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A series of molecular adducts of 2-aminothiazole derivatives - 2-aminothiazole, 2-amino-2-thiazoline and 2-aminobenzothiazole with the carboxylic-acid-substituted heterocyclics indole-2-carboxylic acid, N-methylpyrrole-2-carboxylic acid and thiophene-2-carboxylic acid - have been prepared and characterized using X-ray powder diffraction and in five cases by single-crystal X-ray diffraction methods. These five compounds are the adducts of 2-amino-2-thiazolium with indole-2-carboxylate [(C3H7N2S)+(C9H6NO2)-], and N-methylpyrrole-2-carboxylate [(C3H7N2S)+-(C6H6NO2)-], 2-aminobenzothiazolium with indole-2-carboxylate [(C7H7N2S)+(C9H6NO2)-], N-methylpyrrole-2-carboxylate [(C7H7N2S)+(C6H6NO2)-] and thiophene-2-carboxylate [(C7H7N2S)+(C5H3O2S)-]. All complexes involve proton transfer, as indicated by IR spectroscopy, while the five crystal structures display similar hydrogen-bonding patterns with the dominant interaction being an 
graph set dimer association between carboxylate groups and the amine/heterocyclic nitrogen sites. Futhermore, in each case a subsiduary interaction between an amino proton and a carboxylate oxygen completes a linear hydrogen-bonded chain. In addition to this, the indole-2-carboxylate molecules in the adduct structure with 2-amino-2-thiazolium form associated dimers which add to the hydrogen-bonding network.
graph set dimer association between carboxylate groups and the amine/heterocyclic nitrogen sites. Futhermore, in each case a subsiduary interaction between an amino proton and a carboxylate oxygen completes a linear hydrogen-bonded chain. In addition to this, the indole-2-carboxylate molecules in the adduct structure with 2-amino-2-thiazolium form associated dimers which add to the hydrogen-bonding network.Supporting information
 | Crystallographic Information File (CIF) |
 | Structure factor file (SHELXL table format) |
| Structure factor file (SHELXL table format) |
| Structure factor file (SHELXL table format) |
| Structure factor file (SHELXL table format) |
| Structure factor file (SHELXL table format) |
CCDC references: 136444; 136445; 136446; 136447; 136448
Computing details top
For all compounds, data collection: MolEN (Fair,1990); cell refinement: MolEN (Fair,1990); data reduction: Xtal3.2 (Hall et al., 1992); program(s) used to solve structure: SHELXS97(Sheldrick, 1997); program(s) used to refine structure: SHELXL97(Sheldrick, 1997); molecular graphics: PLUTON94 (Spek, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).
![[Figure 1]](http://journals.iucr.org/b/issues/1999/05/00/ha0177/ha0177fig1thm.gif)
![[Figure 2]](http://journals.iucr.org/b/issues/1999/05/00/ha0177/ha0177fig2thm.gif)
(4) 2-amino-2-thiazolinium indole-2-carboxylate top
Crystal data top
| C3H7N2S+·C9H6NO2− | F(000) = 552 |
| Mr = 263.31 | Dx = 1.426 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 8.771 (2) Å | θ = 6–14° |
| b = 13.344 (5) Å | µ = 0.26 mm−1 |
| c = 11.036 (2) Å | T = 298 K |
| β = 108.314 (8)° | Prism, colourless |
| V = 1226.2 (6) Å3 | 0.50 × 0.30 × 0.24 mm |
| Z = 4 |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1400 reflections with F > 4σ(F) |
| Radiation source: fine-focus sealed tube | Rint = 0.018 |
| Graphite monochromator | θmax = 25.0°, θmin = 2.5° |
| 2θ–ω scans | h = 0→10 |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | k = 0→15 |
| Tmin = 0.857, Tmax = 0.939 | l = −13→12 |
| 2295 measured reflections | 3 standard reflections every 200 reflections |
| 2147 independent reflections | intensity decay: 1% |
Refinement top
| 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)] = 0.036 | All H-atom parameters refined |
| wR(F2) = 0.101 | Calculated w = 1/[σ2(Fo2) + (0.0499P)2 + 0.2456P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.001 |
| 2147 reflections | Δρmax = 0.17 e Å−3 |
| 216 parameters | Δρmin = −0.14 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0036 (14) |
Crystal data top
| C3H7N2S+·C9H6NO2− | V = 1226.2 (6) Å3 |
| Mr = 263.31 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 8.771 (2) Å | µ = 0.26 mm−1 |
| b = 13.344 (5) Å | T = 298 K |
| c = 11.036 (2) Å | 0.50 × 0.30 × 0.24 mm |
| β = 108.314 (8)° |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1400 reflections with F > 4σ(F) |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | Rint = 0.018 |
| Tmin = 0.857, Tmax = 0.939 | 3 standard reflections every 200 reflections |
| 2295 measured reflections | intensity decay: 1% |
| 2147 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.036 | 0 restraints |
| wR(F2) = 0.101 | All H-atom parameters refined |
| S = 1.00 | Δρmax = 0.17 e Å−3 |
| 2147 reflections | Δρmin = −0.14 e Å−3 |
| 216 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.19795 (9) | 0.00838 (5) | 0.63845 (7) | 0.0583 (3) | |
| N3A | 0.1661 (3) | 0.16112 (17) | 0.76836 (18) | 0.0496 (6) | |
| C2A | 0.1381 (3) | 0.13027 (18) | 0.6507 (2) | 0.0436 (6) | |
| N21A | 0.0701 (3) | 0.18557 (18) | 0.5505 (2) | 0.0532 (6) | |
