1-Methyl-2-({[(1-methyl-1H-benzimid­azol-2-yl)meth­yl](phen­yl)amino}­meth­yl)1H-benzimidazol-3-ium picrate

Liu, B.; Kou, F.; Jia, F.; Yuan, J.; Wu, H.

doi:10.1107/S1600536811024275

organic compounds

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ISSN: 2056-9890

Volume 67| Part 7| July 2011| Page o1816

doi:10.1107/S1600536811024275

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1-Methyl-2-({[(1-methyl-1H-benzimidazol-2-yl)methyl](phenyl)amino}methyl)1H-benzimidazol-3-ium picrate

Bin Liu,^a Fan Kou,^a Fei Jia,^a Jingkui Yuan ^a and Huilu Wu ^a ^*

^aSchool of Chemical and Biological Engineering, Lanzhou Jiaotong University, Lanzhou 730070, People's Republic of China
^*Correspondence e-mail: wuhuilu@163.com

(Received 30 May 2011; accepted 21 June 2011; online 25 June 2011)

In the title molecular salt, C₂₄H₂₄N₅⁺·C₆H₂N₃O₇⁻, the dihedral angle between the benzimidazole rings of the cation is 5.041 (2)°. In the anion, the three nitro groups make dihedral angles of 2.468 (3), 12.795 (3) and 24.958 (4)° with respect to the central ring. In the crystal, weak aromatic π–π stacking [centroid–centroid distance = 3.599 (15) Å] consolidates the packing. In addition, an intramolecular N—H⋯N hydrogen bond is observed.

Related literature

For background to proton-transfer compounds, see: Aghabozorg et al. (2008 ) and to benzimidazoles, see: Ram et al. (1992 ). For the biological activivity of benzimidazoles, see: Baraldi et al. (2004 ); Göker et al. (2002 ); Jayasekera et al. (2005 ); Starčević et al. (2007 ).

Experimental

Crystal data

C₂₄H₂₄N₅⁺·C₆H₂N₃O₇⁻
M_r = 610.59
Triclinic, $[P \overline 1]$
a = 9.4233 (5) Å
b = 12.3523 (7) Å
c = 12.5772 (7) Å
α = 92.007 (1)°
β = 98.497 (1)°
γ = 103.685 (1)°
V = 1403.07 (13) Å³
Z = 2
Mo Kα radiation
μ = 0.11 mm⁻¹
T = 293 K
0.31 × 0.30 × 0.29 mm

Data collection

Bruker SMART APEX diffractometer
Absorption correction: multi-scan (SADABS; Sheldrick, 2001 ) T_min = 0.968, T_max = 0.970
11689 measured reflections
5217 independent reflections
3567 reflections with I > 2σ(I)
R_int = 0.025

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.221
S = 1.19
5217 reflections
411 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.60 e Å⁻³
Δρ_min = −0.50 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N3—H3N⋯N1	0.92	1.85	2.715 (8)	157

Data collection: SMART (Bruker, 2001 ); cell refinement: SAINT (Bruker, 2001); 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: SHELXTL.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811024275/lr2014sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811024275/lr2014Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536811024275/lr2014Isup3.cml

checkCIF report

Comment top

Bis-benzimidazoles are known to be strong chelating agents coordinating through both the C=N nitrogen atoms. In addition, bis-benzimidazoles have a polymer-forming characteristic as a typical multidentate ligand. Benzimidazole compounds are environmentally friendly compounds with two high active nitrogen atoms in 1, 3-sites (Ram et al., 1992). Benzimidazoles and their azino-fused cyclic derivatives have a wide range of well known biological activities such as anticancer (Baraldi et al., 2004), antimicrobial (Jayasekera et al., 2005), antifungal (Göker et al., 2002), antiviral (Starčević et al., 2007).

In this paper, the asymmetric unit of the title proton transfer compound consists of a bis(N-methylbenzimidazol-2-ylmethyl)aniline(MEBBA) cation interacting with a picrate anion. The proton of the picric acid is transfered to the N3 nitrogen atoms of the MEBBA(Fig. 1). The dihedral angle between the planes defined by N2—C7—N1 and N3—C10—N4 is 5.041 (2)°, which indicates that the two benzimidazole rings are almost coplanar.

