4-[2-(Dibenzyl­amino­meth­yl)-1H-benz­imidazol-1-ylmeth­yl]benzonitrile

Ping, G.-J.; Liu, Y.-Y.; Han, T.-T.; Ma, J.-F.

doi:10.1107/S1600536807053573

4-[2-(Dibenzylaminomethyl)-1H-benzimidazol-1-ylmethyl]benzonitrile

G.-J. Ping, Y.-Y. Liu, T.-T. Han and J.-F. Ma

The molecule of the title compound, C₃₀H₂₆N₄, is non-planar. The dihedral angles between the two benzene rings of the benzyl groups, and between the benzimidazole and 4-(methyl)benzonitrile ring systems, are 117.9 (2) and 70.3 (3)°, respectively. The bond distances and angles are all in normal ranges.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807053573/wn2213sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807053573/wn2213Isup2.hkl Contains datablock I

CCDC reference: 672789

checkCIF report

Key indicators

Single-crystal X-ray study
T = 293 K
Mean (C-C) = 0.002 Å
R factor = 0.040
wR factor = 0.120
Data-to-parameter ratio = 19.7

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT152_ALERT_1_C Supplied and Calc Volume s.u. Inconsistent .....          ?
PLAT153_ALERT_1_C The su's on the Cell Axes   are Equal (x 100000)        100 Ang.
PLAT180_ALERT_3_C Check Cell Rounding: # of Values Ending with 0 =          3
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.54 Ratio
PLAT242_ALERT_2_C Check Low       Ueq as Compared to Neighbors for        C11
PLAT371_ALERT_2_C Long   C(sp2)-C(sp1) Bond  C27    -   C30    ...       1.44 Ang.

Alert level G
PLAT199_ALERT_1_G Check the Reported _cell_measurement_temperature        293 K
PLAT200_ALERT_1_G Check the Reported _diffrn_ambient_temperature .        293 K

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   5 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   3 ALERT type 2 Indicator that the structure model may be wrong or deficient
   1 ALERT type 3 Indicator that the structure quality may be low
   0 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

For many years there has been extensive research on the reactions of benzimidazole derivatives with transition metals, as models of some important biological molecules, due to their varied pharmacological activities (Spasov et al., 1999; Keeffe et al., 2000; Feng & Xu, 2001; Ferey, 2001). To further widen the scope of research on the coordination chemistry of benzimidazole derivatives, there is a need to prepare a new series of benzimidazole derivatives. In this paper, the structure of the title compound is described.

As shown in Fig. 1, the molecular skeleton is non-planar. The dihedral angles between the two benzene rings of the benzyl groups, and between the benzimidazole and 4-(methyl)benzonitrile ring systems are 117.9 (2) and 70.3 (3)°, respectively. The bond distances and bond angles are all in normal ranges (Pandiyan et al., 1997; Barros-García et al., 2005; Maldonado-Rogado et al., 2007).

Related literature top

For related literature, see: Spasov et al., 1999; O'Keeffe et al., 2000; Feng & Xu, 2001; Ferey, 2001; Pandiyan et al., 1997; Barros-García et al., 2005; Maldonado-Rogado et al., 2007.

Experimental top

A mixture of N,N-dibenzylglycine (10.2 g, 40 mmol) and o-phenylenediamine (4.32 g, 40 mmol) in ethanediol (70 ml) was heated to reflux for 16 h. The mixture was cooled to room temperature, added to hot water and stirred continuously until brown solids were obtained and then filtered. The solid was purified by recrystallization from an ethanol–water solution (1:1 v/v) to yield L (where L is (1H-benzo[d]imidazol-2-yl)-N,N-dibenzylmethanamine). Sodium hydroxide (1.2 g) was added to a DMF solution (15 ml) of L (9.39 g, 30 mmol). The mixture was stirred at room temperature for 2 h in air. 4-(Chloromethyl)benzonitrile (4.55 g, 30 mmol) was then added and the mixture stirred for 1 d. After evaporation of DMF, the mixture was added to hot water. The brown solids obtained were filtered and dried in air. Colorless crystals suitable for X-ray diffraction study were obtained by slow evaporation of an ethanol solution.

