organic compounds
2-(1,3-Benzodioxol-5-yl)-1H-benzimidazole
aUnité de Recherche de Chimie de l'Environnement et Moléculaire Structurale (CHEMS), Faculté des Sciences Exactes, Département de Chimie, Université Constantine 1, Algeria
*Correspondence e-mail: king.ali@hotmail.fr
The 14H10N2O2, contains two independent molecules. In each molecule, the benzodioxole ring system displays an with the methylene C atom located at the flap deviating by 0.081 (2) and 0.230 (2) Å from the mean plane formed by the other atoms. The dihedral angles between the benzoimidazole ring system (all atoms) and the benzodioxole benzene ring are 15.35 (6) and 10.99 (7)°. In the crystal, molecules are linked by N—H⋯N hydrogen bonds into chains running along the [101].
of the title compound, CCCDC reference: 981105
Related literature
For the biological activity of imidazole derivatives and their use as inhibitors of neurodegenerative disorders and as antitumor drugs, see: Park et al. (1977). For related imidazole compounds, see: Andreani et al. (2005); Xu et al. (2010).
Experimental
Crystal data
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Data collection: KappaCCD Server Software (Nonius, 1999); cell KappaCCD Server Software; data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97.
Supporting information
CCDC reference: 981105
10.1107/S1600536814000737/xu5756sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814000737/xu5756Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814000737/xu5756Isup3.cml
A mixture of 1,2-diaminebenzene (2.3 g) and benzo[d][1,3]dioxole-5-carbaldehyde (0.02 mole) in ethanol (60 ml) was refluxed for 6 h. The yellow crystals obtained are filter and rinsed by a mixture of water ice ethanol, the recrystalization is done in excess of chloroform in 15 days.
The H atoms attached to C atoms and N atom were fixed geometrically and treated as riding with C—H = 0.93 Å (aromatic) or 0.97 Å (methylene) and N—H = 0.86 Å with Uiso(H) = 1.2Ueq(C,N).
Owing to the promising biological activities as inhibitors of neurodegenerative disorders and antitumor drugs (Park et al., 1977), most of these investigations were carried out with imidazole (Andreani et al., 2005; Xu et al., 2010).
A view of the molecular structure of (I) with numbering Scheme is Shown in Fig1. In the crystal, intermolecular N—H···N hydrogen bond Fig2, link the molecules into chains running along the [101] direction.
For the biological activity of imidazole derivatives and their use as inhibitors of neurodegenerative disorders and as antitumor drugs, see: Park et al. (1977). For related imidazole compounds, see: Andreani et al. (2005); Xu et al. (2010).
