1,1′-(Propane-1,3-di­yl)bis­[3-(4-chloro­phen­yl)thio­urea]

Kama, A.B.; Mbodj, M.; Balde, M.G.; Samb, I.; Jeanneau, E.

doi:10.1107/S2414314626011168

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 11| November 2026| x261116

https://doi.org/10.1107/S2414314626011168

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1,1′-(Propane-1,3-diyl)bis[3-(4-chlorophenyl)thiourea]

Antoine Blaise Kama,^a ^* Mamadou Mbodj,^b Mamadou Gallo Balde,^a Issa Samb ^b and Erwann Jeanneau ^c

^aUniversité Alioune Diop de Bambey, UFR Sciences Appliquées et Technologies de l'information et de la communication (SATIC), Equipe Chimie des Matériaux Inorganiques et Organiques (ECMIO), Senegal, ^bUniversité Alioune Diop de Bambey, UFR Sciences Appliquées et Technologies de l'information et de la communication (SATIC), Equipe Chimie Organique Therapeutique (ECOT), Senegal, and ^cCentre de Diffractométrie Henrie Longchambon, Univ. Claude Bernard Lyon 1, 43 Bd 11 Novembre 1918, F-69622 Villeurbanne, France
^*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 21 September 2026; accepted 27 October 2026; online 6 November 2026)

The title compound, C₁₇H₁₈C_l2N₄S₂, crystallizes in the monoclinic space group I2/a with one molecule in the asymmetric unit. In the molecule, two 1-(4-chlorophenyl)thiourea entities are bridged by a propyl fragment. The thiourea entities are inclined relative to the propyl group in different ways, as shown by the C—C—C—N torsion angles of −71.23 (13) and −179.50 (10)°. In the crystal, N—H⋯S hydrogen bonds lead to the formation of supramolecular layers parallel to (001).

Keywords: crystal structure; thiocarbamide; thiourea derivative; N—H⋯S hydrogen-bonding.

CCDC reference: 2598518

Structure description

The thiourea moiety is an important pharmacophore for developing new drug prototypes with biological activities including anti-inflammatory, anticancer, antifungal properties (Ölmez & Waseer, 2020 ; Aguiar et al., 2011 ; Keche & Kamble, 2014 ; Abbas et al., 2020 ). A recent study reported the antimycobactarial and anti-inflammatory activities of thiourea derivatives in the treatment for severe pulmonary tuberculosis (Calixto et al., 2022 ). Taking into account the presence of a chlorophenyl group in some antimicrobial compounds, we prepared the title thiourea derivative, C₁₇H₁₈C_l2N₄S₂, and report here its crystal and molecular structure.

The asymmetric unit comprises one molecule (Fig. 1). This consists of two 1-(4-chlorophenyl)thiourea entities bridged by a propyl fragment. The arrangement of the thiourea fragments relative to the propyl fragment is markedly different, as can be seen from the torsion angles of N2—C8—C9—C10 = −71.23 (13)° and N3—C10—C9—C8 = −179.50 (10)°. The dihedral angles between the thiourea fragments and the attached phenyl ring are virtually identical [61.91 (6)° for thiourea group containing S2 and the C1–C6 ring; 61.97 (6)° for S3-thiourea group and the C12–C17 ring]; the thiourea fragments are inclined to each other by a dihedral angle of 71.37 (6)°, and the phenyl rings by 66.91 (6)°.

Figure 1
Molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level.

Two adjacent molecules form a centrosymmetric dimer (Fig. 2) via pairwise N—H⋯S hydrogen bonds (entry #3 in Table 1) with an R₂²(16) graph-set motif (Etter et al., 1990 ). These dimers are further connected through somewhat weaker hydrogen bonds (entries 1 and 2 in Table 1), resulting in sheets propagating parallel to (001), Fig. 3. The fourth NH group (N4—H4) does not participate in hydrogen bonding.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯S2ⁱ	0.88	2.89	3.4950 (11)	128
N2—H2⋯S3ⁱⁱ	0.88	2.70	3.5386 (10)	161
N3—H3⋯S2ⁱⁱⁱ	0.88	2.51	3.2827 (10)	147
Symmetry codes: (i) ; (ii) $[-x+{\script{3\over 2}}, y, -z+1]$ ; (iii) .

Figure 2
Formation of a centrosymmetric N—H⋯S hydrogen-bonded dimer with graph-set motif R₂²(16); hydrogen bonds (entry 3 in Table 1

) are shown as blue dashed lines.