Computing details top

Data collection: SMART (Bruker, 1997); cell refinement: SAINT (Bruker, 1999); data reduction: SAINT (Bruker, 1999); program(s) used to solve structure: SHELXS97 (Sheldrick, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL-Plus (Sheldrick, 1990); software used to prepare material for publication: SHELXL97 (Sheldrick, 1997).

Figures top

Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 30% probability level. The H atoms have been omitted for clarity.

4-[2-(Dibenzylaminomethyl)-1H-benzimidazol-1-ylmethyl]benzonitrile top

Crystal data top

C₃₀H₂₆N₄	F(000) = 1872
M_r = 442.55	D_x = 1.190 Mg m⁻³
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71069 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 4045 reflections
a = 15.364 (1) Å	θ = 2.1–28.4°
b = 17.006 (1) Å	µ = 0.07 mm⁻¹
c = 18.908 (1) Å	T = 293 K
V = 4940.3 (4) Å³	Block, colourless
Z = 8	0.46 × 0.34 × 0.21 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	6054 independent reflections
Radiation source: fine-focus sealed tube	4045 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.027
ω scans	θ_max = 28.4°, θ_min = 2.1°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −20→18
T_min = 0.971, T_max = 0.985	k = −22→21
28803 measured reflections	l = −24→23

Refinement top

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-atom parameters constrained
wR(F²) = 0.120	w = 1/[σ²(F_o²) + (0.0524P)² + 0.5735P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
6054 reflections	Δρ_max = 0.13 e Å⁻³
308 parameters	Δρ_min = −0.16 e Å⁻³
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 1997), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0020 (4)

Crystal data top

C₃₀H₂₆N₄	V = 4940.3 (4) Å³
M_r = 442.55	Z = 8
Orthorhombic, Pbca	Mo Kα radiation
a = 15.364 (1) Å	µ = 0.07 mm⁻¹
b = 17.006 (1) Å	T = 293 K
c = 18.908 (1) Å	0.46 × 0.34 × 0.21 mm

