1C | 0.89 | C3—H3B | 0.96 |
| N2—C2 | 1.508 (5) | C3—H3C | 0.96 |
| N2—H2A | 0.89 | O4—H4A | 0.83 (3) |
| N2—H2B | 0.89 | O4—H4B | 0.80 (2) |
| N2—H2C | 0.89 | S1—O1 | 1.481 (3) |
| C1—C2 | 1.526 (6) | S1—O3 | 1.484 (3) |
| C1—H1D | 0.97 | S1—O2 | 1.487 (3) |
| C1—H1E | 0.97 | S1—S2 | 1.9924 (15) |
| C1—N1—H1A | 109.5 | N2—C2—C3 | 109.4 (4) |
| C1—N1—H1B | 109.5 | C1—C2—C3 | 113.7 (4) |
| H1A—N1—H1B | 109.5 | N2—C2—H2 | 108.5 |
| C1—N1—H1C | 109.5 | C1—C2—H2 | 108.5 |
| H1A—N1—H1C | 109.5 | C3—C2—H2 | 108.5 |
| H1B—N1—H1C | 109.5 | C2—C3—H3A | 109.5 |
| C2—N2—H2A | 109.5 | C2—C3—H3B | 109.5 |
| C2—N2—H2B | 109.5 | H3A—C3—H3B | 109.5 |
| H2A—N2—H2B | 109.5 | C2—C3—H3C | 109.5 |
| C2—N2—H2C | 109.5 | H3A—C3—H3C | 109.5 |
| H2A—N2—H2C | 109.5 | H3B—C3—H3C | 109.5 |
| H2B—N2—H2C | 109.5 | H4A—O4—H4B | 112 (6) |
| N1—C1—C2 | 110.7 (3) | O1—S1—O3 | 109.40 (18) |
| N1—C1—H1D | 109.5 | O1—S1—O2 | 109.51 (19) |
| C2—C1—H1D | 109.5 | O3—S1—O2 | 109.32 (19) |
| N1—C1—H1E | 109.5 | O1—S1—S2 | 109.14 (13) |
| C2—C1—H1E | 109.5 | O3—S1—S2 | 109.29 (14) |
| H1D—C1—H1E | 108.1 | O2—S1—S2 | 110.17 (13) |
| N2—C2—C1 | 108.1 (3) | ||
| N1—C1—C2—N2 | 158.1 (4) | N1—C1—C2—C3 | −80.2 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O3i | 0.89 | 2.03 | 2.888 (5) | 163 |
| N1—H1B···O1 | 0.89 | 1.96 | 2.827 (5) | 164 |
| N1—H1C···O2ii | 0.89 | 2.07 | 2.939 (4) | 167 |
| N2—H2A···O4 | 0.89 | 1.88 | 2.772 (5) | 175 |
| N2—H2B···O3iii | 0.89 | 1.97 | 2.855 (5) | 175 |
| N2—H2C···O2iv | 0.89 | 2.01 | 2.892 (5) | 171 |
| C1—H1D···O1iv | 0.97 | 2.49 | 3.374 (6) | 152 |
| O4—H4A···S2i | 0.83 (3) | 2.54 (3) | 3.327 (4) | 159 (5) |
| O4—H4B···O1v | 0.80 (2) | 2.13 (3) | 2.875 (5) | 155 (6) |
| Symmetry codes: (i) x−1/2, −y+3/2, −z+1; (ii) −x+1, y+1/2, −z+1/2; (iii) x, y+1, z; (iv) x+1/2, −y+3/2, −z+1; (v) −x+1, y+1/2, −z+3/2. |
(Comp_1b) top
Crystal data top
| O3S22−·C3H12N22+·H2O | F(000) = 440 |
| Mr = 206.28 | Dx = 1.526 Mg m−3 |
| Orthorhombic, P212121 | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: P 2ac 2ab | Cell parameters from 1306 reflections |
| a = 8.3714 (6) Å | θ = 2.8–28.7° |
| b = 9.7607 (10) Å | µ = 0.57 mm−1 |
| c = 10.9874 (12) Å | T = 120 K |
| V = 897.79 (15) Å3 | Block, colourless |
| Z = 4 | 0.41 × 0.35 × 0.2 mm |
Data collection top
| KUMA KM4CCD, Sapphire2, large Be window diffractometer | 1506 independent reflections |
| Graphite monochromator | 1361 reflections with I > 2σ(I) |
| Detector resolution: 8.19 pixels mm-1 | Rint = 0.027 |
| ω scans | θmax = 25.1°, θmin = 2.8° |
| Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −9→3 |
| Tmin = 0.752, Tmax = 1 | k = −10→11 |
| 2086 measured reflections | l = −13→6 |
Refinement top
| Refinement on F2 | Secondary atom site location: difference Fourier map |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.044 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.108 | w = 1/[σ2(Fo2) + (0.0491P)2 + 0.7203P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.04 | (Δ/σ)max < 0.001 |
| 1506 reflections | Δρmax = 0.51 e Å−3 |
| 109 parameters | Δρmin = −0.35 e Å−3 |
| 0 restraints | Absolute structure: Refined as an inversion twin. |
| Primary atom site location: structure-invariant direct methods | Absolute structure parameter: −0.2 (2) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| N1 | 0.5434 (5) | 0.1096 (4) | 0.5972 (4) | 0.0124 (10) | |
| H1A | 0.6377 | 0.064 | 0.5897 | 0.019* | |
| H1B | 0.5078 | 0.1026 | 0.6752 | 0.019* | |
| H1C | 0.5581 | 0.1995 | 0.5782 | 0.019* | |
| N2 | 0.3265 (5) | −0.1711 (4) | 0.4289 (4) | 0.0150 (10) | |
| H2A | 0.3903 | −0.1529 | 0.3638 | 0.023* | |
| H2B | 0.2266 | −0.138 | 0.4145 | 0.023* | |
| H2C | 0.3215 | −0.2632 | 0.4408 | 0.023* | |
| C1 | 0.4223 (7) | 0.0480 (6) | 0.5123 (5) | 0.0166 (12) | |
| H1D | 0.4603 | 0.0573 | 0.4273 | 0.02* | |
| H1E | 0.3202 | 0.0984 | 0.5197 | 0.02* | |
| C2 | 0.3949 (7) | −0.1030 (6) | 0.5413 (5) | 0.0159 (13) | |
| H2 | 0.5002 | −0.1463 | 0.5604 | 0.019* | |
| C3 | 0.2819 (7) | −0.1261 (6) | 0.6492 (5) | 0.0196 (13) | |
| H3A | 0.3262 | −0.0821 | 0.722 | 0.029* | |
| H3B | 0.1772 | −0.0864 | 0.6308 | 0.029* | |
| H3C | 0.2702 | −0.2246 | 0.6639 | 0.029* | |
| O4 | 0.5386 (5) | −0.1246 (5) | 0.2407 (4) | 0.0221 (10) | |
| H4A | 0.590 (8) | −0.050 (7) | 0.246 (6) | 0.026* | |
| H4B | 0.509 (8) | −0.143 (7) | 0.180 (6) | 0.026* | |
| S1 | 0.41899 (17) | 0.47686 (14) | 0.57586 (12) | 0.0135 (3) | |
| S2 | 0.28471 (17) | 0.36996 (15) | 0.69154 (13) | 0.0171 (4) | |
| O1 | 0.5316 (4) | 0.3821 (4) | 0.5128 (3) | 0.0145 (9) | |
| O2 | 0.5124 (4) | 0.5842 (4) | 0.6421 (3) | 0.0155 (9) | |
| O3 | 0.3140 (4) | 0.5444 (4) | 0.4837 (3) | 0.0165 (9) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.010 (2) | 0.010 (2) | 0.017 (2) | −0.0018 (19) | 0.001 (2) | −0.0014 (18) |
| N2 | 0.011 (2) | 0.013 (2) | 0.021 (2) | −0.002 (2) | 0.002 (2) | 0.002 (2) |
| C1 | 0.011 (3) | 0.021 (3) | 0.017 (3) | 0.001 (3) | −0.001 (3) | 0.002 (2) |
| C2 | 0.012 (3) | 0.019 (3) | 0.016 (3) | 0.000 (2) | −0.003 (3) | 0.000 (2) |
| C3 | 0.013 (3) | 0.020 (3) | 0.025 (3) | −0.002 (3) | −0.004 (3) | 0.003 (3) |
| O4 | 0.023 (3) | 0.025 (2) | 0.018 (2) | −0.006 (2) | −0.003 (2) | −0.001 (2) |