| C4A | 0.2472 (5) | 0.0918 (2) | 0.8682 (3) | 0.0635 (8) | |
| C5A | 0.2952 (5) | 0.0013 (3) | 0.8081 (3) | 0.0687 (8) | |
| H21A | 0.0460 (3) | 0.2540 (2) | 0.5610 (2) | 0.065 (8)* | |
| H22A | 0.0720 (3) | 0.1660 (2) | 0.4710 (3) | 0.070 (9)* | |
| H3A | 0.1470 (3) | 0.2280 (2) | 0.7850 (2) | 0.0580 (8)* | |
| H41A | 0.3310 (4) | 0.1230 (3) | 0.9240 (3) | 0.1010 (13)* | |
| H42A | 0.1690 (4) | 0.0740 (3) | 0.9120 (3) | 0.1070 (13)* | |
| H51A | 0.2650 (4) | −0.0600 (3) | 0.8350 (3) | 0.087 (11)* | |
| H52A | 0.4130 (5) | 0.0040 (3) | 0.8190 (3) | 0.116 (14)* | |
| N1B | 0.1919 (3) | −0.07169 (15) | 0.13668 (19) | 0.0430 (5) | |
| C2B | 0.2073 (3) | −0.00759 (17) | 0.23742 (19) | 0.0387 (5) | |
| C21B | 0.1162 (3) | 0.08695 (17) | 0.2207 (2) | 0.0412 (6) | |
| O21B | 0.1345 (2) | 0.14099 (12) | 0.31775 (14) | 0.0502 (5) | |
| O22B | 0.0295 (2) | 0.10985 (12) | 0.10943 (15) | 0.0527 (5) | |
| C3B | 0.3233 (3) | −0.04403 (19) | 0.3415 (2) | 0.0432 (6) | |
| C4B | 0.5028 (3) | −0.2028 (2) | 0.3675 (2) | 0.0484 (6) | |
| C5B | 0.5308 (3) | −0.2837 (2) | 0.3011 (3) | 0.0514 (7) | |
| C6B | 0.4424 (3) | −0.2977 (2) | 0.1727 (3) | 0.0516 (7) | |
| C7B | 0.3252 (3) | −0.23175 (19) | 0.1086 (2) | 0.0486 (6) | |
| C8B | 0.2957 (3) | −0.14973 (17) | 0.1757 (2) | 0.0408 (6) | |
| C9B | 0.3823 (3) | −0.13417 (17) | 0.3060 (2) | 0.0407 (6) | |
| H1B | 0.1190 (3) | −0.0650 (2) | 0.0650 (2) | 0.061 (8)* | |
| H3B | 0.3530 (3) | −0.01560 (17) | 0.4170 (2) | 0.044 (7)* | |
| H4B | 0.5600 (3) | −0.1942 (18) | 0.4500 (2) | 0.054 (7)* | |
| H5B | 0.6180 (3) | −0.3300 (2) | 0.3440 (2) | 0.065 (8)* | |
| H6B | 0.4700 (3) | −0.3575 (19) | 0.1310 (2) | 0.053 (7)* | |
| H7B | 0.2670 (3) | −0.2400 (18) | 0.0250 (2) | 0.049 (7)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0728 (5) | 0.0426 (4) | 0.0588 (4) | −0.0012 (4) | 0.0197 (4) | −0.0106 (3) |
| N3A | 0.0676 (15) | 0.0410 (13) | 0.0423 (12) | −0.0004 (12) | 0.0203 (11) | −0.0037 (10) |
| C2A | 0.0442 (14) | 0.0420 (14) | 0.0458 (14) | −0.0097 (12) | 0.0160 (11) | −0.0056 (12) |
| N21A | 0.0654 (15) | 0.0483 (14) | 0.0434 (13) | −0.0001 (12) | 0.0134 (11) | −0.0052 (11) |
| C4A | 0.084 (2) | 0.0550 (18) | 0.0494 (17) | −0.0019 (18) | 0.0182 (17) | −0.0002 (14) |
| C5A | 0.087 (3) | 0.0587 (19) | 0.0594 (18) | 0.0128 (19) | 0.0220 (17) | 0.0065 (15) |
| N1B | 0.0471 (12) | 0.0422 (12) | 0.0337 (11) | 0.0024 (10) | 0.0040 (10) | −0.0011 (9) |
| C2B | 0.0452 (13) | 0.0367 (13) | 0.0321 (11) | −0.0050 (11) | 0.0094 (10) | −0.0035 (10) |
| C21B | 0.0487 (14) | 0.0380 (13) | 0.0364 (13) | −0.0067 (11) | 0.0124 (11) | 0.0000 (10) |
| O21B | 0.0730 (12) | 0.0406 (10) | 0.0364 (9) | −0.0007 (9) | 0.0164 (8) | −0.0032 (8) |
| O22B | 0.0659 (12) | 0.0431 (10) | 0.0382 (9) | 0.0034 (9) | 0.0006 (8) | 0.0002 (7) |
| C3B | 0.0485 (15) | 0.0466 (14) | 0.0315 (13) | −0.0044 (12) | 0.0082 (11) | −0.0036 (11) |
| C4B | 0.0471 (15) | 0.0572 (17) | 0.0380 (14) | 0.0025 (14) | 0.0096 (12) | 0.0068 (13) |
| C5B | 0.0492 (15) | 0.0526 (16) | 0.0537 (15) | 0.0085 (14) | 0.0182 (13) | 0.0107 (13) |
| C6B | 0.0553 (16) | 0.0455 (15) | 0.0586 (16) | 0.0039 (14) | 0.0244 (13) | −0.0020 (13) |
| C7B | 0.0507 (16) | 0.0508 (16) | 0.0422 (14) | −0.0026 (13) | 0.0117 (12) | −0.0076 (13) |
| C8B | 0.0426 (14) | 0.0413 (14) | 0.0378 (12) | −0.0035 (12) | 0.0114 (10) | 0.0008 (11) |
| C9B | 0.0438 (14) | 0.0426 (14) | 0.0361 (12) | −0.0060 (12) | 0.0131 (11) | 0.0019 (10) |
Geometric parameters (Å, º) top
| S1A—C2A | 1.728 (3) | C21B—O21B | 1.259 (3) |
| S1A—C5A | 1.800 (3) | C21B—O22B | 1.262 (3) |
| N3A—C2A | 1.310 (3) | C3B—C9B | 1.413 (3) |
| N3A—C4A | 1.443 (4) | C4B—C5B | 1.369 (4) |
| C2A—N21A | 1.307 (3) | C4B—C9B | 1.401 (3) |
| C4A—C5A | 1.500 (4) | C5B—C6B | 1.398 (4) |
| N1B—C8B | 1.361 (3) | C6B—C7B | 1.370 (4) |
| N1B—C2B | 1.375 (3) | C7B—C8B | 1.390 (3) |
| C2B—C3B | 1.362 (3) | C8B—C9B | 1.415 (3) |
| C2B—C21B | 1.474 (3) | ||
| C2A—S1A—C5A | 91.38 (14) | O22B—C21B—C2B | 117.8 (2) |
| C2A—N3A—C4A | 116.7 (2) | C2B—C3B—C9B | 108.2 (2) |
| N21A—C2A—N3A | 123.7 (2) | C5B—C4B—C9B | 119.4 (2) |
| N21A—C2A—S1A | 122.30 (19) | C4B—C5B—C6B | 120.8 (2) |
| N3A—C2A—S1A | 114.00 (19) | C7B—C6B—C5B | 121.7 (3) |
| N3A—C4A—C5A | 108.6 (2) | C6B—C7B—C8B | 117.7 (2) |
| C4A—C5A—S1A | 108.1 (2) | N1B—C8B—C7B | 130.7 (2) |
| C8B—N1B—C2B | 109.52 (19) | N1B—C8B—C9B | 107.5 (2) |
| C3B—C2B—N1B | 108.5 (2) | C7B—C8B—C9B | 121.8 (2) |
| C3B—C2B—C21B | 130.0 (2) | C4B—C9B—C3B | 135.1 (2) |
| N1B—C2B—C21B | 121.30 (19) | C4B—C9B—C8B | 118.6 (2) |
| O21B—C21B—O22B | 124.4 (2) | C3B—C9B—C8B | 106.3 (2) |
| O21B—C21B—C2B | 117.7 (2) |
(5) '2-amino-2-thiazolinium N-methylpyrrole-2-carboxylate' top
Crystal data top
| C3H7N2S+·C6H6NO2− | F(000) = 960 |
| Mr = 227.28 | Dx = 1.329 Mg m−3 |
| Orthorhombic, Pbca | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ac 2ab | Cell parameters from 25 reflections |
| a = 11.9723 (8) Å | θ = 6–14° |
| b = 12.5938 (10) Å | µ = 0.27 mm−1 |
| c = 15.063 (2) Å | T = 298 K |
| V = 2271.1 (4) Å3 | Prism, colourless |
