organic compounds
2-Methoxy-4,6-diphenylnicotinonitrile
aDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, bDepartment of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, Riyadh 11451, Saudi Arabia, and cDepartment of Medicinal Chemistry, Faculty of Pharmacy, University of Mansoura, Mansoura 35516, Egypt
*Correspondence e-mail: joelt@tulane.edu
In the title compound, C19H14N2O, the phenyl rings form dihedral angles of 10.90 (10) and 42.14 (6)° with pyridine ring and an angle of 35.7 (2)° with each other. The orientation of the methoxy group is defined by the C—O—C—N torsion angle of 4.9 (2)°.
CCDC reference: 983247
Related literature
For synthesis and drug-discovery studies of pyridine derivatives, see: Abdel-Aziz (2007); Abdel-Aziz et al. (2005); Cook et al. (2004); Upton et al. (2000); Al-Arab (1989); Perez-Medina et al. (1947). For related structures, see: Alvarez-Larena et al. (1994); Cao et al. (2009); Lv & Huang (2008); Mohamed et al. (2012); Patel et al. (2002).
Experimental
Crystal data
|
Data collection: APEX2 (Bruker, 2010); cell SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).
Supporting information
CCDC reference: 983247
10.1107/S1600536814001755/lh5683sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536814001755/lh5683Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536814001755/lh5683Isup3.cml
The title compound was prepared by the literature method (Al-Arab, 1989) and crystallized from acetone as slender, colourless plates.
H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2–1.5 times those of the attached carbon atoms.
Compounds containing the pyridine nucleus are known to exhibit a large number of important biological properties (Perez-Medina et al., 1947; Upton et al., 2000; Cook et al., 2004). As part of our ongoing program of drug discovery and design we report the structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. The pendant phenyl rings (C8-C13) and (C14-C19) form dihedral angles of 10.90 (10) and 42.14 (6)°, respectively, with the central pyridine ring and a dihedral angle of 35.7 (2)° with each other. There are no significant intermolecular interactions which contrasts with the structure of the ethoxy analog where C—H···π and π—π stacking interactions are proposed (Patel et al., 2002). The methoxy group is almost coplanar with the pyridine ring as indicated by the C6—O1—C5—N1 torsion angle of 4.9 (2)°. The conformations of related 2,4-diphenylpyridine derivatives differ from that of the title compound in the orientations of the pendant phenyl groups relative to the pyridine ring (Alvarez-Larena, et al., 1994; Cao et al., 2009; Lv & Huang, 2008; Mohamed et al., 2012; Patel et al., 2002).
For synthesis and drug-discovery studies of pyridine derivatives, see: Abdel-Aziz (2007); Abdel-Aziz et al. (2005); Cook et al. (2004); Upton et al. (2000); Al-Arab (1989); Perez-Medina et al. (1947). For related structures, see: Alvarez-Larena et al. (1994); Cao et al. (2009); Lv & Huang (2008); Mohamed et al. (2012); Patel et al. (2002).
