Synthesis and crystal structure of N,N′-bis(4-chlorophenyl)thiourea N,N-dimethylformamide

Article abstract of DOI:10.1515/chem-2020-0061

This study is about the synthesis of N,N′-bis(4-chlorophenyl)thiourea N,N-dimethylformamide (C16H17Cl2N3OS) compound. Single crystals of the compound were obtained by slow evaporation of N,N′-bis(4-chlorophenyl)thiourea (C13H10Cl2N2S) in N,N-dimethylforma

Full text of DOI:10.1515/chem-2020-0061

Open Chemistry 2021; 19: 511–517
Research Article
Ayodele T. Odularu*, Peter A. Ajibade, Opeoluwa O. Oyedeji, Johannes Z. Mbese,
Horst Puschmann
Synthesis and crystal structure of N,N′-bis(4-
chlorophenyl)thiourea N,N-dimethylformamide
https://doi.org/10.1515/chem-2020-0061
received October 21, 2018; accepted April 2, 2020
Chemistry name is 2-thiourea, while the atomic formula
for thiourea is CS(NH ) [1]. Thiourea has numerous
2
2
applications in agriculture, health and metallurgy [1].
Thiourea derivatives are useful anticancer agents [1,3].
Several ways of synthesizing thiourea have been
reported [1,2]. Methods reported to synthesize thiourea
involve intermediaries, such as carbon disulphide and
ammonium thiocyanate isomerization, cyanamide, cya-
namide–hydrogen sulphide, lime nitrogen, urea–calcium
cyanamide and urea–cyanamide [4–6].
Abstract: This study is about the synthesis of N,N′-bis(4-
chlorophenyl)thiourea N,N-dimethylformamide (C H Cl N OS)
1
6 17 2 3
compound. Single crystals of the compound were obtained
by slow evaporation of N,N′-bis(4-chlorophenyl)thiourea
(
C H Cl N S) in N,N-dimethylformamide (C H NO; DMF)
13
10
2
2
3 7
through recrystallization under mild condition. Important
classical N–H⋯O links the two molecules together. Results
revealed that C H Cl N OS crystallized in the monoclinic
16
17
2 3
The synthetic method to yield thiourea from urea–
cyanamide involves dehydrated urea under normal pres-
sure from the reaction of ammonia and carbon(IV) oxide
to form cyanamide (H CN ) [5]. The H CN reaction with
space group P2 /c with the respective cell parameters of
1
a = 92,360 (4) Å, b = 7.2232 (3) Å, 25.2555 (11) Å, β = 91.376
3
(
3), α = γ = 90°, V = 1684.40 (12) Å , T = 119.94 (13) K and
2
2
2
2
Z = 4 and Z′ = 1.
hydrogen sulphide forms thiourea. This method, which
Keywords: thiourea, dimethylformamide, crystal struc- is of high production cost, usually gives a low yield
ture, monoclinic
of thiourea because of many side reactions which take
place during the reaction process. Another demerit in
this method is the difficulty encountered in the reaction
because of carbon(IV) oxide inertness [5].
1
Introduction
In the case of method involving urea–calcium cyana-
mide (Ca(OCN) ) as intermediary, calcium cyanamide
2
Thiourea belongs to the class of organic compounds con- and calcium oxide are used as reactants to form the inter-
taining sulphur [1]. It is a broad-spectrum compound mediate product, namely Ca(OCN) . The Ca(OCN) reacts
2
2
used in synthetic chemistry [2]. Thiourea belongs to the with H S to form thiourea. This method is also flawed
2
thioamide class of compounds. The structure is similar to with high production cost and low product yield.
urea and has a general formula of (R R N)(R R N)C]S Additionally, the produced viscous Ca(OCN) as inter-
1
2
3
4
2
[
1]. Thiourea is also referred to as thiocarbamide and mediate during the reaction process cannot be removed
sulphourea. The International Union of Pure and Applied from the subsequent reaction in the thiourea synthesis,
due to the lack of supporting apparatus [5]. The by-pro-
duct, calcium hydroxide (Ca(OH) ), produced along with
2
2


