research communications\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 9| September 2026|
https://doi.org/10.1107/S2056989026007826

Crystal structure and Hirshfeld surface analysis of 4′-chloro-5-oxo-N-phenyl-3-(thio­phen-2-yl)-2,3,4,5-tetra­hydro-[1,1′-biphen­yl]-4-carboxamide monohydrate

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Farid N. Naghiyev,a Victor N. Khrustalev,b,c Elena Yu. Nevskaya,b Mehmet Akkurt,d Jamshid M. Ashurov,e Hamouda Adam Hamoudaf* and İbrahim G. Mamedova

aFaculty of Chemistry, Baku State University, Z. Khalilov str. 23, Az, 1148, Baku, Azerbaijan, bPeoples' Friendship University of Russia (RUDN University), Miklukho-Maklay St. 6, Moscow, 117198, Russian Federation, cN. D. Zelinsky Institute of Organic Chemistry RAS, Leninsky Prosp. 47, Moscow, 119991, Russian Federation, dDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Türkiye, eInstitute of Bioorganic Chemistry, Academy of Sciences of Uzbekistan, M. Ulugbek Str.,83, Tashkent, 100125, Uzbekistan, and fDepartment of Chemistry, Faculty of Science, University of Kordofan, Sudan
*Correspondence e-mail: [email protected]

Edited by X. Hao, Institute of Chemistry, Chinese Academy of Sciences (Received 17 July 2026; accepted 30 July 2026; online 4 August 2026)

The title mol­ecule, C23H18ClNO2S·H2O, has a stable conformation with S(5) and S(6) rings formed by intra­molecular C—H⋯S and C—H⋯O hydrogen bonds. The water mol­ecule and the carboxyl oxygen atom of the main mol­ecule also make an O—H⋯O hydrogen bond. In the crystal, N—H⋯O, O—H⋯Cl, O—H⋯O and C—H⋯O hydrogen bonds connect mol­ecules to form a three-dimensional network. The mol­ecules are further connected by C—H⋯π inter­actions and face-to-face π–π inter­actions into layers parallel to the (001) plane.

CCDC reference: 2577688

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1. Chemical context

Michael addition and aldol condensation reactions play a significant role in carbon–carbon bond formation, providing highly efficient and versatile strategies for the construction of complex mol­ecular frameworks (Naghiyev et al., 2023View full citation; Mamedov & Khalilov, 2025View full citation). These transformations enable the formation of new C—C bonds under relatively mild conditions, often with excellent regio- and stereoselectivity (Safarova et al., 2023View full citation, 2024View full citation; Tüzün et al., 2025View full citation). Owing to these advantages, Michael addition and aldol condensation reactions are widely employed in organic synthesis, particularly in the preparation of pharmaceuticals, natural products, and advanced functional materials (Naghiyev et al., 2022View full citation, 2024View full citation; Karimli et al., 2023View full citation). Among the products accessible through this synthetic approach, highly substituted cyclo­hexenone derivatives have attracted considerable attention owing to their structural diversity, widespread occurrence in both natural and synthetic compounds, and their utility as versatile inter­mediates in organic synthesis (Asgarova et al., 2019View full citation; Abdel-Galil et al., 2022View full citation). In addition to their synthetic importance, selected members of this class have been reported to exhibit a variety of biological activities, making cyclo­hexenone-based frameworks attractive targets in medicinal chemistry (Khan et al., 2021View full citation; Shikhaliyev et al., 2025View full citation). In particular, aryl-substituted cyclo­hexenone carboxamides represent valuable mol­ecular scaffolds for the synthesis of structurally diverse compounds and continue to attract inter­est in synthetic and structural chemistry. The incorporation of aromatic, heteroaromatic, and amide functionalities into the cyclo­hexenone framework further expands the scope for structural diversification and detailed investigations of their mol­ecular and crystal structures (Lakhrissi et al., 2022View full citation; Nosova et al., 2023View full citation). In this context, herein we report the crystal structure and Hirshfeld surface analysis of the title compound, C23H18ClNO2S·H2O (4), as part of our ongoing investigations (Askerov et al., 2020View full citation; Naghiyev et al., 2021View full citation; Khalilov et al., 2011View full citation).

A reaction route for the formation of the title compound 4 is depicted in Fig. 1[link]. The reaction is initiated by the Michael addition of the acetoacetamide 1 to the α,β-unsaturated chalcone 2, leading to the formation of inter­mediate A. Under basic conditions, inter­mediate A undergoes intra­molecular alkyl­ation to form compound 3, which then undergoes an intra­molecular aldol condensation, resulting in the formation of the cyclo­hexane ring. Subsequent dehydration of this inter­mediate leads the corresponding cyclo­hexenone derivative 4.

[Scheme 1]
[Figure 1]
Figure 1
A reaction route for the formation of the title compound 4.

