organic compounds
Ethyl 2-(4-chlorophenyl)-1-phenyl-1H-benzimidazole-5-carboxylate
aInstitute for Research in Molecular Medicine, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia, bDepartment of Pharmaceutical Sciences, UCSI University, Kuala Lumpur, Cheras 56000, Malaysia, and cSchool of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia
*Correspondence e-mail: arazaki@usm.my
In the title compound, C22H17ClN2O2, 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, molecules are linked into a zigzag chain along the a axis by intermolecular C—H⋯O hydrogen bonds. C—H⋯π interactions are also present.
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
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Refinement
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Data collection: APEX2 (Bruker, 2009); cell 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).
Supporting information
10.1107/S1600536812022192/is5137sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812022192/is5137Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812022192/is5137Isup3.cml
Ethyl 3-amino-4-(phenyl amino) benzoate (0.84 mmol) and sodium metabisulfite adduct of chlorobenzaldehyde (1.68 mmol) were dissolved in DMF. The reaction mixture was reflux at 130 °C for 2 h. After completion, the reaction mixture was diluted in ethyl acetate (20 ml) and washed with water (20 ml). The organic layer was collected, dried over Na2SO4 and the evaporated in-vacuo to yield the product. The product was recrystallized from ethyl acetate.
All H atoms were positioned geometrically (C—H = 0.95–0.99 Å) and refined using a riding model with Uiso(H) = 1.2 and 1.5Ueq(C). A rotating group model was applied to the methyl group.
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atom-numbering scheme. | |
Fig. 2. A crystal packing diagram of the title compound viewed along the b axis. The H atoms not involved in the intermolecular interactions (dashed lines) have been omitted for clarity. |
C22H17ClN2O2 | Z = 2 |
Mr = 376.83 | F(000) = 392 |
Triclinic, P1 | Dx = 1.378 Mg m−3 |
Hall symbol: -P 1 | Mo Kα radiation, λ = 0.71073 Å |
a = 9.3357 (2) Å | Cell parameters from 7225 reflections |
b = 9.7982 (2) Å | θ = 2.6–30.2° |
c = 11.7718 (4) Å | µ = 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 diffractometer | 5326 independent reflections |
Radiation source: fine-focus sealed tube | 4233 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.033 |
ϕ and ω scans | θmax = 30.2°, θmin = 1.9° |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | h = −13→13 |
Tmin = 0.917, Tmax = 0.946 | k = −13→13 |
18472 measured reflections | l = −14→16 |
