N-Cyclo-hexyl-3-methyl-benzamidine.

The title amidine compound, C14H20N2, prepared by a one-pot reaction, is asymmetric as only one N atom has an alkyl substituent. The terminal cyclo-hexyl group connected to the amino N atom is located on the other side of the N-C-N skeleton to the 4-methylbenzene ring and has a chair conformation. The dihedral angle between the phenyl ring and the NCN plane is 47.87 (12)°. In the crystal, mol-ecules are linked via N-H⋯N hydrogen bonds, forming chains propagating along the a-axis direction.

Related literature

For reviews of related metal amidinates and their applications in n class="Chemical">olefin polymerization, see: Edelmann (1994 ▶); Barker & Kilner (1994 ▶); Collins (2011 ▶); Bai et al. (2010 ▶); Yang et al. (2013 ▶). For a review of neutral amidines, see: Coles (2006 ▶). For a related synthetic method for amidines, see: Wang et al. (2008 ▶). For related silyl-linked bis­(amidinate) ligands, see: Bai et al. (2006 ▶).

Experimental

Crystal data

C14H20N2

M = 216.32

Orthorhombic,

a = 9.064 (2) Å

b = 11.417 (3) Å

c = 12.311 (3) Å

V = 1274.0 (5) Å3

Z = 4

Mo Kα radiation

μ = 0.07 mm−1

T = 200 K

0.30 × 0.25 × 0.20 mm

Data collection

Bruker SMART CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.980, T max = 0.987

7147 measured reflections

2244 independent reflections

1758 reflections with I > 2σ(I)

R int = 0.042

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.098

S = 1.02

2244 reflections

154 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: SMART (Bruker, 2000 ▶); cell refinement: SAINT (Bruker, 2000 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXL97.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536813006272/rk2395sup1.cif

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813006272/rk2395Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813006272/rk2395Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C14H20N2	F(000) = 472
Mr = 216.32	Dx = 1.128 Mg m−3
Orthorhombic, P212121	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: P 2ac 2ab	Cell parameters from 1347 reflections
a = 9.064 (2) Å	θ = 2.8–20.0°
b = 11.417 (3) Å	µ = 0.07 mm−1
c = 12.311 (3) Å	T = 200 K
V = 1274.0 (5) Å3	Block, colourless
Z = 4	0.30 × 0.25 × 0.20 mm

Bruker SMART CCD diffractometer	2244 independent reflections
Radiation source: fine–focus sealed tube	1758 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.042
φ and ω scan	θmax = 25.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −10→7
Tmin = 0.980, Tmax = 0.987	k = −13→12
7147 measured reflections	l = −14→14

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.040	H atoms treated by a mixture of independent and constrained refinement
wR(F2) = 0.098	w = 1/[σ2(Fo2) + (0.0452P)2 + 0.0788P] where P = (Fo2 + 2Fc2)/3
S = 1.02	(Δ/σ)max < 0.001
2244 reflections	Δρmax = 0.15 e Å−3
154 parameters	Δρmin = −0.12 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.020 (3)

