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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 R^2_2(8) 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

cif

Crystallographic Information File (CIF)
Contains datablocks 4, 5, 7, 8, 9, global

sft

Structure factor file (SHELXL table format)
Supplementary material

sft

Structure factor file (SHELXL table format)
Supplementary material

sft

Structure factor file (SHELXL table format)
Supplementary material

sft

Structure factor file (SHELXL table format)
Supplementary material

sft

Structure factor file (SHELXL table format)
Supplementary material

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).

Figures top
[Figure 1]
[Figure 2]
(4) 2-amino-2-thiazolinium indole-2-carboxylate top
Crystal data top
C3H7N2S+·C9H6NO2F(000) = 552
Mr = 263.31Dx = 1.426 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 8.771 (2) Åθ = 6–14°
b = 13.344 (5) ŵ = 0.26 mm1
c = 11.036 (2) ÅT = 298 K
β = 108.314 (8)°Prism, colourless
V = 1226.2 (6) Å30.50 × 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 tubeRint = 0.018
Graphite monochromatorθmax = 25.0°, θmin = 2.5°
2θω scansh = 010
Absorption correction: ψ scan
Xtal 3.2 (Hall et al., 1992)
k = 015
Tmin = 0.857, Tmax = 0.939l = 1312
2295 measured reflections3 standard reflections every 200 reflections
2147 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.036All H-atom parameters refined
wR(F2) = 0.101Calculated w = 1/[σ2(Fo2) + (0.0499P)2 + 0.2456P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.001
2147 reflectionsΔρmax = 0.17 e Å3
216 parametersΔρmin = 0.14 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0036 (14)
Crystal data top
C3H7N2S+·C9H6NO2V = 1226.2 (6) Å3
Mr = 263.31Z = 4
Monoclinic, P21/cMo Kα radiation
a = 8.771 (2) ŵ = 0.26 mm1
b = 13.344 (5) ÅT = 298 K
c = 11.036 (2) Å0.50 × 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 = 0.9393 standard reflections every 200 reflections
2295 measured reflections intensity decay: 1%
2147 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0360 restraints
wR(F2) = 0.101All H-atom parameters refined
S = 1.00Δρmax = 0.17 e Å3
2147 reflectionsΔρmin = 0.14 e Å3
216 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.19795 (9)0.00838 (5)0.63845 (7)0.0583 (3)
N3A0.1661 (3)0.16112 (17)0.76836 (18)0.0496 (6)
C2A0.1381 (3)0.13027 (18)0.6507 (2)0.0436 (6)
N21A0.0701 (3)0.18557 (18)0.5505 (2)0.0532 (6)
C4A0.2472 (5)0.0918 (2)0.8682 (3)0.0635 (8)
C5A0.2952 (5)0.0013 (3)0.8081 (3)0.0687 (8)
H21A0.0460 (3)0.2540 (2)0.5610 (2)0.065 (8)*
H22A0.0720 (3)0.1660 (2)0.4710 (3)0.070 (9)*
H3A0.1470 (3)0.2280 (2)0.7850 (2)0.0580 (8)*
H41A0.3310 (4)0.1230 (3)0.9240 (3)0.1010 (13)*
H42A0.1690 (4)0.0740 (3)0.9120 (3)0.1070 (13)*
H51A0.2650 (4)0.0600 (3)0.8350 (3)0.087 (11)*
H52A0.4130 (5)0.0040 (3)0.8190 (3)0.116 (14)*
N1B0.1919 (3)0.07169 (15)0.13668 (19)0.0430 (5)
C2B0.2073 (3)0.00759 (17)0.23742 (19)0.0387 (5)
C21B0.1162 (3)0.08695 (17)0.2207 (2)0.0412 (6)
O21B0.1345 (2)0.14099 (12)0.31775 (14)0.0502 (5)
O22B0.0295 (2)0.10985 (12)0.10943 (15)0.0527 (5)
C3B0.3233 (3)0.04403 (19)0.3415 (2)0.0432 (6)
C4B0.5028 (3)0.2028 (2)0.3675 (2)0.0484 (6)
C5B0.5308 (3)0.2837 (2)0.3011 (3)0.0514 (7)
C6B0.4424 (3)0.2977 (2)0.1727 (3)0.0516 (7)
C7B0.3252 (3)0.23175 (19)0.1086 (2)0.0486 (6)
C8B0.2957 (3)0.14973 (17)0.1757 (2)0.0408 (6)
C9B0.3823 (3)0.13417 (17)0.3060 (2)0.0407 (6)
H1B0.1190 (3)0.0650 (2)0.0650 (2)0.061 (8)*
H3B0.3530 (3)0.01560 (17)0.4170 (2)0.044 (7)*
H4B0.5600 (3)0.1942 (18)0.4500 (2)0.054 (7)*
H5B0.6180 (3)0.3300 (2)0.3440 (2)0.065 (8)*
H6B0.4700 (3)0.3575 (19)0.1310 (2)0.053 (7)*
H7B0.2670 (3)0.2400 (18)0.0250 (2)0.049 (7)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0728 (5)0.0426 (4)0.0588 (4)0.0012 (4)0.0197 (4)0.0106 (3)
