Literature DB >> 30319814

Crystal structure and Hirshfeld surface analysis and of 2-ammoniumylmeth-yl-1H-benzimidazol-3-ium chloride monohydrate.

Pinar Sen1, Sevgi Kansiz2, Necmi Dege2, S Zeki Yildiz3, Galyna G Tsapyuk4.   

Abstract

The asymmetric unit of the title compound, C8H11N3 2+·2Cl-·H2O, contains three organic cations, six chloride anions and three water mol-ecules of crystallization, which are connected by extensive hydrogen-bonding inter-actions into a three-dimensional supra-molecular architecture. Hirshfeld surface analysis and two-dimensional fingerprint plots indicate that the most important contributions to the crystal packing are from H⋯H (37.4%), Cl⋯H/H⋯Cl (35.5%), C⋯H/H⋯C (9.5%) and C⋯C (6.9%) inter-actions.

Entities:  

Keywords:  Hirshfeld surface; crystal structure; ethanaminium; ethanaminium chloride; imidazol

Year:  2018        PMID： 30319814      PMCID： PMC6176449          DOI： 10.1107/S205698901801335X

Source DB:  PubMed          Journal:  Acta Crystallogr E Crystallogr Commun


Chemical context

Heterocyclic compounds containing nitro­gen such as benzimidazoles and their derivatives have attracted attention because of their medicinal applications as anti­ulcer, anti­cancer, anti­fungal, anti­mycobacterial and anti-inflammatory agents (El-masry et al., 2000 ▸). Besides being important pharma­cophores, in particular amine-substituted benzimidazoles are good inter­mediates for the synthesis of different organic compounds (Maurya et al., 2007 ▸). General methods for the preparation of benzimidazoles involve the reaction of o-phenyl­enedi­amine and carb­oxy­lic acid or its derivatives under harsh dehydrating conditions or with aldehydes followed by oxidation (Peng et al., 2014 ▸). We report herein the compound 2-amino­methyl­benzimidazole di­hydro­chloride (ambmz·2HCl) prepared as described previously (Wu et al., 2008 ▸)

Structural commentary

The asymmetric unit of the title compound contains three organic cations, six chloride anions and three water mol­ecules of crystallization, which are connected by O—H⋯Cl, N—H⋯O and N—H⋯Cl hydrogen bonds (Fig. 1 ▸). The r.m.s. deviations of the benzimidazolium ring systems are 0.0085 Å for N1/N2/C1–C7, 0.0076 Å for N4/N5/C9–C15, 0.0063 Å for N7/N8/C17–C23 with maximum deviations from planarity of 0.0169 (13) Å for atom C7, 0.0149 (13) Å for atom C15 and 0.0132 (13) Å for atom C23, respectively. The observed bond lengths are in good agreement with previously reported values (Cui, 2011 ▸).
Figure 1

The mol­ecular structure of the title compound, showing the atom labelling. Displacement ellipsoids are drawn at the 20% probability level.

Supra­molecular features

The crystal packing of the title compound features extensive hydrogen bonding (Table 1 ▸ and Fig. and 2) involving all three O atoms and all nine N atoms. N5—H5A⋯Cl5, N8—H8⋯Cl4, N2—H2⋯Cl1ii, N9—H9C⋯Cl5vi and N6—H6B⋯Cl1v hydrogen bonds link the ions into chains along the c-axis direction. These chains are linked by O–H⋯Cl and N—H⋯O hydrogen bonds, generating a three-dimensional network (Fig. 2 ▸).
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
O1—H1A⋯Cl4i 0.82 (2)2.63 (2)3.4431 (15)168 (3)
O1—H2B⋯Cl20.81 (2)2.36 (2)3.1598 (18)169 (3)
O2—H2C⋯Cl30.82 (2)2.33 (2)3.1244 (17)165 (2)
O2—H2D⋯Cl10.81 (1)2.64 (1)3.4492 (15)171 (3)
O3—H3D⋯Cl5ii 0.80 (2)2.69 (2)3.4586 (15)164 (3)
O3—H3E⋯Cl6ii 0.82 (2)2.32 (2)3.1364 (18)173 (3)
N1—H1⋯O10.83 (2)1.92 (2)2.746 (2)174 (2)
N2—H2⋯Cl1iii 0.71 (2)2.44 (2)3.1519 (17)175 (2)
N3—H3⋯Cl30.88 (3)2.30 (3)3.105 (2)153 (2)
N3—H3A⋯Cl10.86 (4)2.26 (3)3.119 (2)173 (3)
N3—H3B⋯Cl4iv 0.99 (3)2.33 (2)3.267 (2)156.8 (19)
N4—H4A⋯O20.85 (2)1.91 (2)2.754 (2)171 (2)
N5—H5A⋯Cl50.83 (2)2.31 (2)3.1205 (17)165 (2)
N6—H6A⋯Cl20.87 (3)2.33 (3)3.107 (2)150 (2)
N6—H6B⋯Cl1v 0.98 (3)2.36 (2)3.287 (2)158.2 (18)
N6—H6C⋯Cl4i 0.79 (3)2.35 (4)3.1347 (19)176 (3)
N7—H7⋯O30.85 (3)1.89 (3)2.742 (2)175 (3)
N8—H8⋯Cl40.81 (2)2.31 (2)3.1049 (17)172 (2)
N9—H9A⋯Cl60.83 (3)2.35 (3)3.100 (2)151 (2)
N9—H9B⋯Cl50.80 (3)2.32 (2)3.120 (2)176 (2)
N9—H9C⋯Cl5vi 0.99 (3)2.34 (3)3.270 (2)157 (2)
C4—H4⋯Cl1i 0.92 (2)2.81 (2)3.535 (2)136.7 (16)
C8—H8B⋯Cl3vii 0.93 (3)2.65 (3)3.544 (2)162 (2)

