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Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 82| Part 10| October 2026| Pages 1226-1229
https://doi.org/10.1107/S2056989026009448

Mol­ecular and crystal structure of (Z)-N-allyl-3-(allyl­imino)-3H-isoindol-1-amine

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Volodymyr A. Tkachuk,a Svitlana V. Shishkinab* and Olga V. Hordiyenkoa

aNational Taras Shevchenko University of Kyiv, Faculty of Chemistry, 64/13, Volodymyrs'ka str., 01601, Kyiv, Ukraine, and bInstitute of Organic Chemistry, NAS of Ukraine, Akademik Kukhar Street 5, Kyiv 02094, Ukraine
*Correspondence e-mail: [email protected]

Edited by M. Weil, Vienna University of Technology, Austria (Received 29 May 2026; accepted 9 September 2026; online 30 September 2026)

The 3-imino-3H-isoindol-1-amine tautomeric form of (Z)-N-allyl-3-(allyl­imino)-3H-isoindol-1-amine, C14H15N3, was confirmed by a single-crystal X-ray diffraction study. The distribution of electron density within the —NH—C=N—C=N— conjugated fragment corresponds to that found in previously studied N,N′-disubstituted 3-imino-3H-isoindol-1-amines. The two mol­ecules in the asymmetric unit of the title compound differ in the conformation of the allyl substituents. In one of these mol­ecules, the two allyl fragments are disordered over two sets of sites in 0.628 (7):0.372 (7) and 0.755 (5):0.245 (5) ratios. In the crystal, the two unique mol­ecules are arranged alternately in infinite chains parallel to [001] due to the formation of inter­molecular N—H⋯N hydrogen bonds.

CCDC reference: 2586660

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1. Chemical context

Since the first synthesis and characterisation of 3-imino-3H-iso­indole-1-amine and its N,N′-disubstituted derivatives (Elvidge & Linstead, 1952View full citation; Clark et al., 1953View full citation), these compounds have been of inter­est as important inter­mediates in the synthesis of phthalocyanines and related compounds. They also exhibit structural features attributable to the presence of the conjugation fragment –NH—C=N–C=N–, in which tautomeric migration of the hydrogen atom between the exo- and endocyclic nitro­gen atoms can occur. This is evident from the presence of two tautomeric forms, viz. 3-imino-3H-isoindol-1-amine A and isoindoline-1,3-di­imine B (Fig. 1[link]), which, depending on whether they are in the solid state or in solution, the medium and the substituents on the exocyclic nitro­gen atoms, can occur both as the starting compound and as N,N′-disubstituted derivatives (Negrebetskii et al., 1983View full citation; Spiessens & Anteunis, 1984aView full citation; Zhang et al., 2004aView full citation).

[Figure 1]
Figure 1
Zwitterionic and tautomeric forms of compound 1.

Additionally, the presence of an exocyclic C=N double bond leads to the occurrence of Z/E isomerism (Negrebetskii et al., 1983View full citation; Spiessens & Anteunis, 1984bView full citation; Zhang et al., 2004bView full citation). In the solid state and in solution, both in the parent compound and in the N,N′-substituted derivatives, a significant polarization of the C=N bonds is realized, resulting in a significant contribution of the resonance structure C (Fig. 1[link]; Shishkin et al., 2013View full citation).

A series of N,N′-dialkyl-substituted derivatives were synthesized using Siegl's method from phthalo­nitrile and primary amines (Siegl, 1977View full citation; Tamgho et al., 2013View full citation). As part of our investigations into N,N′-disubstituted derivatives of 3-imino-3H-isoindol-1-amine, we synthesized the title compound, (Z)-N-allyl-3-(allyl­imino)-3H-isoindol-1-amine, C14H15N3 (1), by the reaction of 1,1,3-tri­chloro-1H-iso­indole with N-allyl­amine, and report here its mol­ecular and crystal structure.

[Scheme 1]

