1-(1-Adamantylmeth­yl)-1H-benzimidazole

Černochová, J.; Nečas, M.; Kuřitka, I.; Vícha, R.

doi:10.1107/S1600536811041018

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 67| Part 11| November 2011| Page o2906

doi:10.1107/S1600536811041018

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1-(1-Adamantylmethyl)-1H-benzimidazole

Jarmila Černochová,^a Marek Nečas,^b Ivo Kuřitka ^c and Robert Vícha ^a ^*

^aDepartment of Chemistry, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, ^bDepartment of Chemistry, Faculty of Science, Masaryk University, Kamenice 5, Brno-Bohunice, 625 00, Czech Republic, and ^cPolymer Centre, Faculty of Technology, Tomas Bata University in Zlin, Nám. T. G. Masaryka 275, Zlín,762 72, Czech Republic, and, Centre of Polymer Systems, University Institute, Tomas Bata University in Zlin, Nad Ovčírnou 3685, Zlín, 760 01, Czech Republic
^*Correspondence e-mail: rvicha@ft.utb.cz

(Received 26 September 2011; accepted 5 October 2011; online 12 October 2011)

The asymmetric unit of the title compound, C₁₈H₂₂N₂, contains two independent molecules which differ slightly with respect to the torsion angles involving the atoms joining the adamantyl and benzimidazole groups. The bond angles in the adamantane cage vary within the range 108.27 (9)–110.55 (10)°. The benzimidazole ring system in both molecules is essentially planar, the maximum deviations from the best planes being 0.0134 (15) and 0.0229 (14) Å. In the crystal, weak C—H⋯π interactions link the molecules.

Related literature

For the synthesis, spectroscopic characterization and biological activity of the title compound, see: Hille et al. (2011 ). For background to C(sp²)—H⋯π interactions, see: Takahashi et al. (2010 ). For two polymorphs of a related structure, see: Lei & Zhou (2009 ); Zhang et al. (2010 ).

Experimental

Crystal data

C₁₈H₂₂N₂
M_r = 266.38
Monoclinic, P 2₁ /n
a = 22.0249 (9) Å
b = 6.4628 (1) Å
c = 22.2739 (8) Å
β = 118.694 (5)°
V = 2781.2 (2) Å³
Z = 8
Mo Kα radiation
μ = 0.08 mm⁻¹
T = 120 K
0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, USA.]$ ) T_min = 0.928, T_max = 1.000
32353 measured reflections
4899 independent reflections
3314 reflections with I > 2σ(I)
R_int = 0.034

Refinement

R[F² > 2σ(F²)] = 0.030
wR(F²) = 0.064
S = 0.83
4899 reflections
361 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg1 is the centroid of the C2–C7 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1ⁱ	0.95	3.07	3.9197 (16)	150
Symmetry code: (i) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, USA.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, USA.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811041018/lh5341sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811041018/lh5341Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811041018/lh5341Isup3.cml

checkCIF report

Comment top

Title compound has been prepared as a suitable building block for benzimidazolium-based carbene ligands synthesis and recently, the biological activity related to treatment of cortisole-dependent diseases has been studied (Hille et al., 2011). Two polymorphs of a related structure have already been published (Lei & Zhou, 2009; Zhang et al., 2010).

Both crystallographically independent molecules in the asymmetric unit (Fig. 1) contain essentially planar 1H-benzo[d]imidazole heterocycle with a maximum deviations from the best plane being 0.0134 (15) Å for C2 and 0.0229 (14) Å for C21, respectively. The torsion angles C7—N1—C8—C9 and N1—C8—C9—C16 describing the mutual orientation of benzimidazole and adamantane groups are 95.31 (15)° and -179.38 (10)°, respectively. The corresponding angles in the other molecule are -92.89 (15)° and -177.52 (10)°, respectively. The crystal packing is stabilized via weak C—H···π interactions (Fig. 2, Table 1).

