organic compounds
(±)-1-(1-Allyl-1H-benzimidazol-2-yl)ethanol
aDepartment of Chemistry, Nanchang University, Nanchang 330031, People's Republic of China
*Correspondence e-mail: nculdp@126.com
The title compound, C12H14N2O, was obtained by reaction of (±)-1-(1H-benzimidazol-2-yl)ethanol with 3-bromoprop-1-ene. The contains four crystallographically independent molecules. In the crystal, molecules 1 and 2 are linked via O—H⋯N hydrogen bonds, forming chains propagating along [010]. Molecules 3 and 4 are linked to these chains via O—H⋯O hydrogen bonds.
Related literature
For background to the pharmaceutical properties and applications of benzimidazole derivatives, see: Garuti et al. (1999); Matsuno et al. (2000); Stibrany (2001); Stibrany et al. (2002). For the synthesis of the title compound, see Xia & Xu (2008).
Experimental
Crystal data
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Refinement
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Data collection: CrystalClear (Rigaku, 2005); cell CrystalClear; data reduction: CrystalClear; 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: SHELXL97.
Supporting information
10.1107/S1600536812044340/rz5017sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812044340/rz5017Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812044340/rz5017Isup3.cml
All chemicals were obtained from commercial sources and used directly without further purification. (+/-)-1-(1H-benzimidazol-2-yl)ethanol was synthesized according to the literature methos (Xia & Xu, 2008). (+/-)-1-(1H-benzimidazol-2-yl)ethanol (0.81 g, 5 mmol) was dissolved in acetone (10 ml), then 3-bromoprop-1-ene (0.6 g, 5 mmol) and K2CO3 (0.83 g, 6 mmol) was added to the solution. The mixture was heated to reflux for 15 h at 70°C. The organic solvent was removed under reduced pressure, and 50 ml chloroform was added. The solid was removed by filtration and washed with chloroform. The combined organic solution was washed with water, dried over anhydrous Na2SO4, and the solvent removed under reduced pressure. The residues was purified by choromatography column with CHCl3 to afford the pure light yellow solid (0.745 g, yield: 74%). 1H-NMR(CDCl3, 500 MHz): δ1.69 (d, 3 H), 3.66(br, 1H), 4.80(m, 2H), 4.98(d, 1H), 5.11 (q, 1 H), 5.21(d, 1 H), 5.94(m, 1 H), 7.25(m, 3H), 7.73 (m, 1 H). Single crystals of the title compound suitable for X-ray were obtained from a methanol solution by slow evaporation after a week.
All H atoms attached to C and O atom were fixed geometrically and treated as riding, with C—H = 0.98 Å (methine), 0.96 Å (methyl) or 0.93 Å(aromatic), O—H = 0.82 Å, and with Uiso (H) = 1.2Ueq (C) or 1.5Ueq(C, O) for methyl and hydroxy H atoms. In the absence of significant
3937 Friedel pairs have been merged.Data collection: CrystalClear (Rigaku, 2005); cell
CrystalClear (Rigaku, 2005); data reduction: CrystalClear (Rigaku, 2005); 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: SHELXL97 (Sheldrick, 2008).C12H14N2O | V = 1121.8 (4) Å3 |
Mr = 202.25 | Z = 4 |
Triclinic, P1 | F(000) = 432 |
Hall symbol: P 1 | Dx = 1.198 Mg m−3 |
a = 8.7816 (18) Å | Mo Kα radiation, λ = 0.71073 Å |
b = 9.1233 (18) Å | θ = 2.4–28.0° |
c = 14.773 (3) Å | µ = 0.08 mm−1 |
α = 96.66 (3)° | T = 293 K |
β = 107.15 (3)° | Block, colourless |
