3-(4-Chloro­phen­yl)-3-hy­droxy-1-phenyl­prop-2-ene-1-thione

Chakravarthy, A.S.J.; Sreenatha, N.R.; Babu, N.

doi:10.1107/S2414314626005638

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 11| Part 6| June 2026| x260563

https://doi.org/10.1107/S2414314626005638

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3-(4-Chlorophenyl)-3-hydroxy-1-phenylprop-2-ene-1-thione

A S Jeevan Chakravarthy,^a ^* N R Sreenatha ^b ^* and Nagesh Babu ^c

^aDepartment of Chemistry, BMS Institute of Technology & Management, Autonomous under Visvesvaraya Technological University, Avalahalli, Yelahanka, Bengaluru, Karnataka 560064, India, ^bDepartment of Physics, Government Engineering College, Bedarapura, Chamarajanagara, Karnataka 571313, India, and ^cDepartment of Biochemistry, Maharani Cluster University, Bangalore 560001, Karnataka, India
^*Correspondence e-mail: [email protected], [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 19 May 2026; accepted 28 May 2026; online 2 June 2026)

In the title compound, C₁₅H₁₁ClOS, the dihedral angle between the aromatic rings is 13.06 (6)° and an intramolecular O—H⋯S hydrogen bond supports the molecular conformation. In the extended structure, weak C—H⋯O hydrogen bonds connect the molecules into [010] chains.

Keywords: chlorophenyl; thioxopropan; dihedral angle; crystal structure.

CCDC reference: 2500235

Structure description

The title compound, C₁₅H₁₁ClOS, adopts a non-planar structure (Fig. 1) defined by the dihedral angle between the mean planes of the C1–C6 and C10–C16 phenyl rings of 13.06 (6)°. The major twist in the molecule occurs about the C9—C10 bond [C8—C9—C10—C15 = −32.1 (2)°] and an intramolecular O—H⋯S hydrogen bond (Table 1) supports the conformation. The bond lengths and bond angles are in good agreement with literature values for similar structures (Ganesha et al. 2023 ; Sreenatha et al. 2018 , 2021 ; Nizamuddin et al. 2025 ; Lakshminarayana et al. 2022 ).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯S1	0.82	2.11	2.8763 (12)	155
C6—H6⋯O1ⁱ	0.93	2.59	3.379 (2)	143
Symmetry code: (i) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ .

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

In the extended structure, weak C—H⋯O hydrogen bonds connect the molecules into C(6) [010] chains (Fig. 2) with adjacent molecules related by glide symmetry.

Figure 2
Packing of the title compound viewed along [100] with hydrogen bonds indicated by black dashed lines.

Synthesis and crystallization

To a stirred suspension of NaH (0.175 g, 2 eq.) in 20 ml of N,N-dimethylformamide (DMF) was added 4-chloroacetophenon (1.00 g, 1 eq.) dropwise and the suspension was stirred at room temperature (Fig. 3). After 1 h, phenyldithioester (0.672 g, 1.1 eq.) dissolved in 20 ml of DMF was added dropwise and the stirring was continued at room temperature. After completion of the reaction (monitored by TLC), it was quenched with saturated aqueous NH₄OH solution (50 ml) extracted with EtOAc (3 × 25 ml), washed with water (3 × 25 ml), brine (25 ml), and dried over anhydrous Na₂SO₄. The combined organic layer was evaporated under vacuum to give the title compound (single spot on TLC), which was passed through a silica gel column for further purification using hexane/EtOAc (9.5:0.5), as eluent. Then, 0.5 g of the title compound was dissolved in 10 ml of DMF and was allowed to undergo slow evaporation (Nagaraju et al. 2020 ). Good quality crystals obtained were isolated and subjected to single-crystal X-ray diffraction studies.

Figure 3
Synthesis scheme for the title compound.