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)] = 0.048 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0648P)2 + 0.3753P] where P = (Fo2 + 2Fc2)/3 |
5326 reflections | (Δ/σ)max < 0.001 |
245 parameters | Δρmax = 0.57 e Å−3 |
0 restraints | Δρmin = −0.31 e Å−3 |
C22H17ClN2O2 | γ = 109.539 (1)° |
Mr = 376.83 | V = 908.31 (4) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.3357 (2) Å | Mo Kα radiation |
b = 9.7982 (2) Å | µ = 0.23 mm−1 |
c = 11.7718 (4) Å | T = 100 K |
α = 107.502 (2)° | 0.38 × 0.29 × 0.24 mm |
β = 102.106 (2)° |
Bruker SMART APEXII CCD area-detector diffractometer | 5326 independent reflections |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | 4233 reflections with I > 2σ(I) |
Tmin = 0.917, Tmax = 0.946 | Rint = 0.033 |
18472 measured reflections |
R[F2 > 2σ(F2)] = 0.048 | 0 restraints |
wR(F2) = 0.127 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.57 e Å−3 |
5326 reflections | Δρmin = −0.31 e Å−3 |
245 parameters |
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. |
x | y | z | Uiso*/Ueq | ||
Cl1 | −0.66895 (5) | −0.31206 (5) | −0.07003 (4) | 0.02705 (11) | |
O1 | 0.66316 (12) | −0.10624 (12) | 0.40052 (10) | 0.0196 (2) | |
O2 | 0.84606 (13) | 0.14573 (13) | 0.46871 (11) | 0.0229 (2) | |
N1 | 0.11793 (15) | −0.10887 (14) | 0.20878 (12) | 0.0173 (2) | |
N2 | 0.16095 (14) | 0.14100 (14) | 0.23348 (12) | 0.0158 (2) | |
C1 | 0.31182 (17) | 0.14553 (17) | 0.28366 (14) | 0.0165 (3) | |
C2 | 0.46660 (18) | 0.26942 (17) | 0.34187 (14) | 0.0190 (3) | |
H2A | 0.4848 | 0.3744 | 0.3520 | 0.023* | |
C3 | 0.59248 (18) | 0.23218 (18) | 0.38427 (15) | 0.0201 (3) | |
H3A | 0.6997 | 0.3136 | 0.4249 | 0.024* | |
C4 | 0.56507 (17) | 0.07571 (17) | 0.36849 (14) | 0.0179 (3) | |
C5 | 0.41041 (18) | −0.04706 (17) | 0.31022 (14) | 0.0180 (3) | |
H5A | 0.3924 | −0.1521 | 0.2997 | 0.022* | |
C6 | 0.28203 (17) | −0.01073 (17) | 0.26755 (13) | 0.0165 (3) | |
C7 | 0.04967 (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 | −0.2585 | 0.1881 | 0.021* | |
C10 | −0.39041 (19) | −0.28384 (18) | 0.08158 (14) | 0.0199 (3) | |
H10A | −0.4559 | −0.3739 | 0.0919 | 0.024* | |
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 | −0.0588 | 0.022* | |
C13 | −0.19981 (18) | −0.01465 (17) | 0.05489 (13) | 0.0171 (3) | |
H13A | −0.1354 | 0.0779 | 0.0470 | 0.021* | |
C14 | 0.13273 (17) | 0.27784 (17) | 0.23909 (13) | 0.0163 (3) | |
C15 | 0.04178 (18) | 0.32176 (18) | 0.31023 (14) | 0.0188 (3) | |
H15A | −0.0040 | 0.2607 | 0.3534 | 0.023* | |
C16 | 0.01898 (19) | 0.45680 (19) | 0.31695 (15) | 0.0223 (3) | |
H16A | −0.0417 | 0.4888 | 0.3661 | 0.027* | |
C17 | 0.0840 (2) | 0.54544 (18) | 0.25259 (16) | 0.0242 (3) | |
H17A | 0.0675 | 0.6374 | 0.2577 | 0.029* | |
