1-(4-tert-Butyl­benz­yl)-2-(4-tert-butyl­phen­yl)-1H-benzimidazole

Zhou, J.-C.; Zhang, Z.-Y.; Li, N.-X.; Zhang, C.-M.

doi:10.1107/S1600536809045668

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 12| December 2009| Page o3019

doi:10.1107/S1600536809045668

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1-(4-tert-Butylbenzyl)-2-(4-tert-butylphenyl)-1H-benzimidazole

Jian-Cheng Zhou,^a,^b ^* Zheng-Yun Zhang,^a Nai-Xu Li ^a and Chuan-Ming Zhang ^a

^aCollege of Chemistry and Chemical Engineering, Southeast University, Nanjing 211189, People's Republic of China, and ^bJiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology, Nanjing Forestry University, Nanjing 210037, People's Republic of China
^*Correspondence e-mail: jczhou@seu.edu.cn

(Received 24 October 2009; accepted 30 October 2009; online 7 November 2009)

In the molecule of the title compound, C₂₈H₃₂N₂, the benzimidazole ring system is almost planar [maximum deviation = 0.0221 (15) Å] and forms dihedral angles of 85.86 (4) and 32.09 (6)° with the benzene rings. In the crystal structure, molecules are linked into chains running parallel to the a axis by intermolecular C—H⋯N hydrogen bonds. The methyl groups of a tert-butyl group are rotationally disordered over two positions with refined site-occupancy factors of 0.636 (4) and 0.364 (4).

Related literature

For the biological and pharmaceutical properties of benzimidazole derivatives, see: Matsuno et al. (2000 ). Garuti et al. (1999 ). For reference structural data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₈H₃₂N₂
M_r = 396.56
Monoclinic, P 2₁ /c
a = 6.2142 (5) Å
b = 21.1112 (13) Å
c = 17.4624 (12) Å
β = 92.869 (6)°
V = 2288.0 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.07 mm⁻¹
T = 293 K
0.20 × 0.20 × 0.10 mm

Data collection

Rigaku SCXmini diffractometer
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005 ) T_min = 0.987, T_max = 0.993
24819 measured reflections
5239 independent reflections
4315 reflections with I > 2σ(I)
R_int = 0.047

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.135
S = 1.09
5239 reflections
302 parameters
H-atom parameters constrained
Δρ_max = 0.22 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C18—H18A⋯N2ⁱ	0.97	2.59	3.553 (2)	174
Symmetry code: (i) x-1, y, z.

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear; data reduction: CrystalClear; 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.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809045668/rz2378sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809045668/rz2378Isup2.hkl

checkCIF report

Comment top

Imidazole and benzimidazole derivatives are important heteroaromatic compounds which have attracted great attention due to their biological and pharmaceutical activities (Matsuno et al., 2000; Garuti et al., 1999). These compounds have also played an important role in the development of coordination chemistry. In this paper, we report the crystal structure of the title compound.

The molecular structure of the title compound is shown in Fig. 1. Bond lengths (Allen et al., 1987) and angles are within normal ranges. The benzimidazole ring system is substantially planar, with a maximum displacement of 0.0221 (15) Å for atom C1. The dihedral angle it forms with the C8—C13 and C19—C24 benzene rings are 32.09 (6) and 85.86 (4) Å, respectively. The benzene rings are oriented perpendicularly to each other, forming a dihedral angle of 89.58 (5) °. In the crystal packing, the molecule are linked into chains running parallel to the a axis by intermolecular C—H···N hydrogen bonds (Table 1). The methyl groups of a tert-butyl group exhibits rotational disorder over two orientations with site occupation factors of 0.636 (4) and 0.364 (4) for the major and minor components of disorder, respectively.

Related literature top

For the biological and pharmaceutical properties of benzimidazole derivatives, see: Matsuno et al. (2000). Garuti et al. (1999). For reference structural data, see: Allen et al. (1987).

Experimental top

To a solution of o-phenylenediamine (0.432 g, 4 mmol) in ethanol(20 ml), 4-tert-butylbenzaldehyde (1.297 g, 8 mmol) was added. The mixture was heated to reflux with stirring for four hour, then cooled to room temperature. The resultant solution was filtered and allowed to evaporate slowly at room temperature. Colourless single crystals of the title compound suitable for X-ray diffraction study were obtained after several weeks.

Computing details top

Data collection: CrystalClear (Rigaku, 2005); cell refinement: CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing the atomic numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.