Data collection: APEX2 (Bruker, 2010); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: DIAMOND (Brandenburg & Putz, 2012); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).Fig. 1. The molecular structure of the title compound. Displacement ellipsoids are drawn at the 50% probability level. |
C19H14N2O | F(000) = 600 |
Mr = 286.32 | Dx = 1.331 Mg m−3 |
Orthorhombic, P21212 | Mo Kα radiation, λ = 0.71073 Å |
Hall symbol: P 2 2ab | Cell parameters from 7963 reflections |
a = 15.0686 (16) Å | θ = 2.7–28.4° |
b = 24.327 (3) Å | µ = 0.08 mm−1 |
c = 3.8986 (4) Å | T = 100 K |
V = 1429.1 (3) Å3 | Plate, colourless |
Z = 4 | 0.22 × 0.11 × 0.06 mm |
Bruker SMART APEXII CCD diffractometer | 3344 independent reflections |
Radiation source: fine-focus sealed tube | 2983 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.047 |
φ and ω scans | θmax = 28.5°, θmin = 1.6° |
Absorption correction: multi-scan (SADABS; Sheldrick, 2009) | h = −19→20 |
Tmin = 0.982, Tmax = 0.995 | k = −31→31 |
12356 measured reflections | l = −5→5 |
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)] = 0.040 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | w = 1/[σ2(Fo2) + (0.0325P)2 + 0.477P] where P = (Fo2 + 2Fc2)/3 |
3344 reflections | (Δ/σ)max < 0.001 |
200 parameters | Δρmax = 0.20 e Å−3 |
0 restraints | Δρmin = −0.21 e Å−3 |
C19H14N2O | V = 1429.1 (3) Å3 |
Mr = 286.32 | Z = 4 |
Orthorhombic, P21212 | Mo Kα radiation |
a = 15.0686 (16) Å | µ = 0.08 mm−1 |
b = 24.327 (3) Å | T = 100 K |
c = 3.8986 (4) Å | 0.22 × 0.11 × 0.06 mm |
Bruker SMART APEXII CCD diffractometer | 3344 independent reflections |
Absorption correction: multi-scan (SADABS; Sheldrick, 2009) | 2983 reflections with I > 2σ(I) |
Tmin = 0.982, Tmax = 0.995 | Rint = 0.047 |
12356 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.04 | Δρmax = 0.20 e Å−3 |
3344 reflections | Δρmin = −0.21 e Å−3 |
200 parameters |
Experimental. The diffraction data were collected in three sets of 606 frames (0.3° width in ω) at φ = 0, 120 and 240°. A scan time of 40 sec/frame was used. |
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. H-atoms were placed in calculated positions (C—H = 0.95 - 0.98 Å) and included as riding contributions with isotropic displacement parameters 1.2 - 1.5 times those of the attached carbon atoms. 1280 Friedel pairs were left unmerged but the absolute structure could not be reliably determined. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.43017 (8) | 0.12053 (5) | 0.0589 (4) | 0.0260 (3) | |
N1 | 0.57518 (9) | 0.11317 (5) | 0.2415 (4) | 0.0213 (3) | |
N2 | 0.38885 (10) | 0.24495 (6) | −0.3038 (4) | 0.0283 (3) | |
