Synthesis and structure of (RS)-6-hy­droxy-6-(2-oxoprop­yl)-1,10-phenanthrolin-5(6H)-one

Benlatreche, T.; Mezrag, A.; Boualia, B.; Golhen, S.

doi:10.1107/S2056989026004408

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ISSN: 2056-9890

Volume 82| Part 6| June 2026|

https://doi.org/10.1107/S2056989026004408

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Synthesis and structure of (RS)-6-hydroxy-6-(2-oxopropyl)-1,10-phenanthrolin-5(6H)-one

Tarek Benlatreche,^a,^b ^* Abderrahmane Mezrag,^c,^d Boutheina Boualia ^a and Stéphane Golhen ^e

^aEnvironmental and Structural Molecular Chemistry Research Unit, URCHEMS, Faculty of Exact Sciences, University of Constantine 1-Mentouri Brothers, 25000, Algeria, ^bNational Higher School for Hydraulics, Abdellah Arbaoui, Blida, Algeria, ^cResearch Unit Development of Natural Resources, Bioactive Molecules and Physiochemical and Biological Analysis, Department of Chemistry, Constantine 1 University, Constantine 25000, Algeria, ^dFaculty of Science, Department of Organic Chemistry, Saad Dahleb University, Blida 1, Algeria, and ^eCNRS, Rennes Institute of Chemical Sciences -UMR 6226, University of Rennes, France
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 7 April 2026; accepted 25 April 2026; online 7 May 2026)

The title compound, C₁₅H₁₂N₂O₃, was synthesized by reacting phendione with acetone in ethanol under microwave irradiation. An intramolecular C=O⋯π interaction supports the molecular conformation. In the crystal, inversion dimers linked by pairwise, bifurcated O—H⋯(N,N) hydrogen bonds are seen and the dimers are further linked by weak C—H⋯N and C—H⋯O hydrogen bonds and aromatic π–π stacking interactions. Hirshfeld surface analysis shows the following contact percentages: H⋯H 36.8%; H⋯O/O⋯H 26.1%; H⋯C/C⋯H 14.9%; H⋯N/N⋯H 14.5%; C⋯C 5.3%, with all other contact types making negligible contributions.

Keywords: crystal structure; phenanthroline-5,6-dione derivative; O—H⋯N and C—H⋯O hydrogen bonds; Hirshfeld surface analysis.

CCDC reference: 2549869

1. Chemical context

1,10-Phenanthroline-5,6-dione (phendione, C₁₂H₆N₂O₂) is a quinonoid derivative of 1,10-phenanthroline, characterized by the presence of two carbonyl groups at positions 5 and 6 of the aromatic core, which confers both diimine- and quinone-type reactive sites. This dual functionality provides significant versatility in coordination chemistry, allowing it to bind to metal ions primarily through the nitrogen atoms of the diimine moiety (Ermakova et al., 2023 ), while in certain cases also engaging the oxygen atoms of the carbonyl groups in the coordination process (Jing et al., 2011 ).

Phendione and its derivatives have broad applications in biology (Pivetta et al., 2014 ; McCann et al., 2012 ), chemistry, and medicinal chemistry. Their complexes, particularly those formed with Cu^II and Ag^I, exhibit antimicrobial (Galdino et al., 2022 ), antifungal (Granato et al., 2017 ) and antitumor activities (Deegan et al., 2006 ) due to their ability to interact with DNA and disrupt cellular redox processes (Pivetta et al., 2014). They thus target both cancer cells and drug-resistant bacteria, making them promising candidates for the development of new therapeutic agents (Granato et al., 2021 ).

As part of our studies in this area, we now describe the synthesis and structure of the title compound, C₁₅H₁₂N₂O₃ (I). We are particularly interested in this molecule because of its promising biological properties observed in our previous investigations, especially its anticholinesterase and antifungal activities against several tested strains. In addition, this compound exhibits a strong ability to coordinate with metal ions due to the presence of suitable donor atoms in its structure. In our work, special attention is given to its interaction with tin, as organotin derivatives are known to exhibit enhanced biological activities. Therefore, the synthesis and characterization of such complexes are of particular interest, not only to evaluate their potential biological properties, but also to gain deeper insight into the structure–activity relationships. This approach is fully consistent with our research objectives, which focus on the development of new bioactive compounds through coordination chemistry.

