N′-(2,6-Di­methyl­phen­yl)-N-phenyl­methanimidamide

Oubaha, I.; Saha, A.; Hanan, G.S.; Cibian, M.

doi:10.1107/S2414314625008673

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 10| Part 10| October 2025| x250867

https://doi.org/10.1107/S2414314625008673

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N′-(2,6-Dimethylphenyl)-N-phenylmethanimidamide

Ilyes Oubaha,^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 10 September 2025; accepted 3 October 2025; online 28 October 2025)

The title compound, C₁₆H₁₈N₂, is a non-symmetrically N,N′-disubstituted acetamidine having a phenyl and a bulky 2,6-dimethylphenyl as substituents on the two N atoms of the N—C—N linkage. It crystallizes in an E-syn configuration and its amidine C—N bonds present distinct amine [1.366 (1) Å] and imine [1.288 (1) Å] bond lengths. In the extended structure, strong N—H⋯N hydrogen bonds link the molecules into infinite C(4) chains propagating along the c-axis direction; weak C—H⋯π interactions are also present in the crystal packing.

Keywords: crystal structure; acetamidine; hydrogen bonding.

CCDC reference: 2492957

Structure description

The molecular structure of the title compound, C₁₆H₁₈N₂ (1) (Fig. 1) was determined at 100 K. Compound 1 was obtained as a result of a test reaction for synthesizing non-symmetrical amidines under microwave activation by sequential introduction of the N-substituents, with the final goal to serve as precursor for the corresponding amidine-N-oxide/hydroxyamidine derivative (Cibian et al., 2011 ; Saha et al., 2024 ). Although crystallographic evidence of various non-symmetric acetamidines with N,N′-bisarylamidines exists (e.g., Stibrany & Potenza, 2007 ; Peoples et al., 2012 ), this is the first report of 1, an acetamidine having a phenyl and a bulky 2,6-dimethylphenyl as substituents on the two N atoms of the N—C—N linkage. It crystallizes in the monoclinic P2₁/c space group, in the E-syn configuration (Kalz et al., 2016 ). Its amidine C—N bonds present distinct amine [1.366 (1) Å] and imine [1.288 (1) Å] bond lengths, as also found for N,N′-disubstituted arylamidine (Boeré et al., 1998 ; Cottin et al., 2021 ). The phenyl and 2,6-dimethylphenyl groups are positioned on the amine and imine N atoms, respectively.

Figure 1
The molecular structure of 1, with displacement ellipsoids drawn at 50% probability level.

In 1, the bulky substituted C9–C14 aryl ring and the C3–C8 phenyl ring subtend tilt angles of 85.3 (1) and 40.4 (1)°, respectively, with the N1—C1—N2 plane; the pendant rings are tilted by 64.3 (1)° with respect to each other. The C3—N1—C1—N2 and N1—C1—N2—C9 torsion angles are −11.33 (18) and 176.57 (10)°, respectively.

In the extended structure of 1 (Table 1 and Figs. 2 and 3), the molecules are linked by N—H⋯N strong hydrogen bonds (Desiraju & Steiner, 2001 ) between the amidine H1 proton and the N2 atom of the amidine unit in an adjacent molecule, thereby forming infinite C(4) chains of molecules propagating along the c-axis direction. Weak C—H⋯π interactions (Desiraju & Steiner, 2001) complete the crystal packing.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 and Cg2 are the centroids of the C3–C8 phenyl and C9–C14 2,6-dimethylphenyl rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯N2ⁱ	0.882 (15)	2.172 (15)	3.0530 (14)	176.3 (14)
C2—H2C⋯Cg1ⁱ	0.98	2.83	3.5601 (14)	132
C4—H4⋯Cg2ⁱ	0.95	2.59	3.5092 (13)	162
C15—H15A⋯Cg1ⁱⁱ	0.98	2.83	3.6346 (15)	140
Symmetry codes: (i) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x-1, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
Part of a [001] hydrogen-bonded chain in the extended structure of 1.

