organic compounds
1-(4-Bromobenzyl)-2-(4-bromophenyl)-1H-benzimidazole
aKey Laboratory of Organosilicon Chemistry and Material Technology of the Ministry of Education, Hangzhou Normal University, No. 58, Haishu Road, Hangzhou, 311121, People's Republic of China
*Correspondence e-mail: quzr@hznu.edu.cn
There are two molecules in the 20H14Br2N2. In the first, the dihedral angles between the mean plane of the benzimidazole group and those of the 4-bromobenzyl and 4-chlorophenyl groups are 50.72 (17) and 71.29 (16)°, respectively, while the corresponding angles in the second molecule are 42.09 (16) and 89.05 (17)°. The 4-bromobenzyl and 4-bromophenyl groups make an angle of 68.1 (2) and 85.1 (21)° with each other in the two molecules. In the crystal, weak C—H⋯N and C—H⋯Br hydrogen bonds link the molecules along the c-axis direction. Br⋯Br interactions [3.5733 (9)Å] are also observed.
of the title compound, CCCDC reference: 998763
Related literature
For the chemistry of benzimidazoles, see: Steel (1990); Bhattacharya & Chaudhuri (2008); Horton et al. (2003); Boiani & González (2005); Bai et al. (2001); Hasegawa et al. (1999); Bouwman et al. (1990); Pujar & Bharamgoudar (1988). For their use in sunthesis, see: Sasaki et al. (1991); Wan et al. (2009).
Experimental
Crystal data
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Data collection: APEX2 (Bruker, 2004); cell SAINT (Bruker, 2004); 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
CCDC reference: 998763
10.1107/S1600536814009076/bx2457sup1.cif
contains datablocks I, New_Global_Publ_Block. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814009076/bx2457Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814009076/bx2457Isup3.cml
1.0 mmol 4-bromobenzaldehyde and 2 ml water were located in a round bottom flask, and 0.5 mmol benzene-1, 2-diamine was then added. Finally, 0.5 mmol TMSCl was injected to the mixture. The reaction was stirred at room temperature for 5 h to form homogeneous suspension. The suspension was then filtered and the residue was washed with 10 ml water to give product. The crude product was recrystallized with ethanol.
All H atoms were placed in calculated positions with C(sp3)—H = 0.97 and C(sp2)—H = 0.93 \%A, and torsion angles were refined. In the absence of significant
effects, Friedel pairs were averaged.Data collection: APEX2 (Bruker, 2004); cell
SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004); 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).C20H14Br2N2 | V = 1756.6 (3) Å3 |
Mr = 442.15 | Z = 4 |
Triclinic, P1 | F(000) = 872 |
Hall symbol: -P 1 | Dx = 1.672 Mg m−3 |
a = 9.7537 (9) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 10.5758 (10) Å | µ = 4.62 mm−1 |
c = 17.8255 (17) Å | T = 293 K |
α = 83.435 (2)° | Block, colorless |
