6-(4-Amino-phen-yl)-2-meth-oxy-4-phenyl-nicotino-nitrile.

In the structure of the title nicotino-nitrile derivative, C19H15N3O, the pyridine ring makes dihedral angles of 11.50 (7) and 43.36 (8)° with the 4-amino-phenyl and phenyl rings, respectively, and the dihedral angle between the phenyl rings is 36.28°. In the crystal, mol-ecules are linked by N-H⋯N hydrogen bonds into wave-like sheets parallel to (10-2). These sheets are stacked by π-π inter-actions between the 4-amino-phenyl rings of adjacent sheets, with centroid-centroid distances of 3.7499 (9) Å. C-H⋯π inter-actions are also present.

Related literature

For the synthesis and applications of nicotino­nitrile derivatives, see: Al-Jaber et al. (2012 ▶); Brandt et al. (2010 ▶); El-Sayed et al. (2011 ▶); Ji et al. (2007 ▶); Kim et al. (2005 ▶); Koner et al. (2012 ▶); Raghukumar et al. (2003 ▶); Zhou et al. (2006 ▶). For bond-length data, see: Allen et al. (1987 ▶). For related structures, see: Chantrapromma et al. (2013 ▶); Suwunwong et al. (2012 ▶, 2013 ▶).

Experimental

Crystal data

C19H15N3O

M = 301.34

Monoclinic,

a = 10.9448 (12) Å

b = 18.960 (2) Å

c = 7.4738 (8) Å

β = 94.743 (2)°

V = 1545.6 (3) Å3

Z = 4

Mo Kα radiation

μ = 0.08 mm−1

T = 100 K

0.56 × 0.17 × 0.06 mm

Data collection

Bruker APEX DUO CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.955, T max = 0.995

14200 measured reflections

3696 independent reflections

2689 reflections with I > 2σ(I)

R int = 0.051

Refinement

R[F 2 > 2σ(F 2)] = 0.046

wR(F 2) = 0.143

S = 1.07

3696 reflections

217 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.30 e Å−3

Δρmin = −0.28 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, PLATON (Spek, 2009 ▶), Mercury (Macrae et al., 2006 ▶) and publCIF (Westrip, 2010 ▶).

Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536813031437/sj5368sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813031437/sj5368Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813031437/sj5368Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C19H15N3O	F(000) = 632
Mr = 301.34	Dx = 1.295 Mg m−3
Monoclinic, P21/c	Melting point = 475–476 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.9448 (12) Å	Cell parameters from 3696 reflections
b = 18.960 (2) Å	θ = 2.2–28.0°
c = 7.4738 (8) Å	µ = 0.08 mm−1
β = 94.743 (2)°	T = 100 K
V = 1545.6 (3) Å3	Plate, yellow
Z = 4	0.56 × 0.17 × 0.06 mm

Bruker APEX DUO CCD area-detector diffractometer	3696 independent reflections
Radiation source: sealed tube	2689 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.051
φ and ω scans	θmax = 28.0°, θmin = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −14→14
Tmin = 0.955, Tmax = 0.995	k = −24→25
14200 measured reflections	l = −9→9

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)] = 0.046	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.143	H atoms treated by a mixture of independent and constrained refinement
S = 1.07	w = 1/[σ2(Fo2) + (0.0815P)2 + 0.0098P] where P = (Fo2 + 2Fc2)/3
3696 reflections	(Δ/σ)max = 0.001
217 parameters	Δρmax = 0.30 e Å−3
0 restraints	Δρmin = −0.28 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.

