Home Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
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Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2

  • Huawei Tang , Qianqian Han and Lijuan Liu ORCID logo EMAIL logo
Published/Copyright: March 6, 2023
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Zeitschrift für Kristallographie - New Crystal Structures
From the journal Zeitschrift für Kristallographie - New Crystal Structures Volume 238 Issue 3

Abstract

C17H37N9O3S2, monoclinic, P21/c (no. 14), a = 8.8492(13) Å, b = 17.285(3) Å, c = 16.810(3) Å, β = 93.493(2)°, V = 2566.4(7) Å3, Z = 4, R gt(F) = 0.0395, wR ref(F 2) = 0.1277, T = 296(2) K.

CCDC no: 2239232

Table 1 contains crystallographic data and Table 2 contains the list of the atoms including atomic coordinates and displacement parameters.

Table 1:

Data collection and handling.

Crystal: Colorless block
Size: 0.50 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.24 mm−1
Diffractometer, scan mode: Bruker APEX-II, φ and ω
θ max, completeness: 25.0°, >99%
N(hkl)measured, N(hkl)unique, R int: 12,815, 4511, 0.027
Criterion for I obs, N(hkl)gt: I obs > 2σ(I obs), 3774
N(param)refined: 286
Programs: Bruker [1], SHELX [2, 3]
Table 2:

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2).

Atom x Y z U iso*/U eq
S1 0.12243 (6) 0.17443 (3) 0.59153 (3) 0.04788 (17)
C1 0.1383 (2) 0.10176 (10) 0.46849 (11) 0.0414 (4)
N1 0.07948 (19) 0.09445 (9) 0.53823 (10) 0.0506 (4)
O1 0.37108 (19) 0.39474 (8) 0.57551 (9) 0.0631 (4)
O1W 0.2481 (2) 0.04833 (11) 0.24913 (10) 0.0709 (5)
H1WA 0.312 (3) 0.0115 (13) 0.2426 (16) 0.106*
H1WB 0.244 (3) 0.0757 (15) 0.2056 (11) 0.106*
S2 0.43503 (6) 0.13059 (3) 0.73061 (3) 0.05315 (18)
C2 0.21949 (19) 0.21342 (10) 0.51537 (10) 0.0386 (4)
N2 0.1206 (2) 0.04674 (10) 0.41115 (11) 0.0592 (5)
H2A 0.0697 0.0055 0.4198 0.071*
H2B 0.1603 0.0531 0.3662 0.071*
O2 0.21952 (19) 0.31527 (9) 0.64117 (8) 0.0597 (4)
C3 0.2935 (2) 0.33514 (11) 0.58270 (11) 0.0465 (5)
N3 0.21863 (17) 0.16771 (8) 0.45213 (9) 0.0419 (4)
C4 0.3784 (2) 0.19067 (10) 0.80634 (11) 0.0431 (4)
N4 0.28868 (19) 0.28350 (9) 0.51791 (9) 0.0484 (4)
H4A 0.3335 0.2976 0.4763 0.058*
C5 0.5103 (2) 0.09813 (10) 0.86760 (11) 0.0428 (4)
N5 0.2969 (2) 0.25515 (10) 0.79488 (10) 0.0575 (5)
H5A 0.2740 0.2827 0.8350 0.069*
H5B 0.2674 0.2692 0.7474 0.069*
N6 0.42830 (18) 0.16483 (9) 0.87695 (9) 0.0432 (4)
C6 0.3234 (2) 0.80349 (13) 0.82371 (13) 0.0562 (5)
H6A 0.3909 0.7693 0.7969 0.067*
H6B 0.3858 0.8387 0.8564 0.067*
N7 0.5300 (2) 0.07139 (9) 0.79536 (10) 0.0506 (4)
C7 0.2309 (3) 0.75532 (19) 0.87778 (17) 0.0858 (8)
H7A 0.1589 0.7885 0.9026 0.103*
H7B 0.1740 0.7171 0.8461 0.103*
N8 0.5714 (2) 0.06313 (10) 0.93440 (10) 0.0580 (5)
H8D 0.6251 0.0220 0.9306 0.070*
H8E 0.5563 0.0821 0.9805 0.070*
C8 0.3265 (4) 0.7150 (2) 0.94119 (18) 0.1016 (10)
H8A 0.2629 0.6853 0.9739 0.152*
H8B 0.3965 0.6813 0.9170 0.152*
H8C 0.3814 0.7526 0.9735 0.152*
N9 0.23328 (16) 0.85037 (10) 0.76111 (10) 0.0474 (4)
C9 0.1309 (2) 0.90868 (13) 0.79916 (14) 0.0577 (5)
H9A 0.0803 0.9392 0.7571 0.069*
H9B 0.0535 0.8805 0.8256 0.069*
C10 0.2082 (3) 0.96331 (18) 0.85885 (19) 0.0910 (9)
H10A 0.2704 0.9335 0.8972 0.109*
H10B 0.2746 0.9974 0.8312 0.109*
C11 0.1029 (5) 1.0096 (3) 0.9010 (3) 0.1485 (18)
H11A 0.1580 1.0431 0.9379 0.223*
H11B 0.0424 1.0402 0.8635 0.223*
H11C 0.0383 0.9763 0.9295 0.223*
C12 0.3501 (2) 0.89099 (13) 0.71169 (13) 0.0519 (5)
H12A 0.4115 0.9243 0.7470 0.062*
H12B 0.4166 0.8518 0.6917 0.062*
C13 0.2889 (3) 0.93893 (15) 0.64195 (14) 0.0649 (6)
H13A 0.2363 0.9838 0.6612 0.078*
H13B 0.2173 0.9086 0.6090 0.078*
C14 0.4181 (3) 0.96494 (17) 0.59285 (15) 0.0755 (7)
H14A 0.3786 0.9954 0.5486 0.113*
H14B 0.4881 0.9955 0.6255 0.113*
H14C 0.4692 0.9204 0.5735 0.113*
C15 0.1293 (2) 0.79903 (12) 0.70784 (14) 0.0537 (5)
H15A 0.0557 0.7753 0.7407 0.064*
H15B 0.0741 0.8318 0.6693 0.064*
C16 0.2058 (3) 0.73593 (14) 0.66329 (15) 0.0660 (6)
H16A 0.2512 0.6989 0.7010 0.079*
H16B 0.2859 0.7581 0.6336 0.079*
C17 0.0938 (4) 0.6951 (2) 0.6067 (2) 0.1111 (13)
H17A 0.1446 0.6552 0.5789 0.167*
H17B 0.0153 0.6725 0.6361 0.167*
H17C 0.0500 0.7316 0.5689 0.167*