γ = 90.83 (3)° | 0.24 × 0.22 × 0.15 mm |
Rigaku Mercury2 (2x2 bin mode) diffractometer | 8368 independent reflections |
Radiation source: fine-focus sealed tube | 4897 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.031 |
Detector resolution: 13.6612 pixels mm-1 | θmax = 26.0°, θmin = 2.4° |
ω scans | h = −10→10 |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | k = −11→11 |
Tmin = 0.982, Tmax = 0.988 | l = −18→18 |
10277 measured reflections |
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)] = 0.055 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | w = 1/[σ2(Fo2) + (0.0586P)2] where P = (Fo2 + 2Fc2)/3 |
4404 reflections | (Δ/σ)max < 0.001 |
541 parameters | Δρmax = 0.16 e Å−3 |
3 restraints | Δρmin = −0.19 e Å−3 |
C12H14N2O | γ = 90.83 (3)° |
Mr = 202.25 | V = 1121.8 (4) Å3 |
Triclinic, P1 | Z = 4 |
a = 8.7816 (18) Å | Mo Kα radiation |
b = 9.1233 (18) Å | µ = 0.08 mm−1 |
c = 14.773 (3) Å | T = 293 K |
α = 96.66 (3)° | 0.24 × 0.22 × 0.15 mm |
β = 107.15 (3)° |
Rigaku Mercury2 (2x2 bin mode) diffractometer | 8368 independent reflections |
Absorption correction: multi-scan (CrystalClear; Rigaku, 2005) | 4897 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.988 | Rint = 0.031 |
10277 measured reflections |
R[F2 > 2σ(F2)] = 0.055 | 3 restraints |
wR(F2) = 0.128 | H-atom parameters constrained |
S = 1.02 | Δρmax = 0.16 e Å−3 |
4404 reflections | Δρmin = −0.19 e Å−3 |
541 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 | ||
C1 | 0.5685 (5) | 0.0013 (4) | 0.2505 (3) | 0.0458 (10) | |
C2 | 0.5232 (6) | −0.1444 (5) | 0.2097 (3) | 0.0582 (12) | |
H2A | 0.5454 | −0.2222 | 0.2463 | 0.070* | |
C3 | 0.4441 (6) | −0.1693 (6) | 0.1128 (4) | 0.0690 (14) | |
H3A | 0.4135 | −0.2654 | 0.0835 | 0.083* | |
C4 | 0.4100 (6) | −0.0526 (6) | 0.0590 (3) | 0.0712 (14) | |
H4A | 0.3558 | −0.0731 | −0.0058 | 0.085* | |
C5 | 0.4531 (6) | 0.0936 (6) | 0.0974 (3) | 0.0643 (13) | |
H5A | 0.4310 | 0.1708 | 0.0603 | 0.077* | |
C6 | 0.5318 (5) | 0.1171 (5) | 0.1951 (3) | 0.0489 (10) | |
C7 | 0.6574 (4) | 0.2036 (4) | 0.3452 (3) | 0.0435 (10) | |
C8 | 0.7359 (5) | 0.3134 (4) | 0.4309 (3) | 0.0479 (10) | |
H8A | 0.6697 | 0.3990 | 0.4307 | 0.058* | |
C9 | 0.7615 (6) | 0.2491 (5) | 0.5242 (3) | 0.0594 (12) | |
H9A | 0.8118 | 0.3233 | 0.5767 | 0.089* | |
H9B | 0.8284 | 0.1667 | 0.5254 | 0.089* | |
H9C | 0.6604 | 0.2167 | 0.5296 | 0.089* | |
C10 | 0.5846 (5) | 0.3949 (5) | 0.2284 (3) | 0.0556 (12) | |
H10A | 0.6017 | 0.4673 | 0.2844 | 0.067* | |
H10B | 0.4805 | 0.4084 | 0.1848 | 0.067* | |
C11 | 0.7095 (7) | 0.4188 (5) | 0.1814 (4) | 0.0688 (13) | |
H11A | 0.8146 | 0.4042 | 0.2150 | 0.083* | |
C12 | 0.6823 (9) | 0.4589 (7) | 0.0964 (5) | 0.104 (2) | |
H12A | 0.5786 | 0.4745 | 0.0607 | 0.125* | |
H12B | 0.7665 | 0.4719 | 0.0715 | 0.125* | |
C13 | 0.1628 (5) | 0.7216 (5) | 0.6969 (3) | 0.0472 (10) | |
C14 | 0.2453 (5) | 0.7395 (6) | 0.7940 (3) | 0.0627 (13) | |
H14A | 0.2719 | 0.8327 | 0.8289 | 0.075* | |
C15 | 0.2858 (6) | 0.6124 (6) | 0.8360 (3) | 0.0683 (14) | |
H15A | 0.3421 | 0.6202 | 0.9006 | 0.082* | |
C16 | 0.2449 (6) | 0.4733 (6) | 0.7843 (4) | 0.0662 (13) | |
H16A | 0.2742 | 0.3900 | 0.8150 | 0.079* | |
C17 | 0.1610 (5) | 0.4556 (5) | 0.6878 (3) | 0.0560 (12) | |
H17A | 0.1338 | 0.3620 | 0.6534 | 0.067* | |