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) ; (vi) ; (vii) .

Figure 2

The view of the crystal packing of the title compound. Dashed lines denote the hydrogen bonds.

Hirshfeld surface analysis

The Hirshfeld surface analysis was performed using Crystal Explorer (Turner et al., 2017 ▸). The Hirshfeld surfaces, illus­trated in Fig. 3 ▸, and their associated two-dimensional fingerprint plots were used to qu­antify the various inter­molecular inter­actions in the synthesized complex. Red spots on the Hirshfeld surfaces indicate the inter­molecular contacts involved in strong hydrogen bonds and inter­atomic contacts (Gümüş et al., 2018 ▸; Kansız et al., 2018 ▸; Kansız & Dege, 2018 ▸). The red spots in Fig. 4 ▸ correspond to the H⋯Cl contacts resulting from the N—H⋯Cl and O—H⋯Cl hydrogen bonds. The Hirshfeld surfaces were mapped using a standard (high) surface resolution with the three-dimensional d surfaces mapped over a fixed colour scale of −0.518 (red) to 1.174 (blue) a.u..
Figure 3

The Hirshfeld surface of the title compound mapped over d norm, d i and d e.

Figure 4

Hirshfeld surface mapped over d norm to visualize the inter­molecular inter­actions of the title compound.

Fig. 5 ▸ shows the two-dimensional fingerprint plot of all the contacts contributing to the Hirshfeld surface represented in normal mode. Fig. 6 ▸ shows the two-dimensional fingerprint plots of the (d i, d e) points associated with various atoms. H⋯H contacts contribute 37.4% to the Hirshfeld surface. The graph for Cl⋯H/H⋯Cl shows the contacts between the chlorine atoms inside the Hirshfeld surface and the hydrogen atoms outside the surface and vice versa, and has two symmetrical wings on the left and right sides (35.5%). Further, there are C⋯H/H⋯C (9.5%), C⋯C (6.9%), O⋯H/H⋯O (4.1%) and N⋯H/H⋯N (3.4%) contacts.
Figure 5

Fingerprint plot of all the contacts.

Figure 6

Two-dimensional fingerprint plots with a d norm view of the H⋯H (37.4%), Cl⋯H/H⋯Cl (35.5%), C⋯H/H⋯C (9.5%) and C⋯C (6.9%) contacts in the title compound.

Synthesis and crystallization

o-Phenyl­enedi­amine (10.8 g, 99.87 mmol) and glycine (10.00 g, 133.2 mmol) were dissolved in 5.5 M HCl (150 mL) . The reaction mixture was purged by argon at room temperature and heated up to reflux temperature for 12 h. The reaction was monitored by TLC. After completion of the reaction, the mixture was concentrated to 50 mL and kept at 269 K for 2 d. The crystals were filtered off and washed twice with acetone and dried to give the desired product (Fig. 7 ▸).
Figure 7

The synthesis of the title compound.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2 ▸. C-bound H atoms were positioned geometrically with C—H distances of 0.93–0.97 Å. and refined as riding, with U iso(H) = 1.2U eq(C). N-bound H atoms were located in difference-Fourier maps and refined isotropically. The coordinates of the water H atoms were determined from a difference-Fourier map and refined isotropically subject to a restraint of O—H = 0.82 (4) Å.
Table 2

Experimental details

Crystal data
Chemical formulaC8H11N3 +·2Cl−·H2O·
M r 238.11
Crystal system, space groupTriclinic, P
Temperature (K)296
a, b, c (Å)6.9340 (4), 12.1198 (7), 19.2128 (11)
α, β, γ (°)99.859 (5), 90.647 (5), 90.247 (5)
V (Å3)1590.64 (16)
Z 6
Radiation typeMo Kα
μ (mm−1)0.58
Crystal size (mm)0.57 × 0.50 × 0.46
 
