research communications
thermal and fluorescence properties of 2,2′:6′,2′′-terpyridine-1,1′,1′′-triium tetrachloridonickelate(II) chloride
aUnité de Recherche Chimie de l'Environnement et Moléculaire, Structurale, 'CHEMS', Faculté des Sciences Exactes,Campus Chaabet Ersas, Université, Frères Mentouri Constantine 1, 25000 Constantine, Algeria, bCentre de Recherche en Biotechnologie, Constantine, Algeria, and cLaboratoire de Chimie de Coordination, UPR-CNRS 8241, 205 route de Narbonne, 31077 Toulouse Cedex 4, France
*Correspondence e-mail: bendjeddoulamia@gmail.com
The title compound, (C15H14N3)[NiCl4]Cl, comprises an NiII cation tetrahedrally coordinated by four chloride anions, a non-coordinating chloride anion and an essentially planar terpyridinium trication (tpyH33+), in which the central pyridinium ring forms dihedral angles of 5.7 (2) and 6.0 (2)° with the peripheral pyridinium rings. Three inter-species N—H⋯Cl hydrogen bonds are formed with the Cl− anion, which also forms a link between the (tpyH33+) cations through an aromatic C—H⋯Cl interaction, forming a zigzag chain extending along the 21 (b) screw axis. Two of the anionic Cl atoms of the [NiCl4]2− anions form Ni—Cl⋯π interactions with separate pyridinium rings [Ni⋯Cg = 3.669 (3) and 3.916 (4) Å]. In the crystal, successive undulating inorganic and organic layers are formed, extending across the (100) plane. Thermogravimetric and (TGA/DTA) indicate that the compound starts to decompose at 313 K and may be a candidate for use as a blue-light luminescent material.
Keywords: crystal structure; nickel(II) complex; terpyridinium cation; protonation; hydrogen bonds; fluorescence.
CCDC reference: 1587116
1. Chemical context
The 2,2′:6′,2′′-terpyridine molecule (tpy) has been the object of numerous studies because of its excellent complexing properties on metal ions. The multitude of applications of this cation motivated a large development in the synthesis of terpyridines during the last decade. The compounds derived from the terpyridine molecule can be used in et al., 2012), the assembly of electrochemical sensors (Indelli et al., 1998), in (Mori et al., 2012) and as a sensitizing agent in photovoltaic conversion processes (Kohle et al., 1996). The literature reports some hybrid complexes of transition metal species incorporating tpy as a neutral ligand as well as complexes with its protonated forms [(tpyH+), (tpyH22+), (tpyH33+)] (Kochel, 2006). The title compound, which is a new hybrid complex, was characterized using IR spectroscopy and X-ray crystallography and its thermal and fluorescence properties have also been recorded.
for the realization of luminescent materials (Adeloye2. Structural commentary
Crystals of (C15H14N3)[NiCl4]Cl, (I), are monoclinic (space group P21), the comprising an organic terpyridinium (tpyH33+) cation, a tetrachloronickelate(II) [NiCl4]2− dianion and a free chloride anion (Cl5) (Fig. 1).
The (tpyH33+) cation has the cis–cis conformation and is essentially planar, with dihedral angles between the central pyridine ring and the two peripheral ring moieties of the ligand of 5.7 (2) and 6.0 (2)°. The three protonated N atoms (N1, N2 and N3) form hydrogen bonds with the chloride counter-anion (Cl5) (Table 1), giving short H11⋯H22 and H22⋯H33 contacts (1.70 and 1.68 Å, respectively), which are comparable to those reported for tpyH3Cl(PF6)2 (H⋯H range: 1.667–1.684 Å; Yoshikawa et al., 2016). The complete protonation of an aromatic molecule that is nitrogen-enriched (a polynitrogenous derivative) is rarely observed, probably because of an unfavorable charge distribution resulting from the proximity of the nitrogen H atoms, as previously indicated in this structure. This results in an opening of the internal angles of the three N atoms [C1—N1—C5 = 124.0 (4), C10—N2—C6 = 118.9 (3) and C15—N3—C11 = 123.2 (3)°]. These values are comparable to those found in the literature for (tpyH33+). In 2,2′:6′,2′′-terpyridinetriium bis(hexafluoridophosphate) chloride (Yoshikawa et al., 2016), C1—N1—C5 = 122.90, C6—N2—C10 = 117.60 and C11—N3—C15 = 123.27, C16—N4—C20 = 123.69, C21—N5—C25 = 118.22 and C26—N6—C30 = 123.97° and in catena-[(2,2′:6′,2′′-terpyridinium)(μ3-sulfato)sulfatodioxouranium) nitrate dihydrate] (Jie Ling et al., 2010), C1—N1—C5 = 123.33, C6—N2—C10 = 118.03 and C11—N3—C15 = 123.29°. The internal angles for a deprotonated terpyridine are C1—N1—C5 = 116.9 (8), C10—N2—C6 = 119.6 (11) and C15—N3—C11 = 117.1 (8)° (Maynard et al., 2009).