The crystal structure is mainly stabilized by weak π–π interactions involving the benzimidazol rings with centroid-centroid distances, Cg1 ··· Cg 3ⁱ and Cg2 ···Cg4ⁱ of 3.5999 (15) and 4.017 (18) Å repectively [symmetry code: (i) 1-x,1-y,1-z. Cg1 centroid of the (N1,C1,C6,N2,C7) ring; Cg2 centroid of the (N3,C10,N4.C11,C16) ring; Cg3 centroid of the (C11-C16) ring; Cg4 centroid of the (C1-C6) ring ]. In addition an N3-H3N···N1 intramolecular hydrogen bond is observed.

Related literature top

For background to proton-transfer compounds, see: Aghabozorg et al. (2008) and to benzimidazoles, see: Ram et al. (1992). For the biological activivity of benzimidazoles, see: Baraldi et al. (2004); Göker et al. (2002); Jayasekera et al. (2005); Starčević et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2001); cell refinement: SAINT (Bruker, 2001); data reduction: SAINT (Bruker, 2001); 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: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound.Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A view of the crystal packing of the title compound. Intermolecular hydrogen bonds are shown as dashed lines.

1-Methyl-2-({[(1-methyl-1H-benzimidazol-2- yl)methyl](phenyl)amino}methyl)1H-benzimidazol-3-ium picrate top

Crystal data top

C₃₀H₂₆N₈O₇	Z = 2
M_r = 610.59	F(000) = 636
Triclinic, P1	D_x = 1.445 Mg m⁻³
a = 9.4233 (5) Å	Mo Kα radiation, λ = 0.71073 Å
b = 12.3523 (7) Å	Cell parameters from 5217 reflections
c = 12.5772 (7) Å	θ = 3.0–25.5°
α = 92.007 (1)°	µ = 0.11 mm⁻¹
β = 98.497 (1)°	T = 293 K
γ = 103.685 (1)°	Block, yellow
V = 1403.07 (13) Å³	0.31 × 0.30 × 0.29 mm

Data collection top

Bruker SMART APEX diffractometer	5217 independent reflections
Radiation source: fine-focus sealed tube	3567 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 25.5°, θ_min = 3.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	h = −11→11
T_min = 0.968, T_max = 0.970	k = −14→14
11689 measured reflections	l = −15→13

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)] = 0.062	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.221	w = 1/[σ²(F_o²) + (0.1022P)² + 0.6611P] where P = (F_o² + 2F_c²)/3
S = 1.19	(Δ/σ)_max < 0.001
5217 reflections	Δρ_max = 0.60 e Å⁻³
411 parameters	Δρ_min = −0.50 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.024 (4)

Crystal data top

C₃₀H₂₆N₈O₇	γ = 103.685 (1)°
M_r = 610.59	V = 1403.07 (13) Å³
Triclinic, P1	Z = 2
a = 9.4233 (5) Å	Mo Kα radiation
b = 12.3523 (7) Å	µ = 0.11 mm⁻¹
c = 12.5772 (7) Å	T = 293 K
α = 92.007 (1)°	0.31 × 0.30 × 0.29 mm
β = 98.497 (1)°