2. Structural commentary

The conformation of the title mol­ecule is stable with the C—H⋯S and C—H⋯O intra­molecular hydrogen bonding, forming S(5) and S(6) rings (Fig. 2[link], Table 1[link]; Bernstein et al., 1995View full citation). Additionally, an Ow1—Hw1A⋯O2 hydrogen bond exists between the water mol­ecule and the main mol­ecule's carboxyl oxygen atom. Each mol­ecule contains two stereogenic (chiral) centres: in the arbitrarily chosen asymmetric unit, C2 and C3 have S and R configurations, respectively. The thiophene ring (S1/C13–C17) is disordered by a 180° rotation over two orientations around the C3—C14 bond in a 0.5:0.5 ratio. The cyclo­hexene ring (C1–C6) is puckered with Cremer & Pople (1975View full citation) puckering parameters QT = 0.4622 (9) Å, θ = 54.10 (11)° and φ = 112.74 (14)°. The r.m.s plane (r.m.s. deviation = 0.005 Å) of the cyclo­hexane ring (C1–C6) subtends dihedral angles of 73.1 (2), 70.72 (5) and 25.34 (4) °, respectively, with the thio­phene (S1/C14–C17), phenyl (C8–C13) and chloro­phenyl (C18–C23) rings. The thio­phene ring subtends angles of 69.5 (2) and 86.6 (2)° with the phenyl and chloro­phenyl rings, respectively. The angle between the phenyl and chloro­phenyl rings is 84.58 (5)°. The bond lengths and angles in the title compound are in good agreement with those in the compounds discussed in the Database survey section.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the major component of the disordered thio­phene ring (S1/C14–C17).
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1⋯Ow1i 0.881 (14) 1.953 (14) 2.8317 (10) 175.2 (12)
Ow1—Hw1A⋯O2 0.84 (2) 1.93 (2) 2.7681 (9) 171 (2)
Ow1—Hw1B⋯Cl1ii 0.83 (2) 2.81 (2) 3.0653 (7) 100 (1)
Ow1—Hw1B⋯O1iii 0.83 (2) 2.07 (2) 2.8908 (9) 172 (2)
C2—H2⋯S1 1.00 2.80 3.1912 (15) 104
C2—H2⋯Ow1i 1.00 2.50 3.3269 (10) 139
C9—H9⋯O2 0.95 2.32 2.9124 (11) 120
C16—H16⋯O2iv 0.95 2.55 3.423 (6) 152
C17′—H17′⋯O2iv 0.95 2.58 3.511 (5) 166
C11—H11⋯Cg1v 0.95 2.91 3.801 (2) 158
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation; (iii) Mathematical equation; (iv) Mathematical equation; (v) Mathematical equation.
[Figure 2]
Figure 2
Mol­ecular structure of the title compound, with atom labelling. Displacement ellipsoids are drawn at the 50% probability level. For clarity, only one component of the disordered thio­phene ring is shown.

3. Supra­molecular features

In the crystal, mol­ecules are linked to form a three-dimensional network via inter­molecular N1—H1⋯Ow1, Ow1—Hw1B⋯Cl1, Ow1—Hw1B⋯O1, C2—H2⋯Ow1, C16—H16⋯O2 and C17′—H17′⋯O2 hydrogen bonds (Figs. 3[link] and 4[link], Table 1[link]). In addition, C—H⋯π inter­actions and face-to-face π–π inter­actions [Cg5⋯Cg5(−x, 2 − y, 1 − z) = 3.9020 (6) Å, slippage = 1.970 Å and Cg5⋯Cg5(1 − x, 2 − y, 1 − z) = 3.5513 (6) Å, slippage = 0.158 Å; where Cg5 is the centroid of the C18–C23 ring of the chloro­phenyl group] connect the mol­ecules, forming layers parallel to the (001) plane (Figs. 5[link] and 6[link], Table 1[link]).

[Figure 3]
Figure 3
A view of the packing along the b-axis direction of the title compound with N—H⋯O, O—H⋯O, O—H⋯Cl and C—H⋯O hydrogen bonds shown as dashed lines. Hydrogen atoms that do not participate in hydrogen bonding are not displayed for clarity.
[Figure 4]
Figure 4
A view of the packing along the c-axis direction of the title compound with N—H⋯O, O—H⋯O, O—H⋯Cl and C—H⋯O hydrogen bonds shown as dashed lines.
[Figure 5]
Figure 5
A view of the packing along the a-axis direction of the title compound with C—H⋯π and π–π inter­actions shown as dashed lines. Hydrogen atoms that do not engage in hydrogen bonding and water mol­ecules are not shown for clarity.
[Figure 6]
Figure 6
A view of the packing along the b-axis direction of the title compound with C—H⋯π and π–π inter­actions shown as dashed lines.