β = 81.702 (2)° | 0.30 × 0.26 × 0.20 mm |
γ = 75.621 (2)° |
Bruker APEXII CCD diffractometer | 8094 independent reflections |
Radiation source: fine-focus sealed tube | 5171 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.034 |
ϕ and ω scans | θmax = 27.6°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −12→12 |
Tmin = 0.258, Tmax = 0.398 | k = −13→13 |
22195 measured reflections | l = −23→23 |
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)] = 0.041 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0682P)2 + 0.0252P] where P = (Fo2 + 2Fc2)/3 |
8094 reflections | (Δ/σ)max = 0.001 |
433 parameters | Δρmax = 0.78 e Å−3 |
0 restraints | Δρmin = −0.51 e Å−3 |
C20H14Br2N2 | γ = 75.621 (2)° |
Mr = 442.15 | V = 1756.6 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 9.7537 (9) Å | Mo Kα radiation |
b = 10.5758 (10) Å | µ = 4.62 mm−1 |
c = 17.8255 (17) Å | T = 293 K |
α = 83.435 (2)° | 0.30 × 0.26 × 0.20 mm |
β = 81.702 (2)° |
Bruker APEXII CCD diffractometer | 8094 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | 5171 reflections with I > 2σ(I) |
Tmin = 0.258, Tmax = 0.398 | Rint = 0.034 |
22195 measured reflections |
R[F2 > 2σ(F2)] = 0.041 | 0 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.78 e Å−3 |
8094 reflections | Δρmin = −0.51 e Å−3 |
433 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Br1 | −0.15730 (5) | 0.89638 (4) | 0.54077 (3) | 0.08072 (17) | |
Br2 | −0.16242 (6) | 0.32973 (6) | 0.10730 (4) | 0.1089 (2) | |
N1 | 0.3305 (3) | 0.4230 (3) | 0.32967 (15) | 0.0433 (6) | |
N2 | 0.3833 (3) | 0.3609 (3) | 0.44875 (15) | 0.0500 (7) | |
C1 | 0.3026 (3) | 0.4476 (3) | 0.40547 (18) | 0.0428 (7) | |
C2 | 0.4706 (3) | 0.2743 (3) | 0.3994 (2) | 0.0501 (8) | |
C3 | 0.5784 (4) | 0.1635 (4) | 0.4142 (2) | 0.0675 (11) | |
H3 | 0.5986 | 0.1356 | 0.4636 | 0.081* | |
C4 | 0.6537 (4) | 0.0968 (4) | 0.3541 (3) | 0.0782 (13) | |
H4 | 0.7261 | 0.0228 | 0.3629 | 0.094* | |
C5 | 0.6235 (4) | 0.1382 (4) | 0.2798 (3) | 0.0742 (12) | |
H5 | 0.6784 | 0.0922 | 0.2400 | 0.089* | |
C6 | 0.5146 (4) | 0.2452 (4) | 0.2633 (2) | 0.0621 (10) | |
H6 | 0.4926 | 0.2709 | 0.2140 | 0.075* | |
C7 | 0.4402 (3) | 0.3118 (3) | 0.32494 (19) | 0.0471 (8) | |
C8 | 0.1638 (3) | 0.4571 (3) | 0.23018 (17) | 0.0411 (7) | |
C9 | 0.1261 (3) | 0.3402 (3) | 0.25350 (19) | 0.0478 (8) | |
H9 | 0.1660 | 0.2877 | 0.2940 | 0.057* | |
C10 | 0.0299 (4) | 0.3001 (4) | 0.2176 (2) | 0.0602 (10) | |
H10 | 0.0055 | 0.2207 | 0.2331 | 0.072* | |
C11 | −0.0294 (4) | 0.3804 (4) | 0.1582 (2) | 0.0625 (10) | |
C12 | 0.0032 (4) | 0.4980 (4) | 0.1359 (2) | 0.0652 (10) | |
H12 | −0.0391 | 0.5520 | 0.0965 | 0.078* | |
C13 | 0.0992 (4) | 0.5355 (4) | 0.1723 (2) | 0.0547 (9) | |
H13 | 0.1211 | 0.6161 | 0.1574 | 0.066* | |
C14 | 0.1930 (3) | 0.5584 (3) | 0.43392 (17) | 0.0431 (7) | |