Data collection top

Bruker APEX CCD area-detector diffractometer	6054 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	4045 reflections with I > 2σ(I)
T_min = 0.971, T_max = 0.985	R_int = 0.027
28803 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.040	0 restraints
wR(F²) = 0.120	H-atom parameters constrained
S = 1.01	Δρ_max = 0.13 e Å⁻³
6054 reflections	Δρ_min = −0.16 e Å⁻³
308 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
C1	−0.08980 (14)	0.47828 (12)	0.62575 (17)	0.1197 (9)
H1	−0.0840	0.5327	0.6250	0.144*
C2	−0.11047 (13)	0.44125 (12)	0.68656 (14)	0.1054 (7)
H2	−0.1173	0.4702	0.7279	0.126*
C3	−0.12144 (10)	0.36140 (9)	0.68776 (8)	0.0747 (4)
H3	−0.1369	0.3368	0.7299	0.090*
C4	−0.10992 (8)	0.31674 (8)	0.62744 (7)	0.0554 (3)
C5	−0.08677 (10)	0.35415 (10)	0.56584 (9)	0.0762 (4)
H5	−0.0775	0.3250	0.5249	0.091*
C6	−0.07719 (13)	0.43496 (13)	0.56432 (14)	0.1084 (7)
H6	−0.0624	0.4602	0.5224	0.130*
C7	−0.12267 (8)	0.22928 (8)	0.62758 (7)	0.0610 (3)
H7A	−0.1489	0.2135	0.6721	0.073*
H7B	−0.1624	0.2150	0.5899	0.073*
C8	−0.17796 (16)	0.06684 (12)	0.40156 (13)	0.1079 (7)
H8	−0.2038	0.0587	0.3577	0.129*
C9	−0.09697 (15)	0.09825 (15)	0.40578 (10)	0.1165 (7)
H9	−0.0673	0.1118	0.3647	0.140*
C10	−0.05855 (12)	0.11010 (13)	0.47080 (9)	0.0982 (6)
H10	−0.0030	0.1316	0.4728	0.118*
C11	−0.10049 (9)	0.09085 (8)	0.53285 (8)	0.0658 (4)
C12	−0.18332 (11)	0.05982 (8)	0.52768 (10)	0.0815 (5)
H12	−0.2140	0.0472	0.5685	0.098*
C13	−0.22112 (13)	0.04736 (10)	0.46157 (14)	0.1022 (7)
H13	−0.2765	0.0255	0.4586	0.123*
C14	−0.05651 (10)	0.10309 (8)	0.60316 (8)	0.0672 (4)
H14A	−0.0929	0.0814	0.6403	0.081*
H14B	−0.0016	0.0749	0.6035	0.081*
C15	0.01235 (8)	0.19572 (8)	0.68250 (6)	0.0548 (3)
H15A	−0.0154	0.1664	0.7203	0.066*
H15B	0.0124	0.2507	0.6960	0.066*
C16	0.10411 (7)	0.16876 (7)	0.67610 (5)	0.0472 (3)
C17	0.24253 (8)	0.16810 (8)	0.64567 (6)	0.0537 (3)
C18	0.22577 (8)	0.11201 (7)	0.69749 (6)	0.0528 (3)
C19	0.29279 (10)	0.06283 (9)	0.72069 (7)	0.0689 (4)
H19	0.2830	0.0248	0.7551	0.083*
C20	0.37359 (10)	0.07248 (11)	0.69101 (9)	0.0821 (5)
H20	0.4188	0.0394	0.7047	0.099*
C21	0.38938 (10)	0.13020 (12)	0.64117 (9)	0.0872 (5)
H21	0.4454	0.1360	0.6234	0.105*
C22	0.32479 (10)	0.17923 (11)	0.61709 (8)	0.0754 (4)
H22	0.3356	0.2179	0.5834	0.090*
C23	0.14828 (9)	0.26609 (7)	0.58130 (6)	0.0560 (3)
H23A	0.1924	0.3063	0.5879	0.067*
H23B	0.0921	0.2898	0.5911	0.067*
C24	0.14997 (7)	0.23942 (7)	0.50493 (6)	0.0489 (3)
C25	0.16991 (9)	0.16342 (8)	0.48514 (6)	0.0601 (3)
H25	0.1829	0.1263	0.5197	0.072*
C26	0.17090 (9)	0.14185 (8)	0.41474 (6)	0.0635 (3)
H26	0.1849	0.0905	0.4021	0.076*
C27	0.15110 (8)	0.19628 (8)	0.36307 (6)	0.0580 (3)
C28	0.13195 (10)	0.27277 (9)	0.38191 (7)	0.0663 (4)
H28	0.1194	0.3099	0.3473	0.080*
C29	0.13160 (9)	0.29372 (8)	0.45235 (6)	0.0606 (3)
H29	0.1188	0.3453	0.4648	0.073*