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The nickel(II) centre of the dianion has a quasi-regular tetrahedral environment [Ni—Cl bond length range, 2.185 (2)–2.201 (2) Å and Cl—Ni—Cl bond angle range, 108.08 (5)–111.59 (5)°] (Fig. 2). The interatomic distance and angle values are in good agreement with those taken from the literature (Igashira-Kamiyama et al., 2013).
3. Supramolecular features
The previously described inter-species unit formed through the three individual N—H⋯Cl hydrogen bonds between the (tpyH33+) cation and the Cl5− anion (Table 1) is extended through a C14—H14⋯Cl5i hydrogen bond into chains extending along the 21 screw axis of the Convoluted layers comprising successive [tpyH33+, Cl−] (type A) and [NiCl4]2− (type B) ions extend across the (100) plane (Figs. 3 and 4). Two of the anionic Cl atoms of the [NiCl4]2− anion form Ni—Cl⋯π interactions with separate pyridine ring moieties of the cation within the Ni1—Cl1⋯Cg1 = 3.916 (4) Å and Ni1—Cl2⋯Cg2 = 3.669 (3) Å, where Cg1 and Cg2 are the centroids of the N1/C1–C5 and N2/C6–C10 rings, respectively (Fig. 3).
4. Thermogravimetric analysis (TGA)
Thermal analyses were performed on a SETARM 92-16.18 PC/PG 1 instrument from 303 to 1273 K under a dynamic air atmosphere and under nitrogen at 200.0 ml min−1 with a heating rate of 10 K min−1.
The stability of the (C15H14N3)[NiCl4]Cl complex was measured by TGA and the experimental results are in agreement with the calculated data. As shown in Fig. 5, the first weight loss of 16.5% (calculated 15.21%) at 40–126 K corresponds to the loss of the two coordinated chloride anions and the second loss of 48.6% (calculated 49.9%) at 126–281 K corresponds to the loss of the organic molecule tpyH33+, and then the two coordinated and free chloride anions gradually decompose (ΔP/P = 23.14%, calculated = 22.51%). In addition, the corresponding endothermic peaks (at 394.16; 554.63°C and at 638 K) in the differential scanning ATD curve also record the processes of weight loss.
5. Luminescent properties
spectra were measured using a Cary Eclipse (Agilent Technologies) fluorescence spectrophotometer.
The fluorescence properties of (C15H14N3)[NiCl4]Cl and the free ligand tpy were investigated in the solid state at 298 K. As depicted in Fig. 6, the new compound (I) exhibits fluorescence emission at ca 481 nm (excited at 250 nm) compared to that of tpy (425 nm, excited at 250 nm), which can be attributed to π–π* electronic transitions. Thus, the title compound may be a candidate for use as a blue-light luminescent material and it is believed that more transition metal with good luminescent properties may be developed (Wen et al., 2007; Zhang et al., 2010; Huang et al., 2013).
6. Database survey
A search of the Cambridge Structural Database (Version 5.38; Groom et al., 2016) shows 4279 hits comprising the terpyridine species. However, only two structures containing the (tpyH33+) form are present (Ling et al., 2010; Yoshikawa et al., 2016).
7. Synthesis and crystallization
All the chemicals and solvents were purchased commercially and used as received. The infrared spectra were recorded on a Perkin–Elmer spectrometer at room temperature in the range of 4000–500 cm−1. tpy (1.67 g, 10 mmol) was dissolved in a 50/50 mixture of water and ethanol (20 ml) in a 50 ml round-bottom flask. Nickel(II) chloride (2.50 g, 10 mmol) was added to the flask to give a green-coloured solution that was stirred for 3 h under gentle heat, producing a green-coloured precipitate. The precipitate was filtered and washed twice with cold water/ethanol solvent then dried under vacuum for 20 min, producing a green powder (2.7g, 64% yield). Green prismatic crystals of the title complex (I) suitable for X-ray analysis were obtained from water/ethanol solvent. IR of (I) (cm−1): 3390 (v/s), 2930 (v/s), 1667.8 (s), 1622.4 (s), 1417.4 (m), 987.6 (w), 540.6 (w).