4. Hirshfeld surface analysis

The Hirshfeld surfaces and two-dimensional fingerprint plots were produced using Crystal Explorer 17.5 (Spackman et al., 2021View full citation). Hirshfeld surfaces enable the presentation of inter­molecular inter­actions by indicating short and long contacts, as well as the relative strength of the inter­actions, with different colors and intensities. Fig. 7[link] displays the title compound's three-dimensional Hirshfeld surface plotted over dnorm in the range −0.6301 to +1.6037 a.u. The red patch surrounding O1, O2, Ow1 and Cl1 are caused by the N—H⋯O, O—H⋯Cl, O—H⋯O and C—H⋯O inter­actions (Table 1[link]), which are crucial to the mol­ecular packing of the title mol­ecule.

[Figure 7]
Figure 7
View of the three-dimensional Hirshfeld surface of the title compound plotted over dnorm in the range −0.6301 to +1.6037 a.u.

Fig. 8[link]a shows the overall two-dimensional fingerprint plot for the title compound, while Fig. 8[link]b–e show those that are divided into H⋯H, C⋯H/H⋯C, O⋯H/H⋯O and Cl⋯H/H⋯Cl contacts. Tables 1[link] and 2[link] provide numerical information of the various contacts. The percentage contributions to the Hirshfeld surfaces from the different inter­atomic contacts are as follows: H⋯H (Fig. 8[link]b; 43.2%), C⋯H/H⋯C (Fig. 8[link]c; 22.2%), O⋯H/H⋯O (Fig. 8[link]d; 12.5%) and Cl⋯H/H⋯Cl (Fig. 8[link]e; 9.8%). The C⋯C (4.8%), S⋯H/H⋯S (3.2%), O⋯C/C⋯O (1.3%), N⋯H/H⋯N (1.2%), Cl⋯O/O⋯Cl (0.8%), Cl⋯C/C⋯Cl (0.7%) and O⋯O (0.3%) contacts are additional modest contributions to the Hirshfeld surface.

Table 2
Summary of short inter­atomic contacts (Å)

Contact Distance Symmetry operation
H23⋯C12 2.99 x, 1 + y, z
Cl1⋯Hw1B 2.81 1 − x, 2 − y, 1 − z
H3⋯Cl1 2.83 1 − x, 2 − y, 1 − z
H4A⋯Cl1 2.88 −x, 2 − y, 1 − z
*H16′⋯C8 2.89 −x, 1 − y, 2 − z
*H16⋯H9 2.48 1 − x, 1 − y, 2 − z
O1⋯Hw1B 2.07 1 − x, 1 − y, 1 − z
O2⋯Hw1A 1.93 x, y, z
H19⋯O2 2.75 1 − x, 1 − y, 1 − z
H1⋯Ow1 1.95 −1 + x, y, z
The prefix * indicates a disordered atom.
[Figure 8]
Figure 8
The full two-dimensional fingerprint plots for the title compound, showing (a) all inter­actions, and delineated into (b) H⋯H, (c) C⋯H/H⋯C, (d) O⋯H/H⋯O and (e) Cl⋯H/H⋯Cl inter­actions. The di and de values are the closest inter­nal and external distances (in Å) from given points on the Hirshfeld surface.

5. Database survey

A search of the Cambridge Structural Database (CSD, version 6.00, updated April 2025; Groom et al., 2016View full citation) for the title compound revealed two compounds: 5-oxo-N-phenyl-3-(thio­phen-2-yl)-2,3,4,5-tetra­hydro-1,1′-biphenyl-4-carboxamide (CSD ref code AHEMIN: Aliyeva et al., 2025View full citation) and dimethyl-4′-bromo-3-oxo-5-(thio­phen-2-yl)-3,4,5,6-tetra­hydro­[1,1′-biphen­yl]- 2,4-di­carboxyl­ate (WOMWUU: Naghiyev et al., 2024View full citation). AHEMIN and WOMWUU crystallize in the monoclinic Cc and P2/1c space groups, respectively.

The two mol­ecules in the asymmetric unit of AHEMIN have different carboxamide moiety conformations. Inter­molecular N—H⋯O hydrogen bonds in the crystal connect the mol­ecules into chains that propagate parallel to the c-axis. While there are no π–π inter­actions between the mol­ecules, there are weak C—H⋯π(ring) inter­actions. In WOMWUU, mol­ecules form ribbons in the b-axis direction as a result of inter­molecular C—H⋯S hydrogen bonds with R22(10) ring motifs. van der Waals forces between the ribbons maintain the cohesiveness of the crystal structure, whereas C—H⋯π inter­actions consolidate the ribbon structure. The thio­phene group is disordered by a 180° rotation around one bond.

6. Synthesis and crystallization

A solution of 0.443 g (0.0025 mol) acetoacetanilide and 0.623 g (0.0025 mol) 1-phenyl-3-(thio­phen-2-yl)prop-2-en-1-one (5.10 mmol) in 30 ml ethanol (10 ml) was stirred for 1 h. After that, 3 drops of methyl­piperazine were added to the solution and the mixture was then stirred for 3 h while the course of reaction was monitored by TLC. After the reaction completion, the solvent was removed under reduced pressure and the residue was recrystallized from an ethanol–water mixture (m.p. = 391 K, yield 73%).