Data collection top

Bruker SMART APEX diffractometer	5217 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 2001)	3567 reflections with I > 2σ(I)
T_min = 0.968, T_max = 0.970	R_int = 0.025
11689 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	1 restraint
wR(F²) = 0.221	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	Δρ_max = 0.60 e Å⁻³
5217 reflections	Δρ_min = −0.50 e Å⁻³
411 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
O1	0.4994 (3)	−0.13472 (19)	0.29886 (19)	0.0706 (7)
O2	0.2431 (4)	−0.2821 (4)	0.2686 (4)	0.172 (2)
O3	0.0611 (3)	−0.2466 (3)	0.1765 (3)	0.1027 (10)
O4	0.1139 (3)	0.0278 (2)	−0.0786 (2)	0.0864 (8)
O5	0.3145 (3)	0.1577 (2)	−0.0626 (2)	0.0874 (9)
O6	0.7374 (3)	0.1381 (3)	0.1867 (3)	0.1111 (12)
O7	0.7036 (3)	0.0635 (3)	0.3324 (3)	0.1153 (13)
N1	0.5570 (3)	0.6424 (2)	0.67349 (18)	0.0486 (6)
N2	0.7671 (2)	0.7189 (2)	0.78335 (18)	0.0474 (6)
N3	0.3314 (3)	0.4630 (2)	0.59716 (19)	0.0518 (6)
N4	0.2023 (3)	0.2910 (2)	0.6013 (2)	0.0530 (6)
N5	0.4792 (3)	0.46665 (19)	0.81228 (19)	0.0481 (6)
N6	0.1909 (3)	−0.2216 (2)	0.2111 (3)	0.0674 (8)
N7	0.2401 (3)	0.0720 (2)	−0.0337 (2)	0.0610 (7)
N8	0.6589 (3)	0.0772 (2)	0.2407 (2)	0.0643 (7)
C1	0.6137 (3)	0.7487 (2)	0.6418 (2)	0.0465 (7)
C2	0.5602 (4)	0.8062 (3)	0.5586 (2)	0.0570 (8)
H2A	0.4724	0.7746	0.5123	0.068*
C3	0.6420 (4)	0.9119 (3)	0.5471 (3)	0.0650 (9)
H3A	0.6086	0.9527	0.4922	0.078*
C4	0.7734 (4)	0.9591 (3)	0.6158 (3)	0.0658 (9)
H4A	0.8254	1.0309	0.6056	0.079*
C5	0.8294 (4)	0.9035 (3)	0.6984 (3)	0.0593 (8)
H5A	0.9181	0.9353	0.7436	0.071*
C6	0.7461 (3)	0.7972 (2)	0.7104 (2)	0.0476 (7)
C7	0.6516 (3)	0.6286 (2)	0.7579 (2)	0.0467 (7)
C8	0.6330 (3)	0.5244 (3)	0.8170 (2)	0.0506 (7)
H8A	0.6844	0.4747	0.7862	0.061*
H8B	0.6782	0.5435	0.8918	0.061*
C9	0.4206 (3)	0.3610 (2)	0.7497 (2)	0.0542 (7)
H9A	0.3671	0.3075	0.7934	0.065*
H9B	0.5019	0.3328	0.7306	0.065*
C10	0.3194 (3)	0.3709 (2)	0.6493 (2)	0.0496 (7)
C11	0.1347 (3)	0.3364 (3)	0.5125 (2)	0.0532 (7)
C12	0.0087 (4)	0.2915 (3)	0.4368 (3)	0.0662 (9)
H12A	−0.0465	0.2185	0.4375	0.079*
C13	−0.0292 (4)	0.3618 (4)	0.3608 (3)	0.0736 (11)
H13A	−0.1131	0.3356	0.3090	0.088*
C14	0.0544 (4)	0.4711 (3)	0.3591 (3)	0.0696 (9)
H14A	0.0251	0.5157	0.3062	0.084*
C15	0.1784 (4)	0.5142 (3)	0.4334 (2)	0.0593 (8)
H15A	0.2341	0.5870	0.4321	0.071*
C16	0.2174 (3)	0.4447 (3)	0.5106 (2)	0.0506 (7)
C17	0.8923 (3)	0.7329 (3)	0.8698 (3)	0.0642 (9)
H17A	0.8817	0.6669	0.9089	0.096*
H17B	0.8956	0.7960	0.9178	0.096*
H17C	0.9823	0.7452	0.8399	0.096*
C18	0.1542 (4)	0.1791 (3)	0.6371 (3)	0.0715 (10)
H18A	0.2203	0.1705	0.7003	0.107*
H18B	0.1548	0.1247	0.5809	0.107*
H18C	0.0558	0.1685	0.6537	0.107*
C19	0.3877 (3)	0.5143 (2)	0.8665 (2)	0.0434 (6)
C20	0.4428 (3)	0.6143 (2)	0.9302 (2)	0.0495 (7)
H20A	0.5427	0.6500	0.9368	0.059*
C21	0.3521 (4)	0.6609 (3)	0.9831 (2)	0.0564 (8)
H21A	0.3918	0.7272	1.0260	0.068*
C22	0.2039 (4)	0.6114 (3)	0.9739 (3)	0.0590 (8)
H22A	0.1425	0.6441	1.0088	0.071*
C23	0.1481 (3)	0.5121 (3)	0.9119 (2)	0.0601 (8)
H23A	0.0478	0.4776	0.9052	0.072*
C24	0.2373 (3)	0.4627 (3)	0.8597 (2)	0.0530 (7)
H24A	0.1975	0.3947	0.8197	0.064*
C25	0.4378 (3)	−0.0849 (2)	0.2298 (2)	0.0489 (7)
C26	0.2853 (3)	−0.1251 (2)	0.1753 (2)	0.0482 (7)
C27	0.2223 (3)	−0.0748 (2)	0.0922 (2)	0.0504 (7)
H27A	0.1246	−0.1048	0.0603	0.060*
C28	0.3037 (3)	0.0202 (2)	0.0560 (2)	0.0498 (7)
C29	0.4476 (3)	0.0692 (2)	0.1063 (2)	0.0515 (7)
H29A	0.5011	0.1347	0.0827	0.062*
C30	0.5096 (3)	0.0199 (2)	0.1907 (2)	0.0483 (7)