1-(4-tert-Butylbenzyl)-2-(4-tert-butylphenyl)-1H- benzimidazole top

Crystal data top

C₂₈H₃₂N₂	F(000) = 856
M_r = 396.56	D_x = 1.151 Mg m⁻³
Monoclinic, P2₁/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 3426 reflections
a = 6.2142 (5) Å	θ = 2.3–27.5°
b = 21.1112 (13) Å	µ = 0.07 mm⁻¹
c = 17.4624 (12) Å	T = 293 K
β = 92.869 (6)°	Block, colourless
V = 2288.0 (3) Å³	0.20 × 0.20 × 0.10 mm
Z = 4

Data collection top

Rigaku SCXmini diffractometer	5239 independent reflections
Radiation source: fine-focus sealed tube	4315 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.047
Detector resolution: 13.6612 pixels mm^-1	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −8→8
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	k = −27→27
T_min = 0.987, T_max = 0.993	l = −22→22
24819 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0431P)² + 0.936P] where P = (F_o² + 2F_c²)/3
5239 reflections	(Δ/σ)_max < 0.001
302 parameters	Δρ_max = 0.22 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₂₈H₃₂N₂	V = 2288.0 (3) Å³
M_r = 396.56	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 6.2142 (5) Å	µ = 0.07 mm⁻¹
b = 21.1112 (13) Å	T = 293 K
c = 17.4624 (12) Å	0.20 × 0.20 × 0.10 mm
β = 92.869 (6)°