| S1 | 0.0085 (6) | 0.0166 (7) | 0.0155 (7) | −0.0006 (6) | −0.0005 (6) | −0.0003 (6) |
| S2 | 0.0128 (7) | 0.0196 (7) | 0.0190 (7) | −0.0016 (7) | 0.0034 (7) | 0.0021 (6) |
| O1 | 0.0113 (19) | 0.0150 (19) | 0.0171 (19) | 0.0023 (17) | 0.0022 (17) | −0.0017 (17) |
| O2 | 0.0118 (19) | 0.017 (2) | 0.0179 (19) | −0.0036 (17) | 0.0020 (18) | −0.0029 (16) |
| O3 | 0.013 (2) | 0.016 (2) | 0.0205 (19) | −0.0017 (17) | −0.0023 (18) | −0.0002 (17) |
Geometric parameters (Å, º) top
| N1—C1 | 1.503 (7) | C2—C3 | 1.534 (8) |
| N1—H1A | 0.91 | C2—H2 | 1 |
| N1—H1B | 0.91 | C3—H3A | 0.98 |
| N1—H1C | 0.91 | C3—H3B | 0.98 |
| N2—C2 | 1.514 (7) | C3—H3C | 0.98 |
| N2—H2A | 0.91 | O4—H4A | 0.85 (7) |
| N2—H2B | 0.91 | O4—H4B | 0.74 (6) |
| N2—H2C | 0.91 | S1—O1 | 1.491 (4) |
| C1—C2 | 1.526 (8) | S1—O3 | 1.494 (4) |
| C1—H1D | 0.99 | S1—O2 | 1.496 (4) |
| C1—H1E | 0.99 | S1—S2 | 1.9920 (19) |
| C1—N1—H1A | 109.5 | N2—C2—C3 | 109.4 (4) |
| C1—N1—H1B | 109.5 | C1—C2—C3 | 113.3 (5) |
| H1A—N1—H1B | 109.5 | N2—C2—H2 | 108.6 |
| C1—N1—H1C | 109.5 | C1—C2—H2 | 108.6 |
| H1A—N1—H1C | 109.5 | C3—C2—H2 | 108.6 |
| H1B—N1—H1C | 109.5 | C2—C3—H3A | 109.5 |
| C2—N2—H2A | 109.5 | C2—C3—H3B | 109.5 |
| C2—N2—H2B | 109.5 | H3A—C3—H3B | 109.5 |
| H2A—N2—H2B | 109.5 | C2—C3—H3C | 109.5 |
| C2—N2—H2C | 109.5 | H3A—C3—H3C | 109.5 |
| H2A—N2—H2C | 109.5 | H3B—C3—H3C | 109.5 |
| H2B—N2—H2C | 109.5 | H4A—O4—H4B | 116 (7) |
| N1—C1—C2 | 111.0 (4) | O1—S1—O3 | 109.3 (2) |
| N1—C1—H1D | 109.4 | O1—S1—O2 | 109.3 (2) |
| C2—C1—H1D | 109.4 | O3—S1—O2 | 109.1 (2) |
| N1—C1—H1E | 109.4 | O1—S1—S2 | 109.17 (16) |
| C2—C1—H1E | 109.4 | O3—S1—S2 | 109.37 (16) |
| H1D—C1—H1E | 108 | O2—S1—S2 | 110.58 (17) |
| N2—C2—C1 | 108.1 (4) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O3i | 0.91 | 1.99 | 2.861 (6) | 160 |
| N1—H1B···O2ii | 0.91 | 2.02 | 2.913 (6) | 166 |
| N1—H1C···O1 | 0.91 | 1.93 | 2.819 (6) | 163 |
| N2—H2A···O4 | 0.91 | 1.86 | 2.763 (6) | 174 |
| N2—H2B···O2iii | 0.91 | 1.97 | 2.871 (6) | 170 |
| N2—H2C···O3iv | 0.91 | 1.94 | 2.843 (6) | 174 |
| C1—H1E···O1iii | 0.99 | 2.45 | 3.353 (7) | 152 |
| O4—H4A···S2i | 0.85 (7) | 2.49 (7) | 3.313 (5) | 163 (6) |
| O4—H4B···O1v | 0.74 (6) | 2.15 (6) | 2.848 (6) | 157 (7) |
| Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+1, y−1/2, −z+3/2; (iii) x−1/2, −y+1/2, −z+1; (iv) x, y−1, z; (v) −x+1, y−1/2, −z+1/2. |
(Comp_2) top
Crystal data top
| O3S22−·C3H12N22+·H2O | F(000) = 880 |
| Mr = 206.28 | Dx = 1.502 Mg m−3 |
| Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2yn | Cell parameters from 3409 reflections |
| a = 15.4097 (8) Å | θ = 2.5–28.6° |
| b = 8.0868 (4) Å | µ = 0.56 mm−1 |
| c = 15.4133 (13) Å | T = 120 K |
| β = 108.249 (6)° | Needle, colourless |
| V = 1824.1 (2) Å3 | 0.37 × 0.09 × 0.07 mm |
| Z = 8 |
Data collection top
| KUMA KM4CCD, Sapphire2, large Be window diffractometer | 3262 independent reflections |
| Graphite monochromator | 2918 reflections with I > 2σ(I) |
| Detector resolution: 8.19 pixels mm-1 | Rint = 0.025 |
| ω scans | θmax = 25.5°, θmin = 2.5° |
| Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | h = −11→18 |
| Tmin = 0.913, Tmax = 1 | k = −9→9 |
| 5760 measured reflections | l = −18→18 |
Refinement top
| Refinement on F2 | 0 constraints |
| Least-squares matrix: full | Hydrogen site location: mixed |
| R[F2 > 2σ(F2)] = 0.045 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.120 | w = 1/[σ2(Fo2) + (0.0661P)2 + 0.5404P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.05 | (Δ/σ)max < 0.001 |
| 3262 reflections | Δρmax = 0.63 e Å−3 |
| 219 parameters | Δρmin = −0.44 e Å−3 |
| 4 restraints |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component inversion twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| H7P | 0.255 (2) | 0.654 (5) | 0.176 (3) | 0.025 (12)* | |
| H7Q | 0.327 (4) | 0.710 (7) | 0.167 (3) | 0.07 (2)* | |
| H8P | 0.840 (2) | 0.693 (5) | 0.180 (3) | 0.028 (9)* | |
| H8Q | 0.819 (3) | 0.665 (5) | 0.247 (2) | 0.028 (9)* | |
| S1 | 0.01304 (6) | 0.73538 (11) | 0.12420 (6) | 0.0158 (2) | |
| S2 | 0.09108 (6) | 0.53199 (11) | 0.15945 (7) | 0.0217 (2) | |
| O1 | −0.08397 (17) | 0.6845 (3) | 0.08589 (18) | 0.0228 (6) | |
| O2 | 0.04020 (18) | 0.8281 (3) | 0.05278 (17) | 0.0236 (6) | |
| O3 | 0.02674 (18) | 0.8399 (3) | 0.20510 (17) | 0.0244 (6) | |
| S3 | 0.62242 (6) | 0.23787 (12) | 0.01295 (6) | 0.0163 (2) | |
| S4 | 0.66471 (7) | 0.04351 (11) | 0.09647 (7) | 0.0236 (3) | |
| O4 | 0.5963 (2) | 0.1828 (3) | −0.08354 (17) | 0.0278 (7) | |
| O5 | 0.54289 (18) | 0.3150 (3) | 0.03166 (18) | 0.0258 (6) | |
| O6 | 0.69507 (18) | 0.3630 (3) | 0.02933 (19) | 0.0269 (6) | |
| N1 | 0.6103 (2) | 0.6270 (4) | 0.13009 (19) | 0.0196 (7) | |
| H1A | 0.573 | 0.7084 | 0.0982 | 0.029* | |
| H1B | 0.6009 | 0.5329 | 0.096 | 0.029* | |
| H1C | 0.6696 | 0.6591 | 0.1431 | 0.029* | |
| N2 | 0.6200 (2) | 0.8364 (4) | 0.4365 (2) | 0.0212 (7) | |
| H2A | 0.6818 | 0.847 | 0.452 | 0.032* | |
| H2B | 0.6044 | 0.8095 | 0.4869 | 0.032* | |
| H2C | 0.593 | 0.9337 | 0.4131 | 0.032* | |
| C1 | 0.5895 (3) | 0.5948 (5) | 0.2172 (2) | 0.0219 (8) | |
| H1D | 0.6272 | 0.5012 | 0.2498 | 0.026* | |
| H1E | 0.5244 | 0.5635 | 0.203 | 0.026* | |