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

Synthesis and crystallization

A microwave vial was charged with 600 mg of 4 Å molecular sieves, triethylorthoacetate (1.5 ml, 8.18 mmol, 1 equiv.), 2 drops of acetic acid, and aniline (0.75 ml, 8.18 mmol, 1 equiv.). The reaction was conducted under microwave irradiation at 90 °C for 10 min. After cooling down, 2,6-dimethylanilline (1.01 ml, 8.18 mmol, 1 equiv.) was added to the crude reaction mixture and the reaction was continued at 90 °C for another 16 h. Part of the reaction mixture was taken in hexane (the molecular sieves were removed by filtration) and the solution was placed in the freezer (−10 °C). XRD-quality colorless crystals were obtained (0.50 g, 2.10 mmol, partial yield: 26% – only part of the product was purified).

¹H NMR (400 MHz, DMSO-d₆): 1.69 (s, 3H); 1.99 (s, 6H), 6.76 (t, J = 7.5 Hz, 1H), 6.91 (t, J = 7.3 Hz, 1H), 6.98 (d, J = 7.5 Hz, 2H), 7.25 (t, J = 7.5 Hz, 2H), 7.82 (d, J =7.9 Hz, 2H), 8.87 (s, 1H, NH). ¹³C NMR (100 MHz, DMSO-d₆): 17.9, 18.0, 118.7, 121.0, 121.1, 127.0, 127.5, 128.2, 141.4, 148.5, 152.2 (N—C=N). Elemental analysis C/H/N: calculated (%) for C₁₆H₁₈N₂: C 80.63, H 7.61, N 11.75; exp .: C 80.57, H 7.56, N 11.81. HRMS (ESI, positive): m/z [M + H]⁺ calculated: 239.15428; exp .: 239.15398 (diff. 1.25 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	C₁₆H₁₈N₂
M_r	238.32
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	100
a, b, c (Å)	7.2094 (1), 21.3517 (4), 8.9033 (2)
β (°)	95.418 (1)
V (Å³)	1364.39 (4)
Z	4
Radiation type	Cu Kα
μ (mm⁻¹)	0.53
Crystal size (mm)	0.21 × 0.04 × 0.01 × 0.01 (radius)

Data collection
Diffractometer	Bruker SMART APEXII CCD
Absorption correction	For a sphere (SADABS; Krause et al., 2015 )
T_min, T_max	0.807, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	21279, 2595, 2160
R_int	0.030
(sin θ/λ)_max (Å⁻¹)	0.613

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.113, 1.08
No. of reflections	2595
No. of parameters	170
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.28, −0.27
Computer programs: APEX2 (Bruker, 2009 ), SAINT (Bruker, 2020 ), SHELXT (Sheldrick, 2015a ), SHELXL (Sheldrick, 2015b ), OLEX2 (Dolomanov et al., 2009 ), ORTEP-3 for Windows (Farrugia, 2012 ), publCIF (Westrip, 2010 ), POV-RAY (POVRAY, 2013 ), PLATON (Spek, 2020 ) and Mercury (Macrae et al., 2020 ).

Structural data

CCDC reference: 2492957

Crystal structure: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008673/hb4536sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2414314625008673/hb4536Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S2414314625008673/hb4536Isup3.cml

checkCIF report

Computing details top

N'-(2,6-Dimethylphenyl)-N-phenylmethanimidamide top

Crystal data top

C₁₆H₁₈N₂	F(000) = 512
M_r = 238.32	D_x = 1.160 Mg m⁻³
Monoclinic, P2₁/c	Cu Kα radiation, λ = 1.54178 Å
a = 7.2094 (1) Å	Cell parameters from 7241 reflections
b = 21.3517 (4) Å	θ = 4.1–70.8°
c = 8.9033 (2) Å	µ = 0.53 mm⁻¹
β = 95.418 (1)°	T = 100 K
V = 1364.39 (4) Å³	Needle, colourless
Z = 4	0.21 × 0.04 × 0.01 × 0.01 (radius) mm