Related literature top

For the synthesis, spectroscopic characterization and biological activity of the title compound, see: Hille et al. (2011). For background to C(sp²)—H···π interactions, see: Takahashi et al. (2010). For two polymorphs of a related structure, see: Lei & Zhou (2009); Zhang et al. (2010).

Experimental top

Benzimidazole (0.40 g, 3.39 mmol) was dissolved in 40 cm³ of dry DMF and sodium hydride (0.2 g, 8.46 mmol) was added portionwise at room temperature. Into this mixture, 1-adamantylbromomethane (1.16 g, 5.09 mmol) was added and the mixture was stirred under argon for 5 days at 373 K. The reaction mixture was poured onto 100 g of crushed ice, extracted with 4 × 25 cm³ of dichloromethane and the collected organic portions were washed several times with distilled water, brine and dried over Na₂SO₄. The solvent was distilled off under reduced pressure and residual DMF was removed via azeotropic distillation with trichloromethane. The crude material was purified by crystallization (petroleum ether:ethyl acetate, 1:1, v:v) to yield 850 mg (94%) of colorless powder with mp=483–488 K. The crystal used for data collection was grown by spontaneous evaporation of a trichloromethane:methanol solution of the title compound at room temperature.

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The asymmetric unit with 50% probability ellipsoids for non hydrogen atoms. H-atoms are shown as spheres at arbitrary radii.
	Fig. 2. Two pairs of molecules linked via weak C—H···π interactions (dotted lines) are colored by symmetry equivalence. H-atoms are omitted except for those participating in H-bonds. Cg1 is centre of gravity of C2–C7, Symmetry codes: (i) x + 1/2, -y + 1/2, z + 1/2; (ii) x - 1/2, -y + 1/2, y - 1/2.

1-(1-Adamantylmethyl)-1H-benzimidazole top

Crystal data top

C₁₈H₂₂N₂	F(000) = 1152
M_r = 266.38	D_x = 1.272 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 486 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 22.0249 (9) Å	Cell parameters from 9351 reflections
b = 6.4628 (1) Å	θ = 2.8–27.3°
c = 22.2739 (8) Å	µ = 0.08 mm⁻¹
β = 118.694 (5)°	T = 120 K
V = 2781.2 (2) Å³	Block, colourless
Z = 8	0.30 × 0.20 × 0.20 mm

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	4899 independent reflections
Radiation source: fine-focus sealed tube	3314 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.034
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.2°
ω scans	h = −26→17
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −7→7
T_min = 0.928, T_max = 1.000	l = −26→26
32353 measured reflections

Refinement top

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.064	H-atom parameters constrained
S = 0.83	w = 1/[σ²(F_o²) + (0.0354P)²] where P = (F_o² + 2F_c²)/3
4899 reflections	(Δ/σ)_max < 0.001
361 parameters	Δρ_max = 0.15 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₈H₂₂N₂	V = 2781.2 (2) Å³
M_r = 266.38	Z = 8
Monoclinic, P2₁/n	Mo Kα radiation
a = 22.0249 (9) Å	µ = 0.08 mm⁻¹
b = 6.4628 (1) Å	T = 120 K
c = 22.2739 (8) Å	0.30 × 0.20 × 0.20 mm
β = 118.694 (5)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	4899 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3314 reflections with I > 2σ(I)
T_min = 0.928, T_max = 1.000	R_int = 0.034
32353 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.030	0 restraints
wR(F²) = 0.064	H-atom parameters constrained
S = 0.83	Δρ_max = 0.15 e Å⁻³
4899 reflections	Δρ_min = −0.16 e Å⁻³
361 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'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 > 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

