2-[2,6-Bis(propan-2-yl)phen-yl]-1,3-di-cyclo-hexyl-guanidine.

In the title asymmetric di-cyclo-hexyl-phenyl-guanidine, C25H41N3, the central guanidine C atom deviates by only 0.004 (2) Å from the central plane defined by the three N atoms. The benzene and the cyclo-hexyl rings are rotated out of the central plane of the N3C unit by 85.63 (12)° (benzene) and 51.52 (9) and 49.37 (12)° (cyclohexyl). The crystal packing features only by van der Waals inter-actions.

Related literature

For similar structures of various related compounds, see: Shen et al. (2011 ▶); Ghosh et al. (2008 ▶); Yıldırım et al. (2007 ▶); Brazeau et al. (2012 ▶); Han & Huynh (2009 ▶); Tanatani et al. (1998 ▶); Zhang et al. (2009 ▶); Boere et al. (2000 ▶). For standard bond lengths, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C25H41N3

M = 383.61

Monoclinic,

a = 30.9001 (3) Å

b = 9.9442 (5) Å

c = 18.5260 (3) Å

β = 124.962 (3)°

V = 4665.3 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.06 mm−1

T = 150 K

0.45 × 0.18 × 0.18 mm

Data collection

Bruker–Nonius KappaCCD area-detector diffractometer

Absorption correction: gaussian (Coppens, 1970 ▶) T min = 0.982, T max = 0.991

40512 measured reflections

5336 independent reflections

3272 reflections with I > 2σ(I)

R int = 0.098

Refinement

R[F 2 > 2σ(F 2)] = 0.060

wR(F 2) = 0.137

S = 1.06

5336 reflections

253 parameters

H-atom parameters constrained

Δρmax = 0.41 e Å−3

Δρmin = −0.37 e Å−3

Data collection: COLLECT (Hooft, 1998 ▶) and DENZO (Otwinowski & Minor, 1997 ▶); cell refinement: COLLECT and DENZO; data reduction: COLLECT and DENZO; program(s) used to solve structure: SIR92 (Altomare et al., 1994 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablock(s) I. DOI: 10.1107/S1600536814011611/kp2469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814011611/kp2469Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814011611/kp2469Isup3.cml

CCDC reference: 1004128

Additional supporting information: crystallographic information; 3D view; checkCIF report

C25H41N3	F(000) = 1696
Mr = 383.61	Dx = 1.092 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 40662 reflections
a = 30.9001 (3) Å	θ = 1–27.5°
b = 9.9442 (5) Å	µ = 0.06 mm−1
c = 18.5260 (3) Å	T = 150 K
β = 124.962 (3)°	Needle, colourless
V = 4665.3 (3) Å3	0.45 × 0.18 × 0.18 mm
Z = 8

Bruker–Nonius KappaCCD area-detector diffractometer	5336 independent reflections
Radiation source: fine-focus sealed tube	3272 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.098
Detector resolution: 9.091 pixels mm-1	θmax = 27.5°, θmin = 2.2°
φ and ω scans to fill the Ewald sphere	h = −40→37
Absorption correction: gaussian (Coppens, 1970)	k = −12→12
Tmin = 0.982, Tmax = 0.991	l = −24→24
40512 measured reflections

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)] = 0.060	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.137	H-atom parameters constrained
S = 1.06	w = 1/[σ2(Fo2) + (0.0373P)2 + 6.0132P] where P = (Fo2 + 2Fc2)/3
5336 reflections	(Δ/σ)max < 0.001
253 parameters	Δρmax = 0.41 e Å−3
0 restraints	Δρmin = −0.37 e Å−3