Data collection top

Rigaku SCXmini diffractometer	5239 independent reflections
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005)	4315 reflections with I > 2σ(I)
T_min = 0.987, T_max = 0.993	R_int = 0.047
24819 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.09	Δρ_max = 0.22 e Å⁻³
5239 reflections	Δρ_min = −0.18 e Å⁻³
302 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 > 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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
N1	0.7010 (2)	0.17678 (6)	0.27399 (7)	0.0256 (3)
N2	1.0343 (2)	0.14275 (6)	0.31033 (7)	0.0298 (3)
C1	0.7112 (3)	0.17535 (7)	0.35346 (9)	0.0270 (3)
C2	0.5570 (3)	0.18846 (8)	0.40650 (10)	0.0346 (4)
H2B	0.4192	0.2021	0.3913	0.041*
C3	0.6195 (3)	0.18016 (9)	0.48290 (10)	0.0392 (4)
H3A	0.5214	0.1884	0.5201	0.047*
C4	0.8268 (3)	0.15961 (9)	0.50544 (10)	0.0382 (4)
H4A	0.8632	0.1547	0.5574	0.046*
C5	0.9793 (3)	0.14633 (8)	0.45281 (10)	0.0344 (4)
H5A	1.1170	0.1328	0.4684	0.041*
C6	0.9185 (3)	0.15411 (7)	0.37498 (9)	0.0282 (3)
C7	0.8992 (2)	0.15635 (7)	0.25137 (9)	0.0258 (3)
C8	0.9583 (2)	0.14654 (7)	0.17169 (9)	0.0272 (3)
C9	0.8876 (3)	0.18418 (8)	0.10959 (9)	0.0310 (4)
H9A	0.7887	0.2164	0.1168	0.037*
C10	0.9638 (3)	0.17391 (9)	0.03713 (10)	0.0355 (4)
H10A	0.9141	0.1995	−0.0033	0.043*
C11	1.1119 (3)	0.12648 (8)	0.02342 (10)	0.0344 (4)
C12	1.1810 (3)	0.08896 (8)	0.08579 (10)	0.0370 (4)
H12A	1.2802	0.0568	0.0785	0.044*
C13	1.1055 (3)	0.09845 (8)	0.15806 (10)	0.0335 (4)
H13A	1.1537	0.0723	0.1982	0.040*
C14	1.1974 (3)	0.11519 (9)	−0.05650 (10)	0.0424 (5)
C15	1.4372 (5)	0.1228 (2)	−0.0550 (2)	0.0569 (10)	0.636 (4)
H15A	1.4726	0.1670	−0.0576	0.085*	0.636 (4)
H15B	1.4930	0.1011	−0.0980	0.085*	0.636 (4)
H15C	1.4996	0.1051	−0.0083	0.085*	0.636 (4)
C16	1.1017 (6)	0.16598 (17)	−0.11722 (17)	0.0508 (9)	0.636 (4)
H16A	0.9475	0.1625	−0.1212	0.076*	0.636 (4)
H16B	1.1587	0.1580	−0.1664	0.076*	0.636 (4)
H16C	1.1414	0.2079	−0.1004	0.076*	0.636 (4)
C17	1.1189 (8)	0.0513 (2)	−0.0846 (2)	0.0687 (14)	0.636 (4)
H17A	0.9695	0.0541	−0.1011	0.103*	0.636 (4)
H17B	1.1360	0.0209	−0.0438	0.103*	0.636 (4)
H17C	1.2014	0.0381	−0.1268	0.103*	0.636 (4)
C16'	1.3128 (12)	0.1723 (4)	−0.0785 (4)	0.073 (2)	0.364 (4)
H16D	1.2128	0.2068	−0.0851	0.109*	0.364 (4)
H16E	1.3811	0.1648	−0.1258	0.109*	0.364 (4)
H16F	1.4201	0.1828	−0.0391	0.109*	0.364 (4)
C15'	1.3773 (13)	0.0576 (4)	−0.0524 (3)	0.077 (3)	0.364 (4)
H15D	1.3107	0.0193	−0.0360	0.116*	0.364 (4)
H15E	1.4934	0.0688	−0.0166	0.116*	0.364 (4)
H15F	1.4323	0.0514	−0.1023	0.116*	0.364 (4)
C17'	1.0230 (11)	0.0946 (4)	−0.1102 (3)	0.0593 (19)	0.364 (4)
H17D	0.9132	0.1266	−0.1137	0.089*	0.364 (4)
H17E	0.9627	0.0558	−0.0922	0.089*	0.364 (4)
H17F	1.0787	0.0879	−0.1598	0.089*	0.364 (4)
C18	0.5117 (2)	0.19700 (7)	0.22771 (9)	0.0276 (3)
H18A	0.3834	0.1845	0.2533	0.033*
H18B	0.5100	0.1753	0.1787	0.033*
C19	0.5039 (2)	0.26793 (7)	0.21354 (8)	0.0244 (3)
C20	0.6751 (3)	0.30771 (8)	0.23238 (10)	0.0345 (4)
H20A	0.7992	0.2912	0.2568	0.041*
C21	0.6647 (3)	0.37210 (8)	0.21545 (10)	0.0354 (4)
H21A	0.7823	0.3976	0.2292	0.042*
C22	0.4846 (2)	0.39941 (7)	0.17869 (9)	0.0255 (3)
