Literature DB >> 22719627

Ethyl 2-(4-chloro-phen-yl)-1-phenyl-1H-benzimidazole-5-carboxyl-ate.

Yeong Keng Yoon, Elumalai Manogaran, Tan Soo Choon, Suhana Arshad, Ibrahim Abdul Razak.   

Abstract

In the title compound, C(22)H(17)ClN(2)O(2), the essentially planar benzimidazole ring system [maximum deviation = 0.012 (2) Å] forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl and chloro-substituted benzene rings. The dihedral angle between the phenyl and benzene rings is 64.23 (8)°. In the crystal, mol-ecules are linked into a zigzag chain along the a axis by inter-molecular C-H⋯O hydrogen bonds. C-H⋯π inter-actions are also present.

Entities:  

Year:  2012        PMID： 22719627      PMCID： PMC3379429          DOI： 10.1107/S1600536812022192

Source DB:  PubMed          Journal:  Acta Crystallogr Sect E Struct Rep Online        ISSN： 1600-5368


Related literature

For applications of benzimidazoles, see: Tanious et al. (2004 ▶); Townsend & Revankar (1970 ▶). For related structures, see: Yoon et al. (2011 ▶, 2012 ▶); Kassim et al. (2012 ▶). For stability of the temperature controller used in the data collection, see: Cosier & Glazer (1986 ▶).

Experimental

Crystal data

C22H17ClN2O2 M = 376.83 Triclinic, a = 9.3357 (2) Å b = 9.7982 (2) Å c = 11.7718 (4) Å α = 107.502 (2)° β = 102.106 (2)° γ = 109.539 (1)° V = 908.31 (4) Å3 Z = 2 Mo Kα radiation μ = 0.23 mm−1 T = 100 K 0.38 × 0.29 × 0.24 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.917, T max = 0.946 18472 measured reflections 5326 independent reflections 4233 reflections with I > 2σ(I) R int = 0.033