C15 | 0.2257 (3) | 0.6373 (3) | 0.4824 (2) | 0.0525 (8) | |
H15 | 0.3189 | 0.6218 | 0.4937 | 0.063* | |
C16 | 0.1234 (4) | 0.7384 (4) | 0.5144 (2) | 0.0584 (9) | |
H16 | 0.1461 | 0.7903 | 0.5473 | 0.070* | |
C17 | −0.0147 (3) | 0.7600 (3) | 0.49573 (19) | 0.0495 (8) | |
C18 | −0.0515 (3) | 0.6844 (3) | 0.44837 (19) | 0.0523 (9) | |
H18 | −0.1451 | 0.6999 | 0.4377 | 0.063* | |
C19 | 0.0526 (3) | 0.5847 (3) | 0.41662 (18) | 0.0479 (8) | |
H19 | 0.0292 | 0.5341 | 0.3832 | 0.057* | |
C20 | 0.2732 (3) | 0.5045 (3) | 0.26516 (18) | 0.0477 (8) | |
H20A | 0.3518 | 0.5118 | 0.2261 | 0.057* | |
H20B | 0.2297 | 0.5917 | 0.2810 | 0.057* | |
Br3 | 0.63928 (5) | 1.35816 (5) | −0.04992 (2) | 0.07448 (16) | |
Br4 | 0.74016 (4) | 0.49101 (4) | 0.33062 (3) | 0.07748 (16) | |
N3 | 0.2139 (3) | 0.9848 (2) | 0.18779 (14) | 0.0400 (6) | |
N4 | 0.1287 (3) | 1.0167 (3) | 0.07537 (15) | 0.0472 (6) | |
C21 | 0.2261 (3) | 1.0367 (3) | 0.11357 (17) | 0.0417 (7) | |
C22 | 0.0980 (3) | 0.9287 (3) | 0.19718 (17) | 0.0403 (7) | |
C23 | 0.0326 (4) | 0.8664 (3) | 0.2605 (2) | 0.0530 (9) | |
H23 | 0.0673 | 0.8531 | 0.3075 | 0.064* | |
C24 | −0.0858 (4) | 0.8261 (4) | 0.2497 (2) | 0.0593 (9) | |
H24 | −0.1333 | 0.7851 | 0.2907 | 0.071* | |
C25 | −0.1374 (4) | 0.8444 (4) | 0.1792 (2) | 0.0605 (10) | |
H25 | −0.2176 | 0.8148 | 0.1744 | 0.073* | |
C26 | −0.0721 (3) | 0.9056 (4) | 0.1164 (2) | 0.0542 (9) | |
H26 | −0.1060 | 0.9171 | 0.0694 | 0.065* | |
C27 | 0.0471 (3) | 0.9493 (3) | 0.12673 (18) | 0.0441 (7) | |
C28 | 0.3296 (3) | 1.1121 (3) | 0.07887 (17) | 0.0428 (7) | |
C29 | 0.4738 (3) | 1.0776 (3) | 0.08827 (19) | 0.0498 (8) | |
H29 | 0.5086 | 1.0045 | 0.1204 | 0.060* | |
C30 | 0.5661 (4) | 1.1508 (4) | 0.0504 (2) | 0.0526 (8) | |
H30 | 0.6623 | 1.1272 | 0.0568 | 0.063* | |
C31 | 0.5138 (4) | 1.2583 (4) | 0.00333 (19) | 0.0518 (8) | |
C32 | 0.3721 (4) | 1.2963 (4) | −0.0070 (2) | 0.0583 (9) | |
H32 | 0.3386 | 1.3704 | −0.0387 | 0.070* | |
C33 | 0.2796 (4) | 1.2225 (3) | 0.03065 (19) | 0.0523 (8) | |
H33 | 0.1836 | 1.2468 | 0.0237 | 0.063* | |
C34 | 0.4011 (3) | 0.8685 (3) | 0.26853 (17) | 0.0405 (7) | |
C35 | 0.4468 (4) | 0.8454 (4) | 0.33915 (19) | 0.0593 (10) | |
H35 | 0.4098 | 0.9070 | 0.3745 | 0.071* | |
C36 | 0.5462 (4) | 0.7330 (4) | 0.3592 (2) | 0.0663 (11) | |
H36 | 0.5747 | 0.7180 | 0.4077 | 0.080* | |
C37 | 0.6015 (3) | 0.6445 (3) | 0.3062 (2) | 0.0499 (8) | |
C38 | 0.5589 (3) | 0.6633 (3) | 0.23460 (19) | 0.0490 (8) | |
H38 | 0.5971 | 0.6018 | 0.1992 | 0.059* | |
C39 | 0.4581 (3) | 0.7755 (3) | 0.21666 (18) | 0.0468 (8) | |
H39 | 0.4277 | 0.7890 | 0.1686 | 0.056* | |
C40 | 0.2950 (3) | 0.9941 (3) | 0.24839 (18) | 0.0459 (8) | |
H40A | 0.2292 | 1.0191 | 0.2934 | 0.055* | |