| C2 | 0.6087 (3) | 0.7453 (4) | 0.2779 (3) | 0.0187 (8) | |
| H2D | 0.5697 | 0.8384 | 0.2466 | 0.022* | |
| H2E | 0.6734 | 0.7786 | 0.2915 | 0.022* | |
| C3 | 0.5889 (3) | 0.7041 (5) | 0.3668 (3) | 0.0225 (8) | |
| H3A | 0.5223 | 0.6875 | 0.3535 | 0.027* | |
| H3B | 0.6198 | 0.5993 | 0.3919 | 0.027* | |
| N3 | 0.4329 (2) | 0.1615 (4) | 0.1242 (2) | 0.0190 (7) | |
| H3C | 0.4437 | 0.1667 | 0.1856 | 0.028* | |
| H3D | 0.4849 | 0.1874 | 0.1111 | 0.028* | |
| H3E | 0.415 | 0.0573 | 0.1041 | 0.028* | |
| N4 | 0.1356 (2) | 0.1252 (4) | 0.1087 (2) | 0.0203 (7) | |
| H4A | 0.1451 | 0.15 | 0.1686 | 0.03* | |
| H4B | 0.1045 | 0.028 | 0.0949 | 0.03* | |
| H4C | 0.1023 | 0.2072 | 0.073 | 0.03* | |
| C4 | 0.3591 (2) | 0.2815 (5) | 0.0775 (3) | 0.0200 (8) | |
| H4D | 0.3392 | 0.2598 | 0.011 | 0.024* | |
| H4E | 0.3842 | 0.395 | 0.0876 | 0.024* | |
| C5 | 0.2766 (2) | 0.2717 (4) | 0.1111 (3) | 0.0177 (8) | |
| H5A | 0.297 | 0.2909 | 0.1778 | 0.021* | |
| H5B | 0.2339 | 0.3618 | 0.0822 | 0.021* | |
| C6 | 0.2256 (2) | 0.1093 (5) | 0.0916 (3) | 0.0203 (8) | |
| H6A | 0.2155 | 0.0771 | 0.0272 | 0.024* | |
| H6B | 0.2624 | 0.0218 | 0.1313 | 0.024* | |
| O7 | 0.3042 (2) | 0.6953 (4) | 0.2029 (2) | 0.0331 (7) | |
| O8 | 0.7963 (2) | 0.7016 (4) | 0.1951 (2) | 0.0314 (7) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0167 (5) | 0.0170 (4) | 0.0128 (5) | 0.0005 (4) | 0.0033 (4) | −0.0004 (4) |
| S2 | 0.0206 (5) | 0.0172 (5) | 0.0235 (6) | 0.0033 (4) | 0.0015 (4) | −0.0013 (4) |
| O1 | 0.0182 (13) | 0.0211 (14) | 0.0263 (15) | −0.0018 (11) | 0.0029 (11) | −0.0002 (12) |
| O2 | 0.0306 (15) | 0.0237 (14) | 0.0184 (14) | −0.0002 (12) | 0.0105 (12) | 0.0030 (12) |
| O3 | 0.0293 (14) | 0.0276 (15) | 0.0142 (14) | 0.0045 (12) | 0.0039 (11) | −0.0043 (12) |
| S3 | 0.0165 (5) | 0.0180 (4) | 0.0130 (6) | 0.0000 (4) | 0.0028 (4) | −0.0002 (4) |
| S4 | 0.0303 (6) | 0.0188 (5) | 0.0172 (6) | 0.0008 (4) | 0.0011 (4) | 0.0019 (4) |
| O4 | 0.0443 (18) | 0.0243 (14) | 0.0123 (14) | −0.0043 (13) | 0.0052 (12) | −0.0007 (12) |
| O5 | 0.0210 (14) | 0.0282 (15) | 0.0295 (16) | 0.0047 (12) | 0.0100 (12) | 0.0047 (13) |
| O6 | 0.0197 (13) | 0.0233 (14) | 0.0356 (17) | −0.0033 (12) | 0.0056 (11) | 0.0025 (13) |
| N1 | 0.0256 (17) | 0.0181 (16) | 0.0129 (16) | 0.0017 (14) | 0.0027 (13) | −0.0032 (13) |
| N2 | 0.0196 (16) | 0.0247 (18) | 0.0181 (17) | 0.0017 (13) | 0.0043 (13) | 0.0024 (14) |
| C1 | 0.026 (2) | 0.0219 (19) | 0.017 (2) | −0.0022 (17) | 0.0068 (16) | 0.0032 (16) |
| C2 | 0.0172 (19) | 0.0190 (18) | 0.020 (2) | 0.0030 (15) | 0.0054 (15) | 0.0034 (15) |
| C3 | 0.0203 (19) | 0.023 (2) | 0.024 (2) | −0.0040 (16) | 0.0059 (16) | −0.0020 (17) |
| N3 | 0.0174 (15) | 0.0228 (16) | 0.0155 (16) | −0.0019 (13) | 0.0036 (13) | 0.0004 (13) |
| N4 | 0.0186 (16) | 0.0213 (16) | 0.0182 (17) | 0.0005 (13) | 0.0016 (13) | −0.0020 (14) |
| C4 | 0.0207 (19) | 0.0193 (19) | 0.018 (2) | −0.0014 (16) | 0.0038 (15) | 0.0033 (16) |
| C5 | 0.0183 (19) | 0.0159 (18) | 0.017 (2) | 0.0008 (15) | 0.0029 (15) | 0.0002 (15) |
| C6 | 0.0189 (18) | 0.0196 (18) | 0.021 (2) | 0.0018 (16) | 0.0039 (15) | −0.0036 (16) |
| O7 | 0.0317 (17) | 0.046 (2) | 0.0199 (17) | −0.0121 (16) | 0.0058 (14) | −0.0012 (15) |
| O8 | 0.0227 (15) | 0.0455 (19) | 0.0256 (18) | 0.0020 (14) | 0.0069 (13) | 0.0100 (15) |
Geometric parameters (Å, º) top
| S1—O3 | 1.466 (3) | C3—H3A | 0.99 |
| S1—O1 | 1.483 (3) | C3—H3B | 0.99 |
| S1—O2 | 1.496 (3) | N3—C4 | 1.497 (5) |
| S1—S2 | 2.0094 (13) | N3—H3C | 0.91 |
| S3—O6 | 1.471 (3) | N3—H3D | 0.91 |
| S3—O5 | 1.482 (3) | N3—H3E | 0.91 |
| S3—O4 | 1.482 (3) | N4—C6 | 1.496 (4) |
| S3—S4 | 2.0066 (13) | N4—H4A | 0.91 |
| N1—C1 | 1.497 (5) | N4—H4B | 0.91 |
| N1—H1A | 0.91 | N4—H4C | 0.91 |
| N1—H1B | 0.91 | C4—C5 | 1.516 (5) |
| N1—H1C | 0.91 | C4—H4D | 0.99 |
| N2—C3 | 1.485 (5) | C4—H4E | 0.99 |
| N2—H2A | 0.91 | C5—C6 | 1.512 (5) |
| N2—H2B | 0.91 | C5—H5A | 0.99 |
| N2—H2C | 0.91 | C5—H5B | 0.99 |
| C1—C2 | 1.507 (5) | C6—H6A | 0.99 |
| C1—H1D | 0.99 | C6—H6B | 0.99 |
| C1—H1E | 0.99 | O7—H7P | 0.81 (2) |
| C2—C3 | 1.532 (5) | O7—H7Q | 0.76 (3) |
| C2—H2D | 0.99 | O8—H8P | 0.79 (2) |
| C2—H2E | 0.99 | O8—H8Q | 0.83 (3) |
| O3—S1—O1 | 110.94 (16) | N2—C3—H3A | 109.1 |
| O3—S1—O2 | 109.75 (16) | C2—C3—H3A | 109.1 |
| O1—S1—O2 | 108.99 (16) | N2—C3—H3B | 109.1 |
| O3—S1—S2 | 109.11 (12) | C2—C3—H3B | 109.1 |
| O1—S1—S2 | 108.89 (12) | H3A—C3—H3B | 107.9 |
| O2—S1—S2 | 109.13 (12) | C4—N3—H3C | 109.5 |
| O6—S3—O5 | 107.96 (16) | C4—N3—H3D | 109.5 |
| O6—S3—O4 | 109.39 (16) | H3C—N3—H3D | 109.5 |
| O5—S3—O4 | 109.92 (17) | C4—N3—H3E | 109.5 |
| O6—S3—S4 | 110.60 (12) | H3C—N3—H3E | 109.5 |
| O5—S3—S4 | 109.10 (12) | H3D—N3—H3E | 109.5 |
| O4—S3—S4 | 109.86 (12) | C6—N4—H4A | 109.5 |
| C1—N1—H1A | 109.5 | C6—N4—H4B | 109.5 |
| C1—N1—H1B | 109.5 | H4A—N4—H4B | 109.5 |
| H1A—N1—H1B | 109.5 | C6—N4—H4C | 109.5 |
| C1—N1—H1C | 109.5 | H4A—N4—H4C | 109.5 |
| H1A—N1—H1C | 109.5 | H4B—N4—H4C | 109.5 |
| H1B—N1—H1C | 109.5 | N3—C4—C5 | 113.2 (3) |
| C3—N2—H2A | 109.5 | N3—C4—H4D | 108.9 |
| C3—N2—H2B | 109.5 | C5—C4—H4D | 108.9 |
| H2A—N2—H2B | 109.5 | N3—C4—H4E | 108.9 |
| C3—N2—H2C | 109.5 | C5—C4—H4E | 108.9 |
| H2A—N2—H2C | 109.5 | H4D—C4—H4E | 107.7 |