C1 | 0.65658 (10) | 0.13660 (6) | 0.2753 (4) | 0.0189 (3) | |
C2 | 0.67269 (11) | 0.19050 (6) | 0.1762 (4) | 0.0194 (3) | |
H2 | 0.7302 | 0.2058 | 0.2047 | 0.023* | |
C3 | 0.60488 (11) | 0.22245 (7) | 0.0350 (4) | 0.0189 (3) | |
C4 | 0.52180 (11) | 0.19767 (7) | −0.0084 (5) | 0.0198 (4) | |
C5 | 0.51198 (11) | 0.14286 (7) | 0.1036 (5) | 0.0208 (4) | |
C6 | 0.41763 (12) | 0.06623 (7) | 0.1956 (6) | 0.0310 (4) | |
H6A | 0.4557 | 0.0403 | 0.0720 | 0.046* | |
H6B | 0.3554 | 0.0554 | 0.1683 | 0.046* | |
H6C | 0.4332 | 0.0660 | 0.4396 | 0.046* | |
C7 | 0.44794 (11) | 0.22442 (7) | −0.1697 (5) | 0.0215 (3) | |
C8 | 0.72680 (11) | 0.10115 (7) | 0.4250 (4) | 0.0194 (3) | |
C9 | 0.70457 (11) | 0.05036 (7) | 0.5689 (5) | 0.0226 (4) | |
H9 | 0.6442 | 0.0392 | 0.5762 | 0.027* | |
C10 | 0.76945 (11) | 0.01607 (7) | 0.7011 (5) | 0.0250 (4) | |
H10 | 0.7534 | −0.0184 | 0.7976 | 0.030* | |
C11 | 0.85806 (12) | 0.03196 (7) | 0.6928 (5) | 0.0256 (4) | |
H11 | 0.9028 | 0.0085 | 0.7821 | 0.031* | |
C12 | 0.88043 (12) | 0.08248 (7) | 0.5528 (5) | 0.0263 (4) | |
H12 | 0.9409 | 0.0936 | 0.5473 | 0.032* | |
C13 | 0.81601 (11) | 0.11685 (7) | 0.4214 (5) | 0.0234 (4) | |
H13 | 0.8324 | 0.1514 | 0.3277 | 0.028* | |
C14 | 0.62283 (11) | 0.28047 (7) | −0.0627 (4) | 0.0190 (3) | |
C15 | 0.56225 (11) | 0.32239 (7) | 0.0117 (4) | 0.0218 (4) | |
H15 | 0.5077 | 0.3140 | 0.1223 | 0.026* | |
C16 | 0.58217 (11) | 0.37627 (7) | −0.0770 (5) | 0.0237 (4) | |
H16 | 0.5413 | 0.4048 | −0.0245 | 0.028* | |
C17 | 0.66093 (12) | 0.38876 (7) | −0.2411 (5) | 0.0257 (4) | |
H17 | 0.6737 | 0.4257 | −0.3029 | 0.031* | |
C18 | 0.72141 (11) | 0.34755 (7) | −0.3158 (5) | 0.0241 (4) | |
H18 | 0.7753 | 0.3561 | −0.4305 | 0.029* | |
C19 | 0.70285 (11) | 0.29378 (7) | −0.2222 (4) | 0.0213 (3) | |
H19 | 0.7451 | 0.2657 | −0.2672 | 0.026* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0191 (6) | 0.0201 (6) | 0.0388 (7) | −0.0036 (5) | −0.0033 (6) | 0.0000 (5) |
N1 | 0.0203 (7) | 0.0194 (6) | 0.0241 (8) | −0.0007 (5) | 0.0008 (6) | −0.0018 (6) |
N2 | 0.0236 (7) | 0.0269 (7) | 0.0345 (8) | 0.0006 (6) | −0.0047 (7) | −0.0002 (7) |
C1 | 0.0193 (7) | 0.0201 (7) | 0.0172 (8) | 0.0011 (6) | 0.0013 (6) | −0.0032 (6) |
C2 | 0.0183 (7) | 0.0201 (8) | 0.0197 (8) | −0.0004 (6) | −0.0003 (7) | −0.0032 (6) |
C3 | 0.0208 (8) | 0.0199 (7) | 0.0160 (8) | 0.0012 (6) | 0.0020 (7) | −0.0024 (6) |
C4 | 0.0184 (8) | 0.0199 (8) | 0.0210 (9) | 0.0019 (6) | −0.0003 (7) | −0.0024 (7) |
C5 | 0.0172 (8) | 0.0213 (8) | 0.0237 (9) | −0.0016 (6) | 0.0018 (7) | −0.0037 (7) |
C6 | 0.0254 (9) | 0.0224 (9) | 0.0451 (12) | −0.0059 (7) | −0.0031 (9) | 0.0021 (8) |
C7 | 0.0206 (8) | 0.0198 (8) | 0.0241 (9) | −0.0017 (6) | 0.0017 (7) | −0.0013 (7) |
