N,N′-Bis([1,1′-biphen­yl]-2-yl)-N-hy­droxy­methanimidamide

Lamothe, E.; Saha, A.; Hanan, G.S.; Cibian, M.

doi:10.1107/S2414314625008314

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 9| September 2025| x250831

https://doi.org/10.1107/S2414314625008314

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N,N′-Bis([1,1′-biphenyl]-2-yl)-N-hydroxymethanimidamide

Elizabeth Lamothe,^a Arindam Saha,^a Garry S. Hanan ^a and Mihaela Cibian ^b ^*

^aDépartement de chimie, Université de Montréal, Complexe des Sciences, 1375 Avenue Thérèse-Lavoie-Roux, Montréal, Québec H2V 0B3, Canada, and ^bDépartement de biochimie, chimie, physique et science forensique and l'Institut de recherche sur l'hydrogène, Université du Québec à Trois-Rivières. 3351, boul. des Forges, CP 500, Trois-Rivières, Québec, G9A 5H7, Canada
^*Correspondence e-mail: [email protected]

Edited by W. T. A. Harrison, University of Aberdeen, United Kingdom (Received 9 September 2025; accepted 21 September 2025; online 30 September 2025)

The title compound, C₂₅H₂₀N₂O, crystallizes in the monoclinic C2/c space group, as the N-hydroxyformamidine isomer, in the E conformation (when referring to the C=N bond). Inversion dimers formed through pairwise O—H⋯N hydrogen bonds are present in the structure. C—H⋯π and π–π stacking interactions complete the crystal packing.

Keywords: crystal structure; amidine N-oxide; ligand synthesis.

CCDC reference: 2490088

Structure description

Colorless XRD-quality single crystals of the title compound, C₂₅H₂₀N₂O (1), were obtained and intensity data were collected at 100 K. The compound was synthesized as part of a project that explores the coordination chemistry of hydroxyamidine/amidine N-oxide ligands with transition metal ions to study the structures and properties of the resulting complexes (Verma et al., 1995 ; Cibian et al., 2015 ; Cibian & Hanan, 2015 ; Saha et al., 2024 ). Compound 1 crystallizes in the monoclinic C2/c space group as the N-hydroxyformamidine isomer, in the E conformation (when referring to the C1=N2 bond). The molecule is a symmetrically N,N′-disubstituted N-hydroxyformamidine, consisting of the N2—C1—N1—O1H core bearing a peripheral N-biphenyl substituent on each of the two N atoms. (Fig. 1). This is the first report of 1, but other crystallographic data on N-hydroxyformamidines/amidine N-oxides exist. Free ligands, having symmetrical (Cibian et al., 2009 ) and non-symmetrical (Giumanini et al., 1999 ) substitution, as well as coordination compounds of cobalt(II) (Cibian et al., 2015), zinc(II) (Cole et al., 2002 ), and copper(II) (Munzeiwa et al., 2021 ) have been reported. The bond lengths of the N—C—N—OH bridge in 1 are in line with those already reported for similar compounds crystallized as the N-hydroxyformamidine isomer form (Cibian et al., 2009).

Figure 1
View of the asymmetric unit of 1 with displacement ellipsoids drawn at the 50% probability level.

In 1, the bulky 2-biphenyl substituents have tilt angles of 54.0 (1) and 41.2 (1)^ο for the C2–C7 and C14–C19 rings, respectively, with respect to the N2–C1–N1 plane. The tilt angles within each of the 2-biphenyl moieties for the C2–C7/C8–C13 and C14–C19/C20–C25 rings are 48.6 (1) and 55.0 (1)^ο, respectively.

Geometric parameters of hydrogen bonds are reported in Table 1. The structure displays cyclic hydrogen-bonded dimers formed by pairwise O—H⋯N interactions (Fig. 2), which generate R₂²(10) loops. The crystal is efficiently packed (Fig. 3) by additional C—H⋯O and C—H⋯π interactions as well as by multiple π–π stacking interactions involving the 2-biphenyl substituents.