| Z = 8 | 0.50 × 0.40 × 0.18 mm |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | Rint = 0.021 |
| Radiation source: fine-focus sealed tube | θmax = 25.0°, θmin = 2.7° |
| Graphite monochromator | h = −6→14 |
| 2θ–ω scans | k = −3→14 |
| 2025 measured reflections | l = −9→17 |
| 1995 independent reflections | 3 standard reflections every 200 reflections |
| 1182 reflections with F > 4σ(F) | intensity decay: 1% |
Refinement top
| 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)] = 0.037 | H atoms treated by a mixture of independent and constrained refinement |
| wR(F2) = 0.117 | Calculated w = 1/[σ2(Fo2) + (0.0574P)2 + 0.562P] where P = (Fo2 + 2Fc2)/3 |
| S = 1.00 | (Δ/σ)max = 0.017 |
| 1995 reflections | Δρmax = 0.16 e Å−3 |
| 170 parameters | Δρmin = −0.16 e Å−3 |
| 0 restraints | Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
| Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0030 (10) |
Crystal data top
| C3H7N2S+·C6H6NO2− | V = 2271.1 (4) Å3 |
| Mr = 227.28 | Z = 8 |
| Orthorhombic, Pbca | Mo Kα radiation |
| a = 11.9723 (8) Å | µ = 0.27 mm−1 |
| b = 12.5938 (10) Å | T = 298 K |
| c = 15.063 (2) Å | 0.50 × 0.40 × 0.18 mm |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | Rint = 0.021 |
| 2025 measured reflections | 3 standard reflections every 200 reflections |
| 1995 independent reflections | intensity decay: 1% |
| 1182 reflections with F > 4σ(F) |
Refinement top
| R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
| wR(F2) = 0.117 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.00 | Δρmax = 0.16 e Å−3 |
| 1995 reflections | Δρmin = −0.16 e Å−3 |
| 170 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.10396 (7) | 0.57877 (6) | 0.13695 (6) | 0.0765 (3) | |
| C2A | 0.1789 (2) | 0.48668 (19) | 0.19779 (16) | 0.0487 (6) | |
| N21A | 0.1328 (2) | 0.40105 (19) | 0.23002 (17) | 0.0578 (7) | |
| N3A | 0.28489 (19) | 0.51026 (18) | 0.20692 (15) | 0.0544 (6) | |
| C4A | 0.3214 (3) | 0.6114 (2) | 0.1713 (2) | 0.0620 (8) | |
| C5A | 0.2256 (3) | 0.6608 (3) | 0.1213 (2) | 0.0766 (9) | |
| H51A | 0.2436 | 0.6656 | 0.0587 | 0.096* | |
| H52A | 0.2114 | 0.7318 | 0.1435 | 0.096* | |
| N1B | −0.11048 (18) | 0.15572 (17) | 0.03712 (14) | 0.0531 (6) | |
| C11B | −0.2006 (3) | 0.0842 (2) | 0.0623 (2) | 0.0782 (9) | |
| H11B | −0.2706 | 0.1127 | 0.0421 | 0.098* | |
| H12B | −0.2023 | 0.0770 | 0.1257 | 0.098* | |
| H13B | −0.1885 | 0.0160 | 0.0356 | 0.098* | |
| C2B | −0.0787 (2) | 0.2495 (2) | 0.07766 (16) | 0.0457 (6) | |
| C21B | −0.1394 (2) | 0.3023 (2) | 0.15045 (17) | 0.0476 (6) | |
| O21B | −0.09063 (14) | 0.37818 (15) | 0.18912 (13) | 0.0631 (6) | |
| O22B | −0.23550 (15) | 0.27121 (15) | 0.16994 (13) | 0.0683 (6) | |
| C3B | 0.0136 (2) | 0.2864 (2) | 0.03275 (18) | 0.0549 (7) | |
| C4B | 0.0384 (3) | 0.2150 (3) | −0.0356 (2) | 0.0637 (8) | |
| C5B | −0.0377 (3) | 0.1368 (3) | −0.03099 (19) | 0.0626 (8) | |
| H21A | 0.175 (3) | 0.354 (2) | 0.2663 (19) | 0.072 (9)* | |
| H22A | 0.066 (3) | 0.389 (2) | 0.219 (2) | 0.07 (1)* | |
| H3A | 0.326 (2) | 0.469 (2) | 0.2373 (18) | 0.054 (8)* | |
| H41A | 0.345 (2) | 0.657 (2) | 0.2217 (19) | 0.069 (9)* | |
| H42A | 0.385 (3) | 0.601 (3) | 0.137 (2) | 0.095 (12)* | |
| H3B | 0.048 (2) | 0.354 (2) | 0.0427 (17) | 0.059 (8)* | |
| H4B | 0.095 (2) | 0.223 (2) | −0.0776 (19) | 0.065 (8)* | |
| H5B | −0.051 (2) | 0.075 (2) | −0.0648 (17) | 0.06 (8)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0593 (5) | 0.0643 (5) | 0.1057 (7) | 0.0058 (4) | −0.0187 (4) | 0.0246 (4) |
| C2A | 0.0467 (14) | 0.0485 (15) | 0.0509 (16) | 0.0046 (12) | −0.0058 (12) | 0.0000 (12) |
| N21A | 0.0447 (14) | 0.0544 (14) | 0.0744 (18) | −0.0046 (12) | −0.0118 (13) | 0.0114 (12) |
| N3A | 0.0437 (13) | 0.0539 (14) | 0.0657 (14) | −0.0003 (11) | −0.0070 (11) | 0.0128 (12) |
| C4A | 0.0586 (18) | 0.0491 (17) | 0.078 (2) | −0.0053 (14) | 0.0021 (18) | 0.0058 (15) |
| C5A | 0.077 (2) | 0.0633 (18) | 0.089 (2) | −0.0075 (16) | −0.0113 (18) | 0.0217 (17) |
| N1B | 0.0560 (14) | 0.0488 (13) | 0.0544 (13) | 0.0071 (11) | −0.0003 (11) | −0.0051 (10) |
| C11B | 0.078 (2) | 0.0587 (18) | 0.098 (2) | −0.0090 (17) | 0.0070 (18) | −0.0142 (18) |
| C2B | 0.0447 (13) | 0.0490 (13) | 0.0433 (13) | 0.0084 (12) | −0.0036 (12) | −0.0009 (11) |
| C21B | 0.0373 (14) | 0.0533 (15) | 0.0521 (15) | 0.0057 (12) | −0.0024 (12) | −0.0032 (12) |
| O21B | 0.0404 (10) | 0.0730 (12) | 0.0759 (13) | −0.0040 (9) | 0.0042 (9) | −0.0295 (11) |
| O22B | 0.0431 (11) | 0.0790 (14) | 0.0826 (14) | −0.0088 (9) | 0.0122 (10) | −0.0284 (11) |
| C3B | 0.0531 (16) | 0.0586 (18) | 0.0529 (16) | 0.0026 (14) | 0.0041 (14) | 0.0005 (14) |
| C4B | 0.066 (2) | 0.072 (2) | 0.0536 (18) | 0.0111 (17) | 0.0120 (16) | −0.0007 (16) |
| C5B | 0.073 (2) | 0.0606 (18) | 0.0542 (17) | 0.0161 (17) | 0.0002 (16) | −0.0126 (15) |
Geometric parameters (Å, º) top
| C2A—N21A | 1.305 (3) | N1B—C11B | 1.456 (3) |
| C2A—N3A | 1.311 (3) | C2B—C3B | 1.377 (4) |
| C2A—S1A | 1.729 (2) | C2B—C21B | 1.474 (3) |
| N3A—C4A | 1.449 (3) | C21B—O21B | 1.263 (3) |