	x	y	z	Uiso*/Ueq
O1	0.41334 (9)	0.11886 (5)	0.32484 (15)	0.0232 (3)
N1	0.87443 (12)	0.47258 (7)	0.5990 (2)	0.0275 (3)
H2N1	0.9480 (17)	0.4498 (10)	0.619 (3)	0.036 (5)*
H1N1	0.8776 (17)	0.5170 (11)	0.554 (3)	0.043 (6)*
N2	0.48483 (11)	0.23181 (6)	0.37739 (17)	0.0197 (3)
N3	0.12753 (11)	0.11690 (6)	0.1173 (2)	0.0262 (3)
C1	0.56914 (12)	0.34757 (7)	0.4295 (2)	0.0188 (3)
C2	0.56860 (13)	0.42059 (7)	0.4009 (2)	0.0211 (3)
H2A	0.4974	0.4421	0.3435	0.025*
C3	0.66877 (13)	0.46216 (7)	0.4540 (2)	0.0222 (3)
H3A	0.6659	0.5115	0.4320	0.027*
C4	0.77484 (13)	0.43173 (7)	0.5405 (2)	0.0211 (3)
C5	0.77592 (13)	0.35885 (8)	0.5715 (2)	0.0231 (3)
H5A	0.8465	0.3374	0.6310	0.028*
C6	0.67552 (13)	0.31784 (7)	0.5163 (2)	0.0218 (3)
H6A	0.6785	0.2684	0.5375	0.026*
C7	0.46428 (12)	0.30246 (7)	0.3692 (2)	0.0191 (3)
C8	0.34949 (13)	0.32942 (7)	0.3085 (2)	0.0193 (3)
H8A	0.3365	0.3790	0.3080	0.023*
C9	0.25383 (12)	0.28457 (7)	0.2485 (2)	0.0188 (3)
C10	0.13113 (13)	0.31369 (7)	0.1898 (2)	0.0205 (3)
C11	0.02459 (13)	0.28273 (8)	0.2451 (2)	0.0245 (3)
H11A	0.0301	0.2420	0.3193	0.029*
C12	−0.08913 (14)	0.31153 (9)	0.1918 (2)	0.0315 (4)
H12A	−0.1613	0.2909	0.2313	0.038*
C13	−0.09812 (16)	0.37035 (9)	0.0810 (3)	0.0366 (5)
H13A	−0.1763	0.3894	0.0432	0.044*
C14	0.00695 (16)	0.40117 (8)	0.0257 (3)	0.0336 (4)
H14A	0.0008	0.4413	−0.0506	0.040*
C15	0.12153 (14)	0.37363 (8)	0.0814 (2)	0.0253 (4)
H15A	0.1935	0.3957	0.0455	0.030*
C16	0.39525 (12)	0.18928 (7)	0.3197 (2)	0.0192 (3)
C17	0.27805 (12)	0.21180 (7)	0.2504 (2)	0.0196 (3)
C18	0.19270 (13)	0.16011 (7)	0.1769 (2)	0.0207 (3)
C19	0.53384 (14)	0.09527 (8)	0.3919 (2)	0.0253 (4)
H19A	0.5373	0.0437	0.3870	0.038*
H19B	0.5509	0.1109	0.5164	0.038*
H19C	0.5952	0.1152	0.3179	0.038*

	U11	U22	U33	U12	U13	U23
O1	0.0235 (5)	0.0159 (5)	0.0299 (7)	−0.0003 (4)	−0.0009 (5)	−0.0005 (4)
N1	0.0209 (7)	0.0207 (6)	0.0401 (9)	−0.0028 (5)	−0.0015 (6)	0.0034 (6)
N2	0.0220 (6)	0.0173 (6)	0.0195 (7)	−0.0007 (4)	0.0010 (5)	−0.0008 (5)
N3	0.0258 (7)	0.0226 (6)	0.0298 (8)	−0.0015 (5)	0.0006 (6)	−0.0012 (6)
C1	0.0190 (7)	0.0201 (7)	0.0172 (8)	−0.0004 (5)	0.0018 (6)	−0.0022 (6)
C2	0.0190 (7)	0.0212 (7)	0.0231 (8)	0.0017 (5)	0.0009 (6)	0.0008 (6)
C3	0.0223 (7)	0.0166 (6)	0.0277 (9)	0.0001 (5)	0.0020 (6)	0.0003 (6)
C4	0.0192 (7)	0.0213 (7)	0.0230 (8)	−0.0025 (5)	0.0033 (6)	−0.0010 (6)
C5	0.0197 (7)	0.0207 (7)	0.0285 (9)	0.0004 (5)	−0.0010 (6)	0.0004 (6)
C6	0.0226 (7)	0.0169 (6)	0.0260 (9)	0.0004 (5)	0.0023 (6)	0.0006 (6)
C7	0.0231 (7)	0.0183 (6)	0.0161 (8)	−0.0008 (5)	0.0029 (6)	−0.0010 (6)
C8	0.0225 (7)	0.0163 (6)	0.0190 (8)	0.0000 (5)	0.0017 (6)	−0.0013 (6)
C9	0.0208 (7)	0.0202 (7)	0.0155 (8)	−0.0011 (5)	0.0028 (5)	−0.0011 (6)
C10	0.0225 (7)	0.0214 (7)	0.0169 (8)	0.0010 (5)	−0.0021 (6)	−0.0056 (6)
C11	0.0241 (7)	0.0260 (7)	0.0233 (9)	−0.0008 (6)	0.0010 (6)	−0.0077 (7)
C12	0.0229 (8)	0.0363 (8)	0.0348 (10)	0.0010 (6)	−0.0002 (7)	−0.0150 (8)
C13	0.0314 (9)	0.0347 (9)	0.0414 (11)	0.0114 (7)	−0.0105 (8)	−0.0154 (8)
C14	0.0424 (9)	0.0238 (7)	0.0323 (10)	0.0099 (7)	−0.0101 (8)	−0.0056 (7)
C15	0.0316 (8)	0.0200 (7)	0.0235 (9)	0.0010 (6)	−0.0023 (7)	−0.0052 (6)
C16	0.0240 (7)	0.0163 (6)	0.0177 (8)	−0.0014 (5)	0.0041 (6)	0.0006 (6)
C17	0.0197 (7)	0.0212 (7)	0.0179 (8)	−0.0025 (5)	0.0015 (6)	−0.0011 (6)
C18	0.0224 (7)	0.0194 (6)	0.0201 (8)	0.0001 (5)	0.0016 (6)	0.0005 (6)
C19	0.0280 (8)	0.0199 (7)	0.0277 (9)	0.0030 (6)	0.0004 (6)	0.0026 (6)