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O1—H1⋯N2ⁱ	0.84	1.91	2.7425 (18)	174
C12—H12⋯O1ⁱⁱ	0.95	2.54	3.330 (2)	141
C19—H19⋯Cg2	0.95	2.93	3.8724 (19)	173
C22—H22⋯Cg2ⁱⁱⁱ	0.95	2.89	3.616 (2)	134
Symmetry codes: (i) $[-x+1, y, -z+{\script{1\over 2}}]$ ; (ii) $[-x+{\script{1\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (iii) $[-x+{\script{1\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

Figure 2
Intermolecular hydrogen bonding between two molecules of 1 in the unit cell. Symmetry code: (i) −x + 1, y, −z + $[{1\over 2}]$ .

Figure 3
View of the packing of 1 in the unit cell.

Synthesis and crystallization

Compound 1 was obtained from the oxidation of N,N′-bis(2-diphenyl)formamidine (Cibian et al., 2011 ) with m-chloroperoxybenzoic acid (m-CPBA). N,N′-bis(2-diphenyl)formamidine (1.5 g, 4.3 mmol, 1 equiv.) and NaHCO₃ (0.38 g, 4.3 mmol, 1equiv.) in DCM (50 mL) were combined with m-CPBA (0.96 g, 4.3 mmol, 1 equiv.) in an ice/ methanol bath at −10 °C and stirred for 30–60 minutes, to arrive at room temperature. Liquid–liquid extraction was performed with aqueous K₂CO₃ (5%, 2 × 25 mL) and the combined organic layers were dried over anhydrous Na₂SO₄. Following filtration and solvent evaporation, a colorless solid was obtained, which was further purified by flash chromatography on silica (gradient of eluents: hexane/EtOAc (2:8), EtOAc/MeOH (9:1), DCM 100%). Recrystallization from a solvent mixture of DCM/hexane (1:1) resulted in colorless plates.

Yield: 0.93 g, 59%. ¹H-NMR (CDCl3, 400 MHz), p.p.m.: 7.85–7.78 (m, 1H, –C₆H₄), 7.55–7.32 (m, 14H, –C₆H₅, –C₆H₄, and –NH—CH=N–), 7.21 (dd, J = 7, 2 Hz, 1H, –C₆H₄), 7.11 (td, J = 8, 2 Hz, 1H, –C₆H₄), 7.05 (td, J = 7, 1 Hz, 1H, –C₆H₄), 6.17 (d, J = 8 Hz, 1H, –C₆H₄), 3.67 (bs, OH). ¹³C {¹H} NMR (CDCl3, 75 MHz) δ, p.p.m.: 142.0, 138.2, 137.5, 136.9, 135.7, 135.2, 131.7, 131.4, 130.7, 129.4 (2 C), 129.24 (2 C), 129.19 (2 C), 129.1 (2 C), 128.8, 128.6, 128.5 (2 C), 128.3, 128.1, 126.1, 123.7, 115.4. Elemental analysis: calculated (%) for C₂₅H₂₀N₂O: C 82.39, H 5.53, N 7.69; found: C 82.33, H 5.52, N 7.73. HRMS (ESI positive, DCM) (m/z): [M+H]⁺ C₂₅H₂₁N₂O: calculated 365.1648; found 365.1655 (diff. 1.92 p.p.m.)

Refinement

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

Table 2
Experimental details

Crystal data
Chemical formula	C₂₅H₂₀N₂O
M_r	364.43
Crystal system, space group	Monoclinic, C2/c
Temperature (K)	100
a, b, c (Å)	10.0344 (4), 16.8774 (6), 22.9241 (9)
β (°)	100.129 (2)
V (Å³)	3821.8 (3)
Z	8
Radiation type	Cu Kα
μ (mm⁻¹)	0.61
Crystal size (mm)	0.18 × 0.10 × 0.05