| H2B—N2—H2C | 109.5 | C6—C5—C4 | 114.7 (3) |
| N1—C1—C2 | 111.2 (3) | C6—C5—H5A | 108.6 |
| N1—C1—H1D | 109.4 | C4—C5—H5A | 108.6 |
| C2—C1—H1D | 109.4 | C6—C5—H5B | 108.6 |
| N1—C1—H1E | 109.4 | C4—C5—H5B | 108.6 |
| C2—C1—H1E | 109.4 | H5A—C5—H5B | 107.6 |
| H1D—C1—H1E | 108 | N4—C6—C5 | 110.1 (3) |
| C1—C2—C3 | 108.9 (3) | N4—C6—H6A | 109.6 |
| C1—C2—H2D | 109.9 | C5—C6—H6A | 109.6 |
| C3—C2—H2D | 109.9 | N4—C6—H6B | 109.6 |
| C1—C2—H2E | 109.9 | C5—C6—H6B | 109.6 |
| C3—C2—H2E | 109.9 | H6A—C6—H6B | 108.2 |
| H2D—C2—H2E | 108.3 | H7P—O7—H7Q | 105 (6) |
| N2—C3—C2 | 112.3 (3) | H8P—O8—H8Q | 97 (4) |
| N1—C1—C2—C3 | −178.5 (3) | N3—C4—C5—C6 | −64.3 (4) |
| C1—C2—C3—N2 | 170.8 (3) | C4—C5—C6—N4 | −167.8 (3) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| O8—H8Q···S4i | 0.83 (3) | 2.54 (3) | 3.332 (3) | 162 (4) |
| O8—H8P···O1ii | 0.79 (2) | 2.13 (3) | 2.865 (4) | 156 (4) |
| N1—H1A···O5iii | 0.91 | 2.23 | 2.885 (4) | 128 |
| N1—H1B···O5 | 0.91 | 2.08 | 2.959 (4) | 162 |
| N1—H1B···O6 | 0.91 | 2.45 | 3.154 (4) | 135 |
| N1—H1C···O8 | 0.91 | 1.9 | 2.790 (4) | 167 |
| N2—H2A···O6i | 0.91 | 1.83 | 2.739 (4) | 174 |
| N2—H2B···O2iv | 0.91 | 1.97 | 2.807 (4) | 152 |
| N2—H2C···S2v | 0.91 | 2.82 | 3.501 (3) | 133 |
| N2—H2C···O1v | 0.91 | 2.03 | 2.869 (4) | 152 |
| C1—H1E···O3vi | 0.99 | 2.57 | 3.199 (4) | 122 |
| N3—H3C···S2vi | 0.91 | 2.82 | 3.623 (3) | 147 |
| N3—H3C···O3vi | 0.91 | 2.13 | 2.893 (4) | 141 |
| N3—H3D···O5 | 0.91 | 2.01 | 2.822 (4) | 148 |
| N3—H3E···O4vii | 0.91 | 1.97 | 2.858 (4) | 166 |
| N4—H4A···O7vi | 0.91 | 1.92 | 2.816 (4) | 166 |
| N4—H4B···O2viii | 0.91 | 1.9 | 2.807 (4) | 174 |
| N4—H4C···O1ix | 0.91 | 2.53 | 3.241 (4) | 135 |
| N4—H4C···O2ix | 0.91 | 2.45 | 3.074 (4) | 126 |
| Symmetry codes: (i) −x+3/2, y+1/2, −z+1/2; (ii) x+1, y, z; (iii) −x+1, −y+1, −z; (iv) x+1/2, −y+3/2, z+1/2; (v) −x+1/2, y+1/2, −z+1/2; (vi) −x+1/2, y−1/2, −z+1/2; (vii) −x+1, −y, −z; (viii) x, y−1, z; (ix) −x, −y+1, −z. |
(Comp_3) top
Crystal data top
| C4H14N22+·O3S22− | Z = 2 |
| Mr = 202.29 | F(000) = 216 |
| Triclinic, P1 | Dx = 1.46 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 6.0538 (5) Å | Cell parameters from 1508 reflections |
| b = 8.5273 (6) Å | θ = 2.5–28.4° |
| c = 9.3869 (8) Å | µ = 0.55 mm−1 |
| α = 73.623 (7)° | T = 120 K |
| β = 82.681 (7)° | Prism, colourless |
| γ = 84.207 (7)° | 0.56 × 0.41 × 0.33 mm |
| V = 460.05 (7) Å3 |
Data collection top
| KUMA KM4CCD, Sapphire2, large Be window diffractometer | 1416 reflections with I > 2σ(I) |
| ω scans | Rint = 0.031 |
| Absorption correction: multi-scan CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. | θmax = 26.0°, θmin = 2.5° |
| Tmin = 0.775, Tmax = 1 | h = −7→7 |
| 2675 measured reflections | k = −10→10 |
| 1786 independent reflections | l = −10→11 |
Refinement top
| 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)] = 0.053 | Hydrogen site location: mixed |
| wR(F2) = 0.134 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.06 | w = 1/[σ2(Fo2) + (0.0448P)2 + 1.0795P] where P = (Fo2 + 2Fc2)/3 |
| 1786 reflections | (Δ/σ)max < 0.001 |
| 124 parameters | Δρmax = 0.57 e Å−3 |
| 6 restraints | Δρmin = −0.52 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.19150 (15) | 0.58523 (11) | 0.21277 (10) | 0.0172 (3) | |
| S2 | −0.04846 (16) | 0.73096 (12) | 0.28715 (11) | 0.0212 (3) | |
| O1 | 0.2464 (4) | 0.6464 (3) | 0.0488 (3) | 0.0226 (6) | |
| O2 | 0.3934 (4) | 0.5821 (3) | 0.2891 (3) | 0.0200 (6) | |
| O3 | 0.1141 (5) | 0.4167 (3) | 0.2488 (3) | 0.0263 (7) | |
| N1 | 0.7111 (6) | 0.3423 (4) | 0.4243 (4) | 0.0192 (7) | |
| N2 | 0.2882 (5) | 0.2887 (4) | 0.0020 (4) | 0.0184 (7) | |
| C1 | 0.4968 (6) | 0.0908 (4) | 0.4985 (4) | 0.0193 (8) | |
| H1A | 0.3707 | 0.1515 | 0.4442 | 0.023* | |
| H1B | 0.4714 | 0.1007 | 0.6019 | 0.023* | |
| C2 | 0.7139 (7) | 0.1667 (4) | 0.4227 (4) | 0.0225 (9) | |
| H2A | 0.8405 | 0.1035 | 0.4748 | 0.027* | |
| H2B | 0.7366 | 0.1602 | 0.3182 | 0.027* | |
| C3 | 0.4747 (6) | 0.0068 (4) | 0.0796 (4) | 0.0180 (8) | |
| H3A | 0.6042 | 0.0501 | 0.107 | 0.022* | |
| H3B | 0.455 | −0.104 | 0.1479 | 0.022* | |
| C4 | 0.2660 (6) | 0.1176 (4) | 0.1023 (4) | 0.0206 (8) | |
| H4A | 0.1341 | 0.0718 | 0.0805 | 0.025* | |
| H4B | 0.2423 | 0.121 | 0.2077 | 0.025* | |
| H2N | 0.430 (4) | 0.320 (4) | −0.010 (4) | 0.012 (9)* | |
| H2Q | 0.196 (6) | 0.354 (5) | 0.050 (4) | 0.026 (11)* | |
| H1N | 0.598 (6) | 0.407 (5) | 0.378 (5) | 0.034 (12)* | |
| H1M | 0.681 (9) | 0.351 (6) | 0.519 (3) | 0.053 (16)* | |
| H2M | 0.258 (9) | 0.304 (7) | −0.094 (4) | 0.070 (19)* | |
| H1Q | 0.848 (5) | 0.379 (6) | 0.384 (5) | 0.047 (15)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0190 (5) | 0.0162 (5) | 0.0176 (5) | 0.0002 (4) | −0.0032 (4) | −0.0063 (4) |
| S2 | 0.0226 (5) | 0.0208 (5) | 0.0223 (5) | 0.0043 (4) | −0.0057 (4) | −0.0099 (4) |
| O1 | 0.0258 (15) | 0.0245 (15) | 0.0159 (13) | −0.0025 (12) | −0.0033 (11) | −0.0020 (11) |
| O2 | 0.0186 (14) | 0.0224 (14) | 0.0202 (14) | 0.0041 (11) | −0.0076 (11) | −0.0075 (11) |
| O3 | 0.0298 (16) | 0.0194 (15) | 0.0318 (16) | −0.0038 (12) | 0.0042 (12) | −0.0130 (12) |
| N1 | 0.0214 (18) | 0.0153 (17) | 0.0221 (18) | −0.0005 (14) | −0.0057 (14) | −0.0057 (14) |