1H NMR (300 MHz, acetone-d6, δ, ppm.): 2.22 and 2.72 (d-d, 2H, CH2, 2JH–H = 16.2 Hz, 3JH–H = 8.3 Hz), 3.54 (t-t, 1H, CH, 3JH–H = 8.3 Hz, 3JH–H = 10.3 Hz), 3.78.15 (d, 1H, CH, 3JH–H = 10.3 Hz), 6.59–7.67 (m, 13H, arom. and =CH), 9.56 (s, 1H, NH); 13C NMR (75 MHz, acetone-d6, δ, ppm.): 31.26 (CH), 44.45 (CH2), 52.87 (CH), 119.08 (CHarom.), 119.20 (CHarom.), 120.35 (Carom.), 123.17 (=CH), 127.00 (CHarom.), 128.69 (CHarom.), 129.47 (CHarom.), 130.97 (CHarom.), 132.13 (Carom.), 131.13 (CHarom.), 133.43 (Carom.), 131.90 (CHarom.), 138.36 (Carom.), 147.33 (Cquat..), 167.27 (CO), 194.27 (CO).

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. All C-bound hydrogen atoms were positioned geometrically (C—H = 0.95–1.00 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C). The H atoms of the water mol­ecule and NH group were located from difference-Fourier maps and refined isotopically with dependent isotropic thermal parameters with Uiso(H) = 1.2Ueq(N) and Uiso(H) = 1.5Ueq(O). The thio­phene ring (S1/C13–C17) is disordered by a 180° rotation over two orientations around the C3—C14 bond in a 0.5:0.5 ratio. Using the FLAT command, both components of the disordered thio­phene ring were restricted to the same plane. In addition, the DFIX command was used to restrain the S—C distances S1—C17, S1—C14, S1′—C17′ and S1′—C14 to fix their bond lengths to 1.72 Å. Furthermore, DELU, SIMU and ISOR commands were used in the refinement to restrain the thermal factors of the disordered C15 S1′, C16 C17′, C17 C16′ and C15′ S1components. Using the SADI command, the C—C lengths of the thio­phene rings were pushed to be the same.

Table 3
Experimental details

Crystal data
Chemical formula C23H20ClNO3S
Mr 425.91
Crystal system, space group Triclinic, PMathematical equation
Temperature (K) 100
a, b, c (Å) 7.1577 (3), 11.1279 (4), 13.2067 (5)
α, β, γ (°) 85.412 (1), 87.973 (1), 79.348 (1)
V (Å3) 1030.25 (7)
Z 2
Radiation type Mo Kα
μ (mm−1) 0.31
Crystal size (mm) 0.24 × 0.22 × 0.13
 
Data collection
Diffractometer Bruker D8 QUEST PHOTON-III area detector
Absorption correction Multi-scan (SADABS; Krause et al., 2015View full citation).
Tmin, Tmax 0.707, 0.746
No. of measured, independent and observed [I > 2σ(I)] reflections 29949, 7470, 6538
Rint 0.026
(sin θ/λ)max (Å−1) 0.758
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.033, 0.096, 1.04
No. of reflections 7470
No. of parameters 307
No. of restraints 171
H-atom treatment H atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3) 0.47, −0.32
Computer programs: APEX3 and SAINT (Bruker, 2018View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation), ORTEP-3 for Windows (Farrugia, 2012View full citation) and PLATON (Spek, 2020View full citation).

Supporting information

CCDC reference: 2577688

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026007826/nx2038sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026007826/nx2038Isup2.hkl