N3A0.0676 (15)0.0410 (13)0.0423 (12)0.0004 (12)0.0203 (11)0.0037 (10)
C2A0.0442 (14)0.0420 (14)0.0458 (14)0.0097 (12)0.0160 (11)0.0056 (12)
N21A0.0654 (15)0.0483 (14)0.0434 (13)0.0001 (12)0.0134 (11)0.0052 (11)
C4A0.084 (2)0.0550 (18)0.0494 (17)0.0019 (18)0.0182 (17)0.0002 (14)
C5A0.087 (3)0.0587 (19)0.0594 (18)0.0128 (19)0.0220 (17)0.0065 (15)
N1B0.0471 (12)0.0422 (12)0.0337 (11)0.0024 (10)0.0040 (10)0.0011 (9)
C2B0.0452 (13)0.0367 (13)0.0321 (11)0.0050 (11)0.0094 (10)0.0035 (10)
C21B0.0487 (14)0.0380 (13)0.0364 (13)0.0067 (11)0.0124 (11)0.0000 (10)
O21B0.0730 (12)0.0406 (10)0.0364 (9)0.0007 (9)0.0164 (8)0.0032 (8)
O22B0.0659 (12)0.0431 (10)0.0382 (9)0.0034 (9)0.0006 (8)0.0002 (7)
C3B0.0485 (15)0.0466 (14)0.0315 (13)0.0044 (12)0.0082 (11)0.0036 (11)
C4B0.0471 (15)0.0572 (17)0.0380 (14)0.0025 (14)0.0096 (12)0.0068 (13)
C5B0.0492 (15)0.0526 (16)0.0537 (15)0.0085 (14)0.0182 (13)0.0107 (13)
C6B0.0553 (16)0.0455 (15)0.0586 (16)0.0039 (14)0.0244 (13)0.0020 (13)
C7B0.0507 (16)0.0508 (16)0.0422 (14)0.0026 (13)0.0117 (12)0.0076 (13)
C8B0.0426 (14)0.0413 (14)0.0378 (12)0.0035 (12)0.0114 (10)0.0008 (11)
C9B0.0438 (14)0.0426 (14)0.0361 (12)0.0060 (12)0.0131 (11)0.0019 (10)
Geometric parameters (Å, º) top
S1A—C2A1.728 (3)C21B—O21B1.259 (3)
S1A—C5A1.800 (3)C21B—O22B1.262 (3)
N3A—C2A1.310 (3)C3B—C9B1.413 (3)
N3A—C4A1.443 (4)C4B—C5B1.369 (4)
C2A—N21A1.307 (3)C4B—C9B1.401 (3)
C4A—C5A1.500 (4)C5B—C6B1.398 (4)
N1B—C8B1.361 (3)C6B—C7B1.370 (4)
N1B—C2B1.375 (3)C7B—C8B1.390 (3)
C2B—C3B1.362 (3)C8B—C9B1.415 (3)
C2B—C21B1.474 (3)
C2A—S1A—C5A91.38 (14)O22B—C21B—C2B117.8 (2)
C2A—N3A—C4A116.7 (2)C2B—C3B—C9B108.2 (2)
N21A—C2A—N3A123.7 (2)C5B—C4B—C9B119.4 (2)
N21A—C2A—S1A122.30 (19)C4B—C5B—C6B120.8 (2)
N3A—C2A—S1A114.00 (19)C7B—C6B—C5B121.7 (3)
N3A—C4A—C5A108.6 (2)C6B—C7B—C8B117.7 (2)
C4A—C5A—S1A108.1 (2)N1B—C8B—C7B130.7 (2)
C8B—N1B—C2B109.52 (19)N1B—C8B—C9B107.5 (2)
C3B—C2B—N1B108.5 (2)C7B—C8B—C9B121.8 (2)
C3B—C2B—C21B130.0 (2)C4B—C9B—C3B135.1 (2)
N1B—C2B—C21B121.30 (19)C4B—C9B—C8B118.6 (2)
O21B—C21B—O22B124.4 (2)C3B—C9B—C8B106.3 (2)
O21B—C21B—C2B117.7 (2)
(5) '2-amino-2-thiazolinium N-methylpyrrole-2-carboxylate' top
Crystal data top
C3H7N2S+·C6H6NO2F(000) = 960
Mr = 227.28Dx = 1.329 Mg m3
Orthorhombic, PbcaMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2abCell parameters from 25 reflections
a = 11.9723 (8) Åθ = 6–14°
b = 12.5938 (10) ŵ = 0.27 mm1
c = 15.063 (2) ÅT = 298 K
V = 2271.1 (4) Å3Prism, colourless
Z = 80.50 × 0.40 × 0.18 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.021
Radiation source: fine-focus sealed tubeθmax = 25.0°, θmin = 2.7°
Graphite monochromatorh = 614
2θω scansk = 314
2025 measured reflectionsl = 917
1995 independent reflections3 standard reflections every 200 reflections
1182 reflections with F > 4σ(F) intensity decay: 1%
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.117Calculated w = 1/[σ2(Fo2) + (0.0574P)2 + 0.562P]
where P = (Fo2 + 2Fc2)/3
S = 1.00(Δ/σ)max = 0.017
1995 reflectionsΔρmax = 0.16 e Å3
170 parametersΔρmin = 0.16 e Å3
0 restraintsExtinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0030 (10)
Crystal data top
C3H7N2S+·C6H6NO2V = 2271.1 (4) Å3
Mr = 227.28Z = 8
Orthorhombic, PbcaMo Kα radiation
a = 11.9723 (8) ŵ = 0.27 mm1
b = 12.5938 (10) ÅT = 298 K
c = 15.063 (2) Å0.50 × 0.40 × 0.18 mm
Data collection top
Enraf-Nonius CAD-4
diffractometer
Rint = 0.021
2025 measured reflections3 standard reflections every 200 reflections
1995 independent reflections intensity decay: 1%
1182 reflections with F > 4σ(F)
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.117H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.16 e Å3
1995 reflectionsΔρmin = 0.16 e Å3