C30	0.15169 (10)	0.17137 (10)	0.29035 (7)	0.0736 (4)
N1	−0.04017 (7)	0.18681 (6)	0.61800 (5)	0.0527 (2)
N2	0.13861 (7)	0.11413 (6)	0.71633 (5)	0.0536 (3)
N3	0.16329 (6)	0.20334 (6)	0.63191 (5)	0.0504 (2)
N4	0.15204 (12)	0.14906 (10)	0.23346 (7)	0.1052 (5)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0947 (14)	0.0548 (10)	0.210 (3)	0.0029 (10)	−0.0439 (16)	−0.0018 (15)
C2	0.0931 (13)	0.0756 (12)	0.1474 (19)	0.0199 (10)	−0.0303 (13)	−0.0472 (13)
C3	0.0694 (9)	0.0785 (10)	0.0762 (9)	0.0104 (7)	−0.0056 (7)	−0.0214 (8)
C4	0.0467 (6)	0.0582 (7)	0.0614 (7)	0.0042 (5)	−0.0076 (5)	−0.0073 (6)
C5	0.0748 (9)	0.0791 (10)	0.0747 (9)	0.0014 (8)	−0.0051 (7)	0.0069 (8)
C6	0.0946 (13)	0.0875 (14)	0.1432 (19)	−0.0084 (11)	−0.0132 (12)	0.0443 (13)
C7	0.0522 (7)	0.0614 (8)	0.0694 (8)	−0.0022 (6)	−0.0032 (6)	−0.0063 (6)
C8	0.1210 (17)	0.0899 (13)	0.1127 (15)	0.0133 (12)	−0.0526 (14)	−0.0422 (12)
C9	0.1190 (17)	0.155 (2)	0.0754 (11)	−0.0052 (14)	−0.0177 (11)	−0.0345 (12)
C10	0.0801 (11)	0.1364 (17)	0.0782 (11)	−0.0152 (10)	−0.0102 (9)	−0.0273 (11)
C11	0.0706 (8)	0.0475 (7)	0.0793 (9)	0.0028 (6)	−0.0175 (7)	−0.0124 (6)
C12	0.0803 (10)	0.0516 (8)	0.1125 (13)	−0.0067 (7)	−0.0212 (9)	0.0014 (8)
C13	0.0876 (12)	0.0633 (10)	0.1558 (19)	−0.0059 (9)	−0.0520 (13)	−0.0170 (11)
C14	0.0773 (9)	0.0517 (7)	0.0726 (9)	−0.0001 (6)	−0.0143 (7)	−0.0022 (6)
C15	0.0574 (7)	0.0642 (7)	0.0429 (6)	−0.0006 (6)	−0.0003 (5)	−0.0019 (5)
C16	0.0568 (6)	0.0494 (6)	0.0354 (5)	−0.0047 (5)	−0.0034 (5)	−0.0002 (4)
C17	0.0566 (7)	0.0633 (7)	0.0412 (5)	−0.0009 (6)	−0.0036 (5)	−0.0030 (5)
C18	0.0605 (7)	0.0549 (7)	0.0429 (6)	−0.0009 (5)	−0.0124 (5)	−0.0037 (5)
C19	0.0745 (9)	0.0676 (8)	0.0647 (8)	0.0057 (7)	−0.0247 (7)	−0.0001 (6)
C20	0.0673 (9)	0.1006 (12)	0.0786 (10)	0.0198 (8)	−0.0242 (8)	−0.0130 (9)
C21	0.0541 (8)	0.1271 (15)	0.0804 (10)	0.0065 (9)	−0.0028 (7)	−0.0091 (10)
C22	0.0619 (8)	0.1020 (12)	0.0622 (8)	−0.0049 (8)	0.0044 (6)	0.0049 (8)
C23	0.0727 (8)	0.0505 (7)	0.0448 (6)	−0.0016 (6)	0.0007 (5)	0.0078 (5)
C24	0.0505 (6)	0.0530 (7)	0.0432 (6)	−0.0011 (5)	0.0019 (5)	0.0089 (5)
C25	0.0802 (9)	0.0547 (7)	0.0455 (6)	0.0085 (6)	−0.0031 (6)	0.0119 (5)
C26	0.0827 (9)	0.0584 (8)	0.0494 (7)	0.0141 (7)	0.0002 (6)	0.0038 (6)
C27	0.0605 (7)	0.0709 (8)	0.0426 (6)	0.0110 (6)	0.0019 (5)	0.0084 (5)
C28	0.0843 (9)	0.0670 (9)	0.0477 (7)	0.0148 (7)	−0.0026 (6)	0.0167 (6)
C29	0.0767 (8)	0.0534 (7)	0.0518 (7)	0.0091 (6)	0.0002 (6)	0.0090 (5)
C30	0.0925 (11)	0.0825 (10)	0.0457 (7)	0.0264 (8)	−0.0012 (7)	0.0088 (7)
N1	0.0551 (6)	0.0512 (6)	0.0520 (5)	0.0011 (4)	−0.0081 (4)	−0.0055 (4)
N2	0.0627 (6)	0.0553 (6)	0.0429 (5)	−0.0051 (5)	−0.0079 (4)	0.0071 (4)
N3	0.0575 (6)	0.0545 (6)	0.0391 (5)	0.0007 (4)	−0.0004 (4)	0.0060 (4)
N4	0.1612 (15)	0.1052 (11)	0.0493 (7)	0.0442 (10)	−0.0050 (8)	0.0015 (7)