C18 | 0.1728 (2) | 0.49899 (19) | 0.18094 (16) | 0.0246 (3) | |
H18A | 0.2161 | 0.5586 | 0.1360 | 0.029* | |
C19 | 0.19904 (19) | 0.36522 (18) | 0.17450 (14) | 0.0204 (3) | |
H19A | 0.2614 | 0.3343 | 0.1266 | 0.024* | |
C20 | 0.70739 (18) | 0.04619 (17) | 0.41852 (14) | 0.0171 (3) | |
C21 | 0.79321 (18) | −0.14740 (18) | 0.44432 (14) | 0.0188 (3) | |
H21A | 0.8447 | −0.0928 | 0.5378 | 0.023* | |
H21B | 0.8767 | −0.1165 | 0.4056 | 0.023* | |
C22 | 0.7175 (2) | −0.32370 (19) | 0.40427 (16) | 0.0254 (3) | |
H22A | 0.8013 | −0.3578 | 0.4317 | 0.038* | |
H22B | 0.6667 | −0.3759 | 0.3117 | 0.038* | |
H22C | 0.6354 | −0.3523 | 0.4433 | 0.038* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Cl1 | 0.01444 (18) | 0.0278 (2) | 0.0327 (2) | 0.00672 (15) | 0.00290 (15) | 0.01040 (16) |
O1 | 0.0137 (5) | 0.0191 (5) | 0.0244 (5) | 0.0072 (4) | 0.0042 (4) | 0.0082 (4) |
O2 | 0.0151 (5) | 0.0228 (5) | 0.0280 (6) | 0.0061 (5) | 0.0055 (4) | 0.0100 (5) |
N1 | 0.0149 (6) | 0.0164 (6) | 0.0196 (6) | 0.0061 (5) | 0.0041 (5) | 0.0077 (5) |
N2 | 0.0141 (6) | 0.0151 (5) | 0.0192 (6) | 0.0060 (5) | 0.0063 (5) | 0.0079 (5) |
C1 | 0.0151 (6) | 0.0175 (6) | 0.0181 (6) | 0.0073 (6) | 0.0064 (5) | 0.0081 (5) |
C2 | 0.0180 (7) | 0.0154 (6) | 0.0228 (7) | 0.0060 (6) | 0.0073 (6) | 0.0078 (6) |
C3 | 0.0152 (7) | 0.0189 (7) | 0.0237 (7) | 0.0049 (6) | 0.0067 (6) | 0.0082 (6) |
C4 | 0.0152 (7) | 0.0201 (7) | 0.0187 (7) | 0.0073 (6) | 0.0056 (5) | 0.0084 (6) |
C5 | 0.0169 (7) | 0.0170 (6) | 0.0206 (7) | 0.0074 (6) | 0.0064 (6) | 0.0080 (5) |
C6 | 0.0155 (6) | 0.0163 (6) | 0.0173 (6) | 0.0062 (6) | 0.0059 (5) | 0.0067 (5) |
C7 | 0.0163 (6) | 0.0150 (6) | 0.0156 (6) | 0.0057 (6) | 0.0053 (5) | 0.0064 (5) |
C8 | 0.0144 (6) | 0.0159 (6) | 0.0152 (6) | 0.0062 (5) | 0.0042 (5) | 0.0045 (5) |
C9 | 0.0177 (7) | 0.0179 (6) | 0.0172 (6) | 0.0069 (6) | 0.0057 (5) | 0.0073 (5) |
C10 | 0.0190 (7) | 0.0202 (7) | 0.0194 (7) | 0.0066 (6) | 0.0076 (6) | 0.0080 (6) |
C11 | 0.0140 (6) | 0.0224 (7) | 0.0180 (7) | 0.0076 (6) | 0.0047 (5) | 0.0048 (6) |
C12 | 0.0182 (7) | 0.0217 (7) | 0.0177 (7) | 0.0114 (6) | 0.0058 (5) | 0.0071 (5) |
C13 | 0.0183 (7) | 0.0170 (6) | 0.0176 (7) | 0.0082 (6) | 0.0072 (5) | 0.0075 (5) |
C14 | 0.0161 (6) | 0.0151 (6) | 0.0169 (6) | 0.0065 (6) | 0.0040 (5) | 0.0066 (5) |
C15 | 0.0172 (7) | 0.0196 (7) | 0.0190 (7) | 0.0074 (6) | 0.0058 (6) | 0.0076 (6) |
C16 | 0.0189 (7) | 0.0221 (7) | 0.0254 (8) | 0.0111 (6) | 0.0068 (6) | 0.0067 (6) |
C17 | 0.0225 (8) | 0.0173 (7) | 0.0295 (8) | 0.0094 (6) | 0.0027 (6) | 0.0086 (6) |
C18 | 0.0305 (8) | 0.0183 (7) | 0.0253 (8) | 0.0089 (7) | 0.0084 (7) | 0.0119 (6) |
C19 | 0.0240 (8) | 0.0191 (7) | 0.0202 (7) | 0.0092 (6) | 0.0099 (6) | 0.0090 (6) |