2. Structural commentary

Two mol­ecules (1a and 1b) are present in the asymmetric unit (Fig. 2[link]). Analysis of bond lengths in the –N3H—C8=N1—C1=N2– fragment (Table 1[link]) revealed that both mol­ecules exist in the tautomeric form A (Fig. 1[link]) in the crystal. The C1—N2 and N1—C8 bond lengths are close to the mean value of 1.313 Å for Csp2=N(2) bonds (Bürgi & Dunitz, 1994View full citation; the number in brackets indicates the number of bonds formed by the nitro­gen atom), while the C1—N1 and C8—N3 bonds are comparable to the mean values of Csp2–N(2) and Csp2–N(3) bonds (1.376 Å and 1.339 Å; Bürgi & Dunitz, 1994View full citation), respectively. Mol­ecules 1a and 1b differ in the conformation of their allyl substituents. In mol­ecule 1b, both allyl groups are arranged nearly orthogonal to the bicyclic fragment (the C1B—N2B—C9B—C10B and C8B—N3B—C12B—C13B torsion angles are −78.5 (3) and 82.1 (3)°). The terminal –Csp2=CH2 groups are rotated around the C9—C10 and C12—C13 single bonds [the N2B—C9B—C10B—C11B and N3B—C12B—C13B—C14B torsion angles are −116.6 (3) and 117.5 (4)°]. In mol­ecule 1a, both allyl groups are disordered over two sets of sites due to rotation around the N2A—C9A or N3A—C12A bonds. The ratio of the conformers a and c for the C9–C10–C11 allyl group is 0.372 (7):0.628 (7), while the ratio of the conformers a and c for the C12–C13–C14 allyl group is 0.755 (5):0.245 (5). In conformer 1a_a, the –Csp2=CH2 group is found in the ap-conformation relative to the C1A—N2A endocyclic bond and the C10=C11 double bond is turned in relation to the N2A—C9A bond [the C1A—N2A—C9A—C10A and N2A—C9A—C10A—C11A torsion angles are 175.7 (7) and −137 (1)°]. In conformer 1a_c, the –Csp2=CH2 fragment is found in the ac-conformation relative to the C1A—N2A endocyclic bond, and its double bond is rotated around the C9C—C10C bond [the C1A—N2A—C9C—C10C and N2A—C9C—C10C—C11C torsion angles are 137.1 (5) and 149.6 (7)°]. The –C13=C14 fragment is arranged orthogonal in the two conformers [1a_a and 1a_c, the C8A—N3A—C12A—C13A and C8A— N3A—C12A—C13C torsion angles are −81.6 (4) and −96.8 (7)°] and the double bond is rotated around the C12A—C13A/C13C bond [the N3A—C12A—C13A—C14A and N3A—C12A—C13C—C14C torsion angles are −14.4 (6) and 142 (2)°].

Table 1
Selected bond lengths (Å) in compound (I)

Bond Mol­ecule 1a Mol­ecule 1b
C1—N2 1.281 (3) 1.275 (3)
C1—N1 1.395 (3) 1.403 (4)
N1—C8 1.317 (3) 1.319 (3)
C8—N3 1.325 (3) 1.322 (3)
[Figure 2]
Figure 2
Mol­ecular structure of compound 1 with mol­ecules a and b present in the asymmetric unit (top row); displacement ellipsoids are drawn at the 50% probability level. Overlay of mol­ecules 1a_major_component/1b (left) and 1a_minor_component/1b (right); mol­ecule 1b is shown in blue, 1a_major_component in green and 1a_minor_component in red (bottom row).

3. Supra­molecular features

The title compound contains an NH group, which acts as a hydrogen donor, and two nitro­gen atoms, N1 and N2, which are capable of acting as hydrogen acceptors. However, one of these potential hydrogen acceptors, the N1 atom, is not available for hydrogen bonding due to the presence of bulky substituents at the neighboring atoms. As a result, only N3—H⋯N2 hydrogen bonds are found in the crystal (Table 2[link]). These bonds form infinite chains parallel to [001], in which mol­ecules 1a and 1b alternate (Fig. 3[link]). In addition to the classical N—H⋯N hydrogen bonds, only one weak C10—H⋯π(C6) inter­molecular inter­action is found in the crystal phase (Table 2[link]). Despite the presence of an electron-rich bicyclic moiety in the mol­ecule, no stacking inter­actions are observed in the crystal.

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C10A—H10A⋯C6Bi 0.93 2.74 3.571 (12) 149
N3A—H3AA⋯N2Bii 0.86 2.11 2.895 (3) 151
N3B—H3BA⋯N2Ai 0.86 2.15 2.951 (3) 154
Symmetry codes: (i) Mathematical equation; (ii) Mathematical equation.
[Figure 3]
Figure 3
Chains of mol­ecules 1a and 1b extending parallel to [001]. Inter­molecular hydrogen bonds N—H⋯N are shown as blue dashed lines.

4. Database survey

A search of the Cambridge Structure Database (CSD, version 6.00, last update April 2025; Groom et al., 2016View full citation) revealed 40 structures containing the 3-imino-3H-isoindol-1-amine fragment. The N,N′-unsubstituted derivatives of 3-imino-3H-isoindol-1-amine (structures EGAKIK, EGAKOQ (Al-Shewiki et al., 2024View full citation), EXUQAP, EXUQET (Zhang et al., 2004aView full citation), JARFAM (Lo & Ng, 2016View full citation), TIPVEV (Engle et al., 2013View full citation)) proved to be the closest to the compound under study. The distribution of electron density within the –NH–C=N—C=N– fragment is identical in all these structures.

5. Synthesis and crystallization

Compound 1 was synthesized according to a literature procedure (Hordiyenko et al., 2009View full citation, 2022View full citation). 1,1,3-Tri­chloro-1H-iso­indole (1.1 g, 5 mmol) was dissolved in anhydrous dioxane (5 ml), then N-allyl­amine (1.42 g, 25 mmol) was added dropwise upon stirring and cooling. A red oil formed, then the dioxane was evaporated under reduced pressure and the residual oil was washed with water (2 × 10 ml). After standing for one week in air, the oil crystallized in form of red crystals; yield 1.06 g (95%). Colourless single crystals were obtained by slow evaporation of a methano­lic solution of compound 1.