O1—C16	1.3498 (16)	C8—C9	1.3937 (18)
O1—C19	1.4427 (17)	C8—H8A	0.9500
N1—C4	1.3786 (18)	C9—C17	1.405 (2)
N1—H2N1	0.916 (19)	C9—C10	1.4844 (18)
N1—H1N1	0.91 (2)	C10—C15	1.395 (2)
N2—C16	1.3144 (17)	C10—C11	1.398 (2)
N2—C7	1.3589 (17)	C11—C12	1.387 (2)
N3—C18	1.1513 (18)	C11—H11A	0.9500
C1—C2	1.401 (2)	C12—C13	1.388 (3)
C1—C6	1.4032 (18)	C12—H12A	0.9500
C1—C7	1.4718 (18)	C13—C14	1.383 (3)
C2—C3	1.3815 (19)	C13—H13A	0.9500
C2—H2A	0.9500	C14—C15	1.390 (2)
C3—C4	1.4052 (19)	C14—H14A	0.9500
C3—H3A	0.9500	C15—H15A	0.9500
C4—C5	1.401 (2)	C16—C17	1.4094 (19)
C5—C6	1.3811 (19)	C17—C18	1.4317 (19)
C5—H5A	0.9500	C19—H19A	0.9800
C6—H6A	0.9500	C19—H19B	0.9800
C7—C8	1.3968 (19)	C19—H19C	0.9800
C16—O1—C19	116.38 (10)	C15—C10—C11	119.30 (13)
C4—N1—H2N1	116.6 (11)	C15—C10—C9	119.85 (13)
C4—N1—H1N1	117.2 (12)	C11—C10—C9	120.84 (14)
H2N1—N1—H1N1	116.0 (17)	C12—C11—C10	120.01 (15)
C16—N2—C7	118.28 (12)	C12—C11—H11A	120.0
C2—C1—C6	117.41 (12)	C10—C11—H11A	120.0
C2—C1—C7	122.29 (12)	C11—C12—C13	120.37 (16)
C6—C1—C7	120.29 (12)	C11—C12—H12A	119.8
C3—C2—C1	121.80 (13)	C13—C12—H12A	119.8
C3—C2—H2A	119.1	C14—C13—C12	119.87 (15)
C1—C2—H2A	119.1	C14—C13—H13A	120.1
C2—C3—C4	120.24 (13)	C12—C13—H13A	120.1
C2—C3—H3A	119.9	C13—C14—C15	120.24 (16)
C4—C3—H3A	119.9	C13—C14—H14A	119.9
N1—C4—C5	120.41 (13)	C15—C14—H14A	119.9
N1—C4—C3	121.11 (13)	C14—C15—C10	120.19 (16)
C5—C4—C3	118.45 (12)	C14—C15—H15A	119.9
C6—C5—C4	120.69 (13)	C10—C15—H15A	119.9
C6—C5—H5A	119.7	N2—C16—O1	119.59 (12)
C4—C5—H5A	119.7	N2—C16—C17	124.49 (13)
C5—C6—C1	121.41 (13)	O1—C16—C17	115.92 (12)
C5—C6—H6A	119.3	C9—C17—C16	117.80 (12)
C1—C6—H6A	119.3	C9—C17—C18	123.51 (12)
N2—C7—C8	121.10 (12)	C16—C17—C18	118.60 (13)
N2—C7—C1	115.91 (12)	N3—C18—C17	177.54 (15)
C8—C7—C1	122.99 (12)	O1—C19—H19A	109.5
C9—C8—C7	120.85 (12)	O1—C19—H19B	109.5
C9—C8—H8A	119.6	H19A—C19—H19B	109.5