H S, has low solubility in water, which forms a thick
*
Corresponding author: Ayodele T. Odularu, Department of
agglomerate in the reaction vessel, and as a result affects
reaction progress.
Chemistry, University of Fort Hare, Private Bag X1314, Alice 5700,
South Africa, e-mail: 201106223@ufh.ac.za,
ayodeleodularu@gmail.com
The method involving carbon(IV) sulphide (CS ) uses
2
Peter A. Ajibade: Department of Chemistry, School of Chemistry and CS and ammonia (NH ) as reactants, as the same reac-
2
3
Physics, University of KwaZulu-Natal, Pietermaritzburg Campus,
Scottsville 3209, South Africa
Opeoluwa O. Oyedeji, Johannes Z. Mbese: Department of Chemistry,
University of Fort Hare, Private Bag X1314, Alice 5700, South Africa
Horst Puschmann: Chemistry Department, Durham University,
Dublin, United Kingdom
tants apply to the synthesis of dithiocarbamate [5,7]. The
decomposition reaction between both reactants gives
ammonium thiocyanate, which is isomerized to form
thiourea, and H S as by-product [5]. This method also
2
gives a low yield because of ammonium thiocyanate
Open Access. © 2021 Ayodele T. Odularu et al., published by De Gruyter.
This work is licensed under the Creative Commons Attribution 4.0
International License.

512

Ayodele T. Odularu et al.
isomerization as well as properties of both ammonium Merck (Germany). All chemicals and reagents were used
thiocyanate and thiourea. Additionally, no efficient separa- as received without further purification.
tion method was used in the synthesis due to the reaction
vessel’s neck. The method involving ammonium thiocya-
nate isomerization uses ammonium thiocyanate as the reac-
tant to obtain thiourea. The reaction’s demerits are high 2.2 Synthesis of C H Cl N S
1
3
10
2 3
production cost and low yield. The method involving lime
nitrogen uses calcium oxide and water as reactants to pro- The methods used were in line with Azizi et al. and
duce lime milk, which absorbs hydrogen sulphide to obtain Maddani and Prabhu methods, though with some modifi-
calcium hydrosulphide with a better yield [5].
cations [10,11]. To a methanolic solution containing
Synthesis of thiourea through cyanamide–hydrogen para-chloroaniline (1 mmol) and cold carbon(IV) sulphide
sulphide uses cyanamide and a catalyst (as an improved (6.00 mL, 1 mmol), ammonia solution (4.00 mL) was added
atmospheric molecular sieve) in the urea atmospheric dropwise. Reaction temperature was less than 4°C with con-
pressure dehydration stage, which is accomplished in an tinuous stirring for 3 h at room temperature (298 K), which
ammonia atmosphere to form cyanamide. The thiourea is gave a product of white precipitates. The product was fil-
then synthesized in a concentrated cyanamide solution tered, washed several times with diethyl ether solvent to
and hydrogen sulphide gas. It gives a low reaction product remove unreacted reactants [7] and dried in vacuo over
of thiourea [5,7]. Among the aforementioned methods, the silica gel. Yield was high to give 84% of the product. The
CS method was applicable to this study because of the chemical reaction is shown in Scheme 1.
2
availabilities and accessibilities of the reactants [7].
However, in an attempt to synthesize chloroaniline
dithiocarbamate (C H ClN S NH ), a new crystalline com-
7
6
2
2
4
pound of thiourea (C H Cl N S) was formed. The thiourea 2.3 Formation of C H Cl N OS crystals
13
10
2
2
16 17
2 3
was formed from a mixture of chloroaniline, carbon(IV)
sulphide and ammonia solution in methanol at a tempera- The C H Cl N S (50 mg, 0.11 mmol) was placed in a 100-
1
3
10
2 2
ture of less than 4°C [5]. In order to confirm the structure, mL conical flask. Methanol (7 mL) and DMF (5 mL) were
crystal growth by slow evaporation at room temperature added to C H Cl N S in the 100 mL conical flask. This
1
3
10
2 2
was carried out on a quantity of the product (solid white was stirred on a magnetic stirrer until all the solute dis-
precipitate) in N,N-dimethylformamide (DMF). The struc- solved in the solvent mixture to give a clear solution. The
tural determination was carried out with single crystal flask was covered with punched aluminium foil and kept
X-ray diffraction characterization technique. In this article, in a fume cupboard. The reaction vessel was allowed to
we present the crystal structure of C H Cl N OS. Specific evaporate slowly at room temperature. Filtration method
16
17
2 3
intermolecular interactions are halogen bonds, orthogonal was used to collect single, large and white polygon crys-
multipolar interactions, halogen and aromatic rings, hydro- tals, which were dried over silica gel in a desiccator. The
phobic interaction and hydrogen bonds (Scheiner 2016). percentage yield obtained was 84%.
Existence of specific interaction, such as NH–O between
two partner molecules, has made molecular recognition to
rely on it for stability and strength [8,9].
2
.4 Study of C H Cl N OS
16 17 2 3
3
3
3
A suitable crystal 0.17 mm × 0.12 mm × 0.10 mm was
selected and mounted on a tip of a glass fibre with a small
quantity of silicon grease and later placed on a goniometer
head [12]. Data were collected on a Xcalibur, AtlasS2,
Gemini ultra diffractometer (Agilent Technologies XRD
2
Experimental
2
.1 Materials
P-Chloroaniline and ammonia solution were purchased
from BDH Laboratory Reagents (England), while carbon(IV)
sulphide was supplied by Associated Chemical Enterprises
2
C H ClNH
+ CS2(l) + 2NH3(l)
C13H10Cl N S
+ 3H2(g) +H2S
(g)
+N2(g)
6
4
2(aq)
2
2
(s)
(
Pty) Ltd (South Africa). N,N-DMF was purchased from Scheme 1: Synthesis of N,N′-bis(4-chlorophenyl)thiourea.