Data collection
Diffractometer	Bruker Microstar
Absorption correction	Multi-scan (SADABS; Krause et al., 2015 )
T_min, T_max	0.649, 0.753
No. of measured, independent and observed [I > 2σ(I)] reflections	41862, 3579, 2963
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.608

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.132, 1.05
No. of reflections	3579
No. of parameters	254
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.24, −0.22
Computer programs: APEX2 2 (Bruker, 2009 ),and SAINT (Bruker, 2009), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), ORTEP-3 for Windows (Farrugia, 2012 ), publCIF (Westrip, 2010 ), POVRAY (POVRAY, 2013 ), PLATON (Spek, 2020 ) and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2490088

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008314/hb4535sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008314/hb4535Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625008314/hb4535Isup3.cml

checkCIF report

Computing details top

N,N'-Bis([1,1'-biphenyl]-2-yl)-N-hydroxymethanimidamide top

Crystal data top

C₂₅H₂₀N₂O	F(000) = 1536
M_r = 364.43	D_x = 1.267 Mg m⁻³
Monoclinic, C2/c	Cu Kα radiation, λ = 1.54178 Å
a = 10.0344 (4) Å	Cell parameters from 9920 reflections
b = 16.8774 (6) Å	θ = 3.9–69.2°
c = 22.9241 (9) Å	µ = 0.61 mm⁻¹
β = 100.129 (2)°	T = 100 K
V = 3821.8 (3) Å³	Plate, colourless
Z = 8	0.18 × 0.10 × 0.05 mm

Data collection top

Bruker Microstar diffractometer	3579 independent reflections
Radiation source: Rotating Anode, Incoatec Iµs	2963 reflections with I > 2σ(I)
Helios Optics monochromator	R_int = 0.054
Detector resolution: 8.3 pixels mm^-1	θ_max = 69.6°, θ_min = 3.9°
ω scans	h = −12→12
Absorption correction: multi-scan (SADABS; Krause et al., 2015)	k = −20→14
T_min = 0.649, T_max = 0.753	l = −27→27
41862 measured 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)] = 0.046	H-atom parameters constrained
wR(F²) = 0.132	w = 1/[σ²(F_o²) + (0.0645P)² + 2.7528P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
3579 reflections	Δρ_max = 0.24 e Å⁻³
254 parameters	Δρ_min = −0.22 e Å⁻³
0 restraints

Special details top

Experimental. Crystallographic data for the title compound were collected at 150 K, from single crystal samples, which were mounted on a loop fiber. Data were collected using a Bruker Microstar diffractometer equipped with a Platinum 135 CCD Detector, a Helios optics and a Kappa goniometer. The crystal-to-detector distance was 3.8 cm, and the data collection was carried out in 512 x 512 pixel mode. The initial unit cell parameters were determined by a least-squares fit of the angular setting of strong reflections, collected by a 110.0 degree scan in 110 frames over three different parts of the reciprocal space.

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. The H-atoms were included in calculated positions and treated as riding atoms: aromatic C—H 0.95 Å, methyl C—H 0.98 Å, with U_iso(H) = k × U_eq (parent C-atom), where k = 1.2 for the aromatic H-atoms and 1.5 for the methyl H-atoms. The NH proton (H1) was located in the difference-Fourier map and refined freely.