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 > σ(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	0.12298 (18)	0.22773 (14)	0.08238 (13)	0.0434 (4)
N2	−0.08387 (18)	0.17325 (15)	−0.02421 (15)	0.0475 (5)
C1	0.1003 (2)	0.14588 (16)	0.17183 (15)	0.0391 (5)
H1B	−0.0079	0.1422	0.1872	0.047*
C2	0.1528 (2)	0.02235 (17)	0.14538 (16)	0.0502 (6)
H2C	0.0991	−0.0073	0.0810	0.060*
H2D	0.2593	0.0240	0.1277	0.060*
C3	0.1267 (3)	−0.05956 (17)	0.24111 (18)	0.0611 (7)
H3A	0.0195	−0.0656	0.2553	0.073*
H3B	0.1638	−0.1387	0.2228	0.073*
C4	0.2041 (3)	−0.0156 (2)	0.34235 (18)	0.0612 (7)
H4A	0.3122	−0.0170	0.3308	0.073*
H4B	0.1809	−0.0679	0.4042	0.073*
C5	0.1552 (3)	0.10824 (19)	0.36872 (17)	0.0612 (6)
H5A	0.2124	0.1376	0.4316	0.073*
H5B	0.0496	0.1075	0.3894	0.073*
C6	0.1769 (2)	0.19043 (17)	0.27290 (16)	0.0485 (5)
H6A	0.1375	0.2687	0.2916	0.058*
H6B	0.2837	0.1989	0.2581	0.058*
C7	0.0332 (2)	0.23343 (16)	−0.00570 (16)	0.0382 (5)
C8	0.0761 (2)	0.32275 (16)	−0.08846 (16)	0.0387 (5)
C9	0.1108 (2)	0.43699 (16)	−0.05829 (17)	0.0460 (5)
H9A	0.1104	0.4587	0.0162	0.055*
C10	0.1457 (3)	0.51857 (19)	−0.13683 (18)	0.0559 (6)
H10A	0.1683	0.5967	−0.1162	0.067*
C11	0.1480 (3)	0.48753 (19)	−0.24477 (19)	0.0578 (6)
H11A	0.1724	0.5446	−0.2980	0.069*
C12	0.1153 (2)	0.37453 (19)	−0.27700 (17)	0.0520 (6)
C13	0.0782 (2)	0.29362 (17)	−0.19718 (16)	0.0446 (5)
H13A	0.0536	0.2160	−0.2181	0.054*
C14	0.1184 (3)	0.3393 (2)	−0.3945 (2)	0.0864 (9)
H14A	0.0928	0.2562	−0.4010	0.130*
H14B	0.2174	0.3523	−0.4240	0.130*
H14C	0.0469	0.3864	−0.4352	0.130*
H2A	−0.098 (2)	0.1201 (17)	0.0303 (17)	0.054 (6)*
H1A	0.213 (2)	0.2603 (17)	0.0752 (16)	0.052 (6)*

	U11	U22	U33	U12	U13	U23
N1	0.0400 (10)	0.0501 (10)	0.0401 (9)	−0.0084 (9)	−0.0028 (8)	0.0139 (8)
N2	0.0419 (10)	0.0512 (10)	0.0495 (11)	−0.0071 (9)	−0.0050 (8)	0.0109 (9)
C1	0.0377 (10)	0.0413 (11)	0.0384 (11)	−0.0025 (9)	0.0019 (9)	0.0065 (8)
C2	0.0573 (14)	0.0481 (12)	0.0451 (13)	0.0004 (11)	−0.0039 (11)	−0.0022 (10)
C3	0.0705 (17)	0.0405 (11)	0.0721 (16)	−0.0032 (12)	−0.0081 (14)	0.0079 (12)
C4	0.0729 (16)	0.0571 (14)	0.0536 (15)	0.0025 (14)	−0.0025 (13)	0.0189 (11)
C5	0.0785 (16)	0.0640 (15)	0.0410 (13)	0.0052 (13)	−0.0004 (12)	0.0068 (11)
C6	0.0565 (13)	0.0438 (11)	0.0450 (12)	0.0025 (11)	−0.0040 (10)	−0.0009 (10)
C7	0.0364 (10)	0.0379 (11)	0.0402 (12)	0.0025 (9)	0.0009 (9)	0.0016 (9)
C8	0.0342 (10)	0.0392 (11)	0.0427 (12)	0.0062 (9)	−0.0006 (9)	0.0042 (9)
C9	0.0502 (13)	0.0430 (11)	0.0448 (12)	0.0024 (10)	−0.0028 (10)	0.0033 (10)
C10	0.0701 (16)	0.0387 (11)	0.0590 (15)	−0.0026 (11)	−0.0040 (12)	0.0082 (11)
C11	0.0638 (16)	0.0524 (13)	0.0570 (15)	−0.0022 (12)	0.0016 (12)	0.0212 (12)
C12	0.0552 (14)	0.0590 (13)	0.0418 (13)	0.0052 (12)	0.0000 (11)	0.0089 (11)
C13	0.0460 (12)	0.0448 (11)	0.0431 (12)	0.0012 (10)	−0.0011 (9)	0.0006 (10)
C14	0.123 (2)	0.0921 (19)	0.0440 (14)	−0.0059 (19)	0.0068 (16)	0.0102 (14)