Figure 3
The packing of molecules in the crystal in a projection along [010]. N—H⋯S hydrogen-bonding interactions are shown as blue dashed lines (entry 3 in Table 1

) and red dashed lines (entry 2 in Table 1

Synthesis and crystallization

A 3 mmol sample of 4-chlorophenyl isothiocyanate was dissolved in 20 ml of ethanol. This solution was added to a 250 ml flask containing 1,2 diaminopropane (3 mmol). The resulting mixture was stirred at room temperature for one h producing a clear solution. Slow evaporation over the course of weeks produced colourless single-crystals suitable for X-ray diffraction studies.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₇H₁₈Cl₂N₄S₂
M_r	413.37
Crystal system, space group	Monoclinic, I2/a
Temperature (K)	100
a, b, c (Å)	17.7563 (2), 5.4972 (1), 38.2124 (5)
β (°)	92.168 (1)
V (Å³)	3727.24 (9)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.58
Crystal size (mm)	0.22 × 0.21 × 0.05

Data collection
Diffractometer	XtaLAB Synergy, Dualflex, HyPix-Arc 100
Absorption correction	Multi-scan (CrysAlis PRO; Rigaku OD, 2022 )
T_min, T_max	0.906, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	54093, 5080, 4601
R_int	0.031
(sin θ/λ)_max (Å⁻¹)	0.710

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.029, 0.076, 1.03
No. of reflections	5080
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.35
Computer programs: CrysAlis PRO (Rigaku OD, 2022), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ) and publCIF (Westrip, 2010 ).

Structural data

CCDC reference: 2598518

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314626011168/wm4261sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626011168/wm4261Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626011168/wm4261Isup3.cml

checkCIF report

Computing details top

1,1'-(Propane-1,3-diyl)bis[3-(4-chlorophenyl)thiourea] top

Crystal data top

C₁₇H₁₈Cl₂N₄S₂	F(000) = 1712
M_r = 413.37	D_x = 1.473 Mg m⁻³
Monoclinic, I2/a	Mo Kα radiation, λ = 0.71073 Å
a = 17.7563 (2) Å	Cell parameters from 37150 reflections
b = 5.4972 (1) Å	θ = 5.4–30.3°
c = 38.2124 (5) Å	µ = 0.58 mm⁻¹
β = 92.168 (1)°	T = 100 K
V = 3727.24 (9) Å³	Plate, colourless
Z = 8	0.22 × 0.21 × 0.05 mm

Data collection top

XtaLAB Synergy, Dualflex, HyPix-Arc 100 diffractometer	5080 independent reflections
Radiation source: micro-focus sealed X-ray tube, PhotonJet (Mo) X-ray Source	4601 reflections with I > 2σ(I)
Mirror monochromator	R_int = 0.031
Detector resolution: 10.0000 pixels mm^-1	θ_max = 30.3°, θ_min = 5.3°
ω scans	h = −22→24
Absorption correction: multi-scan (CrysAlisPro; Rigaku OD, 2022)	k = −7→7
T_min = 0.906, T_max = 1.000	l = −53→53
54093 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.029	H-atom parameters constrained
wR(F²) = 0.076	w = 1/[σ²(F_o²) + (0.038P)² + 4.1233P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max = 0.003
5080 reflections	Δρ_max = 0.36 e Å⁻³
226 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. N-bound hydrogen atoms were discernible from difference-Fourier maps and were modelled with a fixed N—H distance of 0.88 Å and U_iso(H) = 1.2U_eq(N).

