Startseite Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S
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Crystal structure of bis(tetrapropylammonium) terephthalate – 1-(diaminomethylene)thiourea – water (1/2/4) C18H40N5O4S

  • Mengfei Li , Fangfang Geng und Honglei Zhu ORCID logo EMAIL logo
Veröffentlicht/Copyright: 23. März 2023

Abstract

C18H40N5O4S, monoclinic, P21/n (no. 14), a = 8.4254(9) Å, b = 8.4254(9) Å, c = 16.1470(17) Å, β = 98.302(2)°, V = 2411.9(4) Å3, Z = 4, R gt(F) = 0.0409, wR ref(F 2) = 0.1162, T = 296(2) K.

CCDC no.: 2247423

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: 0.40 × 0.20 × 0.20 mm
Wavelength: Mo Kα radiation (0.71073 Å)
μ: 0.17 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: 12,101, 4245, 0.021
Criterion for I obs, N(hkl)gt: I obs > 2 σ(I obs), 3591
N(param)refined: 253
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
C1 0.34682 (19) 0.85885 (9) 0.53201 (10) 0.0377 (4)
N1 0.4709 (2) 1.01283 (8) 0.11194 (10) 0.0543 (4)
H1A 0.4659 1.0325 0.0630 0.065*
H1B 0.4503 1.0394 0.1534 0.065*
O1 0.32977 (15) 0.84318 (6) 0.60614 (7) 0.0491 (3)
S1 0.51596 (6) 0.90591 (3) 0.22298 (3) 0.05203 (16)
O1W 0.47721 (18) 0.15818 (9) 0.22663 (9) 0.0674 (4)
H1WA 0.4518 0.2044 0.2190 0.101*
H1WB 0.5438 0.1569 0.2720 0.101*
C2 0.42669 (17) 0.93211 (8) 0.51590 (9) 0.0328 (3)
N2 0.53983 (18) 0.90651 (7) 0.05306 (8) 0.0421 (3)
O2 0.30074 (18) 0.81831 (7) 0.46993 (8) 0.0618 (4)
O2W 0.2278 (2) 0.79113 (9) 0.29901 (9) 0.0752 (4)
H2WA 0.3080 0.8084 0.2790 0.113*
H2WB 0.2592 0.8023 0.3499 0.113*
C3 0.47187 (19) 0.98258 (9) 0.57998 (10) 0.0382 (4)
H3A 0.4538 0.9713 0.6341 0.046*
N3 0.6209 (2) 0.81132 (9) −0.02399 (10) 0.0659 (5)
H3B 0.6705 0.7699 −0.0287 0.079*
H3C 0.5766 0.8345 −0.0680 0.079*
C4 0.45618 (19) 0.95030 (9) 0.43571 (10) 0.0388 (4)
H4A 0.4272 0.9169 0.3920 0.047*
N4 0.68277 (18) 0.80151 (8) 0.11661 (9) 0.0485 (4)
H4B 0.7312 0.7603 0.1093 0.058*
H4C 0.6800 0.8180 0.1664 0.058*
C5 0.51118 (19) 0.94056 (9) 0.12356 (10) 0.0392 (4)
N5 0.00279 (15) 0.05238 (8) 0.25538 (9) 0.0419 (3)
C6 0.6126 (2) 0.83952 (9) 0.05139 (10) 0.0404 (4)
C8 −0.1172 (2) 0.10458 (11) 0.20593 (12) 0.0510 (4)
H8A −0.1671 0.1345 0.2451 0.061*
H8B −0.2007 0.0748 0.1741 0.061*
C9 −0.0480 (3) 0.15670 (13) 0.14604 (14) 0.0720 (6)
H9A 0.0477 0.1804 0.1750 0.086*
H9B −0.0174 0.1279 0.1000 0.086*
C10 −0.1652 (4) 0.2150 (2) 0.1125 (2) 0.1264 (13)
H10A −0.1178 0.2469 0.0750 0.190*
H10B −0.2592 0.1917 0.0829 0.190*
H10C −0.1942 0.2441 0.1579 0.190*
C11 0.1380 (2) 0.09682 (10) 0.30580 (11) 0.0461 (4)
H11A 0.2018 0.0629 0.3439 0.055*
H11B 0.2068 0.1161 0.2675 0.055*
C12 0.0861 (2) 0.16127 (12) 0.35598 (13) 0.0590 (5)
H12A 0.0270 0.1971 0.3184 0.071*
H12B 0.0150 0.1430 0.3937 0.071*
C13 0.2278 (3) 0.19921 (12) 0.40571 (13) 0.0638 (5)
H13A 0.1914 0.2398 0.4369 0.096*
H13B 0.2854 0.1640 0.4436 0.096*
H13C 0.2973 0.2180 0.3684 0.096*
C14 −0.0891 (2) 0.00804 (10) 0.31340 (11) 0.0470 (4)
H14A −0.1317 0.0427 0.3507 0.056*
H14B −0.1795 −0.0159 0.2798 0.056*
C15 0.0067 (3) −0.05105 (13) 0.36585 (16) 0.0713 (6)
H15A 0.0561 −0.0843 0.3296 0.086*
H15B 0.0915 −0.0274 0.4039 0.086*
C16 −0.0984 (3) −0.09537 (15) 0.41519 (19) 0.0928 (9)
H16A −0.0350 −0.1324 0.4479 0.139*
H16B −0.1460 −0.0626 0.4517 0.139*
H16C −0.1813 −0.1195 0.3776 0.139*
C17 0.0802 (2) 0.00133 (11) 0.19762 (12) 0.0537 (5)
H17A 0.1340 0.0321 0.1607 0.064*
H17B 0.1618 −0.0282 0.2314 0.064*
C18 −0.0324 (3) −0.05121 (14) 0.14445 (16) 0.0775 (7)
H18A −0.0841 −0.0838 0.1804 0.093*
H18B −0.1151 −0.0226 0.1103 0.093*
C19 0.0577 (3) −0.09743 (16) 0.08885 (17) 0.0900 (8)
H19A −0.0155 −0.1304 0.0556 0.135*
H19B 0.1076 −0.0651 0.0527 0.135*
H19C 0.1385 −0.1262 0.1227 0.135*