8. Refinement
Crystal data, data collection and structure . All H atoms were placed at calculated positions and refined as riding atoms, with C—H = 0.93 Å, N—H = 0.86 Å and with Uiso(H) = 1.2Ueq(C,N). Although not of relevance with this achiral molecule, the (Flack, 1983) was determined as 0.178 (16) for 4425 Friedel pairs. Minor non-merohedral was identified and allowed for in the giving a BASF factor of 0.1783.
details are summarized in Table 2Supporting information
CCDC reference: 1587116
https://doi.org/10.1107/S2056989017016784/zs2392sup1.cif
contains datablock I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989017016784/zs2392Isup2.hkl
Data collection: APEX2 (Bruker, 2006); cell
SAINT (Bruker, 2006); data reduction: SAINT (Bruker, 2006); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 2012); software used to prepare material for publication: Mercury (Macrae et al., 2008) and POVRay (Persistence of Vision, 2004).(C15H14N3)[NiCl4]Cl | F(000) = 476 |
Mr = 472.25 | Dx = 1.630 Mg m−3 |
Monoclinic, P21 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2yb | Cell parameters from 6308 reflections |
a = 6.689 (5) Å | θ = 3.0–36.1° |
b = 13.809 (5) Å | µ = 1.71 mm−1 |
c = 10.620 (5) Å | T = 293 K |
β = 101.271 (5)° | Prism, green |
V = 962.0 (9) Å3 | 0.20 × 0.10 × 0.08 mm |
Z = 2 |
Bruker APEXII CCD diffractometer | 6308 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.031 |
Graphite monochromator | θmax = 36.1°, θmin = 3.0° |
φ and ω scans | h = −11→10 |
36239 measured reflections | k = −22→22 |
8772 independent reflections | l = −17→17 |
Refinement on F2 | Primary atom site location: structure-invariant direct methods |
Least-squares matrix: full | Secondary atom site location: difference Fourier map |
R[F2 > 2σ(F2)] = 0.059 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.150 | H-atom parameters constrained |
S = 1.15 | w = 1/[σ2(Fo2) + (0.0529P)2 + 0.6276P] where P = (Fo2 + 2Fc2)/3 |
8772 reflections | (Δ/σ)max < 0.001 |
218 parameters | Δρmax = 0.54 e Å−3 |
1 restraint | Δρmin = −0.51 e Å−3 |
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2>2sigma(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. |
x | y | z | Uiso*/Ueq | ||
N1 | 0.6965 (5) | 0.0120 (2) | 0.2808 (3) | 0.0423 (8) | |
N2 | 0.6834 (4) | 0.1969 (2) | 0.2073 (2) | 0.0345 (7) | |
N3 | 0.3276 (4) | 0.2445 (2) | 0.0620 (3) | 0.0378 (8) | |
C1 | 0.6807 (7) | −0.0822 (3) | 0.3068 (4) | 0.0564 (14) | |
C2 | 0.8509 (9) | −0.1305 (4) | 0.3730 (5) | 0.0682 (16) | |
C3 | 1.0290 (9) | −0.0823 (4) | 0.4081 (5) | 0.0704 (16) | |
C4 | 1.0401 (7) | 0.0151 (4) | 0.3788 (4) | 0.0570 (14) | |