Data collection
DiffractometerStoe IPDS 2
Absorption correctionIntegration (X-RED32; Stoe & Cie, 2002 ▸)
T min, T max 0.788, 0.828
No. of measured, independent and observed [I > 2σ(I)] reflections16045, 6254, 5000
R int 0.064
(sin θ/λ)max (Å−1)0.617
 
Refinement
R[F 2 > 2σ(F 2)], wR(F 2), S 0.035, 0.092, 0.96
No. of reflections6254
No. of parameters536
No. of restraints9
H-atom treatmentAll H-atom parameters refined
Δρmax, Δρmin (e Å−3)0.34, −0.28

Computer programs: X-AREA and X-RED32 (Stoe & Cie, 2002 ▸), SHELXL2017/1 (Sheldrick, 2015 ▸), ORTEP-3 for Windows and WinGX (Farrugia, 2012 ▸) and PLATON (Spek, 2009 ▸).

Crystal structure: contains datablock(s) I. DOI: 10.1107/S205698901801335X/xu5941sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S205698901801335X/xu5941Isup2.hkl Click here for additional data file. Supporting information file. DOI: 10.1107/S205698901801335X/xu5941Isup3.cml CCDC reference: 1868580 Additional supporting information: crystallographic information; 3D view; checkCIF report
C8H11N3+·2Cl−·H2O·Z = 6
Mr = 238.11F(000) = 744
Triclinic, P1Dx = 1.491 Mg m−3
a = 6.9340 (4) ÅMo Kα radiation, λ = 0.71073 Å
b = 12.1198 (7) ÅCell parameters from 18110 reflections
c = 19.2128 (11) Åθ = 1.7–27.4°
α = 99.859 (5)°µ = 0.58 mm−1
β = 90.647 (5)°T = 296 K
γ = 90.247 (5)°Prism, brown
V = 1590.64 (16) Å30.57 × 0.50 × 0.46 mm
Stoe IPDS 2 diffractometer6254 independent reflections
Radiation source: sealed X-ray tube, 12 x 0.4 mm long-fine focus5000 reflections with I > 2σ(I)
Detector resolution: 6.67 pixels mm-1Rint = 0.064
rotation method scansθmax = 26.0°, θmin = 1.7°
Absorption correction: integration (X-RED32; Stoe & Cie, 2002)h = −8→8
Tmin = 0.788, Tmax = 0.828k = −14→14
16045 measured reflectionsl = −23→23
Refinement on F2Hydrogen site location: difference Fourier map
Least-squares matrix: fullAll H-atom parameters refined
R[F2 > 2σ(F2)] = 0.035w = 1/[σ2(Fo2) + (0.056P)2] where P = (Fo2 + 2Fc2)/3
wR(F2) = 0.092(Δ/σ)max = 0.001
S = 0.96Δρmax = 0.34 e Å−3
6254 reflectionsΔρmin = −0.28 e Å−3
536 parametersExtinction correction: SHELXL-2017/1 (Sheldrick 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
9 restraintsExtinction coefficient: 0.0327 (17)
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.
xyzUiso*/Ueq
Cl11.44783 (7)0.25544 (4)0.93231 (2)0.04012 (12)
Cl40.55220 (7)0.93572 (4)0.73215 (2)0.03912 (12)
Cl50.44034 (7)0.39635 (4)0.59956 (2)0.04089 (13)
Cl30.85067 (7)0.04098 (4)0.91238 (3)0.04840 (14)
Cl6−0.13546 (8)0.60301 (5)0.58937 (3)0.05432 (15)
Cl21.13465 (8)0.15568 (5)0.74387 (3)0.05337 (15)
O20.9557 (2)0.29533 (13)0.93050 (9)0.0492 (3)