Synthesis and crystal structure of C16
H
17Cl
N
2 3
OS

513
Products, Oxfordshire, United Kingdom) with graphite-mono- Table 1: Single-crystal X-ray diffraction analysis of C16
H17Cl
2
3
N OS
and its structural refinement parameters
chromatized Mo-Kα radiation at 150 K. The crystal was kept
at T = 119.94 (13) K during data collection. CrysAlisPro soft-
Crystal data
ware package was used to refine, reduce and integrate
the data for Lorentz polarization. Corrections for the absorp- Empirical formula
tion (multi-scan) were also performed using CrysAlisPro Formula weight (M
Crystal colour
C16H Cl N OS
370.30
White
0.17 × 0.12 × 0.10
Monoclinic
1
P2 /c
Polygon
9.2360 (4)
7.2232 (3)
25.2555 (11)
90
91.376 (3)
90
1684.40 (12)
4
17
2 3
r
)
1
.171.39.12b [13]. Empirical absorption correction using
Crystal size (mm)
Crystal system
Space group
Shape
spherical harmonics was implemented in SCALE3 ABSPACK
scaling algorithm. Coordinates of bulk non-hydrogen atoms
were established by direct methods using CrysAlisPro [13].
Locations of the outstanding non-hydrogen bonding were a/Å
b/Å
c/Å
α/°
β/°
positioned with a combination of least-square refinement
in CrysAlisPro program. Other hydrogen atoms were posi-
tioned in geometrically calculated locations. The model
was refined with version 2017/1 of olex2.refine [14] using
γ/°
3
Gauss–Newton minimization. Crystal data and refinement V/Å
parameters are shown in Table 1.
Z
Z′
1
T/K
D
119.94 (13)
1.4601
1.54184
4.684
Ethical approval: The conducted research is not related to
either human or animal use.
calc./g cm−
1
Cu-Kα radiation, λ (Å)
μ/mm−
1
θ
max
67.61°
GoF
1.0403
3
Result and discussion
Data collection
Excalibur Gemini ultra-
diffractometer (Atlas)
Absorption correction
Single source at offset
The title compound was synthesized, and the crystal
structure is reported here. Related structure can be seen
in Ghorab et al. [15]. The standard bond-length data can
Multi-scan Gaussian
Jana 2006
X-ray tube
0.199
be seen in Allen et al. [16]. For bond lengths, other sub- Radiation source
stituted thioureas can be seen in Rauf et al. and Saeed et
al. [17,18]. For earlier reported C]S distances, bond dis-
tances can be seen in Bailey et al. [19].
T
T
min
max
1
Refinement
Restraints
0
Measured reflections
Independent reflections
Reflections used
2,991
2,989
2,642
0.0000
276
3
.1 Structural description and tabular
results of C H Cl N OS
R
int
1
6
17
2 3
Parameters
Largest peak
Deepest hole
0.3145
−0.3414
0.0991
0.0938
0.0389
0.0336
The compound of C H Cl N OS crystallized in mono-
1
6
17
2 3
clinic system, space group P2 /c, and the crystallographic
1
wR
wR
2
(all data)
independent unit has a twin chlorophenyl azanide ring
2
linked to a carbon monosulphide bond at the basal R (all data)
1
(
Figure 1). Intrinsic phasing using the ShelXT structure
R
1
solution program was used to solve the structure [20],
while Gauss–Newton version 2017/1 of olex2 was used to
refine the structure [14]. All non-hydrogen atoms were ani- Table S2. Bond lengths in Å and bond angles in ° for
sotropically refined with CrysAlisPro 1.171.39.12b [21]. Frac-
OS are given in Tables S3 and S4, respectively.
tional atomic coordinates (×10 ) and equivalent isotropic On the other hand, the hydrogen fractional atomic coordi-
C H17Cl N
16 2 3
4
2
3
4
displacement parameters (Å × 10 ) for C H Cl N OS are nates (×10 ) and equivalent isotropic displacement para-
16
17
2 3
2
3
summarized in Table S1, while the anisotropic displacement meters (Å × 10 ) for C16
parameters (×10 ) for C H Cl N OS are summarized in and hydrogen bond information is given in Table S6. The
H17Cl
N
OS are given in Table S5,
2
3
4
16
17
2 3