Data collection top

Bruker SMART APEXII CCD diffractometer	2595 independent reflections
Radiation source: microfocus sealed X-ray tube, Incoatec Iµs	2160 reflections with I > 2σ(I)
Mirror optics monochromator	R_int = 0.030
Detector resolution: 7.9 pixels mm^-1	θ_max = 71.0°, θ_min = 4.1°
ω and φ scans	h = −8→8
Absorption correction: for a sphere (SADABS; Krause et al., 2015)	k = −26→26
T_min = 0.807, T_max = 0.993	l = −10→10
21279 measured reflections

Refinement top

Refinement on F²	Primary atom site location: dual
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.038	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.113	w = 1/[σ²(F_o²) + (0.0716P)² + 0.0724P] where P = (F_o² + 2F_c²)/3
S = 1.08	(Δ/σ)_max < 0.001
2595 reflections	Δρ_max = 0.28 e Å⁻³
170 parameters	Δρ_min = −0.27 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.

Refinement. H atoms were included in calculated positions (C—H = 0.95–0.98 Å) and treated as riding atoms with U_iso(H) = 1.2U_eq(C) or 1.5U_eq(methyl C). 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
N1	0.67938 (14)	0.76538 (4)	1.09532 (11)	0.0191 (2)
H1	0.660 (2)	0.7773 (7)	1.1875 (16)	0.030 (4)*
N2	0.62606 (14)	0.68830 (4)	0.91279 (11)	0.0180 (2)
C1	0.61447 (16)	0.70782 (5)	1.04845 (12)	0.0174 (3)
C2	0.52870 (19)	0.67095 (6)	1.16869 (13)	0.0233 (3)
H2A	0.417882	0.648897	1.123623	0.035*
H2B	0.493168	0.699538	1.247175	0.035*
H2C	0.619298	0.640440	1.213416	0.035*
C3	0.79195 (17)	0.80654 (5)	1.01846 (12)	0.0185 (3)
C4	0.77137 (17)	0.87086 (5)	1.04025 (13)	0.0209 (3)
H4	0.677614	0.885791	1.099341	0.025*
C5	0.88698 (18)	0.91300 (6)	0.97613 (14)	0.0252 (3)
H5	0.873702	0.956622	0.993177	0.030*
C6	1.02225 (19)	0.89181 (6)	0.88702 (14)	0.0295 (3)
H6	1.101809	0.920649	0.843217	0.035*
C7	1.03948 (19)	0.82817 (7)	0.86297 (15)	0.0298 (3)
H7	1.130352	0.813541	0.800713	0.036*
C8	0.92670 (17)	0.78530 (6)	0.92795 (14)	0.0237 (3)
H8	0.941096	0.741724	0.910947	0.028*
C9	0.56482 (17)	0.62633 (5)	0.87387 (12)	0.0184 (3)
C10	0.38863 (17)	0.61776 (6)	0.79602 (13)	0.0218 (3)