C7—C8—H8A	119.6	O1—C19—H19C	109.5
C8—C9—C17	117.39 (12)	H19A—C19—H19C	109.5
C8—C9—C10	120.36 (12)	H19B—C19—H19C	109.5
C17—C9—C10	122.24 (12)
C6—C1—C2—C3	0.6 (2)	C8—C9—C10—C11	−135.09 (16)
C7—C1—C2—C3	−178.29 (15)	C17—C9—C10—C11	43.4 (2)
C1—C2—C3—C4	−0.5 (2)	C15—C10—C11—C12	0.2 (2)
C2—C3—C4—N1	−178.14 (15)	C9—C10—C11—C12	178.71 (14)
C2—C3—C4—C5	−0.2 (2)	C10—C11—C12—C13	1.1 (2)
N1—C4—C5—C6	178.73 (16)	C11—C12—C13—C14	−1.0 (3)
C3—C4—C5—C6	0.7 (2)	C12—C13—C14—C15	−0.3 (3)
C4—C5—C6—C1	−0.7 (2)	C13—C14—C15—C10	1.6 (3)
C2—C1—C6—C5	0.0 (2)	C11—C10—C15—C14	−1.5 (2)
C7—C1—C6—C5	178.90 (15)	C9—C10—C15—C14	179.94 (14)
C16—N2—C7—C8	2.8 (2)	C7—N2—C16—O1	179.46 (13)
C16—N2—C7—C1	−177.88 (13)	C7—N2—C16—C17	−0.5 (2)
C2—C1—C7—N2	169.00 (15)	C19—O1—C16—N2	−1.2 (2)
C6—C1—C7—N2	−9.9 (2)	C19—O1—C16—C17	178.69 (14)
C2—C1—C7—C8	−11.7 (2)	C8—C9—C17—C16	2.7 (2)
C6—C1—C7—C8	169.48 (15)	C10—C9—C17—C16	−175.87 (14)
N2—C7—C8—C9	−2.3 (2)	C8—C9—C17—C18	−173.75 (14)
C1—C7—C8—C9	178.41 (14)	C10—C9—C17—C18	7.7 (2)
C7—C8—C9—C17	−0.5 (2)	N2—C16—C17—C9	−2.3 (2)
C7—C8—C9—C10	178.05 (14)	O1—C16—C17—C9	177.76 (14)
C8—C9—C10—C15	43.4 (2)	N2—C16—C17—C18	174.30 (15)
C17—C9—C10—C15	−138.05 (15)	O1—C16—C17—C18	−5.6 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H2N1···N3i	0.915 (19)	2.338 (19)	3.2416 (18)	169.5 (19)
N1—H1N1···N3ii	0.91 (2)	2.28 (2)	3.1773 (19)	168 (2)
C11—H11A···Cg3iii	0.95	2.87	3.7667 (17)	158
C19—H19C···Cg2iv	0.98	2.69	3.5156 (17)	142

Table 1

Hydrogen-bond geometry (Å, °)

Cg2 and Cg3 are the centroids of the C1–C6 and C10–C15 rings, respectively.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H2N1⋯N3i	0.915 (19)	2.338 (19)	3.2416 (18)	169.5 (19)
N1—H1N1⋯N3ii	0.91 (2)	2.28 (2)	3.1773 (19)	168 (2)
C11—H11A⋯Cg3iii	0.95	2.87	3.7667 (17)	158
C19—H19C⋯Cg2iv	0.98	2.69	3.5156 (17)	142

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