514

Ayodele T. Odularu et al.
due to the presence of intermolecular hydrogen bonding
data given in Table S5).
In C H Cl N OS, two benzene rings enclose a dihe-
(
1
6
17
2 3
dral angle of 111.05 (18)°, while the corresponding angle
from the carbonyl groups of the DMF is 124.9 (2)° in
N4–C9–O1. The thiourea molecule in its thione form
includes C]S and C–N bond lengths [28]. In the crystal,
N–H⋯O hydrogen bonds can be found between the
thiourea and carbonyl groups of the DMF. The DMF mole-
cule forms a hydrogen bond with two N atoms of the
thiourea group [28].
The N–C bonds in Figure 1 differ from one another as
also reported by Li and Hou [28]. They are shorter in com-
parison with the conventional value for an N–C single bond
(
1.479 Å). The adjacent C]S bond length (1.680 (1) Å) is
shorter than the earlier reported C]S distance (1.710 (7) Å)
19], because of the introduced C]O electron-acceptor
group. These distances are similar to those normally found
2 3
Figure 1: Crystalline structure of C16H17Cl N OS.
[
crystalline compound is an isomer of 2-[(2,6-dichloro- in substituted thioureas [23,29]. Intramolecular and inter-
phenyl) methyl]-N-piperidin-1-yl-1,3-thiazole 4-carboxa- molecular N−H⋯O hydrogen bonds occur between the
mide. The difference between it and the isomer is the thiourea N−H atoms and carbonyl-O atom of the DMF sol-
positioning of the chloro group [22].
vate molecule, which also has a hydrogen bond between
the two N atoms of the thiourea groups (2.880 (2) and
2.8802 (2); Figure 2, Table S6) [28].
The solid-state crystal packing and intermolecular
3.2 Interpretation of significant thiourea
interactions are shown in Figure 2. The C H Cl N OS
1
6
17
2 3
DMF solvate
molecules are structured and held together with the
help of intermolecular N–H⋯O hydrogen bonding with
an average distance of 2.880 (2) Å. Their a, b and c axes
are shown in Figure 2. The C H Cl N OS molecules are
Single-crystal X-ray diffraction method was used to determine
and confirm the structure of the synthesized C H Cl N OS
16
17
2 3
1
6
17
2 3
compound. In the compound, two Cl atoms are coplanar
with the C2–C7 and C11–C10 rings, respectively [23,24].
The C8–C2–N2–O1 and C14–C11–N3–O1 torsion angles are
set up by aromatic ring. Inside the thiourea moiety, the
geometry of C1 atom is preferably planar with a sum of
bond angle of 490 (2). Result varies from bond angle
reported by Binzet et al. [25], probably due to hydrogen
bonding [25]. The S1 atom is out of the plane of the
N–C–N thiourea. The thiourea moiety is almost vertical
to two benzene rings [24].
arranged and structured with the assistance of N–H⋯O
hydrogen bonding, with an average distance of 2.841 Å,
which is in the expected range, reported for analogues’
compounds, that is, 2.87 Å [16,26].
The packing contains parallel networks formed by
intermolecular bonding [27]. The crystal packing is inter-
molecular hydrogen bonding through N(3)⋯H(3)⋯O(1)
and intramolecular hydrogen bonding through N(2)⋯H(2)
⋯
O(1), where the two-dimensional hydrogen bonding net-
work could be observed. The NH group of C H Cl N OS
16
17
2 3
The geometry around the nitrogen atom is distorted
and cannot be estimated on hybridization origin. The
distortion can simply be drawn by the contribution of
lone pair of electrons on nitrogen in the delocalization
phenomenon with the π electrons of C]S moiety [26].
The bond distances of C1–N2 (1.357 Å) and C1–N3 (1.360 Å)
ligand was arranged to enable the formation of intra- and
intermolecular hydrogen bonds, which entails the two
chloro atoms as acceptors [27].
are shorter than the average C–N single-bond distance 3.3 Crystal packing
1.499 Å) and likewise that of C]S bond distance (1.680 Å)
is longer than the average distance (1.599 Å) as stated in The crystal packing for C H Cl N OS in a, b and c axes is
(
1
6
17
2 3
literature [26,27]. The elongation of C]S bond might be shown in Figure 2.

Synthesis and crystal structure of C16
H
2
17Cl N
3
OS

515
Figure 2: (a) Crystalline structure of C16
2 3 2 3
H17Cl N OS along a axis. (b) Crystalline structure of C16H17Cl N OS along b axis. (c) Crystalline
structure of C16 17Cl OS along c axis.
H
2 3
N