C8 | 0.0207 (8) | 0.0194 (8) | 0.0182 (8) | 0.0007 (6) | −0.0002 (7) | −0.0030 (6) |
C9 | 0.0225 (8) | 0.0214 (8) | 0.0241 (9) | −0.0007 (7) | 0.0020 (8) | −0.0010 (7) |
C10 | 0.0296 (9) | 0.0201 (8) | 0.0254 (9) | 0.0019 (7) | 0.0021 (8) | 0.0017 (7) |
C11 | 0.0268 (9) | 0.0252 (8) | 0.0249 (9) | 0.0056 (7) | −0.0005 (8) | 0.0019 (7) |
C12 | 0.0226 (8) | 0.0286 (9) | 0.0277 (9) | 0.0005 (7) | −0.0037 (8) | −0.0010 (7) |
C13 | 0.0249 (8) | 0.0194 (8) | 0.0259 (9) | −0.0015 (7) | −0.0012 (7) | 0.0003 (7) |
C14 | 0.0207 (8) | 0.0191 (7) | 0.0172 (7) | 0.0004 (6) | −0.0031 (7) | −0.0009 (6) |
C15 | 0.0209 (8) | 0.0224 (8) | 0.0222 (9) | −0.0006 (7) | −0.0005 (7) | −0.0016 (7) |
C16 | 0.0264 (9) | 0.0201 (8) | 0.0245 (9) | 0.0024 (7) | −0.0033 (7) | −0.0013 (7) |
C17 | 0.0331 (9) | 0.0202 (8) | 0.0238 (9) | −0.0042 (7) | −0.0055 (8) | 0.0020 (7) |
C18 | 0.0233 (8) | 0.0268 (9) | 0.0222 (8) | −0.0045 (7) | −0.0009 (7) | 0.0008 (7) |
C19 | 0.0211 (8) | 0.0225 (8) | 0.0203 (8) | 0.0009 (6) | −0.0013 (7) | −0.0032 (7) |
O1—C5 | 1.3583 (19) | C9—H9 | 0.9500 |
O1—C6 | 1.437 (2) | C10—C11 | 1.390 (2) |
N1—C5 | 1.311 (2) | C10—H10 | 0.9500 |
N1—C1 | 1.359 (2) | C11—C12 | 1.386 (2) |
N2—C7 | 1.147 (2) | C11—H11 | 0.9500 |
C1—C2 | 1.388 (2) | C12—C13 | 1.380 (2) |
C1—C8 | 1.485 (2) | C12—H12 | 0.9500 |
C2—C3 | 1.397 (2) | C13—H13 | 0.9500 |
C2—H2 | 0.9500 | C14—C19 | 1.395 (2) |
C3—C4 | 1.400 (2) | C14—C15 | 1.399 (2) |
C3—C14 | 1.487 (2) | C15—C16 | 1.388 (2) |
C4—C5 | 1.411 (2) | C15—H15 | 0.9500 |
C4—C7 | 1.435 (2) | C16—C17 | 1.382 (2) |
C6—H6A | 0.9800 | C16—H16 | 0.9500 |
C6—H6B | 0.9800 | C17—C18 | 1.386 (2) |
C6—H6C | 0.9800 | C17—H17 | 0.9500 |
C8—C13 | 1.397 (2) | C18—C19 | 1.386 (2) |
C8—C9 | 1.398 (2) | C18—H18 | 0.9500 |
C9—C10 | 1.385 (2) | C19—H19 | 0.9500 |
C5—O1—C6 | 116.07 (13) | C9—C10—C11 | 120.12 (16) |
C5—N1—C1 | 117.68 (14) | C9—C10—H10 | 119.9 |
N1—C1—C2 | 121.80 (15) | C11—C10—H10 | 119.9 |
N1—C1—C8 | 115.97 (14) | C12—C11—C10 | 119.29 (16) |
C2—C1—C8 | 122.23 (14) | C12—C11—H11 | 120.4 |
C1—C2—C3 | 120.49 (15) | C10—C11—H11 | 120.4 |
C1—C2—H2 | 119.8 | C13—C12—C11 | 120.81 (17) |
C3—C2—H2 | 119.8 | C13—C12—H12 | 119.6 |
C2—C3—C4 | 117.52 (15) | C11—C12—H12 | 119.6 |
C2—C3—C14 | 119.74 (15) | C12—C13—C8 | 120.49 (16) |
C4—C3—C14 | 122.74 (15) | C12—C13—H13 | 119.8 |
C3—C4—C5 | 117.62 (15) | C8—C13—H13 | 119.8 |
C3—C4—C7 | 123.46 (15) | C19—C14—C15 | 119.15 (15) |
C5—C4—C7 | 118.89 (15) | C19—C14—C3 | 119.47 (14) |
N1—C5—O1 | 119.45 (15) | C15—C14—C3 | 121.35 (15) |
N1—C5—C4 | 124.86 (15) | C16—C15—C14 | 119.70 (16) |
O1—C5—C4 | 115.69 (14) | C16—C15—H15 | 120.1 |
O1—C6—H6A | 109.5 | C14—C15—H15 | 120.1 |
