organic compounds
4-Methyl-N-(2-phenylethyl)-2-propyl-1H-benzimidazole-6-carboxamide
aR&D Center for Pharmaceuticals, School of Chemical Engineering & the Environment, Beijing Institute of Technology, Beijing 100083, People's Republic of China, and bSINOPEC Research Institute of Petroleum Processing, Beijing 100083, People's Republic of China
*Correspondence e-mail: jims-wang@hotmail.com
There are two independent molecules in the 20H23N3O, in which the dihedral angles between the phenyl ring of the phenylethylamino group and the benzimidazole system are 73.98 (15) and 15.93 (16)°. The crystal packing features N—H⋯O and N—H⋯N hydrogen bonds.
of the title compound, CRelated literature
For the background to the title compound and its derivatives, see Mahiuddin et al. (2007); Namrata et al. (2012); Zhang et al. (2012); For hydrogen bonding, see: Desiraju (1995).
Experimental
Crystal data
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Refinement
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Data collection: APEX2 (Bruker 2007); cell APEX2 and SAINT (Bruker 2007); 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 and PLATON (Spek, 2009).
Supporting information
https://doi.org/10.1107/S1600536812036707/zj2085sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812036707/zj2085Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812036707/zj2085Isup3.cml
A suspension of 4-methyl-2-propyl-1H-benzimidazole-6-carboxylic acid (2.18 g, 10 mmol) in thionyl chloride (20 ml, 276 mmol) was refluxed for 2 h, and then the excess thionyl chloride was removed under reduced pressure to provide the crude acid chloride as an off-white solid. The crude product was used in the next step without further purification. To a stirred suspension of above acid chloride in 100 ml of dichloromethane at 293 K was added triethylamine (1.52 g, 15 mmol) dropwise, followed by a solution of phenylethylamine (10 mmol) in 10 ml of dichloromethane. The resulted mixture was stirred overnight and then was filtered, the filtrate was washed with brine and dried over anhydrous sodium sulphate, then was filtered and concentrated. The residue was purified by
(ethyl acetate–methanol, 4:1 v/v) to afford the title compound as a white solid, yield 72%, m.p. 425 ~ 427 K; Single crystals suitable for X-ray diffraction were prepared by slow evaporation of a solution of the title compound in ethanol at room temperature.The completeness of the final
is less than 97 percent due to the deficient diffraction on high degree.All H atoms were discernible in the difference electron density maps.Nevertheless, the hydrogen atoms were placed into idealized positions and allowed to ride on their respective carrier atoms, with C—H = 0.93 for aryl, 0.96 Å and 0.97 Å for methyl and methylene H atoms, respectively. The N—H bonds were defined with constraint at 0.88 Å. Uiso(H) = 1.2Ueq(C)aryl/methylene/methyl.Benzimidazole is an important scaffold with biological activities generally ultilized in antihypertensive drugs, proton pump inhibitors and antimicrobial agents, etc. (Mahiuddin et al., 2007.; Namrata et al., 2012). As a part of our study of 6-substituted carbamoyl benzimidazoles as a nonpeptidic angiotensin II AT1 receptor antagonist (Zhang et al., 2012), herein we report the synthesis and
of the title compound of this family. In the of the title compound, there are two independent molecules with different dihedral angles between the phenyl ring of the phenylethylamino and the benzimidazole ring. In the O1(carbonyl)-containing molecule, the dihedral angle between the phenyl ring of the phenylethylamino and the benzimidazole ring is -1.8 (5) °, while the O2(carbonyl)-containing one has the value of -1.0 (5) ° (Fig. 1). Intermolecular N—H···O and N—H···N hydrogen-bonding (Desiraju, 1995) interactions (Table 1 and Fig. 2,3) are found to stabilize the whole packing structure of the title compound. As shown in Fig.2, each one O2-containing molecule is surrounded by four O1-containing ones through H-bonding interactions.For the background to the title compound and its derivatives, see Mahiuddin et al. (2007); Namrata et al. (2012); Zhang et al. (2012); For hydrogen bonding, see: Desiraju (1995).