170 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.10396 (7)0.57877 (6)0.13695 (6)0.0765 (3)
C2A0.1789 (2)0.48668 (19)0.19779 (16)0.0487 (6)
N21A0.1328 (2)0.40105 (19)0.23002 (17)0.0578 (7)
N3A0.28489 (19)0.51026 (18)0.20692 (15)0.0544 (6)
C4A0.3214 (3)0.6114 (2)0.1713 (2)0.0620 (8)
C5A0.2256 (3)0.6608 (3)0.1213 (2)0.0766 (9)
H51A0.24360.66560.05870.096*
H52A0.21140.73180.14350.096*
N1B0.11048 (18)0.15572 (17)0.03712 (14)0.0531 (6)
C11B0.2006 (3)0.0842 (2)0.0623 (2)0.0782 (9)
H11B0.27060.11270.04210.098*
H12B0.20230.07700.12570.098*
H13B0.18850.01600.03560.098*
C2B0.0787 (2)0.2495 (2)0.07766 (16)0.0457 (6)
C21B0.1394 (2)0.3023 (2)0.15045 (17)0.0476 (6)
O21B0.09063 (14)0.37818 (15)0.18912 (13)0.0631 (6)
O22B0.23550 (15)0.27121 (15)0.16994 (13)0.0683 (6)
C3B0.0136 (2)0.2864 (2)0.03275 (18)0.0549 (7)
C4B0.0384 (3)0.2150 (3)0.0356 (2)0.0637 (8)
C5B0.0377 (3)0.1368 (3)0.03099 (19)0.0626 (8)
H21A0.175 (3)0.354 (2)0.2663 (19)0.072 (9)*
H22A0.066 (3)0.389 (2)0.219 (2)0.07 (1)*
H3A0.326 (2)0.469 (2)0.2373 (18)0.054 (8)*
H41A0.345 (2)0.657 (2)0.2217 (19)0.069 (9)*
H42A0.385 (3)0.601 (3)0.137 (2)0.095 (12)*
H3B0.048 (2)0.354 (2)0.0427 (17)0.059 (8)*
H4B0.095 (2)0.223 (2)0.0776 (19)0.065 (8)*
H5B0.051 (2)0.075 (2)0.0648 (17)0.06 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0593 (5)0.0643 (5)0.1057 (7)0.0058 (4)0.0187 (4)0.0246 (4)
C2A0.0467 (14)0.0485 (15)0.0509 (16)0.0046 (12)0.0058 (12)0.0000 (12)
N21A0.0447 (14)0.0544 (14)0.0744 (18)0.0046 (12)0.0118 (13)0.0114 (12)
N3A0.0437 (13)0.0539 (14)0.0657 (14)0.0003 (11)0.0070 (11)0.0128 (12)
C4A0.0586 (18)0.0491 (17)0.078 (2)0.0053 (14)0.0021 (18)0.0058 (15)
C5A0.077 (2)0.0633 (18)0.089 (2)0.0075 (16)0.0113 (18)0.0217 (17)
N1B0.0560 (14)0.0488 (13)0.0544 (13)0.0071 (11)0.0003 (11)0.0051 (10)
C11B0.078 (2)0.0587 (18)0.098 (2)0.0090 (17)0.0070 (18)0.0142 (18)
C2B0.0447 (13)0.0490 (13)0.0433 (13)0.0084 (12)0.0036 (12)0.0009 (11)
C21B0.0373 (14)0.0533 (15)0.0521 (15)0.0057 (12)0.0024 (12)0.0032 (12)
O21B0.0404 (10)0.0730 (12)0.0759 (13)0.0040 (9)0.0042 (9)0.0295 (11)
O22B0.0431 (11)0.0790 (14)0.0826 (14)0.0088 (9)0.0122 (10)0.0284 (11)
C3B0.0531 (16)0.0586 (18)0.0529 (16)0.0026 (14)0.0041 (14)0.0005 (14)
C4B0.066 (2)0.072 (2)0.0536 (18)0.0111 (17)0.0120 (16)0.0007 (16)
C5B0.073 (2)0.0606 (18)0.0542 (17)0.0161 (17)0.0002 (16)0.0126 (15)
Geometric parameters (Å, º) top
C2A—N21A1.305 (3)N1B—C11B1.456 (3)
C2A—N3A1.311 (3)C2B—C3B1.377 (4)
C2A—S1A1.729 (2)C2B—C21B1.474 (3)
N3A—C4A1.449 (3)C21B—O21B1.263 (3)
C4A—C5A1.506 (4)C21B—O22B1.250 (3)
C5A—S1A1.801 (3)C3B—C4B1.399 (4)
N1B—C5B1.367 (3)C4B—C5B1.343 (4)
N1B—C2B1.383 (3)
N21A—C2A—N3A123.9 (2)C3B—C2B—N1B107.0 (2)
N21A—C2A—S1A122.1 (2)C3B—C2B—C21B127.6 (3)
C2A—N3A—C4A116.9 (2)N1B—C2B—C21B125.3 (2)
N3A—C4A—C5A108.6 (2)O21B—C21B—O22B123.7 (2)
C4A—C5A—S1A108.3 (2)O21B—C21B—C2B117.1 (2)
C2A—S1A—C5A91.96 (13)O22B—C21B—C2B119.2 (2)
C5B—N1B—C2B107.7 (2)C2B—C3B—C4B108.4 (3)
C5B—N1B—C11B124.1 (2)C5B—C4B—C3B106.8 (3)
C2B—N1B—C11B128.1 (2)C4B—C5B—N1B110.1 (3)
(7) '2-Aminobenzothiazolium indole-2-carboxylate' top
Crystal data top
C7H7N2S+·C9H6NO2F(000) = 648
Mr = 311.35Dx = 1.452 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 10.182 (4) Åθ = 6–14°
b = 11.923 (2) ŵ = 0.24 mm1
c = 12.284 (6) ÅT = 298 K
β = 107.23 (2)°Prism, colourless
V = 1424.4 (9) Å30.60 × 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 tubeRint = 0.076
Graphite monochromatorθmax = 24.9°, θmin = 2.1°
2θω scansh = 012
Absorption correction: ψ scan
Xtal 3.2 (Hall et al., 1992)
k = 014
Tmin = 0.899, Tmax = 0.998l = 1413
2641 measured reflections3 standard reflections every 200 reflections
2494 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.051Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.162All H-atom parameters refined