Geometric parameters (Å, º) top

C1—C2	1.349 (3)	C15—H15A	0.9700
C1—C6	1.389 (3)	C15—H15B	0.9700
C1—H1	0.9300	C16—N2	1.3124 (14)
C2—C3	1.368 (3)	C16—N3	1.3678 (14)
C2—H2	0.9300	C17—N3	1.3817 (15)
C3—C4	1.3817 (18)	C17—C22	1.3874 (19)
C3—H3	0.9300	C17—C18	1.3916 (17)
C4—C5	1.374 (2)	C18—N2	1.3862 (16)
C4—C7	1.5003 (18)	C18—C19	1.3972 (18)
C5—C6	1.382 (3)	C19—C20	1.372 (2)
C5—H5	0.9300	C19—H19	0.9300
C6—H6	0.9300	C20—C21	1.382 (2)
C7—N1	1.4700 (16)	C20—H20	0.9300
C7—H7A	0.9700	C21—C22	1.374 (2)
C7—H7B	0.9700	C21—H21	0.9300
C8—C13	1.355 (3)	C22—H22	0.9300
C8—C9	1.356 (3)	C23—N3	1.4517 (15)
C8—H8	0.9300	C23—C24	1.5138 (16)
C9—C10	1.378 (2)	C23—H23A	0.9700
C9—H9	0.9300	C23—H23B	0.9700
C10—C11	1.378 (2)	C24—C25	1.3799 (17)
C10—H10	0.9300	C24—C29	1.3860 (16)
C11—C12	1.381 (2)	C25—C26	1.3808 (17)
C11—C14	1.5058 (19)	C25—H25	0.9300
C12—C13	1.395 (3)	C26—C27	1.3797 (17)
C12—H12	0.9300	C26—H26	0.9300
C13—H13	0.9300	C27—C28	1.381 (2)
C14—N1	1.4727 (16)	C27—C30	1.4388 (18)
C14—H14A	0.9700	C28—C29	1.3788 (18)
C14—H14B	0.9700	C28—H28	0.9300
C15—N1	1.4703 (14)	C29—H29	0.9300
C15—C16	1.4874 (17)	C30—N4	1.1406 (18)