	x	y	z	U_iso*/U_eq
N1	0.58857 (5)	0.07364 (14)	0.28113 (5)	0.0206 (2)
N2	0.55730 (5)	0.39787 (15)	0.24104 (5)	0.0258 (3)
C1	0.58788 (6)	0.27873 (18)	0.29503 (6)	0.0238 (3)
H1	0.6080	0.3312	0.3404	0.029*
C2	0.53553 (6)	0.26067 (18)	0.18631 (6)	0.0212 (3)
C3	0.49849 (6)	0.2979 (2)	0.11594 (6)	0.0272 (3)
H3	0.4847	0.4340	0.0986	0.033*
C4	0.48257 (7)	0.1313 (2)	0.07262 (6)	0.0297 (3)
H4	0.4574	0.1531	0.0246	0.036*
C5	0.50261 (6)	−0.0698 (2)	0.09772 (6)	0.0290 (3)
H5	0.4909	−0.1811	0.0662	0.035*
C6	0.53897 (6)	−0.11098 (19)	0.16698 (6)	0.0249 (3)
H6	0.5526	−0.2474	0.1840	0.030*
C7	0.55451 (6)	0.05820 (18)	0.21038 (6)	0.0201 (3)
C8	0.62286 (6)	−0.09207 (18)	0.33114 (6)	0.0221 (3)
H8A	0.6009	−0.2255	0.3100	0.026*
H8B	0.6150	−0.0687	0.3708	0.026*
C9	0.70077 (6)	−0.10925 (17)	0.35702 (5)	0.0170 (3)
C10	0.73908 (6)	0.08829 (17)	0.39375 (6)	0.0204 (3)
H10A	0.7223	0.2061	0.3614	0.025*
H10B	0.7293	0.1191	0.4318	0.025*
C11	0.81690 (6)	0.06242 (18)	0.42177 (6)	0.0227 (3)
H11	0.8412	0.1921	0.4458	0.027*
C12	0.83131 (7)	0.01928 (18)	0.36233 (6)	0.0248 (3)
H12A	0.8817	0.0039	0.3798	0.030*
H12B	0.8148	0.1368	0.3298	0.030*
C13	0.79412 (6)	−0.17918 (18)	0.32558 (6)	0.0222 (3)
H13	0.8035	−0.2068	0.2866	0.027*
C14	0.82057 (7)	−0.36073 (18)	0.37585 (6)	0.0255 (3)
H14A	0.8709	−0.3786	0.3934	0.031*
H14B	0.7970	−0.4899	0.3522	0.031*
C15	0.80601 (7)	−0.31763 (18)	0.43533 (6)	0.0239 (3)
H15	0.8231	−0.4360	0.4683	0.029*
C16	0.72824 (7)	−0.29034 (18)	0.40795 (6)	0.0229 (3)
H16A	0.7189	−0.2635	0.4465	0.027*
H16B	0.7039	−0.4192	0.3849	0.027*
C17	0.71637 (6)	−0.15487 (18)	0.29825 (6)	0.0210 (3)
H17A	0.6924	−0.2835	0.2746	0.025*
H17B	0.6988	−0.0403	0.2647	0.025*
C18	0.84322 (7)	−0.11922 (18)	0.47179 (6)	0.0276 (3)
H18A	0.8347	−0.0918	0.5108	0.033*
H18B	0.8937	−0.1356	0.4899	0.033*
N21	0.81236 (5)	0.11037 (14)	0.61146 (5)	0.0206 (2)
N22	0.77666 (6)	0.43222 (15)	0.57082 (5)	0.0266 (3)
C21	0.82934 (7)	0.31252 (19)	0.60867 (6)	0.0247 (3)
H21	0.8756	0.3621	0.6323	0.030*
C22	0.71997 (7)	0.29919 (18)	0.54557 (6)	0.0221 (3)
C23	0.65052 (7)	0.3378 (2)	0.50043 (6)	0.0276 (3)
H23	0.6351	0.4728	0.4828	0.033*
C24	0.60493 (7)	0.1751 (2)	0.48206 (6)	0.0297 (3)