S = 0.94Calculated w = 1/[σ2(Fo2) + (0.1084P)2]
where P = (Fo2 + 2Fc2)/3
2494 reflections(Δ/σ)max < 0.002
251 parametersΔρmax = 0.27 e Å3
0 restraintsΔρmin = 0.37 e Å3
Crystal data top
C7H7N2S+·C9H6NO2V = 1424.4 (9) Å3
Mr = 311.35Z = 4
Monoclinic, P21/cMo Kα radiation
a = 10.182 (4) ŵ = 0.24 mm1
b = 11.923 (2) ÅT = 298 K
c = 12.284 (6) Å0.60 × 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 = 0.9983 standard reflections every 200 reflections
2641 measured reflections intensity decay: 1%
2494 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0510 restraints
wR(F2) = 0.162All H-atom parameters refined
S = 0.94Δρmax = 0.27 e Å3
2494 reflectionsΔρmin = 0.37 e Å3
251 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.5868 (1)0.0512 (1)0.7713 (1)0.050 (1)
C2A0.4924 (4)0.1591 (3)0.6908 (3)0.042 (1)
N21A0.4031 (4)0.2180 (3)0.7244 (3)0.055 (1)
N3A0.5209 (3)0.1743 (3)0.5927 (2)0.041 (1)
C4A0.6687 (4)0.0969 (3)0.4822 (3)0.048 (1)
C5A0.7659 (4)0.0178 (4)0.4807 (4)0.059 (1)
C6A0.8130 (5)0.0576 (4)0.5696 (4)0.062 (1)
C7A0.7618 (4)0.0551 (3)0.6628 (4)0.054 (1)
C8A0.6655 (4)0.0256 (3)0.6648 (3)0.043 (1)
C9A0.6186 (3)0.1007 (3)0.5747 (3)0.039 (1)
H21A0.3562 (4)0.2721 (4)0.6782 (4)0.068 (13)*
H22A0.3892 (4)0.2011 (4)0.7879 (3)0.054 (11)*
H3A0.477 (4)0.221 (4)0.549 (4)0.061 (13)*
H4A0.633 (4)0.145 (3)0.426 (3)0.049 (10)*
H5A0.801 (4)0.015 (3)0.426 (3)0.059 (12)*
H6A0.882 (4)0.118 (3)0.568 (3)0.063 (11)*
H7A0.799 (4)0.098 (3)0.7280 (3)0.055 (11)*
N1B0.8511 (3)0.0547 (2)1.0434 (3)0.046 (1)
C2B0.7533 (3)0.0009 (3)1.0797 (3)0.040 (1)
C21B0.6908 (3)0.1046 (3)1.0194 (3)0.041 (1)
O21B0.6067 (3)0.1589 (2)1.0558 (2)0.050 (1)
O22B0.7264 (3)0.1292 (2)0.9327 (2)0.055 (1)
C3B0.7375 (4)0.0523 (3)1.1721 (3)0.041 (1)
C4B0.8588 (4)0.2304 (3)1.2797 (3)0.051 (1)
C5B0.9547 (4)0.3096 (3)1.2754 (4)0.056 (1)
C6B1.0198 (4)0.3093 (4)1.1912 (4)0.058 (1)
C7B0.9939 (4)0.2284 (3)1.1090 (3)0.053 (1)
C8B0.8968 (3)0.1465 (3)1.1116 (3)0.041 (1)
C9B0.8271 (3)0.1468 (3)1.1954 (3)0.040 (1)
H1B0.872 (4)0.039 (3)0.984 (3)0.058 (12)*
H3B0.678 (4)0.033 (3)1.209 (3)0.060 (12)*
H4B0.813 (4)0.233 (3)1.342 (3)0.053 (10)*
H5B0.975 (4)0.361 (3)1.327 (3)0.058 (12)*
H6B1.086 (4)0.369 (3)1.191 (3)0.054 (10)*
H7B1.044 (4)0.226 (3)1.056 (3)0.065 (12)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.057 (1)0.052 (1)0.040 (1)0.001 (1)0.013 (1)0.014 (1)
C2A0.048 (2)0.042 (2)0.034 (2)0.005 (2)0.010 (2)0.008 (2)
N21A0.072 (2)0.057 (2)0.044 (2)0.012 (2)0.028 (2)0.012 (2)
N3A0.048 (2)0.040 (2)0.035 (2)0.002 (1)0.011 (1)0.006 (1)
C4A0.057 (2)0.047 (2)0.040 (2)0.000 (2)0.015 (2)0.004 (2)
C5A0.065 (3)0.061 (3)0.057 (3)0.003 (2)0.029 (2)0.005 (2)
C6A0.062 (3)0.047 (2)0.080 (3)0.009 (2)0.023 (2)0.004 (2)
C7A0.054 (2)0.046 (2)0.057 (2)0.005 (2)0.009 (2)0.011 (2)
C8A0.048 (2)0.037 (2)0.041 (2)0.005 (2)0.010 (2)0.003 (2)
C9A0.043 (2)0.034 (2)0.039 (2)0.002 (2)0.008 (2)0.001 (2)
N1B0.057 (2)0.044 (2)0.040 (2)0.004 (2)0.019 (1)0.001 (1)
C2B0.043 (2)0.035 (2)0.039 (2)0.003 (2)0.010 (2)0.004 (2)
C21B0.051 (2)0.037 (2)0.033 (2)0.001 (2)0.010 (2)0.003 (2)
O21B0.068 (2)0.043 (1)0.042 (1)0.013 (1)0.021 (1)0.001 (1)
O22B0.077 (2)0.050 (2)0.047 (2)0.008 (1)0.032 (1)0.009 (1)
C3B0.045 (2)0.041 (2)0.041 (2)0.002 (2)0.019 (2)0.001 (2)
C4B0.059 (2)0.045 (2)0.049 (2)0.001 (2)0.016 (2)0.008 (2)
C5B0.065 (3)0.042 (2)0.057 (3)0.001 (2)0.012 (2)0.010 (2)
C6B0.056 (3)0.049 (2)0.064 (3)0.015 (2)0.010 (2)0.004 (2)
C7B0.053 (2)0.056 (2)0.052 (2)0.006 (2)0.019 (2)0.010 (2)
C8B0.045 (2)0.038 (2)0.039 (2)0.000 (2)0.010 (2)0.006 (2)
C9B0.043 (2)0.037 (2)0.040 (2)0.001 (2)0.013 (2)0.000 (2)
Geometric parameters (Å, º) top
S1A—C2A1.730 (3)N1B—C2B1.376 (4)
S1A—C8A1.751 (4)C2B—C3B1.351 (5)