C20 | 0.0154 (6) | 0.0198 (7) | 0.0181 (7) | 0.0078 (6) | 0.0081 (5) | 0.0083 (5) |
C21 | 0.0154 (7) | 0.0219 (7) | 0.0198 (7) | 0.0097 (6) | 0.0049 (5) | 0.0081 (6) |
C22 | 0.0282 (8) | 0.0247 (8) | 0.0256 (8) | 0.0139 (7) | 0.0083 (7) | 0.0110 (6) |
Cl1—C11 | 1.7393 (15) | C10—C11 | 1.394 (2) |
O1—C20 | 1.3440 (17) | C10—H10A | 0.9500 |
O1—C21 | 1.4466 (17) | C11—C12 | 1.386 (2) |
O2—C20 | 1.2101 (18) | C12—C13 | 1.391 (2) |
N1—C7 | 1.3186 (18) | C12—H12A | 0.9500 |
N1—C6 | 1.3858 (19) | C13—H13A | 0.9500 |
N2—C1 | 1.3885 (17) | C14—C19 | 1.389 (2) |
N2—C7 | 1.3916 (18) | C14—C15 | 1.390 (2) |
N2—C14 | 1.4359 (17) | C15—C16 | 1.391 (2) |
C1—C2 | 1.394 (2) | C15—H15A | 0.9500 |
C1—C6 | 1.4057 (19) | C16—C17 | 1.390 (2) |
C2—C3 | 1.383 (2) | C16—H16A | 0.9500 |
C2—H2A | 0.9500 | C17—C18 | 1.386 (2) |
C3—C4 | 1.413 (2) | C17—H17A | 0.9500 |
C3—H3A | 0.9500 | C18—C19 | 1.395 (2) |
C4—C5 | 1.389 (2) | C18—H18A | 0.9500 |
C4—C20 | 1.4923 (19) | C19—H19A | 0.9500 |
C5—C6 | 1.3985 (19) | C21—C22 | 1.503 (2) |
C5—H5A | 0.9500 | C21—H21A | 0.9900 |
C7—C8 | 1.471 (2) | C21—H21B | 0.9900 |
C8—C13 | 1.3990 (19) | C22—H22A | 0.9800 |
C8—C9 | 1.403 (2) | C22—H22B | 0.9800 |
C9—C10 | 1.384 (2) | C22—H22C | 0.9800 |
C9—H9A | 0.9500 | ||
C20—O1—C21 | 115.83 (11) | C11—C12—H12A | 120.3 |
C7—N1—C6 | 105.12 (12) | C13—C12—H12A | 120.3 |
C1—N2—C7 | 106.08 (11) | C12—C13—C8 | 120.38 (14) |
C1—N2—C14 | 124.39 (12) | C12—C13—H13A | 119.8 |
C7—N2—C14 | 129.30 (12) | C8—C13—H13A | 119.8 |
N2—C1—C2 | 131.98 (13) | C19—C14—C15 | 121.23 (13) |
N2—C1—C6 | 105.41 (12) | C19—C14—N2 | 119.15 (13) |
C2—C1—C6 | 122.60 (13) | C15—C14—N2 | 119.61 (13) |
C3—C2—C1 | 116.80 (13) | C14—C15—C16 | 118.77 (14) |
C3—C2—H2A | 121.6 | C14—C15—H15A | 120.6 |
C1—C2—H2A | 121.6 | C16—C15—H15A | 120.6 |
C2—C3—C4 | 121.44 (14) | C17—C16—C15 | 120.81 (14) |
C2—C3—H3A | 119.3 | C17—C16—H16A | 119.6 |
C4—C3—H3A | 119.3 | C15—C16—H16A | 119.6 |
C5—C4—C3 | 121.36 (13) | C18—C17—C16 | 119.67 (14) |
C5—C4—C20 | 120.65 (13) | C18—C17—H17A | 120.2 |
C3—C4—C20 | 117.98 (13) | C16—C17—H17A | 120.2 |
C4—C5—C6 | 117.73 (13) | C17—C18—C19 | 120.38 (15) |
C4—C5—H5A | 121.1 | C17—C18—H18A | 119.8 |
C6—C5—H5A | 121.1 | C19—C18—H18A | 119.8 |
N1—C6—C5 | 129.46 (13) | C14—C19—C18 | 119.13 (14) |
N1—C6—C1 | 110.46 (12) | C14—C19—H19A | 120.4 |
C5—C6—C1 | 120.07 (13) | C18—C19—H19A | 120.4 |
N1—C7—N2 | 112.93 (12) | O2—C20—O1 | 123.55 (13) |
N1—C7—C8 | 121.50 (13) | O2—C20—C4 | 124.85 (13) |
N2—C7—C8 | 125.57 (12) | O1—C20—C4 | 111.60 (12) |
C13—C8—C9 | 118.95 (13) | O1—C21—C22 | 106.27 (12) |
C13—C8—C7 | 124.14 (13) | O1—C21—H21A | 110.5 |
C9—C8—C7 | 116.79 (12) | C22—C21—H21A | 110.5 |