Data collection: APEX2 (Bruker 2007); cell
APEX2 and SAINT (Bruker 2007); data reduction: SAINT (Bruker 2007); 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) and PLATON (Spek, 2009).C20H23N3O | Z = 4 |
Mr = 321.41 | F(000) = 688 |
Triclinic, P1 | Dx = 1.192 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 10.2028 (7) Å | Cell parameters from 362 reflections |
b = 11.9126 (9) Å | θ = 2.0–25.0° |
c = 17.0553 (17) Å | µ = 0.08 mm−1 |
α = 101.563 (4)° | T = 296 K |
β = 99.110 (4)° | Block, colorless |
γ = 113.808 (2)° | 0.41 × 0.30 × 0.20 mm |
V = 1790.6 (3) Å3 |
Bruker APEXII CCD area-detector diffractometer | 6081 independent reflections |
Radiation source: fine-focus sealed tube | 4250 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.029 |
ω scans | θmax = 25.0°, θmin = 2.0° |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | h = −11→12 |
Tmin = 0.670, Tmax = 0.746 | k = −14→13 |
17517 measured reflections | l = −17→20 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.049 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.155 | w = 1/[σ2(Fo2) + (0.0753P)2 + 0.4342P] P = (Fo2 + 2Fc2)/3 |
S = 1.08 | (Δ/σ)max < 0.001 |
6081 reflections | Δρmax = 0.37 e Å−3 |
450 parameters | Δρmin = −0.30 e Å−3 |
46 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0088 (17) |
C20H23N3O | γ = 113.808 (2)° |
Mr = 321.41 | V = 1790.6 (3) Å3 |
Triclinic, P1 | Z = 4 |
a = 10.2028 (7) Å | Mo Kα radiation |
b = 11.9126 (9) Å | µ = 0.08 mm−1 |
c = 17.0553 (17) Å | T = 296 K |
α = 101.563 (4)° | 0.41 × 0.30 × 0.20 mm |
β = 99.110 (4)° |
Bruker APEXII CCD area-detector diffractometer | 6081 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2007) | 4250 reflections with I > 2σ(I) |
Tmin = 0.670, Tmax = 0.746 | Rint = 0.029 |
17517 measured reflections |
R[F2 > 2σ(F2)] = 0.049 | 46 restraints |
wR(F2) = 0.155 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.08 | Δρmax = 0.37 e Å−3 |
6081 reflections | Δρmin = −0.30 e Å−3 |
450 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 | ||
H1 | 0.7674 (19) | 1.1106 (15) | 0.1249 (14) | 0.060 (7)* | |
H4 | −0.2645 (15) | 0.1827 (16) | −0.1485 (14) | 0.055 (7)* | |
H5 | 0.2616 (18) | 0.460 (2) | 0.2126 (15) | 0.069 (8)* | |
H6 | 0.7939 (19) | 0.598 (2) | 0.2321 (15) | 0.066 (8)* | |
C1 | 0.3195 (3) | 1.2092 (3) | 0.08894 (19) | 0.0728 (8) | |
H1A | 0.2239 | 1.1948 | 0.0974 | 0.109* | |
H1B | 0.3159 | 1.2026 | 0.0315 | 0.109* | |
H1C | 0.3927 | 1.2932 | 0.1227 | 0.109* | |
C2 | 0.3606 (3) | 1.1097 (3) | 0.1127 (2) | 0.0710 (8) | |
H2A | 0.3619 | 1.1157 | 0.1704 | 0.085* | |
H2B | 0.2848 | 1.0250 | 0.0793 | 0.085* | |
C3 | 0.5086 (3) | 1.1247 (2) | 0.10119 (15) | 0.0503 (6) | |
H3A | 0.5067 | 1.1194 | 0.0435 | 0.060* | |
H3B | 0.5836 | 1.2098 | 0.1345 | 0.060* | |
C4 | 0.5540 (2) | 1.02936 (19) | 0.12349 (13) | 0.0427 (5) | |
C5 | 0.7011 (2) | 0.93810 (19) | 0.14869 (13) | 0.0407 (5) | |
C6 | 0.8141 (2) | 0.9008 (2) | 0.15921 (14) | 0.0473 (5) | |
C7 | 0.7821 (2) | 0.7941 (2) | 0.18722 (14) | 0.0481 (5) | |
H7A | 0.8550 | 0.7666 | 0.1963 | 0.058* | |
C8 | 0.6452 (2) | 0.72490 (19) | 0.20267 (13) | 0.0416 (5) | |
C9 | 0.5340 (2) | 0.76211 (19) | 0.18845 (13) | 0.0426 (5) | |
H9A | 0.4420 | 0.7163 | 0.1972 | 0.051* | |
C10 | 0.5623 (2) | 0.86912 (19) | 0.16083 (13) | 0.0403 (5) | |