C2A—N21A1.308 (5)C2B—C21B1.484 (5)
C2A—N3A1.334 (4)C21B—O22B1.257 (4)
N3A—C9A1.393 (4)C21B—O21B1.257 (4)
C4A—C5A1.371 (6)C3B—C9B1.424 (5)
C4A—C9A1.377 (5)C4B—C5B1.371 (6)
C5A—C6A1.385 (6)C4B—C9B1.404 (5)
C6A—C7A1.392 (6)C5B—C6B1.384 (6)
C7A—C8A1.379 (5)C6B—C7B1.364 (6)
C8A—C9A1.394 (5)C7B—C8B1.397 (5)
N1B—C8B1.373 (4)C8B—C9B1.413 (5)
C2A—S1A—C8A90.17 (17)C3B—C2B—C21B132.1 (3)
N21A—C2A—N3A124.7 (3)N1B—C2B—C21B118.9 (3)
N21A—C2A—S1A122.7 (3)O22B—C21B—O21B125.4 (3)
N3A—C2A—S1A112.6 (3)O22B—C21B—C2B115.4 (3)
C2A—N3A—C9A114.5 (3)O21B—C21B—C2B119.2 (3)
C5A—C4A—C9A118.6 (4)C2B—C3B—C9B108.2 (3)
C4A—C5A—C6A121.3 (4)C5B—C4B—C9B118.1 (4)
C5A—C6A—C7A120.5 (4)C4B—C5B—C6B122.1 (4)
C8A—C7A—C6A118.1 (4)C7B—C6B—C5B121.6 (4)
C7A—C8A—C9A120.8 (3)C6B—C7B—C8B117.4 (4)
C7A—C8A—S1A128.3 (3)N1B—C8B—C7B131.1 (3)
C9A—C8A—S1A110.9 (3)N1B—C8B—C9B107.1 (3)
C4A—C9A—C8A120.7 (3)C7B—C8B—C9B121.7 (3)
C4A—C9A—N3A127.5 (3)C4B—C9B—C8B119.0 (3)
C8A—C9A—N3A111.8 (3)C4B—C9B—C3B134.7 (3)
C8B—N1B—C2B109.5 (3)C8B—C9B—C3B106.3 (3)
C3B—C2B—N1B108.9 (3)
(8) '2-aminobenzothiazolium N-methylpyrrole-2-carboxylate' top
Crystal data top
C7H7N2S+·C6H6NO2F(000) = 576
Mr = 275.32Dx = 1.398 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 5.5561 (9) Åθ = 6–14°
b = 19.701 (3) ŵ = 0.25 mm1
c = 12.143 (2) ÅT = 298 K
β = 100.263 (8)°Prism, colourless
V = 1307.9 (4) Å30.50 × 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 tubeRint = 0.036
Graphite monochromatorθmax = 25.0°, θmin = 2.0°
2θω scansh = 06
Absorption correction: ψ scan
Xtal 3.2 (Hall et al., 1992)
k = 023
Tmin = 0.870, Tmax = 0.998l = 1414
2552 measured reflections3 standard reflections every 200 reflections
2302 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.038Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.108All H-atom parameters refined
S = 0.99Calculated w = 1/[σ2(Fo2) + (0.0544P)2 + 0.2231P]
where P = (Fo2 + 2Fc2)/3
2302 reflections(Δ/σ)max < 0.002
224 parametersΔρmax = 0.22 e Å3
0 restraintsΔρmin = 0.27 e Å3
Crystal data top
C7H7N2S+·C6H6NO2V = 1307.9 (4) Å3
Mr = 275.32Z = 4
Monoclinic, P21/cMo Kα radiation
a = 5.5561 (9) ŵ = 0.25 mm1
b = 19.701 (3) ÅT = 298 K
c = 12.143 (2) Å0.50 × 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 = 0.9983 standard reflections every 200 reflections
2552 measured reflections intensity decay: 1%
2302 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0380 restraints
wR(F2) = 0.108All H-atom parameters refined
S = 0.99Δρmax = 0.22 e Å3
2302 reflectionsΔρmin = 0.27 e Å3
224 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.00630 (14)0.33873 (4)0.48861 (6)0.0386 (2)
C2A0.2038 (5)0.29032 (14)0.4325 (2)0.0349 (6)
N21A0.3906 (5)0.26062 (14)0.4945 (2)0.0430 (6)
N3A0.155 (4)0.2871 (1)0.3217 (2)0.0364 (6)
C4A0.1389 (6)0.33343 (16)0.1601 (2)0.0437 (7)
C5A0.3439 (6)0.37330 (16)0.1296 (3)0.0475 (8)
C6A0.4606 (6)0.40344 (16)0.2091 (3)0.0465 (8)
C7A0.3724 (5)0.39458 (15)0.3216 (3)0.0410 (7)
C8A0.1644 (5)0.35563 (13)0.3535 (2)0.0330 (6)
C9A0.0507 (5)0.32445 (13)0.2729 (2)0.0347 (6)
N1B0.9112 (4)0.08034 (12)0.27295 (19)0.0435 (6)
C11B1.0778 (8)0.0949 (3)0.3773 (3)0.0659 (11)
C2B0.6982 (5)0.11363 (13)0.2273 (2)0.0340 (6)
C21B0.5973 (5)0.17185 (14)0.2800 (2)0.0351 (6)
O21B0.4199 (4)0.20326 (10)0.21895 (15)0.0434 (5)
O22B0.6802 (4)0.18681 (11)0.37872 (15)0.0509 (6)
C3B0.6062 (6)0.08196 (14)0.1284 (2)0.0382 (7)
C4B0.7644 (6)0.02900 (16)0.1129 (3)0.0465 (8)
C5B0.9498 (7)0.02926 (16)0.2023 (3)0.0500 (8)
H21A0.492 (6)0.2372 (16)0.462 (3)0.052 (9)*
H22A0.422 (5)0.2713 (15)0.566 (3)0.050 (9)*
H3A0.2370 (6)0.2621 (16)0.284 (3)0.060 (10)*
H4A0.054 (6)0.3157 (15)0.106 (3)0.056 (9)*
H5A0.404 (5)0.3814 (14)0.053 (2)0.049 (9)*
H6A0.605 (6)0.4294 (16)0.184 (2)0.052 (9)*