H24	0.5572	0.1988	0.4516	0.036*
C25	0.62717 (7)	−0.0254 (2)	0.50718 (6)	0.0279 (3)
H25	0.5942	−0.1344	0.4931	0.033*
C26	0.69569 (7)	−0.06793 (19)	0.55175 (6)	0.0231 (3)
H26	0.7109	−0.2035	0.5689	0.028*
C27	0.74142 (7)	0.09792 (18)	0.57037 (6)	0.0202 (3)
C28	0.86030 (6)	−0.05658 (18)	0.65027 (6)	0.0211 (3)
H28A	0.9047	−0.0329	0.6503	0.025*
H28B	0.8411	−0.1891	0.6264	0.025*
C29	0.87474 (6)	−0.07727 (17)	0.72453 (6)	0.0170 (3)
C30	0.90524 (6)	0.12265 (17)	0.76505 (6)	0.0196 (3)
H30A	0.9475	0.1611	0.7625	0.023*
H30B	0.8713	0.2365	0.7447	0.023*
C31	0.92319 (6)	0.09273 (18)	0.83991 (6)	0.0214 (3)
H31	0.9433	0.2237	0.8658	0.026*
C32	0.97601 (6)	−0.08287 (18)	0.87178 (6)	0.0252 (3)
H32A	1.0189	−0.0479	0.8700	0.030*
H32B	0.9879	−0.1014	0.9203	0.030*
C33	0.94509 (7)	−0.28301 (18)	0.83216 (6)	0.0227 (3)
H33	0.9794	−0.3980	0.8528	0.027*
C34	0.87901 (7)	−0.33678 (18)	0.83533 (6)	0.0254 (3)
H34A	0.8592	−0.4672	0.8102	0.031*
H34B	0.8900	−0.3571	0.8835	0.031*
C35	0.82659 (6)	−0.16154 (18)	0.80349 (6)	0.0223 (3)
H35	0.7834	−0.1967	0.8056	0.027*
C36	0.80937 (6)	−0.13371 (18)	0.72869 (6)	0.0208 (3)
H36A	0.7895	−0.2636	0.7032	0.025*
H36B	0.7744	−0.0228	0.7074	0.025*
C37	0.92803 (6)	−0.25205 (17)	0.75754 (6)	0.0210 (3)
H37A	0.9092	−0.3821	0.7317	0.025*
H37B	0.9708	−0.2171	0.7556	0.025*
C38	0.85747 (7)	0.03925 (18)	0.84316 (6)	0.0239 (3)
H38A	0.8235	0.1531	0.8230	0.029*
H38B	0.8683	0.0217	0.8915	0.029*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0174 (6)	0.0193 (6)	0.0220 (5)	0.0012 (5)	0.0070 (5)	0.0012 (4)
N2	0.0240 (7)	0.0219 (6)	0.0326 (6)	0.0042 (5)	0.0145 (5)	0.0022 (5)
C1	0.0203 (8)	0.0231 (7)	0.0282 (7)	0.0005 (6)	0.0118 (6)	−0.0036 (6)
C2	0.0135 (8)	0.0227 (7)	0.0282 (7)	0.0014 (6)	0.0104 (6)	0.0035 (5)
C3	0.0192 (8)	0.0300 (7)	0.0336 (7)	0.0041 (6)	0.0136 (6)	0.0109 (6)
C4	0.0196 (8)	0.0416 (9)	0.0237 (7)	−0.0017 (7)	0.0070 (6)	0.0063 (6)
C5	0.0239 (9)	0.0330 (8)	0.0249 (7)	−0.0076 (7)	0.0077 (6)	−0.0033 (6)
C6	0.0218 (8)	0.0231 (7)	0.0263 (7)	−0.0038 (6)	0.0087 (6)	0.0005 (6)
C7	0.0124 (8)	0.0242 (7)	0.0221 (7)	−0.0016 (6)	0.0071 (6)	0.0025 (5)
C8	0.0247 (8)	0.0200 (7)	0.0218 (7)	−0.0003 (6)	0.0113 (6)	0.0023 (5)