| C4A—C5A | 1.506 (4) | C21B—O22B | 1.250 (3) |
| C5A—S1A | 1.801 (3) | C3B—C4B | 1.399 (4) |
| N1B—C5B | 1.367 (3) | C4B—C5B | 1.343 (4) |
| N1B—C2B | 1.383 (3) | ||
| N21A—C2A—N3A | 123.9 (2) | C3B—C2B—N1B | 107.0 (2) |
| N21A—C2A—S1A | 122.1 (2) | C3B—C2B—C21B | 127.6 (3) |
| C2A—N3A—C4A | 116.9 (2) | N1B—C2B—C21B | 125.3 (2) |
| N3A—C4A—C5A | 108.6 (2) | O21B—C21B—O22B | 123.7 (2) |
| C4A—C5A—S1A | 108.3 (2) | O21B—C21B—C2B | 117.1 (2) |
| C2A—S1A—C5A | 91.96 (13) | O22B—C21B—C2B | 119.2 (2) |
| C5B—N1B—C2B | 107.7 (2) | C2B—C3B—C4B | 108.4 (3) |
| C5B—N1B—C11B | 124.1 (2) | C5B—C4B—C3B | 106.8 (3) |
| C2B—N1B—C11B | 128.1 (2) | C4B—C5B—N1B | 110.1 (3) |
(7) '2-Aminobenzothiazolium indole-2-carboxylate' top
Crystal data top
| C7H7N2S+·C9H6NO2− | F(000) = 648 |
| Mr = 311.35 | Dx = 1.452 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 10.182 (4) Å | θ = 6–14° |
| b = 11.923 (2) Å | µ = 0.24 mm−1 |
| c = 12.284 (6) Å | T = 298 K |
| β = 107.23 (2)° | Prism, colourless |
| V = 1424.4 (9) Å3 | 0.60 × 0.20 × 0.18 mm |
| Z = 4 |
Data collection top
| Enraf Nonius CAD-4 diffractometer | 1504 reflections with F > 4σ(F) |
| Radiation source: fine-focus sealed tube | Rint = 0.076 |
| Graphite monochromator | θmax = 24.9°, θmin = 2.1° |
| 2θ–ω scans | h = 0→12 |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | k = 0→14 |
| Tmin = 0.899, Tmax = 0.998 | l = −14→13 |
| 2641 measured reflections | 3 standard reflections every 200 reflections |
| 2494 independent reflections | intensity decay: 1% |
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)] = 0.051 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.162 | All H-atom parameters refined |
| S = 0.94 | Calculated w = 1/[σ2(Fo2) + (0.1084P)2] where P = (Fo2 + 2Fc2)/3 |
| 2494 reflections | (Δ/σ)max < 0.002 |
| 251 parameters | Δρmax = 0.27 e Å−3 |
| 0 restraints | Δρmin = −0.37 e Å−3 |
Crystal data top
| C7H7N2S+·C9H6NO2− | V = 1424.4 (9) Å3 |
| Mr = 311.35 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 10.182 (4) Å | µ = 0.24 mm−1 |
| b = 11.923 (2) Å | T = 298 K |
| c = 12.284 (6) Å | 0.60 × 0.20 × 0.18 mm |
| β = 107.23 (2)° |
Data collection top
| Enraf Nonius CAD-4 diffractometer | 1504 reflections with F > 4σ(F) |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | Rint = 0.076 |
| Tmin = 0.899, Tmax = 0.998 | 3 standard reflections every 200 reflections |
| 2641 measured reflections | intensity decay: 1% |
| 2494 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.051 | 0 restraints |
| wR(F2) = 0.162 | All H-atom parameters refined |
| S = 0.94 | Δρmax = 0.27 e Å−3 |
| 2494 reflections | Δρmin = −0.37 e Å−3 |
| 251 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.5868 (1) | 0.0512 (1) | 0.7713 (1) | 0.050 (1) | |
| C2A | 0.4924 (4) | 0.1591 (3) | 0.6908 (3) | 0.042 (1) | |
| N21A | 0.4031 (4) | 0.2180 (3) | 0.7244 (3) | 0.055 (1) | |
| N3A | 0.5209 (3) | 0.1743 (3) | 0.5927 (2) | 0.041 (1) | |
| C4A | 0.6687 (4) | 0.0969 (3) | 0.4822 (3) | 0.048 (1) | |
| C5A | 0.7659 (4) | 0.0178 (4) | 0.4807 (4) | 0.059 (1) | |
| C6A | 0.8130 (5) | −0.0576 (4) | 0.5696 (4) | 0.062 (1) | |
| C7A | 0.7618 (4) | −0.0551 (3) | 0.6628 (4) | 0.054 (1) | |
| C8A | 0.6655 (4) | 0.0256 (3) | 0.6648 (3) | 0.043 (1) | |
| C9A | 0.6186 (3) | 0.1007 (3) | 0.5747 (3) | 0.039 (1) | |
| H21A | 0.3562 (4) | 0.2721 (4) | 0.6782 (4) | 0.068 (13)* | |
| H22A | 0.3892 (4) | 0.2011 (4) | 0.7879 (3) | 0.054 (11)* | |
| H3A | 0.477 (4) | 0.221 (4) | 0.549 (4) | 0.061 (13)* | |
| H4A | 0.633 (4) | 0.145 (3) | 0.426 (3) | 0.049 (10)* | |
| H5A | 0.801 (4) | 0.015 (3) | 0.426 (3) | 0.059 (12)* | |
| H6A | 0.882 (4) | −0.118 (3) | 0.568 (3) | 0.063 (11)* | |
| H7A | 0.799 (4) | −0.098 (3) | 0.7280 (3) | 0.055 (11)* | |
| N1B | 0.8511 (3) | 0.0547 (2) | 1.0434 (3) | 0.046 (1) | |
| C2B | 0.7533 (3) | −0.0009 (3) | 1.0797 (3) | 0.040 (1) | |
| C21B | 0.6908 (3) | −0.1046 (3) | 1.0194 (3) | 0.041 (1) | |
| O21B | 0.6067 (3) | −0.1589 (2) | 1.0558 (2) | 0.050 (1) | |
| O22B | 0.7264 (3) | −0.1292 (2) | 0.9327 (2) | 0.055 (1) | |
| C3B | 0.7375 (4) | 0.0523 (3) | 1.1721 (3) | 0.041 (1) | |
| C4B | 0.8588 (4) | 0.2304 (3) | 1.2797 (3) | 0.051 (1) | |
| C5B | 0.9547 (4) | 0.3096 (3) | 1.2754 (4) | 0.056 (1) | |
| C6B | 1.0198 (4) | 0.3093 (4) | 1.1912 (4) | 0.058 (1) | |
| C7B | 0.9939 (4) | 0.2284 (3) | 1.1090 (3) | 0.053 (1) | |
| C8B | 0.8968 (3) | 0.1465 (3) | 1.1116 (3) | 0.041 (1) | |
| C9B | 0.8271 (3) | 0.1468 (3) | 1.1954 (3) | 0.040 (1) | |
| H1B | 0.872 (4) | 0.039 (3) | 0.984 (3) | 0.058 (12)* | |
| H3B | 0.678 (4) | 0.033 (3) | 1.209 (3) | 0.060 (12)* | |
| H4B | 0.813 (4) | 0.233 (3) | 1.342 (3) | 0.053 (10)* | |
| H5B | 0.975 (4) | 0.361 (3) | 1.327 (3) | 0.058 (12)* | |
| H6B | 1.086 (4) | 0.369 (3) | 1.191 (3) | 0.054 (10)* | |
| H7B | 1.044 (4) | 0.226 (3) | 1.056 (3) | 0.065 (12)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.057 (1) | 0.052 (1) | 0.040 (1) | 0.001 (1) | 0.013 (1) | 0.014 (1) |
| C2A | 0.048 (2) | 0.042 (2) | 0.034 (2) | −0.005 (2) | 0.010 (2) | 0.008 (2) |