H7A0.448 (5)0.4138 (13)0.376 (2)0.036 (7)*
H11B1.098 (9)0.143 (3)0.394 (4)0.134 (19)*
H12B1.223 (8)0.070 (2)0.377 (3)0.104 (15)*
H13B0.998 (8)0.080 (2)0.439 (3)0.095 (15)*
H3B0.457 (5)0.0933 (13)0.084 (2)0.041 (8)*
H4B0.751 (6)0.0011 (16)0.051 (3)0.055 (9)*
H5B1.100 (6)0.0017 (15)0.218 (2)0.048 (8)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0387 (4)0.0454 (4)0.0329 (4)0.0059 (4)0.0102 (3)0.0046 (3)
C2A0.0362 (16)0.0377 (15)0.0319 (14)0.0011 (13)0.0094 (13)0.0017 (12)
N21A0.0427 (15)0.0545 (16)0.0315 (13)0.0137 (13)0.0055 (12)0.0052 (12)
N3A0.0391 (14)0.0398 (14)0.0320 (12)0.0053 (11)0.0105 (11)0.0043 (10)
C4A0.051 (2)0.0472 (18)0.0324 (15)0.0009 (16)0.0073 (14)0.0032 (14)
C5A0.050 (2)0.0522 (19)0.0354 (17)0.0012 (16)0.0063 (15)0.0010 (15)
C6A0.0363 (18)0.0449 (18)0.0551 (19)0.0021 (15)0.0007 (15)0.0021 (15)
C7A0.0365 (17)0.0422 (17)0.0453 (18)0.0002 (14)0.0098 (14)0.0040 (14)
C8A0.0343 (16)0.0309 (14)0.0339 (14)0.0053 (12)0.0065 (12)0.0017 (11)
C9A0.0332 (16)0.0317 (15)0.0392 (15)0.0036 (12)0.0062 (12)0.0010 (11)
N1B0.0379 (14)0.0440 (14)0.0478 (15)0.0064 (12)0.0051 (11)0.0076 (11)
C11B0.053 (2)0.075 (3)0.062 (2)0.019 (2)0.012 (2)0.012 (2)
C2B0.0334 (16)0.0327 (14)0.0369 (15)0.0017 (12)0.0088 (12)0.0020 (12)
C21B0.0364 (16)0.0396 (15)0.0310 (14)0.0003 (13)0.0103 (12)0.0017 (12)
O21B0.0503 (13)0.0484 (12)0.0323 (10)0.0168 (10)0.0094 (9)0.0009 (9)
O22B0.0579 (14)0.0603 (14)0.0332 (11)0.0167 (11)0.0040 (10)0.0079 (10)
C3B0.0379 (17)0.0396 (16)0.0369 (16)0.0015 (14)0.0064 (14)0.0011 (13)
C4B0.053 (2)0.0367 (16)0.0512 (19)0.0018 (15)0.0138 (16)0.0117 (15)
C5B0.049 (2)0.0389 (17)0.064 (2)0.0094 (16)0.0158 (17)0.0031 (15)
Geometric parameters (Å, º) top
S1A—C2A1.738 (3)C8A—C9A1.398 (4)
S1A—C8A1.750 (3)N1B—C5B1.364 (4)
C2A—N21A1.307 (4)N1B—C2B1.380 (3)
C2A—N3A1.326 (3)N1B—C11B1.458 (4)
N3A—C9A1.399 (3)C2B—C3B1.369 (4)
C4A—C5A1.379 (4)C2B—C21B1.472 (4)
C4A—C9A1.381 (4)C21B—O22B1.240 (3)
C5A—C6A1.389 (4)C21B—O21B1.282 (3)
C6A—C7A1.378 (4)C3B—C4B1.398 (4)
C7A—C8A1.383 (4)C4B—C5B1.357 (4)
C2A—S1A—C8A89.82 (13)C8A—C9A—N3A111.8 (2)
N21A—C2A—N3A124.1 (3)C5B—N1B—C2B108.5 (2)
N21A—C2A—S1A122.7 (2)C5B—N1B—C11B123.0 (3)
N3A—C2A—S1A113.2 (2)C2B—N1B—C11B128.4 (3)
C2A—N3A—C9A114.1 (2)C3B—C2B—N1B107.2 (2)
C5A—C4A—C9A118.0 (3)C3B—C2B—C21B128.7 (3)
C4A—C5A—C6A121.5 (3)N1B—C2B—C21B124.1 (2)
C7A—C6A—C5A120.5 (3)O22B—C21B—O21B124.0 (2)
C8A—C7A—C6A118.6 (3)O22B—C21B—C2B120.1 (2)
C7A—C8A—C9A120.5 (2)O21B—C21B—C2B115.9 (2)
C7A—C8A—S1A128.5 (2)C2B—C3B—C4B108.2 (3)
C9A—C8A—S1A111.0 (2)C5B—C4B—C3B107.2 (3)
C4A—C9A—C8A120.8 (3)C4B—C5B—N1B108.9 (3)
C4A—C9A—N3A127.3 (3)
(9) '2-aminobenzothiazolium thiophene-2-carboxylate' top
Crystal data top
C7H7N2S+·C5H3O2SF(000) = 576
Mr = 278.34Dx = 1.557 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 25 reflections
a = 9.162 (2) Åθ = 6–14°
b = 11.121 (3) ŵ = 0.44 mm1
c = 12.033 (2) ÅT = 293 K
β = 104.388 (9)°Prism, colourless
V = 1187.6 (5) Å30.48 × 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 tubeRint = 0.023
Graphite monochromatorθmax = 26.2°, θmin = 2.3°
2θω scansh = 011
Absorption correction: ψ scan
Xtal 3.2 (Hall et al., 1992)
k = 013
Tmin = 0.768, Tmax = 0.915l = 1413
2334 measured reflections3 standard reflections every 200 reflections
2197 independent reflections intensity decay: 1%
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.05Calculated w = 1/[σ2(Fo2) + (0.0791P)2 + 1.2898P]
where P = (Fo2 + 2Fc2)/3
2197 reflections(Δ/σ)max = 0.001
191 parametersΔρmax = 0.50 e Å3
0 restraintsΔρmin = 0.53 e Å3
Crystal data top
C7H7N2S+·C5H3O2SV = 1187.6 (5) Å3
Mr = 278.34Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.162 (2) ŵ = 0.44 mm1
b = 11.121 (3) ÅT = 293 K