Refinement

R[F 2 > 2σ(F 2)] = 0.048 wR(F 2) = 0.127 S = 1.04 5326 reflections 245 parameters H-atom parameters constrained Δρmax = 0.57 e Å−3 Δρmin = −0.31 e Å−3 Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶). Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812022192/is5137sup1.cif Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812022192/is5137Isup2.hkl Supplementary material file. DOI: 10.1107/S1600536812022192/is5137Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C22H17ClN2O2Z = 2
Mr = 376.83F(000) = 392
Triclinic, P1Dx = 1.378 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.3357 (2) ÅCell parameters from 7225 reflections
b = 9.7982 (2) Åθ = 2.6–30.2°
c = 11.7718 (4) ŵ = 0.23 mm−1
α = 107.502 (2)°T = 100 K
β = 102.106 (2)°Block, colourless
γ = 109.539 (1)°0.38 × 0.29 × 0.24 mm
V = 908.31 (4) Å3
Bruker SMART APEXII CCD area-detector diffractometer5326 independent reflections
Radiation source: fine-focus sealed tube4233 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.033
φ and ω scansθmax = 30.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2009)h = −13→13
Tmin = 0.917, Tmax = 0.946k = −13→13
18472 measured reflectionsl = −14→16
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.048Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.127H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0648P)2 + 0.3753P] where P = (Fo2 + 2Fc2)/3
5326 reflections(Δ/σ)max < 0.001
245 parametersΔρmax = 0.57 e Å−3
0 restraintsΔρmin = −0.31 e Å−3
Experimental. The crystal was placed in the cold stream of an Oxford Cryosystems Cobra open-flow nitrogen cryostat (Cosier & Glazer, 1986) operating at 100.0 (1) K.
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.
xyzUiso*/Ueq
Cl1−0.66895 (5)−0.31206 (5)−0.07003 (4)0.02705 (11)
O10.66316 (12)−0.10624 (12)0.40052 (10)0.0196 (2)
O20.84606 (13)0.14573 (13)0.46871 (11)0.0229 (2)
N10.11793 (15)−0.10887 (14)0.20878 (12)0.0173 (2)
N20.16095 (14)0.14100 (14)0.23348 (12)0.0158 (2)
C10.31182 (17)0.14553 (17)0.28366 (14)0.0165 (3)
C20.46660 (18)0.26942 (17)0.34187 (14)0.0190 (3)
H2A0.48480.37440.35200.023*
C30.59248 (18)0.23218 (18)0.38427 (15)0.0201 (3)
H3A0.69970.31360.42490.024*
C40.56507 (17)0.07571 (17)0.36849 (14)0.0179 (3)
C50.41041 (18)−0.04706 (17)0.31022 (14)0.0180 (3)
H5A0.3924−0.15210.29970.022*
C60.28203 (17)−0.01073 (17)0.26755 (13)0.0165 (3)
C70.04967 (17)−0.01571 (16)0.19011 (13)0.0159 (3)
C8−0.12637 (17)−0.07740 (17)0.12872 (13)0.0158 (3)
C9−0.22379 (18)−0.21369 (17)0.13982 (14)0.0178 (3)
H9A−0.1746−0.25850.18810.021*
C10−0.39041 (19)−0.28384 (18)0.08158 (14)0.0199 (3)
H10A−0.4559−0.37390.09190.024*
C11−0.46027 (18)−0.21990 (18)0.00743 (14)0.0192 (3)
C12−0.36672 (18)−0.08703 (18)−0.00704 (14)0.0186 (3)
H12A−0.4161−0.0458−0.05880.022*
C13−0.19981 (18)−0.01465 (17)0.05489 (13)0.0171 (3)
H13A−0.13540.07790.04700.021*
C140.13273 (17)0.27784 (17)0.23909 (13)0.0163 (3)
C150.04178 (18)0.32176 (18)0.31023 (14)0.0188 (3)
H15A−0.00400.26070.35340.023*
C160.01898 (19)0.45680 (19)0.31695 (15)0.0223 (3)