O1—C6—H6B | 109.5 | C17—C16—C15 | 120.56 (16) |
H6A—C6—H6B | 109.5 | C17—C16—H16 | 119.7 |
O1—C6—H6C | 109.5 | C15—C16—H16 | 119.7 |
H6A—C6—H6C | 109.5 | C16—C17—C18 | 120.19 (15) |
H6B—C6—H6C | 109.5 | C16—C17—H17 | 119.9 |
N2—C7—C4 | 178.56 (19) | C18—C17—H17 | 119.9 |
C13—C8—C9 | 118.44 (15) | C17—C18—C19 | 119.64 (16) |
C13—C8—C1 | 121.52 (15) | C17—C18—H18 | 120.2 |
C9—C8—C1 | 120.03 (14) | C19—C18—H18 | 120.2 |
C10—C9—C8 | 120.84 (16) | C18—C19—C14 | 120.72 (15) |
C10—C9—H9 | 119.6 | C18—C19—H19 | 119.6 |
C8—C9—H9 | 119.6 | C14—C19—H19 | 119.6 |
C5—N1—C1—C2 | 1.6 (2) | C2—C1—C8—C9 | 170.16 (16) |
C5—N1—C1—C8 | −178.59 (15) | C13—C8—C9—C10 | −0.8 (3) |
N1—C1—C2—C3 | −0.4 (2) | C1—C8—C9—C10 | 178.17 (16) |
C8—C1—C2—C3 | 179.74 (15) | C8—C9—C10—C11 | 0.2 (3) |
C1—C2—C3—C4 | −1.4 (2) | C9—C10—C11—C12 | 0.3 (3) |
C1—C2—C3—C14 | 178.68 (15) | C10—C11—C12—C13 | −0.2 (3) |
C2—C3—C4—C5 | 1.9 (2) | C11—C12—C13—C8 | −0.4 (3) |
C14—C3—C4—C5 | −178.09 (15) | C9—C8—C13—C12 | 0.9 (3) |
C2—C3—C4—C7 | −175.93 (16) | C1—C8—C13—C12 | −178.03 (16) |
C14—C3—C4—C7 | 4.0 (3) | C2—C3—C14—C19 | 40.9 (2) |
C1—N1—C5—O1 | 178.65 (15) | C4—C3—C14—C19 | −139.07 (17) |
C1—N1—C5—C4 | −0.9 (3) | C2—C3—C14—C15 | −137.09 (17) |
C6—O1—C5—N1 | 4.9 (2) | C4—C3—C14—C15 | 42.9 (2) |
C6—O1—C5—C4 | −175.45 (16) | C19—C14—C15—C16 | 0.6 (2) |
C3—C4—C5—N1 | −0.9 (3) | C3—C14—C15—C16 | 178.63 (15) |
C7—C4—C5—N1 | 177.11 (17) | C14—C15—C16—C17 | 0.6 (3) |
C3—C4—C5—O1 | 179.55 (15) | C15—C16—C17—C18 | −0.7 (3) |
C7—C4—C5—O1 | −2.5 (2) | C16—C17—C18—C19 | −0.6 (3) |
N1—C1—C8—C13 | 169.24 (16) | C17—C18—C19—C14 | 1.9 (3) |
C2—C1—C8—C13 | −10.9 (2) | C15—C14—C19—C18 | −1.9 (2) |
N1—C1—C8—C9 | −9.7 (2) | C3—C14—C19—C18 | −179.94 (16) |
Experimental details
Crystal data | |
Chemical formula | C19H14N2O |
Mr | 286.32 |
Crystal system, space group | Orthorhombic, P21212 |
Temperature (K) | 100 |
a, b, c (Å) | 15.0686 (16), 24.327 (3), 3.8986 (4) |
V (Å3) | 1429.1 (3) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.08 |
Crystal size (mm) | 0.22 × 0.11 × 0.06 |
Data collection | |
Diffractometer | Bruker SMART APEXII CCD |
Absorption correction | Multi-scan (SADABS; Sheldrick, 2009) |
Tmin, Tmax | 0.982, 0.995 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12356, 3344, 2983 |
Rint | 0.047 |
(sin θ/λ)max (Å−1) | 0.670 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.093, 1.04 |
No. of reflections | 3344 |
No. of parameters | 200 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.20, −0.21 |
Computer programs: APEX2 (Bruker, 2010), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), DIAMOND (Brandenburg & Putz, 2012), SHELXTL (Sheldrick, 2008).