C23	0.3127 (3)	0.35908 (8)	0.16148 (11)	0.0380 (4)
H23A	0.1875	0.3756	0.1379	0.046*
C24	0.3214 (3)	0.29478 (8)	0.17827 (11)	0.0370 (4)
H24A	0.2026	0.2694	0.1656	0.044*
C25	0.4755 (3)	0.47028 (7)	0.15925 (10)	0.0314 (4)
C26	0.6985 (3)	0.49533 (9)	0.14043 (12)	0.0454 (5)
H26A	0.7489	0.4729	0.0970	0.068*
H26B	0.7974	0.4891	0.1838	0.068*
H26C	0.6887	0.5397	0.1287	0.068*
C27	0.3234 (3)	0.48367 (9)	0.08955 (12)	0.0474 (5)
H27A	0.3723	0.4612	0.0459	0.071*
H27B	0.3218	0.5283	0.0791	0.071*
H27C	0.1806	0.4699	0.1000	0.071*
C28	0.3968 (4)	0.50619 (9)	0.22849 (12)	0.0586 (6)
H28A	0.2570	0.4909	0.2404	0.088*
H28B	0.3882	0.5506	0.2168	0.088*
H28C	0.4959	0.4997	0.2717	0.088*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1	0.0275 (7)	0.0240 (6)	0.0255 (7)	0.0003 (5)	0.0032 (5)	0.0028 (5)
N2	0.0303 (7)	0.0312 (7)	0.0280 (7)	0.0019 (5)	0.0030 (6)	0.0021 (6)
C1	0.0328 (8)	0.0225 (7)	0.0259 (8)	−0.0023 (6)	0.0048 (6)	0.0025 (6)
C2	0.0335 (9)	0.0364 (9)	0.0344 (9)	0.0014 (7)	0.0075 (7)	0.0009 (7)
C3	0.0449 (11)	0.0425 (10)	0.0311 (9)	−0.0027 (8)	0.0118 (8)	−0.0010 (8)
C4	0.0482 (11)	0.0403 (10)	0.0263 (9)	−0.0046 (8)	0.0030 (7)	0.0035 (7)
C5	0.0375 (9)	0.0350 (9)	0.0306 (9)	−0.0009 (7)	0.0007 (7)	0.0044 (7)
C6	0.0321 (8)	0.0255 (8)	0.0271 (8)	−0.0018 (6)	0.0038 (6)	0.0023 (6)
C7	0.0281 (8)	0.0217 (7)	0.0277 (8)	−0.0012 (6)	0.0038 (6)	0.0016 (6)
C8	0.0281 (8)	0.0261 (8)	0.0276 (8)	−0.0049 (6)	0.0029 (6)	−0.0006 (6)
C9	0.0323 (9)	0.0304 (8)	0.0303 (9)	−0.0015 (7)	0.0032 (7)	0.0001 (7)
C10	0.0395 (10)	0.0388 (9)	0.0282 (9)	−0.0057 (7)	0.0023 (7)	0.0015 (7)
C11	0.0351 (9)	0.0387 (9)	0.0300 (9)	−0.0102 (7)	0.0067 (7)	−0.0082 (7)
C12	0.0371 (10)	0.0354 (9)	0.0391 (10)	0.0023 (7)	0.0076 (8)	−0.0077 (8)
C13	0.0353 (9)	0.0323 (9)	0.0330 (9)	0.0015 (7)	0.0034 (7)	−0.0003 (7)
C14	0.0468 (11)	0.0484 (11)	0.0333 (10)	−0.0098 (9)	0.0136 (8)	−0.0078 (8)
C15	0.048 (2)	0.078 (3)	0.047 (2)	0.0041 (18)	0.0199 (15)	0.0108 (18)
C16	0.056 (2)	0.070 (2)	0.0278 (15)	−0.0027 (17)	0.0097 (14)	0.0037 (15)
C17	0.105 (4)	0.059 (2)	0.045 (2)	−0.023 (2)	0.032 (2)	−0.0254 (19)
C16'	0.081 (6)	0.077 (5)	0.063 (4)	−0.019 (4)	0.041 (4)	−0.001 (4)
C15'	0.095 (6)	0.103 (6)	0.036 (3)	0.056 (5)	0.024 (3)	0.003 (4)
C17'	0.069 (4)	0.073 (5)	0.036 (3)	0.006 (3)	0.002 (3)	−0.015 (3)
C18	0.0254 (8)	0.0258 (8)	0.0316 (8)	−0.0026 (6)	−0.0001 (6)	0.0012 (6)
C19	0.0251 (8)	0.0247 (7)	0.0236 (7)	−0.0008 (6)	0.0039 (6)	−0.0004 (6)
C20	0.0289 (9)	0.0296 (8)	0.0437 (10)	−0.0010 (6)	−0.0107 (7)	0.0043 (7)
C21	0.0303 (9)	0.0272 (8)	0.0476 (11)	−0.0054 (6)	−0.0080 (7)	0.0018 (7)
C22	0.0273 (8)	0.0250 (7)	0.0243 (8)	0.0017 (6)	0.0041 (6)	−0.0007 (6)
C23	0.0271 (9)	0.0309 (9)	0.0548 (11)	0.0012 (7)	−0.0097 (8)	0.0059 (8)
C24	0.0260 (8)	0.0303 (9)	0.0538 (11)	−0.0057 (7)	−0.0074 (7)	0.0032 (8)
C25	0.0382 (9)	0.0248 (8)	0.0316 (9)	0.0022 (7)	0.0056 (7)	0.0022 (7)
C26	0.0454 (11)	0.0331 (9)	0.0576 (12)	−0.0072 (8)	0.0028 (9)	0.0099 (9)
C27	0.0487 (12)	0.0408 (10)	0.0525 (12)	0.0016 (9)	−0.0011 (9)	0.0176 (9)
C28	0.1005 (19)	0.0285 (9)	0.0493 (12)	0.0113 (10)	0.0287 (12)	0.0019 (9)