C9	0.0177 (8)	0.0164 (6)	0.0163 (6)	0.0014 (5)	0.0076 (6)	0.0010 (5)
C10	0.0235 (8)	0.0178 (6)	0.0190 (6)	0.0025 (6)	0.0094 (6)	−0.0011 (5)
C11	0.0193 (8)	0.0190 (7)	0.0244 (7)	−0.0009 (6)	0.0063 (6)	−0.0052 (5)
C12	0.0216 (8)	0.0223 (7)	0.0315 (7)	0.0026 (6)	0.0134 (7)	0.0043 (6)
C13	0.0258 (9)	0.0226 (7)	0.0232 (6)	0.0017 (6)	0.0156 (6)	−0.0014 (5)
C14	0.0254 (8)	0.0194 (7)	0.0329 (7)	0.0030 (6)	0.0149 (7)	−0.0008 (6)
C15	0.0253 (9)	0.0221 (7)	0.0221 (7)	0.0077 (6)	0.0097 (6)	0.0075 (5)
C16	0.0303 (9)	0.0203 (7)	0.0207 (6)	0.0020 (6)	0.0143 (6)	0.0025 (5)
C17	0.0262 (8)	0.0186 (6)	0.0171 (6)	−0.0011 (6)	0.0095 (6)	−0.0013 (5)
C18	0.0235 (8)	0.0330 (8)	0.0199 (7)	0.0052 (6)	0.0053 (6)	−0.0007 (6)
N21	0.0234 (7)	0.0184 (6)	0.0190 (5)	0.0037 (5)	0.0094 (5)	0.0028 (4)
N22	0.0324 (7)	0.0223 (6)	0.0233 (6)	0.0043 (6)	0.0119 (5)	0.0039 (5)
C21	0.0309 (9)	0.0223 (7)	0.0222 (7)	−0.0010 (6)	0.0138 (6)	0.0012 (6)
C22	0.0292 (9)	0.0221 (7)	0.0160 (6)	0.0058 (6)	0.0116 (6)	0.0011 (5)
C23	0.0354 (9)	0.0260 (7)	0.0185 (7)	0.0111 (7)	0.0108 (7)	0.0020 (6)
C24	0.0256 (9)	0.0367 (8)	0.0196 (7)	0.0097 (7)	0.0051 (6)	−0.0019 (6)
C25	0.0279 (9)	0.0321 (8)	0.0200 (7)	−0.0007 (7)	0.0085 (7)	−0.0054 (6)
C26	0.0280 (9)	0.0216 (7)	0.0176 (6)	0.0041 (6)	0.0093 (6)	−0.0005 (5)
C27	0.0224 (8)	0.0246 (7)	0.0131 (6)	0.0036 (6)	0.0083 (6)	−0.0016 (5)
C28	0.0205 (8)	0.0196 (6)	0.0229 (7)	0.0045 (6)	0.0102 (6)	0.0017 (5)
C29	0.0155 (7)	0.0163 (6)	0.0196 (6)	0.0009 (5)	0.0087 (6)	0.0015 (5)
C30	0.0160 (8)	0.0179 (6)	0.0258 (7)	0.0003 (5)	0.0108 (6)	0.0018 (5)
C31	0.0214 (8)	0.0181 (6)	0.0210 (6)	−0.0016 (6)	0.0074 (6)	−0.0019 (5)
C32	0.0221 (8)	0.0274 (7)	0.0221 (7)	0.0012 (6)	0.0073 (6)	0.0026 (6)
C33	0.0224 (8)	0.0193 (6)	0.0230 (7)	0.0060 (6)	0.0084 (6)	0.0053 (5)
C34	0.0348 (9)	0.0197 (7)	0.0235 (7)	−0.0012 (6)	0.0154 (6)	0.0027 (5)
C35	0.0206 (8)	0.0233 (7)	0.0264 (7)	−0.0019 (6)	0.0140 (6)	0.0014 (5)
C36	0.0183 (8)	0.0193 (6)	0.0238 (6)	−0.0002 (6)	0.0094 (6)	−0.0006 (5)
C37	0.0199 (8)	0.0184 (6)	0.0256 (7)	0.0014 (6)	0.0117 (6)	0.0003 (5)
C38	0.0284 (9)	0.0237 (7)	0.0220 (7)	0.0033 (6)	0.0141 (6)	0.0019 (5)