C2—C1—C6	119.87 (19)	N2—C16—N3	112.95 (10)
C2—C1—H1	120.1	N2—C16—C15	123.63 (10)
C6—C1—H1	120.1	N3—C16—C15	123.18 (10)
C1—C2—C3	120.42 (19)	N3—C17—C22	132.08 (12)
C1—C2—H2	119.8	N3—C17—C18	105.48 (10)
C3—C2—H2	119.8	C22—C17—C18	122.43 (12)
C2—C3—C4	121.06 (18)	N2—C18—C17	109.99 (10)
C2—C3—H3	119.5	N2—C18—C19	130.31 (12)
C4—C3—H3	119.5	C17—C18—C19	119.67 (12)
C5—C4—C3	118.58 (14)	C20—C19—C18	117.83 (14)
C5—C4—C7	119.63 (12)	C20—C19—H19	121.1
C3—C4—C7	121.79 (13)	C18—C19—H19	121.1
C4—C5—C6	120.36 (18)	C19—C20—C21	121.51 (14)
C4—C5—H5	119.8	C19—C20—H20	119.2
C6—C5—H5	119.8	C21—C20—H20	119.2
C5—C6—C1	119.7 (2)	C22—C21—C20	122.02 (15)
C5—C6—H6	120.2	C22—C21—H21	119.0
C1—C6—H6	120.2	C20—C21—H21	119.0
N1—C7—C4	111.98 (10)	C21—C22—C17	116.50 (15)
N1—C7—H7A	109.2	C21—C22—H22	121.8
C4—C7—H7A	109.2	C17—C22—H22	121.8
N1—C7—H7B	109.2	N3—C23—C24	113.93 (10)
C4—C7—H7B	109.2	N3—C23—H23A	108.8
H7A—C7—H7B	107.9	C24—C23—H23A	108.8
C13—C8—C9	119.73 (18)	N3—C23—H23B	108.8
C13—C8—H8	120.1	C24—C23—H23B	108.8
C9—C8—H8	120.1	H23A—C23—H23B	107.7
C8—C9—C10	120.2 (2)	C25—C24—C29	118.34 (11)
C8—C9—H9	119.9	C25—C24—C23	122.90 (10)
C10—C9—H9	119.9	C29—C24—C23	118.76 (11)
C11—C10—C9	121.63 (18)	C24—C25—C26	120.84 (11)
C11—C10—H10	119.2	C24—C25—H25	119.6
C9—C10—H10	119.2	C26—C25—H25	119.6
C10—C11—C12	117.48 (14)	C27—C26—C25	120.14 (12)
C10—C11—C14	120.61 (14)	C27—C26—H26	119.9
C12—C11—C14	121.91 (15)	C25—C26—H26	119.9
C11—C12—C13	120.35 (18)	C26—C27—C28	119.76 (11)
C11—C12—H12	119.8	C26—C27—C30	118.55 (13)
C13—C12—H12	119.8	C28—C27—C30	121.69 (12)
C8—C13—C12	120.63 (18)	C29—C28—C27	119.57 (11)
C8—C13—H13	119.7	C29—C28—H28	120.2
C12—C13—H13	119.7	C27—C28—H28	120.2
N1—C14—C11	112.22 (11)	C28—C29—C24	121.34 (12)
N1—C14—H14A	109.2	C28—C29—H29	119.3
C11—C14—H14A	109.2	C24—C29—H29	119.3
N1—C14—H14B	109.2	N4—C30—C27	177.69 (18)
C11—C14—H14B	109.2	C7—N1—C15	108.68 (9)
H14A—C14—H14B	107.9	C7—N1—C14	110.58 (10)
N1—C15—C16	114.89 (9)	C15—N1—C14	110.55 (10)
N1—C15—H15A	108.5	C16—N2—C18	105.05 (10)
C16—C15—H15A	108.5	C16—N3—C17	106.51 (9)
N1—C15—H15B	108.5	C16—N3—C23	127.82 (10)
C16—C15—H15B	108.5	C17—N3—C23	125.66 (10)
H15A—C15—H15B	107.5