Data collection: KappaCCD Server Software (Nonius, 1999); cell
KappaCCD Server Software (Nonius, 1999); data reduction: DENZO and SCALEPACK (Otwinowski & Minor, 1997); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C14H10N2O2 | F(000) = 992 |
Mr = 238.24 | Dx = 1.398 Mg m−3 |
Monoclinic, P21/n | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: -P 2yn | Cell parameters from 5620 reflections |
a = 8.7454 (7) Å | θ = 2.5–25.1° |
b = 15.2824 (11) Å | µ = 0.10 mm−1 |
c = 16.9487 (13) Å | T = 293 K |
β = 91.974 (5)° | Prism, yellow |
V = 2263.9 (3) Å3 | 0.03 × 0.02 × 0.01 mm |
Z = 8 |
Nonius KappaCCD diffractometer | 3422 reflections with I > 2σ(I) |
Radiation source: fine-focus sealed tube | Rint = 0.018 |
Graphite monochromator | θmax = 25.1°, θmin = 1.8° |
CCD rotation images, thick slices scans | h = −10→10 |
13101 measured reflections | k = −18→18 |
4003 independent reflections | l = −18→20 |
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)] = 0.034 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0405P)2 + 0.8431P] where P = (Fo2 + 2Fc2)/3 |
4003 reflections | (Δ/σ)max = 0.001 |
325 parameters | Δρmax = 0.19 e Å−3 |
0 restraints | Δρmin = −0.18 e Å−3 |
C14H10N2O2 | V = 2263.9 (3) Å3 |
Mr = 238.24 | Z = 8 |
Monoclinic, P21/n | Mo Kα radiation |
a = 8.7454 (7) Å | µ = 0.10 mm−1 |
b = 15.2824 (11) Å | T = 293 K |
c = 16.9487 (13) Å | 0.03 × 0.02 × 0.01 mm |
β = 91.974 (5)° |
Nonius KappaCCD diffractometer | 3422 reflections with I > 2σ(I) |
13101 measured reflections | Rint = 0.018 |
4003 independent reflections |
R[F2 > 2σ(F2)] = 0.034 | 0 restraints |
wR(F2) = 0.088 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.19 e Å−3 |
4003 reflections | Δρmin = −0.18 e Å−3 |
325 parameters |
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. |
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 > 2sigma(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 | ||
N1 | 0.16720 (13) | 0.28274 (7) | 0.48294 (6) | 0.0245 (3) | |
H1N | 0.1584 | 0.2651 | 0.4348 | 0.029* | |
N2 | 0.27132 (13) | 0.34182 (7) | 0.59250 (6) | 0.0248 (3) | |
N3 | 0.46175 (13) | 0.33066 (7) | 0.72874 (7) | 0.0268 (3) | |
H3N | 0.4134 | 0.3292 | 0.6837 | 0.032* | |
N4 | 0.59892 (13) | 0.28499 (7) | 0.83388 (6) | 0.0251 (3) | |
O1 | 0.83709 (13) | 0.38755 (9) | 0.37149 (7) | 0.0532 (3) | |
O2 | 0.79659 (12) | 0.45860 (7) | 0.48949 (7) | 0.0413 (3) | |
O3 | 0.51495 (14) | −0.07450 (7) | 0.63889 (7) | 0.0452 (3) | |
O4 | 0.36723 (14) | 0.03150 (7) | 0.57597 (6) | 0.0439 (3) | |
C1 | 0.43467 (16) | 0.33554 (9) | 0.47685 (8) | 0.0248 (3) | |