O11.0439 (2)−0.10288 (14)0.73035 (9)0.0517 (4)
N40.7622 (2)0.41261 (12)0.84094 (8)0.0332 (3)
O30.0525 (2)0.64579 (14)0.39493 (9)0.0553 (4)
N70.2335 (2)0.81071 (13)0.48888 (8)0.0333 (3)
N50.6592 (2)0.46067 (13)0.74372 (9)0.0347 (3)
N11.2273 (2)−0.21584 (13)0.82407 (8)0.0334 (3)
N21.3362 (2)−0.25722 (14)0.92226 (9)0.0376 (4)
N80.3400 (2)0.90994 (13)0.58704 (9)0.0358 (3)
N60.7067 (3)0.17781 (15)0.79023 (10)0.0427 (4)
N90.2868 (3)0.60170 (15)0.53791 (10)0.0447 (4)
N31.2803 (3)0.02017 (15)0.86850 (10)0.0421 (4)
C140.7037 (2)0.55975 (14)0.78881 (9)0.0314 (4)
C220.2942 (2)0.98527 (15)0.54300 (9)0.0323 (4)
C90.7708 (2)0.52904 (14)0.85148 (9)0.0315 (4)
C150.6935 (2)0.37525 (15)0.77671 (9)0.0335 (4)
C11.2214 (2)−0.33227 (14)0.81587 (9)0.0324 (4)
C170.2255 (2)0.92225 (14)0.48021 (9)0.0319 (4)
C100.8268 (3)0.60738 (16)0.90934 (10)0.0369 (4)
C180.1652 (2)0.97150 (16)0.42385 (10)0.0355 (4)
C71.2981 (2)−0.17423 (15)0.88773 (9)0.0339 (4)
C21.1642 (3)−0.41361 (16)0.75996 (10)0.0377 (4)
C61.2930 (2)−0.35839 (15)0.87927 (10)0.0349 (4)
C130.6926 (3)0.67112 (16)0.78093 (11)0.0385 (4)
C230.3047 (2)0.80652 (15)0.55283 (9)0.0342 (4)
C200.2469 (3)1.15029 (16)0.49646 (11)0.0392 (4)
C210.3055 (3)1.10154 (16)0.55279 (11)0.0382 (4)
C120.7490 (3)0.74911 (16)0.83844 (11)0.0394 (4)
C51.3092 (3)−0.46915 (17)0.88878 (11)0.0421 (4)
C190.1785 (3)1.08684 (16)0.43313 (10)0.0389 (4)
C41.2532 (3)−0.54982 (17)0.83351 (12)0.0443 (5)
C110.8145 (3)0.71817 (16)0.90146 (11)0.0401 (4)
C81.3424 (3)−0.05475 (17)0.91637 (11)0.0414 (4)
C160.6469 (3)0.25681 (17)0.74466 (11)0.0428 (4)
C31.1819 (3)−0.52313 (17)0.77020 (12)0.0423 (4)
C240.3525 (3)0.70519 (18)0.58323 (12)0.0458 (5)
H21.384 (3)−0.2526 (17)0.9558 (11)0.028 (5)*
H180.111 (3)0.9325 (18)0.3840 (12)0.044 (6)*
H100.873 (3)0.5879 (16)0.9522 (11)0.033 (5)*
H2A1.108 (3)−0.3947 (17)0.7161 (11)0.039 (5)*
H110.854 (3)0.7742 (19)0.9433 (11)0.046 (6)*
H190.136 (3)1.1218 (17)0.3927 (11)0.039 (5)*
H200.255 (3)1.223 (2)0.5012 (12)0.048 (6)*
H130.649 (3)0.6891 (17)0.7361 (11)0.039 (5)*
H120.740 (3)0.816 (2)0.8342 (12)0.050 (6)*
H210.350 (3)1.1439 (19)0.5987 (12)0.047 (6)*
H51.355 (3)−0.4842 (19)0.9333 (12)0.050 (6)*
H41.264 (3)−0.6238 (19)0.8385 (11)0.040 (5)*
H5A0.608 (3)0.4556 (18)0.7041 (12)0.041 (6)*
H11.179 (3)−0.179 (2)0.7956 (13)0.055 (7)*
H4A0.811 (3)0.372 (2)0.8683 (12)0.052 (6)*
H80.393 (3)0.9236 (17)0.6251 (12)0.036 (5)*
H24A0.291 (3)0.710 (2)0.6289 (13)0.058 (7)*
H24B0.491 (5)0.697 (3)0.5884 (17)0.101 (10)*
H70.183 (4)0.757 (2)0.4601 (14)0.063 (7)*
H9A0.167 (4)0.600 (2)0.5354 (13)0.058 (7)*
H16A0.518 (4)0.253 (2)0.7334 (15)0.076 (8)*
H9B0.325 (4)0.551 (2)0.5559 (13)0.055 (7)*