Source of materials

Amidinothiourea and tetrapropylammonium hydroxide (25% aqueous solution) were mixed in a molar ratio of 1:2. The mixture was dissolved in a minimum amount of ethanol and water to form the related mixture, then the mixture was vigorously stirred for about 1 h. Subsequently the clean solution was set aside to allow it slow evaporation at room temperature. Colorless block crystals were obtained about 10 days later. It can be concluded that some amidinothiourea.

Comment

1,3,5-Thiadiazole-5-amido-2-carbamate is a derived compound of amidinothiourea, and amidinothiourea is a key pharmaceutical intermediate of famotidine [4]. In 2012, only two inclusion compounds of the carbamate were reported with the existence of the tetrapropylammonium and tetrabutylammonium counter cation [5]. Also, one dihydrate of tetraethylammonium 1,3,5-thiadiazole-5-amido-2-carbamate was reported in 2022 [6]. It can be seen that the crystal structure of tetrapropylammonium 1,3,5-thiadiazole-5-amido-2-carbamate and 1,2,4-thiadiazole-3,5-diamine was not reported until now. As to 1,2,4-thiadiazole-3,5-diamine, it can be analyzed this compound is also a derivative of amidinothiourea under basic conditions, which is just like 1,3,5-thiadiazole-5-amido-2-carbamate. Compared with 1,3,5-thiadiazole-5-amido-2-carbamate, 1,2,4-thiadiazole-3,5-diamine doesn’t absorb extra CO2 to further yield the additional carboxyl group in the concrete structure. In fact, it has been reported that 1,2,4-thiadiazole-3,5-diamine can be synthesized by amidinothiourea with the existence of H2O2 [7]. Obviously, 1,2,4-thiadiazole-3,5-diamine can be obtained under different experimental conditions.