C11	0.33856 (19)	0.55810 (6)	0.74243 (14)	0.0274 (3)
H11	0.219225	0.551720	0.689757	0.033*
C12	0.4601 (2)	0.50815 (6)	0.76486 (15)	0.0299 (3)
H12	0.424966	0.467915	0.726479	0.036*
C13	0.6326 (2)	0.51699 (6)	0.84329 (14)	0.0267 (3)
H13	0.714719	0.482358	0.859959	0.032*
C14	0.68861 (17)	0.57583 (6)	0.89848 (13)	0.0220 (3)
C15	0.25781 (19)	0.67238 (6)	0.76836 (16)	0.0292 (3)
H15A	0.134837	0.657116	0.728148	0.044*
H15B	0.306460	0.700987	0.695456	0.044*
H15C	0.246968	0.694588	0.863457	0.044*
C16	0.87995 (19)	0.58474 (6)	0.97859 (16)	0.0314 (3)
H16A	0.963149	0.551898	0.947325	0.047*
H16B	0.873019	0.582271	1.087825	0.047*
H16C	0.928376	0.625855	0.952801	0.047*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0265 (5)	0.0145 (5)	0.0167 (5)	−0.0016 (4)	0.0034 (4)	−0.0011 (4)
N2	0.0220 (5)	0.0134 (5)	0.0184 (5)	−0.0002 (4)	0.0011 (4)	0.0001 (4)
C1	0.0194 (6)	0.0135 (6)	0.0189 (6)	0.0017 (4)	0.0004 (4)	0.0014 (4)
C2	0.0329 (7)	0.0174 (6)	0.0201 (6)	−0.0040 (5)	0.0052 (5)	−0.0003 (4)
C3	0.0209 (6)	0.0173 (6)	0.0166 (6)	−0.0025 (4)	−0.0019 (5)	0.0011 (4)
C4	0.0260 (6)	0.0174 (6)	0.0187 (6)	−0.0006 (5)	−0.0007 (5)	−0.0001 (4)
C5	0.0333 (7)	0.0177 (6)	0.0236 (6)	−0.0055 (5)	−0.0027 (5)	0.0023 (4)
C6	0.0324 (7)	0.0292 (7)	0.0269 (7)	−0.0119 (6)	0.0027 (6)	0.0040 (5)
C7	0.0263 (7)	0.0335 (8)	0.0307 (7)	−0.0045 (6)	0.0081 (6)	−0.0017 (5)
C8	0.0237 (6)	0.0200 (6)	0.0275 (6)	0.0004 (5)	0.0027 (5)	−0.0014 (5)
C9	0.0261 (6)	0.0148 (6)	0.0148 (6)	−0.0012 (5)	0.0044 (5)	0.0005 (4)
C10	0.0262 (6)	0.0171 (6)	0.0223 (6)	−0.0005 (5)	0.0026 (5)	−0.0002 (4)
C11	0.0314 (7)	0.0216 (7)	0.0278 (7)	−0.0049 (5)	−0.0041 (5)	−0.0020 (5)
C12	0.0444 (8)	0.0156 (6)	0.0287 (7)	−0.0032 (6)	−0.0006 (6)	−0.0034 (5)
C13	0.0396 (8)	0.0150 (6)	0.0251 (6)	0.0051 (5)	0.0007 (6)	0.0007 (5)
C14	0.0292 (7)	0.0184 (6)	0.0184 (6)	0.0016 (5)	0.0022 (5)	0.0019 (4)
C15	0.0257 (7)	0.0249 (7)	0.0361 (8)	0.0019 (5)	−0.0023 (6)	−0.0032 (5)
C16	0.0322 (7)	0.0240 (7)	0.0368 (8)	0.0059 (5)	−0.0036 (6)	−0.0018 (5)