c = 12.033 (2) Å0.48 × 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 = 0.9153 standard reflections every 200 reflections
2334 measured reflections intensity decay: 1%
2197 independent reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0490 restraints
wR(F2) = 0.156H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.50 e Å3
2197 reflectionsΔρmin = 0.53 e Å3
191 parameters
Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
S1A0.06852 (10)0.06403 (9)0.75046 (8)0.0429 (3)
C2A0.0521 (4)0.1630 (3)0.7869 (3)0.0369 (8)
N21A0.1589 (4)0.2112 (3)0.7121 (3)0.0475 (9)
N3A0.0232 (3)0.1846 (3)0.8991 (2)0.0380 (7)
C4A0.1475 (4)0.1258 (4)1.0809 (3)0.0439 (9)
C5A0.2660 (5)0.0557 (4)1.1290 (3)0.0502 (10)
C6A0.3297 (5)0.0150 (4)1.0609 (4)0.0506 (10)
C7A0.2780 (4)0.0179 (4)0.9433 (3)0.0450 (9)
C8A0.1591 (4)0.0512 (3)0.8954 (3)0.0370 (8)
C9A0.0939 (4)0.1223 (3)0.9636 (3)0.0358 (8)
S1B0.43616 (13)0.60626 (11)0.84787 (12)0.0681 (4)
C2B0.3181 (4)0.5215 (3)0.9447 (3)0.0403 (8)
C21B0.2615 (4)0.4083 (3)0.9074 (3)0.0409 (9)
O21B0.1768 (3)0.3465 (2)0.9826 (2)0.0489 (7)
O22B0.3012 (3)0.3811 (3)0.8037 (2)0.0558 (8)
C3B0.2836 (5)0.5744 (3)1.0561 (3)0.0420 (9)
H3B0.21600.54371.12070.053*
C4B0.3679 (6)0.6800 (4)1.0526 (4)0.0639 (12)
H4B0.36560.72711.11690.080*
C5B0.4508 (5)0.7060 (4)0.9494 (5)0.0653 (13)
H5B0.51210.77370.93410.082*
H21A0.215 (5)0.256 (4)0.738 (4)0.060 (14)*
H22A0.173 (4)0.194 (4)0.645 (4)0.048 (12)*
H3A0.0800 (6)0.237 (5)0.929 (4)0.077 (16)*
H4A0.097 (4)0.182 (3)1.124 (3)0.045 (10)*
H5A0.309 (5)0.057 (4)1.215 (4)0.053 (11)*
H6A0.399 (5)0.060 (4)1.090 (4)0.050 (12)*
H7A0.323 (4)0.057 (4)0.894 (3)0.048 (11)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S1A0.0452 (5)0.0530 (6)0.0315 (5)0.0079 (4)0.0113 (4)0.0066 (4)
C2A0.0421 (19)0.038 (2)0.0319 (18)0.0005 (15)0.0108 (15)0.0043 (15)
N21A0.0512 (19)0.060 (2)0.0308 (18)0.0145 (16)0.0096 (15)0.0038 (16)
N3A0.0407 (16)0.0434 (17)0.0310 (15)0.0034 (14)0.0111 (12)0.0038 (13)
C4A0.046 (2)0.053 (2)0.0334 (19)0.0007 (18)0.0126 (16)0.0049 (17)
C5A0.053 (2)0.062 (3)0.033 (2)0.000 (2)0.0056 (17)0.0010 (19)
C6A0.047 (2)0.054 (3)0.047 (2)0.009 (2)0.0042 (18)0.002 (2)
C7A0.044 (2)0.047 (2)0.045 (2)0.0045 (17)0.0114 (17)0.0092 (18)
C8A0.0389 (18)0.041 (2)0.0317 (18)0.0024 (15)0.0097 (14)0.0032 (15)
C9A0.0382 (17)0.0377 (19)0.0332 (18)0.0001 (15)0.0119 (14)0.0010 (15)
S1B0.0608 (7)0.0600 (8)0.0747 (8)0.0099 (6)0.0000 (6)0.0015 (6)
C2B0.0406 (19)0.040 (2)0.044 (2)0.0034 (15)0.0167 (16)0.0082 (16)
C21B0.048 (2)0.044 (2)0.036 (2)0.0045 (16)0.0200 (16)0.0036 (16)
O21B0.0693 (18)0.0643 (19)0.0327 (15)0.0206 (15)0.0107 (13)0.0020 (13)
O22B0.0638 (16)0.0535 (16)0.0316 (13)0.0207 (14)0.0160 (12)0.0060 (12)
C3B0.068 (2)0.0287 (18)0.0353 (19)0.0117 (17)0.0248 (17)0.0028 (15)
C4B0.075 (3)0.050 (3)0.073 (3)0.001 (2)0.030 (3)0.012 (2)
C5B0.052 (2)0.037 (2)0.108 (4)0.0036 (19)0.024 (3)0.000 (2)
Geometric parameters (Å, º) top
S1A—C2A1.692 (3)C8A—C9A1.378 (5)
S1A—C8A1.741 (3)S1B—C2B1.670 (4)
C2A—N21A1.272 (5)S1B—C5B1.680 (5)
C2A—N3A1.332 (4)C2B—C3B1.425 (5)
N3A—C9A1.349 (4)C2B—C21B1.474 (5)
C4A—C5A1.345 (6)C21B—O22B1.243 (4)
C4A—C9A1.376 (5)C21B—O21B1.247 (4)
C5A—C6A1.367 (6)C3B—C4B1.400 (6)
C6A—C7A1.377 (6)C4B—C5B1.317 (7)
C7A—C8A1.341 (5)
C2A—S1A—C8A88.47 (17)N3A—C9A—C8A110.7 (3)
N21A—C2A—N3A124.4 (3)C4A—C9A—C8A122.0 (3)
N21A—C2A—S1A121.9 (3)C2B—S1B—C5B91.1 (2)
N3A—C2A—S1A113.7 (3)C3B—C2B—C21B128.8 (3)
C2A—N3A—C9A114.8 (3)C3B—C2B—S1B112.2 (3)
C5A—C4A—C9A118.0 (4)C21B—C2B—S1B119.0 (3)
C4A—C5A—C6A119.7 (4)O22B—C21B—O21B124.6 (3)
C5A—C6A—C7A122.8 (4)O21B—C21B—C2B117.0 (3)
C8A—C7A—C6A117.6 (4)O22B—C21B—C2B118.4 (3)
C7A—C8A—C9A120.0 (3)C4B—C3B—C2B109.0 (4)
C7A—C8A—S1A127.7 (3)C5B—C4B—C3B113.4 (4)
C9A—C8A—S1A112.3 (3)C4B—C5B—S1B114.2 (4)
N3A—C9A—C4A127.3 (3)