| N2 | 0.0206 (18) | 0.0135 (16) | 0.0204 (17) | 0.0015 (13) | −0.0012 (14) | −0.0049 (14) |
| C1 | 0.026 (2) | 0.015 (2) | 0.0163 (18) | −0.0001 (16) | −0.0044 (16) | −0.0033 (15) |
| C2 | 0.026 (2) | 0.016 (2) | 0.026 (2) | 0.0004 (16) | −0.0003 (17) | −0.0084 (17) |
| C3 | 0.026 (2) | 0.0134 (18) | 0.0147 (19) | 0.0006 (15) | −0.0023 (15) | −0.0040 (15) |
| C4 | 0.026 (2) | 0.0150 (19) | 0.0208 (19) | −0.0025 (16) | −0.0004 (16) | −0.0053 (16) |
Geometric parameters (Å, º) top
| S1—O1 | 1.485 (3) | C1—C2 | 1.525 (5) |
| S1—O2 | 1.487 (3) | C1—C1i | 1.537 (7) |
| S1—O3 | 1.491 (3) | C1—H1A | 0.99 |
| S1—S2 | 2.0021 (13) | C1—H1B | 0.99 |
| N1—C2 | 1.500 (5) | C2—H2A | 0.99 |
| N1—H1N | 0.91 (3) | C2—H2B | 0.99 |
| N1—H1M | 0.91 (3) | C3—C3ii | 1.522 (7) |
| N1—H1Q | 0.91 (3) | C3—C4 | 1.529 (5) |
| N2—C4 | 1.505 (5) | C3—H3A | 0.99 |
| N2—H2N | 0.91 (2) | C3—H3B | 0.99 |
| N2—H2Q | 0.91 (2) | C4—H4A | 0.99 |
| N2—H2M | 0.91 (3) | C4—H4B | 0.99 |
| O1—S1—O2 | 109.55 (15) | C2—C1—H1B | 109.3 |
| O1—S1—O3 | 108.95 (16) | C1i—C1—H1B | 109.3 |
| O2—S1—O3 | 109.82 (16) | H1A—C1—H1B | 108 |
| O1—S1—S2 | 111.03 (11) | N1—C2—C1 | 111.6 (3) |
| O2—S1—S2 | 108.18 (11) | N1—C2—H2A | 109.3 |
| O3—S1—S2 | 109.30 (12) | C1—C2—H2A | 109.3 |
| C2—N1—H1N | 114 (3) | N1—C2—H2B | 109.3 |
| C2—N1—H1M | 110 (3) | C1—C2—H2B | 109.3 |
| H1N—N1—H1M | 102 (4) | H2A—C2—H2B | 108 |
| C2—N1—H1Q | 107 (3) | C3ii—C3—C4 | 113.5 (4) |
| H1N—N1—H1Q | 112 (4) | C3ii—C3—H3A | 108.9 |
| H1M—N1—H1Q | 111 (4) | C4—C3—H3A | 108.9 |
| C4—N2—H2N | 112 (2) | C3ii—C3—H3B | 108.9 |
| C4—N2—H2Q | 105 (3) | C4—C3—H3B | 108.9 |
| H2N—N2—H2Q | 109 (3) | H3A—C3—H3B | 107.7 |
| C4—N2—H2M | 116 (4) | N2—C4—C3 | 111.1 (3) |
| H2N—N2—H2M | 103 (4) | N2—C4—H4A | 109.4 |
| H2Q—N2—H2M | 112 (4) | C3—C4—H4A | 109.4 |
| C2—C1—C1i | 111.5 (4) | N2—C4—H4B | 109.4 |
| C2—C1—H1A | 109.3 | C3—C4—H4B | 109.4 |
| C1i—C1—H1A | 109.3 | H4A—C4—H4B | 108 |
| C1i—C1—C2—N1 | −178.0 (4) | C3ii—C3—C4—N2 | −59.2 (5) |
| Symmetry codes: (i) −x+1, −y, −z+1; (ii) −x+1, −y, −z. |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1N···O2 | 0.91 (3) | 1.91 (3) | 2.803 (4) | 167 (4) |
| N1—H1M···O2iii | 0.91 (3) | 2.02 (3) | 2.918 (4) | 169 (5) |
| N1—H1Q···O3iv | 0.91 (3) | 1.91 (3) | 2.787 (4) | 160 (5) |
| N2—H2N···O1v | 0.91 (2) | 1.98 (3) | 2.880 (4) | 170 (3) |
| N2—H2Q···O3 | 0.91 (2) | 2.07 (3) | 2.870 (4) | 145 (3) |
| N2—H2Q···O1 | 0.91 (2) | 2.54 (4) | 3.183 (4) | 128 (3) |
| N2—H2M···S2vi | 0.91 (3) | 2.44 (3) | 3.288 (3) | 155 (5) |
| Symmetry codes: (iii) −x+1, −y+1, −z+1; (iv) x+1, y, z; (v) −x+1, −y+1, −z; (vi) −x, −y+1, −z. |
(Comp_4) top
Crystal data top
| C5H16N22+·O3S22−·0.5(O) | Dx = 1.317 Mg m−3 |
| Mr = 224.32 | Mo Kα radiation, λ = 0.71073 Å |
| Tetragonal, P43212 | Cell parameters from 2539 reflections |
| Hall symbol: P 4nw 2abw | θ = 3.9–26.1° |
| a = 11.7872 (9) Å | µ = 0.45 mm−1 |
| c = 16.2851 (14) Å | T = 120 K |
| V = 2262.6 (4) Å3 | Needle, colourless |
| Z = 8 | 0.36 × 0.06 × 0.04 mm |
| F(000) = 960 |
Data collection top
| STOE IPDS 2T diffractometer | 1762 reflections with I > 2σ(I) |
| Radiation source: GeniX Mo, 0.05 x 0.05 mm2 microfocus | Rint = 0.076 |
| Parabolic x-ray mirror monochromator | θmax = 25.1°, θmin = 2.4° |
| Detector resolution: 6.67 pixels mm-1 | h = −14→14 |
| rotation method scans | k = −14→14 |
| 15572 measured reflections | l = −19→19 |
| 2008 independent reflections |
Refinement top
| Refinement on F2 | Hydrogen site location: inferred from neighbouring sites |
| Least-squares matrix: full | H-atom parameters constrained |
| R[F2 > 2σ(F2)] = 0.059 | w = 1/[σ2(Fo2) + (0.1379P)2] where P = (Fo2 + 2Fc2)/3 |
| wR(F2) = 0.167 | (Δ/σ)max < 0.001 |
| S = 1.03 | Δρmax = 0.90 e Å−3 |
| 2008 reflections | Δρmin = −0.68 e Å−3 |
| 117 parameters | Absolute structure: Flack x determined using 669 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). |
| 0 restraints | Absolute structure parameter: 0.00 (13) |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | Occ. (<1) | |
| N1 | 0.7463 (5) | −0.0554 (4) | 0.0691 (3) | 0.0210 (11) | |
| H1A | 0.7856 | −0.0539 | 0.0211 | 0.025* | |
| H1B | 0.6871 | −0.1046 | 0.0646 | 0.025* | |
| H1C | 0.7929 | −0.0786 | 0.1104 | 0.025* | |
| N2 | 0.4337 (4) | 0.2722 (4) | 0.3846 (3) | 0.0203 (11) | |
| H2A | 0.3984 | 0.2038 | 0.3889 | 0.024* | |
| H2B | 0.3823 | 0.3287 | 0.3926 | 0.024* | |
| H2C | 0.4894 | 0.2771 | 0.4231 | 0.024* | |
| C1 | 0.7025 (6) | 0.0601 (5) | 0.0878 (4) | 0.0256 (14) | |
| H1D | 0.6446 | 0.0816 | 0.0466 | 0.031* | |
| H1E | 0.7654 | 0.1157 | 0.0845 | 0.031* | |
| C2 | 0.6504 (6) | 0.0631 (5) | 0.1734 (4) | 0.0230 (14) | |
| H2D | 0.5908 | 0.0042 | 0.1772 | 0.028* | |
| H2E | 0.7096 | 0.045 | 0.2144 | 0.028* | |
| C3 | 0.5990 (6) | 0.1776 (6) | 0.1935 (4) | 0.0252 (14) | |
| H3A | 0.5376 | 0.1949 | 0.1539 | 0.03* | |
| H3B | 0.6577 | 0.2372 | 0.1884 | 0.03* | |
| C4 | 0.5510 (6) | 0.1781 (5) | 0.2806 (4) | 0.0233 (13) | |
| H4A | 0.5011 | 0.1113 | 0.2876 | 0.028* | |
| H4B | 0.6144 | 0.1708 | 0.3201 | 0.028* | |
| C5 | 0.4849 (5) | 0.2835 (5) | 0.3004 (4) | 0.0234 (13) | |
| H5A | 0.4241 | 0.2946 | 0.2592 | 0.028* | |
| H5B | 0.5356 | 0.3504 | 0.2987 | 0.028* | |