| N21A | 0.072 (2) | 0.057 (2) | 0.044 (2) | 0.012 (2) | 0.028 (2) | 0.012 (2) |
| N3A | 0.048 (2) | 0.040 (2) | 0.035 (2) | 0.002 (1) | 0.011 (1) | 0.006 (1) |
| C4A | 0.057 (2) | 0.047 (2) | 0.040 (2) | 0.000 (2) | 0.015 (2) | 0.004 (2) |
| C5A | 0.065 (3) | 0.061 (3) | 0.057 (3) | 0.003 (2) | 0.029 (2) | −0.005 (2) |
| C6A | 0.062 (3) | 0.047 (2) | 0.080 (3) | 0.009 (2) | 0.023 (2) | −0.004 (2) |
| C7A | 0.054 (2) | 0.046 (2) | 0.057 (2) | 0.005 (2) | 0.009 (2) | 0.011 (2) |
| C8A | 0.048 (2) | 0.037 (2) | 0.041 (2) | −0.005 (2) | 0.010 (2) | 0.003 (2) |
| C9A | 0.043 (2) | 0.034 (2) | 0.039 (2) | −0.002 (2) | 0.008 (2) | 0.001 (2) |
| N1B | 0.057 (2) | 0.044 (2) | 0.040 (2) | −0.004 (2) | 0.019 (1) | −0.001 (1) |
| C2B | 0.043 (2) | 0.035 (2) | 0.039 (2) | −0.003 (2) | 0.010 (2) | 0.004 (2) |
| C21B | 0.051 (2) | 0.037 (2) | 0.033 (2) | 0.001 (2) | 0.010 (2) | 0.003 (2) |
| O21B | 0.068 (2) | 0.043 (1) | 0.042 (1) | −0.013 (1) | 0.021 (1) | −0.001 (1) |
| O22B | 0.077 (2) | 0.050 (2) | 0.047 (2) | −0.008 (1) | 0.032 (1) | −0.009 (1) |
| C3B | 0.045 (2) | 0.041 (2) | 0.041 (2) | −0.002 (2) | 0.019 (2) | 0.001 (2) |
| C4B | 0.059 (2) | 0.045 (2) | 0.049 (2) | −0.001 (2) | 0.016 (2) | −0.008 (2) |
| C5B | 0.065 (3) | 0.042 (2) | 0.057 (3) | 0.001 (2) | 0.012 (2) | −0.010 (2) |
| C6B | 0.056 (3) | 0.049 (2) | 0.064 (3) | −0.015 (2) | 0.010 (2) | 0.004 (2) |
| C7B | 0.053 (2) | 0.056 (2) | 0.052 (2) | −0.006 (2) | 0.019 (2) | 0.010 (2) |
| C8B | 0.045 (2) | 0.038 (2) | 0.039 (2) | 0.000 (2) | 0.010 (2) | 0.006 (2) |
| C9B | 0.043 (2) | 0.037 (2) | 0.040 (2) | 0.001 (2) | 0.013 (2) | 0.000 (2) |
Geometric parameters (Å, º) top
| S1A—C2A | 1.730 (3) | N1B—C2B | 1.376 (4) |
| S1A—C8A | 1.751 (4) | C2B—C3B | 1.351 (5) |
| C2A—N21A | 1.308 (5) | C2B—C21B | 1.484 (5) |
| C2A—N3A | 1.334 (4) | C21B—O22B | 1.257 (4) |
| N3A—C9A | 1.393 (4) | C21B—O21B | 1.257 (4) |
| C4A—C5A | 1.371 (6) | C3B—C9B | 1.424 (5) |
| C4A—C9A | 1.377 (5) | C4B—C5B | 1.371 (6) |
| C5A—C6A | 1.385 (6) | C4B—C9B | 1.404 (5) |
| C6A—C7A | 1.392 (6) | C5B—C6B | 1.384 (6) |
| C7A—C8A | 1.379 (5) | C6B—C7B | 1.364 (6) |
| C8A—C9A | 1.394 (5) | C7B—C8B | 1.397 (5) |
| N1B—C8B | 1.373 (4) | C8B—C9B | 1.413 (5) |
| C2A—S1A—C8A | 90.17 (17) | C3B—C2B—C21B | 132.1 (3) |
| N21A—C2A—N3A | 124.7 (3) | N1B—C2B—C21B | 118.9 (3) |
| N21A—C2A—S1A | 122.7 (3) | O22B—C21B—O21B | 125.4 (3) |
| N3A—C2A—S1A | 112.6 (3) | O22B—C21B—C2B | 115.4 (3) |
| C2A—N3A—C9A | 114.5 (3) | O21B—C21B—C2B | 119.2 (3) |
| C5A—C4A—C9A | 118.6 (4) | C2B—C3B—C9B | 108.2 (3) |
| C4A—C5A—C6A | 121.3 (4) | C5B—C4B—C9B | 118.1 (4) |
| C5A—C6A—C7A | 120.5 (4) | C4B—C5B—C6B | 122.1 (4) |
| C8A—C7A—C6A | 118.1 (4) | C7B—C6B—C5B | 121.6 (4) |
| C7A—C8A—C9A | 120.8 (3) | C6B—C7B—C8B | 117.4 (4) |
| C7A—C8A—S1A | 128.3 (3) | N1B—C8B—C7B | 131.1 (3) |
| C9A—C8A—S1A | 110.9 (3) | N1B—C8B—C9B | 107.1 (3) |
| C4A—C9A—C8A | 120.7 (3) | C7B—C8B—C9B | 121.7 (3) |
| C4A—C9A—N3A | 127.5 (3) | C4B—C9B—C8B | 119.0 (3) |
| C8A—C9A—N3A | 111.8 (3) | C4B—C9B—C3B | 134.7 (3) |
| C8B—N1B—C2B | 109.5 (3) | C8B—C9B—C3B | 106.3 (3) |
| C3B—C2B—N1B | 108.9 (3) |
(8) '2-aminobenzothiazolium N-methylpyrrole-2-carboxylate' top
Crystal data top
| C7H7N2S+·C6H6NO2− | F(000) = 576 |
| Mr = 275.32 | Dx = 1.398 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 5.5561 (9) Å | θ = 6–14° |
| b = 19.701 (3) Å | µ = 0.25 mm−1 |
| c = 12.143 (2) Å | T = 298 K |
| β = 100.263 (8)° | Prism, colourless |
| V = 1307.9 (4) Å3 | 0.50 × 0.30 × 0.10 mm |
| Z = 4 |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1440 reflections with F > 4σ(F) |
| Radiation source: fine-focus sealed tube | Rint = 0.036 |
| Graphite monochromator | θmax = 25.0°, θmin = 2.0° |
| 2θ–ω scans | h = 0→6 |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | k = 0→23 |
| Tmin = 0.870, Tmax = 0.998 | l = −14→14 |
| 2552 measured reflections | 3 standard reflections every 200 reflections |
| 2302 independent reflections | intensity decay: 1% |
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)] = 0.038 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.108 | All H-atom parameters refined |
| S = 0.99 | Calculated w = 1/[σ2(Fo2) + (0.0544P)2 + 0.2231P] where P = (Fo2 + 2Fc2)/3 |
| 2302 reflections | (Δ/σ)max < 0.002 |
| 224 parameters | Δρmax = 0.22 e Å−3 |
| 0 restraints | Δρmin = −0.27 e Å−3 |
Crystal data top
| C7H7N2S+·C6H6NO2− | V = 1307.9 (4) Å3 |
| Mr = 275.32 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 5.5561 (9) Å | µ = 0.25 mm−1 |
| b = 19.701 (3) Å | T = 298 K |
| c = 12.143 (2) Å | 0.50 × 0.30 × 0.10 mm |
| β = 100.263 (8)° |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1440 reflections with F > 4σ(F) |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | Rint = 0.036 |
| Tmin = 0.870, Tmax = 0.998 | 3 standard reflections every 200 reflections |
| 2552 measured reflections | intensity decay: 1% |
| 2302 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.038 | 0 restraints |
| wR(F2) = 0.108 | All H-atom parameters refined |
| S = 0.99 | Δρmax = 0.22 e Å−3 |