H40B | 0.3456 | 1.0628 | 0.2331 | 0.055* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.0788 (3) | 0.0672 (3) | 0.0755 (3) | 0.0185 (2) | 0.0038 (2) | −0.0161 (2) |
Br2 | 0.0928 (4) | 0.1135 (4) | 0.1374 (5) | −0.0157 (3) | −0.0652 (3) | −0.0351 (4) |
N1 | 0.0403 (14) | 0.0471 (15) | 0.0417 (15) | −0.0073 (11) | −0.0073 (11) | −0.0042 (12) |
N2 | 0.0452 (15) | 0.0564 (17) | 0.0450 (15) | −0.0001 (13) | −0.0116 (12) | −0.0090 (13) |
C1 | 0.0391 (16) | 0.0477 (19) | 0.0423 (17) | −0.0088 (14) | −0.0080 (13) | −0.0056 (14) |
C2 | 0.0403 (17) | 0.052 (2) | 0.056 (2) | −0.0013 (15) | −0.0109 (15) | −0.0112 (16) |
C3 | 0.055 (2) | 0.065 (2) | 0.076 (3) | 0.0094 (19) | −0.0206 (19) | −0.012 (2) |
C4 | 0.060 (2) | 0.062 (3) | 0.108 (4) | 0.009 (2) | −0.017 (2) | −0.031 (2) |
C5 | 0.061 (2) | 0.079 (3) | 0.077 (3) | 0.003 (2) | −0.001 (2) | −0.038 (2) |
C6 | 0.057 (2) | 0.070 (3) | 0.059 (2) | −0.0081 (19) | −0.0032 (17) | −0.0253 (19) |
C7 | 0.0357 (16) | 0.054 (2) | 0.053 (2) | −0.0091 (14) | −0.0043 (14) | −0.0145 (16) |
C8 | 0.0412 (16) | 0.0445 (18) | 0.0340 (16) | −0.0038 (13) | −0.0007 (13) | −0.0067 (13) |
C9 | 0.0463 (18) | 0.0428 (19) | 0.052 (2) | −0.0029 (14) | −0.0135 (15) | −0.0013 (15) |
C10 | 0.052 (2) | 0.047 (2) | 0.083 (3) | −0.0071 (16) | −0.0150 (19) | −0.0115 (19) |
C11 | 0.048 (2) | 0.070 (3) | 0.071 (3) | −0.0017 (18) | −0.0218 (18) | −0.022 (2) |
C12 | 0.067 (2) | 0.075 (3) | 0.051 (2) | −0.007 (2) | −0.0215 (18) | 0.0022 (19) |
C13 | 0.056 (2) | 0.053 (2) | 0.050 (2) | −0.0093 (16) | −0.0040 (16) | 0.0083 (16) |
C14 | 0.0463 (17) | 0.0454 (18) | 0.0344 (16) | −0.0051 (14) | −0.0062 (13) | −0.0010 (13) |
C15 | 0.0433 (18) | 0.057 (2) | 0.056 (2) | −0.0050 (15) | −0.0127 (15) | −0.0088 (17) |
C16 | 0.063 (2) | 0.052 (2) | 0.060 (2) | −0.0064 (17) | −0.0101 (18) | −0.0136 (17) |
C17 | 0.0503 (19) | 0.0428 (18) | 0.0465 (19) | 0.0003 (15) | 0.0011 (15) | 0.0001 (15) |
C18 | 0.0434 (18) | 0.058 (2) | 0.0468 (19) | 0.0004 (15) | −0.0058 (15) | 0.0036 (16) |
C19 | 0.0468 (18) | 0.053 (2) | 0.0421 (18) | −0.0064 (15) | −0.0083 (14) | −0.0032 (15) |
C20 | 0.0546 (19) | 0.0498 (19) | 0.0389 (17) | −0.0142 (15) | −0.0045 (14) | −0.0022 (14) |
Br3 | 0.0869 (3) | 0.1047 (4) | 0.0508 (2) | −0.0628 (3) | −0.0016 (2) | −0.0045 (2) |
Br4 | 0.0602 (3) | 0.0730 (3) | 0.0883 (3) | 0.0071 (2) | −0.0228 (2) | 0.0056 (2) |
N3 | 0.0405 (13) | 0.0419 (14) | 0.0366 (14) | −0.0078 (11) | −0.0078 (10) | 0.0007 (11) |
N4 | 0.0477 (15) | 0.0530 (17) | 0.0406 (15) | −0.0120 (12) | −0.0097 (12) | 0.0033 (12) |
C21 | 0.0403 (16) | 0.0435 (18) | 0.0386 (17) | −0.0061 (13) | −0.0054 (13) | 0.0004 (13) |
C22 | 0.0399 (16) | 0.0381 (17) | 0.0387 (17) | −0.0034 (13) | −0.0041 (13) | 0.0010 (13) |
C23 | 0.059 (2) | 0.0447 (19) | 0.0473 (19) | −0.0027 (16) | −0.0013 (16) | 0.0022 (15) |
C24 | 0.052 (2) | 0.057 (2) | 0.063 (2) | −0.0135 (17) | 0.0059 (17) | 0.0041 (18) |