H16A−0.04170.48880.36610.027*
C170.0840 (2)0.54544 (18)0.25259 (16)0.0242 (3)
H17A0.06750.63740.25770.029*
C180.1728 (2)0.49899 (19)0.18094 (16)0.0246 (3)
H18A0.21610.55860.13600.029*
C190.19904 (19)0.36522 (18)0.17450 (14)0.0204 (3)
H19A0.26140.33430.12660.024*
C200.70739 (18)0.04619 (17)0.41852 (14)0.0171 (3)
C210.79321 (18)−0.14740 (18)0.44432 (14)0.0188 (3)
H21A0.8447−0.09280.53780.023*
H21B0.8767−0.11650.40560.023*
C220.7175 (2)−0.32370 (19)0.40427 (16)0.0254 (3)
H22A0.8013−0.35780.43170.038*
H22B0.6667−0.37590.31170.038*
H22C0.6354−0.35230.44330.038*
U11U22U33U12U13U23
Cl10.01444 (18)0.0278 (2)0.0327 (2)0.00672 (15)0.00290 (15)0.01040 (16)
O10.0137 (5)0.0191 (5)0.0244 (5)0.0072 (4)0.0042 (4)0.0082 (4)
O20.0151 (5)0.0228 (5)0.0280 (6)0.0061 (5)0.0055 (4)0.0100 (5)
N10.0149 (6)0.0164 (6)0.0196 (6)0.0061 (5)0.0041 (5)0.0077 (5)
N20.0141 (6)0.0151 (5)0.0192 (6)0.0060 (5)0.0063 (5)0.0079 (5)
C10.0151 (6)0.0175 (6)0.0181 (6)0.0073 (6)0.0064 (5)0.0081 (5)
C20.0180 (7)0.0154 (6)0.0228 (7)0.0060 (6)0.0073 (6)0.0078 (6)
C30.0152 (7)0.0189 (7)0.0237 (7)0.0049 (6)0.0067 (6)0.0082 (6)
C40.0152 (7)0.0201 (7)0.0187 (7)0.0073 (6)0.0056 (5)0.0084 (6)
C50.0169 (7)0.0170 (6)0.0206 (7)0.0074 (6)0.0064 (6)0.0080 (5)
C60.0155 (6)0.0163 (6)0.0173 (6)0.0062 (6)0.0059 (5)0.0067 (5)
C70.0163 (6)0.0150 (6)0.0156 (6)0.0057 (6)0.0053 (5)0.0064 (5)
C80.0144 (6)0.0159 (6)0.0152 (6)0.0062 (5)0.0042 (5)0.0045 (5)
C90.0177 (7)0.0179 (6)0.0172 (6)0.0069 (6)0.0057 (5)0.0073 (5)
C100.0190 (7)0.0202 (7)0.0194 (7)0.0066 (6)0.0076 (6)0.0080 (6)
C110.0140 (6)0.0224 (7)0.0180 (7)0.0076 (6)0.0047 (5)0.0048 (6)
C120.0182 (7)0.0217 (7)0.0177 (7)0.0114 (6)0.0058 (5)0.0071 (5)
C130.0183 (7)0.0170 (6)0.0176 (7)0.0082 (6)0.0072 (5)0.0075 (5)
C140.0161 (6)0.0151 (6)0.0169 (6)0.0065 (6)0.0040 (5)0.0066 (5)
C150.0172 (7)0.0196 (7)0.0190 (7)0.0074 (6)0.0058 (6)0.0076 (6)
C160.0189 (7)0.0221 (7)0.0254 (8)0.0111 (6)0.0068 (6)0.0067 (6)
C170.0225 (8)0.0173 (7)0.0295 (8)0.0094 (6)0.0027 (6)0.0086 (6)
C180.0305 (8)0.0183 (7)0.0253 (8)0.0089 (7)0.0084 (7)0.0119 (6)
C190.0240 (8)0.0191 (7)0.0202 (7)0.0092 (6)0.0099 (6)0.0090 (6)
C200.0154 (6)0.0198 (7)0.0181 (7)0.0078 (6)0.0081 (5)0.0083 (5)
C210.0154 (7)0.0219 (7)0.0198 (7)0.0097 (6)0.0049 (5)0.0081 (6)
C220.0282 (8)0.0247 (8)0.0256 (8)0.0139 (7)0.0083 (7)0.0110 (6)
Cl1—C111.7393 (15)C10—C111.394 (2)
O1—C201.3440 (17)C10—H10A0.9500
O1—C211.4466 (17)C11—C121.386 (2)
O2—C201.2101 (18)C12—C131.391 (2)
N1—C71.3186 (18)C12—H12A0.9500
N1—C61.3858 (19)C13—H13A0.9500
N2—C11.3885 (17)C14—C191.389 (2)
N2—C71.3916 (18)C14—C151.390 (2)
N2—C141.4359 (17)C15—C161.391 (2)
C1—C21.394 (2)C15—H15A0.9500
C1—C61.4057 (19)C16—C171.390 (2)
C2—C31.383 (2)C16—H16A0.9500
C2—H2A0.9500C17—C181.386 (2)
C3—C41.413 (2)C17—H17A0.9500
C3—H3A0.9500C18—C191.395 (2)
C4—C51.389 (2)C18—H18A0.9500
C4—C201.4923 (19)C19—H19A0.9500
C5—C61.3985 (19)C21—C221.503 (2)
C5—H5A0.9500C21—H21A0.9900
C7—C81.471 (2)C21—H21B0.9900
C8—C131.3990 (19)C22—H22A0.9800
C8—C91.403 (2)C22—H22B0.9800