C5 | 0.8694 (5) | 0.0637 (3) | 0.3144 (3) | 0.0400 (9) | |
C6 | 0.8612 (5) | 0.1667 (3) | 0.2779 (3) | 0.0377 (8) | |
C7 | 1.0221 (6) | 0.2299 (4) | 0.3166 (4) | 0.0514 (13) | |
C8 | 0.9989 (6) | 0.3259 (3) | 0.2837 (5) | 0.0566 (11) | |
C9 | 0.8147 (6) | 0.3578 (3) | 0.2109 (4) | 0.0510 (11) | |
C10 | 0.6616 (5) | 0.2905 (2) | 0.1750 (3) | 0.0360 (8) | |
C11 | 0.4595 (5) | 0.3173 (2) | 0.0989 (3) | 0.0374 (8) | |
C12 | 0.3955 (7) | 0.4115 (3) | 0.0654 (4) | 0.0493 (11) | |
C13 | 0.1989 (7) | 0.4256 (3) | −0.0041 (4) | 0.0555 (14) | |
C14 | 0.0724 (7) | 0.3501 (4) | −0.0406 (4) | 0.0574 (14) | |
C15 | 0.1389 (6) | 0.2582 (3) | −0.0065 (4) | 0.0496 (11) | |
Ni1 | 0.67429 (7) | 0.12776 (3) | 0.66208 (4) | 0.0431 (1) | |
Cl1 | 0.53022 (16) | −0.01301 (7) | 0.60866 (11) | 0.0556 (3) | |
Cl2 | 0.55986 (17) | 0.23114 (8) | 0.50704 (10) | 0.0576 (3) | |
Cl3 | 0.6050 (2) | 0.18121 (10) | 0.84272 (11) | 0.0672 (4) | |
Cl4 | 1.00476 (14) | 0.11245 (9) | 0.68627 (12) | 0.0629 (4) | |
Cl5 | 0.27653 (15) | 0.03265 (7) | 0.11437 (12) | 0.0576 (3) | |
H1 | 0.55780 | −0.11470 | 0.28090 | 0.0680* | |
H2 | 0.84260 | −0.19570 | 0.39320 | 0.0820* | |
H3 | 1.14390 | −0.11440 | 0.45200 | 0.0840* | |
H4 | 1.16290 | 0.04800 | 0.40240 | 0.0680* | |
H7 | 1.14480 | 0.20740 | 0.36450 | 0.0620* | |
H8 | 1.10530 | 0.36920 | 0.30980 | 0.0680* | |
H9 | 0.79550 | 0.42250 | 0.18730 | 0.0610* | |
H11 | 0.58970 | 0.04130 | 0.24020 | 0.0510* | |
H12 | 0.48240 | 0.46380 | 0.08890 | 0.0590* | |
H13 | 0.15350 | 0.48820 | −0.02590 | 0.0670* | |
H14 | −0.05810 | 0.36030 | −0.08820 | 0.0690* | |
H15 | 0.05350 | 0.20540 | −0.03080 | 0.0600* | |
H22 | 0.58510 | 0.15670 | 0.18310 | 0.0410* | |
H33 | 0.36610 | 0.18630 | 0.08330 | 0.0450* |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0412 (14) | 0.0405 (14) | 0.0434 (14) | 0.0049 (11) | 0.0040 (11) | 0.0059 (11) |
N2 | 0.0329 (11) | 0.0359 (12) | 0.0329 (11) | −0.0041 (9) | 0.0023 (9) | −0.0026 (10) |
N3 | 0.0373 (13) | 0.0349 (13) | 0.0394 (13) | 0.0067 (10) | 0.0029 (10) | −0.0032 (10) |
C1 | 0.069 (3) | 0.044 (2) | 0.057 (2) | 0.0067 (19) | 0.014 (2) | 0.0092 (17) |
C2 | 0.099 (4) | 0.050 (2) | 0.059 (2) | 0.021 (3) | 0.024 (3) | 0.017 (2) |
C3 | 0.067 (3) | 0.081 (3) | 0.061 (2) | 0.032 (3) | 0.007 (2) | 0.016 (2) |
C4 | 0.047 (2) | 0.073 (3) | 0.048 (2) | 0.0178 (19) | 0.0019 (16) | 0.0088 (19) |
C5 | 0.0381 (15) | 0.0508 (18) | 0.0295 (13) | 0.0063 (14) | 0.0024 (11) | 0.0005 (12) |
C6 | 0.0330 (13) | 0.0479 (17) | 0.0306 (13) | −0.0024 (12) | 0.0024 (11) | −0.0055 (12) |