checkCIF report


Computing details top

4'-chloro-5-oxo-N-phenyl-3-(thiophen-2-yl)-2,3,4,5-tetrahydro-[1,1'-biphenyl]-4-carboxamide monohydrate top
Crystal data top
C23H20ClNO3SZ = 2
Mr = 425.91F(000) = 444
Triclinic, P1Dx = 1.373 Mg m−3
a = 7.1577 (3) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1279 (4) ÅCell parameters from 9950 reflections
c = 13.2067 (5) Åθ = 2.3–32.6°
α = 85.412 (1)°µ = 0.31 mm−1
β = 87.973 (1)°T = 100 K
γ = 79.348 (1)°Prism, colourless
V = 1030.25 (7) Å30.24 × 0.22 × 0.13 mm
Data collection top
Bruker D8 QUEST PHOTON-III area detector
diffractometer		6538 reflections with I > 2σ(I)
Radiation source: fine-focus sealed X-ray tubeRint = 0.026
φ and ω scansθmax = 32.6°, θmin = 2.3°
Absorption correction: multi-scan
(SADABS; Krause et al., 2015).		h = −10→10
Tmin = 0.707, Tmax = 0.746k = −16→16
29949 measured reflectionsl = −19→19
7470 independent reflections
Refinement top
Refinement on F2Primary atom site location: difference Fourier map
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.033Hydrogen site location: mixed
wR(F2) = 0.096H atoms treated by a mixture of independent and constrained refinement
S = 1.04 w = 1/[σ2(Fo2) + (0.0492P)2 + 0.2767P]
where P = (Fo2 + 2Fc2)/3
7470 reflections(Δ/σ)max = 0.001
307 parametersΔρmax = 0.47 e Å−3
171 restraintsΔρmin = −0.32 e Å−3
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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C10.25524 (13)0.54707 (8)0.56920 (7)0.01765 (15)
C20.23078 (11)0.53684 (7)0.68443 (6)0.01457 (14)
H20.0916690.5568610.7011140.017*
C30.32834 (12)0.62985 (7)0.73273 (6)0.01465 (14)
H30.4682400.6074500.7189730.018*
C40.25951 (12)0.75980 (7)0.68385 (6)0.01542 (14)
H4A0.1262260.7884770.7059860.019*
H4B0.3376350.8156740.7086010.019*
C50.27020 (12)0.76730 (7)0.56990 (6)0.01545 (14)
C60.27143 (14)0.66615 (8)0.51952 (7)0.02000 (16)
H60.2835760.6732740.4475290.024*
C70.30438 (12)0.40503 (7)0.72605 (6)0.01440 (14)
C80.18480 (13)0.21554 (7)0.78940 (7)0.01687 (15)
C90.35133 (14)0.14688 (8)0.83063 (7)0.02207 (17)
H90.4650420.1796720.8278660.026*
C100.34922 (16)0.02935 (9)0.87605 (8)0.02666 (19)
H100.462878−0.0177160.9037140.032*
C110.18444 (17)−0.02001 (9)0.88158 (8)0.0278 (2)
H110.184360−0.0995110.9136810.033*
C120.02000 (17)0.04840 (9)0.83956 (9)0.0293 (2)
H12−0.0933770.0152320.8424510.035*
C130.01940 (14)0.16499 (9)0.79328 (8)0.02353 (18)
H13−0.0938660.2106600.7641020.028*
C140.29646 (15)0.62858 (8)0.84584 (7)0.02117 (17)
S10.07641 (17)0.62692 (14)0.90037 (9)0.0457 (3)0.5
C150.4188 (7)0.6373 (4)0.9170 (4)0.0418 (9)0.5
H150.5484350.6360450.8980300.050*0.5
C160.3628 (7)0.6481 (6)1.0190 (5)0.0381 (10)0.5
H160.4333020.6634711.0747190.046*0.5
C170.1850 (8)0.6312 (7)1.0167 (5)0.0408 (12)0.5
H170.1155410.6212791.0784470.049*0.5
S1'0.46619 (13)0.65996 (9)0.92283 (8)0.02844 (15)0.5
C15'0.1394 (4)0.6163 (4)0.9066 (3)0.0273 (7)0.5
H15'0.0339290.5923770.8772440.033*0.5
C16'0.1295 (7)0.6379 (6)1.0101 (5)0.0316 (8)0.5
H16'0.0245410.6415241.0565130.038*0.5
C17'0.3053 (6)0.6519 (6)1.0255 (4)0.0311 (9)0.5