Geometric parameters (Å, º) top

N1—C1	1.3629 (14)	N21—C21	1.3685 (14)
N1—C7	1.3860 (14)	N21—C27	1.3829 (15)
N1—C8	1.4664 (13)	N21—C28	1.4661 (14)
N2—C1	1.3096 (14)	N22—C21	1.3100 (15)
N2—C2	1.3931 (15)	N22—C22	1.3929 (15)
C1—H1	0.9500	C21—H21	0.9500
C2—C3	1.3972 (16)	C22—C23	1.3915 (17)
C2—C7	1.3997 (16)	C22—C27	1.4035 (16)
C3—C4	1.3744 (17)	C23—C24	1.3738 (18)
C3—H3	0.9500	C23—H23	0.9500
C4—C5	1.4000 (17)	C24—C25	1.4029 (17)
C4—H4	0.9500	C24—H24	0.9500
C5—C6	1.3805 (16)	C25—C26	1.3784 (17)
C5—H5	0.9500	C25—H25	0.9500
C6—C7	1.3889 (16)	C26—C27	1.3908 (16)
C6—H6	0.9500	C26—H26	0.9500
C8—C9	1.5294 (16)	C28—C29	1.5329 (15)
C8—H8A	0.9900	C28—H28A	0.9900
C8—H8B	0.9900	C28—H28B	0.9900
C9—C10	1.5324 (15)	C29—C36	1.5306 (16)
C9—C17	1.5331 (15)	C29—C30	1.5340 (15)
C9—C16	1.5374 (15)	C29—C37	1.5380 (15)
C10—C11	1.5257 (16)	C30—C31	1.5299 (15)
C10—H10A	0.9900	C30—H30A	0.9900
C10—H10B	0.9900	C30—H30B	0.9900
C11—C12	1.5280 (16)	C31—C38	1.5234 (17)
C11—C18	1.5281 (16)	C31—C32	1.5337 (15)
C11—H11	1.0000	C31—H31	1.0000
C12—C13	1.5304 (16)	C32—C33	1.5292 (16)
C12—H12A	0.9900	C32—H32A	0.9900
C12—H12B	0.9900	C32—H32B	0.9900
C13—C17	1.5253 (16)	C33—C34	1.5305 (17)
C13—C14	1.5308 (16)	C33—C37	1.5310 (15)
C13—H13	1.0000	C33—H33	1.0000
C14—C15	1.5308 (16)	C34—C35	1.5273 (16)
C14—H14A	0.9900	C34—H34A	0.9900
C14—H14B	0.9900	C34—H34B	0.9900
C15—C16	1.5277 (16)	C35—C36	1.5314 (16)
C15—C18	1.5285 (16)	C35—C38	1.5331 (16)
C15—H15	1.0000	C35—H35	1.0000
C16—H16A	0.9900	C36—H36A	0.9900
C16—H16B	0.9900	C36—H36B	0.9900
C17—H17A	0.9900	C37—H37A	0.9900
C17—H17B	0.9900	C37—H37B	0.9900
C18—H18A	0.9900	C38—H38A	0.9900
C18—H18B	0.9900	C38—H38B	0.9900