C2 | 0.46177 (17) | 0.29304 (10) | 0.40626 (9) | 0.0330 (3) | |
H2 | 0.3889 | 0.2543 | 0.3855 | 0.040* | |
C3 | 0.59527 (18) | 0.30704 (11) | 0.36603 (9) | 0.0405 (4) | |
H3 | 0.6133 | 0.2787 | 0.3187 | 0.049* | |
C4 | 0.69848 (17) | 0.36405 (10) | 0.39901 (9) | 0.0342 (4) | |
C5 | 0.89677 (19) | 0.45149 (10) | 0.42461 (11) | 0.0414 (4) | |
H5A | 0.9041 | 0.5075 | 0.3980 | 0.050* | |
H5B | 0.9984 | 0.4346 | 0.4437 | 0.050* | |
C6 | 0.67386 (16) | 0.40628 (9) | 0.46969 (9) | 0.0290 (3) | |
C7 | 0.54339 (15) | 0.39333 (9) | 0.51010 (8) | 0.0260 (3) | |
H7 | 0.5273 | 0.4217 | 0.5577 | 0.031* | |
C8 | 0.29278 (15) | 0.32083 (8) | 0.51781 (7) | 0.0219 (3) | |
C9 | 0.12289 (16) | 0.31528 (9) | 0.60706 (8) | 0.0250 (3) | |
C10 | 0.03920 (17) | 0.32189 (9) | 0.67524 (8) | 0.0316 (3) | |
H10 | 0.0810 | 0.3474 | 0.7209 | 0.038* | |
C11 | −0.10750 (18) | 0.28935 (10) | 0.67265 (9) | 0.0380 (4) | |
H11 | −0.1653 | 0.2928 | 0.7176 | 0.046* | |
C12 | −0.17177 (18) | 0.25144 (10) | 0.60455 (10) | 0.0374 (4) | |
H12 | −0.2712 | 0.2299 | 0.6052 | 0.045* | |
C13 | −0.09151 (16) | 0.24510 (9) | 0.53635 (9) | 0.0308 (3) | |
H13 | −0.1348 | 0.2202 | 0.4908 | 0.037* | |
C14 | 0.05686 (15) | 0.27748 (8) | 0.53860 (8) | 0.0242 (3) | |
C15 | 0.53562 (15) | 0.17347 (9) | 0.73203 (8) | 0.0239 (3) | |
C16 | 0.63003 (16) | 0.11017 (9) | 0.76669 (9) | 0.0301 (3) | |
H16 | 0.6944 | 0.1257 | 0.8092 | 0.036* | |
C17 | 0.63104 (18) | 0.02407 (10) | 0.73960 (10) | 0.0365 (4) | |
H17 | 0.6943 | −0.0181 | 0.7631 | 0.044* | |
C18 | 0.53483 (17) | 0.00446 (9) | 0.67688 (9) | 0.0329 (3) | |
C19 | 0.3884 (2) | −0.06069 (11) | 0.58423 (10) | 0.0455 (4) | |
H19A | 0.4097 | −0.0866 | 0.5335 | 0.055* | |
H19B | 0.2967 | −0.0875 | 0.6039 | 0.055* | |
C20 | 0.44481 (17) | 0.06728 (10) | 0.64038 (8) | 0.0304 (3) | |
C21 | 0.44051 (17) | 0.15187 (9) | 0.66618 (8) | 0.0293 (3) | |
H21 | 0.3776 | 0.1933 | 0.6414 | 0.035* | |
C22 | 0.53328 (15) | 0.26200 (9) | 0.76528 (7) | 0.0227 (3) | |
C23 | 0.48053 (16) | 0.40285 (9) | 0.77669 (8) | 0.0272 (3) | |
C24 | 0.43107 (19) | 0.48911 (10) | 0.76926 (9) | 0.0371 (4) | |
H24 | 0.3734 | 0.5080 | 0.7254 | 0.045* | |
C25 | 0.4717 (2) | 0.54506 (10) | 0.83015 (10) | 0.0415 (4) | |
H25 | 0.4415 | 0.6033 | 0.8271 | 0.050* | |
C26 | 0.5574 (2) | 0.51643 (10) | 0.89636 (9) | 0.0395 (4) | |
H26 | 0.5823 | 0.5561 | 0.9364 | 0.047* | |
C27 | 0.60577 (18) | 0.43110 (10) | 0.90375 (9) | 0.0339 (3) | |
H27 | 0.6622 | 0.4124 | 0.9481 | 0.041* | |
C28 | 0.56718 (16) | 0.37349 (9) | 0.84232 (8) | 0.0256 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1 | 0.0275 (6) | 0.0278 (6) | 0.0181 (5) | −0.0007 (5) | −0.0025 (5) | −0.0013 (4) |