C7 | 0.0339 (15) | 0.069 (3) | 0.0476 (19) | −0.0069 (16) | −0.0011 (14) | −0.0065 (18) |
C8 | 0.0444 (19) | 0.061 (2) | 0.063 (2) | −0.0246 (17) | 0.0074 (18) | −0.0163 (19) |
C9 | 0.052 (2) | 0.0391 (17) | 0.064 (2) | −0.0166 (15) | 0.0168 (18) | −0.0104 (16) |
C10 | 0.0373 (14) | 0.0345 (14) | 0.0361 (14) | −0.0030 (11) | 0.0070 (12) | −0.0056 (11) |
C11 | 0.0431 (16) | 0.0350 (14) | 0.0352 (14) | 0.0037 (12) | 0.0106 (12) | −0.0022 (11) |
C12 | 0.061 (2) | 0.0354 (16) | 0.053 (2) | 0.0041 (15) | 0.0147 (17) | 0.0042 (14) |
C13 | 0.068 (3) | 0.050 (2) | 0.0486 (19) | 0.0185 (19) | 0.0118 (18) | 0.0102 (17) |
C14 | 0.057 (2) | 0.062 (3) | 0.049 (2) | 0.024 (2) | 0.0004 (17) | 0.0058 (18) |
C15 | 0.0417 (18) | 0.055 (2) | 0.0487 (19) | 0.0085 (15) | 0.0002 (15) | −0.0056 (16) |
Ni1 | 0.0447 (2) | 0.0389 (2) | 0.0450 (2) | 0.0022 (2) | 0.0074 (2) | −0.0037 (2) |
Cl1 | 0.0557 (5) | 0.0396 (4) | 0.0668 (6) | −0.0065 (4) | 0.0008 (4) | −0.0078 (4) |
Cl2 | 0.0582 (6) | 0.0542 (5) | 0.0578 (5) | 0.0045 (4) | 0.0048 (4) | 0.0156 (4) |
Cl3 | 0.0789 (7) | 0.0736 (7) | 0.0531 (5) | 0.0027 (6) | 0.0231 (5) | −0.0196 (5) |
Cl4 | 0.0395 (4) | 0.0623 (7) | 0.0851 (7) | 0.0057 (4) | 0.0075 (4) | −0.0053 (5) |
Cl5 | 0.0413 (4) | 0.0435 (5) | 0.0823 (7) | −0.0114 (4) | −0.0017 (4) | 0.0015 (5) |
Ni1—Cl1 | 2.194 (2) | C7—C8 | 1.372 (7) |
Ni1—Cl2 | 2.201 (2) | C8—C9 | 1.392 (6) |
Ni1—Cl3 | 2.188 (2) | C9—C10 | 1.380 (5) |
Ni1—Cl4 | 2.185 (2) | C10—C11 | 1.480 (5) |
N1—C5 | 1.347 (5) | C11—C12 | 1.394 (5) |
N1—C1 | 1.338 (5) | C12—C13 | 1.390 (7) |
N2—C6 | 1.342 (4) | C13—C14 | 1.351 (7) |
N2—C10 | 1.338 (4) | C14—C15 | 1.370 (7) |
N3—C15 | 1.341 (5) | C1—H1 | 0.9300 |
N3—C11 | 1.344 (4) | C2—H2 | 0.9300 |
N1—H11 | 0.8600 | C3—H3 | 0.9300 |
N2—H22 | 0.8600 | C4—H4 | 0.9300 |
N3—H33 | 0.8600 | C7—H7 | 0.9300 |
C1—C2 | 1.387 (7) | C8—H8 | 0.9300 |
C2—C3 | 1.352 (8) | C9—H9 | 0.9300 |
C3—C4 | 1.386 (8) | C12—H12 | 0.9300 |
C4—C5 | 1.384 (6) | C13—H13 | 0.9300 |
C5—C6 | 1.472 (6) | C14—H14 | 0.9300 |
C6—C7 | 1.384 (6) | C15—H15 | 0.9300 |
Cl1—Ni1—Cl4 | 109.13 (5) | N2—C10—C9 | 122.8 (3) |
Cl1—Ni1—Cl2 | 108.08 (5) | N3—C11—C10 | 116.7 (3) |
Cl1—Ni1—Cl3 | 111.59 (5) | N3—C11—C12 | 118.2 (3) |
Cl3—Ni1—Cl4 | 108.20 (5) | C10—C11—C12 | 125.1 (3) |
Cl2—Ni1—Cl3 | 109.57 (5) | C11—C12—C13 | 118.5 (4) |
Cl2—Ni1—Cl4 | 110.28 (5) | C12—C13—C14 | 121.3 (4) |
C1—N1—C5 | 124.0 (4) | C13—C14—C15 | 119.1 (4) |
C6—N2—C10 | 118.9 (3) | N3—C15—C14 | 119.8 (4) |
C11—N3—C15 | 123.2 (3) | N1—C1—H1 | 121.00 |
C5—N1—H11 | 118.00 | C2—C1—H1 | 121.00 |
C1—N1—H11 | 118.00 | C1—C2—H2 | 120.00 |
C10—N2—H22 | 121.00 | C3—C2—H2 | 120.00 |