C1—N1—C7	105.63 (10)	C21—N21—C27	105.78 (10)
C1—N1—C8	126.55 (10)	C21—N21—C28	126.46 (11)
C7—N1—C8	127.68 (10)	C27—N21—C28	127.76 (10)
C1—N2—C2	103.80 (10)	C21—N22—C22	103.92 (10)
N2—C1—N1	114.83 (11)	N22—C21—N21	114.59 (12)
N2—C1—H1	122.6	N22—C21—H21	122.7
N1—C1—H1	122.6	N21—C21—H21	122.7
N2—C2—C3	129.95 (11)	C23—C22—N22	129.96 (11)
N2—C2—C7	110.23 (10)	C23—C22—C27	119.75 (12)
C3—C2—C7	119.79 (11)	N22—C22—C27	110.24 (11)
C4—C3—C2	117.86 (12)	C24—C23—C22	118.07 (12)
C4—C3—H3	121.1	C24—C23—H23	121.0
C2—C3—H3	121.1	C22—C23—H23	121.0
C3—C4—C5	121.46 (12)	C23—C24—C25	121.53 (12)
C3—C4—H4	119.3	C23—C24—H24	119.2
C5—C4—H4	119.3	C25—C24—H24	119.2
C6—C5—C4	121.84 (12)	C26—C25—C24	121.56 (13)
C6—C5—H5	119.1	C26—C25—H25	119.2
C4—C5—H5	119.1	C24—C25—H25	119.2
C5—C6—C7	116.30 (12)	C25—C26—C27	116.53 (12)
C5—C6—H6	121.9	C25—C26—H26	121.7
C7—C6—H6	121.9	C27—C26—H26	121.7
N1—C7—C6	131.75 (11)	N21—C27—C26	131.96 (11)
N1—C7—C2	105.50 (10)	N21—C27—C22	105.45 (11)
C6—C7—C2	122.74 (11)	C26—C27—C22	122.55 (12)
N1—C8—C9	114.51 (9)	N21—C28—C29	114.71 (9)
N1—C8—H8A	108.6	N21—C28—H28A	108.6
C9—C8—H8A	108.6	C29—C28—H28A	108.6
N1—C8—H8B	108.6	N21—C28—H28B	108.6
C9—C8—H8B	108.6	C29—C28—H28B	108.6
H8A—C8—H8B	107.6	H28A—C28—H28B	107.6
C8—C9—C10	111.79 (9)	C36—C29—C28	111.85 (9)
C8—C9—C17	111.28 (9)	C36—C29—C30	108.90 (9)
C10—C9—C17	108.93 (9)	C28—C29—C30	111.52 (9)
C8—C9—C16	107.83 (9)	C36—C29—C37	108.67 (9)
C10—C9—C16	108.64 (9)	C28—C29—C37	107.17 (9)
C17—C9—C16	108.27 (9)	C30—C29—C37	108.62 (9)
C11—C10—C9	110.46 (9)	C31—C30—C29	110.23 (9)
C11—C10—H10A	109.6	C31—C30—H30A	109.6
C9—C10—H10A	109.6	C29—C30—H30A	109.6
C11—C10—H10B	109.6	C31—C30—H30B	109.6
C9—C10—H10B	109.6	C29—C30—H30B	109.6
H10A—C10—H10B	108.1	H30A—C30—H30B	108.1
C10—C11—C12	108.99 (10)	C38—C31—C30	109.04 (9)
C10—C11—C18	109.93 (10)	C38—C31—C32	109.70 (10)
C12—C11—C18	109.12 (10)	C30—C31—C32	109.85 (10)
C10—C11—H11	109.6	C38—C31—H31	109.4
C12—C11—H11	109.6	C30—C31—H31	109.4
C18—C11—H11	109.6	C32—C31—H31	109.4
C11—C12—C13	109.63 (10)	C33—C32—C31	109.28 (10)
C11—C12—H12A	109.7	C33—C32—H32A	109.8
C13—C12—H12A	109.7	C31—C32—H32A	109.8
C11—C12—H12B	109.7	C33—C32—H32B	109.8
C13—C12—H12B	109.7	C31—C32—H32B	109.8
H12A—C12—H12B	108.2	H32A—C32—H32B	108.3
C17—C13—C12	109.70 (10)	C32—C33—C34	109.59 (10)
C17—C13—C14	109.32 (10)	C32—C33—C37	108.97 (9)
C12—C13—C14	109.46 (10)	C34—C33—C37	109.67 (10)
C17—C13—H13	109.4	C32—C33—H33	109.5
C12—C13—H13	109.4	C34—C33—H33	109.5
C14—C13—H13	109.4	C37—C33—H33	109.5
C13—C14—C15	109.23 (10)	C35—C34—C33	109.50 (10)
C13—C14—H14A	109.8	C35—C34—H34A	109.8
C15—C14—H14A	109.8	C33—C34—H34A	109.8