2. Structural commentary

Compound (I) crystallizes in the monoclinic space group P2₁/c with one molecule in the asymmetric unit (Fig. 1). The acetone moiety is attached to the aromatic core via atom C13 and adopts an approximately planar conformation, as indicated by the O3—C14—C13—C5 torsion angle of −11.3° (2), which may be associated with an intramolecular C14=O3⋯π interaction with O⋯Cg = 2.7130 (16) Å and C=O⋯π = 98.71 (11)°. The dihedral angle between the acetone group and the phenanthroline ring system is 84.99 (5)°, reflecting an almost perpendicular orientation. Bond lengths in the molecule vary from 1.211 (2) Å (O3—C14) to 1.545 (3) Å (C5—C6), while bond angles range from 107.86 (14)° (O1—C5—C6) to 124.13 (18)° (N2—C10—C9). The molecule features a quasi-planar aromatic core, whereas the carbonyl groups and peripheral substituents adopt moderate distortions to reduce steric interactions, as illustrated by the torsion angles C3—C4—C5—O1 = 58.65 (19)°, C3—C4—C5—C13 = −57.3 (2)°, C12—C4—C5—O1 = −118.38 (16)° and C12—C4—C5—C13 = 125.62 (17)°. Atom C5 is a stereogenic (chiral) centre: in the arbitrarily-chosen asymmetric unit, it has R configuration, but crystal symmetry generates a racemic mixture.

Figure 1
The asymmetric unit of (I) with displacement ellipsoids drawn at the 50% probability level.

3. Supramolecular features

In the extended structure of (I), an asymmetric, bifurcated O1—H1⋯(N1,N2) interaction, with H⋯A distances of 2.22 and 2.56 Å, respectively (sum of angles at H1 = 359°), gives rise to an R₁²(5) ring motif, linking the molecules into inversion dimers (Table 1, Fig. 2). The hydrogen bonds C13—H13A⋯O1 and C15—H15B⋯O1, with H⋯A distances of 2.52 and 2.67 Å, respectively, generate R₂¹ (6) loops connecting adjacent molecules, which propagate along the c-axis direction (Fig. 3). Two R₂²(8) motifs are also observed: the first is formed by C1—H1A⋯O1 and C3—H3⋯N1 (H⋯A = 2.63 and 2.83 Å; Fig. 4), while the second arises from C15—H15A⋯O3 (H⋯A = 2.69 Å; Fig. 3). These motifs repeat along the b and c axes, respectively, contributing to the long-range organization of the crystal. The C8—H8⋯O2 interaction (H⋯A = 2.62 Å) forms an R₂²(10) ring motif linking two neighboring molecules, propagating along the c-axis direction (Fig. 3). Additionally, the C3—H3⋯N1 bond generates C(5) chains extending parallel to the b-axis direction (Fig. 4), further reinforcing the continuity of hydrogen-bonding interactions within the structure.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N1ⁱ	0.84	2.22	2.977 (2)	149
O1—H1⋯N2ⁱ	0.84	2.56	3.262 (2)	142
C13—H13A⋯O1ⁱⁱ	0.99	2.52	3.457 (2)	158
C15—H15B⋯O1ⁱⁱ	0.98	2.67	3.561 (3)	152
C1—H1A⋯O1ⁱⁱⁱ	0.95	2.63	3.302 (2)	128
C3—H3⋯N1ⁱⁱⁱ	0.95	2.83	3.727 (2)	158
C8—H8⋯O2^iv	0.95	2.62	3.436 (3)	145
C10—H10⋯O3^v	0.95	2.59	3.235 (2)	125
C15—H15A⋯O3^vi	0.98	2.69	3.254 (3)	117
Symmetry codes: (i) ; (ii) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) $[-x+1, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iv) ; (v) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ ; (vi) .