C11 | 0.9585 (3) | 0.9701 (3) | 0.1396 (2) | 0.0711 (8) | |
H11A | 1.0215 | 0.9301 | 0.1511 | 0.107* | |
H11B | 1.0068 | 1.0580 | 0.1731 | 0.107* | |
H11C | 0.9398 | 0.9664 | 0.0819 | 0.107* | |
C12 | 0.6116 (2) | 0.6129 (2) | 0.23587 (13) | 0.0437 (5) | |
C13 | 0.6911 (3) | 0.4712 (2) | 0.29015 (16) | 0.0601 (6) | |
H13A | 0.6338 | 0.3898 | 0.2472 | 0.072* | |
H13B | 0.6322 | 0.4768 | 0.3288 | 0.072* | |
C14 | 0.8298 (3) | 0.4735 (3) | 0.33495 (18) | 0.0699 (7) | |
H14A | 0.8900 | 0.5560 | 0.3765 | 0.084* | |
H14B | 0.8866 | 0.4625 | 0.2961 | 0.084* | |
C15 | 0.7950 (3) | 0.3686 (3) | 0.37630 (15) | 0.0579 (6) | |
C16 | 0.7603 (3) | 0.2458 (3) | 0.33270 (16) | 0.0689 (7) | |
H16A | 0.7644 | 0.2289 | 0.2777 | 0.083* | |
C17 | 0.7198 (4) | 0.1472 (3) | 0.3681 (2) | 0.0823 (9) | |
H17A | 0.6971 | 0.0649 | 0.3371 | 0.099* | |
C18 | 0.7128 (4) | 0.1698 (4) | 0.4486 (2) | 0.0923 (10) | |
H18A | 0.6830 | 0.1031 | 0.4725 | 0.111* | |
C19 | 0.7503 (5) | 0.2916 (4) | 0.4931 (2) | 0.1045 (12) | |
H19A | 0.7494 | 0.3084 | 0.5486 | 0.125* | |
C20 | 0.7896 (4) | 0.3905 (3) | 0.45784 (18) | 0.0886 (10) | |
H20A | 0.8127 | 0.4727 | 0.4892 | 0.106* | |
C21 | −0.2363 (7) | 0.0418 (5) | −0.3386 (3) | 0.187 (3) | |
H21A | −0.3117 | −0.0448 | −0.3650 | 0.281* | |
H21B | −0.1802 | 0.0466 | −0.2861 | 0.281* | |
H21C | −0.1711 | 0.0675 | −0.3734 | 0.281* | |
C22 | −0.3053 (4) | 0.1261 (3) | −0.32530 (19) | 0.0923 (10) | |
H22A | −0.3727 | 0.0981 | −0.2912 | 0.111* | |
H22B | −0.3637 | 0.1189 | −0.3784 | 0.111* | |
C23 | −0.1962 (3) | 0.2635 (2) | −0.28424 (14) | 0.0564 (6) | |
H23A | −0.1253 | 0.2884 | −0.3168 | 0.068* | |
H23B | −0.2494 | 0.3149 | −0.2863 | 0.068* | |
C24 | −0.1116 (2) | 0.2973 (2) | −0.19662 (13) | 0.0444 (5) | |
C25 | 0.0603 (2) | 0.38852 (19) | −0.08105 (12) | 0.0388 (5) | |
C26 | −0.0660 (2) | 0.30365 (19) | −0.06467 (12) | 0.0381 (5) | |
C27 | −0.0696 (2) | 0.28931 (19) | 0.01351 (13) | 0.0412 (5) | |
H27A | −0.1556 | 0.2326 | 0.0231 | 0.049* | |
C28 | 0.0598 (2) | 0.36249 (18) | 0.07695 (12) | 0.0382 (5) | |
C29 | 0.1881 (2) | 0.44721 (19) | 0.06003 (13) | 0.0421 (5) | |
H29A | 0.2743 | 0.4948 | 0.1034 | 0.050* | |
C30 | 0.1921 (2) | 0.46316 (19) | −0.01772 (13) | 0.0427 (5) | |
C31 | 0.3295 (3) | 0.5560 (2) | −0.03364 (15) | 0.0644 (7) | |
H31A | 0.4081 | 0.5978 | 0.0169 | 0.097* | |
H31B | 0.3093 | 0.6190 | −0.0532 | 0.097* | |
H31C | 0.3589 | 0.5105 | −0.0748 | 0.097* | |
C32 | 0.0549 (2) | 0.34704 (19) | 0.16112 (13) | 0.0420 (5) | |
C33 | 0.1868 (3) | 0.3983 (2) | 0.30617 (14) | 0.0545 (6) | |
H33A | 0.0883 | 0.3677 | 0.3150 | 0.065* | |
H33B | 0.2496 | 0.4812 | 0.3469 | 0.065* | |
C34 | 0.2479 (4) | 0.3063 (3) | 0.31926 (17) | 0.0765 (8) | |
H34A | 0.3500 | 0.3417 | 0.3158 | 0.092* | |
H34B | 0.1915 | 0.2267 | 0.2746 | 0.092* | |
C35 | 0.2442 (3) | 0.2766 (3) | 0.40085 (16) | 0.0652 (7) | |
C36 | 0.1137 (4) | 0.2081 (4) | 0.4166 (2) | 0.0960 (10) | |
H36A | 0.0252 | 0.1813 | 0.3768 | 0.115* | |
C37 | 0.1083 (6) | 0.1767 (4) | 0.4904 (3) | 0.1156 (13) | |
H37A | 0.0175 | 0.1301 | 0.5001 | 0.139* | |
C38 | 0.2369 (7) | 0.2147 (4) | 0.5481 (2) | 0.1115 (13) | |
H38A | 0.2346 | 0.1926 | 0.5974 | 0.134* | |
C39 | 0.3665 (6) | 0.2835 (4) | 0.5348 (2) | 0.1176 (14) | |
H39A | 0.4544 | 0.3102 | 0.5751 | 0.141* | |