Footnotes
‡Additional correspondence author, e-mail: alaa_moenes@yahoo.com.
Acknowledgements
We thank the Deanship of Scientific Research and the Research Center of the College of Pharmacy, King Saud University, for support. JTM thanks Tulane University for support of the Tulane Crystallography Laboratory.
References
Abdel-Aziz, A. A.-M. (2007). Tetrahedron Lett. 48, 2861–2865. Web of Science CrossRef CAS Google Scholar
Abdel-Aziz, A. A.-M., El-Subbagh, H. I. & Kunieda, T. (2005). Bioorg. Med. Chem. 13, 4929–4935. Web of Science PubMed CAS Google Scholar
Al-Arab, M. M. (1989). J. Heterocycl. Chem. 26, 1665–1673. CAS Google Scholar
Alvarez-Larena, A., Piniella, J. F., Victory, P., Borrell, J. I. & Vidal-Ferran, A. (1994). Z. Kristallogr. 209, 773–774. CAS Google Scholar
Brandenburg, K. & Putz, H. (2012). DIAMOND. Crystal Impact GbR, Bonn, Germany. Google Scholar
Bruker (2009). SAINT, Bruker AXS Inc., Madison, Wisconson, USA. Google Scholar
Bruker (2010). APEX2, Bruker AXS Inc., Madison, Wisconson, USA. Google Scholar
Cao, Q., Xie, Y., Jia, J. & Hong, X.-W. (2009). Acta Cryst. E65, o3182. Web of Science CSD CrossRef IUCr Journals Google Scholar
Cook, C. E., Sloan, C. D., Thomas, B. F. & Navarro, H. A. (2004). Chem. Abstr. 141, 157039 861. Google Scholar
Lv, L. L. & Huang, X.-Q. (2008). Acta Cryst. E64, o186. Web of Science CSD CrossRef IUCr Journals Google Scholar
Mohamed, S. K., Akkurt, M., Abdelhamid, A. A., Singh, K. & El-Remaily, M. A. A. (2012). Acta Cryst. E68, o2495–o2496. CSD CrossRef CAS IUCr Journals Google Scholar
Patel, U. H., Dave, C. G., Jotani, M. M. & Shah, H. C. (2002). Acta Cryst. C58, o697–o699. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
Perez-Medina, L. A., Merriella, R. P. & McElvain, S. M. (1947). J. Am. Chem. Soc. 69, 2574–2579. CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Sheldrick, G. M. (2009). SADABS. University of Göttingen, Germany. Google Scholar
Upton, C., Osborne, R. H. & Jaffar, M. (2000). Bioorg. Med. Chem. Lett. 10, 1277–1279. Web of Science CrossRef PubMed CAS 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.
Compounds containing the pyridine nucleus are known to exhibit a large number of important biological properties (Perez-Medina et al., 1947; Upton et al., 2000; Cook et al., 2004). As part of our ongoing program of drug discovery and design we report the structure of the title compound. The molecular structure of the title compound is shown in Fig. 1. The pendant phenyl rings (C8-C13) and (C14-C19) form dihedral angles of 10.90 (10) and 42.14 (6)°, respectively, with the central pyridine ring and a dihedral angle of 35.7 (2)° with each other. There are no significant intermolecular interactions which contrasts with the structure of the ethoxy analog where C—H···π and π—π stacking interactions are proposed (Patel et al., 2002). The methoxy group is almost coplanar with the pyridine ring as indicated by the C6—O1—C5—N1 torsion angle of 4.9 (2)°. The conformations of related 2,4-diphenylpyridine derivatives differ from that of the title compound in the orientations of the pendant phenyl groups relative to the pyridine ring (Alvarez-Larena, et al., 1994; Cao et al., 2009; Lv & Huang, 2008; Mohamed et al., 2012; Patel et al., 2002).