516
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Ayodele T. Odularu et al.
4
Conclusion and future direction
[4] Stefanska J, Szulczyk D, Koziol AE, Miroslaw B, Kedzierska E,
Fidecka S, et al. Disubstituted thiourea derivatives and their
activity on CNS: synthesis and biological evaluation. Eur J Med
Chem. 2012;55:205–13. doi: 10.1016/j.ejmech.2012.07.020.
Characterization technique of single crystal diffraction
confirmed the crystalline structure of N,N′-bis(4-chloro-
penyl)thiourea N,N-DMF.
[
5] Zhang H, Li R, Zou H. Synthesis and characterization of
thiourea. Pol J Chem Tech. 2019;21(3):35–9. doi: 10.2478/pjct-
2019-0027.
Acknowledgements: The authors thank Govan Mbeki [6] Milosavljević MM, Vukićević Drmanić SŽ, Nikolić JB,
Research and Development Centre (GMRDC) for financial
support. They also express their further appreciation to
Marinković AD, Krstić SS, Petrović SD. Simple one-pot synth-
esis of thioureas from amines, carbon disulfide and oxidants
in water. J Serb Chem Soc. 2016;81(3):219–231. doi: 10.2298/
JSC150831087M.
Michal Dušek and Monica Kučerakova for their contributions.
[
7] Odularu AT, Ajibade PA. Dithiocarbamates: challenges, con-
trol, and approaches to excellent yield, characterization, and
their biological applications. Bioinorg Chem Appl.
Funding information: Financial support was by Govan
Mbeki Research and Development Centre (GMRDC).
2019;2019(8260496):1–15. doi: 10.1155/2019/8260496.
[
8] Bissantz C, Kuhn B, Stahl M. A medicinal chemist’s guide to
molecular interactions. J Med Chem. 2010;53(14):5061–84.
doi: 10.1021/jm100112j.
Author contributions: A.T.O. conceptualized the study,
collected the data, wrote the paper, revised the paper
and approved the final version to be published. P.A.A. [9] Scheiner S. Assessment of the presence and strength of
supervised, acquired funding, and approved the final
version to be published. O.O.O. provided resources and
approved the final version to be published. J. Z. M. provided
resources and approved the final version to be published.
H.P. did the data analyses, data interpretation, and
approved the final to be published.
H-bonds by means of corrected NMR. Molecules.
016;21(11):1426. doi: 10.3390/molecules21111426.
10] Azizi N, Khajeh-Amiri A, Ghafuri H, Bolourtchian M. Toward a
practical and waste-free synthesis of thioureas in water.
Mol Divers. 2011;15:157–61. doi: 10.1007/s11030-010-9236-7.
11] Maddani MR, Prabhu KR. A concise synthesis of substituted
thiourea derivatives in aqueous medium. J Org Chem.
2
[
[
[
2010;75(5):2327–32. doi: 10.1021/jo1001593.