H9C0.336 (4)0.593 (2)0.4891 (16)0.080 (9)*
H16B0.709 (3)0.2385 (19)0.7019 (13)0.052 (6)*
H3C1.143 (3)−0.581 (2)0.7340 (12)0.050 (6)*
H8A1.472 (4)−0.045 (2)0.9269 (13)0.061 (7)*
H8B1.282 (4)−0.035 (2)0.9596 (14)0.066 (7)*
H6A0.831 (4)0.176 (2)0.7947 (13)0.061 (8)*
H6B0.660 (3)0.194 (2)0.8388 (14)0.059 (7)*
H6C0.667 (4)0.118 (3)0.7738 (15)0.065 (8)*
H2C0.920 (3)0.2322 (16)0.9337 (14)0.063 (8)*
H2D1.072 (2)0.289 (2)0.9267 (17)0.098 (12)*
H3A1.316 (4)0.087 (3)0.8871 (16)0.086 (10)*
H3B1.330 (3)0.000 (2)0.8197 (14)0.060 (7)*
H31.154 (4)0.022 (2)0.8652 (12)0.056 (7)*
H3D−0.062 (3)0.649 (3)0.3941 (19)0.106 (12)*
H3E0.082 (4)0.5804 (16)0.3962 (15)0.071 (9)*
H1A0.926 (3)−0.102 (3)0.7339 (18)0.100 (12)*
H2B1.076 (4)−0.0391 (16)0.7286 (15)0.069 (9)*
U11U22U33U12U13U23
Cl10.0439 (2)0.0399 (2)0.0360 (2)0.00037 (18)−0.00373 (18)0.00530 (18)
Cl40.0430 (2)0.0388 (2)0.0348 (2)−0.00156 (18)−0.00346 (18)0.00436 (18)
Cl50.0447 (3)0.0395 (2)0.0378 (2)−0.00330 (18)−0.00542 (18)0.00547 (18)
Cl30.0486 (3)0.0458 (3)0.0518 (3)−0.0026 (2)0.0038 (2)0.0112 (2)
Cl60.0503 (3)0.0508 (3)0.0615 (3)0.0005 (2)−0.0013 (2)0.0085 (2)
Cl20.0491 (3)0.0519 (3)0.0600 (3)−0.0049 (2)−0.0007 (2)0.0126 (2)
O20.0490 (9)0.0458 (9)0.0538 (9)−0.0016 (7)−0.0076 (7)0.0121 (7)
O10.0475 (9)0.0546 (9)0.0566 (9)−0.0045 (7)−0.0098 (7)0.0209 (8)
N40.0346 (7)0.0320 (7)0.0337 (8)0.0003 (6)−0.0023 (6)0.0071 (6)
O30.0496 (9)0.0456 (9)0.0652 (10)0.0011 (7)−0.0110 (8)−0.0056 (7)
N70.0323 (7)0.0331 (8)0.0331 (8)−0.0025 (6)−0.0008 (6)0.0017 (6)
N50.0336 (8)0.0387 (8)0.0314 (8)0.0013 (6)−0.0032 (6)0.0047 (6)
N10.0317 (7)0.0359 (8)0.0341 (8)−0.0008 (6)−0.0022 (6)0.0106 (6)
N20.0333 (8)0.0494 (10)0.0314 (9)−0.0017 (7)−0.0053 (7)0.0107 (7)
N80.0342 (8)0.0420 (9)0.0298 (8)−0.0059 (6)−0.0038 (6)0.0028 (6)
N60.0505 (11)0.0310 (9)0.0451 (10)−0.0057 (8)0.0012 (8)0.0025 (7)
N90.0501 (11)0.0375 (9)0.0485 (11)0.0051 (8)0.0010 (8)0.0128 (8)
N30.0469 (10)0.0358 (9)0.0426 (10)−0.0042 (7)0.0018 (8)0.0034 (7)
C140.0264 (8)0.0346 (9)0.0331 (9)0.0007 (6)0.0018 (7)0.0052 (7)
C220.0265 (8)0.0378 (9)0.0315 (9)−0.0035 (7)0.0011 (7)0.0027 (7)
C90.0275 (8)0.0312 (8)0.0357 (9)−0.0003 (6)0.0023 (7)0.0054 (7)
C150.0295 (8)0.0347 (9)0.0353 (9)0.0001 (7)0.0003 (7)0.0029 (7)
C10.0266 (8)0.0355 (9)0.0361 (9)−0.0010 (7)0.0026 (7)0.0093 (7)
C170.0274 (8)0.0337 (9)0.0334 (9)−0.0023 (6)0.0034 (7)0.0019 (7)
C100.0349 (9)0.0406 (10)0.0343 (9)−0.0015 (7)0.0003 (7)0.0042 (8)
C180.0306 (8)0.0423 (10)0.0320 (9)−0.0003 (7)0.0002 (7)0.0016 (8)
C70.0287 (8)0.0391 (9)0.0343 (9)−0.0018 (7)0.0006 (7)0.0073 (7)
C20.0319 (9)0.0440 (10)0.0371 (10)−0.0025 (7)0.0017 (7)0.0066 (8)