| S1 | 0.25562 (12) | 0.52205 (12) | 0.39555 (9) | 0.0183 (4) | |
| S2 | 0.29084 (13) | 0.64220 (13) | 0.47934 (10) | 0.0225 (4) | |
| O1 | 0.2426 (4) | 0.4114 (3) | 0.4374 (3) | 0.0221 (9) | |
| O2 | 0.1517 (4) | 0.5515 (3) | 0.3516 (3) | 0.0236 (10) | |
| O3 | 0.3515 (4) | 0.5164 (4) | 0.3367 (3) | 0.0230 (10) | |
| O4 | 0.9579 (11) | 0.0803 (11) | 0.1533 (9) | 0.035 (3)* | 0.372 (8) |
| O4A | 0.9298 (17) | 0.0702 (17) | 0.25 | 0.035 (3)* | 0.255 (15) |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| N1 | 0.027 (3) | 0.025 (2) | 0.011 (3) | 0.001 (2) | 0.001 (2) | 0.000 (2) |
| N2 | 0.023 (2) | 0.022 (3) | 0.017 (3) | 0.001 (2) | 0.0008 (19) | −0.001 (2) |
| C1 | 0.037 (4) | 0.027 (3) | 0.013 (3) | 0.006 (3) | 0.006 (3) | 0.001 (2) |
| C2 | 0.029 (3) | 0.027 (3) | 0.013 (3) | −0.001 (3) | 0.007 (2) | 0.000 (2) |
| C3 | 0.031 (3) | 0.025 (3) | 0.020 (3) | −0.003 (3) | 0.005 (3) | 0.002 (3) |
| C4 | 0.028 (3) | 0.025 (3) | 0.017 (3) | 0.001 (2) | 0.002 (3) | −0.001 (2) |
| C5 | 0.027 (3) | 0.028 (3) | 0.015 (3) | 0.001 (3) | 0.002 (2) | 0.001 (2) |
| S1 | 0.0215 (7) | 0.0183 (7) | 0.0150 (8) | 0.0013 (5) | 0.0013 (6) | 0.0009 (5) |
| S2 | 0.0291 (9) | 0.0203 (8) | 0.0182 (8) | −0.0021 (6) | −0.0011 (6) | −0.0008 (6) |
| O1 | 0.029 (2) | 0.018 (2) | 0.019 (2) | 0.0001 (17) | −0.0010 (19) | 0.0018 (18) |
| O2 | 0.025 (2) | 0.023 (2) | 0.024 (2) | 0.0018 (17) | −0.0027 (18) | −0.0015 (17) |
| O3 | 0.024 (2) | 0.030 (2) | 0.015 (2) | 0.0018 (18) | 0.0071 (18) | 0.0013 (18) |
Geometric parameters (Å, º) top
| N1—C1 | 1.488 (8) | C2—H2E | 0.99 |
| N1—H1A | 0.91 | C3—C4 | 1.526 (9) |
| N1—H1B | 0.91 | C3—H3A | 0.99 |
| N1—H1C | 0.91 | C3—H3B | 0.99 |
| N2—C5 | 1.503 (8) | C4—C5 | 1.502 (9) |
| N2—H2A | 0.91 | C4—H4A | 0.99 |
| N2—H2B | 0.91 | C4—H4B | 0.99 |
| N2—H2C | 0.91 | C5—H5A | 0.99 |
| C1—C2 | 1.524 (8) | C5—H5B | 0.99 |
| C1—H1D | 0.99 | S1—O2 | 1.461 (5) |
| C1—H1E | 0.99 | S1—O1 | 1.480 (4) |
| C2—C3 | 1.515 (9) | S1—O3 | 1.483 (4) |
| C2—H2D | 0.99 | S1—S2 | 2.010 (2) |
| C1—N1—H1A | 109.5 | C2—C3—C4 | 110.6 (5) |
| C1—N1—H1B | 109.5 | C2—C3—H3A | 109.5 |
| H1A—N1—H1B | 109.5 | C4—C3—H3A | 109.5 |
| C1—N1—H1C | 109.5 | C2—C3—H3B | 109.5 |
| H1A—N1—H1C | 109.5 | C4—C3—H3B | 109.5 |
| H1B—N1—H1C | 109.5 | H3A—C3—H3B | 108.1 |
| C5—N2—H2A | 109.5 | C5—C4—C3 | 113.3 (5) |
| C5—N2—H2B | 109.5 | C5—C4—H4A | 108.9 |
| H2A—N2—H2B | 109.5 | C3—C4—H4A | 108.9 |
| C5—N2—H2C | 109.5 | C5—C4—H4B | 108.9 |
| H2A—N2—H2C | 109.5 | C3—C4—H4B | 108.9 |
| H2B—N2—H2C | 109.5 | H4A—C4—H4B | 107.7 |
| N1—C1—C2 | 110.3 (5) | C4—C5—N2 | 109.3 (5) |
| N1—C1—H1D | 109.6 | C4—C5—H5A | 109.8 |
| C2—C1—H1D | 109.6 | N2—C5—H5A | 109.8 |
| N1—C1—H1E | 109.6 | C4—C5—H5B | 109.8 |
| C2—C1—H1E | 109.6 | N2—C5—H5B | 109.8 |
| H1D—C1—H1E | 108.1 | H5A—C5—H5B | 108.3 |
| C3—C2—C1 | 112.3 (5) | O2—S1—O1 | 110.4 (3) |
| C3—C2—H2D | 109.1 | O2—S1—O3 | 109.4 (3) |
| C1—C2—H2D | 109.1 | O1—S1—O3 | 109.7 (3) |
| C3—C2—H2E | 109.1 | O2—S1—S2 | 109.80 (19) |
| C1—C2—H2E | 109.1 | O1—S1—S2 | 109.3 (2) |
| H2D—C2—H2E | 107.9 | O3—S1—S2 | 108.21 (19) |
| N1—C1—C2—C3 | −177.0 (5) | C2—C3—C4—C5 | −172.1 (5) |
| C1—C2—C3—C4 | −178.3 (6) | C3—C4—C5—N2 | 175.6 (5) |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1A···O2i | 0.91 | 2.55 | 2.996 (7) | 111 |
| N1—H1A···O3i | 0.91 | 1.97 | 2.863 (7) | 166 |
| N1—H1B···O1ii | 0.91 | 2 | 2.887 (7) | 165 |
| N1—H1C···S2iii | 0.91 | 2.59 | 3.437 (6) | 155 |
| N1—H1C···O3iii | 0.91 | 2.42 | 3.018 (7) | 123 |
| C1—H1E···O4 | 0.99 | 2.56 | 3.202 (15) | 122 |
| N2—H2A···O2iv | 0.91 | 1.9 | 2.798 (6) | 171 |
| N2—H2B···O1 | 0.91 | 2.05 | 2.916 (7) | 159 |
| N2—H2B···O3 | 0.91 | 2.42 | 3.136 (7) | 136 |
| N2—H2C···S2v | 0.91 | 2.41 | 3.317 (6) | 178 |
| N2—H2C···O1v | 0.91 | 2.48 | 2.932 (7) | 111 |
| C2—H2D···O2ii | 0.99 | 2.53 | 3.499 (8) | 165 |
| Symmetry codes: (i) x+1/2, −y+1/2, −z+1/4; (ii) −y+1, −x, −z+1/2; (iii) −y+3/2, x−1/2, z−1/4; (iv) −x+1/2, y−1/2, −z+3/4; (v) y, x, −z+1. |
(Comp_5) top
Crystal data top
| C6H18N22+·O3S22− | Z = 4 |
| Mr = 230.34 | F(000) = 496 |
| Triclinic, P1 | Dx = 1.329 Mg m−3 |
| Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
| a = 10.4922 (10) Å | Cell parameters from 4553 reflections |
| b = 11.1455 (11) Å | θ = 3.6–28.6° |
| c = 11.7015 (12) Å | µ = 0.45 mm−1 |
| α = 62.299 (7)° | T = 120 K |
| β = 74.938 (8)° | Prism, colourless |
| γ = 74.082 (8)° | 0.31 × 0.22 × 0.15 mm |
| V = 1150.9 (2) Å3 |
Data collection top
| STOE IPDS 2T diffractometer | 3644 reflections with I > 2σ(I) |
| Radiation source: GeniX Mo, 0.05 x 0.05 mm2 microfocus | Rint = 0.114 |
| Parabolic x-ray mirror monochromator | θmax = 25.1°, θmin = 2.5° |
| Detector resolution: 6.67 pixels mm-1 | h = −12→12 |
| rotation method scans | k = −12→13 |
| 4093 measured reflections | l = −13→13 |
| 4093 independent reflections |
Refinement top
| 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)] = 0.078 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.239 | H-atom parameters constrained |
| S = 1.17 | w = 1/[σ2(Fo2) + (0.0683P)2 + 7.9349P] where P = (Fo2 + 2Fc2)/3 |
| 4093 reflections | (Δ/σ)max < 0.001 |
| 240 parameters | Δρmax = 1.17 e Å−3 |
| 0 restraints | Δρmin = −1.35 e Å−3 |