| 2302 reflections | Δρmin = −0.27 e Å−3 |
| 224 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | −0.00630 (14) | 0.33873 (4) | 0.48861 (6) | 0.0386 (2) | |
| C2A | 0.2038 (5) | 0.29032 (14) | 0.4325 (2) | 0.0349 (6) | |
| N21A | 0.3906 (5) | 0.26062 (14) | 0.4945 (2) | 0.0430 (6) | |
| N3A | 0.155 (4) | 0.2871 (1) | 0.3217 (2) | 0.0364 (6) | |
| C4A | −0.1389 (6) | 0.33343 (16) | 0.1601 (2) | 0.0437 (7) | |
| C5A | −0.3439 (6) | 0.37330 (16) | 0.1296 (3) | 0.0475 (8) | |
| C6A | −0.4606 (6) | 0.40344 (16) | 0.2091 (3) | 0.0465 (8) | |
| C7A | −0.3724 (5) | 0.39458 (15) | 0.3216 (3) | 0.0410 (7) | |
| C8A | −0.1644 (5) | 0.35563 (13) | 0.3535 (2) | 0.0330 (6) | |
| C9A | −0.0507 (5) | 0.32445 (13) | 0.2729 (2) | 0.0347 (6) | |
| N1B | 0.9112 (4) | 0.08034 (12) | 0.27295 (19) | 0.0435 (6) | |
| C11B | 1.0778 (8) | 0.0949 (3) | 0.3773 (3) | 0.0659 (11) | |
| C2B | 0.6982 (5) | 0.11363 (13) | 0.2273 (2) | 0.0340 (6) | |
| C21B | 0.5973 (5) | 0.17185 (14) | 0.2800 (2) | 0.0351 (6) | |
| O21B | 0.4199 (4) | 0.20326 (10) | 0.21895 (15) | 0.0434 (5) | |
| O22B | 0.6802 (4) | 0.18681 (11) | 0.37872 (15) | 0.0509 (6) | |
| C3B | 0.6062 (6) | 0.08196 (14) | 0.1284 (2) | 0.0382 (7) | |
| C4B | 0.7644 (6) | 0.02900 (16) | 0.1129 (3) | 0.0465 (8) | |
| C5B | 0.9498 (7) | 0.02926 (16) | 0.2023 (3) | 0.0500 (8) | |
| H21A | 0.492 (6) | 0.2372 (16) | 0.462 (3) | 0.052 (9)* | |
| H22A | 0.422 (5) | 0.2713 (15) | 0.566 (3) | 0.050 (9)* | |
| H3A | 0.2370 (6) | 0.2621 (16) | 0.284 (3) | 0.060 (10)* | |
| H4A | −0.054 (6) | 0.3157 (15) | 0.106 (3) | 0.056 (9)* | |
| H5A | −0.404 (5) | 0.3814 (14) | 0.053 (2) | 0.049 (9)* | |
| H6A | −0.605 (6) | 0.4294 (16) | 0.184 (2) | 0.052 (9)* | |
| H7A | −0.448 (5) | 0.4138 (13) | 0.376 (2) | 0.036 (7)* | |
| H11B | 1.098 (9) | 0.143 (3) | 0.394 (4) | 0.134 (19)* | |
| H12B | 1.223 (8) | 0.070 (2) | 0.377 (3) | 0.104 (15)* | |
| H13B | 0.998 (8) | 0.080 (2) | 0.439 (3) | 0.095 (15)* | |
| H3B | 0.457 (5) | 0.0933 (13) | 0.084 (2) | 0.041 (8)* | |
| H4B | 0.751 (6) | −0.0011 (16) | 0.051 (3) | 0.055 (9)* | |
| H5B | 1.100 (6) | 0.0017 (15) | 0.218 (2) | 0.048 (8)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0387 (4) | 0.0454 (4) | 0.0329 (4) | 0.0059 (4) | 0.0102 (3) | −0.0046 (3) |
| C2A | 0.0362 (16) | 0.0377 (15) | 0.0319 (14) | −0.0011 (13) | 0.0094 (13) | −0.0017 (12) |
| N21A | 0.0427 (15) | 0.0545 (16) | 0.0315 (13) | 0.0137 (13) | 0.0055 (12) | −0.0052 (12) |
| N3A | 0.0391 (14) | 0.0398 (14) | 0.0320 (12) | 0.0053 (11) | 0.0105 (11) | −0.0043 (10) |
| C4A | 0.051 (2) | 0.0472 (18) | 0.0324 (15) | 0.0009 (16) | 0.0073 (14) | −0.0032 (14) |
| C5A | 0.050 (2) | 0.0522 (19) | 0.0354 (17) | −0.0012 (16) | −0.0063 (15) | 0.0010 (15) |
| C6A | 0.0363 (18) | 0.0449 (18) | 0.0551 (19) | 0.0021 (15) | −0.0007 (15) | 0.0021 (15) |
| C7A | 0.0365 (17) | 0.0422 (17) | 0.0453 (18) | −0.0002 (14) | 0.0098 (14) | −0.0040 (14) |
| C8A | 0.0343 (16) | 0.0309 (14) | 0.0339 (14) | −0.0053 (12) | 0.0065 (12) | −0.0017 (11) |
| C9A | 0.0332 (16) | 0.0317 (15) | 0.0392 (15) | −0.0036 (12) | 0.0062 (12) | −0.0010 (11) |
| N1B | 0.0379 (14) | 0.0440 (14) | 0.0478 (15) | 0.0064 (12) | 0.0051 (11) | −0.0076 (11) |
| C11B | 0.053 (2) | 0.075 (3) | 0.062 (2) | 0.019 (2) | −0.012 (2) | −0.012 (2) |
| C2B | 0.0334 (16) | 0.0327 (14) | 0.0369 (15) | 0.0017 (12) | 0.0088 (12) | 0.0020 (12) |
| C21B | 0.0364 (16) | 0.0396 (15) | 0.0310 (14) | 0.0003 (13) | 0.0103 (12) | 0.0017 (12) |
| O21B | 0.0503 (13) | 0.0484 (12) | 0.0323 (10) | 0.0168 (10) | 0.0094 (9) | 0.0009 (9) |
| O22B | 0.0579 (14) | 0.0603 (14) | 0.0332 (11) | 0.0167 (11) | 0.0040 (10) | −0.0079 (10) |
| C3B | 0.0379 (17) | 0.0396 (16) | 0.0369 (16) | −0.0015 (14) | 0.0064 (14) | −0.0011 (13) |
| C4B | 0.053 (2) | 0.0367 (16) | 0.0512 (19) | −0.0018 (15) | 0.0138 (16) | −0.0117 (15) |
| C5B | 0.049 (2) | 0.0389 (17) | 0.064 (2) | 0.0094 (16) | 0.0158 (17) | −0.0031 (15) |
Geometric parameters (Å, º) top
| S1A—C2A | 1.738 (3) | C8A—C9A | 1.398 (4) |
| S1A—C8A | 1.750 (3) | N1B—C5B | 1.364 (4) |
| C2A—N21A | 1.307 (4) | N1B—C2B | 1.380 (3) |
| C2A—N3A | 1.326 (3) | N1B—C11B | 1.458 (4) |
| N3A—C9A | 1.399 (3) | C2B—C3B | 1.369 (4) |
| C4A—C5A | 1.379 (4) | C2B—C21B | 1.472 (4) |
| C4A—C9A | 1.381 (4) | C21B—O22B | 1.240 (3) |
| C5A—C6A | 1.389 (4) | C21B—O21B | 1.282 (3) |
| C6A—C7A | 1.378 (4) | C3B—C4B | 1.398 (4) |
| C7A—C8A | 1.383 (4) | C4B—C5B | 1.357 (4) |
| C2A—S1A—C8A | 89.82 (13) | C8A—C9A—N3A | 111.8 (2) |
| N21A—C2A—N3A | 124.1 (3) | C5B—N1B—C2B | 108.5 (2) |
| N21A—C2A—S1A | 122.7 (2) | C5B—N1B—C11B | 123.0 (3) |
| N3A—C2A—S1A | 113.2 (2) | C2B—N1B—C11B | 128.4 (3) |
| C2A—N3A—C9A | 114.1 (2) | C3B—C2B—N1B | 107.2 (2) |
| C5A—C4A—C9A | 118.0 (3) | C3B—C2B—C21B | 128.7 (3) |
| C4A—C5A—C6A | 121.5 (3) | N1B—C2B—C21B | 124.1 (2) |
| C7A—C6A—C5A | 120.5 (3) | O22B—C21B—O21B | 124.0 (2) |
| C8A—C7A—C6A | 118.6 (3) | O22B—C21B—C2B | 120.1 (2) |
| C7A—C8A—C9A | 120.5 (2) | O21B—C21B—C2B | 115.9 (2) |
| C7A—C8A—S1A | 128.5 (2) | C2B—C3B—C4B | 108.2 (3) |