C18 | 0.1189 (5) | 0.5824 (4) | 0.6439 (3) | 0.0445 (10) | |
C19 | 0.0315 (4) | 0.7439 (4) | 0.5469 (3) | 0.0428 (10) | |
C20 | −0.0486 (5) | 0.8173 (4) | 0.4616 (3) | 0.0478 (10) | |
H20A | 0.0186 | 0.9028 | 0.4596 | 0.057* | |
C21 | −0.0795 (6) | 0.7139 (5) | 0.3688 (3) | 0.0610 (12) | |
H21A | −0.1311 | 0.7656 | 0.3160 | 0.091* | |
H21B | −0.1469 | 0.6307 | 0.3699 | 0.091* | |
H21C | 0.0201 | 0.6800 | 0.3621 | 0.091* | |
C22 | 0.1121 (5) | 0.9846 (4) | 0.6599 (4) | 0.0564 (12) | |
H22A | 0.0953 | 1.0334 | 0.6030 | 0.068* | |
H22B | 0.2169 | 1.0169 | 0.7029 | 0.068* | |
C23 | −0.0127 (6) | 1.0274 (5) | 0.7075 (4) | 0.0688 (14) | |
H23A | −0.1190 | 1.0031 | 0.6733 | 0.083* | |
C24 | 0.0180 (9) | 1.0959 (7) | 0.7930 (5) | 0.106 (2) | |
H24A | 0.1230 | 1.1218 | 0.8290 | 0.127* | |
H24B | −0.0649 | 1.1194 | 0.8184 | 0.127* | |
C25 | 0.1235 (5) | 0.2875 (5) | 0.1527 (3) | 0.0510 (11) | |
C26 | 0.0739 (6) | 0.2591 (5) | 0.0539 (3) | 0.0646 (13) | |
H26A | 0.0475 | 0.1639 | 0.0220 | 0.077* | |
C27 | 0.0664 (7) | 0.3815 (6) | 0.0058 (4) | 0.0737 (14) | |
H27A | 0.0336 | 0.3679 | −0.0606 | 0.088* | |
C28 | 0.1059 (6) | 0.5232 (5) | 0.0528 (4) | 0.0726 (15) | |
H28A | 0.0992 | 0.6020 | 0.0173 | 0.087* | |
C29 | 0.1547 (6) | 0.5505 (5) | 0.1507 (4) | 0.0672 (13) | |
H29A | 0.1803 | 0.6462 | 0.1820 | 0.081* | |
C30 | 0.1644 (5) | 0.4289 (5) | 0.2017 (3) | 0.0525 (11) | |
C31 | 0.2025 (5) | 0.2829 (4) | 0.3089 (3) | 0.0466 (10) | |
C32 | 0.2450 (5) | 0.2198 (5) | 0.4023 (3) | 0.0508 (10) | |
H32A | 0.3255 | 0.1470 | 0.4008 | 0.061* | |
C33 | 0.3171 (6) | 0.3359 (5) | 0.4866 (3) | 0.0616 (12) | |
H33A | 0.3422 | 0.2909 | 0.5445 | 0.092* | |
H33B | 0.2421 | 0.4108 | 0.4887 | 0.092* | |
H33C | 0.4127 | 0.3798 | 0.4801 | 0.092* | |
C34 | 0.1221 (6) | 0.0331 (4) | 0.2065 (4) | 0.0594 (12) | |
H34A | 0.1757 | −0.0082 | 0.2645 | 0.071* | |
H34B | 0.1681 | −0.0067 | 0.1572 | 0.071* | |
C35 | −0.0505 (6) | −0.0127 (5) | 0.1766 (4) | 0.0705 (14) | |
H35A | −0.1110 | 0.0278 | 0.2145 | 0.085* | |
C36 | −0.1226 (8) | −0.1036 (6) | 0.1027 (5) | 0.0980 (19) | |
H36A | −0.0662 | −0.1465 | 0.0630 | 0.118* | |
H36B | −0.2312 | −0.1267 | 0.0889 | 0.118* | |
C37 | 0.5376 (5) | 1.0456 (5) | 0.6951 (3) | 0.0533 (11) | |
C38 | 0.5520 (6) | 1.1886 (6) | 0.7412 (4) | 0.0732 (15) | |
H38A | 0.5271 | 1.2690 | 0.7072 | 0.088* | |
C39 | 0.6052 (7) | 1.2070 (6) | 0.8401 (4) | 0.0818 (16) | |
H39A | 0.6149 | 1.3016 | 0.8729 | 0.098* | |
C40 | 0.6444 (7) | 1.0866 (7) | 0.8916 (4) | 0.0816 (16) | |
H40A | 0.6803 | 1.1032 | 0.9579 | 0.098* | |
C41 | 0.6314 (6) | 0.9450 (6) | 0.8468 (4) | 0.0728 (14) | |
H41A | 0.6571 | 0.8650 | 0.8812 | 0.087* | |
C42 | 0.5785 (5) | 0.9265 (5) | 0.7483 (3) | 0.0562 (12) | |
C43 | 0.4930 (5) | 0.8496 (5) | 0.5936 (3) | 0.0512 (11) | |
C44 | 0.4472 (5) | 0.7419 (5) | 0.5029 (3) | 0.0537 (11) | |
H44A | 0.3670 | 0.6703 | 0.5084 | 0.064* | |
C45 | 0.3721 (6) | 0.8175 (5) | 0.4162 (3) | 0.0629 (12) | |
H45A | 0.3447 | 0.7459 | 0.3602 | 0.094* | |
H45B | 0.4463 | 0.8915 | 0.4104 | 0.094* | |
H45C | 0.2774 | 0.8631 | 0.4228 | 0.094* | |
C46 | 0.5790 (6) | 0.6494 (5) | 0.7029 (4) | 0.0667 (14) | |
H46A | 0.5206 | 0.5808 | 0.6480 | 0.080* | |
H46B | 0.5404 | 0.6320 | 0.7561 | 0.080* | |
C47 | 0.7517 (7) | 0.6209 (6) | 0.7272 (4) | 0.0810 (16) | |