N1—C7	1.357 (2)	C5—H5B	0.9900
N1—C1	1.459 (2)	C6—H6A	0.9900
N1—H1A	0.90 (2)	C6—H6B	0.9900
N2—C7	1.284 (2)	C7—C8	1.493 (3)
N2—H2A	0.91 (2)	C8—C13	1.379 (3)
C1—C6	1.513 (3)	C8—C9	1.392 (3)
C1—C2	1.524 (3)	C9—C10	1.379 (3)
C1—H1B	1.0000	C9—H9A	0.9500
C2—C3	1.523 (3)	C10—C11	1.375 (3)
C2—H2C	0.9900	C10—H10A	0.9500
C2—H2D	0.9900	C11—C12	1.382 (3)
C3—C4	1.516 (3)	C11—H11A	0.9500
C3—H3A	0.9900	C12—C13	1.390 (3)
C3—H3B	0.9900	C12—C14	1.502 (3)
C4—C5	1.517 (3)	C13—H13A	0.9500
C4—H4A	0.9900	C14—H14A	0.9800
C4—H4B	0.9900	C14—H14B	0.9800
C5—C6	1.520 (3)	C14—H14C	0.9800
C5—H5A	0.9900
C7—N1—C1	123.32 (16)	C1—C6—C5	111.80 (17)
C7—N1—H1A	116.5 (13)	C1—C6—H6A	109.3
C1—N1—H1A	117.7 (13)	C5—C6—H6A	109.3
C7—N2—H2A	110.1 (13)	C1—C6—H6B	109.3
N1—C1—C6	109.93 (15)	C5—C6—H6B	109.3
N1—C1—C2	112.82 (15)	H6A—C6—H6B	107.9
C6—C1—C2	110.11 (16)	N2—C7—N1	127.70 (18)
N1—C1—H1B	107.9	N2—C7—C8	117.35 (18)
C6—C1—H1B	107.9	N1—C7—C8	114.94 (16)
C2—C1—H1B	107.9	C13—C8—C9	118.79 (18)
C3—C2—C1	110.77 (16)	C13—C8—C7	120.08 (17)
C3—C2—H2C	109.5	C9—C8—C7	121.12 (18)
C1—C2—H2C	109.5	C10—C9—C8	119.8 (2)
C3—C2—H2D	109.5	C10—C9—H9A	120.1
C1—C2—H2D	109.5	C8—C9—H9A	120.1
H2C—C2—H2D	108.1	C11—C10—C9	120.4 (2)
C4—C3—C2	111.18 (18)	C11—C10—H10A	119.8
C4—C3—H3A	109.4	C9—C10—H10A	119.8
C2—C3—H3A	109.4	C10—C11—C12	121.0 (2)
C4—C3—H3B	109.4	C10—C11—H11A	119.5
C2—C3—H3B	109.4	C12—C11—H11A	119.5
H3A—C3—H3B	108.0	C11—C12—C13	118.0 (2)
C3—C4—C5	110.44 (19)	C11—C12—C14	121.5 (2)
C3—C4—H4A	109.6	C13—C12—C14	120.5 (2)
C5—C4—H4A	109.6	C8—C13—C12	121.95 (19)
C3—C4—H4B	109.6	C8—C13—H13A	119.0
C5—C4—H4B	109.6	C12—C13—H13A	119.0
H4A—C4—H4B	108.1	C12—C14—H14A	109.5
C4—C5—C6	111.80 (18)	C12—C14—H14B	109.5
C4—C5—H5A	109.3	H14A—C14—H14B	109.5
C6—C5—H5A	109.3	C12—C14—H14C	109.5
C4—C5—H5B	109.3	H14A—C14—H14C	109.5
C6—C5—H5B	109.3	H14B—C14—H14C	109.5
H5A—C5—H5B	107.9

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···N2i	0.90 (2)	2.08 (2)	2.975 (2)	168.0 (18)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯N2i	0.90 (2)	2.08 (2)	2.975 (2)	168.0 (18)

Symmetry code: (i) .