Geometric parameters (Å, º) top

N1—H1	0.882 (15)	C8—H8	0.9500
N1—C1	1.3663 (15)	C9—C10	1.4004 (17)
N1—C3	1.4157 (15)	C9—C14	1.4036 (16)
N2—C1	1.2879 (14)	C10—C11	1.3957 (17)
N2—C9	1.4272 (14)	C10—C15	1.5055 (17)
C1—C2	1.5078 (15)	C11—H11	0.9500
C2—H2A	0.9800	C11—C12	1.3826 (19)
C2—H2B	0.9800	C12—H12	0.9500
C2—H2C	0.9800	C12—C13	1.3810 (19)
C3—C4	1.3967 (16)	C13—H13	0.9500
C3—C8	1.3952 (17)	C13—C14	1.3946 (17)
C4—H4	0.9500	C14—C16	1.5040 (18)
C4—C5	1.3857 (17)	C15—H15A	0.9800
C5—H5	0.9500	C15—H15B	0.9800
C5—C6	1.3897 (19)	C15—H15C	0.9800
C6—H6	0.9500	C16—H16A	0.9800
C6—C7	1.3830 (19)	C16—H16B	0.9800
C7—H7	0.9500	C16—H16C	0.9800
C7—C8	1.3865 (18)

C1—N1—H1	117.7 (10)	C10—C9—N2	119.12 (10)
C1—N1—C3	127.32 (10)	C10—C9—C14	120.70 (11)
C3—N1—H1	114.6 (10)	C14—C9—N2	119.79 (11)
C1—N2—C9	118.81 (9)	C9—C10—C15	120.32 (11)
N1—C1—C2	113.86 (10)	C11—C10—C9	118.79 (11)
N2—C1—N1	121.80 (10)	C11—C10—C15	120.88 (12)
N2—C1—C2	124.34 (10)	C10—C11—H11	119.5
C1—C2—H2A	109.5	C12—C11—C10	120.98 (12)
C1—C2—H2B	109.5	C12—C11—H11	119.5
C1—C2—H2C	109.5	C11—C12—H12	120.1
H2A—C2—H2B	109.5	C13—C12—C11	119.72 (12)
H2A—C2—H2C	109.5	C13—C12—H12	120.1
H2B—C2—H2C	109.5	C12—C13—H13	119.4
C4—C3—N1	118.03 (11)	C12—C13—C14	121.21 (12)
C8—C3—N1	122.65 (11)	C14—C13—H13	119.4
C8—C3—C4	119.25 (11)	C9—C14—C16	121.20 (11)
C3—C4—H4	119.8	C13—C14—C9	118.58 (12)
C5—C4—C3	120.35 (12)	C13—C14—C16	120.20 (11)
C5—C4—H4	119.8	C10—C15—H15A	109.5
C4—C5—H5	119.8	C10—C15—H15B	109.5
C4—C5—C6	120.37 (12)	C10—C15—H15C	109.5
C6—C5—H5	119.8	H15A—C15—H15B	109.5
C5—C6—H6	120.4	H15A—C15—H15C	109.5
C7—C6—C5	119.10 (12)	H15B—C15—H15C	109.5
C7—C6—H6	120.4	C14—C16—H16A	109.5
C6—C7—H7	119.4	C14—C16—H16B	109.5
C6—C7—C8	121.28 (12)	C14—C16—H16C	109.5
C8—C7—H7	119.4	H16A—C16—H16B	109.5
C3—C8—H8	120.2	H16A—C16—H16C	109.5
C7—C8—C3	119.62 (12)	H16B—C16—H16C	109.5
C7—C8—H8	120.2

N1—C3—C4—C5	175.50 (11)	C5—C6—C7—C8	−1.1 (2)
N1—C3—C8—C7	−176.26 (11)	C6—C7—C8—C3	0.5 (2)
N2—C9—C10—C11	172.39 (10)	C8—C3—C4—C5	−1.79 (17)
N2—C9—C10—C15	−6.41 (17)	C9—N2—C1—N1	176.57 (10)
N2—C9—C14—C13	−172.50 (10)	C9—N2—C1—C2	−4.01 (17)
N2—C9—C14—C16	5.76 (17)	C9—C10—C11—C12	−0.21 (19)
C1—N1—C3—C4	149.38 (11)	C10—C9—C14—C13	0.23 (18)
C1—N1—C3—C8	−33.43 (18)	C10—C9—C14—C16	178.49 (11)
C1—N2—C9—C10	100.22 (13)	C10—C11—C12—C13	1.0 (2)
C1—N2—C9—C14	−86.95 (14)	C11—C12—C13—C14	−1.1 (2)
C3—N1—C1—N2	−11.33 (18)	C12—C13—C14—C9	0.53 (19)
C3—N1—C1—C2	169.20 (11)	C12—C13—C14—C16	−177.75 (12)
C3—C4—C5—C6	1.26 (18)	C14—C9—C10—C11	−0.38 (18)
C4—C3—C8—C7	0.89 (18)	C14—C9—C10—C15	−179.18 (11)
C4—C5—C6—C7	0.17 (19)	C15—C10—C11—C12	178.58 (12)

Hydrogen-bond geometry (Å, º) top

Cg1 and Cg2 are the centroids of the C3–C8 phenyl and C9–C14 2,6-dimethylphenyl rings, respectively.

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···N2ⁱ	0.882 (15)	2.172 (15)	3.0530 (14)	176.3 (14)
C2—H2C···Cg1ⁱ	0.98	2.83	3.5601 (14)	132
C4—H4···Cg2ⁱ	0.95	2.59	3.5092 (13)	162
C15—H15A···Cg1ⁱⁱ	0.98	2.83	3.6346 (15)	140

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

Acknowledgements

We thank the personnel from the XRD facilities of Université de Montréal. Professor Frank Schaper and Dr Daniel Chartrand are 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 (QCAM); 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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