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

	x	y	z	U_iso*/U_eq
O1	0.41250 (11)	0.32719 (6)	0.29426 (5)	0.0398 (3)
H1	0.487036	0.350885	0.297375	0.060*
N1	0.30822 (14)	0.38176 (8)	0.28406 (6)	0.0379 (3)
N2	0.35221 (14)	0.41337 (8)	0.19030 (6)	0.0361 (3)
C1	0.27878 (17)	0.41737 (10)	0.23132 (7)	0.0371 (4)
H1A	0.198039	0.447860	0.223343	0.045*
C2	0.21963 (17)	0.38428 (10)	0.32616 (7)	0.0379 (4)
C3	0.17421 (16)	0.45749 (10)	0.34487 (7)	0.0368 (4)
C4	0.07812 (17)	0.45541 (11)	0.38246 (8)	0.0430 (4)
H4	0.044016	0.503796	0.395085	0.052*
C5	0.03203 (19)	0.38461 (13)	0.40153 (8)	0.0498 (5)
H5	−0.034076	0.384726	0.426541	0.060*
C6	0.0817 (2)	0.31343 (12)	0.38437 (8)	0.0507 (5)
H6	0.051431	0.264855	0.398434	0.061*
C7	0.17569 (19)	0.31302 (11)	0.34661 (8)	0.0453 (4)
H7	0.209887	0.264218	0.334774	0.054*
C8	0.22422 (17)	0.53539 (10)	0.32721 (7)	0.0360 (4)
C9	0.36197 (17)	0.55092 (10)	0.33192 (8)	0.0414 (4)
H9	0.426106	0.511068	0.346483	0.050*
C10	0.40633 (19)	0.62414 (10)	0.31553 (9)	0.0469 (4)
H10	0.500591	0.634216	0.319262	0.056*
C11	0.3145 (2)	0.68237 (10)	0.29386 (8)	0.0473 (4)
H11	0.345298	0.732036	0.281965	0.057*
C12	0.1778 (2)	0.66831 (11)	0.28951 (8)	0.0478 (4)
H12	0.114173	0.708443	0.274939	0.057*
C13	0.13330 (18)	0.59558 (10)	0.30641 (8)	0.0418 (4)
H13	0.038977	0.586569	0.303762	0.050*
C14	0.31214 (16)	0.46457 (10)	0.14107 (7)	0.0354 (4)
C15	0.32779 (16)	0.44001 (10)	0.08413 (7)	0.0386 (4)
C16	0.29510 (19)	0.49359 (12)	0.03720 (8)	0.0478 (4)
H16	0.305598	0.477661	−0.001484	0.057*
C17	0.2482 (2)	0.56875 (12)	0.04542 (9)	0.0510 (5)
H17	0.226304	0.603840	0.012735	0.061*
C18	0.23304 (19)	0.59280 (11)	0.10161 (9)	0.0470 (4)
H18	0.199880	0.644356	0.107556	0.056*
C19	0.26629 (17)	0.54164 (10)	0.14911 (8)	0.0401 (4)
H19	0.257936	0.558969	0.187735	0.048*
C20	0.37440 (18)	0.35899 (11)	0.07169 (7)	0.0422 (4)
C21	0.30844 (19)	0.29159 (11)	0.08680 (8)	0.0444 (4)
H21	0.236982	0.297108	0.108734	0.053*
C22	0.3445 (2)	0.21663 (12)	0.07064 (8)	0.0548 (5)
H22	0.296122	0.171615	0.080504	0.066*
C23	0.4499 (3)	0.20719 (15)	0.04039 (9)	0.0651 (6)
H23	0.474305	0.155829	0.028963	0.078*
C24	0.5199 (2)	0.27266 (17)	0.02675 (10)	0.0678 (7)
H24	0.595571	0.265921	0.007465	0.081*