Geometric parameters (Å, º) top

N1—C7	1.3816 (19)	C17—H17A	0.9600
N1—C1	1.386 (2)	C17—H17B	0.9600
N1—C18	1.4571 (19)	C17—H17C	0.9600
N2—C7	1.327 (2)	C16'—H16D	0.9600
N2—C6	1.390 (2)	C16'—H16E	0.9600
C1—C2	1.393 (2)	C16'—H16F	0.9600
C1—C6	1.398 (2)	C15'—H15D	0.9600
C2—C3	1.382 (2)	C15'—H15E	0.9600
C2—H2B	0.9300	C15'—H15F	0.9600
C3—C4	1.397 (3)	C17'—H17D	0.9600
C3—H3A	0.9300	C17'—H17E	0.9600
C4—C5	1.381 (2)	C17'—H17F	0.9600
C4—H4A	0.9300	C18—C19	1.518 (2)
C5—C6	1.402 (2)	C18—H18A	0.9700
C5—H5A	0.9300	C18—H18B	0.9700
C7—C8	1.471 (2)	C19—C20	1.382 (2)
C8—C13	1.395 (2)	C19—C24	1.385 (2)
C8—C9	1.397 (2)	C20—C21	1.392 (2)
C9—C10	1.390 (2)	C20—H20A	0.9300
C9—H9A	0.9300	C21—C22	1.387 (2)
C10—C11	1.389 (2)	C21—H21A	0.9300
C10—H10A	0.9300	C22—C23	1.387 (2)
C11—C12	1.397 (3)	C22—C25	1.535 (2)
C11—C14	1.536 (2)	C23—C24	1.389 (2)
C12—C13	1.383 (2)	C23—H23A	0.9300
C12—H12A	0.9300	C24—H24A	0.9300
C13—H13A	0.9300	C25—C28	1.528 (2)
C14—C17'	1.463 (6)	C25—C27	1.530 (2)
C14—C16'	1.465 (7)	C25—C26	1.534 (2)
C14—C15	1.498 (4)	C26—H26A	0.9600
C14—C17	1.508 (4)	C26—H26B	0.9600
C14—C16	1.601 (4)	C26—H26C	0.9600
C14—C15'	1.650 (6)	C27—H27A	0.9600
C15—H15A	0.9600	C27—H27B	0.9600
C15—H15B	0.9600	C27—H27C	0.9600
C15—H15C	0.9600	C28—H28A	0.9600
C16—H16A	0.9600	C28—H28B	0.9600
C16—H16B	0.9600	C28—H28C	0.9600
C16—H16C	0.9600