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 > 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	0.85963 (6)	−0.00660 (16)	0.09390 (11)	0.0249 (4)
N2	0.91824 (6)	0.12199 (17)	0.22129 (11)	0.0272 (4)
H2	0.9424	0.1231	0.2117	0.033*
C1	0.87631 (7)	0.03532 (18)	0.17160 (13)	0.0230 (4)
N3	0.85204 (6)	−0.00799 (17)	0.21031 (11)	0.0281 (4)
H3	0.8618	0.0247	0.2605	0.034*
C7	0.86512 (7)	0.1607 (2)	0.00225 (13)	0.0259 (4)
C2	0.88288 (7)	0.0413 (2)	0.05185 (13)	0.0242 (4)
C3	0.92155 (7)	−0.0387 (2)	0.05466 (13)	0.0268 (4)
C4	0.93881 (8)	−0.0019 (2)	0.00274 (14)	0.0335 (5)
H4	0.9635	−0.0554	0.0027	0.040*
C20	0.81023 (8)	−0.10825 (19)	0.16858 (13)	0.0246 (4)
H20	0.7872	−0.0884	0.1054	0.029*
C25	0.77745 (8)	−0.0977 (2)	0.20611 (14)	0.0292 (5)
H25A	0.8000	−0.1130	0.2692	0.035*
H25B	0.7628	−0.0079	0.1960	0.035*
C8	0.94246 (8)	−0.1630 (2)	0.11264 (14)	0.0305 (5)
H8	0.9429	−0.1434	0.1649	0.037*
C19	0.97612 (8)	0.2886 (2)	0.32971 (14)	0.0347 (5)
H19A	0.9757	0.3364	0.2837	0.042*
H19B	1.0052	0.2252	0.3564	0.042*
C15	0.87852 (8)	0.3080 (2)	0.25502 (14)	0.0309 (5)
H15A	0.8737	0.3595	0.2064	0.037*
H15B	0.8465	0.2567	0.2329	0.037*
C11	0.82506 (8)	0.2511 (2)	0.00116 (14)	0.0284 (5)
H11	0.8238	0.2248	0.0509	0.034*
C14	0.92473 (7)	0.2116 (2)	0.28959 (13)	0.0266 (4)
H14	0.9274	0.1562	0.3357	0.032*
C21	0.83129 (9)	−0.2505 (2)	0.17984 (16)	0.0347 (5)
H21A	0.8517	−0.2565	0.1551	0.042*
H21B	0.8545	−0.2718	0.2421	0.042*
C10	0.99868 (9)	−0.2004 (2)	0.14496 (16)	0.0408 (6)
H10A	0.9990	−0.2301	0.0960	0.049*
H10B	1.0112	−0.2714	0.1876	0.049*
H10C	1.0212	−0.1233	0.1716	0.049*
C6	0.88416 (8)	0.1932 (2)	−0.04814 (14)	0.0337 (5)
H6	0.8726	0.2715	−0.0817	0.040*
C5	0.91994 (8)	0.1121 (2)	−0.04892 (14)	0.0368 (5)
H5	0.9314	0.1341	−0.0842	0.044*
C16	0.88758 (9)	0.4038 (2)	0.32643 (15)	0.0374 (5)
H16A	0.8582	0.4660	0.3017	0.045*
H16B	0.8893	0.3532	0.3728	0.045*
C24	0.73288 (8)	−0.2005 (2)	0.16355 (16)	0.0394 (6)
H24A	0.7143	−0.1963	0.1915	0.047*
H24B	0.7080	−0.1777	0.1019	0.047*
C12	0.77015 (9)	0.2305 (3)	−0.08243 (16)	0.0453 (6)
H12A	0.7456	0.2881	−0.0812	0.054*
H12B	0.7597	0.1384	−0.0861	0.054*
H12C	0.7703	0.2521	−0.1328	0.054*
C23	0.75267 (10)	−0.3431 (2)	0.17037 (17)	0.0425 (6)
H23A	0.7228	−0.4035	0.1373	0.051*
H23B	0.7734	−0.3713	0.2315	0.051*
C9	0.90576 (10)	−0.2825 (2)	0.06648 (16)	0.0441 (6)
H9A	0.9059	−0.3079	0.0166	0.053*
H9B	0.8706	−0.2579	0.0470	0.053*
H9C	0.9175	−0.3569	0.1066	0.053*
C13	0.84053 (10)	0.3987 (2)	0.01292 (19)	0.0496 (7)
H13A	0.8382	0.4305	−0.0381	0.059*
H13B	0.8761	0.4088	0.0640	0.059*
H13C	0.8171	0.4499	0.0206	0.059*
C17	0.93828 (9)	0.4821 (2)	0.36433 (16)	0.0429 (6)
H17A	0.9351	0.5393	0.3191	0.052*
H17B	0.9442	0.5394	0.4116	0.052*
C18	0.98491 (9)	0.3882 (3)	0.39960 (15)	0.0427 (6)
H18A	0.9908	0.3394	0.4499	0.051*
H18B	1.0163	0.4410	0.4196	0.051*
C22	0.78632 (10)	−0.3517 (2)	0.13444 (18)	0.0435 (6)
H22A	0.8005	−0.4419	0.1432	0.052*
H22B	0.7645	−0.3338	0.0717	0.052*