C10—C9—C8 | 121.07 (13) | O1—C21—H21B | 110.5 |
C10—C9—H9A | 119.5 | C22—C21—H21B | 110.5 |
C8—C9—H9A | 119.5 | H21A—C21—H21B | 108.7 |
C9—C10—C11 | 118.76 (14) | C21—C22—H22A | 109.5 |
C9—C10—H10A | 120.6 | C21—C22—H22B | 109.5 |
C11—C10—H10A | 120.6 | H22A—C22—H22B | 109.5 |
C12—C11—C10 | 121.37 (14) | C21—C22—H22C | 109.5 |
C12—C11—Cl1 | 119.89 (11) | H22A—C22—H22C | 109.5 |
C10—C11—Cl1 | 118.73 (12) | H22B—C22—H22C | 109.5 |
C11—C12—C13 | 119.42 (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—C11 | 2.2 (2) |
C14—N2—C1—C6 | 174.80 (13) | C9—C10—C11—C12 | −1.1 (2) |
N2—C1—C2—C3 | 178.50 (15) | C9—C10—C11—Cl1 | 177.86 (11) |
C6—C1—C2—C3 | −0.1 (2) | C10—C11—C12—C13 | −0.8 (2) |
C1—C2—C3—C4 | 0.3 (2) | Cl1—C11—C12—C13 | −179.71 (11) |
C2—C3—C4—C5 | −0.3 (2) | C11—C12—C13—C8 | 1.5 (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—C12 | 175.52 (13) |
C20—C4—C5—C6 | 178.85 (13) | C1—N2—C14—C19 | 65.11 (19) |
C7—N1—C6—C5 | 179.06 (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—C15 | 59.7 (2) |
C4—C5—C6—C1 | 0.3 (2) | C19—C14—C15—C16 | −0.6 (2) |
N2—C1—C6—N1 | 0.23 (16) | N2—C14—C15—C16 | 178.49 (13) |
C2—C1—C6—N1 | 179.15 (13) | C14—C15—C16—C17 | 0.8 (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—N2 | 0.19 (16) | C15—C14—C19—C18 | −0.3 (2) |
C6—N1—C7—C8 | 179.89 (13) | N2—C14—C19—C18 | −179.41 (14) |
C1—N2—C7—N1 | −0.05 (16) | C17—C18—C19—C14 | 1.0 (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—C4 | 179.16 (12) |
C14—N2—C7—C8 | 5.7 (2) | C5—C4—C20—O2 | 178.84 (15) |
N1—C7—C8—C13 | −149.37 (15) | C3—C4—C20—O2 | −2.2 (2) |
N2—C7—C8—C13 | 30.3 (2) | C5—C4—C20—O1 | −0.83 (19) |
N1—C7—C8—C9 | 26.6 (2) | C3—C4—C20—O1 | 178.10 (13) |
N2—C7—C8—C9 | −153.74 (14) | C20—O1—C21—C22 | −175.16 (12) |
Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O2i | 0.95 | 2.39 | 3.324 (2) | 166 |
C21—H21A···Cg1ii | 0.99 | 2.63 | 3.5183 (16) | 149 |
C12—H12A···Cg2iii | 0.95 | 2.96 | 3.5940 (16) | 125 |
C19—H19A···Cg3iii | 0.95 | 2.60 | 3.4770 (18) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z. |
Experimental details
Crystal data | |
Chemical formula | C22H17ClN2O2 |
Mr | 376.83 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 100 |
a, b, c (Å) | 9.3357 (2), 9.7982 (2), 11.7718 (4) |
α, β, γ (°) | 107.502 (2), 102.106 (2), 109.539 (1) |
V (Å3) | 908.31 (4) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 0.23 |
Crystal size (mm) | 0.38 × 0.29 × 0.24 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD area-detector diffractometer |
Absorption correction | Multi-scan (SADABS; Bruker, 2009) |
Tmin, Tmax | 0.917, 0.946 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 18472, 5326, 4233 |
Rint | 0.033 |