C25	0.4816 (2)	0.34917 (14)	0.04082 (9)	0.0559 (5)
H25	0.528175	0.394049	0.029472	0.067*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0386 (6)	0.0317 (6)	0.0490 (7)	0.0005 (5)	0.0076 (5)	0.0014 (5)
N1	0.0427 (8)	0.0330 (7)	0.0391 (8)	0.0047 (6)	0.0098 (6)	0.0020 (6)
N2	0.0396 (7)	0.0351 (7)	0.0339 (7)	0.0003 (6)	0.0073 (6)	−0.0008 (6)
C1	0.0410 (9)	0.0340 (8)	0.0361 (8)	−0.0005 (7)	0.0058 (7)	−0.0029 (7)
C2	0.0402 (9)	0.0386 (9)	0.0348 (8)	−0.0035 (7)	0.0062 (7)	0.0000 (7)
C3	0.0360 (8)	0.0411 (9)	0.0327 (8)	−0.0002 (7)	0.0048 (7)	−0.0009 (7)
C4	0.0375 (9)	0.0536 (11)	0.0375 (9)	0.0006 (8)	0.0057 (7)	−0.0008 (8)
C5	0.0421 (10)	0.0689 (13)	0.0391 (10)	−0.0100 (9)	0.0094 (8)	0.0037 (9)
C6	0.0541 (11)	0.0539 (11)	0.0443 (10)	−0.0156 (9)	0.0092 (8)	0.0068 (8)
C7	0.0529 (11)	0.0396 (10)	0.0431 (10)	−0.0061 (8)	0.0076 (8)	0.0030 (7)
C8	0.0406 (9)	0.0348 (8)	0.0334 (8)	0.0022 (7)	0.0081 (7)	−0.0041 (6)
C9	0.0402 (9)	0.0353 (9)	0.0484 (10)	0.0029 (7)	0.0072 (8)	−0.0006 (7)
C10	0.0452 (10)	0.0394 (10)	0.0563 (11)	−0.0052 (8)	0.0098 (8)	−0.0033 (8)
C11	0.0615 (12)	0.0335 (9)	0.0472 (10)	−0.0014 (8)	0.0107 (9)	−0.0004 (7)
C12	0.0566 (11)	0.0377 (9)	0.0483 (10)	0.0112 (8)	0.0073 (8)	0.0003 (8)
C13	0.0408 (9)	0.0425 (9)	0.0418 (9)	0.0059 (7)	0.0063 (7)	−0.0019 (7)
C14	0.0318 (8)	0.0379 (9)	0.0363 (8)	−0.0019 (6)	0.0049 (6)	0.0019 (7)
C15	0.0337 (8)	0.0451 (9)	0.0367 (9)	−0.0018 (7)	0.0052 (7)	0.0015 (7)
C16	0.0488 (10)	0.0557 (11)	0.0386 (10)	0.0005 (9)	0.0074 (8)	0.0052 (8)
C17	0.0540 (11)	0.0518 (11)	0.0448 (10)	−0.0014 (9)	0.0020 (8)	0.0130 (9)
C18	0.0475 (10)	0.0392 (10)	0.0518 (11)	0.0012 (8)	0.0023 (8)	0.0052 (8)
C19	0.0399 (9)	0.0395 (9)	0.0406 (9)	−0.0021 (7)	0.0059 (7)	−0.0005 (7)
C20	0.0399 (9)	0.0541 (11)	0.0315 (8)	0.0098 (8)	0.0033 (7)	−0.0023 (7)
C21	0.0514 (10)	0.0457 (10)	0.0355 (9)	0.0113 (8)	0.0059 (8)	0.0005 (7)
C22	0.0723 (13)	0.0504 (11)	0.0389 (10)	0.0189 (10)	0.0022 (9)	−0.0034 (8)
C23	0.0765 (15)	0.0682 (15)	0.0468 (12)	0.0286 (12)	0.0003 (11)	−0.0116 (10)
C24	0.0560 (13)	0.0987 (19)	0.0494 (12)	0.0254 (13)	0.0111 (10)	−0.0201 (12)
C25	0.0484 (11)	0.0769 (14)	0.0436 (11)	0.0063 (10)	0.0115 (9)	−0.0071 (10)