H47A | 0.8037 | 0.6350 | 0.6821 | 0.097* | |
C48 | 0.8330 (9) | 0.5788 (9) | 0.8051 (5) | 0.121 (3) | |
H48A | 0.7847 | 0.5637 | 0.8517 | 0.146* | |
H48B | 0.9409 | 0.5630 | 0.8157 | 0.146* | |
N1 | 0.6487 (4) | 0.0580 (4) | 0.3448 (2) | 0.0471 (8) | |
N2 | 0.5884 (4) | 0.2455 (3) | 0.2568 (2) | 0.0468 (8) | |
N3 | 0.0372 (4) | 0.5997 (4) | 0.5496 (2) | 0.0470 (8) | |
N4 | 0.1055 (4) | 0.8238 (4) | 0.6335 (2) | 0.0456 (8) | |
N5 | 0.2142 (4) | 0.4240 (4) | 0.3004 (3) | 0.0535 (9) | |
N6 | 0.1496 (4) | 0.1939 (4) | 0.2233 (3) | 0.0515 (9) | |
N7 | 0.4845 (4) | 0.9947 (4) | 0.5973 (3) | 0.0573 (10) | |
N8 | 0.5482 (4) | 0.8010 (4) | 0.6817 (3) | 0.0547 (9) | |
O1 | 0.8842 (3) | 0.3584 (3) | 0.4171 (2) | 0.0575 (8) | |
H1B | 0.9230 | 0.4234 | 0.4617 | 0.069* | |
O2 | −0.1956 (3) | 0.8682 (3) | 0.4758 (2) | 0.0577 (8) | |
H2B | −0.2118 | 0.9311 | 0.4392 | 0.069* | |
O3 | 0.1079 (4) | 0.1432 (3) | 0.4119 (2) | 0.0636 (8) | |
H3B | 0.0389 | 0.2020 | 0.4139 | 0.095* | |
O4 | 0.5825 (4) | 0.6616 (3) | 0.4948 (2) | 0.0656 (9) | |
H4B | 0.6509 | 0.7186 | 0.4889 | 0.098* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.044 (2) | 0.043 (2) | 0.048 (2) | −0.0030 (18) | 0.010 (2) | 0.0025 (19) |
C2 | 0.063 (3) | 0.047 (3) | 0.061 (3) | −0.004 (2) | 0.017 (3) | −0.003 (2) |
C3 | 0.073 (3) | 0.062 (3) | 0.067 (3) | −0.014 (3) | 0.022 (3) | −0.014 (3) |
C4 | 0.072 (3) | 0.084 (4) | 0.047 (3) | −0.010 (3) | 0.009 (3) | −0.011 (3) |
C5 | 0.062 (3) | 0.074 (3) | 0.053 (3) | −0.002 (3) | 0.011 (2) | 0.007 (3) |
C6 | 0.037 (2) | 0.052 (3) | 0.057 (3) | −0.0002 (19) | 0.012 (2) | 0.006 (2) |
C7 | 0.036 (2) | 0.043 (2) | 0.051 (3) | 0.0041 (18) | 0.013 (2) | 0.002 (2) |
C8 | 0.041 (2) | 0.043 (2) | 0.058 (3) | 0.0033 (18) | 0.014 (2) | 0.0006 (19) |
C9 | 0.069 (3) | 0.059 (3) | 0.048 (3) | −0.004 (2) | 0.016 (2) | 0.004 (2) |
C10 | 0.054 (3) | 0.047 (3) | 0.069 (3) | 0.007 (2) | 0.017 (2) | 0.019 (2) |
C11 | 0.074 (3) | 0.054 (3) | 0.084 (4) | −0.005 (2) | 0.030 (3) | 0.016 (3) |
C12 | 0.133 (6) | 0.095 (5) | 0.102 (5) | 0.005 (4) | 0.056 (4) | 0.032 (4) |
C13 | 0.043 (2) | 0.049 (2) | 0.051 (3) | 0.0064 (19) | 0.017 (2) | 0.005 (2) |
C14 | 0.056 (3) | 0.070 (3) | 0.053 (3) | 0.002 (3) | 0.007 (2) | −0.004 (2) |
C15 | 0.066 (3) | 0.086 (4) | 0.049 (3) | 0.005 (3) | 0.012 (3) | 0.008 (3) |
C16 | 0.063 (3) | 0.075 (3) | 0.064 (3) | 0.015 (3) | 0.016 (3) | 0.025 (3) |
C17 | 0.054 (3) | 0.055 (3) | 0.061 (3) | 0.009 (2) | 0.017 (2) | 0.015 (2) |
C18 | 0.041 (2) | 0.045 (2) | 0.048 (2) | 0.0037 (18) | 0.015 (2) | 0.0018 (19) |
C19 | 0.033 (2) | 0.043 (2) | 0.052 (3) | −0.0012 (17) | 0.014 (2) | 0.0045 (19) |
C20 | 0.048 (2) | 0.040 (2) | 0.056 (3) | 0.0050 (19) | 0.016 (2) | 0.0061 (19) |
C21 | 0.077 (3) | 0.055 (3) | 0.052 (3) | 0.005 (2) | 0.019 (2) | 0.009 (2) |
C22 | 0.059 (3) | 0.038 (2) | 0.069 (3) | −0.001 (2) | 0.018 (2) | −0.002 (2) |
C23 | 0.072 (3) | 0.052 (3) | 0.083 (4) | 0.008 (2) | 0.030 (3) | −0.007 (3) |
C24 | 0.123 (6) | 0.095 (5) | 0.106 (5) | 0.005 (4) | 0.057 (4) | −0.020 (4) |
C25 | 0.049 (2) | 0.047 (2) | 0.062 (3) | 0.011 (2) | 0.022 (2) | 0.011 (2) |
C26 | 0.081 (4) | 0.057 (3) | 0.056 (3) | 0.009 (3) | 0.020 (3) | 0.008 (2) |
C27 | 0.085 (4) | 0.077 (4) | 0.060 (3) | 0.013 (3) | 0.019 (3) | 0.018 (3) |