In the asymmetric unit of the crystal structure, there exist one tetrapropylammonium, one 1,3,5-thiadiazole-5-amido-2-carbamate, 1,2,4-thiadiazole-3,5-diamine and one water molecule. Analyzing the crystal structure, it can be seen that 1,2,4-thiadiazole-3,5-diamine an 1,3,5-thiadiazole-5-amido-2-carbamate firstly connect with each other to form a hydrogen-bonded dimer by two N–H⋯N donor hydrogen bonds and one O⋯H–N acceptor hydrogen bond, then the dimers are further linked with the water molecules by O–H⋯O and O–H⋯N contacts to generate a 3D hydrogen-bonded network with rhombic cavities. As to tetrapropylammonium cations, they are regularly accommodated among the cavities to form the packed crystal structure. The crystal structure of the title compound can be compared with the structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate and amidinothiourea that reported in 2012 [5]. It is interesting that amidinothiourea and 1,3,5-thiadiazole-5-amido-2-carbamate also link with each other to be a similar dimer, then the dimers are connected by water molecules to form a similar host lattice with rhombic cavities, in which tetrapropylammonium cations are also contained to form the stable structure. Observing the title structure and the reported structure, the prominent difference of the hydrogen-bonded frameworks is the formation of N–H⋯S hydrogen bonding that only exist in the latter structure. In the title compound, there is no N–H⋯S contact due to the formation of the heterocycle. Thus, it can be seen that 1,2,4-thiadiazole-3,5-diamine should be very similar with amidinothiourea in their spatial configurations. Compound, and it can yield various derivatives under suitable conditions.

Corresponding author: Lijuan Liu, Department of Science and Technology, Henan University of Chinese Medicine, Zhengzhou, 450046, China, E-mail:

Acknowledgements

We gratefully acknowledge support by Henan University of Chinese Medicine.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: Henan University of Chinese Medicine.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

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Received: 2022-12-05
Accepted: 2023-02-01
Published Online: 2023-03-06
Published in Print: 2023-06-27

© 2022 the author(s), published by De Gruyter, Berlin/Boston

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
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  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
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  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
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  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
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https://doi.org/10.1515/ncrs-2022-0566
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Articles in the same Issue