1H NMR spectrum (400 MHz, CDCl3), d, ppm (J, Hz), A form (93%): 4.42 (d, J = 5.2 Hz, 4H, CH2), 5.14 (d, J = 10.0 Hz, 2H, cis-CH=), 5.27 (d, J = 17.2 Hz, 2H, trans-CH=), 6.06 (m, 2H, CH2—CH=), 6.5 (br s, 1H, NH), 7.38 (m, 2H, CHAr), 7.38 (m, 2H, CHAr). 1H NMR spectrum (400 MHz, CDCl3), d, ppm (J, Hz), B form (7%): 4.33 (d, J = 5.2 Hz, 4H, CH2), 7.33 (d, J = 7.6 Hz, 1H, CHAr), 7.45–7.61 (m, 2H, CHAr), 7.83 (d, J = 8.4 Hz, 1H, CHAr).

1H NMR spectrum (400 MHz, DMSO-d6), d, ppm (J, Hz), A form (90%): 4.30 (br s, 4H, CH2), 5.86 (d, J = 10.0 Hz, 2H, cis-CH=), 5.23 (d, J = 16.8 Hz, 2H, trans-CH=), 5.99–6.06 (m, 2H, CH2-CH=), 7.48–7.50 (m, 2H, CHAr), 7.74–7.82 (m, 2H, CHAr). 1H NMR spectrum (400 MHz, CDCl3), d, ppm (J, Hz), B form (10%): 4.22 (br s, 4H, CH2), 5.86 (m, 2H, CH2—CH=), 7.69–7.71 (m, 2H, CHAr), 7.89 (m, 2H, CHAr).

13C NMR spectrum (100 MHz, CDCl3), d, ppm: 49.5 (CH2), 116.7, 117.6, 120.7, 121.9, 125.7, 129.4, 130.3, 135.0, 137.4, 167.1.

LC-MS: RT (min), m/z (%) = 0.951, 226.2 [68%, (M + H)+]; 1.019, 226.2 [21%, (M + H)+]. The presence of two independent peaks at m/z 226 but different retention times may be considered as a presence of two tautomeric forms A/B in a 3:1 ratio in solution during LS-MS analysis (RP C18, gradient elution of solvent H2O/CH3CN:1/99 to H2O/CH3CN:0/100, 0.1% formic acid). The 1H NMR spectra of compound 1 in CDCl3 and DMSO-d6 revealed two sets of resonances at room temperature corresponding to the A and B tautomers in a 90:10 ratio.

6. Refinement

Crystal data, data collection and structure refinement details are summarized in Table 3[link]. Hydrogen atoms were placed at calculated positions and refined as riding with Uiso(H) = 1.2Ueq(C/N). The site occupation factors of the disordered allyl groups of mol­ecule A were refined as 0.628 (7):0.372 (7) and 0.755 (5):0.245 (5). The restrictions on the bonds lengths in the disordered fragments were applied as Csp2—Csp3 = 1.510 (2) Å, N(2)—Csp3 = 1.470 (2) Å, Csp2=Csp2 = 1.340 (2) Å.

Table 3
Experimental details

Crystal data
Chemical formula C14H15N3
Mr 225.29
Crystal system, space group Triclinic, PMathematical equation
Temperature (K) 293
a, b, c (Å) 9.2429 (6), 11.1785 (8), 13.8791 (11)
α, β, γ (°) 73.461 (7), 87.231 (6), 67.950 (6)
V (Å3) 1271.36 (17)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.07
Crystal size (mm) 0.27 × 0.23 × 0.12
 
Data collection
Diffractometer Xcalibur, Sapphire3
Absorption correction Multi-scan (CrysAlis PRO; Rigaku OD, 2024View full citation)
Tmin, Tmax 0.806, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections 9706, 4463, 2711
Rint 0.024
(sin θ/λ)max (Å−1) 0.595
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.059, 0.190, 1.05
No. of reflections 4463
No. of parameters 324
No. of restraints 118
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.32, −0.25
Computer programs: CrysAlis PRO (Rigaku OD, 2024View full citation), SHELXT (Sheldrick, 2015aView full citation), SHELXL (Sheldrick, 2015bView full citation), Mercury (Macrae et al., 2020View full citation) and publCIF (Westrip, 2010View full citation).