H17'0.3448760.6576611.0925690.037*0.5
C180.27163 (12)0.88751 (7)0.51432 (7)0.01561 (14)
C190.32883 (13)0.89587 (8)0.41174 (7)0.01929 (16)
H190.3741620.8231190.3785490.023*
C200.32002 (13)1.00903 (8)0.35821 (7)0.02015 (16)
H200.3582671.0141370.2886160.024*
C210.25466 (12)1.11474 (7)0.40751 (7)0.01738 (15)
C220.20179 (13)1.11022 (8)0.50943 (7)0.01900 (16)
H220.1600411.1835030.5424880.023*
C230.21107 (13)0.99627 (8)0.56233 (7)0.01810 (15)
H230.1757090.9920080.6323600.022*
N10.16715 (10)0.33768 (6)0.74663 (6)0.01635 (13)
H10.0502 (19)0.3750 (12)0.7331 (10)0.020*
O10.25246 (12)0.45808 (6)0.51977 (5)0.02515 (15)
O20.47568 (9)0.36629 (6)0.73864 (5)0.01807 (12)
OW10.79944 (9)0.46463 (6)0.69319 (5)0.01883 (12)
HW1A0.697 (2)0.4412 (14)0.7113 (11)0.028*
HW1B0.787 (2)0.4935 (14)0.6336 (12)0.028*
Cl10.24401 (3)1.25584 (2)0.33950 (2)0.02180 (6)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0226 (4)0.0124 (3)0.0183 (4)−0.0035 (3)−0.0030 (3)−0.0012 (3)
C20.0153 (3)0.0109 (3)0.0178 (3)−0.0030 (2)−0.0001 (3)−0.0015 (3)
C30.0160 (3)0.0113 (3)0.0170 (3)−0.0031 (2)−0.0003 (3)−0.0021 (3)
C40.0169 (3)0.0116 (3)0.0181 (3)−0.0028 (3)−0.0004 (3)−0.0026 (3)
C50.0163 (3)0.0116 (3)0.0186 (4)−0.0023 (3)−0.0021 (3)−0.0015 (3)
C60.0312 (4)0.0126 (3)0.0169 (4)−0.0054 (3)−0.0030 (3)−0.0009 (3)
C70.0166 (3)0.0115 (3)0.0156 (3)−0.0037 (3)0.0013 (3)−0.0022 (2)
C80.0216 (4)0.0119 (3)0.0175 (3)−0.0046 (3)0.0040 (3)−0.0021 (3)
C90.0250 (4)0.0155 (4)0.0247 (4)−0.0027 (3)0.0007 (3)0.0014 (3)
C100.0363 (5)0.0165 (4)0.0250 (4)−0.0012 (4)0.0012 (4)0.0026 (3)
C110.0457 (6)0.0146 (4)0.0234 (4)−0.0086 (4)0.0073 (4)−0.0004 (3)
C120.0372 (5)0.0194 (4)0.0342 (5)−0.0146 (4)0.0059 (4)−0.0014 (4)
C130.0250 (4)0.0171 (4)0.0301 (5)−0.0089 (3)0.0025 (3)−0.0010 (3)
C140.0335 (5)0.0130 (3)0.0177 (4)−0.0056 (3)−0.0003 (3)−0.0021 (3)
S10.0633 (7)0.0539 (6)0.0305 (4)−0.0366 (6)0.0265 (5)−0.0197 (4)
C150.056 (2)0.0290 (16)0.0385 (16)−0.0025 (14)−0.0092 (16)−0.0007 (12)
C160.060 (3)0.0246 (13)0.0310 (17)−0.008 (2)−0.0159 (19)0.0009 (11)
C170.058 (3)0.0328 (15)0.0297 (16)−0.006 (2)0.016 (2)0.0002 (12)
S1'0.0355 (4)0.0243 (3)0.0253 (3)−0.0025 (2)−0.0107 (3)−0.0027 (2)
C15'0.0265 (13)0.0261 (10)0.0308 (12)−0.0103 (12)−0.0016 (12)0.0012 (8)
C16'0.041 (2)0.0289 (16)0.0267 (13)−0.0130 (17)0.0071 (15)−0.0024 (10)
C17'0.040 (2)0.0309 (13)0.0195 (11)−0.0014 (17)−0.0011 (14)0.0020 (9)
C180.0157 (3)0.0114 (3)0.0200 (4)−0.0027 (3)−0.0031 (3)−0.0010 (3)
C190.0215 (4)0.0133 (3)0.0230 (4)−0.0032 (3)0.0020 (3)−0.0021 (3)
C200.0217 (4)0.0150 (3)0.0236 (4)−0.0044 (3)0.0031 (3)0.0001 (3)
C210.0141 (3)0.0119 (3)0.0264 (4)−0.0038 (3)−0.0032 (3)0.0013 (3)
C220.0206 (4)0.0115 (3)0.0252 (4)−0.0022 (3)−0.0037 (3)−0.0027 (3)
C230.0216 (4)0.0127 (3)0.0204 (4)−0.0031 (3)−0.0037 (3)−0.0025 (3)
N10.0157 (3)0.0119 (3)0.0216 (3)−0.0037 (2)0.0011 (2)−0.0003 (2)
O10.0433 (4)0.0133 (3)0.0204 (3)−0.0078 (3)−0.0033 (3)−0.0034 (2)
O20.0153 (3)0.0154 (3)0.0232 (3)−0.0030 (2)−0.0006 (2)0.0004 (2)
OW10.0164 (3)0.0183 (3)0.0222 (3)−0.0051 (2)−0.0008 (2)0.0001 (2)