Experimental details

(4)(5)(7)(8)
Crystal data
Chemical formulaC3H7N2S+·C9H6NO2C3H7N2S+·C6H6NO2C7H7N2S+·C9H6NO2C7H7N2S+·C6H6NO2
Mr263.31227.28311.35275.32
Crystal system, space groupMonoclinic, P21/cOrthorhombic, PbcaMonoclinic, P21/cMonoclinic, P21/c
Temperature (K)298298298298
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), 9090, 90, 9090, 107.23 (2), 9090, 100.263 (8), 90
V3)1226.2 (6)2271.1 (4)1424.4 (9)1307.9 (4)
Z4844
Radiation typeMo KαMo KαMo KαMo Kα
µ (mm1)0.260.270.240.25
Crystal size (mm)0.50 × 0.30 × 0.240.50 × 0.40 × 0.180.60 × 0.20 × 0.180.50 × 0.30 × 0.10
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Enraf Nonius CAD-4
diffractometer
Enraf-Nonius CAD-4
diffractometer
Absorption correctionψ 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, Tmax0.857, 0.9390.899, 0.9980.870, 0.998
No. of measured, independent and
observed [F > 4σ(F)] reflections
2295, 2147, 1400 2025, 1995, 1182 2641, 2494, 1504 2552, 2302, 1440
Rint0.0180.0210.0760.036
(sin θ/λ)max1)0.5940.5940.5930.594
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 reflections2147199524942302
No. of parameters216170251224
H-atom treatmentAll H-atom parameters refinedH atoms treated by a mixture of independent and constrained refinementAll H-atom parameters refinedAll H-atom parameters refined
Δρmax, Δρmin (e Å3)0.17, 0.140.16, 0.160.27, 0.370.22, 0.27


(9)
Crystal data
Chemical formulaC7H7N2S+·C5H3O2S
Mr278.34
Crystal system, space groupMonoclinic, 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
V3)1187.6 (5)
Z4
Radiation typeMo Kα
µ (mm1)0.44
Crystal size (mm)0.48 × 0.24 × 0.20
Data collection
DiffractometerEnraf-Nonius CAD-4
diffractometer
Absorption correctionψ scan
Xtal 3.2 (Hall et al., 1992)
Tmin, Tmax0.768, 0.915
No. of measured, independent and
observed [F > 4σ(F)] reflections
2334, 2197, 1538
Rint0.023
(sin θ/λ)max1)0.621
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.156, 1.05
No. of reflections2197
No. of parameters191
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)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).

 
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