Supporting information

CCDC reference: 2586660

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009448/wm5805sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989026009448/wm5805Isup3.hkl

checkCIF report


Computing details top

(Z)-N-(Prop-2-en-1-yl)-3-(prop-2-en-1-ylimino)isoindol-1-amine top
Crystal data top
C14H15N3Z = 4
Mr = 225.29F(000) = 480
Triclinic, P1Dx = 1.177 Mg m−3
a = 9.2429 (6) ÅMo Kα radiation, λ = 0.71073 Å
b = 11.1785 (8) ÅCell parameters from 3958 reflections
c = 13.8791 (11) Åθ = 3.1–32.5°
α = 73.461 (7)°µ = 0.07 mm−1
β = 87.231 (6)°T = 293 K
γ = 67.950 (6)°Bar, colourless
V = 1271.36 (17) Å30.27 × 0.23 × 0.12 mm
Data collection top
Xcalibur, Sapphire3
diffractometer		4463 independent reflections
Radiation source: Enhance (Mo) X-ray Source2711 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
Detector resolution: 16.1827 pixels mm-1θmax = 25.0°, θmin = 3.1°
ω scansh = −10→10
Absorption correction: multi-scan
(CrysAlisPro; Rigaku OD, 2024)		k = −13→13
Tmin = 0.806, Tmax = 1.000l = −16→14
9706 measured reflections
Refinement top
Refinement on F2118 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.059H-atom parameters constrained
wR(F2) = 0.190 w = 1/[σ2(Fo2) + (0.1125P)2 + 0.0092P]
where P = (Fo2 + 2Fc2)/3
S = 1.05(Δ/σ)max < 0.001
4463 reflectionsΔρmax = 0.32 e Å−3
324 parametersΔρmin = −0.25 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.