Figure 2
Detail of the packing of (I) illustrating the bifurcated O1—H1⋯(N1,N2) hydrogen bonds, which form an inversion dimer.

Figure 3
Detail of the packing of (I) showing the C15—H15B⋯O1, C13—H13A⋯O1, C15—H15A⋯O3 and C8—H8⋯O2 hydrogen bonds, forming different ring motifs.

Figure 4
Crystal packing of (I) illustrating the C1—H1A⋯O1 and C3—H3⋯N1 hydrogen bonds forming a ring motif; and C(5) chains extending parallel to the b-axis direction, respectively.

The three-dimensional architecture is consolidated by aromatic π–π stacking interactions between superposed molecules. The centroid–centroid distances are 3.6098 (12) and 3.4902 (11) Å, observed between the ring centroids Cg1 and Cg2′ [symmetry code: (′) 1 − x, 1 − y, −z], where Cg1 and Cg2 correspond to the N1/C1–C4/C12 and N2/C7–C10/C11 rings, respectively, as well as Cg1 and Cg3′, where Cg3 represents the centroid of the C11/C4–C7/C12 ring (Fig. 5).

Figure 5
Depiction of π–π stacking interactions between the aromatic rings of superposed molecules, with centroid–centroid distances (Cg1⋯Cg2′/Cg1⋯Cg3′) highlighted.

4. Database survey

A search of the Cambridge Structural Database (CSD, version 2025.3.1, update of February 2026; Groom et al., 2016 ) for compounds similar to (I) was undertaken.

Database analysis revealed that the structure of (I) had not been reported previously, although similar structures were identified in monoatomic ruthenium(II), copper(II), and tin(IV) complexes. These structures, with CSD refcodes ATOPUU (Fujihara et al., 2004 ), RUZQEJ (Karnahl et al., 2010 ) and TILQOY (Benlatreche, 2023 ), crystallize in space groups C2/c, P $[\overline{1}]$ and Pna2₁, respectively. Furthermore, another ligand, formed in a distinct complex (JIVPOX; Golubeva et al., 2023 ), exhibits a structure similar to our molecule, with the difference that the acetone group is replaced by an ethoxy group. This complex crystallizes in space group P $[\overline{1}]$ .

5. Hirshfeld surface analysis

In order to further quantify the intermolecular interactions contributing to the organization of the crystal packing, a Hirshfeld surface (HS) analysis, accompanied by an analysis of the associated two-dimensional fingerprint plots (FP), was carried out using CrystalExplorer 21.5 (Spackman et al., 2021 ).

The Hirshfeld d_norm surfaces were mapped over the range −0.41 to 1.36 Å using a fixed colour scale from 0.76 (red) to 2.4 (blue). The Hirshfeld surface was further investigated through the associated two-dimensional fingerprint plots, which provide a quantitative representation of the intermolecular contacts within the crystal structure. As shown in Fig. 6a, H⋯H contacts constitute the major contribution to the Hirshfeld surface, accounting for 36.8% of the total surface area. These contacts mainly arise from C—H⋯H interactions and emphasize the predominance of van der Waals forces in the crystal packing. The O⋯H/H⋯O contacts, shown in Fig. 6b, correspond to C—H⋯O hydrogen-bond interactions and represent the second most important contribution, accounting for 26.1% of the total interactions.

Figure 6
Hirshfeld surface analysis and two-dimensional fingerprint plots of the title compound illustrating: (a) H⋯H contacts, (b) O⋯H/H⋯O contacts, (c) H⋯C/C⋯H contacts, (d) N⋯H/H⋯N contacts, (e) C⋯C contacts; and Hirshfeld surface representations of the (f) shape-index and curvedness, highlighting π–π stacking interactions.