C40 | 0.3712 (4) | 0.3158 (3) | 0.4614 (2) | 0.0939 (10) | |
H40A | 0.4626 | 0.3650 | 0.4532 | 0.113* | |
N1 | 0.6923 (2) | 1.03909 (17) | 0.12434 (11) | 0.0445 (4) | |
N2 | 0.47131 (19) | 0.92760 (16) | 0.14350 (11) | 0.0444 (4) | |
N3 | 0.02963 (19) | 0.38310 (16) | −0.16468 (10) | 0.0438 (4) | |
N4 | −0.1741 (2) | 0.24659 (17) | −0.13948 (11) | 0.0439 (4) | |
N5 | 0.1783 (2) | 0.41362 (19) | 0.22348 (11) | 0.0506 (5) | |
N6 | 0.7166 (2) | 0.57415 (18) | 0.25232 (12) | 0.0502 (5) | |
O1 | 0.49045 (17) | 0.55903 (16) | 0.25059 (10) | 0.0586 (4) | |
O2 | −0.06237 (17) | 0.27366 (15) | 0.17288 (9) | 0.0585 (5) |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0683 (18) | 0.0739 (18) | 0.096 (2) | 0.0448 (15) | 0.0272 (16) | 0.0343 (16) |
C2 | 0.0631 (18) | 0.0694 (17) | 0.103 (2) | 0.0387 (15) | 0.0372 (16) | 0.0397 (16) |
C3 | 0.0488 (14) | 0.0447 (12) | 0.0580 (14) | 0.0199 (11) | 0.0156 (11) | 0.0174 (11) |
C4 | 0.0361 (12) | 0.0379 (11) | 0.0478 (13) | 0.0112 (9) | 0.0117 (10) | 0.0109 (9) |
C5 | 0.0345 (12) | 0.0382 (11) | 0.0448 (12) | 0.0116 (9) | 0.0126 (9) | 0.0114 (9) |
C6 | 0.0345 (12) | 0.0491 (13) | 0.0573 (14) | 0.0158 (10) | 0.0168 (10) | 0.0163 (11) |
C7 | 0.0363 (12) | 0.0501 (13) | 0.0616 (14) | 0.0206 (10) | 0.0155 (11) | 0.0195 (11) |
C8 | 0.0350 (12) | 0.0423 (11) | 0.0434 (12) | 0.0142 (10) | 0.0108 (9) | 0.0108 (9) |
C9 | 0.0323 (11) | 0.0403 (11) | 0.0486 (13) | 0.0102 (9) | 0.0121 (9) | 0.0115 (10) |
C10 | 0.0314 (11) | 0.0398 (11) | 0.0444 (12) | 0.0126 (9) | 0.0100 (9) | 0.0091 (9) |
C11 | 0.0452 (15) | 0.0715 (17) | 0.112 (2) | 0.0267 (13) | 0.0388 (15) | 0.0443 (16) |
C12 | 0.0375 (13) | 0.0449 (12) | 0.0429 (12) | 0.0142 (10) | 0.0098 (10) | 0.0109 (10) |
C13 | 0.0540 (16) | 0.0580 (15) | 0.0710 (17) | 0.0239 (12) | 0.0123 (13) | 0.0305 (13) |
C14 | 0.0584 (17) | 0.0790 (18) | 0.0801 (19) | 0.0301 (15) | 0.0177 (14) | 0.0418 (15) |
C15 | 0.0525 (15) | 0.0703 (17) | 0.0542 (15) | 0.0282 (13) | 0.0100 (12) | 0.0270 (13) |
C16 | 0.0774 (19) | 0.0803 (19) | 0.0532 (16) | 0.0353 (16) | 0.0220 (14) | 0.0254 (14) |
C17 | 0.094 (2) | 0.0694 (18) | 0.081 (2) | 0.0336 (17) | 0.0212 (18) | 0.0268 (16) |
C18 | 0.106 (3) | 0.100 (3) | 0.093 (3) | 0.048 (2) | 0.037 (2) | 0.061 (2) |
C19 | 0.160 (4) | 0.121 (3) | 0.061 (2) | 0.075 (3) | 0.044 (2) | 0.047 (2) |
C20 | 0.132 (3) | 0.088 (2) | 0.0579 (18) | 0.060 (2) | 0.0217 (18) | 0.0249 (16) |
C21 | 0.290 (8) | 0.157 (4) | 0.116 (4) | 0.163 (5) | −0.035 (4) | −0.024 (3) |
C22 | 0.107 (3) | 0.084 (2) | 0.0583 (18) | 0.024 (2) | 0.0059 (17) | 0.0165 (16) |
C23 | 0.0521 (15) | 0.0667 (16) | 0.0455 (14) | 0.0215 (13) | 0.0105 (11) | 0.0195 (12) |
C24 | 0.0408 (13) | 0.0484 (12) | 0.0463 (13) | 0.0195 (11) | 0.0152 (10) | 0.0168 (10) |
C25 | 0.0373 (12) | 0.0401 (11) | 0.0453 (12) | 0.0186 (10) | 0.0178 (10) | 0.0171 (9) |
C26 | 0.0308 (11) | 0.0402 (11) | 0.0423 (12) | 0.0142 (9) | 0.0103 (9) | 0.0132 (9) |
C27 | 0.0331 (12) | 0.0430 (11) | 0.0480 (13) | 0.0137 (10) | 0.0158 (10) | 0.0179 (10) |
C28 | 0.0372 (12) | 0.0366 (10) | 0.0426 (12) | 0.0154 (9) | 0.0144 (10) | 0.0150 (9) |
C29 | 0.0344 (12) | 0.0400 (11) | 0.0446 (12) | 0.0102 (9) | 0.0108 (9) | 0.0116 (9) |
C30 | 0.0348 (12) | 0.0406 (11) | 0.0476 (13) | 0.0101 (10) | 0.0153 (10) | 0.0135 (10) |