Geometric parameters (Å, º) top

O1—H1	0.8400	C12—H12	0.9500
O1—N1	1.3826 (17)	C12—C13	1.384 (3)
N1—C1	1.336 (2)	C13—H13	0.9500
N1—C2	1.423 (2)	C14—C15	1.405 (2)
N2—C1	1.294 (2)	C14—C19	1.403 (2)
N2—C14	1.422 (2)	C15—C16	1.400 (2)
C1—H1A	0.9500	C15—C20	1.489 (2)
C2—C3	1.410 (2)	C16—H16	0.9500
C2—C7	1.390 (2)	C16—C17	1.377 (3)
C3—C4	1.402 (2)	C17—H17	0.9500
C3—C8	1.489 (2)	C17—C18	1.384 (3)
C4—H4	0.9500	C18—H18	0.9500
C4—C5	1.380 (3)	C18—C19	1.384 (3)
C5—H5	0.9500	C19—H19	0.9500
C5—C6	1.384 (3)	C20—C21	1.390 (3)
C6—H6	0.9500	C20—C25	1.398 (3)
C6—C7	1.388 (3)	C21—H21	0.9500
C7—H7	0.9500	C21—C22	1.384 (3)
C8—C9	1.392 (2)	C22—H22	0.9500
C8—C13	1.392 (2)	C22—C23	1.372 (3)
C9—H9	0.9500	C23—H23	0.9500
C9—C10	1.388 (2)	C23—C24	1.375 (4)
C10—H10	0.9500	C24—H24	0.9500
C10—C11	1.379 (3)	C24—C25	1.401 (3)
C11—H11	0.9500	C25—H25	0.9500
C11—C12	1.378 (3)

N1—O1—H1	109.5	C13—C12—H12	120.1
O1—N1—C2	116.72 (13)	C8—C13—H13	119.4
C1—N1—O1	119.54 (13)	C12—C13—C8	121.25 (17)
C1—N1—C2	122.36 (14)	C12—C13—H13	119.4
C1—N2—C14	115.29 (14)	C15—C14—N2	119.73 (15)
N1—C1—H1A	117.6	C19—C14—N2	120.84 (15)
N2—C1—N1	124.78 (16)	C19—C14—C15	119.26 (15)
N2—C1—H1A	117.6	C14—C15—C20	122.64 (15)
C3—C2—N1	120.43 (14)	C16—C15—C14	118.31 (16)
C7—C2—N1	118.41 (15)	C16—C15—C20	119.03 (16)
C7—C2—C3	121.13 (16)	C15—C16—H16	119.0
C2—C3—C8	123.30 (14)	C17—C16—C15	121.97 (17)
C4—C3—C2	117.33 (15)	C17—C16—H16	119.0
C4—C3—C8	119.37 (15)	C16—C17—H17	120.2
C3—C4—H4	119.3	C16—C17—C18	119.57 (17)
C5—C4—C3	121.42 (17)	C18—C17—H17	120.2
C5—C4—H4	119.3	C17—C18—H18	120.0
C4—C5—H5	119.9	C19—C18—C17	119.91 (18)
C4—C5—C6	120.28 (17)	C19—C18—H18	120.0
C6—C5—H5	119.9	C14—C19—H19	119.5
C5—C6—H6	120.0	C18—C19—C14	120.96 (17)
C5—C6—C7	119.98 (17)	C18—C19—H19	119.5
C7—C6—H6	120.0	C21—C20—C15	121.63 (15)
C2—C7—H7	120.1	C21—C20—C25	118.15 (18)
C6—C7—C2	119.77 (17)	C25—C20—C15	120.10 (18)
C6—C7—H7	120.1	C20—C21—H21	119.2
C9—C8—C3	121.52 (15)	C22—C21—C20	121.53 (18)
C9—C8—C13	118.10 (16)	C22—C21—H21	119.2
C13—C8—C3	120.37 (15)	C21—C22—H22	119.9
C8—C9—H9	119.7	C23—C22—C21	120.2 (2)
C10—C9—C8	120.54 (16)	C23—C22—H22	119.9
C10—C9—H9	119.7	C22—C23—H23	120.3
C9—C10—H10	119.8	C22—C23—C24	119.5 (2)
C11—C10—C9	120.42 (17)	C24—C23—H23	120.3
C11—C10—H10	119.8	C23—C24—H24	119.4
C10—C11—H11	120.1	C23—C24—C25	121.1 (2)
C12—C11—C10	119.81 (17)	C25—C24—H24	119.4
C12—C11—H11	120.1	C20—C25—C24	119.5 (2)
C11—C12—H12	120.1	C20—C25—H25	120.2
C11—C12—C13	119.86 (17)	C24—C25—H25	120.2