Fig. 6c displays the H⋯C/C⋯H contacts, which are associated with C—H⋯π interactions and contribute 14.9% to the Hirshfeld surface. In addition, the N⋯H/H⋯N contacts (Fig. 6d), attributable to O—H⋯N hydrogen bonds, represent 14.5% of the total surface area, highlighting the role of these interactions in the supramolecular assembly. The C⋯C contacts illustrated in Fig. 6e account for 5.3% of the total interactions and are indicative of π–π stacking interactions between aromatic rings (Fig. 6f). Other intermolecular contacts appear only as minor contributions in the fingerprint plots, including N⋯C/C⋯N (1.7%), O⋯C/C⋯O (0.5%) and O⋯O (0.2%) contacts.

6. Synthesis and crystallization

In a 10 ml glass vial, 0.25 mmol of 1,10-phenanthroline-5,6-dione was combined with an equimolar mixture of ethanol and acetone, filling approximately two-thirds of the vial. The vial was then placed in a microwave and irradiated at 393 K for 2 minutes. Following the addition of acetone, colourless crystals of (I) were obtained after 15 days at room temperature. Yield: 90%

7. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. Hydrogen atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95–0.99 Å and O—H = 0.84 Å. The constraint U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C or O) was applied in all cases.

Table 2
Experimental details

Crystal data
Chemical formula	C₁₅H₁₂N₂O₃
M_r	268.27
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	150
a, b, c (Å)	11.2440 (19), 12.604 (2), 8.9926 (14)
β (°)	106.870 (6)
V (Å³)	1219.6 (3)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	0.10
Crystal size (mm)	0.25 × 0.2 × 0.18

Data collection
Diffractometer	D8 VENTURE Bruker AXS
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
No. of measured, independent and observed [I > 2σ(I)] reflections	9853, 2781, 2205
R_int	0.046
(sin θ/λ)_max (Å⁻¹)	0.650

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.132, 1.03
No. of reflections	2781
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.28
Computer programs: APEX3 and SAINT (Bruker, 2015 ), SHELXT2018/2 (Sheldrick, 2015a ), SHELXL2018/3 (Sheldrick, 2015b ) and OLEX2 (Dolomanov et al., 2009 ).

Supporting information

CCDC reference: 2549869

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026004408/hb8213sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026004408/hb8213Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2056989026004408/hb8213Isup3.cml

checkCIF report

Computing details top

(RS)-6-Hydroxy-6-(2-oxopropyl)-1,10-phenanthrolin-5(6H)-one top

Crystal data top

C₁₅H₁₂N₂O₃	F(000) = 560
M_r = 268.27	D_x = 1.461 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
a = 11.2440 (19) Å	Cell parameters from 6286 reflections
b = 12.604 (2) Å	θ = 2.5–27.5°
c = 8.9926 (14) Å	µ = 0.10 mm⁻¹
β = 106.870 (6)°	T = 150 K
V = 1219.6 (3) Å³	Prism, colourless
Z = 4	0.25 × 0.2 × 0.18 mm

Data collection top

D8 VENTURE Bruker AXS diffractometer	2205 reflections with I > 2σ(I)
Detector resolution: 10.4167 pixels mm^-1	R_int = 0.046
rotation images scans	θ_max = 27.5°, θ_min = 2.5°
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	h = −14→14
	k = −13→16
9853 measured reflections	l = −11→11
2781 independent 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)] = 0.052	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0414P)² + 1.046P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
2781 reflections	Δρ_max = 0.30 e Å⁻³
183 parameters	Δρ_min = −0.28 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.