C31 | 0.0487 (15) | 0.0639 (15) | 0.0549 (15) | −0.0010 (12) | 0.0177 (12) | 0.0186 (12) |
C32 | 0.0396 (13) | 0.0395 (11) | 0.0446 (12) | 0.0140 (10) | 0.0143 (10) | 0.0131 (10) |
C33 | 0.0585 (15) | 0.0595 (14) | 0.0436 (13) | 0.0230 (12) | 0.0143 (11) | 0.0179 (11) |
C34 | 0.098 (2) | 0.090 (2) | 0.0664 (17) | 0.0549 (18) | 0.0341 (16) | 0.0359 (15) |
C35 | 0.082 (2) | 0.0677 (16) | 0.0573 (16) | 0.0396 (15) | 0.0214 (15) | 0.0258 (13) |
C36 | 0.091 (2) | 0.123 (3) | 0.095 (2) | 0.051 (2) | 0.0331 (19) | 0.064 (2) |
C37 | 0.133 (3) | 0.136 (3) | 0.118 (3) | 0.069 (3) | 0.068 (3) | 0.074 (3) |
C38 | 0.171 (4) | 0.109 (3) | 0.068 (2) | 0.069 (3) | 0.039 (3) | 0.036 (2) |
C39 | 0.132 (4) | 0.116 (3) | 0.068 (2) | 0.040 (3) | −0.014 (2) | 0.017 (2) |
C40 | 0.090 (2) | 0.091 (2) | 0.077 (2) | 0.0233 (19) | 0.0057 (18) | 0.0263 (18) |
N1 | 0.0353 (11) | 0.0393 (10) | 0.0570 (11) | 0.0118 (8) | 0.0165 (9) | 0.0175 (9) |
N2 | 0.0345 (10) | 0.0428 (10) | 0.0552 (11) | 0.0156 (8) | 0.0128 (8) | 0.0159 (8) |
N3 | 0.0399 (11) | 0.0485 (10) | 0.0434 (10) | 0.0167 (9) | 0.0154 (8) | 0.0178 (8) |
N4 | 0.0312 (10) | 0.0492 (11) | 0.0459 (11) | 0.0112 (9) | 0.0117 (9) | 0.0168 (9) |
N5 | 0.0405 (12) | 0.0593 (12) | 0.0432 (11) | 0.0121 (10) | 0.0124 (9) | 0.0186 (9) |
N6 | 0.0462 (12) | 0.0554 (11) | 0.0574 (12) | 0.0239 (10) | 0.0200 (10) | 0.0267 (9) |
O1 | 0.0395 (9) | 0.0636 (10) | 0.0750 (11) | 0.0172 (8) | 0.0192 (8) | 0.0349 (9) |
O2 | 0.0475 (10) | 0.0584 (10) | 0.0510 (10) | 0.0025 (8) | 0.0183 (8) | 0.0197 (8) |
C1—C2 | 1.511 (4) | C21—H21B | 0.9600 |
C1—H1A | 0.9600 | C21—H21C | 0.9600 |
C1—H1B | 0.9600 | C22—C23 | 1.494 (4) |
C1—H1C | 0.9600 | C22—H22A | 0.9700 |
C2—C3 | 1.498 (3) | C22—H22B | 0.9700 |
C2—H2A | 0.9700 | C23—C24 | 1.487 (3) |
C2—H2B | 0.9700 | C23—H23A | 0.9700 |
C3—C4 | 1.481 (3) | C23—H23B | 0.9700 |
C3—H3A | 0.9700 | C24—N3 | 1.326 (3) |
C3—H3B | 0.9700 | C24—N4 | 1.357 (3) |
C4—N2 | 1.315 (3) | C25—C26 | 1.392 (3) |
C4—N1 | 1.366 (3) | C25—N3 | 1.394 (3) |
C5—N1 | 1.380 (3) | C25—C30 | 1.399 (3) |
C5—C6 | 1.393 (3) | C26—N4 | 1.381 (3) |
C5—C10 | 1.395 (3) | C26—C27 | 1.382 (3) |
C6—C7 | 1.382 (3) | C27—C28 | 1.383 (3) |
C6—C11 | 1.500 (3) | C27—H27A | 0.9300 |
C7—C8 | 1.406 (3) | C28—C29 | 1.408 (3) |
C7—H7A | 0.9300 | C28—C32 | 1.490 (3) |
C8—C9 | 1.380 (3) | C29—C30 | 1.381 (3) |
C8—C12 | 1.488 (3) | C29—H29A | 0.9300 |
C9—C10 | 1.385 (3) | C30—C31 | 1.500 (3) |
C9—H9A | 0.9300 | C31—H31A | 0.9600 |
C10—N2 | 1.397 (3) | C31—H31B | 0.9600 |
C11—H11A | 0.9600 | C31—H31C | 0.9600 |
C11—H11B | 0.9600 | C32—O2 | 1.240 (2) |
C11—H11C | 0.9600 | C32—N5 | 1.333 (3) |
C12—O1 | 1.235 (2) | C33—N5 | 1.451 (3) |
C12—N6 | 1.340 (3) | C33—C34 | 1.499 (4) |
C13—N6 | 1.449 (3) | C33—H33A | 0.9700 |
C13—C14 | 1.486 (3) | C33—H33B | 0.9700 |
C13—H13A | 0.9700 | C34—C35 | 1.505 (4) |
C13—H13B | 0.9700 | C34—H34A | 0.9700 |
C14—C15 | 1.503 (3) | C34—H34B | 0.9700 |
C14—H14A | 0.9700 | C35—C36 | 1.355 (4) |
C14—H14B | 0.9700 | C35—C40 | 1.363 (4) |
C15—C16 | 1.371 (4) | C36—C37 | 1.386 (5) |
C15—C20 | 1.377 (4) | C36—H36A | 0.9300 |
C16—C17 | 1.373 (4) | C37—C38 | 1.352 (6) |
C16—H16A | 0.9300 | C37—H37A | 0.9300 |
C17—C18 | 1.364 (4) | C38—C39 | 1.329 (6) |
C17—H17A | 0.9300 | C38—H38A | 0.9300 |