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 > 2σ(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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/UeqOcc. (<1)
C1A0.8690 (3)0.2668 (3)0.87377 (17)0.0533 (6)
C2A1.0230 (3)0.1639 (3)0.92144 (17)0.0498 (6)
C3A1.1469 (3)0.0757 (3)0.8868 (2)0.0654 (7)
H3A1.1453610.0723230.8207190.078*
C4A1.2744 (3)−0.0079 (3)0.9542 (2)0.0761 (8)
H4A1.360437−0.0679950.9324520.091*
C5A1.2771 (3)−0.0045 (3)1.0520 (2)0.0761 (8)
H5A1.364199−0.0626581.0954890.091*
C6A1.1526 (3)0.0840 (3)1.08696 (19)0.0625 (7)
H6A1.1541910.0869401.1531710.075*
C7A1.0260 (3)0.1675 (2)1.02036 (16)0.0498 (6)
C8A0.8735 (3)0.2710 (3)1.02921 (16)0.0501 (6)
C9A0.6704 (11)0.4090 (15)0.7545 (8)0.0947 (15)0.372 (7)
H9AA0.6732280.4854750.7730820.114*0.372 (7)
H9AB0.5920840.3808710.7925780.114*0.372 (7)
C9C0.6654 (5)0.3983 (8)0.7465 (6)0.0947 (15)0.628 (7)
H9CA0.6263430.4456300.7968380.114*0.628 (7)
H9CB0.5975340.3514830.7417570.114*0.628 (7)
C10A0.6249 (14)0.4511 (9)0.6435 (8)0.0758 (15)0.372 (7)
H10A0.6398870.3900990.6067220.091*0.372 (7)
C10C0.6553 (7)0.5003 (8)0.6464 (4)0.0758 (15)0.628 (7)
H10C0.7382940.5270230.6250140.091*0.628 (7)
C11A0.561 (2)0.5848 (9)0.6032 (16)0.118 (2)0.372 (7)
H11A0.5484190.6415110.6433130.142*0.372 (7)
H11B0.5287340.6210550.5350900.142*0.372 (7)
C11C0.5214 (10)0.5504 (9)0.5897 (8)0.118 (2)0.628 (7)
H11C0.4401440.5219940.6126750.142*0.628 (7)
H11D0.5095190.6136150.5272260.142*0.628 (7)
C12A0.6832 (3)0.4077 (3)1.1195 (2)0.0706 (8)
H12A0.6577820.3889531.1894090.085*0.755 (5)
H12B0.6049240.3974851.0818900.085*0.755 (5)
H12C0.6409080.3857691.1845470.085*0.245 (5)
H12D0.6074820.4233771.0667160.085*0.245 (5)
C13A0.6637 (5)0.5536 (3)1.0836 (4)0.0832 (13)0.755 (5)
H13A0.5639320.6205441.0733330.100*0.755 (5)
C13C0.7305 (18)0.5270 (9)1.1046 (15)0.0832 (13)0.245 (5)
H13C0.8280960.5011131.1366190.100*0.245 (5)
C14A0.7880 (6)0.5875 (6)1.0664 (4)0.1021 (16)0.755 (5)
H14A0.8879640.5207761.0765080.123*0.755 (5)
H14B0.7749270.6778291.0441970.123*0.755 (5)
C14C0.671 (2)0.6595 (10)1.0582 (12)0.1021 (16)0.245 (5)
H14C0.5733130.6986991.0231360.123*0.245 (5)
H14D0.7268390.7124781.0609400.123*0.245 (5)
N1A0.7836 (2)0.3261 (2)0.94508 (13)0.0565 (6)
N2A0.8244 (2)0.2976 (2)0.78095 (15)0.0697 (7)
N3A0.8308 (2)0.3045 (2)1.11342 (14)0.0602 (6)
H3AA0.8938660.2629791.1664020.072*
C1B0.9921 (3)0.7527 (2)0.62943 (17)0.0500 (6)
C2B1.1034 (3)0.8152 (2)0.58141 (17)0.0504 (6)
C3B1.1871 (3)0.8759 (3)0.6156 (2)0.0641 (7)
H3B1.1823570.8813740.6813320.077*
C4B1.2780 (3)0.9283 (3)0.5487 (2)0.0741 (8)
H4B1.3358510.9696570.5698660.089*
C5B1.2853 (3)0.9209 (3)0.4514 (2)0.0777 (9)
H5B1.3485510.9567360.4083880.093*
C6B1.2003 (3)0.8612 (3)0.4158 (2)0.0658 (7)
H6B1.2038700.8572060.3497270.079*
C7B1.1099 (3)0.8079 (2)0.48381 (17)0.0517 (6)
C8B1.0025 (3)0.7416 (2)0.47508 (16)0.0502 (6)
C9B0.8490 (3)0.6725 (3)0.75785 (19)0.0697 (8)
H9BA0.8607050.6402760.8308220.084*
H9BB0.8735320.5952170.7324860.084*
C10B0.6827 (3)0.7664 (3)0.7253 (2)0.0769 (9)
H10B0.6550080.7992530.6564900.092*
C11B0.5723 (4)0.8062 (4)0.7867 (2)0.1039 (12)
H11E0.5954190.7755510.8559430.125*
H11F0.4717580.8646970.7604680.125*
C12B0.8705 (3)0.6500 (3)0.3842 (2)0.0742 (8)