C7—N1—C1	106.40 (13)	C14—C17—H17A	109.5
C7—N1—C18	129.74 (13)	C14—C17—H17B	109.5
C1—N1—C18	123.86 (13)	H17A—C17—H17B	109.5
C7—N2—C6	105.05 (13)	C14—C17—H17C	109.5
N1—C1—C2	131.48 (15)	H17A—C17—H17C	109.5
N1—C1—C6	105.77 (13)	H17B—C17—H17C	109.5
C2—C1—C6	122.70 (15)	C14—C16'—H16D	109.5
C3—C2—C1	116.56 (16)	C14—C16'—H16E	109.5
C3—C2—H2B	121.7	H16D—C16'—H16E	109.5
C1—C2—H2B	121.7	C14—C16'—H16F	109.5
C2—C3—C4	121.47 (16)	H16D—C16'—H16F	109.5
C2—C3—H3A	119.3	H16E—C16'—H16F	109.5
C4—C3—H3A	119.3	C14—C15'—H15D	109.5
C5—C4—C3	121.94 (16)	C14—C15'—H15E	109.5
C5—C4—H4A	119.0	H15D—C15'—H15E	109.5
C3—C4—H4A	119.0	C14—C15'—H15F	109.5
C4—C5—C6	117.44 (16)	H15D—C15'—H15F	109.5
C4—C5—H5A	121.3	H15E—C15'—H15F	109.5
C6—C5—H5A	121.3	C14—C17'—H17D	109.5
N2—C6—C1	110.16 (13)	C14—C17'—H17E	109.5
N2—C6—C5	129.95 (15)	H17D—C17'—H17E	109.5
C1—C6—C5	119.88 (15)	C14—C17'—H17F	109.5
N2—C7—N1	112.61 (14)	H17D—C17'—H17F	109.5
N2—C7—C8	121.68 (14)	H17E—C17'—H17F	109.5
N1—C7—C8	125.63 (14)	N1—C18—C19	113.43 (12)
C13—C8—C9	117.69 (15)	N1—C18—H18A	108.9
C13—C8—C7	117.42 (14)	C19—C18—H18A	108.9
C9—C8—C7	124.78 (14)	N1—C18—H18B	108.9
C10—C9—C8	120.65 (16)	C19—C18—H18B	108.9
C10—C9—H9A	119.7	H18A—C18—H18B	107.7
C8—C9—H9A	119.7	C20—C19—C24	117.44 (14)
C11—C10—C9	121.88 (16)	C20—C19—C18	122.86 (14)
C11—C10—H10A	119.1	C24—C19—C18	119.67 (14)
C9—C10—H10A	119.1	C19—C20—C21	121.05 (15)
C10—C11—C12	117.05 (15)	C19—C20—H20A	119.5
C10—C11—C14	122.04 (17)	C21—C20—H20A	119.5
C12—C11—C14	120.91 (16)	C22—C21—C20	122.13 (15)
C13—C12—C11	121.63 (16)	C22—C21—H21A	118.9
C13—C12—H12A	119.2	C20—C21—H21A	118.9
C11—C12—H12A	119.2	C23—C22—C21	116.09 (14)
C12—C13—C8	121.10 (16)	C23—C22—C25	122.07 (14)
C12—C13—H13A	119.5	C21—C22—C25	121.83 (14)
C8—C13—H13A	119.5	C22—C23—C24	122.19 (15)
C17'—C14—C16'	115.7 (5)	C22—C23—H23A	118.9
C17'—C14—C15	138.4 (3)	C24—C23—H23A	118.9
C16'—C14—C15	54.3 (4)	C19—C24—C23	121.07 (15)
C17'—C14—C17	46.3 (3)	C19—C24—H24A	119.5
C16'—C14—C17	143.7 (3)	C23—C24—H24A	119.5
C15—C14—C17	114.0 (3)	C28—C25—C27	109.18 (16)
C17'—C14—C11	110.5 (3)	C28—C25—C26	109.07 (16)
C16'—C14—C11	107.9 (3)	C27—C25—C26	107.14 (15)
C15—C14—C11	110.84 (19)	C28—C25—C22	108.57 (14)
C17—C14—C11	108.26 (19)	C27—C25—C22	111.76 (14)
C17'—C14—C16	62.4 (3)	C26—C25—C22	111.08 (14)
C16'—C14—C16	56.3 (4)	C25—C26—H26A	109.5
C15—C14—C16	106.1 (2)	C25—C26—H26B	109.5
C17—C14—C16	106.3 (3)	H26A—C26—H26B	109.5
C11—C14—C16	111.34 (18)	C25—C26—H26C	109.5
C17'—C14—C15'	106.7 (4)	H26A—C26—H26C	109.5
C16'—C14—C15'	106.2 (5)	H26B—C26—H26C	109.5
C15—C14—C15'	53.6 (4)	C25—C27—H27A	109.5
C17—C14—C15'	64.1 (4)	C25—C27—H27B	109.5
C11—C14—C15'	109.8 (2)	H27A—C27—H27B	109.5
C16—C14—C15'	138.6 (3)	C25—C27—H27C	109.5
C14—C15—H15A	109.5	H27A—C27—H27C	109.5
C14—C15—H15B	109.5	H27B—C27—H27C	109.5
H15A—C15—H15B	109.5	C25—C28—H28A	109.5
C14—C15—H15C	109.5	C25—C28—H28B	109.5
H15A—C15—H15C	109.5	H28A—C28—H28B	109.5
H15B—C15—H15C	109.5	C25—C28—H28C	109.5
C14—C16—H16A	109.5	H28A—C28—H28C	109.5
C14—C16—H16B	109.5	H28B—C28—H28C	109.5
C14—C16—H16C	109.5

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N2ⁱ	0.97	2.59	3.553 (2)	174

Symmetry code: (i) x−1, y, z.

Experimental details

Crystal data
Chemical formula	C₂₈H₃₂N₂
M_r	396.56
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	6.2142 (5), 21.1112 (13), 17.4624 (12)
β (°)	92.869 (6)
V (Å³)	2288.0 (3)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.20 × 0.20 × 0.10

Data collection
Diffractometer	Rigaku SCXmini diffractometer
Absorption correction	Multi-scan (CrystalClear; Rigaku, 2005)
T_min, T_max	0.987, 0.993
No. of measured, independent and observed [I > 2σ(I)] reflections	24819, 5239, 4315
R_int	0.047
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.135, 1.09
No. of reflections	5239
No. of parameters	302
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.22, −0.18

Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C18—H18A···N2ⁱ	0.97	2.59	3.553 (2)	174

Symmetry code: (i) x−1, y, z.

Acknowledgements

This work was financially supported by the Jiangsu Provincial Key Laboratory of Pulp and Paper Science and Technology Fund (No. 200813).

References

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