C18—C19 | 1.359 (5) | C39—C40 | 1.385 (5) |
C18—H18A | 0.9300 | C39—H39A | 0.9300 |
C19—C20 | 1.375 (4) | C40—H40A | 0.9300 |
C19—H19A | 0.9300 | N1—H1 | 0.883 (10) |
C20—H20A | 0.9300 | N4—H4 | 0.892 (10) |
C21—C22 | 1.444 (6) | N5—H5 | 0.879 (10) |
C21—H21A | 0.9600 | N6—H6 | 0.875 (10) |
C2—C1—H1A | 109.5 | C21—C22—H22A | 108.9 |
C2—C1—H1B | 109.5 | C23—C22—H22A | 108.9 |
H1A—C1—H1B | 109.5 | C21—C22—H22B | 108.9 |
C2—C1—H1C | 109.5 | C23—C22—H22B | 108.9 |
H1A—C1—H1C | 109.5 | H22A—C22—H22B | 107.7 |
H1B—C1—H1C | 109.5 | C24—C23—C22 | 117.0 (2) |
C3—C2—C1 | 113.1 (2) | C24—C23—H23A | 108.0 |
C3—C2—H2A | 109.0 | C22—C23—H23A | 108.0 |
C1—C2—H2A | 109.0 | C24—C23—H23B | 108.0 |
C3—C2—H2B | 109.0 | C22—C23—H23B | 108.0 |
C1—C2—H2B | 109.0 | H23A—C23—H23B | 107.3 |
H2A—C2—H2B | 107.8 | N3—C24—N4 | 112.61 (19) |
C4—C3—C2 | 115.24 (19) | N3—C24—C23 | 124.40 (19) |
C4—C3—H3A | 108.5 | N4—C24—C23 | 122.9 (2) |
C2—C3—H3A | 108.5 | C26—C25—N3 | 109.70 (18) |
C4—C3—H3B | 108.5 | C26—C25—C30 | 120.55 (18) |
C2—C3—H3B | 108.5 | N3—C25—C30 | 129.74 (18) |
H3A—C3—H3B | 107.5 | N4—C26—C27 | 131.64 (18) |
N2—C4—N1 | 112.09 (19) | N4—C26—C25 | 105.57 (17) |
N2—C4—C3 | 126.25 (19) | C27—C26—C25 | 122.78 (19) |
N1—C4—C3 | 121.65 (19) | C26—C27—C28 | 117.46 (18) |
N1—C5—C6 | 132.18 (19) | C26—C27—H27A | 121.3 |
N1—C5—C10 | 105.01 (18) | C28—C27—H27A | 121.3 |
C6—C5—C10 | 122.79 (19) | C27—C28—C29 | 119.67 (19) |
C7—C6—C5 | 115.18 (19) | C27—C28—C32 | 117.12 (18) |
C7—C6—C11 | 122.6 (2) | C29—C28—C32 | 123.21 (19) |
C5—C6—C11 | 122.2 (2) | C30—C29—C28 | 123.3 (2) |
C6—C7—C8 | 123.4 (2) | C30—C29—H29A | 118.4 |
C6—C7—H7A | 118.3 | C28—C29—H29A | 118.4 |
C8—C7—H7A | 118.3 | C29—C30—C25 | 116.26 (18) |
C9—C8—C7 | 119.63 (19) | C29—C30—C31 | 122.2 (2) |
C9—C8—C12 | 116.51 (19) | C25—C30—C31 | 121.58 (19) |
C7—C8—C12 | 123.85 (19) | C30—C31—H31A | 109.5 |
C8—C9—C10 | 118.61 (19) | C30—C31—H31B | 109.5 |
C8—C9—H9A | 120.7 | H31A—C31—H31B | 109.5 |
C10—C9—H9A | 120.7 | C30—C31—H31C | 109.5 |
C9—C10—C5 | 120.31 (19) | H31A—C31—H31C | 109.5 |
C9—C10—N2 | 129.93 (19) | H31B—C31—H31C | 109.5 |
C5—C10—N2 | 109.74 (18) | O2—C32—N5 | 120.66 (19) |
C6—C11—H11A | 109.5 | O2—C32—C28 | 120.42 (19) |
C6—C11—H11B | 109.5 | N5—C32—C28 | 118.92 (18) |
H11A—C11—H11B | 109.5 | N5—C33—C34 | 112.4 (2) |
C6—C11—H11C | 109.5 | N5—C33—H33A | 109.1 |
H11A—C11—H11C | 109.5 | C34—C33—H33A | 109.1 |
H11B—C11—H11C | 109.5 | N5—C33—H33B | 109.1 |
O1—C12—N6 | 120.5 (2) | C34—C33—H33B | 109.1 |
O1—C12—C8 | 120.5 (2) | H33A—C33—H33B | 107.9 |
N6—C12—C8 | 119.02 (19) | C33—C34—C35 | 114.4 (2) |
N6—C13—C14 | 113.7 (2) | C33—C34—H34A | 108.7 |
N6—C13—H13A | 108.8 | C35—C34—H34A | 108.7 |
C14—C13—H13A | 108.8 | C33—C34—H34B | 108.7 |
N6—C13—H13B | 108.8 | C35—C34—H34B | 108.7 |
C14—C13—H13B | 108.8 | H34A—C34—H34B | 107.6 |
H13A—C13—H13B | 107.7 | C36—C35—C40 | 117.3 (3) |
C13—C14—C15 | 110.8 (2) | C36—C35—C34 | 121.0 (3) |
C13—C14—H14A | 109.5 | C40—C35—C34 | 121.7 (3) |
C15—C14—H14A | 109.5 | C35—C36—C37 | 121.8 (4) |
C13—C14—H14B | 109.5 | C35—C36—H36A | 119.1 |
C15—C14—H14B | 109.5 | C37—C36—H36A | 119.1 |
H14A—C14—H14B | 108.1 | C38—C37—C36 | 119.2 (4) |
C16—C15—C20 | 117.6 (2) | C38—C37—H37A | 120.4 |
C16—C15—C14 | 120.9 (2) | C36—C37—H37A | 120.4 |