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

	x	y	z	U_iso*/U_eq
O1	0.66938 (12)	0.29055 (10)	0.12038 (15)	0.0220 (3)
H1	0.606402	0.305120	0.046242	0.033*
O3	0.84247 (13)	0.52378 (11)	0.43924 (16)	0.0299 (3)
O2	0.88727 (13)	0.39743 (12)	0.10860 (18)	0.0333 (4)
N1	0.47777 (13)	0.60754 (12)	0.17416 (17)	0.0194 (3)
N2	0.63092 (14)	0.70543 (12)	0.03798 (17)	0.0208 (3)
C12	0.57858 (15)	0.55159 (14)	0.16619 (18)	0.0152 (3)
C11	0.66176 (15)	0.60569 (14)	0.08928 (18)	0.0165 (4)
C7	0.76747 (15)	0.55389 (15)	0.07228 (19)	0.0183 (4)
C4	0.60379 (15)	0.44875 (14)	0.22495 (19)	0.0161 (4)
C3	0.52129 (16)	0.40246 (15)	0.29597 (19)	0.0194 (4)
H3	0.533697	0.331769	0.333955	0.023*
C5	0.71304 (16)	0.38418 (14)	0.20787 (19)	0.0174 (4)
C6	0.79761 (16)	0.44393 (15)	0.1278 (2)	0.0200 (4)
C10	0.70589 (18)	0.75471 (15)	−0.0311 (2)	0.0242 (4)
H10	0.685095	0.824996	−0.067532	0.029*
C14	0.84877 (15)	0.43219 (16)	0.4815 (2)	0.0215 (4)
C8	0.84341 (16)	0.60787 (16)	−0.0011 (2)	0.0226 (4)
H8	0.915370	0.574755	−0.014840	0.027*
C13	0.79505 (16)	0.34433 (15)	0.3669 (2)	0.0206 (4)
H13A	0.744812	0.296932	0.412625	0.025*
H13B	0.864221	0.301854	0.350456	0.025*
C1	0.40297 (17)	0.56254 (16)	0.2471 (2)	0.0226 (4)
H1A	0.333471	0.601967	0.256368	0.027*
C2	0.42114 (16)	0.46134 (16)	0.3101 (2)	0.0214 (4)
H2	0.365825	0.432869	0.362005	0.026*
C9	0.81238 (18)	0.70962 (17)	−0.0529 (2)	0.0267 (4)
H9	0.862611	0.748262	−0.102620	0.032*
C15	0.90883 (18)	0.39957 (18)	0.6461 (2)	0.0291 (5)
H15A	0.988278	0.364693	0.653789	0.044*
H15B	0.854171	0.350215	0.679350	0.044*
H15C	0.923377	0.462428	0.713143	0.044*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0252 (7)	0.0134 (7)	0.0246 (7)	0.0021 (5)	0.0030 (5)	−0.0026 (5)
O3	0.0307 (7)	0.0206 (8)	0.0337 (7)	−0.0007 (6)	0.0021 (6)	0.0004 (6)
O2	0.0312 (7)	0.0280 (8)	0.0482 (9)	0.0095 (6)	0.0234 (7)	0.0086 (7)
N1	0.0195 (7)	0.0160 (8)	0.0235 (7)	0.0012 (6)	0.0072 (6)	−0.0008 (6)
N2	0.0263 (8)	0.0150 (8)	0.0210 (7)	0.0009 (6)	0.0065 (6)	0.0020 (6)
C12	0.0169 (8)	0.0147 (9)	0.0137 (7)	−0.0003 (6)	0.0041 (6)	−0.0020 (6)
C11	0.0185 (8)	0.0148 (9)	0.0148 (7)	−0.0011 (6)	0.0025 (6)	−0.0010 (6)
C7	0.0177 (8)	0.0192 (9)	0.0171 (8)	−0.0017 (7)	0.0035 (6)	−0.0003 (7)
C4	0.0182 (8)	0.0149 (9)	0.0146 (7)	−0.0001 (6)	0.0037 (6)	−0.0026 (6)
C3	0.0240 (9)	0.0153 (9)	0.0186 (8)	−0.0017 (7)	0.0058 (7)	0.0016 (7)
C5	0.0211 (8)	0.0116 (8)	0.0195 (8)	0.0013 (7)	0.0060 (6)	0.0026 (7)
C6	0.0200 (8)	0.0192 (10)	0.0213 (8)	0.0030 (7)	0.0068 (7)	0.0009 (7)
C10	0.0308 (10)	0.0162 (10)	0.0252 (9)	−0.0020 (8)	0.0073 (7)	0.0047 (7)
C14	0.0157 (8)	0.0257 (11)	0.0233 (9)	0.0027 (7)	0.0062 (7)	0.0025 (8)
C8	0.0195 (8)	0.0246 (10)	0.0242 (9)	−0.0007 (7)	0.0071 (7)	0.0019 (8)
C13	0.0224 (8)	0.0183 (10)	0.0195 (8)	0.0036 (7)	0.0038 (7)	0.0026 (7)
C1	0.0202 (8)	0.0229 (10)	0.0263 (9)	0.0013 (7)	0.0091 (7)	−0.0035 (8)
C2	0.0222 (9)	0.0239 (10)	0.0203 (8)	−0.0034 (7)	0.0098 (7)	−0.0013 (7)
C9	0.0265 (9)	0.0280 (11)	0.0270 (9)	−0.0052 (8)	0.0101 (7)	0.0061 (8)
C15	0.0252 (9)	0.0380 (13)	0.0223 (9)	−0.0042 (9)	0.0040 (7)	0.0019 (9)