C60.0269 (8)0.0417 (10)0.0378 (9)0.0014 (7)0.0008 (7)0.0112 (8)
C130.0334 (9)0.0399 (10)0.0442 (11)0.0032 (7)0.0036 (8)0.0130 (8)
C230.0291 (8)0.0384 (9)0.0353 (9)−0.0026 (7)0.0008 (7)0.0066 (7)
C200.0344 (9)0.0343 (10)0.0485 (11)−0.0028 (8)0.0075 (8)0.0051 (8)
C210.0318 (9)0.0384 (10)0.0408 (10)−0.0061 (7)0.0020 (8)−0.0030 (8)
C120.0359 (9)0.0307 (9)0.0519 (12)0.0024 (7)0.0068 (8)0.0076 (8)
C50.0339 (9)0.0470 (11)0.0498 (12)0.0041 (8)0.0033 (8)0.0202 (9)
C190.0349 (9)0.0419 (10)0.0412 (10)0.0012 (7)0.0053 (8)0.0100 (8)
C40.0354 (10)0.0389 (10)0.0608 (13)0.0044 (8)0.0106 (9)0.0146 (10)
C110.0351 (9)0.0367 (10)0.0457 (11)−0.0036 (7)0.0058 (8)−0.0013 (8)
C80.0423 (11)0.0437 (11)0.0362 (10)−0.0059 (8)−0.0033 (9)0.0017 (8)
C160.0494 (12)0.0369 (10)0.0398 (11)−0.0013 (8)−0.0073 (9)−0.0001 (8)
C30.0349 (9)0.0401 (10)0.0509 (12)−0.0025 (8)0.0069 (8)0.0044 (9)
C240.0478 (11)0.0460 (11)0.0456 (12)−0.0031 (9)−0.0062 (9)0.0141 (9)
O2—H2C0.817 (16)C22—C171.391 (2)
O2—H2D0.812 (17)C22—C211.391 (3)
O1—H1A0.819 (17)C9—C101.383 (3)
O1—H2B0.810 (16)C15—C161.494 (3)
N1—C71.328 (2)C1—C21.381 (3)
N1—C11.393 (2)C1—C61.396 (2)
N1—H10.83 (2)C17—C181.384 (2)
N2—C71.322 (2)C10—C111.380 (3)
N2—C61.386 (3)C10—H100.95 (2)
N2—H20.71 (2)C18—C191.381 (3)
N3—C81.461 (3)C18—H180.91 (2)
N3—H3A0.87 (4)C7—C81.488 (3)
N3—H3B0.99 (3)C2—C31.381 (3)
N3—H30.88 (3)C2—H2A0.99 (2)
N4—C151.322 (2)C6—C51.390 (3)
N4—C91.392 (2)C13—C121.377 (3)
N4—H4A0.85 (2)C13—H130.97 (2)
N5—C151.324 (2)C23—C241.484 (3)
N5—C141.386 (2)C20—C211.377 (3)
N5—H5A0.83 (2)C20—C191.400 (3)
N6—C161.462 (3)C20—H200.87 (2)
N6—H6A0.86 (3)C21—H210.99 (2)
N6—H6B0.98 (3)C12—C111.399 (3)
N6—H6C0.79 (3)C12—H120.83 (2)
O3—H3D0.796 (17)C5—C41.366 (3)
O3—H3E0.822 (16)C5—H50.96 (2)
N7—C231.328 (2)C19—H190.99 (2)
N7—C171.391 (2)C4—C31.397 (3)
N7—H70.85 (3)C4—H40.92 (2)
N8—C231.332 (2)C11—H110.99 (2)
N8—C221.383 (2)C8—H8A0.92 (3)
N8—H80.80 (2)C8—H8B0.93 (3)
N9—C241.467 (3)C16—H16A0.92 (3)
N9—H9A0.83 (3)C16—H16B0.93 (2)
N9—H9B0.80 (3)C3—H3C0.93 (2)
N9—H9C0.99 (3)C24—H24A0.97 (2)
C14—C131.386 (2)C24—H24B0.97 (3)
C14—C91.395 (2)
H2C—O2—H2D104 (2)C19—C18—C17116.33 (18)
H1A—O1—H2B106 (2)C19—C18—H18120.3 (14)
C15—N4—C9108.99 (15)C17—C18—H18123.2 (14)
C15—N4—H4A124.8 (16)N2—C7—N1109.33 (16)
C9—N4—H4A125.4 (16)N2—C7—C8123.45 (17)
H3D—O3—H3E107 (2)N1—C7—C8127.11 (16)
C23—N7—C17108.55 (16)C3—C2—C1116.08 (18)
C23—N7—H7126.6 (17)C3—C2—H2A121.8 (12)
C17—N7—H7124.0 (17)C1—C2—H2A122.0 (12)
C15—N5—C14109.14 (15)N2—C6—C5132.85 (18)
C15—N5—H5A124.9 (15)N2—C6—C1106.35 (15)
C14—N5—H5A125.6 (15)C5—C6—C1120.80 (18)
C7—N1—C1109.27 (15)C12—C13—C14116.35 (17)
C7—N1—H1125.7 (17)C12—C13—H13124.6 (12)