N2 | 0.0284 (6) | 0.0265 (6) | 0.0194 (6) | 0.0001 (5) | −0.0019 (5) | 0.0003 (4) |
N3 | 0.0318 (7) | 0.0279 (6) | 0.0203 (6) | 0.0001 (5) | −0.0069 (5) | 0.0008 (5) |
N4 | 0.0279 (6) | 0.0270 (6) | 0.0203 (6) | 0.0001 (5) | −0.0022 (5) | 0.0006 (5) |
O1 | 0.0384 (7) | 0.0707 (9) | 0.0516 (7) | −0.0127 (6) | 0.0180 (6) | −0.0126 (6) |
O2 | 0.0320 (6) | 0.0425 (6) | 0.0496 (7) | −0.0109 (5) | 0.0057 (5) | −0.0056 (5) |
O3 | 0.0553 (7) | 0.0301 (6) | 0.0501 (7) | −0.0003 (5) | 0.0000 (6) | −0.0116 (5) |
O4 | 0.0605 (8) | 0.0354 (6) | 0.0348 (6) | −0.0073 (5) | −0.0099 (5) | −0.0088 (5) |
C1 | 0.0265 (7) | 0.0248 (7) | 0.0228 (7) | 0.0036 (5) | −0.0038 (6) | 0.0024 (5) |
C2 | 0.0298 (8) | 0.0402 (9) | 0.0288 (8) | −0.0007 (6) | −0.0008 (6) | −0.0069 (6) |
C3 | 0.0381 (9) | 0.0535 (10) | 0.0303 (8) | −0.0005 (8) | 0.0063 (7) | −0.0128 (7) |
C4 | 0.0285 (8) | 0.0408 (9) | 0.0335 (8) | 0.0036 (6) | 0.0077 (7) | 0.0021 (7) |
C5 | 0.0340 (8) | 0.0338 (8) | 0.0573 (11) | −0.0026 (7) | 0.0140 (8) | 0.0051 (7) |
C6 | 0.0269 (7) | 0.0246 (7) | 0.0353 (8) | −0.0002 (6) | −0.0024 (6) | 0.0032 (6) |
C7 | 0.0282 (7) | 0.0255 (7) | 0.0242 (7) | 0.0020 (6) | 0.0001 (6) | 0.0003 (5) |
C8 | 0.0260 (7) | 0.0199 (6) | 0.0194 (7) | 0.0018 (5) | −0.0033 (5) | 0.0019 (5) |
C9 | 0.0281 (7) | 0.0229 (7) | 0.0240 (7) | 0.0031 (5) | −0.0007 (6) | 0.0049 (5) |
C10 | 0.0403 (9) | 0.0314 (8) | 0.0233 (7) | 0.0018 (6) | 0.0029 (6) | 0.0024 (6) |
C11 | 0.0394 (9) | 0.0394 (9) | 0.0359 (9) | 0.0033 (7) | 0.0115 (7) | 0.0090 (7) |
C12 | 0.0283 (8) | 0.0397 (9) | 0.0446 (9) | −0.0017 (7) | 0.0041 (7) | 0.0129 (7) |
C13 | 0.0288 (8) | 0.0306 (8) | 0.0326 (8) | −0.0028 (6) | −0.0041 (6) | 0.0058 (6) |
C14 | 0.0270 (7) | 0.0220 (7) | 0.0235 (7) | 0.0020 (5) | −0.0012 (6) | 0.0050 (5) |
C15 | 0.0227 (7) | 0.0277 (7) | 0.0216 (7) | −0.0025 (5) | 0.0041 (5) | 0.0006 (5) |
C16 | 0.0279 (7) | 0.0321 (8) | 0.0300 (8) | 0.0015 (6) | −0.0016 (6) | −0.0029 (6) |
C17 | 0.0366 (8) | 0.0306 (8) | 0.0421 (9) | 0.0084 (6) | −0.0011 (7) | −0.0016 (7) |
C18 | 0.0375 (8) | 0.0276 (8) | 0.0342 (8) | −0.0019 (6) | 0.0079 (7) | −0.0050 (6) |
C19 | 0.0595 (11) | 0.0351 (9) | 0.0415 (10) | −0.0096 (8) | −0.0008 (8) | −0.0115 (7) |
C20 | 0.0344 (8) | 0.0337 (8) | 0.0232 (7) | −0.0068 (6) | 0.0011 (6) | −0.0035 (6) |
C21 | 0.0349 (8) | 0.0283 (7) | 0.0246 (7) | −0.0012 (6) | −0.0022 (6) | 0.0020 (6) |
C22 | 0.0222 (7) | 0.0271 (7) | 0.0188 (7) | −0.0010 (5) | 0.0018 (5) | 0.0019 (5) |
C23 | 0.0302 (8) | 0.0277 (7) | 0.0236 (7) | −0.0012 (6) | −0.0009 (6) | 0.0009 (6) |