C20—C15—C14 | 121.5 (3) | C39—C38—C37 | 120.2 (4) |
C15—C16—C17 | 121.7 (3) | C39—C38—H38A | 119.9 |
C15—C16—H16A | 119.1 | C37—C38—H38A | 119.9 |
C17—C16—H16A | 119.1 | C38—C39—C40 | 120.4 (4) |
C18—C17—C16 | 120.1 (3) | C38—C39—H39A | 119.8 |
C18—C17—H17A | 119.9 | C40—C39—H39A | 119.8 |
C16—C17—H17A | 119.9 | C35—C40—C39 | 121.1 (4) |
C19—C18—C17 | 118.7 (3) | C35—C40—H40A | 119.5 |
C19—C18—H18A | 120.6 | C39—C40—H40A | 119.5 |
C17—C18—H18A | 120.6 | C4—N1—C5 | 107.75 (17) |
C18—C19—C20 | 121.4 (3) | C4—N1—H1 | 122.7 (16) |
C18—C19—H19A | 119.3 | C5—N1—H1 | 126.8 (16) |
C20—C19—H19A | 119.3 | C4—N2—C10 | 105.38 (17) |
C19—C20—C15 | 120.4 (3) | C24—N3—C25 | 104.92 (16) |
C19—C20—H20A | 119.8 | C24—N4—C26 | 107.21 (17) |
C15—C20—H20A | 119.8 | C24—N4—H4 | 127.3 (15) |
C22—C21—H21A | 109.5 | C26—N4—H4 | 125.2 (15) |
C22—C21—H21B | 109.5 | C32—N5—C33 | 122.83 (19) |
H21A—C21—H21B | 109.5 | C32—N5—H5 | 118.8 (17) |
C22—C21—H21C | 109.5 | C33—N5—H5 | 117.7 (17) |
H21A—C21—H21C | 109.5 | C12—N6—C13 | 120.33 (19) |
H21B—C21—H21C | 109.5 | C12—N6—H6 | 121.9 (17) |
C21—C22—C23 | 113.4 (4) | C13—N6—H6 | 116.7 (17) |
C1—C2—C3—C4 | −179.9 (2) | C27—C28—C29—C30 | 0.8 (3) |
C2—C3—C4—N2 | 7.6 (3) | C32—C28—C29—C30 | −178.92 (19) |
C2—C3—C4—N1 | −173.1 (2) | C28—C29—C30—C25 | −0.7 (3) |
N1—C5—C6—C7 | 178.2 (2) | C28—C29—C30—C31 | 178.8 (2) |
C10—C5—C6—C7 | −3.5 (3) | C26—C25—C30—C29 | −0.1 (3) |
N1—C5—C6—C11 | −3.2 (4) | N3—C25—C30—C29 | 179.91 (19) |
C10—C5—C6—C11 | 175.1 (2) | C26—C25—C30—C31 | −179.6 (2) |
C5—C6—C7—C8 | 1.3 (3) | N3—C25—C30—C31 | 0.4 (3) |
C11—C6—C7—C8 | −177.3 (2) | C27—C28—C32—O2 | −1.8 (3) |
C6—C7—C8—C9 | 1.1 (3) | C29—C28—C32—O2 | 177.9 (2) |
C6—C7—C8—C12 | −177.6 (2) | C27—C28—C32—N5 | 178.43 (19) |
C7—C8—C9—C10 | −1.4 (3) | C29—C28—C32—N5 | −1.9 (3) |
C12—C8—C9—C10 | 177.36 (18) | N5—C33—C34—C35 | −173.9 (2) |
C8—C9—C10—C5 | −0.7 (3) | C33—C34—C35—C36 | 68.7 (4) |
C8—C9—C10—N2 | −178.6 (2) | C33—C34—C35—C40 | −112.2 (3) |
N1—C5—C10—C9 | −177.99 (18) | C40—C35—C36—C37 | −1.1 (5) |
C6—C5—C10—C9 | 3.3 (3) | C34—C35—C36—C37 | 178.1 (3) |
N1—C5—C10—N2 | 0.3 (2) | C35—C36—C37—C38 | −0.4 (6) |
C6—C5—C10—N2 | −178.35 (19) | C36—C37—C38—C39 | 1.4 (7) |
C9—C8—C12—O1 | −1.1 (3) | C37—C38—C39—C40 | −0.7 (7) |
C7—C8—C12—O1 | 177.6 (2) | C36—C35—C40—C39 | 1.7 (5) |
C9—C8—C12—N6 | −178.74 (19) | C34—C35—C40—C39 | −177.5 (3) |
C7—C8—C12—N6 | 0.0 (3) | C38—C39—C40—C35 | −0.9 (6) |
N6—C13—C14—C15 | 177.0 (2) | N2—C4—N1—C5 | −1.6 (2) |
C13—C14—C15—C16 | 82.9 (3) | C3—C4—N1—C5 | 179.02 (19) |
C13—C14—C15—C20 | −93.9 (3) | C6—C5—N1—C4 | 179.2 (2) |
C20—C15—C16—C17 | 0.8 (4) | C10—C5—N1—C4 | 0.7 (2) |
C14—C15—C16—C17 | −176.1 (3) | N1—C4—N2—C10 | 1.8 (2) |
C15—C16—C17—C18 | 0.1 (5) | C3—C4—N2—C10 | −178.9 (2) |
C16—C17—C18—C19 | −1.7 (5) | C9—C10—N2—C4 | 176.8 (2) |
C17—C18—C19—C20 | 2.3 (6) | C5—C10—N2—C4 | −1.3 (2) |
C18—C19—C20—C15 | −1.4 (6) | N4—C24—N3—C25 | −0.2 (2) |
C16—C15—C20—C19 | −0.1 (5) | C23—C24—N3—C25 | 177.0 (2) |
C14—C15—C20—C19 | 176.8 (3) | C26—C25—N3—C24 | 0.2 (2) |
C21—C22—C23—C24 | −67.5 (4) | C30—C25—N3—C24 | −179.8 (2) |
C22—C23—C24—N3 | 142.9 (3) | N3—C24—N4—C26 | 0.2 (2) |
C22—C23—C24—N4 | −40.1 (3) | C23—C24—N4—C26 | −177.1 (2) |
N3—C25—C26—N4 | −0.1 (2) | C27—C26—N4—C24 | 179.0 (2) |