C6—N2—H22 | 121.00 | C4—C3—H3 | 120.00 |
C15—N3—H33 | 118.00 | C2—C3—H3 | 120.00 |
C11—N3—H33 | 118.00 | C3—C4—H4 | 120.00 |
N1—C1—C2 | 118.8 (4) | C5—C4—H4 | 120.00 |
C1—C2—C3 | 119.7 (5) | C6—C7—H7 | 120.00 |
C2—C3—C4 | 119.9 (5) | C8—C7—H7 | 120.00 |
C3—C4—C5 | 120.4 (5) | C9—C8—H8 | 120.00 |
N1—C5—C4 | 117.2 (4) | C7—C8—H8 | 120.00 |
C4—C5—C6 | 125.7 (4) | C8—C9—H9 | 121.00 |
N1—C5—C6 | 117.2 (3) | C10—C9—H9 | 121.00 |
N2—C6—C5 | 115.5 (3) | C11—C12—H12 | 121.00 |
N2—C6—C7 | 121.5 (4) | C13—C12—H12 | 121.00 |
C5—C6—C7 | 123.0 (3) | C14—C13—H13 | 119.00 |
C6—C7—C8 | 119.4 (4) | C12—C13—H13 | 119.00 |
C7—C8—C9 | 119.4 (4) | C13—C14—H14 | 121.00 |
C8—C9—C10 | 118.0 (4) | C15—C14—H14 | 120.00 |
N2—C10—C11 | 115.1 (3) | C14—C15—H15 | 120.00 |
C9—C10—C11 | 122.1 (3) | N3—C15—H15 | 120.00 |
C5—N1—C1—C2 | 0.4 (6) | C4—C5—C6—N2 | 175.1 (3) |
C1—N1—C5—C4 | 0.5 (5) | C4—C5—C6—C7 | −7.0 (6) |
C1—N1—C5—C6 | 179.7 (3) | N2—C6—C7—C8 | 0.9 (6) |
C10—N2—C6—C5 | 177.3 (3) | C5—C6—C7—C8 | −176.8 (4) |
C10—N2—C6—C7 | −0.7 (5) | C6—C7—C8—C9 | −0.7 (7) |
C6—N2—C10—C9 | 0.2 (5) | C7—C8—C9—C10 | 0.2 (6) |
C6—N2—C10—C11 | −179.1 (3) | C8—C9—C10—N2 | 0.1 (6) |
C15—N3—C11—C10 | 179.5 (3) | C8—C9—C10—C11 | 179.3 (4) |
C15—N3—C11—C12 | 0.8 (5) | N2—C10—C11—N3 | −5.3 (4) |
C11—N3—C15—C14 | −0.8 (6) | N2—C10—C11—C12 | 173.4 (3) |
N1—C1—C2—C3 | −1.0 (7) | C9—C10—C11—N3 | 175.5 (3) |
C1—C2—C3—C4 | 0.6 (8) | C9—C10—C11—C12 | −5.9 (5) |
C2—C3—C4—C5 | 0.4 (7) | N3—C11—C12—C13 | 0.1 (6) |
C3—C4—C5—N1 | −1.0 (6) | C10—C11—C12—C13 | −178.5 (4) |
C3—C4—C5—C6 | 179.9 (4) | C11—C12—C13—C14 | −1.0 (6) |
N1—C5—C6—N2 | −4.0 (4) | C12—C13—C14—C15 | 1.0 (7) |
N1—C5—C6—C7 | 173.9 (3) | C13—C14—C15—N3 | −0.1 (6) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H11···Cl5 | 0.86 | 2.26 | 3.026 (4) | 149 |
N1—H11···N2 | 0.86 | 2.28 | 2.666 (4) | 107 |
N2—H22···Cl5 | 0.86 | 2.67 | 3.532 (4) | 178 |
N2—H22···N3 | 0.86 | 2.29 | 2.654 (4) | 106 |
N3—H33···Cl5 | 0.86 | 2.25 | 3.010 (4) | 148 |
C14—H14···Cl5i | 0.93 | 2.78 | 3.421 (6) | 127 |
Symmetry code: (i) −x, y+1/2, −z. |
Funding information
This work was supported by the Unité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (URCHEMS), Université Frères Mentouri Constantine, Algeria, and the Biotechnology Research Center (CRBt), Constantine, Algeria. Thanks are due to MESRS and ATRST (Ministère de l'Enseignement Supérieur et de la Recherche Scientifique et l'Agence Thématique de Recherche en Sciences et Technologie, Algérie) for financial support via the PNR program.
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