C24 | 0.0443 (9) | 0.0301 (8) | 0.0362 (9) | 0.0030 (7) | −0.0072 (7) | 0.0037 (6) |
C25 | 0.0521 (10) | 0.0268 (8) | 0.0456 (10) | 0.0031 (7) | −0.0006 (8) | −0.0020 (7) |
C26 | 0.0526 (10) | 0.0322 (8) | 0.0337 (9) | −0.0036 (7) | 0.0001 (8) | −0.0085 (6) |
C27 | 0.0411 (9) | 0.0364 (8) | 0.0239 (7) | −0.0030 (7) | −0.0043 (6) | −0.0027 (6) |
C28 | 0.0282 (7) | 0.0267 (7) | 0.0218 (7) | −0.0021 (6) | 0.0009 (6) | 0.0005 (5) |
N1—C8 | 1.3599 (17) | C9—C14 | 1.4025 (19) |
N1—C14 | 1.3749 (17) | C10—C11 | 1.375 (2) |
N1—H1N | 0.8600 | C10—H10 | 0.9300 |
N2—C8 | 1.3256 (17) | C11—C12 | 1.393 (2) |
N2—C9 | 1.3902 (18) | C11—H11 | 0.9300 |
N3—C22 | 1.3599 (17) | C12—C13 | 1.376 (2) |
N3—C23 | 1.3768 (18) | C12—H12 | 0.9300 |
N3—H3N | 0.8600 | C13—C14 | 1.388 (2) |
N4—C22 | 1.3261 (17) | C13—H13 | 0.9300 |
N4—C28 | 1.3890 (18) | C15—C16 | 1.389 (2) |
O1—C4 | 1.3619 (18) | C15—C21 | 1.4080 (19) |
O1—C5 | 1.416 (2) | C15—C22 | 1.4660 (19) |
O2—C6 | 1.3709 (17) | C16—C17 | 1.394 (2) |
O2—C5 | 1.4335 (19) | C16—H16 | 0.9300 |
O3—C18 | 1.3760 (18) | C17—C18 | 1.366 (2) |
O3—C19 | 1.434 (2) | C17—H17 | 0.9300 |
O4—C20 | 1.3784 (17) | C18—C20 | 1.375 (2) |
O4—C19 | 1.427 (2) | C19—H19A | 0.9700 |
C1—C2 | 1.389 (2) | C19—H19B | 0.9700 |
C1—C7 | 1.4017 (19) | C20—C21 | 1.366 (2) |
C1—C8 | 1.4600 (19) | C21—H21 | 0.9300 |
C2—C3 | 1.389 (2) | C23—C24 | 1.392 (2) |
C2—H2 | 0.9300 | C23—C28 | 1.3981 (19) |
C3—C4 | 1.361 (2) | C24—C25 | 1.377 (2) |
C3—H3 | 0.9300 | C24—H24 | 0.9300 |
C4—C6 | 1.384 (2) | C25—C26 | 1.398 (2) |
C5—H5A | 0.9700 | C25—H25 | 0.9300 |
C5—H5B | 0.9700 | C26—C27 | 1.375 (2) |
C6—C7 | 1.3652 (19) | C26—H26 | 0.9300 |
C7—H7 | 0.9300 | C27—C28 | 1.396 (2) |
C9—C10 | 1.3926 (19) | C27—H27 | 0.9300 |
C8—N1—C14 | 107.59 (11) | C12—C13—C14 | 117.08 (14) |
C8—N1—H1N | 126.2 | C12—C13—H13 | 121.5 |
C14—N1—H1N | 126.2 | C14—C13—H13 | 121.5 |
C8—N2—C9 | 105.23 (11) | N1—C14—C13 | 132.81 (13) |
C22—N3—C23 | 107.80 (11) | N1—C14—C9 | 105.36 (12) |
C22—N3—H3N | 126.1 | C13—C14—C9 | 121.83 (13) |
C23—N3—H3N | 126.1 | C16—C15—C21 | 119.89 (13) |
C22—N4—C28 | 105.45 (11) | C16—C15—C22 | 119.74 (12) |
C4—O1—C5 | 106.09 (12) | C21—C15—C22 | 120.35 (12) |
C6—O2—C5 | 105.20 (12) | C15—C16—C17 | 121.91 (14) |
C18—O3—C19 | 104.80 (12) | C15—C16—H16 | 119.0 |
C20—O4—C19 | 104.78 (12) | C17—C16—H16 | 119.0 |
C2—C1—C7 | 120.50 (13) | C18—C17—C16 | 116.92 (14) |
C2—C1—C8 | 120.70 (13) | C18—C17—H17 | 121.5 |
C7—C1—C8 | 118.80 (12) | C16—C17—H17 | 121.5 |
C3—C2—C1 | 121.48 (14) | C17—C18—C20 | 121.65 (14) |
C3—C2—H2 | 119.3 | C17—C18—O3 | 128.39 (14) |
C1—C2—H2 | 119.3 | C20—C18—O3 | 109.91 (13) |