C25 | 0.0438 (19) | 0.058 (2) | 0.079 (3) | −0.0147 (17) | −0.0080 (18) | 0.005 (2) |
C26 | 0.0481 (19) | 0.059 (2) | 0.057 (2) | −0.0134 (16) | −0.0150 (16) | 0.0036 (17) |
C27 | 0.0417 (17) | 0.0449 (18) | 0.0428 (18) | −0.0078 (14) | −0.0041 (14) | 0.0024 (14) |
C28 | 0.0454 (17) | 0.0474 (18) | 0.0381 (17) | −0.0148 (14) | −0.0061 (13) | −0.0033 (14) |
C29 | 0.0490 (19) | 0.051 (2) | 0.0502 (19) | −0.0103 (16) | −0.0106 (15) | −0.0028 (16) |
C30 | 0.0422 (17) | 0.068 (2) | 0.053 (2) | −0.0191 (16) | −0.0050 (15) | −0.0127 (18) |
C31 | 0.058 (2) | 0.065 (2) | 0.0413 (18) | −0.0330 (18) | 0.0018 (15) | −0.0090 (16) |
C32 | 0.068 (2) | 0.058 (2) | 0.051 (2) | −0.0204 (19) | −0.0123 (18) | 0.0050 (17) |
C33 | 0.0518 (19) | 0.057 (2) | 0.049 (2) | −0.0173 (16) | −0.0104 (15) | 0.0078 (16) |
C34 | 0.0406 (16) | 0.0464 (18) | 0.0355 (16) | −0.0124 (13) | −0.0041 (12) | −0.0032 (13) |
C35 | 0.058 (2) | 0.078 (3) | 0.0351 (18) | 0.0038 (18) | −0.0091 (15) | −0.0170 (17) |
C36 | 0.057 (2) | 0.094 (3) | 0.0408 (19) | 0.001 (2) | −0.0134 (16) | −0.0055 (19) |
C37 | 0.0405 (17) | 0.054 (2) | 0.052 (2) | −0.0066 (15) | −0.0065 (15) | 0.0020 (16) |
C38 | 0.0515 (19) | 0.0449 (19) | 0.0494 (19) | −0.0077 (15) | −0.0072 (15) | −0.0060 (15) |
C39 | 0.0542 (19) | 0.0493 (19) | 0.0395 (17) | −0.0134 (15) | −0.0133 (14) | −0.0022 (14) |
C40 | 0.0537 (19) | 0.0464 (19) | 0.0378 (17) | −0.0095 (15) | −0.0083 (14) | −0.0053 (14) |
Br1—C17 | 1.899 (3) | Br3—C31 | 1.895 (3) |
Br2—C11 | 1.895 (4) | Br4—C37 | 1.890 (3) |
N1—C1 | 1.381 (4) | N3—C21 | 1.374 (4) |
N1—C7 | 1.381 (4) | N3—C22 | 1.383 (4) |
N1—C20 | 1.448 (4) | N3—C40 | 1.453 (4) |
N2—C1 | 1.308 (4) | N4—C21 | 1.316 (4) |
N2—C2 | 1.385 (4) | N4—C27 | 1.379 (4) |
C1—C14 | 1.460 (4) | C21—C28 | 1.464 (5) |
C2—C7 | 1.394 (5) | C22—C27 | 1.391 (4) |
C2—C3 | 1.395 (4) | C22—C23 | 1.395 (4) |
C3—C4 | 1.368 (6) | C23—C24 | 1.372 (5) |
C3—H3 | 0.9300 | C23—H23 | 0.9300 |
C4—C5 | 1.397 (6) | C24—C25 | 1.396 (5) |
C4—H4 | 0.9300 | C24—H24 | 0.9300 |
C5—C6 | 1.382 (5) | C25—C26 | 1.382 (5) |
C5—H5 | 0.9300 | C25—H25 | 0.9300 |
C6—C7 | 1.386 (5) | C26—C27 | 1.395 (5) |
C6—H6 | 0.9300 | C26—H26 | 0.9300 |
C8—C13 | 1.372 (4) | C28—C29 | 1.392 (4) |
C8—C9 | 1.378 (5) | C28—C33 | 1.396 (4) |
C8—C20 | 1.519 (5) | C29—C30 | 1.384 (5) |
C9—C10 | 1.379 (5) | C29—H29 | 0.9300 |
C9—H9 | 0.9300 | C30—C31 | 1.369 (5) |
C10—C11 | 1.380 (5) | C30—H30 | 0.9300 |
C10—H10 | 0.9300 | C31—C32 | 1.373 (5) |
C11—C12 | 1.361 (6) | C32—C33 | 1.389 (5) |
C12—C13 | 1.368 (5) | C32—H32 | 0.9300 |
C12—H12 | 0.9300 | C33—H33 | 0.9300 |
C13—H13 | 0.9300 | C34—C35 | 1.371 (4) |
C14—C15 | 1.387 (5) | C34—C39 | 1.386 (4) |
C14—C19 | 1.400 (4) | C34—C40 | 1.509 (4) |
C15—C16 | 1.382 (5) | C35—C36 | 1.382 (5) |