C13—C14—H14B	109.8	C35—C34—H34B	109.8
C15—C14—H14B	109.8	C33—C34—H34B	109.8
H14A—C14—H14B	108.3	H34A—C34—H34B	108.2
C16—C15—C18	109.12 (10)	C34—C35—C36	109.23 (10)
C16—C15—C14	109.64 (10)	C34—C35—C38	109.44 (10)
C18—C15—C14	109.32 (10)	C36—C35—C38	109.71 (9)
C16—C15—H15	109.6	C34—C35—H35	109.5
C18—C15—H15	109.6	C36—C35—H35	109.5
C14—C15—H15	109.6	C38—C35—H35	109.5
C15—C16—C9	110.55 (10)	C29—C36—C35	110.19 (10)
C15—C16—H16A	109.5	C29—C36—H36A	109.6
C9—C16—H16A	109.5	C35—C36—H36A	109.6
C15—C16—H16B	109.5	C29—C36—H36B	109.6
C9—C16—H16B	109.5	C35—C36—H36B	109.6
H16A—C16—H16B	108.1	H36A—C36—H36B	108.1
C13—C17—C9	110.37 (9)	C33—C37—C29	110.37 (9)
C13—C17—H17A	109.6	C33—C37—H37A	109.6
C9—C17—H17A	109.6	C29—C37—H37A	109.6
C13—C17—H17B	109.6	C33—C37—H37B	109.6
C9—C17—H17B	109.6	C29—C37—H37B	109.6
H17A—C17—H17B	108.1	H37A—C37—H37B	108.1
C11—C18—C15	109.76 (10)	C31—C38—C35	109.47 (10)
C11—C18—H18A	109.7	C31—C38—H38A	109.8
C15—C18—H18A	109.7	C35—C38—H38A	109.8
C11—C18—H18B	109.7	C31—C38—H38B	109.8
C15—C18—H18B	109.7	C35—C38—H38B	109.8
H18A—C18—H18B	108.2	H38A—C38—H38B	108.2

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	0.95	3.07	3.9197 (16)	150

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₂N₂
M_r	266.38
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	120
a, b, c (Å)	22.0249 (9), 6.4628 (1), 22.2739 (8)
β (°)	118.694 (5)
V (Å³)	2781.2 (2)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.08
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.928, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	32353, 4899, 3314
R_int	0.034
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.030, 0.064, 0.83
No. of reflections	4899
No. of parameters	361
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.16

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and Mercury (Macrae et al., 2008).

Hydrogen-bond geometry (Å, º) top

Cg1 is the centroid of the C2–C7 ring.

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	0.95	3.07	3.9197 (16)	149.5

Symmetry code: (i) x+1/2, −y+1/2, z+1/2.

Acknowledgements

The financial support of this work by the Czech Ministry of Education (project No. MSM 7088352101), the Internal Funding Agency of Tomas Bata University in Zlin, project No. IGA/6/FT/11/D and the Operational Program Research and Development for Innovations co-funded by the European Regional Development Fund (ERDF) and the national budget of the Czech Republic, within the framework of project Centre of Polymer Systems (reg. number: CZ.1.05/2.1.00/03.0111) is gratefully acknowledged.

References

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