Cl10.01933 (10)0.01286 (9)0.03293 (12)−0.00468 (7)−0.00022 (8)0.00400 (7)
Geometric parameters (Å, º) top
C1—O11.2324 (10)C14—C15'1.379 (4)
C1—C61.4533 (12)C14—S11.7112 (15)
C1—C21.5233 (12)C14—S1'1.7126 (13)
C2—C71.5287 (11)S1—C171.753 (7)
C2—C31.5396 (11)C15—C161.401 (7)
C2—H21.0000C15—H150.9500
C3—C141.5025 (12)C16—C171.323 (6)
C3—C41.5362 (11)C16—H160.9500
C3—H31.0000C17—H170.9500
C4—C51.5005 (12)S1'—C17'1.755 (5)
C4—H4A0.9900C15'—C16'1.404 (8)
C4—H4B0.9900C15'—H15'0.9500
C5—C61.3511 (11)C16'—C17'1.321 (5)
C5—C181.4751 (11)C16'—H16'0.9500
C6—H60.9500C17'—H17'0.9500
C7—O21.2346 (10)C18—C231.4015 (12)
C7—N11.3494 (10)C18—C191.4022 (13)
C8—C91.3942 (13)C19—C201.3859 (12)
C8—C131.3993 (13)C19—H190.9500
C8—N11.4146 (11)C20—C211.3871 (12)
C9—C101.3971 (13)C20—H200.9500
C9—H90.9500C21—C221.3847 (13)
C10—C111.3874 (16)C21—Cl11.7359 (9)
C10—H100.9500C22—C231.3896 (12)
C11—C121.3858 (17)C22—H220.9500
C11—H110.9500C23—H230.9500
C12—C131.3886 (13)N1—H10.880 (13)
C12—H120.9500OW1—HW1A0.845 (15)
C13—H130.9500OW1—HW1B0.827 (16)
C14—C151.328 (4)
O1—C1—C6121.35 (8)C15—C14—C3128.6 (2)
O1—C1—C2120.62 (8)C15'—C14—C3131.85 (19)
C6—C1—C2117.94 (7)C15—C14—S1109.6 (2)
C1—C2—C7109.81 (6)C3—C14—S1121.63 (8)
C1—C2—C3110.89 (7)C15'—C14—S1'107.14 (19)
C7—C2—C3112.27 (7)C3—C14—S1'120.75 (8)
C1—C2—H2107.9C14—S1—C1786.2 (2)
C7—C2—H2107.9C14—C15—C16122.0 (4)
C3—C2—H2107.9C14—C15—H15119.0
C14—C3—C4109.73 (7)C16—C15—H15119.0
C14—C3—C2112.58 (7)C17—C16—C15100.9 (5)
C4—C3—C2110.46 (7)C17—C16—H16129.6
C14—C3—H3108.0C15—C16—H16129.6
C4—C3—H3108.0C16—C17—S1120.5 (5)
C2—C3—H3108.0C16—C17—H17119.7
C5—C4—C3113.34 (7)S1—C17—H17119.7
C5—C4—H4A108.9C14—S1'—C17'88.12 (19)
C3—C4—H4A108.9C14—C15'—C16'122.5 (3)
C5—C4—H4B108.9C14—C15'—H15'118.8
C3—C4—H4B108.9C16'—C15'—H15'118.8
H4A—C4—H4B107.7C17'—C16'—C15'101.3 (5)
C6—C5—C18120.87 (8)C17'—C16'—H16'129.4
C6—C5—C4120.24 (7)C15'—C16'—H16'129.4
C18—C5—C4118.84 (7)C16'—C17'—S1'120.4 (5)
C5—C6—C1123.73 (8)C16'—C17'—H17'119.8
C5—C6—H6118.1S1'—C17'—H17'119.8
C1—C6—H6118.1C23—C18—C19118.45 (8)
O2—C7—N1124.39 (8)C23—C18—C5120.60 (8)
O2—C7—C2121.41 (7)C19—C18—C5120.93 (7)
N1—C7—C2114.20 (7)C20—C19—C18120.78 (8)
C9—C8—C13119.43 (8)C20—C19—H19119.6
C9—C8—N1124.32 (8)C18—C19—H19119.6
C13—C8—N1116.20 (8)C19—C20—C21119.17 (9)
C8—C9—C10119.30 (9)C19—C20—H20120.4
C8—C9—H9120.3C21—C20—H20120.4
C10—C9—H9120.3C22—C21—C20121.71 (8)
C11—C10—C9121.32 (10)C22—C21—Cl1119.59 (7)
C11—C10—H10119.3C20—C21—Cl1118.69 (7)
C9—C10—H10119.3C21—C22—C23118.61 (8)
C12—C11—C10119.00 (9)C21—C22—H22120.7
C12—C11—H11120.5C23—C22—H22120.7
C10—C11—H11120.5C22—C23—C18121.24 (8)
C11—C12—C13120.61 (10)C22—C23—H23119.4
C11—C12—H12119.7C18—C23—H23119.4
C13—C12—H12119.7C7—N1—C8128.77 (7)
C12—C13—C8120.33 (10)C7—N1—H1116.0 (9)
C12—C13—H13119.8C8—N1—H1115.2 (9)
C8—C13—H13119.8HW1A—OW1—HW1B107.1 (14)
O1—C1—C2—C728.70 (11)C4—C3—C14—S1'−88.62 (9)
C6—C1—C2—C7−154.57 (8)C2—C3—C14—S1'147.93 (7)
O1—C1—C2—C3153.36 (8)C15—C14—S1—C17−2.6 (3)
C6—C1—C2—C3−29.90 (11)C3—C14—S1—C17−178.3 (3)
C1—C2—C3—C14176.17 (7)C3—C14—C15—C16172.9 (4)