C15—H15 | 0.9300 | C35—H35 | 0.9300 |
C16—C17 | 1.392 (5) | C36—C37 | 1.366 (5) |
C16—H16 | 0.9300 | C36—H36 | 0.9300 |
C17—C18 | 1.366 (5) | C37—C38 | 1.376 (5) |
C18—C19 | 1.380 (5) | C38—C39 | 1.379 (4) |
C18—H18 | 0.9300 | C38—H38 | 0.9300 |
C19—H19 | 0.9300 | C39—H39 | 0.9300 |
C20—H20A | 0.9700 | C40—H40A | 0.9700 |
C20—H20B | 0.9700 | C40—H40B | 0.9700 |
C1—N1—C7 | 106.3 (2) | C21—N3—C22 | 106.3 (2) |
C1—N1—C20 | 128.2 (3) | C21—N3—C40 | 128.8 (3) |
C7—N1—C20 | 125.0 (3) | C22—N3—C40 | 124.7 (2) |
C1—N2—C2 | 104.9 (3) | C21—N4—C27 | 105.3 (3) |
N2—C1—N1 | 113.1 (3) | N4—C21—N3 | 112.6 (3) |
N2—C1—C14 | 123.8 (3) | N4—C21—C28 | 121.6 (3) |
N1—C1—C14 | 123.1 (3) | N3—C21—C28 | 125.7 (3) |
N2—C2—C7 | 110.5 (3) | N3—C22—C27 | 105.6 (3) |
N2—C2—C3 | 130.0 (3) | N3—C22—C23 | 132.0 (3) |
C7—C2—C3 | 119.5 (3) | C27—C22—C23 | 122.4 (3) |
C4—C3—C2 | 118.4 (4) | C24—C23—C22 | 116.2 (3) |
C4—C3—H3 | 120.8 | C24—C23—H23 | 121.9 |
C2—C3—H3 | 120.8 | C22—C23—H23 | 121.9 |
C3—C4—C5 | 121.0 (4) | C23—C24—C25 | 122.2 (3) |
C3—C4—H4 | 119.5 | C23—C24—H24 | 118.9 |
C5—C4—H4 | 119.5 | C25—C24—H24 | 118.9 |
C6—C5—C4 | 122.1 (4) | C26—C25—C24 | 121.5 (3) |
C6—C5—H5 | 118.9 | C26—C25—H25 | 119.2 |
C4—C5—H5 | 118.9 | C24—C25—H25 | 119.2 |
C5—C6—C7 | 115.9 (4) | C25—C26—C27 | 117.1 (3) |
C5—C6—H6 | 122.0 | C25—C26—H26 | 121.5 |
C7—C6—H6 | 122.0 | C27—C26—H26 | 121.5 |
N1—C7—C6 | 131.7 (3) | N4—C27—C22 | 110.2 (3) |
N1—C7—C2 | 105.2 (3) | N4—C27—C26 | 129.3 (3) |
C6—C7—C2 | 123.0 (3) | C22—C27—C26 | 120.6 (3) |
C13—C8—C9 | 118.5 (3) | C29—C28—C33 | 118.7 (3) |
C13—C8—C20 | 117.9 (3) | C29—C28—C21 | 124.4 (3) |
C9—C8—C20 | 123.7 (3) | C33—C28—C21 | 116.9 (3) |
C8—C9—C10 | 121.0 (3) | C30—C29—C28 | 120.8 (3) |
C8—C9—H9 | 119.5 | C30—C29—H29 | 119.6 |
C10—C9—H9 | 119.5 | C28—C29—H29 | 119.6 |
C9—C10—C11 | 118.5 (4) | C31—C30—C29 | 119.1 (3) |
C9—C10—H10 | 120.7 | C31—C30—H30 | 120.4 |
C11—C10—H10 | 120.7 | C29—C30—H30 | 120.4 |
C12—C11—C10 | 121.3 (3) | C30—C31—C32 | 121.9 (3) |
C12—C11—Br2 | 118.6 (3) | C30—C31—Br3 | 119.6 (3) |
C10—C11—Br2 | 120.1 (3) | C32—C31—Br3 | 118.5 (3) |
C11—C12—C13 | 119.0 (3) | C31—C32—C33 | 119.0 (3) |
C11—C12—H12 | 120.5 | C31—C32—H32 | 120.5 |
C13—C12—H12 | 120.5 | C33—C32—H32 | 120.5 |
C12—C13—C8 | 121.6 (4) | C32—C33—C28 | 120.5 (3) |
C12—C13—H13 | 119.2 | C32—C33—H33 | 119.7 |
C8—C13—H13 | 119.2 | C28—C33—H33 | 119.7 |
C15—C14—C19 | 118.3 (3) | C35—C34—C39 | 118.0 (3) |
C15—C14—C1 | 119.6 (3) | C35—C34—C40 | 120.1 (3) |
C19—C14—C1 | 122.0 (3) | C39—C34—C40 | 121.9 (3) |
C16—C15—C14 | 121.7 (3) | C34—C35—C36 | 121.9 (3) |
C16—C15—H15 | 119.2 | C34—C35—H35 | 119.1 |
C14—C15—H15 | 119.2 | C36—C35—H35 | 119.1 |
C15—C16—C17 | 117.8 (3) | C37—C36—C35 | 118.4 (3) |
C15—C16—H16 | 121.1 | C37—C36—H36 | 120.8 |