C28 | 0.089 (4) | 0.063 (3) | 0.067 (3) | 0.003 (3) | 0.019 (3) | 0.024 (3) |
C29 | 0.075 (3) | 0.051 (3) | 0.076 (4) | 0.001 (2) | 0.021 (3) | 0.013 (2) |
C30 | 0.051 (3) | 0.049 (3) | 0.058 (3) | 0.001 (2) | 0.017 (2) | 0.010 (2) |
C31 | 0.041 (2) | 0.047 (2) | 0.054 (3) | 0.0046 (19) | 0.016 (2) | 0.006 (2) |
C32 | 0.047 (2) | 0.044 (2) | 0.067 (3) | 0.0087 (19) | 0.022 (2) | 0.016 (2) |
C33 | 0.058 (3) | 0.063 (3) | 0.058 (3) | 0.005 (2) | 0.010 (2) | 0.006 (2) |
C34 | 0.065 (3) | 0.039 (2) | 0.074 (3) | 0.006 (2) | 0.020 (3) | 0.005 (2) |
C35 | 0.072 (3) | 0.056 (3) | 0.089 (4) | −0.005 (3) | 0.033 (3) | 0.010 (3) |
C36 | 0.085 (4) | 0.088 (4) | 0.108 (5) | −0.008 (4) | 0.010 (4) | 0.009 (4) |
C37 | 0.044 (2) | 0.058 (3) | 0.061 (3) | 0.009 (2) | 0.019 (2) | 0.010 (2) |
C38 | 0.078 (4) | 0.059 (3) | 0.076 (4) | 0.009 (3) | 0.015 (3) | 0.005 (3) |
C39 | 0.086 (4) | 0.072 (4) | 0.082 (4) | 0.007 (3) | 0.026 (3) | −0.011 (3) |
C40 | 0.079 (4) | 0.107 (5) | 0.060 (3) | 0.006 (3) | 0.025 (3) | 0.007 (3) |
C41 | 0.074 (4) | 0.080 (4) | 0.068 (3) | 0.009 (3) | 0.021 (3) | 0.019 (3) |
C42 | 0.048 (3) | 0.065 (3) | 0.061 (3) | 0.007 (2) | 0.021 (2) | 0.017 (2) |
C43 | 0.042 (2) | 0.047 (3) | 0.067 (3) | 0.003 (2) | 0.017 (2) | 0.013 (2) |
C44 | 0.045 (3) | 0.045 (2) | 0.073 (3) | 0.000 (2) | 0.021 (2) | 0.008 (2) |
C45 | 0.055 (3) | 0.060 (3) | 0.069 (3) | 0.002 (2) | 0.013 (2) | 0.002 (2) |
C46 | 0.066 (3) | 0.055 (3) | 0.085 (4) | 0.008 (2) | 0.024 (3) | 0.028 (3) |
C47 | 0.075 (4) | 0.075 (4) | 0.107 (4) | 0.026 (3) | 0.035 (3) | 0.043 (3) |
C48 | 0.093 (5) | 0.158 (7) | 0.129 (6) | 0.038 (5) | 0.034 (5) | 0.076 (5) |
N1 | 0.049 (2) | 0.0373 (19) | 0.053 (2) | 0.0011 (16) | 0.0136 (18) | 0.0013 (16) |
N2 | 0.045 (2) | 0.0405 (19) | 0.052 (2) | 0.0014 (15) | 0.0100 (17) | 0.0063 (16) |
N3 | 0.045 (2) | 0.043 (2) | 0.052 (2) | 0.0017 (16) | 0.0121 (17) | 0.0070 (16) |
N4 | 0.045 (2) | 0.0398 (19) | 0.050 (2) | 0.0014 (15) | 0.0148 (17) | −0.0013 (16) |
N5 | 0.056 (2) | 0.047 (2) | 0.060 (2) | 0.0061 (17) | 0.0182 (19) | 0.0114 (17) |
N6 | 0.052 (2) | 0.042 (2) | 0.061 (2) | 0.0063 (16) | 0.0168 (19) | 0.0099 (18) |
N7 | 0.060 (2) | 0.047 (2) | 0.064 (3) | 0.0065 (18) | 0.016 (2) | 0.0099 (18) |
N8 | 0.053 (2) | 0.051 (2) | 0.065 (3) | 0.0076 (18) | 0.021 (2) | 0.0155 (19) |
O1 | 0.0543 (18) | 0.0485 (17) | 0.0662 (19) | −0.0111 (14) | 0.0192 (15) | −0.0076 (14) |
O2 | 0.0560 (18) | 0.0567 (18) | 0.0671 (19) | 0.0160 (14) | 0.0230 (15) | 0.0213 (15) |
O3 | 0.0650 (19) | 0.0506 (17) | 0.083 (2) | 0.0016 (15) | 0.0296 (17) | 0.0195 (16) |
O4 | 0.0586 (19) | 0.0491 (17) | 0.092 (2) | 0.0072 (15) | 0.0274 (18) | 0.0055 (16) |
C1—C6 | 1.394 (6) | C25—N6 | 1.393 (5) |
C1—C2 | 1.395 (6) | C26—C27 | 1.384 (7) |
C1—N1 | 1.396 (5) | C26—H26A | 0.9300 |
C2—C3 | 1.385 (7) | C27—C28 | 1.383 (7) |
C2—H2A | 0.9300 | C27—H27A | 0.9300 |
C3—C4 | 1.385 (7) | C28—C29 | 1.373 (7) |
C3—H3A | 0.9300 | C28—H28A | 0.9300 |
C4—C5 | 1.388 (7) | C29—C30 | 1.402 (6) |
C4—H4A | 0.9300 | C29—H29A | 0.9300 |
C5—C6 | 1.394 (6) | C30—N5 | 1.399 (6) |
C5—H5A | 0.9300 | C31—N5 | 1.314 (5) |
C6—N2 | 1.385 (5) | C31—N6 | 1.371 (5) |
C7—N1 | 1.329 (5) | C31—C32 | 1.505 (6) |
C7—N2 | 1.369 (5) | C32—O3 | 1.434 (5) |