  1. Frontmatter
  2. New Crystal Structures
  3. Crystal structure of phenyl(3,3-dichloro-1,3-dihydro-2H-pyrrolo[2,3-b]pyridin-2-one)methanone, C7H4Cl2N2O
  4. Crystal structure of poly[diaqua-bis(μ 2-1,4-diaminobutane-N:N′)cobalt(II)] dichloride, C8H28Cl2CoN4O2
  5. Synthesis and crystal structure of (4aR,7S)-7-hydroxy-7-isopropyl-1,1-dimethyldecahydro-2H,6H-8a,4a-(epoxymethano)phenanthren-12-one, C20H32O3
  6. The crystal structure of 1-(2-chlorobenzyl)-3-(3,5-dichlorophenyl)urea, C14H11Cl3N2O
  7. Crystal structure of tetrapropylammonium-1,3,5-thiadiazole-5-amido-2-carbamate – 1,2,4-thiadiazole-3,5-diamine – water (1/1/1), C17H37N9O3S2
  8. Tetrabutylammonium 1,3,5-thiadiazole-5-amido-2-carbamate—1,2,4-thiadiazole-3,5-diamine— water (1/1/1), C21H45N9O3S2
  9. The crystal structure of ((E)-2,4-dichloro-6-(((2-hydroxy-5-nitrophenyl)imino)methyl)phenolato-κ 3 N,O,O′)tris(pyridine-κN)manganese(II), C28H21Cl2MnN5O4
  10. The crystal structure of aqua-bis{2-bromo-6-((2-(2-phenylacetyl)hydrazineylidene)methyl)phenolato-κ3 N,O,O′}-dimethylformamide-κ1 O-erbium(III) chloride – dimethylformamide – water (1/2/1), C39H49N7O9Br2ClEr
  11. Crystal structure of (diaqua-bis(phenanthroline-K 2 N,N′)-tetrakis(m 2-3,4,5,6-tetrafluorophthalato-K 4 O,O:O′:O″;K 2 O:O′)dierbium (III) phenanthroline (1/2), C80H38Er2F16N8O18
  12. Crystal structure of (E)-7-methoxy-2-(4-methoxy-2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C20H17F3O3
  13. The crystal structure of 4–(4,4,5,5–tetramethyl–1,3,2–dioxaborolan–2–yl)morpholine, C10H20BNO3
  14. The crystal structure of catena–poly[aqua(1-naphthoato-κ 2 O,O′)-(μ-1-naphthoato-κ 4 O:O,O′:O′)lead(II)], C22H16O5Pb
  15. The crystal structure of 1-(4-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  16. The crystal structure of 4-(pyren-1-yl)butyl-4-nitrobenzoate, C27H21NO4
  17. Crystal structure of cyclo-(bis(µ2-3,3′-(1H-imidazole-3-ium-1,3-diyl)dipropionato-κ4 O,O′:O″,O″′)-dinitrato-κ2 O,O′-tetraoxido-diuranium(VI) C18H22N6O18U2
  18. The crystal structure of catena-[nitrato-κ 2 O,O′-(μ 3-3-iodobenzene-1,2-dicarboxylato-κ 4 O:O′:O″,O‴)-(2,2′:6′,2″-terpyridine-κ 3 N,N′,N″)lanthanum(III)], C23H14IN4O7La
  19. Redetermination of crystal structure of [bis(pyridin-2-ylmethyl)amine-κ 3 N,Nʹ,Nʺ]chloridopalladium(II) chloride monohydrate
  20. Crystal structure of catena-poly[triaqua-[bis(m2-4-(1H-1,2,4-triazol-1-yl)benzoato-k2O:O')-(4-(1H-1,2,4-triazol-1-yl)benzoato-k1O)-praseodymium (III) monohydrate], C27H26N9O10Pr
  21. Crystal structure of trans-diaqua-bis(methyl methylcarbamohydrazonothioato-κ2 N,N′) nickel(II) iodide semihydrate, C6H22N6O2NiS2I2·0.5H2O
  22. The crystal structure of 2-(2-fluoro-4-methyl-5-((2,2,2-trifluoroethyl)thio)phenyl)isoindolin-1-one, C17H13F4NOS
  23. The crystal structure of di-μ-1-naphthylacetato-κ 3 O,O′:O;κ 3 O:O,O′-bis[(1-naphthylacetato-κ 2 O,O′)(2,2′-bipyridine-κ 2 N,N′)lead(II)] monohydrate, C68H54N4O9Pb2
  24. Crystal structure of tetrapropylammonium guanidinium 4,4′-sulfonyldibenzoate monohydrate, C27H44N4O7S
  25. Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