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₁ClOS
M_r	274.75
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	302
a, b, c (Å)	7.2296 (2), 13.8519 (3), 26.0849 (7)
V (Å³)	2612.24 (12)
Z	8
Radiation type	Mo Kα
μ (mm⁻¹)	0.44
Crystal size (mm)	0.28 × 0.25 × 0.23

Data collection
Diffractometer	Bruker SMART CCD
No. of measured, independent and observed [I > 2σ(I)] reflections	90193, 3984, 3197
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.715

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.136, 1.04
No. of reflections	3984
No. of parameters	163
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.27, −0.38
Computer programs: APEX and SAINT (Bruker, 2012 ), SHELXT2014/4 (Sheldrick, 2015a ), SHELXL2019/2 (Sheldrick, 2015b ) and PLATON(Spek, 2020 ).

Structural data

CCDC reference: 2500235

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S2414314626005638/hb4563sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314626005638/hb4563Isup3.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314626005638/hb4563Isup3.cml

checkCIF report

Computing details top

3-(4-Chlorophenyl)-3-hydroxy-1-phenylprop-2-ene-1-thione top

Crystal data top

C₁₅H₁₁ClOS	D_x = 1.397 Mg m⁻³
M_r = 274.75	Mo Kα radiation, λ = 0.71073 Å
Orthorhombic, Pbca	Cell parameters from 90193 reflections
a = 7.2296 (2) Å	θ = 3.0–30.5°
b = 13.8519 (3) Å	µ = 0.44 mm⁻¹
c = 26.0849 (7) Å	T = 302 K
V = 2612.24 (12) Å³	Block, colorless
Z = 8	0.28 × 0.25 × 0.23 mm
F(000) = 1136

Data collection top

Bruker SMART CCD diffractometer	R_int = 0.046
Radiation source: graphite	θ_max = 30.5°, θ_min = 3.0°
ω scans	h = −10→10
90193 measured reflections	k = −19→19
3984 independent reflections	l = −36→36
3197 reflections with I > 2σ(I)

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)] = 0.042	H-atom parameters constrained
wR(F²) = 0.136	w = 1/[σ²(F_o²) + (0.0742P)² + 0.5775P] where P = (F_o² + 2F_c²)/3
S = 1.04	(Δ/σ)_max = 0.001
3984 reflections	Δρ_max = 0.27 e Å⁻³
163 parameters	Δρ_min = −0.38 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. Hydrogen atoms were placed in ideal positions and refined as riding model of C—H = 0.93 Å with U_iso (H) = 1.2U_eq (C) for aromatic H atoms.