H3N	0.398 (2)	0.5313 (13)	0.606 (2)	0.046 (8)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0762 (15)	0.0589 (14)	0.0696 (15)	0.0146 (12)	−0.0099 (12)	0.0146 (11)
O2	0.103 (3)	0.148 (4)	0.237 (5)	−0.016 (2)	−0.012 (3)	0.137 (4)
O3	0.0588 (17)	0.091 (2)	0.148 (3)	−0.0060 (15)	0.0184 (17)	0.032 (2)
O4	0.0647 (16)	0.102 (2)	0.0810 (18)	0.0148 (15)	−0.0184 (13)	0.0133 (15)
O5	0.0880 (19)	0.0789 (18)	0.0841 (18)	0.0042 (15)	−0.0026 (15)	0.0349 (15)
O6	0.0684 (18)	0.127 (3)	0.109 (2)	−0.0245 (18)	−0.0051 (16)	0.034 (2)
O7	0.089 (2)	0.126 (3)	0.090 (2)	−0.0287 (18)	−0.0357 (17)	0.0316 (19)
N1	0.0416 (12)	0.0545 (14)	0.0457 (13)	0.0069 (10)	0.0007 (10)	0.0083 (11)
N2	0.0387 (12)	0.0566 (14)	0.0438 (12)	0.0090 (11)	0.0010 (10)	0.0047 (11)
N3	0.0533 (14)	0.0481 (14)	0.0470 (13)	0.0038 (12)	0.0006 (11)	0.0011 (11)
N4	0.0505 (14)	0.0464 (14)	0.0586 (15)	0.0070 (11)	0.0069 (11)	−0.0036 (11)
N5	0.0462 (13)	0.0451 (13)	0.0483 (13)	0.0065 (10)	0.0004 (10)	0.0049 (10)
N6	0.0639 (19)	0.0519 (16)	0.083 (2)	0.0054 (14)	0.0122 (15)	0.0138 (14)
N7	0.0594 (17)	0.0658 (18)	0.0556 (15)	0.0177 (14)	−0.0016 (13)	0.0062 (13)
N8	0.0553 (16)	0.0602 (17)	0.0666 (18)	0.0007 (13)	−0.0038 (14)	0.0076 (14)
C1	0.0437 (15)	0.0498 (16)	0.0436 (14)	0.0078 (12)	0.0049 (12)	0.0041 (12)
C2	0.0579 (18)	0.0584 (19)	0.0509 (17)	0.0108 (15)	0.0004 (14)	0.0092 (14)
C3	0.076 (2)	0.062 (2)	0.0574 (19)	0.0149 (17)	0.0125 (16)	0.0160 (16)
C4	0.074 (2)	0.0530 (19)	0.065 (2)	0.0019 (16)	0.0152 (17)	0.0096 (16)
C5	0.0535 (18)	0.0581 (19)	0.0586 (18)	0.0002 (15)	0.0077 (14)	−0.0010 (15)
C6	0.0457 (15)	0.0509 (16)	0.0445 (15)	0.0085 (13)	0.0080 (12)	0.0009 (12)
C7	0.0410 (14)	0.0563 (17)	0.0422 (14)	0.0107 (13)	0.0059 (12)	0.0055 (12)
C8	0.0403 (15)	0.0588 (18)	0.0517 (16)	0.0119 (13)	0.0034 (12)	0.0088 (13)
C9	0.0579 (18)	0.0468 (16)	0.0562 (17)	0.0133 (14)	0.0033 (14)	0.0039 (13)
C10	0.0512 (16)	0.0458 (16)	0.0497 (16)	0.0097 (13)	0.0051 (13)	0.0010 (13)
C11	0.0478 (16)	0.0621 (19)	0.0482 (16)	0.0119 (14)	0.0077 (13)	−0.0079 (14)
C12	0.0513 (18)	0.072 (2)	0.068 (2)	0.0075 (16)	0.0015 (16)	−0.0176 (18)
C13	0.0528 (19)	0.104 (3)	0.056 (2)	0.016 (2)	−0.0061 (15)	−0.016 (2)
C14	0.063 (2)	0.091 (3)	0.0509 (18)	0.0170 (19)	0.0001 (15)	−0.0035 (17)
C15	0.0578 (18)	0.069 (2)	0.0472 (16)	0.0122 (16)	0.0023 (14)	0.0031 (15)
C16	0.0464 (15)	0.0592 (18)	0.0426 (15)	0.0085 (14)	0.0041 (12)	−0.0008 (13)
C17	0.0467 (17)	0.077 (2)	0.0596 (19)	0.0074 (16)	−0.0080 (14)	0.0044 (16)
C18	0.065 (2)	0.054 (2)	0.088 (3)	−0.0007 (16)	0.0122 (18)	0.0033 (18)
C19	0.0437 (14)	0.0461 (15)	0.0377 (13)	0.0076 (12)	0.0016 (11)	0.0093 (11)
C20	0.0467 (15)	0.0487 (16)	0.0499 (16)	0.0047 (13)	0.0078 (13)	0.0104 (13)
C21	0.066 (2)	0.0519 (17)	0.0505 (17)	0.0102 (15)	0.0121 (14)	0.0113 (14)
C22	0.0565 (18)	0.074 (2)	0.0513 (17)	0.0221 (16)	0.0133 (14)	0.0115 (16)
C23	0.0446 (16)	0.081 (2)	0.0498 (17)	0.0056 (16)	0.0070 (13)	0.0132 (16)
C24	0.0460 (16)	0.0573 (18)	0.0478 (16)	0.0000 (14)	0.0015 (13)	0.0084 (13)
C25	0.0546 (17)	0.0440 (15)	0.0469 (15)	0.0132 (13)	0.0029 (13)	0.0018 (12)
C26	0.0486 (16)	0.0398 (15)	0.0540 (16)	0.0061 (12)	0.0086 (13)	0.0040 (12)
C27	0.0421 (15)	0.0465 (16)	0.0571 (17)	0.0052 (12)	0.0022 (13)	−0.0050 (13)
C28	0.0486 (16)	0.0528 (17)	0.0463 (15)	0.0130 (13)	0.0006 (12)	0.0049 (13)
C29	0.0535 (17)	0.0479 (16)	0.0508 (16)	0.0087 (13)	0.0069 (13)	0.0049 (13)
C30	0.0422 (15)	0.0466 (16)	0.0519 (16)	0.0073 (12)	0.0008 (12)	0.0022 (13)