  26. Crystal structure of (E)-7-fluoro-2-(4-morpholinobenzylidene)-3,4-dihydronaphthalen-1(2H)-one, C21H20FNO2
  27. The crystal structure of poly[diaqua-bis(μ 3-5-bromobenzene-1,3-dicarboxylato-κ 3 O,O,O′)-(μ 2-1,3-bis-(4-pyridyl)-propane-κ 2 N,N′)-dizinc(II))] – 5-bromobenzene-1,3-dicarboxylic acid [2/1], C37H29Br3N2O14Zn2
  28. The crystal structure of 2-bromo-1,3-phenylene bis(4-methylbenzenesulfonate), C20H17BrO6S2
  29. Crystal structure of europium dichromium icosaaluminum, EuCr2Al20
  30. The crystal structure of N′1,N′3-di((E)-benzylidene) isophthalohydrazide dihydrate, C 22 H 22 N 4 O 4
  31. Crystal structure of 7α,11α-dihydroxy-15-oxo-ent-kauran-16-en-19,6β-olide, C20H26O5
  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
  33. The crystal structure of (Z)-3-(1-(2-((E)-4-isopropylbenzylidene)hydrazinyl)ethylidene) chroman-2,4-dione, C21H20N2O3
  34. Crystal structure of E-7-fluoro-2-(2-(trifluoromethyl)benzylidene)-3,4-dihydronaphthalen-1(2H)-one, C18H12F4O
  35. Crystal structure of bis(6-aminopyridine-2-carboxylato–k2O,N)-bis(N,N-dimethylformamide-k1 O)zinc(II), C18H24N6O6Zn
  36. Crystal structure of 5-(adamantan-1-yl)-3-[(4-{[2-(trifluoromethyl)phenyl]-methyl}piperazin-1-yl)methyl]-1,3,4-oxadiazole-2(3H)-thione, C25H31F3N4OS
  37. Crystal structure of tetrapropylammonium bicarbonate–1-(diaminomethylene)thiourea – water (2/2/1), C30H72N10O7S2
  38. Crystal structure of tris(2,2′-bipyridine-κ2 N,N′)iron(II) triiodide – dichloromethane (2/1), C61H50Cl2Fe2I12N12
  39. Crystal structure of 2-amino-3-[2-(1,3,3-trimethyl-1,3-dihydro-indol-2-ylidene)-ethylideneamino]-but-2-enedinitrile, C17H17N5
  40. The crystal structure of 1-(2-chlorophenyl)-3-cycloheptylurea, C14H19ClN2O
  41. Crystal structure of potassium bis(pentaselenido-κ 2 Se 1,Se 5)palladate(II), K2[Pd(Se5)2]
  42. The crystal structure of 5,10-bis(2-methoxyethyl)-5,10-dihydro-[1,2,3,4]tetrathiocino[5,6-b:8, 7-b′]diindole, C22H22N2O2S4
  43. The crystal structure of 4-(4-iodophenyl)-5H-1,2,3-dithiazole-5-thione, C8H4INS3
  44. Crystal structure of bis{μ2-(4-acetyl-phenoxy)acetato-κ2 O:O′}-bis{μ2-(4-acetyl-phenoxy)acetato-κ3 O,O′:O)- bis{(4-acetyl-phenoxy)acetato-κ2 O,O′}-bis(phenanthrolin-κ2 N,N′)didysprosium(III) tetrahydrate, C84H78N4O28Dy2
  45. Crystal structure of Eu2Pd3.37(1)Zn13.63(1)
  46. Crystal structure of 2-methoxy-4-(methoxy-carbonyl)phenyl 2-chloro-4-fluorobenzoate, C16H12ClFO5
  47. Crystal structure of catena-poly[bis(μ2-dicyanamide-κ2 N:N′)-bis(4-vinylpyridine-κN)-copper(II)], C18H14CuN8
  48. The crystal structure of iguratimod-dimethylformamide (1/1), C17H14N2O6S·C3H7NO
  49. Synthesis and crystal structure of 1-((3R,10S,13S,17S)-10,13-dimethyl-3-(m-tolylamino)hexadecahydro-1H-cyclopenta[α]phenanthren-17-yl)ethan-1-one, C28H41NO
  50. The crystal structure of diaqua-bis(4-bromo-2-formylphenoxy)zinc(II), C14H12Br2O6Zn
  51. The crystal structure of tetra(1-ethylimidazole-κ 1 N)-[μ 4-imidazole-4,5-dicarboxylato-κ 4 O, N, O′, N′]-trioxido-divanadium, C25H33N10O7V2
  52. The crystal structure of (E)-N′-(1-(4-fluorophenyl)propylidene)-2-hydroxybenzohydrazide, C16H15FN2O2
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