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

	x	y	z	U_iso*/U_eq
Cl1	0.44228 (2)	1.28574 (8)	0.73158 (2)	0.03525 (10)
Cl4	0.80672 (2)	−0.08518 (7)	0.28692 (2)	0.03111 (9)
S2	0.52537 (2)	1.48529 (5)	0.56514 (2)	0.01720 (7)
S3	0.78472 (2)	0.62155 (5)	0.42899 (2)	0.01515 (7)
N1	0.57320 (6)	1.06881 (19)	0.59471 (3)	0.0203 (2)
H1	0.594183	0.924784	0.592614	0.024*
N2	0.61224 (6)	1.13321 (18)	0.53974 (3)	0.01702 (19)
H2	0.634429	0.990842	0.542284	0.020*
N3	0.64312 (5)	0.76112 (19)	0.43933 (3)	0.0183 (2)
H3	0.594918	0.753224	0.433186	0.022*
N4	0.65752 (6)	0.5310 (2)	0.39102 (3)	0.0189 (2)
H4	0.608792	0.553998	0.387461	0.023*
C1	0.48211 (7)	1.2199 (3)	0.69173 (3)	0.0248 (3)
C2	0.53671 (8)	1.3750 (3)	0.67922 (3)	0.0255 (3)
H2A	0.553131	1.512301	0.692525	0.031*
C3	0.56700 (7)	1.3262 (2)	0.64691 (3)	0.0230 (2)
H3A	0.604765	1.429330	0.638078	0.028*
C4	0.54168 (7)	1.1251 (2)	0.62754 (3)	0.0192 (2)
C5	0.48772 (8)	0.9711 (3)	0.64054 (4)	0.0259 (3)
H5	0.471032	0.833825	0.627278	0.031*
C6	0.45787 (8)	1.0178 (3)	0.67314 (4)	0.0292 (3)
H6	0.421353	0.911746	0.682391	0.035*
C7	0.57360 (6)	1.2175 (2)	0.56657 (3)	0.0156 (2)
C8	0.62026 (7)	1.2604 (2)	0.50650 (3)	0.0190 (2)
H8A	0.672323	1.323510	0.505360	0.023*
H8B	0.585453	1.401093	0.505448	0.023*
C9	0.60351 (7)	1.0963 (2)	0.47508 (3)	0.0189 (2)
H9A	0.554710	1.013312	0.478154	0.023*
H9B	0.598473	1.197759	0.453719	0.023*
C10	0.66419 (7)	0.9056 (2)	0.46999 (3)	0.0168 (2)
H10A	0.713343	0.985770	0.466688	0.020*
H10B	0.669014	0.799749	0.490918	0.020*
C11	0.69113 (6)	0.6393 (2)	0.41971 (3)	0.0144 (2)
C12	0.69487 (6)	0.3836 (2)	0.36636 (3)	0.0163 (2)
C13	0.69330 (8)	0.4534 (2)	0.33133 (3)	0.0221 (2)
H13	0.669108	0.600518	0.324295	0.027*
C14	0.72715 (8)	0.3078 (2)	0.30660 (3)	0.0237 (3)
H14	0.725888	0.353845	0.282618	0.028*
C15	0.76259 (7)	0.0955 (2)	0.31740 (3)	0.0202 (2)
C16	0.76456 (7)	0.0233 (2)	0.35231 (3)	0.0188 (2)
H16	0.789057	−0.123378	0.359314	0.023*
C17	0.73028 (7)	0.1685 (2)	0.37677 (3)	0.0174 (2)
H17	0.730993	0.120824	0.400674	0.021*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.03533 (19)	0.0516 (2)	0.01934 (15)	0.01032 (16)	0.00848 (12)	−0.00351 (14)
Cl4	0.0425 (2)	0.03006 (17)	0.02166 (15)	0.00403 (14)	0.01338 (13)	−0.00732 (12)
S2	0.01332 (13)	0.01440 (13)	0.02396 (14)	0.00229 (9)	0.00182 (10)	−0.00305 (10)
S3	0.01252 (13)	0.01588 (13)	0.01699 (13)	0.00161 (9)	−0.00012 (9)	−0.00183 (10)
N1	0.0269 (5)	0.0147 (5)	0.0196 (5)	0.0057 (4)	0.0073 (4)	−0.0015 (4)
N2	0.0194 (5)	0.0140 (4)	0.0178 (4)	0.0039 (4)	0.0023 (4)	−0.0024 (4)
N3	0.0123 (4)	0.0223 (5)	0.0202 (5)	0.0002 (4)	0.0007 (3)	−0.0079 (4)
N4	0.0137 (4)	0.0220 (5)	0.0207 (5)	0.0027 (4)	−0.0018 (4)	−0.0083 (4)
C1	0.0244 (6)	0.0327 (7)	0.0176 (5)	0.0095 (5)	0.0048 (4)	−0.0019 (5)
C2	0.0306 (7)	0.0247 (6)	0.0212 (6)	0.0031 (5)	0.0012 (5)	−0.0062 (5)
C3	0.0250 (6)	0.0213 (6)	0.0229 (6)	−0.0005 (5)	0.0049 (5)	−0.0024 (5)
C4	0.0210 (6)	0.0182 (5)	0.0187 (5)	0.0054 (4)	0.0047 (4)	−0.0016 (4)
C5	0.0293 (7)	0.0236 (6)	0.0252 (6)	−0.0032 (5)	0.0071 (5)	−0.0050 (5)
C6	0.0284 (7)	0.0320 (7)	0.0280 (7)	−0.0038 (6)	0.0103 (5)	−0.0009 (6)
C7	0.0124 (5)	0.0149 (5)	0.0194 (5)	−0.0009 (4)	0.0003 (4)	−0.0039 (4)
C8	0.0243 (6)	0.0160 (5)	0.0168 (5)	0.0024 (4)	0.0028 (4)	−0.0023 (4)
C9	0.0192 (5)	0.0195 (6)	0.0179 (5)	0.0052 (4)	0.0005 (4)	−0.0034 (4)
C10	0.0160 (5)	0.0179 (5)	0.0165 (5)	0.0025 (4)	0.0006 (4)	−0.0047 (4)
C11	0.0154 (5)	0.0122 (5)	0.0155 (5)	−0.0004 (4)	0.0014 (4)	−0.0007 (4)
C12	0.0153 (5)	0.0166 (5)	0.0168 (5)	−0.0005 (4)	−0.0001 (4)	−0.0046 (4)
C13	0.0289 (6)	0.0181 (6)	0.0189 (5)	0.0029 (5)	−0.0040 (5)	−0.0010 (5)
C14	0.0349 (7)	0.0223 (6)	0.0139 (5)	−0.0008 (5)	0.0004 (5)	0.0001 (5)
C15	0.0246 (6)	0.0203 (6)	0.0162 (5)	−0.0016 (5)	0.0058 (4)	−0.0054 (4)
C16	0.0222 (6)	0.0165 (5)	0.0178 (5)	0.0016 (4)	0.0024 (4)	−0.0015 (4)
C17	0.0216 (5)	0.0165 (5)	0.0144 (5)	−0.0011 (4)	0.0023 (4)	−0.0011 (4)