Geometric parameters (Å, º) top

O1—C25	1.236 (3)	C9—H9A	0.9700
O2—N6	1.196 (4)	C9—H9B	0.9700
O3—N6	1.198 (4)	C11—C16	1.383 (4)
O4—N7	1.227 (3)	C11—C12	1.393 (4)
O5—N7	1.222 (4)	C12—C13	1.378 (5)
O6—N8	1.223 (4)	C12—H12A	0.9300
O7—N8	1.199 (4)	C13—C14	1.395 (5)
N1—C7	1.326 (3)	C13—H13A	0.9300
N1—C1	1.391 (4)	C14—C15	1.368 (4)
N2—C7	1.353 (4)	C14—H14A	0.9300
N2—C6	1.384 (4)	C15—C16	1.385 (4)
N2—C17	1.455 (4)	C15—H15A	0.9300
N3—C10	1.322 (4)	C17—H17A	0.9600
N3—C16	1.383 (4)	C17—H17B	0.9600
N3—H3N	0.916 (10)	C17—H17C	0.9600
N4—C10	1.343 (4)	C18—H18A	0.9600
N4—C11	1.403 (4)	C18—H18B	0.9600
N4—C18	1.458 (4)	C18—H18C	0.9600
N5—C19	1.393 (4)	C19—C20	1.393 (4)
N5—C9	1.444 (4)	C19—C24	1.398 (4)
N5—C8	1.447 (4)	C20—C21	1.371 (4)
N6—C26	1.438 (4)	C20—H20A	0.9300
N7—C28	1.440 (4)	C21—C22	1.372 (4)
N8—C30	1.453 (4)	C21—H21A	0.9300
C1—C2	1.385 (4)	C22—C23	1.377 (5)
C1—C6	1.397 (4)	C22—H22A	0.9300
C2—C3	1.374 (5)	C23—C24	1.373 (5)
C2—H2A	0.9300	C23—H23A	0.9300
C3—C4	1.388 (5)	C24—H24A	0.9300
C3—H3A	0.9300	C25—C30	1.450 (4)
C4—C5	1.374 (5)	C25—C26	1.460 (4)
C4—H4A	0.9300	C26—C27	1.366 (4)
C5—C6	1.387 (4)	C27—C28	1.374 (4)
C5—H5A	0.9300	C27—H27A	0.9300
C7—C8	1.495 (4)	C28—C29	1.392 (4)
C8—H8A	0.9700	C29—C30	1.368 (4)
C8—H8B	0.9700	C29—H29A	0.9300
C9—C10	1.494 (4)