O1—N1—C1—N2	−10.0 (2)	C8—C9—C10—C11	−0.5 (3)
O1—N1—C2—C3	138.89 (15)	C9—C8—C13—C12	1.5 (3)
O1—N1—C2—C7	−43.3 (2)	C9—C10—C11—C12	1.2 (3)
N1—C2—C3—C4	174.64 (15)	C10—C11—C12—C13	−0.6 (3)
N1—C2—C3—C8	−6.0 (2)	C11—C12—C13—C8	−0.8 (3)
N1—C2—C7—C6	−175.36 (16)	C13—C8—C9—C10	−0.8 (3)
N2—C14—C15—C16	−176.18 (15)	C14—N2—C1—N1	−171.55 (15)
N2—C14—C15—C20	5.3 (2)	C14—C15—C16—C17	−0.2 (3)
N2—C14—C19—C18	177.06 (15)	C14—C15—C20—C21	55.2 (2)
C1—N1—C2—C3	−54.6 (2)	C14—C15—C20—C25	−128.83 (19)
C1—N1—C2—C7	123.20 (18)	C15—C14—C19—C18	1.7 (2)
C1—N2—C14—C15	−145.85 (15)	C15—C16—C17—C18	0.3 (3)
C1—N2—C14—C19	38.8 (2)	C15—C20—C21—C22	174.29 (17)
C2—N1—C1—N2	−176.13 (15)	C15—C20—C25—C24	−176.74 (18)
C2—C3—C4—C5	1.4 (3)	C16—C15—C20—C21	−123.26 (19)
C2—C3—C8—C9	−48.9 (2)	C16—C15—C20—C25	52.7 (2)
C2—C3—C8—C13	132.29 (18)	C16—C17—C18—C19	0.6 (3)
C3—C2—C7—C6	2.4 (3)	C17—C18—C19—C14	−1.6 (3)
C3—C4—C5—C6	0.9 (3)	C19—C14—C15—C16	−0.8 (2)
C3—C8—C9—C10	−179.61 (16)	C19—C14—C15—C20	−179.29 (16)
C3—C8—C13—C12	−179.70 (16)	C20—C15—C16—C17	178.35 (17)
C4—C3—C8—C9	130.37 (18)	C20—C21—C22—C23	1.8 (3)
C4—C3—C8—C13	−48.4 (2)	C21—C20—C25—C24	−0.7 (3)
C4—C5—C6—C7	−1.7 (3)	C21—C22—C23—C24	0.5 (3)
C5—C6—C7—C2	0.0 (3)	C22—C23—C24—C25	−2.9 (3)
C7—C2—C3—C4	−3.1 (2)	C23—C24—C25—C20	3.0 (3)
C7—C2—C3—C8	176.24 (16)	C25—C20—C21—C22	−1.7 (3)
C8—C3—C4—C5	−177.91 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O1—H1···N2ⁱ	0.84	1.91	2.7425 (18)	174
C12—H12···O1ⁱⁱ	0.95	2.54	3.330 (2)	141
C19—H19···Cg2	0.95	2.93	3.8724 (19)	173
C22—H22···Cg2ⁱⁱⁱ	0.95	2.89	3.616 (2)	134

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

Acknowledgements

We thank the personnel from the XRD facilities of Université de Montréal for access and guidance. Professor Frank Schaper, Dr Michel Simard, Dr Thierry Maris, and Dr Daniel Chartrand are specially acknowledged for the crystallographic course and training.

Funding information

Funding for this research was provided by: Natural Sciences and Engineering Research Council of Canada (NSERC); Fonds de recherche du Québec – Nature et technologies (FRQ-NT); Quebec Centre for Advanced Materials (CQMF); Centre in Green Chemistry and Catalysis (CGCC); Université de Montréal (UdeM); Université du Québec à Trois-Rivières (UQTR); l'Institut de recherche sur l'hydrogène (IRH).

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