C1—N1—H1124.5 (17)C14—C13—H13119.1 (12)
C7—N2—C6109.38 (16)N7—C23—N8109.72 (16)
C7—N2—H2126.4 (17)N7—C23—C24127.55 (18)
C6—N2—H2123.7 (17)N8—C23—C24122.63 (17)
C23—N8—C22108.85 (15)C21—C20—C19122.08 (18)
C23—N8—H8123.7 (15)C21—C20—H20117.6 (16)
C22—N8—H8127.0 (15)C19—C20—H20120.3 (15)
C16—N6—H6A111.4 (17)C20—C21—C22116.12 (18)
C16—N6—H6B115.5 (14)C20—C21—H21124.1 (13)
H6A—N6—H6B104 (2)C22—C21—H21119.7 (13)
C16—N6—H6C109 (2)C13—C12—C11122.09 (18)
H6A—N6—H6C110 (3)C13—C12—H12116.6 (16)
H6B—N6—H6C107 (2)C11—C12—H12121.3 (16)
C24—N9—H9A110.4 (18)C4—C5—C6116.97 (18)
C24—N9—H9B106.7 (18)C4—C5—H5124.2 (14)
H9A—N9—H9B109 (2)C6—C5—H5118.8 (14)
C24—N9—H9C113.6 (17)C18—C19—C20121.68 (18)
H9A—N9—H9C108 (2)C18—C19—H19116.2 (12)
H9B—N9—H9C109 (2)C20—C19—H19122.1 (12)
C8—N3—H3A108 (2)C5—C4—C3121.94 (19)
C8—N3—H3B114.2 (14)C5—C4—H4118.4 (13)
H3A—N3—H3B111 (2)C3—C4—H4119.6 (13)
C8—N3—H3111.0 (16)C10—C11—C12121.71 (19)
H3A—N3—H3106 (3)C10—C11—H11115.9 (12)
H3B—N3—H3107 (2)C12—C11—H11122.3 (12)
C13—C14—N5132.44 (17)N3—C8—C7112.34 (16)
C13—C14—C9121.46 (17)N3—C8—H8A110.4 (16)
N5—C14—C9106.11 (15)C7—C8—H8A110.8 (16)
N8—C22—C17106.45 (15)N3—C8—H8B109.5 (16)
N8—C22—C21131.74 (17)C7—C8—H8B109.3 (16)
C17—C22—C21121.81 (17)H8A—C8—H8B104 (2)
C10—C9—N4131.77 (16)N6—C16—C15112.13 (17)
C10—C9—C14122.19 (16)N6—C16—H16A113.4 (18)
N4—C9—C14106.02 (15)C15—C16—H16A108.1 (18)
N4—C15—N5109.73 (16)N6—C16—H16B108.5 (14)
N4—C15—C16127.44 (16)C15—C16—H16B109.5 (15)
N5—C15—C16122.72 (16)H16A—C16—H16B105 (2)
C2—C1—N1131.96 (16)C2—C3—C4121.8 (2)
C2—C1—C6122.37 (17)C2—C3—H3C118.8 (14)
N1—C1—C6105.66 (16)C4—C3—H3C119.4 (14)
C18—C17—C22121.97 (16)N9—C24—C23112.39 (17)
C18—C17—N7131.61 (17)N9—C24—H24A108.5 (15)
C22—C17—N7106.41 (15)C23—C24—H24A109.0 (14)
C11—C10—C9116.19 (17)N9—C24—H24B105 (2)
C11—C10—H10120.6 (12)C23—C24—H24B112 (2)
C9—C10—H10123.2 (12)H24A—C24—H24B110 (2)
C15—N5—C14—C13−179.30 (18)C7—N2—C6—C5178.55 (18)
C15—N5—C14—C90.93 (19)C7—N2—C6—C1−1.15 (19)
C23—N8—C22—C171.03 (19)C2—C1—C6—N2179.60 (15)
C23—N8—C22—C21−179.49 (17)N1—C1—C6—N20.52 (18)
C15—N4—C9—C10178.27 (18)C2—C1—C6—C5−0.1 (3)
C15—N4—C9—C14−0.41 (18)N1—C1—C6—C5−179.23 (15)
C13—C14—C9—C101.1 (3)N5—C14—C13—C12179.48 (17)
N5—C14—C9—C10−179.15 (15)C9—C14—C13—C12−0.8 (2)
C13—C14—C9—N4179.89 (15)C17—N7—C23—N81.29 (19)
N5—C14—C9—N4−0.31 (18)C17—N7—C23—C24−175.17 (18)
C9—N4—C15—N51.02 (19)C22—N8—C23—N7−1.5 (2)
C9—N4—C15—C16−175.38 (18)C22—N8—C23—C24175.21 (16)
C14—N5—C15—N4−1.22 (19)C19—C20—C21—C220.5 (3)
C14—N5—C15—C16175.38 (16)N8—C22—C21—C20179.87 (17)
C7—N1—C1—C2−178.68 (18)C17—C22—C21—C20−0.7 (2)
C7—N1—C1—C60.28 (18)C14—C13—C12—C110.2 (3)
N8—C22—C17—C18179.76 (15)N2—C6—C5—C4−179.37 (18)