C6—C1—C2—C3	−1.8 (3)	N3—C23—C24—C25	−4.22 (17)
C1—C2—C3—C4	1.4 (3)	N3—C23—C24—C29	176.46 (11)
C2—C3—C4—C5	0.2 (2)	C29—C24—C25—C26	−0.48 (19)
C2—C3—C4—C7	−179.29 (14)	C23—C24—C25—C26	−179.80 (13)
C3—C4—C5—C6	−1.4 (2)	C24—C25—C26—C27	−0.5 (2)
C7—C4—C5—C6	178.15 (14)	C25—C26—C27—C28	1.3 (2)
C4—C5—C6—C1	1.0 (3)	C25—C26—C27—C30	−179.20 (14)
C2—C1—C6—C5	0.6 (3)	C26—C27—C28—C29	−0.9 (2)
C5—C4—C7—N1	69.27 (16)	C30—C27—C28—C29	179.54 (14)
C3—C4—C7—N1	−111.21 (14)	C27—C28—C29—C24	−0.1 (2)
C13—C8—C9—C10	0.2 (3)	C25—C24—C29—C28	0.8 (2)
C8—C9—C10—C11	−0.1 (4)	C23—C24—C29—C28	−179.83 (12)
C9—C10—C11—C12	−0.7 (3)	C4—C7—N1—C15	70.58 (13)
C9—C10—C11—C14	178.95 (18)	C4—C7—N1—C14	−167.90 (11)
C10—C11—C12—C13	1.3 (2)	C16—C15—N1—C7	−169.13 (10)
C14—C11—C12—C13	−178.29 (14)	C16—C15—N1—C14	69.34 (14)
C9—C8—C13—C12	0.4 (3)	C11—C14—N1—C7	66.68 (15)
C11—C12—C13—C8	−1.3 (3)	C11—C14—N1—C15	−172.91 (11)
C10—C11—C14—N1	64.75 (19)	N3—C16—N2—C18	−0.32 (13)
C12—C11—C14—N1	−115.64 (15)	C15—C16—N2—C18	−174.81 (10)
N1—C15—C16—N2	−121.66 (12)	C17—C18—N2—C16	1.09 (13)
N1—C15—C16—N3	64.40 (15)	C19—C18—N2—C16	−176.82 (12)
N3—C17—C18—N2	−1.42 (13)	N2—C16—N3—C17	−0.56 (13)
C22—C17—C18—N2	179.73 (12)	C15—C16—N3—C17	173.96 (10)
N3—C17—C18—C19	176.75 (11)	N2—C16—N3—C23	−179.14 (10)
C22—C17—C18—C19	−2.10 (19)	C15—C16—N3—C23	−4.62 (17)
N2—C18—C19—C20	178.03 (13)	C22—C17—N3—C16	179.87 (14)
C17—C18—C19—C20	0.29 (19)	C18—C17—N3—C16	1.17 (12)
C18—C19—C20—C21	1.7 (2)	C22—C17—N3—C23	−1.5 (2)
C19—C20—C21—C22	−2.1 (3)	C18—C17—N3—C23	179.80 (10)
C20—C21—C22—C17	0.3 (2)	C24—C23—N3—C16	−107.46 (13)
N3—C17—C22—C21	−176.71 (14)	C24—C23—N3—C17	74.22 (15)
C18—C17—C22—C21	1.8 (2)

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆N₄
M_r	442.55
Crystal system, space group	Orthorhombic, Pbca
Temperature (K)	293
a, b, c (Å)	15.364 (1), 17.006 (1), 18.908 (1)
V (Å³)	4940.3 (4)
Z	8
Radiation type	Mo Kα
µ (mm⁻¹)	0.07
Crystal size (mm)	0.46 × 0.34 × 0.21

Data collection
Diffractometer	Bruker APEX CCD area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.971, 0.985
No. of measured, independent and observed [I > 2σ(I)] reflections	28803, 6054, 4045
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.668

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.040, 0.120, 1.01
No. of reflections	6054
No. of parameters	308
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: SMART (Bruker, 1997), SAINT (Bruker, 1999), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL-Plus (Sheldrick, 1990).

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4-[2-(Dibenzyl­amino­meth­yl)-1H-benz­imidazol-1-ylmeth­yl]benzonitrile

Supporting information

Key indicators

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4-[2-(Dibenzylaminomethyl)-1H-benzimidazol-1-ylmethyl]benzonitrile