C7—N1—C1	106.1 (2)	C13—C12—H12A	122.0
C7—N2—C6	107.3 (2)	C11—C12—H12A	122.0
C7—N2—C17	127.3 (3)	C12—C13—C14	122.0 (3)
C6—N2—C17	125.4 (3)	C12—C13—H13A	119.0
C10—N3—C16	108.6 (3)	C14—C13—H13A	119.0
C10—N3—H3N	133.7 (18)	C15—C14—C13	121.5 (3)
C16—N3—H3N	117.7 (18)	C15—C14—H14A	119.2
C10—N4—C11	107.1 (2)	C13—C14—H14A	119.2
C10—N4—C18	125.8 (3)	C14—C15—C16	117.1 (3)
C11—N4—C18	127.1 (3)	C14—C15—H15A	121.5
C19—N5—C9	120.3 (2)	C16—C15—H15A	121.5
C19—N5—C8	119.8 (2)	C11—C16—N3	107.0 (3)
C9—N5—C8	119.9 (3)	C11—C16—C15	121.5 (3)
O2—N6—O3	119.6 (3)	N3—C16—C15	131.5 (3)
O2—N6—C26	120.2 (3)	N2—C17—H17A	109.5
O3—N6—C26	120.0 (3)	N2—C17—H17B	109.5
O5—N7—O4	122.7 (3)	H17A—C17—H17B	109.5
O5—N7—C28	118.7 (3)	N2—C17—H17C	109.5
O4—N7—C28	118.6 (3)	H17A—C17—H17C	109.5
O7—N8—O6	121.3 (3)	H17B—C17—H17C	109.5
O7—N8—C30	120.3 (3)	N4—C18—H18A	109.5
O6—N8—C30	118.4 (3)	N4—C18—H18B	109.5
C2—C1—N1	130.7 (3)	H18A—C18—H18B	109.5
C2—C1—C6	120.7 (3)	N4—C18—H18C	109.5
N1—C1—C6	108.6 (2)	H18A—C18—H18C	109.5
C3—C2—C1	117.4 (3)	H18B—C18—H18C	109.5
C3—C2—H2A	121.3	N5—C19—C20	121.3 (2)
C1—C2—H2A	121.3	N5—C19—C24	121.1 (3)
C2—C3—C4	121.4 (3)	C20—C19—C24	117.6 (3)
C2—C3—H3A	119.3	C21—C20—C19	121.1 (3)
C4—C3—H3A	119.3	C21—C20—H20A	119.5
C5—C4—C3	122.4 (3)	C19—C20—H20A	119.5
C5—C4—H4A	118.8	C20—C21—C22	121.1 (3)
C3—C4—H4A	118.8	C20—C21—H21A	119.5
C4—C5—C6	116.2 (3)	C22—C21—H21A	119.5
C4—C5—H5A	121.9	C21—C22—C23	118.5 (3)
C6—C5—H5A	121.9	C21—C22—H22A	120.7
N2—C6—C5	132.0 (3)	C23—C22—H22A	120.7
N2—C6—C1	106.0 (2)	C24—C23—C22	121.5 (3)
C5—C6—C1	122.0 (3)	C24—C23—H23A	119.3
N1—C7—N2	112.1 (2)	C22—C23—H23A	119.3
N1—C7—C8	123.7 (3)	C23—C24—C19	120.3 (3)
N2—C7—C8	124.2 (2)	C23—C24—H24A	119.9
N5—C8—C7	112.6 (2)	C19—C24—H24A	119.9
N5—C8—H8A	109.1	O1—C25—C30	124.1 (3)
C7—C8—H8A	109.1	O1—C25—C26	124.5 (3)
N5—C8—H8B	109.1	C30—C25—C26	111.4 (2)
C7—C8—H8B	109.1	C27—C26—N6	116.3 (3)
H8A—C8—H8B	107.8	C27—C26—C25	124.1 (3)
N5—C9—C10	112.1 (2)	N6—C26—C25	119.6 (3)
N5—C9—H9A	109.2	C26—C27—C28	119.8 (3)
C10—C9—H9A	109.2	C26—C27—H27A	120.1
N5—C9—H9B	109.2	C28—C27—H27A	120.1
C10—C9—H9B	109.2	C27—C28—C29	120.8 (3)
H9A—C9—H9B	107.9	C27—C28—N7	120.4 (3)
N3—C10—N4	110.6 (3)	C29—C28—N7	118.8 (3)
N3—C10—C9	123.7 (3)	C30—C29—C28	119.3 (3)
N4—C10—C9	125.7 (3)	C30—C29—H29A	120.4
C16—C11—C12	121.9 (3)	C28—C29—H29A	120.4
C16—C11—N4	106.7 (2)	C29—C30—C25	124.3 (3)
C12—C11—N4	131.4 (3)	C29—C30—N8	116.1 (3)
C13—C12—C11	116.0 (3)	C25—C30—N8	119.5 (2)