| C9A—C8A—S1A | 111.0 (2) | C5B—C4B—C3B | 107.2 (3) |
| C4A—C9A—C8A | 120.8 (3) | C4B—C5B—N1B | 108.9 (3) |
| C4A—C9A—N3A | 127.3 (3) |
(9) '2-aminobenzothiazolium thiophene-2-carboxylate' top
Crystal data top
| C7H7N2S+·C5H3O2S− | F(000) = 576 |
| Mr = 278.34 | Dx = 1.557 Mg m−3 |
| Monoclinic, P21/c | Mo Kα radiation, λ = 0.71073 Å |
| Hall symbol: -P 2ybc | Cell parameters from 25 reflections |
| a = 9.162 (2) Å | θ = 6–14° |
| b = 11.121 (3) Å | µ = 0.44 mm−1 |
| c = 12.033 (2) Å | T = 293 K |
| β = 104.388 (9)° | Prism, colourless |
| V = 1187.6 (5) Å3 | 0.48 × 0.24 × 0.20 mm |
| Z = 4 |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1538 reflections with F > 4σ(F) |
| Radiation source: fine-focus sealed tube | Rint = 0.023 |
| Graphite monochromator | θmax = 26.2°, θmin = 2.3° |
| 2θ–ω scans | h = 0→11 |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | k = 0→13 |
| Tmin = 0.768, Tmax = 0.915 | l = −14→13 |
| 2334 measured reflections | 3 standard reflections every 200 reflections |
| 2197 independent reflections | intensity decay: 1% |
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)] = 0.049 | Hydrogen site location: inferred from neighbouring sites |
| wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Calculated w = 1/[σ2(Fo2) + (0.0791P)2 + 1.2898P] where P = (Fo2 + 2Fc2)/3 |
| 2197 reflections | (Δ/σ)max = 0.001 |
| 191 parameters | Δρmax = 0.50 e Å−3 |
| 0 restraints | Δρmin = −0.53 e Å−3 |
Crystal data top
| C7H7N2S+·C5H3O2S− | V = 1187.6 (5) Å3 |
| Mr = 278.34 | Z = 4 |
| Monoclinic, P21/c | Mo Kα radiation |
| a = 9.162 (2) Å | µ = 0.44 mm−1 |
| b = 11.121 (3) Å | T = 293 K |
| c = 12.033 (2) Å | 0.48 × 0.24 × 0.20 mm |
| β = 104.388 (9)° |
Data collection top
| Enraf-Nonius CAD-4 diffractometer | 1538 reflections with F > 4σ(F) |
| Absorption correction: ψ scan Xtal 3.2 (Hall et al., 1992) | Rint = 0.023 |
| Tmin = 0.768, Tmax = 0.915 | 3 standard reflections every 200 reflections |
| 2334 measured reflections | intensity decay: 1% |
| 2197 independent reflections |
Refinement top
| R[F2 > 2σ(F2)] = 0.049 | 0 restraints |
| wR(F2) = 0.156 | H atoms treated by a mixture of independent and constrained refinement |
| S = 1.05 | Δρmax = 0.50 e Å−3 |
| 2197 reflections | Δρmin = −0.53 e Å−3 |
| 191 parameters |
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
| x | y | z | Uiso*/Ueq | ||
| S1A | 0.06852 (10) | 0.06403 (9) | 0.75046 (8) | 0.0429 (3) | |
| C2A | −0.0521 (4) | 0.1630 (3) | 0.7869 (3) | 0.0369 (8) | |
| N21A | −0.1589 (4) | 0.2112 (3) | 0.7121 (3) | 0.0475 (9) | |
| N3A | −0.0232 (3) | 0.1846 (3) | 0.8991 (2) | 0.0380 (7) | |
| C4A | 0.1475 (4) | 0.1258 (4) | 1.0809 (3) | 0.0439 (9) | |
| C5A | 0.2660 (5) | 0.0557 (4) | 1.1290 (3) | 0.0502 (10) | |
| C6A | 0.3297 (5) | −0.0150 (4) | 1.0609 (4) | 0.0506 (10) | |
| C7A | 0.2780 (4) | −0.0179 (4) | 0.9433 (3) | 0.0450 (9) | |
| C8A | 0.1591 (4) | 0.0512 (3) | 0.8954 (3) | 0.0370 (8) | |
| C9A | 0.0939 (4) | 0.1223 (3) | 0.9636 (3) | 0.0358 (8) | |
| S1B | −0.43616 (13) | 0.60626 (11) | 0.84787 (12) | 0.0681 (4) | |
| C2B | −0.3181 (4) | 0.5215 (3) | 0.9447 (3) | 0.0403 (8) | |
| C21B | −0.2615 (4) | 0.4083 (3) | 0.9074 (3) | 0.0409 (9) | |
| O21B | −0.1768 (3) | 0.3465 (2) | 0.9826 (2) | 0.0489 (7) | |
| O22B | −0.3012 (3) | 0.3811 (3) | 0.8037 (2) | 0.0558 (8) | |
| C3B | −0.2836 (5) | 0.5744 (3) | 1.0561 (3) | 0.0420 (9) | |
| H3B | −0.2160 | 0.5437 | 1.1207 | 0.053* | |
| C4B | −0.3679 (6) | 0.6800 (4) | 1.0526 (4) | 0.0639 (12) | |
| H4B | −0.3656 | 0.7271 | 1.1169 | 0.080* | |
| C5B | −0.4508 (5) | 0.7060 (4) | 0.9494 (5) | 0.0653 (13) | |
| H5B | −0.5121 | 0.7737 | 0.9341 | 0.082* | |
| H21A | −0.215 (5) | 0.256 (4) | 0.738 (4) | 0.060 (14)* | |
| H22A | −0.173 (4) | 0.194 (4) | 0.645 (4) | 0.048 (12)* | |
| H3A | −0.0800 (6) | 0.237 (5) | 0.929 (4) | 0.077 (16)* | |
| H4A | 0.097 (4) | 0.182 (3) | 1.124 (3) | 0.045 (10)* | |
| H5A | 0.309 (5) | 0.057 (4) | 1.215 (4) | 0.053 (11)* | |
| H6A | 0.399 (5) | −0.060 (4) | 1.090 (4) | 0.050 (12)* | |
| H7A | 0.323 (4) | −0.057 (4) | 0.894 (3) | 0.048 (11)* |
Atomic displacement parameters (Å2) top
| U11 | U22 | U33 | U12 | U13 | U23 | |
| S1A | 0.0452 (5) | 0.0530 (6) | 0.0315 (5) | 0.0079 (4) | 0.0113 (4) | −0.0066 (4) |
| C2A | 0.0421 (19) | 0.038 (2) | 0.0319 (18) | 0.0005 (15) | 0.0108 (15) | −0.0043 (15) |
| N21A | 0.0512 (19) | 0.060 (2) | 0.0308 (18) | 0.0145 (16) | 0.0096 (15) | −0.0038 (16) |
| N3A | 0.0407 (16) | 0.0434 (17) | 0.0310 (15) | 0.0034 (14) | 0.0111 (12) | −0.0038 (13) |
| C4A | 0.046 (2) | 0.053 (2) | 0.0334 (19) | −0.0007 (18) | 0.0126 (16) | −0.0049 (17) |
| C5A | 0.053 (2) | 0.062 (3) | 0.033 (2) | 0.000 (2) | 0.0056 (17) | 0.0010 (19) |
| C6A | 0.047 (2) | 0.054 (3) | 0.047 (2) | 0.009 (2) | 0.0042 (18) | 0.002 (2) |
| C7A | 0.044 (2) | 0.047 (2) | 0.045 (2) | 0.0045 (17) | 0.0114 (17) | −0.0092 (18) |
| C8A | 0.0389 (18) | 0.041 (2) | 0.0317 (18) | −0.0024 (15) | 0.0097 (14) | −0.0032 (15) |
| C9A | 0.0382 (17) | 0.0377 (19) | 0.0332 (18) | 0.0001 (15) | 0.0119 (14) | −0.0010 (15) |