C17—C16—H16 | 121.1 | C35—C36—H36 | 120.8 |
C18—C17—C16 | 122.4 (3) | C36—C37—C38 | 121.8 (3) |
C18—C17—Br1 | 119.3 (3) | C36—C37—Br4 | 119.8 (3) |
C16—C17—Br1 | 118.3 (3) | C38—C37—Br4 | 118.4 (3) |
C17—C18—C19 | 118.8 (3) | C37—C38—C39 | 118.4 (3) |
C17—C18—H18 | 120.6 | C37—C38—H38 | 120.8 |
C19—C18—H18 | 120.6 | C39—C38—H38 | 120.8 |
C18—C19—C14 | 121.0 (3) | C38—C39—C34 | 121.5 (3) |
C18—C19—H19 | 119.5 | C38—C39—H39 | 119.2 |
C14—C19—H19 | 119.5 | C34—C39—H39 | 119.2 |
N1—C20—C8 | 115.7 (3) | N3—C40—C34 | 113.7 (3) |
N1—C20—H20A | 108.4 | N3—C40—H40A | 108.8 |
C8—C20—H20A | 108.4 | C34—C40—H40A | 108.8 |
N1—C20—H20B | 108.4 | N3—C40—H40B | 108.8 |
C8—C20—H20B | 108.4 | C34—C40—H40B | 108.8 |
H20A—C20—H20B | 107.4 | H40A—C40—H40B | 107.7 |
C2—N2—C1—N1 | 0.5 (4) | C27—N4—C21—N3 | 0.5 (3) |
C2—N2—C1—C14 | 179.8 (3) | C27—N4—C21—C28 | −176.9 (3) |
C7—N1—C1—N2 | −1.0 (4) | C22—N3—C21—N4 | −0.7 (3) |
C20—N1—C1—N2 | −173.0 (3) | C40—N3—C21—N4 | −175.6 (3) |
C7—N1—C1—C14 | 179.7 (3) | C22—N3—C21—C28 | 176.6 (3) |
C20—N1—C1—C14 | 7.7 (5) | C40—N3—C21—C28 | 1.6 (5) |
C1—N2—C2—C7 | 0.1 (4) | C21—N3—C22—C27 | 0.6 (3) |
C1—N2—C2—C3 | 179.3 (4) | C40—N3—C22—C27 | 175.8 (3) |
N2—C2—C3—C4 | −177.4 (4) | C21—N3—C22—C23 | −177.3 (3) |
C7—C2—C3—C4 | 1.7 (6) | C40—N3—C22—C23 | −2.1 (5) |
C2—C3—C4—C5 | −0.2 (7) | N3—C22—C23—C24 | 177.6 (3) |
C3—C4—C5—C6 | −1.8 (7) | C27—C22—C23—C24 | 0.1 (5) |
C4—C5—C6—C7 | 2.1 (6) | C22—C23—C24—C25 | 0.8 (5) |
C1—N1—C7—C6 | −177.4 (4) | C23—C24—C25—C26 | −0.5 (6) |
C20—N1—C7—C6 | −5.1 (6) | C24—C25—C26—C27 | −0.6 (5) |
C1—N1—C7—C2 | 1.0 (4) | C21—N4—C27—C22 | −0.1 (4) |
C20—N1—C7—C2 | 173.3 (3) | C21—N4—C27—C26 | 178.8 (3) |
C5—C6—C7—N1 | 177.6 (4) | N3—C22—C27—N4 | −0.3 (3) |
C5—C6—C7—C2 | −0.5 (6) | C23—C22—C27—N4 | 177.8 (3) |
N2—C2—C7—N1 | −0.7 (4) | N3—C22—C27—C26 | −179.3 (3) |
C3—C2—C7—N1 | −180.0 (3) | C23—C22—C27—C26 | −1.1 (5) |
N2—C2—C7—C6 | 177.9 (3) | C25—C26—C27—N4 | −177.4 (3) |
C3—C2—C7—C6 | −1.4 (6) | C25—C26—C27—C22 | 1.4 (5) |
C13—C8—C9—C10 | 2.6 (5) | N4—C21—C28—C29 | −137.9 (3) |
C20—C8—C9—C10 | −177.6 (3) | N3—C21—C28—C29 | 45.0 (5) |
C8—C9—C10—C11 | −0.8 (5) | N4—C21—C28—C33 | 39.1 (4) |
C9—C10—C11—C12 | −1.3 (6) | N3—C21—C28—C33 | −137.9 (3) |
C9—C10—C11—Br2 | −179.9 (3) | C33—C28—C29—C30 | −0.3 (5) |
C10—C11—C12—C13 | 1.4 (6) | C21—C28—C29—C30 | 176.7 (3) |
Br2—C11—C12—C13 | −180.0 (3) | C28—C29—C30—C31 | 0.1 (5) |
C11—C12—C13—C8 | 0.5 (6) | C29—C30—C31—C32 | 0.4 (5) |
C9—C8—C13—C12 | −2.5 (5) | C29—C30—C31—Br3 | −179.2 (3) |
C20—C8—C13—C12 | 177.7 (3) | C30—C31—C32—C33 | −0.8 (6) |
N2—C1—C14—C15 | 49.0 (5) | Br3—C31—C32—C33 | 178.8 (3) |
N1—C1—C14—C15 | −131.8 (3) | C31—C32—C33—C28 | 0.6 (5) |
N2—C1—C14—C19 | −128.0 (4) | C29—C28—C33—C32 | −0.1 (5) |
N1—C1—C14—C19 | 51.2 (5) | C21—C28—C33—C32 | −177.3 (3) |