C9—C101.384 (2)C22—H22C0.9800
C9—H9A0.9500
C20—O1—C21115.83 (11)C11—C12—H12A120.3
C7—N1—C6105.12 (12)C13—C12—H12A120.3
C1—N2—C7106.08 (11)C12—C13—C8120.38 (14)
C1—N2—C14124.39 (12)C12—C13—H13A119.8
C7—N2—C14129.30 (12)C8—C13—H13A119.8
N2—C1—C2131.98 (13)C19—C14—C15121.23 (13)
N2—C1—C6105.41 (12)C19—C14—N2119.15 (13)
C2—C1—C6122.60 (13)C15—C14—N2119.61 (13)
C3—C2—C1116.80 (13)C14—C15—C16118.77 (14)
C3—C2—H2A121.6C14—C15—H15A120.6
C1—C2—H2A121.6C16—C15—H15A120.6
C2—C3—C4121.44 (14)C17—C16—C15120.81 (14)
C2—C3—H3A119.3C17—C16—H16A119.6
C4—C3—H3A119.3C15—C16—H16A119.6
C5—C4—C3121.36 (13)C18—C17—C16119.67 (14)
C5—C4—C20120.65 (13)C18—C17—H17A120.2
C3—C4—C20117.98 (13)C16—C17—H17A120.2
C4—C5—C6117.73 (13)C17—C18—C19120.38 (15)
C4—C5—H5A121.1C17—C18—H18A119.8
C6—C5—H5A121.1C19—C18—H18A119.8
N1—C6—C5129.46 (13)C14—C19—C18119.13 (14)
N1—C6—C1110.46 (12)C14—C19—H19A120.4
C5—C6—C1120.07 (13)C18—C19—H19A120.4
N1—C7—N2112.93 (12)O2—C20—O1123.55 (13)
N1—C7—C8121.50 (13)O2—C20—C4124.85 (13)
N2—C7—C8125.57 (12)O1—C20—C4111.60 (12)
C13—C8—C9118.95 (13)O1—C21—C22106.27 (12)
C13—C8—C7124.14 (13)O1—C21—H21A110.5
C9—C8—C7116.79 (12)C22—C21—H21A110.5
C10—C9—C8121.07 (13)O1—C21—H21B110.5
C10—C9—H9A119.5C22—C21—H21B110.5
C8—C9—H9A119.5H21A—C21—H21B108.7
C9—C10—C11118.76 (14)C21—C22—H22A109.5
C9—C10—H10A120.6C21—C22—H22B109.5
C11—C10—H10A120.6H22A—C22—H22B109.5
C12—C11—C10121.37 (14)C21—C22—H22C109.5
C12—C11—Cl1119.89 (11)H22A—C22—H22C109.5
C10—C11—Cl1118.73 (12)H22B—C22—H22C109.5
C11—C12—C13119.42 (13)
C7—N2—C1—C2−178.88 (15)C13—C8—C9—C10−1.5 (2)
C14—N2—C1—C2−4.0 (2)C7—C8—C9—C10−177.72 (13)
C7—N2—C1—C6−0.11 (15)C8—C9—C10—C112.2 (2)
C14—N2—C1—C6174.80 (13)C9—C10—C11—C12−1.1 (2)
N2—C1—C2—C3178.50 (15)C9—C10—C11—Cl1177.86 (11)
C6—C1—C2—C3−0.1 (2)C10—C11—C12—C13−0.8 (2)
C1—C2—C3—C40.3 (2)Cl1—C11—C12—C13−179.71 (11)
C2—C3—C4—C5−0.3 (2)C11—C12—C13—C81.5 (2)
C2—C3—C4—C20−179.22 (14)C9—C8—C13—C12−0.4 (2)
C3—C4—C5—C6−0.1 (2)C7—C8—C13—C12175.52 (13)
C20—C4—C5—C6178.85 (13)C1—N2—C14—C1965.11 (19)
C7—N1—C6—C5179.06 (15)C7—N2—C14—C19−121.21 (16)
C7—N1—C6—C1−0.26 (16)C1—N2—C14—C15−114.00 (16)
C4—C5—C6—N1−178.95 (14)C7—N2—C14—C1559.7 (2)
C4—C5—C6—C10.3 (2)C19—C14—C15—C16−0.6 (2)
N2—C1—C6—N10.23 (16)N2—C14—C15—C16178.49 (13)
C2—C1—C6—N1179.15 (13)C14—C15—C16—C170.8 (2)
N2—C1—C6—C5−179.16 (13)C15—C16—C17—C18−0.1 (2)
C2—C1—C6—C5−0.2 (2)C16—C17—C18—C19−0.8 (2)
C6—N1—C7—N20.19 (16)C15—C14—C19—C18−0.3 (2)
C6—N1—C7—C8179.89 (13)N2—C14—C19—C18−179.41 (14)
C1—N2—C7—N1−0.05 (16)C17—C18—C19—C141.0 (2)
C14—N2—C7—N1−174.62 (13)C21—O1—C20—O2−0.5 (2)
C1—N2—C7—C8−179.73 (13)C21—O1—C20—C4179.16 (12)
C14—N2—C7—C85.7 (2)C5—C4—C20—O2178.84 (15)
N1—C7—C8—C13−149.37 (15)C3—C4—C20—O2−2.2 (2)
N2—C7—C8—C1330.3 (2)C5—C4—C20—O1−0.83 (19)
N1—C7—C8—C926.6 (2)C3—C4—C20—O1178.10 (13)
N2—C7—C8—C9−153.74 (14)C20—O1—C21—C22−175.16 (12)
D—H···AD—HH···AD···AD—H···A
C15—H15A···O2i0.952.393.324 (2)166
C21—H21A···Cg1ii0.992.633.5183 (16)149
C12—H12A···Cg2iii0.952.963.5940 (16)125
C19—H19A···Cg3iii0.952.603.4770 (18)153
Table 1