H12E0.8804300.5793680.4462710.089*
H12F0.8983130.6087660.3296840.089*
C13B0.7045 (3)0.7495 (3)0.3651 (2)0.0847 (9)
H13B0.6637170.7916530.4147330.102*
C14B0.6106 (5)0.7831 (5)0.2852 (2)0.1256 (16)
H14E0.6458660.7436820.2334350.151*
H14F0.5090750.8461470.2804470.151*
N1B0.9340 (2)0.7106 (2)0.55896 (14)0.0522 (5)
N2B0.9588 (2)0.7386 (2)0.72120 (14)0.0602 (6)
N3B0.9767 (2)0.7162 (2)0.39151 (15)0.0627 (6)
H3BA1.0246270.7398240.3392760.075*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C1A0.0485 (13)0.0702 (17)0.0390 (12)−0.0187 (12)0.0054 (9)−0.0179 (11)
C2A0.0461 (13)0.0585 (15)0.0442 (12)−0.0187 (11)0.0069 (9)−0.0162 (10)
C3A0.0592 (16)0.0738 (19)0.0588 (15)−0.0158 (14)0.0124 (12)−0.0265 (13)
C4A0.0556 (16)0.075 (2)0.0812 (19)−0.0059 (15)0.0107 (13)−0.0251 (15)
C5A0.0551 (16)0.082 (2)0.0680 (17)−0.0090 (15)−0.0064 (13)−0.0085 (15)
C6A0.0588 (15)0.0705 (18)0.0499 (14)−0.0187 (14)−0.0028 (11)−0.0117 (12)
C7A0.0487 (13)0.0586 (15)0.0434 (12)−0.0224 (12)0.0049 (9)−0.0139 (10)
C8A0.0521 (13)0.0601 (15)0.0383 (12)−0.0211 (12)0.0053 (10)−0.0151 (10)
C9A0.0527 (16)0.164 (4)0.0454 (17)−0.0086 (19)−0.0001 (12)−0.0402 (18)
C9C0.0527 (16)0.164 (4)0.0454 (17)−0.0086 (19)−0.0001 (12)−0.0402 (18)
C10A0.068 (3)0.076 (4)0.082 (2)−0.017 (3)−0.011 (2)−0.033 (3)
C10C0.068 (3)0.076 (4)0.082 (2)−0.017 (3)−0.011 (2)−0.033 (3)
C11A0.133 (6)0.092 (4)0.107 (4)−0.028 (4)−0.048 (3)−0.007 (4)
C11C0.133 (6)0.092 (4)0.107 (4)−0.028 (4)−0.048 (3)−0.007 (4)
C12A0.0700 (18)0.0767 (18)0.0576 (16)−0.0169 (15)0.0222 (13)−0.0260 (14)
C13A0.081 (4)0.075 (2)0.074 (3)−0.013 (2)0.005 (3)−0.017 (2)
C13C0.081 (4)0.075 (2)0.074 (3)−0.013 (2)0.005 (3)−0.017 (2)
C14A0.103 (4)0.081 (3)0.111 (3)−0.034 (3)0.002 (3)−0.011 (3)
C14C0.103 (4)0.081 (3)0.111 (3)−0.034 (3)0.002 (3)−0.011 (3)
N1A0.0505 (11)0.0710 (14)0.0400 (11)−0.0123 (11)0.0047 (8)−0.0187 (10)
N2A0.0534 (12)0.1011 (18)0.0439 (12)−0.0137 (12)0.0035 (9)−0.0261 (11)
N3A0.0615 (13)0.0763 (15)0.0399 (11)−0.0198 (12)0.0053 (9)−0.0211 (10)
C1B0.0462 (13)0.0520 (14)0.0451 (12)−0.0106 (11)0.0013 (10)−0.0146 (10)
C2B0.0408 (13)0.0518 (15)0.0506 (13)−0.0087 (11)−0.0001 (10)−0.0145 (11)
C3B0.0553 (16)0.0673 (18)0.0704 (17)−0.0195 (14)0.0000 (12)−0.0251 (14)
C4B0.0521 (16)0.0679 (19)0.102 (2)−0.0213 (15)0.0017 (15)−0.0256 (17)
C5B0.0523 (16)0.073 (2)0.092 (2)−0.0205 (15)0.0135 (14)−0.0051 (16)
C6B0.0507 (15)0.0722 (19)0.0605 (15)−0.0140 (14)0.0114 (12)−0.0120 (13)
C7B0.0383 (12)0.0535 (15)0.0501 (13)−0.0054 (11)0.0016 (9)−0.0113 (11)
C8B0.0426 (13)0.0551 (15)0.0430 (12)−0.0060 (11)0.0012 (10)−0.0161 (11)
C9B0.0729 (17)0.085 (2)0.0475 (14)−0.0314 (16)0.0082 (12)−0.0114 (13)
C10B0.0752 (18)0.095 (2)0.0640 (17)−0.0407 (18)0.0056 (14)−0.0159 (15)
C11B0.082 (2)0.143 (4)0.083 (2)−0.034 (2)0.0184 (18)−0.041 (2)
C12B0.0806 (19)0.078 (2)0.0699 (18)−0.0240 (16)0.0003 (14)−0.0380 (15)
C13B0.0755 (19)0.103 (3)0.085 (2)−0.0395 (19)0.0081 (16)−0.0331 (19)
C14B0.093 (3)0.179 (5)0.097 (3)−0.047 (3)−0.007 (2)−0.030 (3)
N1B0.0524 (12)0.0598 (13)0.0439 (10)−0.0181 (10)0.0036 (8)−0.0182 (9)
N2B0.0567 (13)0.0809 (16)0.0404 (11)−0.0228 (12)0.0039 (9)−0.0183 (10)
N3B0.0572 (13)0.0813 (16)0.0474 (12)−0.0194 (12)0.0056 (9)−0.0252 (11)