C7—C8 | 1.501 (6) | C32—C33 | 1.510 (6) |
C8—O1 | 1.438 (5) | C32—H32A | 0.9800 |
C8—C9 | 1.517 (6) | C33—H33A | 0.9600 |
C8—H8A | 0.9800 | C33—H33B | 0.9600 |
C9—H9A | 0.9600 | C33—H33C | 0.9600 |
C9—H9B | 0.9600 | C34—N6 | 1.463 (5) |
C9—H9C | 0.9600 | C34—C35 | 1.486 (7) |
C10—N2 | 1.470 (5) | C34—H34A | 0.9700 |
C10—C11 | 1.487 (7) | C34—H34B | 0.9700 |
C10—H10A | 0.9700 | C35—C36 | 1.284 (7) |
C10—H10B | 0.9700 | C35—H35A | 0.9300 |
C11—C12 | 1.303 (8) | C36—H36A | 0.9300 |
C11—H11A | 0.9300 | C36—H36B | 0.9300 |
C12—H12A | 0.9300 | C37—C38 | 1.386 (6) |
C12—H12B | 0.9300 | C37—N7 | 1.400 (6) |
C13—N4 | 1.392 (5) | C37—C42 | 1.404 (6) |
C13—C14 | 1.392 (6) | C38—C39 | 1.384 (7) |
C13—C18 | 1.397 (5) | C38—H38A | 0.9300 |
C14—C15 | 1.380 (7) | C39—C40 | 1.398 (8) |
C14—H14A | 0.9300 | C39—H39A | 0.9300 |
C15—C16 | 1.387 (7) | C40—C41 | 1.368 (8) |
C15—H15A | 0.9300 | C40—H40A | 0.9300 |
C16—C17 | 1.388 (7) | C41—C42 | 1.379 (7) |
C16—H16A | 0.9300 | C41—H41A | 0.9300 |
C17—C18 | 1.393 (6) | C42—N8 | 1.388 (6) |
C17—H17A | 0.9300 | C43—N7 | 1.323 (5) |
C18—N3 | 1.395 (5) | C43—N8 | 1.376 (5) |
C19—N3 | 1.322 (5) | C43—C44 | 1.512 (6) |
C19—N4 | 1.368 (5) | C44—O4 | 1.432 (5) |
C19—C20 | 1.489 (6) | C44—C45 | 1.508 (6) |
C20—O2 | 1.443 (5) | C44—H44A | 0.9800 |
C20—C21 | 1.522 (6) | C45—H45A | 0.9600 |
C20—H20A | 0.9800 | C45—H45B | 0.9600 |
C21—H21A | 0.9600 | C45—H45C | 0.9600 |
C21—H21B | 0.9600 | C46—N8 | 1.466 (5) |
C21—H21C | 0.9600 | C46—C47 | 1.487 (7) |
C22—N4 | 1.469 (5) | C46—H46A | 0.9700 |
C22—C23 | 1.501 (6) | C46—H46B | 0.9700 |
C22—H22A | 0.9700 | C47—C48 | 1.268 (8) |
C22—H22B | 0.9700 | C47—H47A | 0.9300 |
C23—C24 | 1.292 (7) | C48—H48A | 0.9300 |
C23—H23A | 0.9300 | C48—H48B | 0.9300 |
C24—H24A | 0.9300 | O1—H1B | 0.8201 |
C24—H24B | 0.9300 | O2—H2B | 0.8197 |
C25—C26 | 1.386 (6) | O3—H3B | 0.8200 |
C25—C30 | 1.391 (6) | O4—H4B | 0.8200 |
C6—C1—C2 | 120.6 (4) | C29—C28—H28A | 119.2 |
C6—C1—N1 | 109.5 (3) | C27—C28—H28A | 119.2 |
C2—C1—N1 | 130.0 (4) | C28—C29—C30 | 117.5 (4) |
C3—C2—C1 | 117.7 (4) | C28—C29—H29A | 121.2 |
C3—C2—H2A | 121.2 | C30—C29—H29A | 121.2 |
C1—C2—H2A | 121.2 | C25—C30—N5 | 110.6 (4) |
C2—C3—C4 | 120.7 (4) | C25—C30—C29 | 119.8 (4) |
C2—C3—H3A | 119.6 | N5—C30—C29 | 129.6 (4) |
C4—C3—H3A | 119.6 | N5—C31—N6 | 113.8 (4) |
C3—C4—C5 | 123.0 (5) | N5—C31—C32 | 124.7 (4) |
C3—C4—H4A | 118.5 | N6—C31—C32 | 121.5 (3) |
C5—C4—H4A | 118.5 | O3—C32—C31 | 110.0 (3) |
C4—C5—C6 | 115.7 (5) | O3—C32—C33 | 111.8 (4) |
C4—C5—H5A | 122.2 | C31—C32—C33 | 112.3 (4) |
C6—C5—H5A | 122.2 | O3—C32—H32A | 107.5 |
N2—C6—C5 | 131.6 (4) | C31—C32—H32A | 107.5 |
N2—C6—C1 | 106.1 (4) | C33—C32—H32A | 107.5 |
C5—C6—C1 | 122.3 (4) | C32—C33—H33A | 109.5 |
N1—C7—N2 | 112.5 (3) | C32—C33—H33B | 109.5 |
N1—C7—C8 | 125.2 (4) | H33A—C33—H33B | 109.5 |
N2—C7—C8 | 122.3 (4) | C32—C33—H33C | 109.5 |
O1—C8—C7 | 104.7 (3) | H33A—C33—H33C | 109.5 |
O1—C8—C9 | 111.9 (3) | H33B—C33—H33C | 109.5 |
C7—C8—C9 | 112.7 (3) | N6—C34—C35 | 112.3 (4) |
O1—C8—H8A | 109.2 | N6—C34—H34A | 109.1 |
C7—C8—H8A | 109.2 | C35—C34—H34A | 109.1 |
C9—C8—H8A | 109.2 | N6—C34—H34B | 109.1 |
C8—C9—H9A | 109.5 | C35—C34—H34B | 109.1 |
C8—C9—H9B | 109.5 | H34A—C34—H34B | 107.9 |
H9A—C9—H9B | 109.5 | C36—C35—C34 | 125.2 (5) |
C8—C9—H9C | 109.5 | C36—C35—H35A | 117.4 |