Special details top
Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. |
Refinement. Refined as a 2-component twin. |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1 | 0.26220 (14) | 0.86841 (15) | 0.09295 (14) | 0.0149 (4) | |
| S2 | 0.30555 (15) | 0.78301 (16) | −0.03202 (15) | 0.0200 (4) | |
| O1 | 0.1145 (4) | 0.9036 (5) | 0.1245 (4) | 0.0207 (10) | |
| O2 | 0.3199 (4) | 0.9946 (4) | 0.0361 (4) | 0.0211 (10) | |
| O3 | 0.3168 (5) | 0.7706 (5) | 0.2156 (4) | 0.0231 (10) | |
| S3 | 0.22643 (14) | 0.42078 (15) | 0.63449 (14) | 0.0161 (4) | |
| S4 | 0.20857 (16) | 0.58653 (17) | 0.66435 (18) | 0.0252 (4) | |
| O4 | 0.3710 (4) | 0.3706 (4) | 0.5994 (4) | 0.0207 (10) | |
| O5 | 0.1726 (5) | 0.3093 (5) | 0.7523 (4) | 0.0282 (11) | |
| O6 | 0.1568 (5) | 0.4567 (5) | 0.5254 (5) | 0.0271 (11) | |
| N1 | 0.0201 (5) | 0.1987 (5) | −0.0016 (5) | 0.0170 (11) | |
| H1C | 0.0613 | 0.2453 | −0.0841 | 0.026* | |
| H1D | −0.0663 | 0.1997 | −0.0037 | 0.026* | |
| H1E | 0.0643 | 0.1101 | 0.0319 | 0.026* | |
| N2 | 0.4619 (5) | 0.5007 (5) | 0.3260 (5) | 0.0170 (11) | |
| H2C | 0.4145 | 0.5882 | 0.3001 | 0.025* | |
| H2D | 0.549 | 0.5015 | 0.3238 | 0.025* | |
| H2E | 0.4263 | 0.4478 | 0.4088 | 0.025* | |
| C1 | 0.0218 (6) | 0.2662 (7) | 0.0822 (6) | 0.0208 (13) | |
| H1A | −0.0001 | 0.203 | 0.1753 | 0.025* | |
| H1B | −0.0478 | 0.3506 | 0.0629 | 0.025* | |
| C2 | 0.1572 (6) | 0.3034 (7) | 0.0592 (6) | 0.0202 (13) | |
| H2A | 0.1744 | 0.3745 | −0.0312 | 0.024* | |
| H2B | 0.2278 | 0.2209 | 0.0686 | 0.024* | |
| C3 | 0.1652 (6) | 0.3575 (7) | 0.1547 (6) | 0.0198 (13) | |
| H3A | 0.0983 | 0.4432 | 0.141 | 0.024* | |
| H3B | 0.1413 | 0.2889 | 0.245 | 0.024* | |
| C4 | 0.3027 (6) | 0.3869 (6) | 0.1404 (6) | 0.0187 (13) | |
| H4A | 0.3232 | 0.4617 | 0.0529 | 0.022* | |
| H4B | 0.3708 | 0.3036 | 0.1462 | 0.022* | |
| C5 | 0.3128 (6) | 0.4289 (7) | 0.2446 (6) | 0.0186 (13) | |
| H5A | 0.2522 | 0.518 | 0.2328 | 0.022* | |
| H5B | 0.2835 | 0.3589 | 0.3323 | 0.022* | |
| C6 | 0.4550 (6) | 0.4426 (7) | 0.2360 (6) | 0.0208 (13) | |
| H6A | 0.5136 | 0.3509 | 0.2591 | 0.025* | |
| H6B | 0.4885 | 0.5034 | 0.1452 | 0.025* | |
| N3 | −0.0282 (5) | 0.2722 (5) | 0.6117 (5) | 0.0197 (11) | |
| H3C | −0.0682 | 0.2337 | 0.6963 | 0.03* | |
| H3D | −0.0913 | 0.331 | 0.5607 | 0.03* | |
| H3E | 0.0336 | 0.3193 | 0.6055 | 0.03* | |
| N4 | 0.5354 (5) | −0.1129 (5) | 0.2100 (5) | 0.0164 (10) | |
| H4C | 0.5875 | −0.1869 | 0.2642 | 0.025* | |
| H4D | 0.5873 | −0.0688 | 0.1331 | 0.025* | |
| H4E | 0.4711 | −0.1418 | 0.1946 | 0.025* | |
| C7 | 0.0390 (6) | 0.1626 (7) | 0.5673 (6) | 0.0235 (14) | |
| H7A | 0.0742 | 0.205 | 0.4728 | 0.028* | |
| H7B | −0.0271 | 0.1071 | 0.5802 | 0.028* | |
| C8 | 0.1535 (6) | 0.0694 (6) | 0.6420 (6) | 0.0211 (13) | |
| H8A | 0.1172 | 0.0238 | 0.7359 | 0.025* | |
| H8B | 0.2167 | 0.126 | 0.6329 | 0.025* | |
| C9 | 0.2296 (7) | −0.0411 (7) | 0.5933 (6) | 0.0233 (14) | |
| H9A | 0.2888 | −0.111 | 0.6567 | 0.028* | |
| H9B | 0.1643 | −0.0879 | 0.5892 | 0.028* | |
| C10 | 0.3141 (7) | 0.0184 (7) | 0.4589 (7) | 0.0226 (14) | |
| H10A | 0.2546 | 0.0899 | 0.3966 | 0.027* | |
| H10B | 0.3798 | 0.064 | 0.464 | 0.027* | |
| C11 | 0.3894 (6) | −0.0867 (6) | 0.4053 (6) | 0.0209 (13) | |
| H11A | 0.4501 | −0.1585 | 0.4662 | 0.025* | |
| H11B | 0.3248 | −0.1317 | 0.3976 | 0.025* | |
| C12 | 0.4707 (6) | −0.0168 (6) | 0.2721 (6) | 0.0186 (13) | |
| H12A | 0.411 | 0.0614 | 0.2146 | 0.022* | |
| H12B | 0.5407 | 0.0204 | 0.2819 | 0.022* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1 | 0.0123 (7) | 0.0178 (8) | 0.0155 (8) | −0.0023 (5) | −0.0033 (5) | −0.0074 (6) |
| S2 | 0.0178 (8) | 0.0243 (8) | 0.0199 (8) | −0.0044 (6) | 0.0000 (6) | −0.0121 (7) |
| O1 | 0.012 (2) | 0.030 (3) | 0.021 (2) | −0.0018 (18) | −0.0006 (17) | −0.013 (2) |
| O2 | 0.026 (2) | 0.019 (2) | 0.019 (2) | −0.0097 (18) | −0.0012 (18) | −0.008 (2) |
| O3 | 0.026 (2) | 0.020 (2) | 0.017 (2) | −0.0007 (18) | −0.0063 (18) | −0.002 (2) |
| S3 | 0.0123 (7) | 0.0188 (8) | 0.0155 (8) | −0.0016 (6) | −0.0041 (5) | −0.0055 (6) |
| S4 | 0.0177 (8) | 0.0236 (9) | 0.0377 (10) | 0.0000 (6) | −0.0054 (7) | −0.0171 (8) |
| O4 | 0.015 (2) | 0.022 (2) | 0.023 (2) | 0.0022 (17) | −0.0042 (17) | −0.010 (2) |
| O5 | 0.038 (3) | 0.026 (3) | 0.018 (2) | −0.014 (2) | 0.003 (2) | −0.006 (2) |
| O6 | 0.025 (2) | 0.033 (3) | 0.027 (3) | 0.003 (2) | −0.013 (2) | −0.015 (2) |
| N1 | 0.016 (2) | 0.023 (3) | 0.017 (3) | −0.002 (2) | −0.005 (2) | −0.013 (2) |
| N2 | 0.015 (2) | 0.020 (3) | 0.018 (3) | −0.005 (2) | −0.005 (2) | −0.007 (2) |
| C1 | 0.023 (3) | 0.027 (3) | 0.018 (3) | −0.007 (3) | −0.003 (2) | −0.012 (3) |
| C2 | 0.018 (3) | 0.028 (3) | 0.017 (3) | −0.007 (3) | −0.004 (2) | −0.010 (3) |
| C3 | 0.023 (3) | 0.023 (3) | 0.013 (3) | −0.006 (3) | −0.004 (2) | −0.006 (3) |
| C4 | 0.024 (3) | 0.018 (3) | 0.017 (3) | −0.004 (2) | −0.005 (2) | −0.008 (3) |
| C5 | 0.018 (3) | 0.025 (3) | 0.017 (3) | −0.007 (2) | 0.000 (2) | −0.011 (3) |
| C6 | 0.019 (3) | 0.025 (3) | 0.021 (3) | −0.002 (3) | −0.003 (2) | −0.013 (3) |
| N3 | 0.013 (2) | 0.021 (3) | 0.021 (3) | −0.001 (2) | 0.001 (2) | −0.008 (2) |
| N4 | 0.015 (2) | 0.020 (3) | 0.013 (2) | 0.000 (2) | −0.0033 (19) | −0.008 (2) |