	U11	U22	U33	U12	U13	U23
N1	0.0297 (9)	0.0247 (9)	0.0258 (9)	−0.0024 (7)	0.0191 (8)	−0.0014 (7)
N2	0.0262 (9)	0.0324 (9)	0.0287 (9)	−0.0067 (8)	0.0190 (8)	−0.0076 (8)
C1	0.0243 (10)	0.0210 (10)	0.0273 (11)	0.0013 (8)	0.0169 (9)	0.0007 (8)
N3	0.0362 (9)	0.0287 (9)	0.0271 (9)	−0.0093 (8)	0.0225 (8)	−0.0058 (8)
C7	0.0235 (10)	0.0299 (11)	0.0242 (10)	−0.0055 (9)	0.0136 (9)	−0.0031 (9)
C2	0.0236 (10)	0.0288 (10)	0.0224 (10)	−0.0069 (8)	0.0145 (8)	−0.0039 (8)
C3	0.0268 (10)	0.0314 (11)	0.0235 (11)	−0.0056 (9)	0.0152 (9)	−0.0063 (9)
C4	0.0311 (11)	0.0449 (13)	0.0316 (12)	−0.0006 (10)	0.0222 (10)	−0.0034 (10)
C20	0.0301 (10)	0.0234 (10)	0.0252 (10)	−0.0020 (9)	0.0188 (9)	0.0010 (8)
C25	0.0328 (11)	0.0293 (11)	0.0335 (12)	0.0028 (9)	0.0238 (10)	0.0015 (9)
C8	0.0369 (12)	0.0305 (11)	0.0309 (12)	0.0002 (9)	0.0234 (10)	−0.0032 (9)
C19	0.0282 (11)	0.0446 (13)	0.0317 (12)	−0.0083 (10)	0.0175 (10)	−0.0073 (10)
C15	0.0283 (11)	0.0333 (12)	0.0286 (12)	−0.0046 (9)	0.0148 (9)	−0.0051 (9)
C11	0.0334 (11)	0.0262 (10)	0.0280 (11)	−0.0024 (9)	0.0190 (10)	0.0007 (9)
C14	0.0281 (11)	0.0310 (11)	0.0225 (10)	−0.0043 (9)	0.0155 (9)	−0.0029 (9)
C21	0.0452 (13)	0.0269 (11)	0.0485 (14)	−0.0009 (10)	0.0366 (12)	−0.0002 (10)
C10	0.0408 (13)	0.0436 (14)	0.0407 (14)	0.0086 (11)	0.0248 (11)	0.0031 (11)
C6	0.0318 (11)	0.0399 (12)	0.0285 (12)	−0.0044 (10)	0.0168 (10)	0.0046 (10)
C5	0.0343 (12)	0.0545 (14)	0.0312 (12)	−0.0054 (11)	0.0244 (10)	0.0010 (11)
C16	0.0398 (12)	0.0374 (12)	0.0375 (13)	−0.0019 (10)	0.0237 (11)	−0.0060 (10)
C24	0.0296 (11)	0.0474 (14)	0.0449 (14)	−0.0018 (11)	0.0236 (11)	0.0057 (11)
C12	0.0345 (13)	0.0515 (15)	0.0456 (15)	0.0038 (11)	0.0205 (12)	−0.0053 (12)
C23	0.0496 (14)	0.0355 (12)	0.0530 (15)	−0.0130 (11)	0.0357 (13)	−0.0007 (11)
C9	0.0550 (15)	0.0369 (13)	0.0448 (15)	−0.0077 (12)	0.0313 (13)	−0.0082 (11)
C13	0.0585 (16)	0.0332 (13)	0.0658 (18)	−0.0030 (12)	0.0408 (15)	−0.0041 (12)
C17	0.0500 (14)	0.0388 (13)	0.0402 (14)	−0.0123 (12)	0.0260 (12)	−0.0155 (11)
C18	0.0353 (12)	0.0523 (15)	0.0336 (13)	−0.0167 (11)	0.0156 (11)	−0.0158 (11)
C22	0.0659 (16)	0.0254 (11)	0.0565 (16)	−0.0099 (11)	0.0451 (14)	−0.0074 (11)