C4—C3—C2 | 117.00 (14) | O4—C19—O3 | 107.66 (12) |
C4—C3—H3 | 121.5 | O4—C19—H19A | 110.2 |
C2—C3—H3 | 121.5 | O3—C19—H19A | 110.2 |
C3—C4—O1 | 127.87 (14) | O4—C19—H19B | 110.2 |
C3—C4—C6 | 122.23 (14) | O3—C19—H19B | 110.2 |
O1—C4—C6 | 109.90 (14) | H19A—C19—H19B | 108.5 |
O1—C5—O2 | 108.56 (12) | C21—C20—C18 | 122.58 (14) |
O1—C5—H5A | 110.0 | C21—C20—O4 | 127.65 (14) |
O2—C5—H5A | 110.0 | C18—C20—O4 | 109.76 (13) |
O1—C5—H5B | 110.0 | C20—C21—C15 | 116.98 (13) |
O2—C5—H5B | 110.0 | C20—C21—H21 | 121.5 |
H5A—C5—H5B | 108.4 | C15—C21—H21 | 121.5 |
C7—C6—O2 | 128.50 (13) | N4—C22—N3 | 111.92 (12) |
C7—C6—C4 | 121.62 (13) | N4—C22—C15 | 124.77 (12) |
O2—C6—C4 | 109.87 (13) | N3—C22—C15 | 123.32 (12) |
C6—C7—C1 | 117.17 (13) | N3—C23—C24 | 132.47 (13) |
C6—C7—H7 | 121.4 | N3—C23—C28 | 105.24 (12) |
C1—C7—H7 | 121.4 | C24—C23—C28 | 122.30 (13) |
N2—C8—N1 | 112.32 (12) | C25—C24—C23 | 116.66 (14) |
N2—C8—C1 | 124.57 (12) | C25—C24—H24 | 121.7 |
N1—C8—C1 | 123.11 (11) | C23—C24—H24 | 121.7 |
N2—C9—C10 | 130.30 (13) | C24—C25—C26 | 121.64 (15) |
N2—C9—C14 | 109.49 (12) | C24—C25—H25 | 119.2 |
C10—C9—C14 | 120.21 (13) | C26—C25—H25 | 119.2 |
C11—C10—C9 | 117.62 (14) | C27—C26—C25 | 121.64 (14) |
C11—C10—H10 | 121.2 | C27—C26—H26 | 119.2 |
C9—C10—H10 | 121.2 | C25—C26—H26 | 119.2 |
C10—C11—C12 | 121.76 (14) | C26—C27—C28 | 117.67 (14) |
C10—C11—H11 | 119.1 | C26—C27—H27 | 121.2 |
C12—C11—H11 | 119.1 | C28—C27—H27 | 121.2 |
C13—C12—C11 | 121.50 (14) | N4—C28—C27 | 130.30 (13) |
C13—C12—H12 | 119.3 | N4—C28—C23 | 109.59 (12) |
C11—C12—H12 | 119.3 | C27—C28—C23 | 120.09 (13) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N4i | 0.86 | 1.93 | 2.7761 (15) | 168 |
N3—H3N···N2 | 0.86 | 1.96 | 2.8053 (16) | 168 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1N···N4i | 0.86 | 1.93 | 2.7761 (15) | 168 |
N3—H3N···N2 | 0.86 | 1.96 | 2.8053 (16) | 168 |
Symmetry code: (i) x−1/2, −y+1/2, z−1/2. |
Acknowledgements
We thank all researchers of the CHEMS Research Unit, University of Constantine 1, Algeria, for their valuable assistance and the MESRS (Algeria) for financial support.
References
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Owing to the promising biological activities as inhibitors of neurodegenerative disorders and antitumor drugs (Park et al., 1977), most of these investigations were carried out with imidazole (Andreani et al., 2005; Xu et al., 2010).
A view of the molecular structure of (I) with numbering Scheme is Shown in Fig1. In the crystal, intermolecular N—H···N hydrogen bond Fig2, link the molecules into chains running along the [101] direction.