Geometric parameters (Å, º) top

O1—H1	0.8400	C5—C6	1.545 (2)
O1—C5	1.424 (2)	C5—C13	1.543 (2)
O3—C14	1.211 (2)	C10—H10	0.9500
O2—C6	1.221 (2)	C10—C9	1.390 (3)
N1—C12	1.354 (2)	C14—C13	1.514 (3)
N1—C1	1.334 (2)	C14—C15	1.496 (2)
N2—C11	1.349 (2)	C8—H8	0.9500
N2—C10	1.336 (2)	C8—C9	1.375 (3)
C12—C11	1.481 (2)	C13—H13A	0.9900
C12—C4	1.398 (2)	C13—H13B	0.9900
C11—C7	1.403 (2)	C1—H1A	0.9500
C7—C6	1.479 (3)	C1—C2	1.386 (3)
C7—C8	1.398 (2)	C2—H2	0.9500
C4—C3	1.397 (2)	C9—H9	0.9500
C4—C5	1.518 (2)	C15—H15A	0.9800
C3—H3	0.9500	C15—H15B	0.9800
C3—C2	1.385 (3)	C15—H15C	0.9800

C5—O1—H1	109.5	C9—C10—H10	117.9
C1—N1—C12	117.48 (16)	O3—C14—C13	120.55 (16)
C10—N2—C11	117.24 (16)	O3—C14—C15	122.76 (18)
N1—C12—C11	115.89 (15)	C15—C14—C13	116.69 (17)
N1—C12—C4	122.95 (15)	C7—C8—H8	120.5
C4—C12—C11	121.15 (15)	C9—C8—C7	118.99 (17)
N2—C11—C12	117.01 (15)	C9—C8—H8	120.5
N2—C11—C7	122.56 (16)	C5—C13—H13A	108.8
C7—C11—C12	120.43 (16)	C5—C13—H13B	108.8
C11—C7—C6	121.18 (15)	C14—C13—C5	113.94 (15)
C8—C7—C11	118.54 (17)	C14—C13—H13A	108.8
C8—C7—C6	120.28 (16)	C14—C13—H13B	108.8
C12—C4—C5	122.71 (15)	H13A—C13—H13B	107.7
C3—C4—C12	118.12 (16)	N1—C1—H1A	118.2
C3—C4—C5	119.11 (16)	N1—C1—C2	123.56 (17)
C4—C3—H3	120.5	C2—C1—H1A	118.2
C2—C3—C4	118.91 (17)	C3—C2—C1	118.88 (16)
C2—C3—H3	120.5	C3—C2—H2	120.6
O1—C5—C4	109.93 (14)	C1—C2—H2	120.6
O1—C5—C6	107.86 (14)	C10—C9—H9	120.7
O1—C5—C13	105.05 (14)	C8—C9—C10	118.54 (17)
C4—C5—C6	114.29 (14)	C8—C9—H9	120.7
C4—C5—C13	111.36 (14)	C14—C15—H15A	109.5
C13—C5—C6	107.89 (14)	C14—C15—H15B	109.5
O2—C6—C7	121.31 (16)	C14—C15—H15C	109.5
O2—C6—C5	118.50 (16)	H15A—C15—H15B	109.5
C7—C6—C5	120.17 (15)	H15A—C15—H15C	109.5
N2—C10—H10	117.9	H15B—C15—H15C	109.5
N2—C10—C9	124.13 (18)