H9A—C9—H9C | 109.5 | C34—C35—H35A | 117.4 |
H9B—C9—H9C | 109.5 | C35—C36—H36A | 120.0 |
N2—C10—C11 | 110.9 (4) | C35—C36—H36B | 120.0 |
N2—C10—H10A | 109.5 | H36A—C36—H36B | 120.0 |
C11—C10—H10A | 109.5 | C38—C37—N7 | 129.6 (4) |
N2—C10—H10B | 109.5 | C38—C37—C42 | 120.1 (5) |
C11—C10—H10B | 109.5 | N7—C37—C42 | 110.3 (4) |
H10A—C10—H10B | 108.0 | C39—C38—C37 | 117.4 (5) |
C12—C11—C10 | 124.7 (6) | C39—C38—H38A | 121.3 |
C12—C11—H11A | 117.7 | C37—C38—H38A | 121.3 |
C10—C11—H11A | 117.7 | C38—C39—C40 | 121.5 (5) |
C11—C12—H12A | 120.0 | C38—C39—H39A | 119.2 |
C11—C12—H12B | 120.0 | C40—C39—H39A | 119.2 |
H12A—C12—H12B | 120.0 | C41—C40—C39 | 121.6 (5) |
N4—C13—C14 | 131.7 (4) | C41—C40—H40A | 119.2 |
N4—C13—C18 | 106.0 (4) | C39—C40—H40A | 119.2 |
C14—C13—C18 | 122.3 (4) | C40—C41—C42 | 116.9 (5) |
C15—C14—C13 | 116.8 (4) | C40—C41—H41A | 121.5 |
C15—C14—H14A | 121.6 | C42—C41—H41A | 121.5 |
C13—C14—H14A | 121.6 | C41—C42—N8 | 132.0 (5) |
C14—C15—C16 | 121.7 (5) | C41—C42—C37 | 122.5 (5) |
C14—C15—H15A | 119.1 | N8—C42—C37 | 105.5 (4) |
C16—C15—H15A | 119.1 | N7—C43—N8 | 113.9 (4) |
C15—C16—C17 | 121.4 (5) | N7—C43—C44 | 125.1 (4) |
C15—C16—H16A | 119.3 | N8—C43—C44 | 121.0 (4) |
C17—C16—H16A | 119.3 | O4—C44—C45 | 112.6 (4) |
C16—C17—C18 | 117.9 (4) | O4—C44—C43 | 110.1 (3) |
C16—C17—H17A | 121.1 | C45—C44—C43 | 111.8 (4) |
C18—C17—H17A | 121.1 | O4—C44—H44A | 107.4 |
C17—C18—N3 | 131.0 (4) | C45—C44—H44A | 107.4 |
C17—C18—C13 | 119.9 (4) | C43—C44—H44A | 107.4 |
N3—C18—C13 | 109.2 (4) | C44—C45—H45A | 109.5 |
N3—C19—N4 | 112.8 (4) | C44—C45—H45B | 109.5 |
N3—C19—C20 | 125.7 (4) | H45A—C45—H45B | 109.5 |
N4—C19—C20 | 121.5 (4) | C44—C45—H45C | 109.5 |
O2—C20—C19 | 105.9 (3) | H45A—C45—H45C | 109.5 |
O2—C20—C21 | 111.4 (4) | H45B—C45—H45C | 109.5 |
C19—C20—C21 | 112.3 (3) | N8—C46—C47 | 111.8 (4) |
O2—C20—H20A | 109.0 | N8—C46—H46A | 109.3 |
C19—C20—H20A | 109.0 | C47—C46—H46A | 109.3 |
C21—C20—H20A | 109.0 | N8—C46—H46B | 109.3 |
C20—C21—H21A | 109.5 | C47—C46—H46B | 109.3 |
C20—C21—H21B | 109.5 | H46A—C46—H46B | 107.9 |
H21A—C21—H21B | 109.5 | C48—C47—C46 | 124.4 (6) |
C20—C21—H21C | 109.5 | C48—C47—H47A | 117.8 |
H21A—C21—H21C | 109.5 | C46—C47—H47A | 117.8 |
H21B—C21—H21C | 109.5 | C47—C48—H48A | 120.0 |
N4—C22—C23 | 110.8 (3) | C47—C48—H48B | 120.0 |
N4—C22—H22A | 109.5 | H48A—C48—H48B | 120.0 |
C23—C22—H22A | 109.5 | C7—N1—C1 | 105.2 (4) |
N4—C22—H22B | 109.5 | C7—N2—C6 | 106.7 (3) |
C23—C22—H22B | 109.5 | C7—N2—C10 | 128.0 (4) |
H22A—C22—H22B | 108.1 | C6—N2—C10 | 125.2 (4) |
C24—C23—C22 | 124.2 (6) | C19—N3—C18 | 105.6 (3) |
C24—C23—H23A | 117.9 | C19—N4—C13 | 106.4 (3) |
C22—C23—H23A | 117.9 | C19—N4—C22 | 128.3 (4) |
C23—C24—H24A | 120.0 | C13—N4—C22 | 125.1 (4) |
C23—C24—H24B | 120.0 | C31—N5—C30 | 104.2 (4) |
H24A—C24—H24B | 120.0 | C31—N6—C25 | 106.2 (3) |
C26—C25—C30 | 123.1 (4) | C31—N6—C34 | 128.3 (4) |
C26—C25—N6 | 131.7 (4) | C25—N6—C34 | 125.5 (4) |
C30—C25—N6 | 105.2 (4) | C43—N7—C37 | 104.1 (4) |
C27—C26—C25 | 115.7 (5) | C43—N8—C42 | 106.2 (3) |
C27—C26—H26A | 122.2 | C43—N8—C46 | 128.0 (4) |
C25—C26—H26A | 122.2 | C42—N8—C46 | 125.7 (4) |
C28—C27—C26 | 122.4 (5) | C8—O1—H1B | 104.2 |
C28—C27—H27A | 118.8 | C20—O2—H2B | 98.1 |
C26—C27—H27A | 118.8 | C32—O3—H3B | 109.5 |