C19—C14—C15—C16 | 1.1 (5) | C39—C34—C35—C36 | −0.3 (6) |
C1—C14—C15—C16 | −176.1 (3) | C40—C34—C35—C36 | −178.5 (4) |
C14—C15—C16—C17 | −0.7 (5) | C34—C35—C36—C37 | 1.2 (6) |
C15—C16—C17—C18 | 0.9 (5) | C35—C36—C37—C38 | −1.3 (6) |
C15—C16—C17—Br1 | 178.8 (3) | C35—C36—C37—Br4 | 178.9 (3) |
C16—C17—C18—C19 | −1.4 (5) | C36—C37—C38—C39 | 0.4 (5) |
Br1—C17—C18—C19 | −179.3 (2) | Br4—C37—C38—C39 | −179.7 (3) |
C17—C18—C19—C14 | 1.7 (5) | C37—C38—C39—C34 | 0.6 (5) |
C15—C14—C19—C18 | −1.6 (5) | C35—C34—C39—C38 | −0.6 (5) |
C1—C14—C19—C18 | 175.5 (3) | C40—C34—C39—C38 | 177.6 (3) |
C1—N1—C20—C8 | −107.0 (4) | C21—N3—C40—C34 | −106.7 (3) |
C7—N1—C20—C8 | 82.3 (4) | C22—N3—C40—C34 | 79.2 (4) |
C13—C8—C20—N1 | 175.6 (3) | C35—C34—C40—N3 | −156.4 (3) |
C9—C8—C20—N1 | −4.2 (4) | C39—C34—C40—N3 | 25.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Br3i | 0.93 | 2.85 | 3.433 (4) | 122 |
C26—H26···N4ii | 0.93 | 2.62 | 3.513 (4) | 161 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+2, −z. |
D—H···A | D—H | H···A | D···A | D—H···A |
C13—H13···Br3i | 0.93 | 2.85 | 3.433 (4) | 122 |
C26—H26···N4ii | 0.93 | 2.62 | 3.513 (4) | 161 |
Symmetry codes: (i) −x+1, −y+2, −z; (ii) −x, −y+2, −z. |
Acknowledgements
This work was supported by a start-up grant from Hangzhou Normal University to Z-RQ.
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This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Organic ligands containing multiple heterocyclic rings are very useful tools in the self-assembly of metallosupramolecular compounds (Steel, 1990). Functionalized benzimidazoles represent an important class of N-containing heterocyclic compounds and have received considerable attention in recent times because their derivatives bear versatile pharmacological properties (Bhattacharya & Chaudhuri, 2008) based on their presence in both clinical medicines (Horton et al., 2003) and compounds of broad biological functions (Boiani et al., 2005). They are important intermediates in many organic reactions (Bai et al., 2001; Hasegawa et al., 1999), and act as ligands to transition metals for modelling biological systems (Bouwman et al., 1990; Pujar et al., 1988). Herein, we report the synthesis and crystal structure of a new benzimidazole derivative 1-(4-bromobenzyl)-2-(4-bromophenyl)-1H-benzimidazole (Fig. 1)·In the title compound C20H14N2Br2, there are two molecules in the asymmetric unit. The dihedral angles between the least-squares plane of the benzimidazole group and those of the 4-bromobenzyl and 4-chlorophenyl groups are 50.72 (17); 42.09 (16) and 71.29 (16);89.05 (17) respectively. The 4-bromobenzyl and 4-bromophenyl groups make an angle of 68.1 (2); 85.1 (2) (1) with each other. Weak intramolecular hydrogen bonds of C—H···N and Br···Br interactions are observed.