2-Meth-oxy-4,6-di-phenyl-nicotino-nitrile.

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 meth-oxy group is defined by the C-O-C-N torsion angle of 4.9 (2)°.

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

C19H14N2O

M = 286.32

Orthorhombic,

a = 15.0686 (16) Å

b = 24.327 (3) Å

c = 3.8986 (4) Å

V = 1429.1 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.22 × 0.11 × 0.06 mm

Data collection

Bruker SMART APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2009 ▶) T min = 0.982, T max = 0.995

12356 measured reflections

3344 independent reflections

2983 reflections with I > 2σ(I)

R int = 0.047

Refinement

R[F 2 > 2σ(F 2)] = 0.040

wR(F 2) = 0.093

S = 1.04

3344 reflections

200 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.21 e Å−3

Data collection: APEX2 (Bruker, 2010 ▶); cell refinement: 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536814001755/lh5683sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536814001755/lh5683Isup2.hkl

Click here for additional data file.

Supporting information file. DOI: 10.1107/S1600536814001755/lh5683Isup3.cml

CCDC reference:

Additional supporting information: crystallographic information; 3D view; checkCIF report

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

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)