C29—C28—C27 | 121.6 (5) | C44—O4—H4B | 109.5 |
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···N3i | 0.82 | 1.99 | 2.801 (4) | 167 |
O2—H2B···N1ii | 0.82 | 2.05 | 2.811 (4) | 155 |
O3—H3B···O1iii | 0.82 | 1.99 | 2.808 (4) | 175 |
O4—H4B···O2i | 0.82 | 1.97 | 2.787 (4) | 176 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) x−1, y, z. |
Experimental details
Crystal data | |
Chemical formula | C12H14N2O |
Mr | 202.25 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.7816 (18), 9.1233 (18), 14.773 (3) |
α, β, γ (°) | 96.66 (3), 107.15 (3), 90.83 (3) |
V (Å3) | 1121.8 (4) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.24 × 0.22 × 0.15 |
Data collection | |
Diffractometer | Rigaku Mercury2 (2x2 bin mode) diffractometer |
Absorption correction | Multi-scan (CrystalClear; Rigaku, 2005) |
Tmin, Tmax | 0.982, 0.988 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10277, 8368, 4897 |
Rint | 0.031 |
(sin θ/λ)max (Å−1) | 0.617 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.055, 0.128, 1.02 |
No. of reflections | 4404 |
No. of parameters | 541 |
No. of restraints | 3 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.16, −0.19 |
Computer programs: CrystalClear (Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).
D—H···A | D—H | H···A | D···A | D—H···A |
O1—H1B···N3i | 0.82 | 1.99 | 2.801 (4) | 167.4 |
O2—H2B···N1ii | 0.82 | 2.05 | 2.811 (4) | 154.7 |
O3—H3B···O1iii | 0.82 | 1.99 | 2.808 (4) | 174.9 |
O4—H4B···O2i | 0.82 | 1.97 | 2.787 (4) | 175.6 |
Symmetry codes: (i) x+1, y, z; (ii) x−1, y+1, z; (iii) x−1, y, z. |
References
Garuti, L., Roberti, M. & Cermelli, C. (1999). Bioorg. Med. Chem. Lett. 9, 2525–2530. Web of Science CrossRef PubMed CAS Google Scholar
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Rigaku (2005). CrystalClear. Rigaku Corporation, Tokyo, Japan. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Stibrany, R. T. (2001). US Patent No. 6,180,788. Google Scholar
Stibrany, R. T., Schugar, H. J. & Potenza, J. A. (2002). Acta Cryst. E58, o1142–o1144. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Xia, R. & Xu, H.-J. (2008). Acta Cryst. E64, o1223. Web of Science CSD CrossRef IUCr Journals Google Scholar
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.
Benzimidazole and its derivatives are important pharmaceutical intermediates and have attracted considerable attention because of good biological and pharmaceutical activities (Matsuno, et al., 2000; Garuti, et al., 1999). These compounds also display other interesting properties as catalysts (Stibrany, 2001) and proton sponges (Stibrany et al., 2002). In this paper, the synthesis and crystal structure of the title compound is reported.
Fig. 1 shows an ORTEP plot of the title compound. There are four crystallographically independent molecules in the asymmetric unit. The C═C bonds are within normal ranges. The four benzimidazole ring systems are substantially planar with the the largest deviations from the mean plane of 0.018 (5), 0.008 (5), 0.018 (5) and 0.017 (5) Å for C1–C7/N1/N2, C13–C19/N3/N4, C25–C31/N5/N6 and C37–C43/N7/N8, respectively. In the structure of the title compound (Fig. 2), molecules are connected through intermolecular O—H···N and O—H···O hydrogen bonds into layers parallel to the (110) plane.