12] Modec B, Podjed N, Lah N. Beyond the simple copper(II)
coordination chemistry with quinaldinate and secondary
amines. Molecules. 2020;25(1573):1–24. doi: 10.3390/
molecules25071573.
Conflict of interest: The authors declare no conflict of
interest.
Data availability statement: All data generated and ana- [13] Vergentev T, Bronwald I, Chernyshov D, Gorfman S,
lysed during this study are included in this published
Ryding SHM, Thompson P, et al. A rapid two-dimensional data
collection system for the study of ferroelectric materials under
external applied electric fields. J Appl Cryst. 2016;49:1501–7.
doi: 10.1107/S1600576716011341.
article (and its supplementary information files).,
Supplementary materials: Supplementary data and fig-
ures for this study are available from the International
Union of Crystallography (IUCr) electronic archives
[
14] Dolomanov OV, Bourhis LJ, Gildea RJ, Howard JAK,
Puschmann H. OLEX2: a complete structure solution, refine-
ment and analysis program. J Appl Cryst. 2009;42:339–41. doi:
10.1107/S0021889808042726.
(
Reference: CCDC 1579588).
[
15] Ghorab MM, Al-Said MS, Ghabbour HA, Chantrapromma S,
Fund HF. (E)-4-Amino-N-(1,2-dihydropyridin-2-yl-idene)ben-
zenesulfonamide nitromethane monosolvate. Acta Cryst Sect E
Struct Rep. 2012;E68(o1030):S1–7. doi: 10.1107/
S1600536812009865.
16] Allen FH, Kennard O, Watson DG, Brammer L, Orpen AG,
Taylor R. Tables of bond lengths determined by X-ray and
neutron diffraction. Part 1. Bond lengths in organic com-
pounds. J Chem Soc Perkin Trans. 1987;2(12):S1–19. doi:
10.1039/P298700000S1.
References
[
[
[
[
1] Jambi SMS. Characterization and synthesis of novel thiourea
derivatives. Int J Chem Tech Res. 2019;12(3):177–87.
doi: 10.20902/IJCTR.2019.120325.
2] Das C, Zhang H, Li R, Zou H. Synthesis and characterization of
thiourea. Pol J Chem Tech. 2019;21(3):35–9. doi: 10.2478/pjct- [17] Rauf MK, Yaseen S, Ebihara M, Badshah A. 1-(2-Chloro-
2
019-0027.
benzo-yl)-3-(pyrimidin-2-yl)thio-urea. Acta Cryst Sect E
Struct Rep Online. 2013;69(o84):1–7. doi: 10.1107/
S1600536812050118.
3] Ghorab MM, El-Gaby MSA, Alsaid MS, Elshaier YAMM,
Soliman AM, El-Senduny FF, et al. Novel thiourea derivatives
bearing sulfonamide moiety as anticancer agents through
COX-2 Inhibition. Anti-Cancer Agents Med Chem.
[18] Saeed A, Qamar R, Fattah TA, Flörke U, Erben MF. Recent devel-
opments in chemistry, coordination, structure and biological
aspects of 1-(acyl/aroyl)-3-(substituted) thioureas. Res Chem
Intermed. 2017;43:3053–93. doi: 10.1007/s11164-016-2811-5.
2
017;17(10):1411–25. doi: 10.2174/
1
871520617666170327153735.