(sin θ/λ)max (Å−1) | 0.708 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.048, 0.127, 1.04 |
No. of reflections | 5326 |
No. of parameters | 245 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.57, −0.31 |
Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).
Cg1, Cg2 and Cg3 are the centroids of the N1/C7/N2/C1/C6, C1–C6 and C8–C13 rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C15—H15A···O2i | 0.95 | 2.39 | 3.324 (2) | 166 |
C21—H21A···Cg1ii | 0.99 | 2.63 | 3.5183 (16) | 149 |
C12—H12A···Cg2iii | 0.95 | 2.96 | 3.5940 (16) | 125 |
C19—H19A···Cg3iii | 0.95 | 2.60 | 3.4770 (18) | 153 |
Symmetry codes: (i) x−1, y, z; (ii) −x+1, −y, −z+1; (iii) −x, −y, −z. |
Footnotes
‡Thomson Reuters ResearcherID: A-5599-2009.
Acknowledgements
The authors thank the Malaysian Government and Universiti Sains Malaysia (USM) for the Research University Grant Nos.1001/PFIZIK/811151 and 1001/PSK/8620012. The authors also wish to express their thanks to the Pharmacogenetic and Novel Therapeutic Research, Institute for Research in Molecular Medicine, Universiti Sains Malaysia. SA also thanks the Malaysian Government and USM for an Academic Staff Training Scheme (ASTS) fellowship.
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.
Substituted benzimidazoles are proven important drug leads. Substituted benzimidazole is the key building block for numerous compounds which plays crucial roles in the function of biologically important molecules (Tanious et al., 2004). In particular, 2-substituted benzimidazoles are recognized as potential anticancer agents (Townsend & Revankar, 1970). As part of our ongoing structural studies of benzimidazole derivatives (Yoon et al., 2011), we now report the structure of the title compound.
In the molecular structure (Fig. 1), The benzimidazole ring system (N1/N2/C1—C7) is essentially planar with a maximum deviation of 0.012 (2) Å at atom C1 and forms dihedral angles of 28.69 (6) and 63.65 (7)°, respectively, with the phenyl (C8–C13) and chloro-substituted benzene (C14–C19) ring. The dihedral angle between the phenyl ring and the chloro-substituted benzene ring is 64.23 (8)°. Bond lengths and angles are within normal ranges and are comparable to related structures (Yoon et al., 2011; Kassim et al., 2012; Yoon et al., 2012).
The crystal packing is shown in Fig. 2. The molecules are linked into a zigzag chain along the a-axis via intermolecular C15—H15A···O2 (Table 1) hydrogen bonds. The crystal structure is further stabilized by intermolecular C21—H21A···Cg1, C1—H12A···Cg2 and C19—H19A···Cg3 (Table 1) interactions (Cg1, Cg2 and Cg3 are the centroids of N1/N2/C1/C6/C7, C1–C6 and C8–C13 rings, respectively).