N1—C1	1.289 (2)	C14—H14	0.9798
N1—C2	1.411 (2)	C21—C22	1.521 (3)
N2—C1	1.379 (2)	C21—H21A	0.9702
N2—C14	1.465 (2)	C21—H21B	0.9699
N2—H2	0.8602	C10—H10A	0.9599
C1—N3	1.370 (2)	C10—H10B	0.9600
N3—C20	1.455 (2)	C10—H10C	0.9601
N3—H3	0.8599	C6—C5	1.375 (3)
C7—C6	1.397 (3)	C6—H6	0.9299
C7—C2	1.406 (3)	C5—H5	0.9301
C7—C11	1.521 (3)	C16—C17	1.515 (3)
C2—C3	1.412 (3)	C16—H16A	0.9700
C3—C4	1.390 (3)	C16—H16B	0.9701
C3—C8	1.518 (3)	C24—C23	1.520 (3)
C4—C5	1.380 (3)	C24—H24A	0.9698
C4—H4	0.9299	C24—H24B	0.9699
C20—C21	1.521 (3)	C12—H12A	0.9598
C20—C25	1.526 (3)	C12—H12B	0.9601
C20—H20	0.9799	C12—H12C	0.9601
C25—C24	1.523 (3)	C23—C22	1.525 (3)
C25—H25A	0.9700	C23—H23A	0.9701
C25—H25B	0.9701	C23—H23B	0.9700
C8—C9	1.522 (3)	C9—H9A	0.9597
C8—C10	1.524 (3)	C9—H9B	0.9602
C8—H8	0.9798	C9—H9C	0.9601
C19—C14	1.519 (3)	C13—H13A	0.9600
C19—C18	1.526 (3)	C13—H13B	0.9601
C19—H19A	0.9700	C13—H13C	0.9600
C19—H19B	0.9699	C17—C18	1.515 (3)
C15—C16	1.521 (3)	C17—H17A	0.9699
C15—C14	1.523 (3)	C17—H17B	0.9701
C15—H15A	0.9700	C18—H18A	0.9700
C15—H15B	0.9700	C18—H18B	0.9702
C11—C12	1.519 (3)	C22—H22A	0.9700
C11—C13	1.520 (3)	C22—H22B	0.9700
C11—H11	0.9801
C1—N1—C2	120.19 (16)	C20—C21—H21B	109.4
C1—N2—C14	124.63 (16)	H21A—C21—H21B	108.1
C1—N2—H2	117.7	C8—C10—H10A	109.3
C14—N2—H2	117.7	C8—C10—H10B	109.5
N1—C1—N3	119.62 (17)	H10A—C10—H10B	109.5
N1—C1—N2	124.68 (17)	C8—C10—H10C	109.6
N3—C1—N2	115.69 (17)	H10A—C10—H10C	109.5
C1—N3—C20	121.52 (16)	H10B—C10—H10C	109.5
C1—N3—H3	119.3	C5—C6—C7	121.4 (2)
C20—N3—H3	119.2	C5—C6—H6	119.2
C6—C7—C2	118.41 (18)	C7—C6—H6	119.4
C6—C7—C11	120.38 (19)	C6—C5—C4	119.83 (19)
C2—C7—C11	121.19 (17)	C6—C5—H5	120.1
C7—C2—N1	120.96 (17)	C4—C5—H5	120.0
C7—C2—C3	120.35 (17)	C17—C16—C15	110.58 (18)
N1—C2—C3	118.49 (17)	C17—C16—H16A	109.3
C4—C3—C2	118.59 (19)	C15—C16—H16A	109.4
C4—C3—C8	121.83 (18)	C17—C16—H16B	109.8
C2—C3—C8	119.57 (17)	C15—C16—H16B	109.6
C5—C4—C3	121.3 (2)	H16A—C16—H16B	108.1