O1—C5—C6—O2	−57.0 (2)	C11—C7—C8—C9	0.4 (3)
O1—C5—C6—C7	121.28 (16)	C7—C8—C9—C10	−0.4 (3)
O1—C5—C13—C14	−178.29 (14)	C4—C12—C11—N2	−179.14 (15)
O3—C14—C13—C5	−11.3 (2)	C4—C12—C11—C7	0.7 (2)
N1—C12—C11—N2	1.4 (2)	C4—C3—C2—C1	2.8 (3)
N1—C12—C11—C7	−178.76 (14)	C4—C5—C6—O2	−179.53 (16)
N1—C12—C4—C3	−0.5 (2)	C4—C5—C6—C7	−1.3 (2)
N1—C12—C4—C5	176.56 (15)	C4—C5—C13—C14	−59.34 (19)
N1—C1—C2—C3	−0.7 (3)	C3—C4—C5—O1	58.65 (19)
N2—C11—C7—C6	−179.12 (15)	C3—C4—C5—C6	−179.92 (14)
N2—C11—C7—C8	−0.2 (3)	C3—C4—C5—C13	−57.3 (2)
N2—C10—C9—C8	0.1 (3)	C5—C4—C3—C2	−179.43 (15)
C12—N1—C1—C2	−2.0 (3)	C6—C7—C8—C9	179.34 (16)
C12—C11—C7—C6	1.0 (2)	C6—C5—C13—C14	66.84 (18)
C12—C11—C7—C8	179.99 (15)	C10—N2—C11—C12	179.80 (15)
C12—C4—C3—C2	−2.3 (2)	C10—N2—C11—C7	−0.1 (2)
C12—C4—C5—O1	−118.38 (16)	C8—C7—C6—O2	−1.4 (3)
C12—C4—C5—C6	3.1 (2)	C8—C7—C6—C5	−179.59 (16)
C12—C4—C5—C13	125.62 (17)	C13—C5—C6—O2	56.0 (2)
C11—N2—C10—C9	0.1 (3)	C13—C5—C6—C7	−125.72 (16)
C11—C12—C4—C3	−179.94 (15)	C1—N1—C12—C11	−177.91 (15)
C11—C12—C4—C5	−2.9 (2)	C1—N1—C12—C4	2.6 (2)
C11—C7—C6—O2	177.55 (17)	C15—C14—C13—C5	168.82 (15)
C11—C7—C6—C5	−0.7 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N1ⁱ	0.84	2.22	2.977 (2)	149
O1—H1···N2ⁱ	0.84	2.56	3.262 (2)	142
C13—H13A···O1ⁱⁱ	0.99	2.52	3.457 (2)	158
C15—H15B···O1ⁱⁱ	0.98	2.67	3.561 (3)	152
C1—H1A···O1ⁱⁱⁱ	0.95	2.63	3.302 (2)	128
C3—H3···N1ⁱⁱⁱ	0.95	2.83	3.727 (2)	158
C8—H8···O2^iv	0.95	2.62	3.436 (3)	145
C10—H10···O3^v	0.95	2.59	3.235 (2)	125
C15—H15A···O3^vi	0.98	2.69	3.254 (3)	117

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

Acknowledgements

We sincerely thank the OMC team at the University of Rennes, CNRS, Institut des Sciences Chimiques de Rennes (ISCR)–UMR 6226, France, for their valuable assistance during BT's internship and for their support of the data collection.

Funding information

We gratefully acknowledge the financial support provided by the Ministry of Higher Education and Scientific Research of Algeria (MESRS) and the General Directorate for Scientific Research and Technological Development (DGRSDT).

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