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

	x	y	z	U_iso*/U_eq
S1	0.13146 (8)	0.10428 (3)	0.64334 (2)	0.05992 (16)
Cl1	0.32731 (8)	0.49282 (4)	0.92234 (2)	0.06749 (17)
O1	0.12163 (18)	0.16132 (8)	0.74933 (4)	0.0540 (3)
H1	0.108232	0.129925	0.722935	0.081*
C4	0.2303 (2)	0.30758 (10)	0.78307 (5)	0.0388 (3)
C10	0.28603 (18)	0.25950 (10)	0.59518 (5)	0.0376 (3)
C8	0.2416 (2)	0.27248 (10)	0.68877 (5)	0.0395 (3)
H8	0.290559	0.334080	0.684611	0.047*
C3	0.2164 (2)	0.26910 (11)	0.83215 (5)	0.0447 (3)
H3	0.186004	0.204298	0.836171	0.054*
C15	0.2767 (2)	0.35871 (11)	0.58661 (5)	0.0432 (3)
H15	0.227176	0.398827	0.611690	0.052*
C9	0.2216 (2)	0.21652 (10)	0.64414 (5)	0.0393 (3)
C2	0.2469 (2)	0.32550 (12)	0.87512 (6)	0.0486 (3)
H2	0.237457	0.299027	0.907778	0.058*
C7	0.19601 (19)	0.24538 (10)	0.73824 (5)	0.0396 (3)
C11	0.3609 (2)	0.20103 (12)	0.55686 (6)	0.0455 (3)
H11	0.366388	0.134537	0.561551	0.055*
C14	0.3403 (2)	0.39815 (12)	0.54114 (6)	0.0514 (4)
H14	0.331563	0.464328	0.535660	0.062*
C1	0.2911 (2)	0.42091 (12)	0.86880 (6)	0.0464 (3)
C5	0.2752 (3)	0.40477 (11)	0.77817 (6)	0.0576 (4)
H5	0.284178	0.432015	0.745679	0.069*
C12	0.4271 (2)	0.24143 (13)	0.51187 (6)	0.0521 (4)
H12	0.478848	0.201929	0.486868	0.063*
C13	0.4169 (2)	0.33946 (14)	0.50382 (6)	0.0543 (4)
H13	0.461181	0.366107	0.473488	0.065*
C6	0.3067 (3)	0.46137 (12)	0.82081 (7)	0.0624 (5)
H6	0.338160	0.526109	0.817167	0.075*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0890 (3)	0.0388 (2)	0.0519 (3)	−0.01420 (19)	0.0021 (2)	−0.00697 (16)
Cl1	0.0811 (3)	0.0675 (3)	0.0538 (3)	−0.0044 (2)	0.0007 (2)	−0.0245 (2)
O1	0.0793 (8)	0.0396 (5)	0.0432 (5)	−0.0116 (5)	0.0043 (5)	0.0008 (4)
C4	0.0436 (7)	0.0361 (6)	0.0367 (6)	0.0021 (5)	0.0032 (5)	−0.0007 (5)
C10	0.0393 (6)	0.0396 (7)	0.0340 (6)	0.0018 (5)	−0.0037 (5)	−0.0045 (5)
C8	0.0467 (7)	0.0349 (6)	0.0370 (6)	−0.0030 (5)	0.0006 (5)	−0.0018 (5)
C3	0.0541 (8)	0.0412 (7)	0.0388 (7)	−0.0064 (6)	0.0012 (6)	0.0024 (6)
C15	0.0520 (7)	0.0408 (7)	0.0369 (7)	0.0019 (6)	−0.0002 (6)	−0.0036 (5)
C9	0.0430 (7)	0.0361 (6)	0.0387 (7)	0.0015 (5)	−0.0025 (5)	−0.0022 (5)
C2	0.0561 (8)	0.0537 (8)	0.0362 (7)	−0.0054 (7)	0.0015 (6)	0.0004 (6)
C7	0.0445 (7)	0.0356 (6)	0.0387 (7)	0.0012 (5)	0.0004 (5)	−0.0006 (5)
C11	0.0486 (7)	0.0447 (7)	0.0432 (7)	0.0080 (6)	−0.0015 (6)	−0.0083 (6)
C14	0.0619 (9)	0.0472 (8)	0.0450 (8)	−0.0011 (7)	−0.0003 (7)	0.0054 (6)
C1	0.0498 (8)	0.0467 (8)	0.0427 (7)	0.0011 (6)	0.0032 (6)	−0.0104 (6)
C5	0.0960 (13)	0.0371 (7)	0.0396 (7)	−0.0016 (8)	0.0063 (8)	0.0023 (6)
C12	0.0502 (8)	0.0660 (10)	0.0401 (7)	0.0089 (7)	0.0032 (6)	−0.0100 (7)
C13	0.0554 (9)	0.0685 (11)	0.0390 (7)	−0.0003 (8)	0.0043 (6)	0.0041 (7)
C6	0.1009 (14)	0.0359 (7)	0.0503 (9)	−0.0051 (8)	0.0081 (9)	−0.0048 (7)

Geometric parameters (Å, º) top

S1—C9	1.6860 (15)	C15—C14	1.384 (2)
Cl1—C1	1.7353 (15)	C15—H15	0.9300
O1—C7	1.3148 (17)	C2—C1	1.370 (2)
O1—H1	0.8200	C2—H2	0.9300
C4—C5	1.391 (2)	C11—C12	1.385 (2)
C4—C3	1.3904 (19)	C11—H11	0.9300
C4—C7	1.4736 (18)	C14—C13	1.384 (2)
C10—C15	1.3940 (19)	C14—H14	0.9300
C10—C11	1.3959 (19)	C1—C6	1.376 (2)
C10—C9	1.4841 (19)	C5—C6	1.380 (2)
C8—C7	1.3837 (19)	C5—H5	0.9300
C8—C9	1.4060 (18)	C12—C13	1.376 (3)
C8—H8	0.9300	C12—H12	0.9300
C3—C2	1.384 (2)	C13—H13	0.9300
C3—H3	0.9300	C6—H6	0.9300