| S1B | 0.0608 (7) | 0.0600 (8) | 0.0747 (8) | 0.0099 (6) | 0.0000 (6) | 0.0015 (6) |
| C2B | 0.0406 (19) | 0.040 (2) | 0.044 (2) | 0.0034 (15) | 0.0167 (16) | 0.0082 (16) |
| C21B | 0.048 (2) | 0.044 (2) | 0.036 (2) | 0.0045 (16) | 0.0200 (16) | 0.0036 (16) |
| O21B | 0.0693 (18) | 0.0643 (19) | 0.0327 (15) | 0.0206 (15) | 0.0107 (13) | −0.0020 (13) |
| O22B | 0.0638 (16) | 0.0535 (16) | 0.0316 (13) | 0.0207 (14) | 0.0160 (12) | 0.0060 (12) |
| C3B | 0.068 (2) | 0.0287 (18) | 0.0353 (19) | 0.0117 (17) | 0.0248 (17) | 0.0028 (15) |
| C4B | 0.075 (3) | 0.050 (3) | 0.073 (3) | −0.001 (2) | 0.030 (3) | −0.012 (2) |
| C5B | 0.052 (2) | 0.037 (2) | 0.108 (4) | 0.0036 (19) | 0.024 (3) | 0.000 (2) |
Geometric parameters (Å, º) top
| S1A—C2A | 1.692 (3) | C8A—C9A | 1.378 (5) |
| S1A—C8A | 1.741 (3) | S1B—C2B | 1.670 (4) |
| C2A—N21A | 1.272 (5) | S1B—C5B | 1.680 (5) |
| C2A—N3A | 1.332 (4) | C2B—C3B | 1.425 (5) |
| N3A—C9A | 1.349 (4) | C2B—C21B | 1.474 (5) |
| C4A—C5A | 1.345 (6) | C21B—O22B | 1.243 (4) |
| C4A—C9A | 1.376 (5) | C21B—O21B | 1.247 (4) |
| C5A—C6A | 1.367 (6) | C3B—C4B | 1.400 (6) |
| C6A—C7A | 1.377 (6) | C4B—C5B | 1.317 (7) |
| C7A—C8A | 1.341 (5) | ||
| C2A—S1A—C8A | 88.47 (17) | N3A—C9A—C8A | 110.7 (3) |
| N21A—C2A—N3A | 124.4 (3) | C4A—C9A—C8A | 122.0 (3) |
| N21A—C2A—S1A | 121.9 (3) | C2B—S1B—C5B | 91.1 (2) |
| N3A—C2A—S1A | 113.7 (3) | C3B—C2B—C21B | 128.8 (3) |
| C2A—N3A—C9A | 114.8 (3) | C3B—C2B—S1B | 112.2 (3) |
| C5A—C4A—C9A | 118.0 (4) | C21B—C2B—S1B | 119.0 (3) |
| C4A—C5A—C6A | 119.7 (4) | O22B—C21B—O21B | 124.6 (3) |
| C5A—C6A—C7A | 122.8 (4) | O21B—C21B—C2B | 117.0 (3) |
| C8A—C7A—C6A | 117.6 (4) | O22B—C21B—C2B | 118.4 (3) |
| C7A—C8A—C9A | 120.0 (3) | C4B—C3B—C2B | 109.0 (4) |
| C7A—C8A—S1A | 127.7 (3) | C5B—C4B—C3B | 113.4 (4) |
| C9A—C8A—S1A | 112.3 (3) | C4B—C5B—S1B | 114.2 (4) |
| N3A—C9A—C4A | 127.3 (3) |
Experimental details
| (4) | (5) | (7) | (8) | |
| Crystal data | ||||
| Chemical formula | C3H7N2S+·C9H6NO2− | C3H7N2S+·C6H6NO2− | C7H7N2S+·C9H6NO2− | C7H7N2S+·C6H6NO2− |
| Mr | 263.31 | 227.28 | 311.35 | 275.32 |
| Crystal system, space group | Monoclinic, P21/c | Orthorhombic, Pbca | Monoclinic, P21/c | Monoclinic, P21/c |
| Temperature (K) | 298 | 298 | 298 | 298 |
| a, b, c (Å) | 8.771 (2), 13.344 (5), 11.036 (2) | 11.9723 (8), 12.5938 (10), 15.063 (2) | 10.182 (4), 11.923 (2), 12.284 (6) | 5.5561 (9), 19.701 (3), 12.143 (2) |
| α, β, γ (°) | 90, 108.314 (8), 90 | 90, 90, 90 | 90, 107.23 (2), 90 | 90, 100.263 (8), 90 |
| V (Å3) | 1226.2 (6) | 2271.1 (4) | 1424.4 (9) | 1307.9 (4) |
| Z | 4 | 8 | 4 | 4 |
| Radiation type | Mo Kα | Mo Kα | Mo Kα | Mo Kα |
| µ (mm−1) | 0.26 | 0.27 | 0.24 | 0.25 |
| Crystal size (mm) | 0.50 × 0.30 × 0.24 | 0.50 × 0.40 × 0.18 | 0.60 × 0.20 × 0.18 | 0.50 × 0.30 × 0.10 |
| Data collection | ||||
| Diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer | Enraf Nonius CAD-4 diffractometer | Enraf-Nonius CAD-4 diffractometer |
| Absorption correction | ψ scan Xtal 3.2 (Hall et al., 1992) | – | ψ scan Xtal 3.2 (Hall et al., 1992) | ψ scan Xtal 3.2 (Hall et al., 1992) |
| Tmin, Tmax | 0.857, 0.939 | – | 0.899, 0.998 | 0.870, 0.998 |
| No. of measured, independent and observed [F > 4σ(F)] reflections | 2295, 2147, 1400 | 2025, 1995, 1182 | 2641, 2494, 1504 | 2552, 2302, 1440 |
| Rint | 0.018 | 0.021 | 0.076 | 0.036 |
| (sin θ/λ)max (Å−1) | 0.594 | 0.594 | 0.593 | 0.594 |
| Refinement | ||||
| R[F2 > 2σ(F2)], wR(F2), S | 0.036, 0.101, 1.00 | 0.037, 0.117, 1.00 | 0.051, 0.162, 0.94 | 0.038, 0.108, 0.99 |
| No. of reflections | 2147 | 1995 | 2494 | 2302 |
| No. of parameters | 216 | 170 | 251 | 224 |
| H-atom treatment | All H-atom parameters refined | H atoms treated by a mixture of independent and constrained refinement | All H-atom parameters refined | All H-atom parameters refined |
| Δρmax, Δρmin (e Å−3) | 0.17, −0.14 | 0.16, −0.16 | 0.27, −0.37 | 0.22, −0.27 |
| (9) | |
| Crystal data | |
| Chemical formula | C7H7N2S+·C5H3O2S− |
| Mr | 278.34 |
| Crystal system, space group | Monoclinic, P21/c |
| Temperature (K) | 293 |
| a, b, c (Å) | 9.162 (2), 11.121 (3), 12.033 (2) |
| α, β, γ (°) | 90, 104.388 (9), 90 |
| V (Å3) | 1187.6 (5) |
| Z | 4 |
| Radiation type | Mo Kα |
| µ (mm−1) | 0.44 |
| Crystal size (mm) | 0.48 × 0.24 × 0.20 |
| Data collection | |
| Diffractometer | Enraf-Nonius CAD-4 diffractometer |
| Absorption correction | ψ scan Xtal 3.2 (Hall et al., 1992) |
| Tmin, Tmax | 0.768, 0.915 |
| No. of measured, independent and observed [F > 4σ(F)] reflections | 2334, 2197, 1538 |
| Rint | 0.023 |
| (sin θ/λ)max (Å−1) | 0.621 |
| Refinement | |
| R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.156, 1.05 |
| No. of reflections | 2197 |
| No. of parameters | 191 |
| H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
| Δρmax, Δρmin (e Å−3) | 0.50, −0.53 |
Computer programs: MolEN (Fair,1990), Xtal3.2 (Hall et al., 1992), SHELXS97(Sheldrick, 1997), SHELXL97(Sheldrick, 1997), PLUTON94 (Spek, 1990), SHELXL97 (Sheldrick, 1997).