Hydrogen-bond geometry (Å, °)

Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C15—H15A⋯O2i0.952.393.324 (2)166
C21—H21A⋯Cg1ii0.992.633.5183 (16)149
C12—H12A⋯Cg2iii0.952.963.5940 (16)125
C19—H19A⋯Cg3iii0.952.603.4770 (18)153

Symmetry codes: (i) ; (ii) ; (iii) .

  7 in total

1.  A short history of SHELX.

Authors:  George M Sheldrick
Journal:  Acta Crystallogr A       Date:  2007-12-21       Impact factor: 2.290

Review 2.  Benzimidazole nucleosides, nucleotides, and related derivatives.

Authors:  L B Townsend; G R Revankar
Journal:  Chem Rev       Date:  1970-06       Impact factor: 60.622

3.  DNA sequence dependent monomer-dimer binding modulation of asymmetric benzimidazole derivatives.

Authors:  Farial A Tanious; Donald Hamelberg; Christian Bailly; Agnieska Czarny; David W Boykin; W David Wilson
Journal:  J Am Chem Soc       Date:  2004-01-14       Impact factor: 15.419

4.  Ethyl 1-[3-(2-oxopyrrolidin-1-yl)prop-yl]-2-phenyl-1H-benzimidazole-5-carboxyl-ate.

Authors:  Yeong Keng Yoon; Mohamed Ashraf Ali; Tan Soo Choon; Safra Izuani Jama Asik; Ibrahim Abdul Razak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-01-07

5.  Ethyl 1-[3-(1H-imidazol-1-yl)prop-yl]-2-(4-chloro-phen-yl)-1H-benzo[d]imidazole-5-carboxyl-ate dihydrate.

Authors:  Yeong Keng Yoon; Mohamed Ashraf Ali; Ang Chee Wei; Ching Kheng Quah; Hoong-Kun Fun
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2011-08-27

6.  2-(4-Chloro-phen-yl)-1-phenyl-1H-benz-imidazole.

Authors:  Karimah Kassim; N Zakiah N Hashim; Adibatul Husna Fadzil; M Sukeri M Yusof
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-02-24

7.  Structure validation in chemical crystallography.

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

1.  Ethyl 1-phenyl-2-[4-(trifluoro-meth-oxy)phen-yl]-1H-benzimidazole-5-carboxyl-ate.

Authors:  Yeong Keng Yoon; Mohamed Ashraf Ali; Tan Soo Choon; Suhana Arshad; Ibrahim Abdul Razak
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2012-08-15
  1 in total

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