C21—C22—C17—C180.2 (2)C1—C6—C5—C40.3 (3)
N8—C22—C17—N7−0.25 (17)C17—C18—C19—C20−0.8 (3)
C21—C22—C17—N7−179.79 (15)C21—C20—C19—C180.3 (3)
C23—N7—C17—C18179.37 (18)C6—C5—C4—C3−0.3 (3)
C23—N7—C17—C22−0.62 (18)C9—C10—C11—C120.0 (3)
N4—C9—C10—C11−179.14 (17)C13—C12—C11—C100.2 (3)
C14—C9—C10—C11−0.6 (2)N2—C7—C8—N3−178.27 (17)
C22—C17—C18—C190.5 (2)N1—C7—C8—N36.0 (3)
N7—C17—C18—C19−179.44 (17)N4—C15—C16—N6−6.7 (3)
C6—N2—C7—N11.4 (2)N5—C15—C16—N6177.37 (17)
C6—N2—C7—C8−175.02 (16)C1—C2—C3—C40.1 (3)
C1—N1—C7—N2−1.02 (19)C5—C4—C3—C20.1 (3)
C1—N1—C7—C8175.20 (17)N7—C23—C24—N9−8.3 (3)
N1—C1—C2—C3178.75 (17)N8—C23—C24—N9175.69 (17)
C6—C1—C2—C3−0.1 (2)
D—H···AD—HH···AD···AD—H···A
O1—H1A···Cl4i0.82 (2)2.63 (2)3.4431 (15)168 (3)
O1—H2B···Cl20.81 (2)2.36 (2)3.1598 (18)169 (3)
O2—H2C···Cl30.82 (2)2.33 (2)3.1244 (17)165 (2)
O2—H2D···Cl10.81 (1)2.64 (1)3.4492 (15)171 (3)
O3—H3D···Cl5ii0.80 (2)2.69 (2)3.4586 (15)164 (3)
O3—H3E···Cl6ii0.82 (2)2.32 (2)3.1364 (18)173 (3)
N1—H1···O10.83 (2)1.92 (2)2.746 (2)174 (2)
N2—H2···Cl1iii0.71 (2)2.44 (2)3.1519 (17)175 (2)
N3—H3···Cl30.88 (3)2.30 (3)3.105 (2)153 (2)
N3—H3A···Cl10.86 (4)2.26 (3)3.119 (2)173 (3)
N3—H3B···Cl4iv0.99 (3)2.33 (2)3.267 (2)156.8 (19)
N4—H4A···O20.85 (2)1.91 (2)2.754 (2)171 (2)
N5—H5A···Cl50.83 (2)2.31 (2)3.1205 (17)165 (2)
N6—H6A···Cl20.87 (3)2.33 (3)3.107 (2)150 (2)
N6—H6B···Cl1v0.98 (3)2.36 (2)3.287 (2)158.2 (18)
N6—H6C···Cl4i0.79 (3)2.35 (4)3.1347 (19)176 (3)
N7—H7···O30.85 (3)1.89 (3)2.742 (2)175 (3)
N8—H8···Cl40.81 (2)2.31 (2)3.1049 (17)172 (2)
N9—H9A···Cl60.83 (3)2.35 (3)3.100 (2)151 (2)
N9—H9B···Cl50.80 (3)2.32 (2)3.120 (2)176 (2)
N9—H9C···Cl5vi0.99 (3)2.34 (3)3.270 (2)157 (2)
C4—H4···Cl1i0.92 (2)2.81 (2)3.535 (2)136.7 (16)
C8—H8B···Cl3vii0.93 (3)2.65 (3)3.544 (2)162 (2)
  4 in total

1.  A concise synthesis of benzimidazoles via the microwave-assisted one-pot batch reaction of amino acids up to a 10-g scale.

Authors:  Pai Peng; Jin-Feng Xiong; Guang-Zhen Mo; Jia-Li Zheng; Ren-Hong Chen; Xiao-Yun Chen; Zhao-Yang Wang
Journal:  Amino Acids       Date:  2014-07-17       Impact factor: 3.520

2.  2,2',2''-(Nitrilo-trimethyl-ene)tris-(1H-benzimidazol-3-ium) trinitrate.

Authors:  Yi Cui
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-02-12

3.  Crystal structure refinement with SHELXL.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr C Struct Chem       Date:  2015-01-01       Impact factor: 1.172

4.  Structure validation in chemical crystallography.

Authors:  Anthony L Spek
Journal:  Acta Crystallogr D Biol Crystallogr       Date:  2009-01-20
  4 in total

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