| C7 | 0.022 (3) | 0.031 (4) | 0.020 (3) | 0.004 (3) | −0.004 (3) | −0.017 (3) |
| C8 | 0.024 (3) | 0.019 (3) | 0.018 (3) | 0.002 (3) | −0.004 (3) | −0.008 (3) |
| C9 | 0.031 (4) | 0.018 (3) | 0.014 (3) | 0.000 (3) | 0.000 (3) | −0.005 (3) |
| C10 | 0.022 (3) | 0.021 (3) | 0.023 (3) | −0.003 (3) | −0.001 (3) | −0.010 (3) |
| C11 | 0.023 (3) | 0.019 (3) | 0.017 (3) | −0.006 (3) | 0.002 (3) | −0.006 (3) |
| C12 | 0.016 (3) | 0.016 (3) | 0.020 (3) | 0.000 (2) | 0.000 (2) | −0.008 (3) |
Geometric parameters (Å, º) top
| S1—O2 | 1.475 (4) | C5—H5A | 0.99 |
| S1—O1 | 1.482 (4) | C5—H5B | 0.99 |
| S1—O3 | 1.485 (4) | C6—H6A | 0.99 |
| S1—S2 | 1.991 (2) | C6—H6B | 0.99 |
| S3—O5 | 1.467 (5) | N3—C7 | 1.479 (8) |
| S3—O6 | 1.473 (5) | N3—H3C | 0.91 |
| S3—O4 | 1.485 (4) | N3—H3D | 0.91 |
| S3—S4 | 1.987 (2) | N3—H3E | 0.91 |
| N1—C1 | 1.493 (8) | N4—C12 | 1.485 (7) |
| N1—H1C | 0.91 | N4—H4C | 0.91 |
| N1—H1D | 0.91 | N4—H4D | 0.91 |
| N1—H1E | 0.91 | N4—H4E | 0.91 |
| N2—C6 | 1.494 (8) | C7—C8 | 1.518 (9) |
| N2—H2C | 0.91 | C7—H7A | 0.99 |
| N2—H2D | 0.91 | C7—H7B | 0.99 |
| N2—H2E | 0.91 | C8—C9 | 1.535 (8) |
| C1—C2 | 1.512 (8) | C8—H8A | 0.99 |
| C1—H1A | 0.99 | C8—H8B | 0.99 |
| C1—H1B | 0.99 | C9—C10 | 1.525 (9) |
| C2—C3 | 1.524 (8) | C9—H9A | 0.99 |
| C2—H2A | 0.99 | C9—H9B | 0.99 |
| C2—H2B | 0.99 | C10—C11 | 1.519 (9) |
| C3—C4 | 1.517 (9) | C10—H10A | 0.99 |
| C3—H3A | 0.99 | C10—H10B | 0.99 |
| C3—H3B | 0.99 | C11—C12 | 1.519 (9) |
| C4—C5 | 1.530 (8) | C11—H11A | 0.99 |
| C4—H4A | 0.99 | C11—H11B | 0.99 |
| C4—H4B | 0.99 | C12—H12A | 0.99 |
| C5—C6 | 1.514 (8) | C12—H12B | 0.99 |
| O2—S1—O1 | 109.2 (3) | N2—C6—C5 | 111.3 (5) |
| O2—S1—O3 | 108.6 (3) | N2—C6—H6A | 109.4 |
| O1—S1—O3 | 108.8 (3) | C5—C6—H6A | 109.4 |
| O2—S1—S2 | 110.83 (19) | N2—C6—H6B | 109.4 |
| O1—S1—S2 | 109.03 (19) | C5—C6—H6B | 109.4 |
| O3—S1—S2 | 110.3 (2) | H6A—C6—H6B | 108 |
| O5—S3—O6 | 110.0 (3) | C7—N3—H3C | 109.5 |
| O5—S3—O4 | 108.1 (3) | C7—N3—H3D | 109.5 |
| O6—S3—O4 | 108.6 (3) | H3C—N3—H3D | 109.5 |
| O5—S3—S4 | 111.5 (2) | C7—N3—H3E | 109.5 |
| O6—S3—S4 | 109.9 (2) | H3C—N3—H3E | 109.5 |
| O4—S3—S4 | 108.75 (19) | H3D—N3—H3E | 109.5 |
| C1—N1—H1C | 109.5 | C12—N4—H4C | 109.5 |
| C1—N1—H1D | 109.5 | C12—N4—H4D | 109.5 |
| H1C—N1—H1D | 109.5 | H4C—N4—H4D | 109.5 |
| C1—N1—H1E | 109.5 | C12—N4—H4E | 109.5 |
| H1C—N1—H1E | 109.5 | H4C—N4—H4E | 109.5 |
| H1D—N1—H1E | 109.5 | H4D—N4—H4E | 109.5 |
| C6—N2—H2C | 109.5 | N3—C7—C8 | 111.2 (5) |
| C6—N2—H2D | 109.5 | N3—C7—H7A | 109.4 |
| H2C—N2—H2D | 109.5 | C8—C7—H7A | 109.4 |
| C6—N2—H2E | 109.5 | N3—C7—H7B | 109.4 |
| H2C—N2—H2E | 109.5 | C8—C7—H7B | 109.4 |
| H2D—N2—H2E | 109.5 | H7A—C7—H7B | 108 |
| N1—C1—C2 | 111.4 (5) | C7—C8—C9 | 112.3 (5) |
| N1—C1—H1A | 109.3 | C7—C8—H8A | 109.1 |
| C2—C1—H1A | 109.3 | C9—C8—H8A | 109.1 |
| N1—C1—H1B | 109.3 | C7—C8—H8B | 109.1 |
| C2—C1—H1B | 109.3 | C9—C8—H8B | 109.1 |
| H1A—C1—H1B | 108 | H8A—C8—H8B | 107.9 |
| C1—C2—C3 | 111.9 (5) | C10—C9—C8 | 112.6 (5) |
| C1—C2—H2A | 109.2 | C10—C9—H9A | 109.1 |
| C3—C2—H2A | 109.2 | C8—C9—H9A | 109.1 |
| C1—C2—H2B | 109.2 | C10—C9—H9B | 109.1 |
| C3—C2—H2B | 109.2 | C8—C9—H9B | 109.1 |
| H2A—C2—H2B | 107.9 | H9A—C9—H9B | 107.8 |
| C4—C3—C2 | 113.4 (5) | C11—C10—C9 | 114.6 (5) |
| C4—C3—H3A | 108.9 | C11—C10—H10A | 108.6 |
| C2—C3—H3A | 108.9 | C9—C10—H10A | 108.6 |
| C4—C3—H3B | 108.9 | C11—C10—H10B | 108.6 |
| C2—C3—H3B | 108.9 | C9—C10—H10B | 108.6 |
| H3A—C3—H3B | 107.7 | H10A—C10—H10B | 107.6 |
| C3—C4—C5 | 112.8 (5) | C12—C11—C10 | 110.2 (5) |
| C3—C4—H4A | 109 | C12—C11—H11A | 109.6 |
| C5—C4—H4A | 109 | C10—C11—H11A | 109.6 |
| C3—C4—H4B | 109 | C12—C11—H11B | 109.6 |
| C5—C4—H4B | 109 | C10—C11—H11B | 109.6 |
| H4A—C4—H4B | 107.8 | H11A—C11—H11B | 108.1 |
| C6—C5—C4 | 111.2 (5) | N4—C12—C11 | 112.1 (5) |
| C6—C5—H5A | 109.4 | N4—C12—H12A | 109.2 |
| C4—C5—H5A | 109.4 | C11—C12—H12A | 109.2 |
| C6—C5—H5B | 109.4 | N4—C12—H12B | 109.2 |
| C4—C5—H5B | 109.4 | C11—C12—H12B | 109.2 |
| H5A—C5—H5B | 108 | H12A—C12—H12B | 107.9 |
Hydrogen-bond geometry (Å, º) top
| D—H···A | D—H | H···A | D···A | D—H···A |
| N1—H1C···O5i | 0.91 | 1.89 | 2.786 (7) | 169 |
| N1—H1D···O1ii | 0.91 | 2.41 | 2.971 (6) | 120 |
| N1—H1D···S2ii | 0.91 | 2.4 | 3.296 (5) | 167 |
| N1—H1E···O1iii | 0.91 | 2.02 | 2.905 (7) | 165 |
| N2—H2C···O3 | 0.91 | 1.92 | 2.816 (7) | 169 |
| N2—H2D···O4iv | 0.91 | 2.41 | 3.039 (6) | 127 |
| N2—H2D···S4iv | 0.91 | 2.48 | 3.342 (5) | 159 |
| N2—H2E···O4 | 0.91 | 1.97 | 2.848 (7) | 163 |
| N3—H3C···O1v | 0.91 | 1.97 | 2.843 (7) | 161 |
| N3—H3C···O3v | 0.91 | 2.55 | 3.193 (7) | 128 |
| N3—H3D···O6v | 0.91 | 2.08 | 2.812 (7) | 136 |
| N3—H3D···S4v | 0.91 | 2.85 | 3.648 (6) | 148 |
| N3—H3E···O6 | 0.91 | 2 | 2.874 (7) | 159 |
| N3—H3E···O5 | 0.91 | 2.48 | 3.199 (7) | 137 |
| N4—H4C···O4vi | 0.91 | 1.94 | 2.798 (7) | 156 |
| N4—H4C···O5vi | 0.91 | 2.52 | 3.240 (7) | 137 |
| N4—H4D···O2vii | 0.91 | 1.86 | 2.762 (7) | 170 |
| N4—H4E···O3iii | 0.91 | 2.02 | 2.904 (7) | 164 |
| N4—H4E···O2iii | 0.91 | 2.42 | 3.054 (7) | 127 |
| Symmetry codes: (i) x, y, z−1; (ii) −x, −y+1, −z; (iii) x, y−1, z; (iv) −x+1, −y+1, −z+1; (v) −x, −y+1, −z+1; (vi) −x+1, −y, −z+1; (vii) −x+1, −y+1, −z. |