C7—N1—C1—C2	−179.9 (3)	N4—C11—C16—N3	−0.3 (3)
C7—N1—C1—C6	0.3 (3)	C12—C11—C16—C15	0.3 (5)
N1—C1—C2—C3	180.0 (3)	N4—C11—C16—C15	−178.7 (3)
C6—C1—C2—C3	−0.3 (5)	C10—N3—C16—C11	0.0 (3)
C1—C2—C3—C4	0.3 (5)	C10—N3—C16—C15	178.2 (3)
C2—C3—C4—C5	0.2 (6)	C14—C15—C16—C11	0.1 (5)
C3—C4—C5—C6	−0.7 (5)	C14—C15—C16—N3	−177.9 (3)
C7—N2—C6—C5	−179.6 (3)	C9—N5—C19—C20	177.9 (2)
C17—N2—C6—C5	−0.2 (5)	C8—N5—C19—C20	−3.3 (4)
C7—N2—C6—C1	0.1 (3)	C9—N5—C19—C24	−1.5 (4)
C17—N2—C6—C1	179.4 (3)	C8—N5—C19—C24	177.3 (2)
C4—C5—C6—N2	−179.6 (3)	N5—C19—C20—C21	179.8 (3)
C4—C5—C6—C1	0.8 (5)	C24—C19—C20—C21	−0.8 (4)
C2—C1—C6—N2	180.0 (3)	C19—C20—C21—C22	−0.9 (4)
N1—C1—C6—N2	−0.2 (3)	C20—C21—C22—C23	1.3 (4)
C2—C1—C6—C5	−0.3 (5)	C21—C22—C23—C24	−0.1 (5)
N1—C1—C6—C5	179.5 (3)	C22—C23—C24—C19	−1.6 (4)
C1—N1—C7—N2	−0.2 (3)	N5—C19—C24—C23	−178.6 (3)
C1—N1—C7—C8	−179.6 (3)	C20—C19—C24—C23	2.0 (4)
C6—N2—C7—N1	0.1 (3)	O2—N6—C26—C27	166.1 (4)
C17—N2—C7—N1	−179.2 (3)	O3—N6—C26—C27	−8.0 (5)
C6—N2—C7—C8	179.5 (3)	O2—N6—C26—C25	−15.6 (6)
C17—N2—C7—C8	0.1 (5)	O3—N6—C26—C25	170.3 (3)
C19—N5—C8—C7	−68.7 (3)	O1—C25—C26—C27	−173.8 (3)
C9—N5—C8—C7	110.1 (3)	C30—C25—C26—C27	4.8 (4)
N1—C7—C8—N5	−29.1 (4)	O1—C25—C26—N6	8.0 (5)
N2—C7—C8—N5	151.6 (3)	C30—C25—C26—N6	−173.4 (3)
C19—N5—C9—C10	70.9 (3)	N6—C26—C27—C28	177.7 (3)
C8—N5—C9—C10	−107.9 (3)	C25—C26—C27—C28	−0.6 (5)
C16—N3—C10—N4	0.3 (3)	C26—C27—C28—C29	−3.1 (5)
C16—N3—C10—C9	−177.8 (3)	C26—C27—C28—N7	178.0 (3)
C11—N4—C10—N3	−0.4 (3)	O5—N7—C28—C27	178.6 (3)
C18—N4—C10—N3	−179.3 (3)	O4—N7—C28—C27	−2.1 (5)
C11—N4—C10—C9	177.6 (3)	O5—N7—C28—C29	−0.3 (4)
C18—N4—C10—C9	−1.3 (5)	O4—N7—C28—C29	179.1 (3)
N5—C9—C10—N3	29.2 (4)	C27—C28—C29—C30	1.9 (5)
N5—C9—C10—N4	−148.6 (3)	N7—C28—C29—C30	−179.2 (3)
C10—N4—C11—C16	0.4 (3)	C28—C29—C30—C25	3.1 (5)
C18—N4—C11—C16	179.3 (3)	C28—C29—C30—N8	−178.6 (3)
C10—N4—C11—C12	−178.4 (3)	O1—C25—C30—C29	172.5 (3)
C18—N4—C11—C12	0.4 (5)	C26—C25—C30—C29	−6.1 (4)
C16—C11—C12—C13	−0.6 (5)	O1—C25—C30—N8	−5.7 (5)
N4—C11—C12—C13	178.1 (3)	C26—C25—C30—N8	175.7 (3)
C11—C12—C13—C14	0.6 (5)	O7—N8—C30—C29	155.6 (4)
C12—C13—C14—C15	−0.2 (6)	O6—N8—C30—C29	−25.2 (5)
C13—C14—C15—C16	−0.1 (5)	O7—N8—C30—C25	−26.1 (5)
C12—C11—C16—N3	178.7 (3)	O6—N8—C30—C25	153.1 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N3—H3N···N1	0.92	1.85	2.715 (8)	157