C7—O1—H1	109.5	O1—C7—C4	114.33 (12)
C5—C4—C3	118.21 (13)	C8—C7—C4	122.77 (12)
C5—C4—C7	122.16 (13)	C12—C11—C10	120.41 (15)
C3—C4—C7	119.63 (12)	C12—C11—H11	119.8
C15—C10—C11	118.42 (14)	C10—C11—H11	119.8
C15—C10—C9	121.22 (12)	C13—C14—C15	120.25 (16)
C11—C10—C9	120.34 (13)	C13—C14—H14	119.9
C7—C8—C9	126.72 (13)	C15—C14—H14	119.9
C7—C8—H8	116.6	C2—C1—C6	121.43 (14)
C9—C8—H8	116.6	C2—C1—Cl1	119.48 (12)
C2—C3—C4	121.18 (14)	C6—C1—Cl1	119.08 (13)
C2—C3—H3	119.4	C6—C5—C4	120.96 (15)
C4—C3—H3	119.4	C6—C5—H5	119.5
C14—C15—C10	120.68 (14)	C4—C5—H5	119.5
C14—C15—H15	119.7	C13—C12—C11	120.63 (14)
C10—C15—H15	119.7	C13—C12—H12	119.7
C8—C9—C10	117.33 (12)	C11—C12—H12	119.7
C8—C9—S1	123.95 (11)	C12—C13—C14	119.59 (15)
C10—C9—S1	118.72 (10)	C12—C13—H13	120.2
C1—C2—C3	118.97 (14)	C14—C13—H13	120.2
C1—C2—H2	120.5	C1—C6—C5	119.24 (15)
C3—C2—H2	120.5	C1—C6—H6	120.4
O1—C7—C8	122.88 (13)	C5—C6—H6	120.4

C5—C4—C3—C2	−0.2 (2)	C5—C4—C7—C8	13.5 (2)
C7—C4—C3—C2	−179.73 (15)	C3—C4—C7—C8	−167.04 (14)
C11—C10—C15—C14	0.0 (2)	C15—C10—C11—C12	1.1 (2)
C9—C10—C15—C14	178.81 (14)	C9—C10—C11—C12	−177.71 (14)
C7—C8—C9—C10	−177.99 (13)	C10—C15—C14—C13	−1.0 (2)
C7—C8—C9—S1	1.4 (2)	C3—C2—C1—C6	−0.4 (3)
C15—C10—C9—C8	−32.1 (2)	C3—C2—C1—Cl1	179.30 (13)
C11—C10—C9—C8	146.74 (14)	C3—C4—C5—C6	0.5 (3)
C15—C10—C9—S1	148.47 (12)	C7—C4—C5—C6	−179.97 (17)
C11—C10—C9—S1	−32.71 (18)	C10—C11—C12—C13	−1.2 (2)
C4—C3—C2—C1	0.1 (2)	C11—C12—C13—C14	0.2 (3)
C9—C8—C7—O1	−1.7 (2)	C15—C14—C13—C12	0.9 (3)
C9—C8—C7—C4	177.02 (14)	C2—C1—C6—C5	0.7 (3)
C5—C4—C7—O1	−167.72 (15)	Cl1—C1—C6—C5	−178.99 (16)
C3—C4—C7—O1	11.8 (2)	C4—C5—C6—C1	−0.8 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···S1	0.82	2.11	2.8763 (12)	155
C6—H6···O1ⁱ	0.93	2.59	3.379 (2)	143

Symmetry code: (i) −x+1/2, y+1/2, z.

Acknowledgements

Authors are thankful to the research centers BMSIT&M, Bengaluru and GEC, Chamarajanagara

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