Geometric parameters (Å, º) top
C1A—C2A1.488 (3)C13C—H13C0.9300
C1A—N1A1.396 (3)C13C—C14C1.339 (2)
C1A—N2A1.281 (3)C14A—H14A0.9300
C2A—C3A1.372 (4)C14A—H14B0.9300
C2A—C7A1.387 (3)C14C—H14C0.9300
C3A—H3A0.9300C14C—H14D0.9300
C3A—C4A1.385 (4)N3A—H3AA0.8600
C4A—H4A0.9300C1B—C2B1.483 (3)
C4A—C5A1.372 (4)C1B—N1B1.403 (3)
C5A—H5A0.9300C1B—N2B1.275 (3)
C5A—C6A1.379 (4)C2B—C3B1.377 (4)
C6A—H6A0.9300C2B—C7B1.377 (3)
C6A—C7A1.374 (3)C3B—H3B0.9300
C7A—C8A1.476 (4)C3B—C4B1.377 (4)
C8A—N1A1.317 (3)C4B—H4B0.9300
C8A—N3A1.325 (3)C4B—C5B1.373 (4)
C9A—H9AA0.9700C5B—H5B0.9300
C9A—H9AB0.9700C5B—C6B1.386 (4)
C9A—C10A1.508 (2)C6B—H6B0.9300
C9A—N2A1.473 (2)C6B—C7B1.386 (3)
C9C—H9CA0.9700C7B—C8B1.472 (3)
C9C—H9CB0.9700C8B—N1B1.319 (3)
C9C—C10C1.507 (2)C8B—N3B1.322 (3)
C9C—N2A1.475 (2)C9B—H9BA0.9700
C10A—H10A0.9300C9B—H9BB0.9700
C10A—C11A1.338 (2)C9B—C10B1.5012 (19)
C10C—H10C0.9300C9B—N2B1.460 (3)
C10C—C11C1.337 (2)C10B—H10B0.9300
C11A—H11A0.9300C10B—C11B1.3254 (19)
C11A—H11B0.9300C11B—H11E0.9300
C11C—H11C0.9300C11B—H11F0.9300
C11C—H11D0.9300C12B—H12E0.9700
C12A—H12A0.9700C12B—H12F0.9700
C12A—H12B0.9700C12B—C13B1.5006 (19)
C12A—H12C0.9700C12B—N3B1.456 (3)
C12A—H12D0.9700C13B—H13B0.9300
C12A—C13A1.505 (2)C13B—C14B1.3178 (19)
C12A—C13C1.511 (2)C14B—H14E0.9300
C12A—N3A1.436 (3)C14B—H14F0.9300
C13A—H13A0.9300N3B—H3BA0.8600
C13A—C14A1.330 (2)
N1A—C1A—C2A109.48 (19)C13A—C14A—H14A120.0
N2A—C1A—C2A124.8 (2)C13A—C14A—H14B120.0
N2A—C1A—N1A125.7 (2)H14A—C14A—H14B120.0
C3A—C2A—C1A133.3 (2)C13C—C14C—H14C120.0
C3A—C2A—C7A120.8 (2)C13C—C14C—H14D120.0
C7A—C2A—C1A105.9 (2)H14C—C14C—H14D120.0
C2A—C3A—H3A121.3C8A—N1A—C1A106.5 (2)
C2A—C3A—C4A117.4 (3)C1A—N2A—C9A112.3 (5)
C4A—C3A—H3A121.3C1A—N2A—C9C118.0 (4)
C3A—C4A—H4A119.1C8A—N3A—C12A122.4 (2)
C5A—C4A—C3A121.7 (3)C8A—N3A—H3AA118.8
C5A—C4A—H4A119.1C12A—N3A—H3AA118.8
C4A—C5A—H5A119.5N1B—C1B—C2B109.3 (2)
C4A—C5A—C6A121.0 (3)N2B—C1B—C2B124.1 (2)
C6A—C5A—H5A119.5N2B—C1B—N1B126.5 (2)
C5A—C6A—H6A121.2C3B—C2B—C1B132.6 (2)
C7A—C6A—C5A117.6 (3)C7B—C2B—C1B106.2 (2)
C7A—C6A—H6A121.2C7B—C2B—C3B121.2 (2)
C2A—C7A—C8A104.9 (2)C2B—C3B—H3B121.2
C6A—C7A—C2A121.5 (2)C4B—C3B—C2B117.5 (3)
C6A—C7A—C8A133.6 (2)C4B—C3B—H3B121.2
N1A—C8A—C7A113.2 (2)C3B—C4B—H4B119.2
N1A—C8A—N3A123.3 (2)C5B—C4B—C3B121.6 (3)
N3A—C8A—C7A123.5 (2)C5B—C4B—H4B119.2
H9AA—C9A—H9AB108.0C4B—C5B—H5B119.3
C10A—C9A—H9AA109.3C4B—C5B—C6B121.5 (3)
C10A—C9A—H9AB109.3C6B—C5B—H5B119.3
N2A—C9A—H9AA109.3C5B—C6B—H6B121.7
N2A—C9A—H9AB109.3C7B—C6B—C5B116.7 (3)
N2A—C9A—C10A111.6 (6)C7B—C6B—H6B121.7
H9CA—C9C—H9CB107.6C2B—C7B—C6B121.6 (2)
C10C—C9C—H9CA108.7C2B—C7B—C8B105.2 (2)
C10C—C9C—H9CB108.7C6B—C7B—C8B133.1 (2)
N2A—C9C—H9CA108.7N1B—C8B—C7B113.1 (2)
N2A—C9C—H9CB108.7N1B—C8B—N3B123.4 (2)
N2A—C9C—C10C114.3 (5)N3B—C8B—C7B123.4 (2)
C9A—C10A—H10A123.3H9BA—C9B—H9BB107.9
C11A—C10A—C9A113.3 (14)C10B—C9B—H9BA109.3
C11A—C10A—H10A123.3C10B—C9B—H9BB109.3
C9C—C10C—H10C121.6N2B—C9B—H9BA109.3
C11C—C10C—C9C116.8 (7)N2B—C9B—H9BB109.3
C11C—C10C—H10C121.6N2B—C9B—C10B111.7 (2)
C10A—C11A—H11A120.0C9B—C10B—H10B117.4
C10A—C11A—H11B120.0C11B—C10B—C9B125.2 (3)
H11A—C11A—H11B120.0C11B—C10B—H10B117.4
C10C—C11C—H11C120.0C10B—C11B—H11E120.0
C10C—C11C—H11D120.0C10B—C11B—H11F120.0