C7—C2—C3—C14−60.58 (9)S1—C14—C15—C16−2.4 (5)
C1—C2—C3—C453.12 (9)C14—C15—C16—C177.4 (7)
C7—C2—C3—C4176.37 (7)C15—C16—C17—S1−9.5 (7)
C14—C3—C4—C5−174.95 (7)C14—S1—C17—C167.9 (6)
C2—C3—C4—C5−50.26 (9)C15'—C14—S1'—C17'0.2 (3)
C3—C4—C5—C622.67 (11)C3—C14—S1'—C17'174.9 (2)
C3—C4—C5—C18−159.71 (7)C3—C14—C15'—C16'−169.1 (4)
C18—C5—C6—C1−175.02 (8)S1'—C14—C15'—C16'4.8 (5)
C4—C5—C6—C12.54 (14)C14—C15'—C16'—C17'−8.1 (7)
O1—C1—C6—C5178.22 (9)C15'—C16'—C17'—S1'8.0 (7)
C2—C1—C6—C51.51 (14)C14—S1'—C17'—C16'−5.4 (6)
C1—C2—C7—O280.63 (10)C6—C5—C18—C23159.74 (9)
C3—C2—C7—O2−43.22 (11)C4—C5—C18—C23−17.86 (12)
C1—C2—C7—N1−99.20 (8)C6—C5—C18—C19−18.63 (13)
C3—C2—C7—N1136.95 (7)C4—C5—C18—C19163.77 (8)
C13—C8—C9—C10−0.70 (14)C23—C18—C19—C20−2.01 (13)
N1—C8—C9—C10176.37 (9)C5—C18—C19—C20176.40 (8)
C8—C9—C10—C11−0.47 (15)C18—C19—C20—C210.37 (13)
C9—C10—C11—C121.06 (16)C19—C20—C21—C221.40 (13)
C10—C11—C12—C13−0.49 (16)C19—C20—C21—Cl1−179.90 (7)
C11—C12—C13—C8−0.67 (16)C20—C21—C22—C23−1.44 (13)
C9—C8—C13—C121.27 (14)Cl1—C21—C22—C23179.87 (7)
N1—C8—C13—C12−176.04 (9)C21—C22—C23—C18−0.28 (13)
C4—C3—C14—C15−96.7 (3)C19—C18—C23—C221.97 (13)
C2—C3—C14—C15139.8 (3)C5—C18—C23—C22−176.44 (8)
C4—C3—C14—C15'84.6 (3)O2—C7—N1—C83.06 (14)
C2—C3—C14—C15'−38.9 (3)C2—C7—N1—C8−177.12 (8)
C4—C3—C14—S177.99 (10)C9—C8—N1—C78.68 (14)
C2—C3—C14—S1−45.46 (11)C13—C8—N1—C7−174.16 (9)
Hydrogen-bond geometry (Å, º) top
Cg1 is the centroid of the major component of the disordered thiophene ring (S1/C14–C17).
D—H···AD—HH···AD···AD—H···A
N1—H1···Ow1i0.881 (14)1.953 (14)2.8317 (10)175.2 (12)
Ow1—Hw1A···O20.84 (2)1.93 (2)2.7681 (9)171 (2)
Ow1—Hw1B···Cl1ii0.83 (2)2.81 (2)3.0653 (7)100 (1)
Ow1—Hw1B···O1iii0.83 (2)2.07 (2)2.8908 (9)172 (2)
C2—H2···S11.002.803.1912 (15)104
C2—H2···Ow1i1.002.503.3269 (10)139
C9—H9···O20.952.322.9124 (11)120
C16—H16···O2iv0.952.553.423 (6)152
C17′—H17′···O2iv0.952.583.511 (5)166
C11—H11···Cg1v0.952.913.801 (2)158
C11—H11···Cg2v0.952.863.757 (2)158
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y+2, −z+1; (iii) −x+1, −y+1, −z+1; (iv) −x+1, −y+1, −z+2; (v) x, y−1, z.
Summary of short interatomic contacts (Å) top
ContactDistanceSymmetry operation
H23···C122.99x, 1 + y, z
Cl1···Hw1B2.811 - x, 2 - y, 1 - z
H3···Cl12.831 - x, 2 - y, 1 - z
H4A···Cl12.88-x, 2 - y, 1 - z
*H16'···C82.89-x, 1 - y, 2 - z
*H16···H92.481 - x, 1 - y, 2 - z
O1···Hw1B2.071 - x, 1 - y, 1 - z
O2···Hw1A1.93x, y, z
H19···O22.751 - x, 1 - y, 1 - z
H1···Ow11.95-1 + x, y, z
The prefix * indicates a disordered atom.
 

Acknowledgements

Authors' contributions are as follows. Conceptualization, FNN and IGM; methodology, FNN and IGM; investigation, JMA, MA and HAH; writing (original draft), MA and FNN; writing (review and editing of the manuscript), MA and FNN; visualization, MA, EYN and IGM; funding acquisition, VNK, HAH and FNN; resources, EYN, VNK, JMA and FNN; supervision, İGM and MA.

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Volume 82| Part 9| September 2026|
https://doi.org/10.1107/S2056989026007826
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