C5—C4—H4	119.3	C23—C24—C25	112.42 (18)
C3—C4—H4	119.4	C23—C24—H24A	109.2
N3—C20—C21	112.63 (16)	C25—C24—H24A	109.3
N3—C20—C25	109.28 (16)	C23—C24—H24B	109.0
C21—C20—C25	110.17 (16)	C25—C24—H24B	108.9
N3—C20—H20	108.2	H24A—C24—H24B	107.9
C21—C20—H20	108.2	C11—C12—H12A	109.3
C25—C20—H20	108.2	C11—C12—H12B	109.5
C24—C25—C20	110.97 (17)	H12A—C12—H12B	109.5
C24—C25—H25A	109.3	C11—C12—H12C	109.6
C20—C25—H25A	109.4	H12A—C12—H12C	109.5
C24—C25—H25B	109.5	H12B—C12—H12C	109.5
C20—C25—H25B	109.5	C24—C23—C22	111.05 (18)
H25A—C25—H25B	108.1	C24—C23—H23A	109.5
C3—C8—C9	111.11 (18)	C22—C23—H23A	109.2
C3—C8—C10	113.82 (17)	C24—C23—H23B	109.4
C9—C8—C10	110.19 (18)	C22—C23—H23B	109.6
C3—C8—H8	107.2	H23A—C23—H23B	108.1
C9—C8—H8	107.1	C8—C9—H9A	109.5
C10—C8—H8	107.1	C8—C9—H9B	109.3
C14—C19—C18	111.73 (17)	H9A—C9—H9B	109.5
C14—C19—H19A	109.5	C8—C9—H9C	109.6
C18—C19—H19A	109.5	H9A—C9—H9C	109.5
C14—C19—H19B	109.0	H9B—C9—H9C	109.4
C18—C19—H19B	109.1	C11—C13—H13A	109.7
H19A—C19—H19B	107.9	C11—C13—H13B	109.3
C16—C15—C14	111.56 (17)	H13A—C13—H13B	109.5
C16—C15—H15A	109.3	C11—C13—H13C	109.4
C14—C15—H15A	109.3	H13A—C13—H13C	109.5
C16—C15—H15B	109.4	H13B—C13—H13C	109.5
C14—C15—H15B	109.3	C16—C17—C18	111.0 (2)
H15A—C15—H15B	107.9	C16—C17—H17A	109.6
C12—C11—C13	110.6 (2)	C18—C17—H17A	109.5
C12—C11—C7	111.03 (17)	C16—C17—H17B	109.3
C13—C11—C7	112.47 (17)	C18—C17—H17B	109.4
C12—C11—H11	107.5	H17A—C17—H17B	108.0
C13—C11—H11	107.6	C17—C18—C19	111.79 (19)
C7—C11—H11	107.4	C17—C18—H18A	109.4
N2—C14—C19	108.47 (16)	C19—C18—H18A	109.5
N2—C14—C15	112.84 (16)	C17—C18—H18B	109.0
C19—C14—C15	110.73 (17)	C19—C18—H18B	109.1
N2—C14—H14	108.2	H18A—C18—H18B	107.9
C19—C14—H14	108.3	C21—C22—C23	110.91 (19)
C15—C14—H14	108.1	C21—C22—H22A	109.7
C22—C21—C20	110.87 (18)	C23—C22—H22A	109.6
C22—C21—H21A	109.4	C21—C22—H22B	109.2
C20—C21—H21A	109.6	C23—C22—H22B	109.4
C22—C21—H21B	109.4	H22A—C22—H22B	108.0