C30—C25—C26—N4 | 179.95 (18) | C25—C26—N4—C24 | −0.1 (2) |
N3—C25—C26—C27 | −179.21 (18) | O2—C32—N5—C33 | 4.5 (3) |
C30—C25—C26—C27 | 0.8 (3) | C28—C32—N5—C33 | −175.66 (19) |
N4—C26—C27—C28 | −179.6 (2) | C34—C33—N5—C32 | 95.4 (3) |
C25—C26—C27—C28 | −0.7 (3) | O1—C12—N6—C13 | −2.0 (3) |
C26—C27—C28—C29 | −0.1 (3) | C8—C12—N6—C13 | 175.6 (2) |
C26—C27—C28—C32 | 179.64 (17) | C14—C13—N6—C12 | −156.5 (2) |
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.88 | 1.91 | 2.744 (2) | 157 |
N4—H4···N2ii | 0.89 | 2.01 | 2.882 (3) | 165 |
N5—H5···O1 | 0.88 | 2.06 | 2.849 (4) | 148 |
N6—H6···N3iii | 0.88 | 2.25 | 3.109 (2) | 169 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | C20H23N3O |
Mr | 321.41 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 296 |
a, b, c (Å) | 10.2028 (7), 11.9126 (9), 17.0553 (17) |
α, β, γ (°) | 101.563 (4), 99.110 (4), 113.808 (2) |
V (Å3) | 1790.6 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.41 × 0.30 × 0.20 |
Data collection | |
Diffractometer | Bruker APEXII CCD area-detector |
Absorption correction | Multi-scan (SADABS; Bruker, 2007) |
Tmin, Tmax | 0.670, 0.746 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 17517, 6081, 4250 |
Rint | 0.029 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.049, 0.155, 1.08 |
No. of reflections | 6081 |
No. of parameters | 450 |
No. of restraints | 46 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.37, −0.30 |
Computer programs: APEX2 (Bruker 2007), APEX2 and SAINT (Bruker 2007), SAINT (Bruker 2007), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N1—H1···O2i | 0.884 | 1.91 | 2.744 (2) | 156.70 |
N4—H4···N2ii | 0.892 | 2.01 | 2.882 (3) | 164.50 |
N5—H5···O1 | 0.879 | 2.06 | 2.849 (4) | 148.37 |
N6—H6···N3iii | 0.875 | 2.25 | 3.109 (2) | 168.50 |
Symmetry codes: (i) x+1, y+1, z; (ii) −x, −y+1, −z; (iii) −x+1, −y+1, −z. |
Acknowledgements
This work was supported by the National Technological Project for the Manufacture and Innovation of Key New Drugs (2009ZX09103-143).
References
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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.
Benzimidazole is an important scaffold with biological activities generally ultilized in antihypertensive drugs, proton pump inhibitors and antimicrobial agents, etc. (Mahiuddin et al., 2007.; Namrata et al., 2012). As a part of our study of 6-substituted carbamoyl benzimidazoles as a nonpeptidic angiotensin II AT1 receptor antagonist (Zhang et al., 2012), herein we report the synthesis and crystal structure of the title compound of this family. In the asymmetric unit of the title compound, there are two independent molecules with different dihedral angles between the phenyl ring of the phenylethylamino and the benzimidazole ring. In the O1(carbonyl)-containing molecule, the dihedral angle between the phenyl ring of the phenylethylamino and the benzimidazole ring is -1.8 (5) °, while the O2(carbonyl)-containing one has the value of -1.0 (5) ° (Fig. 1). Intermolecular N—H···O and N—H···N hydrogen-bonding (Desiraju, 1995) interactions (Table 1 and Fig. 2,3) are found to stabilize the whole packing structure of the title compound. As shown in Fig.2, each one O2-containing molecule is surrounded by four O1-containing ones through H-bonding interactions.