Synthesis and crystal structure of C16
H17Cl
2
3
N OS

517
[
19] Bailey PJ, Grant KJ, Parsons S. Bis[(S)-(-)-methylbenzyl]
thiourea. Acta Cryst. 1997;C53:247–8. doi: 10.1107/
S010827019601298X.
and their nickel and copper complexes. J Chem.
2013;2013:1–9. doi: 10.1155/2013/536562.
[25] Gumus I, Solmaz U, Binzet G, Keskin E, Arslan B, Arslan H.
Supramolecular self-assembly of new thiourea derivatives
directed by intermolecular hydrogen bonds and weak
interactions: crystal structures and Hirshfeld surface analysis. Res
Chem Intermed. 2019;45:169–98. doi: 10.1007/s11164-018-
3596-5.
[26] Altaf AA, Shahzad A, Gul Z, Khan SA, Badshah A, Tahir MN,
et al. Synthesis, crystal structure, and DFT calculations of
1,3-diisobutyl thiourea. J Chem. 2015;2015:1–5. doi: 10.1155/
2015/913435.
[27] Ajibade PA, Zulu NH. Metal complexes of diisopropylthiourea:
synthesis, characterization and antibacterial studies. Int J Mol
Sci. 2011;12(10):7186–98. doi: 10.3390/ijms12107186.
[28] Li M, Hou D. 1-(2,6-Dichlorobenzoyl)-3-(3-nitrophenyl)
thiourea dimethylformamide solvate. Acta Cryst Sect E Struct
Rep Online. 2010;66(o280):1–10. doi: 10.1107/
S1600536809055056.
[29] Pilz SK, Mohr F. On the reactivity of thiourea derivatives with
silver(I) oxide. Eur J Inorg Chem. 2020;2020(23):2285–94.
doi: 10.1002/ejic.202000308.
[
20] Sheldrick GM. SHELXT-integrated space-group and crystal-
structure determination. Acta Cryst. 2015;A71:3–8.
doi: 10.1107/S2053273314026370.
[
21] Rigaku Oxford Diffraction. CrysAlisPro Software System,
Version 1.171. Oxford, UK: Rigaku Corporation; 2015.
22] PubChem [Internet]. Bethesda (MD): National Library of
Medicine (US), National Center for Biotechnology Information;
[
2
2
004. PubChem Compound Summary for CID 2743928; [cited
021 Mar. 28]. Available from. https://pubchem.ncbi.nlm.nih.
gov/compound/2743928
[
23] Moloto N, Revaprasadu N, Moloto MJ, O’Brien P, Raftery J.
N,N’-diisopropylthiourea and N,N′-dicyclohexylthiourea
zinc(II) complexes as precursors for the synthesis of ZnS
nanoparticles. S Afr J Sci. [Internet]. 2009 Aug [cited 2021 Mar
2
8];105(7–8):258–63. Available from: http://www.scielo.org.
za/scielo.php?script=sci_arttext&pid=
S003823532009000400010&lng=en
[24] Binzet G, Kavak G, Külcü G, Özbey U, Flörke U, Arslan H.
Synthesis and characterization of novel thiourea derivatives