Geometric parameters (Å, º) top

Cl1—C1	1.7410 (12)	C4—C5	1.3847 (18)
Cl4—C15	1.7396 (12)	C5—H5	0.9500
S2—C7	1.7029 (12)	C5—C6	1.3961 (18)
S3—C11	1.6889 (11)	C6—H6	0.9500
N1—H1	0.8800	C8—H8A	0.9900
N1—C4	1.4269 (15)	C8—H8B	0.9900
N1—C7	1.3510 (16)	C8—C9	1.5222 (16)
N2—H2	0.8800	C9—H9A	0.9900
N2—C7	1.3380 (14)	C9—H9B	0.9900
N2—C8	1.4613 (15)	C9—C10	1.5210 (16)
N3—H3	0.8800	C10—H10A	0.9900
N3—C10	1.4529 (14)	C10—H10B	0.9900
N3—C11	1.3363 (15)	C12—C13	1.3916 (17)
N4—H4	0.8800	C12—C17	1.3904 (17)
N4—C11	1.3647 (14)	C13—H13	0.9500
N4—C12	1.4252 (14)	C13—C14	1.3921 (18)
C1—C2	1.389 (2)	C14—H14	0.9500
C1—C6	1.379 (2)	C14—C15	1.3817 (18)
C2—H2A	0.9500	C15—C16	1.3912 (16)
C2—C3	1.3910 (17)	C16—H16	0.9500
C3—H3A	0.9500	C16—C17	1.3868 (16)
C3—C4	1.3950 (18)	C17—H17	0.9500