Experimental details

Crystal data
Chemical formula	C₃₀H₂₆N₈O₇
M_r	610.59
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.4233 (5), 12.3523 (7), 12.5772 (7)
α, β, γ (°)	92.007 (1), 98.497 (1), 103.685 (1)
V (Å³)	1403.07 (13)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.11
Crystal size (mm)	0.31 × 0.30 × 0.29

Data collection
Diffractometer	Bruker SMART APEX diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 2001)
T_min, T_max	0.968, 0.970
No. of measured, independent and observed [I > 2σ(I)] reflections	11689, 5217, 3567
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.221, 1.19
No. of reflections	5217
No. of parameters	411
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.60, −0.50

Computer programs: SMART (Bruker, 2001), SAINT (Bruker, 2001), 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
N3—H3N···N1	0.916	1.848	2.715 (8)	157

Acknowledgements

The authors acknowledge the financial support and grants from the `Qing Lan' Talent Engineering Funds and Students' Science and Technology Innovation Funds (grant No. DXS2010–040) of Lanzhou Jiaotong University. A grant from the Middle-Young Age Science Foundation (grant No. 3YS061-A25–023) and the Long Yuan `Qing Nian' of Gansu Province is also acknowledged.

References

Aghabozorg, H., Manteghi, F. & Sheshmani, S. (2008). J. Iran. Chem. Soc. 5, 184–227. CrossRef CAS Google Scholar
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Bruker (2001). SAINT and SMART. Bruker AXS Inc., Madison, Wisconsin, USA. Google Scholar
Göker, H., Kus, C., Boykin, D. W., Yildiz, S. & Altanlar, N. (2002). Bioorg. Med. Chem. 10, 2589–2596. Web of Science PubMed Google Scholar
Jayasekera, M. M. K., Onheiber, K., Keith, J., Venkatesan, H., Santillan, A., Stocking, E. M., Tang, L., Miller, J., Gomez, L., Rhead, B., Delcamp, T., Huang, S., Wolin, R., Bobkova, E. & Shaw, K. J. (2005). Antimicrob. Agents Chemother. 49, 131–136. Web of Science CrossRef PubMed CAS Google Scholar
Ram, S., Wise, D. S., Wotring, L. L., McCall, J. W. & Townsend, L. B. (1992). J. Med. Chem. 35, 539–547 CrossRef PubMed CAS Web of Science Google Scholar
Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
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Volume 67| Part 7| July 2011| Page o1816

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

1-Methyl-2-({[(1-methyl-1H-benzimid­azol-2-yl)meth­yl](phen­yl)amino}­meth­yl)1H-benzimidazol-3-ium picrate

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

1-Methyl-2-({[(1-methyl-1H-benzimidazol-2-yl)methyl](phenyl)amino}methyl)1H-benzimidazol-3-ium picrate