Source of materials

Amidinothiourea, terephthalic acid and tetrapropylammonium hydroxide (25% aqueous solution), which are commercially available, were mixed in a molar ratio of 1:1:2. The mixture was dissolved in a minimum amount of ethanol and water, then stirred for about 35 min. Subsequently the clean solution was set aside to allow slow evaporation at room temperature. Colorless block crystals were obtained about seven days.

Comment

Amidinothiourea, a derivative of thiourea, can be utilized to synthesize the related organic crystals to explore supramolecular architecture [4, 5]. The amidinothiourea as an approximately planar molecule is composed of two triangular motifs, and it would form various hydrogen bonds by the NH2 groups if the appropriate hydrogen bond acceptor were provided. Searching in the related literatures, it can be seen the crystal structures of tetrabutylammonium sulfanilate – 1-(diaminomethylene)thiourea [6] and terephthalate-1-(diaminomethylene)thiourea [7] are reported.

In the asymmetric unit of the title compound, there exist one independent 1-(diaminomethylene)thiourea, one half terephthalate positioned on the symmetry center, one tetrapropylammonium cation and two water molecules. Analyzing the crystal structure, the neutral amidinothiourea molecules firstly form a dimer by a pair of N–H···N hydrogen bonds, then the dimer links with the terephthalate by N–H···O hydrogen bonds to generate a zigzag chain extended along the b axis. Consecutively, the hydrogen-bonded chains interact with two independent water molecules by varied O–H···O contacts to regularly arrange to yield a 3-dimensional hydrogen-bonded framework with channels.


Corresponding author: Honglei Zhu, School of Information Technology, Henan University of Chinese Medicine, Zhengzhou 450046, China, E-mail:

Funding source: Doctoral Fund of Henan University of Chinese Medicine

Award Identifier / Grant number: BSJJ2022-15

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

  2. Research funding: This work was funded by Doctoral Fund of Henan University of Chinese Medicine. (BSJJ2022-15).

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

References

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Received: 2023-02-03
Accepted: 2023-03-09
Published Online: 2023-03-23
Published in Print: 2023-06-27

© 2023 the author(s), published by De Gruyter, Berlin/Boston

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

Artikel in diesem Heft

  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
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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
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  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
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  32. Crystal structure of 4-chloro-N′-[(1E)-pyridin-3-ylmethylidene]benzohydrazide, C13H10ClN3O
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