C4—N1—H1	117.2	H8A—C8—H8B	107.9
C7—N1—H1	117.2	C9—C8—H8A	109.1
C7—N1—C4	125.63 (10)	C9—C8—H8B	109.1
C7—N2—H2	117.6	C8—C9—H9A	109.0
C7—N2—C8	124.76 (10)	C8—C9—H9B	109.0
C8—N2—H2	117.6	H9A—C9—H9B	107.8
C10—N3—H3	117.4	C10—C9—C8	113.01 (10)
C11—N3—H3	117.4	C10—C9—H9A	109.0
C11—N3—C10	125.19 (10)	C10—C9—H9B	109.0
C11—N4—H4	117.3	N3—C10—C9	108.53 (9)
C11—N4—C12	125.37 (10)	N3—C10—H10A	110.0
C12—N4—H4	117.3	N3—C10—H10B	110.0
C2—C1—Cl1	119.04 (11)	C9—C10—H10A	110.0
C6—C1—Cl1	119.27 (11)	C9—C10—H10B	110.0
C6—C1—C2	121.68 (12)	H10A—C10—H10B	108.4
C1—C2—H2A	120.5	N3—C11—S3	123.67 (9)
C1—C2—C3	119.04 (12)	N3—C11—N4	113.61 (10)
C3—C2—H2A	120.5	N4—C11—S3	122.71 (9)
C2—C3—H3A	120.1	C13—C12—N4	119.11 (11)
C2—C3—C4	119.73 (12)	C17—C12—N4	120.73 (10)
C4—C3—H3A	120.1	C17—C12—C13	120.12 (11)
C3—C4—N1	120.61 (11)	C12—C13—H13	120.0
C5—C4—N1	118.83 (11)	C12—C13—C14	120.09 (12)
C5—C4—C3	120.51 (11)	C14—C13—H13	120.0
C4—C5—H5	120.0	C13—C14—H14	120.5
C4—C5—C6	119.91 (13)	C15—C14—C13	119.09 (11)
C6—C5—H5	120.0	C15—C14—H14	120.5
C1—C6—C5	119.10 (13)	C14—C15—Cl4	119.60 (9)
C1—C6—H6	120.5	C14—C15—C16	121.47 (11)
C5—C6—H6	120.5	C16—C15—Cl4	118.93 (10)
N1—C7—S2	122.06 (9)	C15—C16—H16	120.4
N2—C7—S2	123.13 (9)	C17—C16—C15	119.11 (11)
N2—C7—N1	114.76 (10)	C17—C16—H16	120.4
N2—C8—H8A	109.1	C12—C17—H17	119.9
N2—C8—H8B	109.1	C16—C17—C12	120.13 (11)
N2—C8—C9	112.30 (10)	C16—C17—H17	119.9

Cl1—C1—C2—C3	−178.19 (10)	C7—N2—C8—C9	−131.43 (12)
Cl1—C1—C6—C5	177.41 (11)	C8—N2—C7—S2	2.01 (16)
Cl4—C15—C16—C17	179.18 (9)	C8—N2—C7—N1	179.55 (11)
N1—C4—C5—C6	177.86 (13)	C8—C9—C10—N3	−179.50 (10)
N2—C8—C9—C10	−71.23 (13)	C10—N3—C11—S3	3.56 (17)
N4—C12—C13—C14	−177.76 (12)	C10—N3—C11—N4	−175.89 (11)
N4—C12—C17—C16	178.16 (11)	C11—N3—C10—C9	155.32 (11)
C1—C2—C3—C4	0.7 (2)	C11—N4—C12—C13	−120.63 (13)
C2—C1—C6—C5	−1.5 (2)	C11—N4—C12—C17	61.58 (17)
C2—C3—C4—N1	−178.60 (12)	C12—N4—C11—S3	2.69 (17)
C2—C3—C4—C5	−1.3 (2)	C12—N4—C11—N3	−177.84 (11)
C3—C4—C5—C6	0.5 (2)	C12—C13—C14—C15	−0.5 (2)
C4—N1—C7—S2	−8.03 (17)	C13—C12—C17—C16	0.38 (18)
C4—N1—C7—N2	174.40 (11)	C13—C14—C15—Cl4	−178.75 (10)
C4—C5—C6—C1	0.9 (2)	C13—C14—C15—C16	0.6 (2)
C6—C1—C2—C3	0.7 (2)	C14—C15—C16—C17	−0.15 (19)
C7—N1—C4—C3	−58.55 (18)	C15—C16—C17—C12	−0.33 (18)
C7—N1—C4—C5	124.08 (14)	C17—C12—C13—C14	0.05 (19)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···S2ⁱ	0.88	2.89	3.4950 (11)	128
N2—H2···S3ⁱⁱ	0.88	2.70	3.5386 (10)	161
N3—H3···S2ⁱⁱⁱ	0.88	2.51	3.2827 (10)	147

Symmetry codes: (i) x, y−1, z; (ii) −x+3/2, y, −z+1; (iii) −x+1, −y+2, −z+1.

Acknowledgements

The authors thanks ICSN cristallochimie service (France) for instrumentation use.

Funding information

Funding for this research was provided by: Universié Alioune Diop de Bambey-Ministère de l'Enseignement Supérieur, de la Recherche et de l'Innovation.

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