H11C—C11C—H11D120.0H11E—C11B—H11F120.0
H12A—C12A—H12B106.9H12E—C12B—H12F108.1
H12C—C12A—H12D109.4C13B—C12B—H12E109.5
C13A—C12A—H12A107.3C13B—C12B—H12F109.5
C13A—C12A—H12B107.3N3B—C12B—H12E109.5
C13C—C12A—H12C111.6N3B—C12B—H12F109.5
C13C—C12A—H12D111.6N3B—C12B—C13B110.7 (2)
N3A—C12A—H12A107.3C12B—C13B—H13B116.7
N3A—C12A—H12B107.3C14B—C13B—C12B126.5 (3)
N3A—C12A—H12C111.6C14B—C13B—H13B116.7
N3A—C12A—H12D111.6C13B—C14B—H14E120.0
N3A—C12A—C13A120.0 (3)C13B—C14B—H14F120.0
N3A—C12A—C13C100.9 (7)H14E—C14B—H14F120.0
C12A—C13A—H13A119.7C8B—N1B—C1B106.1 (2)
C14A—C13A—C12A120.5 (4)C1B—N2B—C9B117.6 (2)
C14A—C13A—H13A119.7C8B—N3B—C12B122.8 (2)
C12A—C13C—H13C111.2C8B—N3B—H3BA118.6
C14C—C13C—C12A137.6 (13)C12B—N3B—H3BA118.6
C14C—C13C—H13C111.2
C1A—C2A—C3A—C4A−179.8 (3)N3A—C8A—N1A—C1A179.2 (2)
C1A—C2A—C7A—C6A179.7 (2)N3A—C12A—C13A—C14A−14.3 (7)
C1A—C2A—C7A—C8A0.7 (2)N3A—C12A—C13C—C14C142 (2)
C2A—C1A—N1A—C8A1.6 (3)C1B—C2B—C3B—C4B−177.9 (2)
C2A—C1A—N2A—C9A−176.4 (9)C1B—C2B—C7B—C6B178.1 (2)
C2A—C1A—N2A—C9C177.6 (5)C1B—C2B—C7B—C8B0.1 (2)
C2A—C3A—C4A—C5A0.6 (4)C2B—C1B—N1B—C8B0.7 (3)
C2A—C7A—C8A—N1A0.3 (3)C2B—C1B—N2B—C9B−178.8 (2)
C2A—C7A—C8A—N3A179.9 (2)C2B—C3B—C4B—C5B0.2 (4)
C3A—C2A—C7A—C6A0.2 (4)C2B—C7B—C8B—N1B0.4 (3)
C3A—C2A—C7A—C8A−178.8 (2)C2B—C7B—C8B—N3B−180.0 (2)
C3A—C4A—C5A—C6A−0.6 (5)C3B—C2B—C7B—C6B−0.1 (4)
C4A—C5A—C6A—C7A0.4 (4)C3B—C2B—C7B—C8B−178.0 (2)
C5A—C6A—C7A—C2A−0.2 (4)C3B—C4B—C5B—C6B0.5 (4)
C5A—C6A—C7A—C8A178.6 (3)C4B—C5B—C6B—C7B−0.9 (4)
C6A—C7A—C8A—N1A−178.6 (2)C5B—C6B—C7B—C2B0.7 (4)
C6A—C7A—C8A—N3A1.1 (4)C5B—C6B—C7B—C8B178.0 (3)
C7A—C2A—C3A—C4A−0.5 (4)C6B—C7B—C8B—N1B−177.3 (3)
C7A—C8A—N1A—C1A−1.2 (3)C6B—C7B—C8B—N3B2.4 (4)
C7A—C8A—N3A—C12A178.5 (2)C7B—C2B—C3B—C4B−0.4 (4)
C10A—C9A—N2A—C1A175.7 (11)C7B—C8B—N1B—C1B−0.7 (3)
C10C—C9C—N2A—C1A137.2 (6)C7B—C8B—N3B—C12B179.8 (2)
C13A—C12A—N3A—C8A−81.7 (4)C10B—C9B—N2B—C1B−78.5 (3)
C13C—C12A—N3A—C8A−96.9 (8)C13B—C12B—N3B—C8B82.1 (3)
N1A—C1A—C2A—C3A178.0 (3)N1B—C1B—C2B—C3B177.3 (3)
N1A—C1A—C2A—C7A−1.4 (3)N1B—C1B—C2B—C7B−0.5 (3)
N1A—C1A—N2A—C9A1.8 (9)N1B—C1B—N2B—C9B−0.1 (4)
N1A—C1A—N2A—C9C−4.2 (6)N1B—C8B—N3B—C12B−0.6 (4)
N1A—C8A—N3A—C12A−1.9 (4)N2B—C1B—C2B—C3B−3.8 (4)
N2A—C1A—C2A—C3A−3.6 (5)N2B—C1B—C2B—C7B178.4 (2)
N2A—C1A—C2A—C7A177.0 (2)N2B—C1B—N1B—C8B−178.2 (2)
N2A—C1A—N1A—C8A−176.8 (2)N2B—C9B—C10B—C11B−116.7 (4)
N2A—C9A—C10A—C11A−137.5 (15)N3B—C8B—N1B—C1B179.7 (2)
N2A—C9C—C10C—C11C149.7 (9)N3B—C12B—C13B—C14B117.5 (4)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C10A—H10A···C6Bi0.932.743.571 (12)149
N3A—H3AA···N2Bii0.862.112.895 (3)151
N3B—H3BA···N2Ai0.862.152.951 (3)154
Symmetry codes: (i) −x+2, −y+1, −z+1; (ii) −x+2, −y+1, −z+2.
Selected bond lengths (Å) in compound (I) top
BondMolecule 1aMolecule 1b
C1—N21.281 (3)1.275 (3)
C1—N11.395 (3)1.403 (4)
N1—C81.317 (3)1.319 (3)
C8—N31.325 (3)1.322 (3)
 

Acknowledgements

The authors are grateful to the FAIRE programme provided by the Cambridge Crystallographic Data Centre (CCDC) for the opportunity to use the Cambridge Structural Database (CSD) and associated software.

References

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Volume 82| Part 10| October 2026| Pages 1226-1229
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