2-Amino-4-(4-hy-droxy-3,5-dimeth-oxy-phen-yl)-6-phenyl-nicotinonitrile.

In the title compound, C(20)H(17)N(3)O(3), the dihedral angles between the central pyridine ring and the two terminal rings are 15.07 (3) and 43.24 (3)°. The dihedral angle between the two terminal rings is 37.49 (4)° In the crystal, inter-molecular amine N-H⋯N(nitrile) hydrogen-bonding inter-actions form inversion dimers, which are linked into chains through amine N-H⋯O(meth-oxy) hydrogen bonds.

Related literature

For literature on the biological applications of nicotine derivatives, see Hökelek & Necefouglu (1996 ▶, 1999 ▶). For literature on mol­ecules containing the cyano­pyridine moiety and their ability to act as ligands towards transition metal ions and new drugs, see: Alyoubi (2000 ▶); Desai & Shah (2003 ▶); Murata et al. (2004 ▶). For a related structure, see: Fun et al. (1996 ▶).

Experimental

Crystal data

C20H17N3O3

M = 347.37

Triclinic,

a = 8.1320 (16) Å

b = 10.497 (2) Å

c = 10.914 (2) Å

α = 77.28 (3)°

β = 68.36 (3)°

γ = 84.66 (3)°

V = 844.6 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.09 mm−1

T = 293 K

0.20 × 0.10 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 four-circle diffractometer

Absorption correction: ψ scan (semi-empirical, using intensity measurements; North et al., 1968 ▶) T min = 0.981, T max = 0.991

3294 measured reflections

3058 independent reflections

1776 reflections with I > 2σ(I)

R int = 0.031

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.069

wR(F 2) = 0.169

S = 1.01

3058 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.37 e Å−3

Δρmin = −0.25 e Å−3

Data collection: SMART (Bruker, 2004 ▶); cell refinement: SMART; data reduction: SAINT-Plus (Bruker, 2004 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810039127/zs2068sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810039127/zs2068Isup2.hkl

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

C20H17N3O3	Z = 2
Mr = 347.37	F(000) = 364
Triclinic, P1	Dx = 1.366 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1320 (16) Å	Cell parameters from 25 reflections
b = 10.497 (2) Å	θ = 9–12°
c = 10.914 (2) Å	µ = 0.09 mm−1
α = 77.28 (3)°	T = 293 K
β = 68.36 (3)°	Block, colourless
γ = 84.66 (3)°	0.20 × 0.10 × 0.10 mm
V = 844.6 (3) Å3

Enraf–Nonius CAD-4 four-circle diffractometer	1776 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.031
graphite	θmax = 25.3°, θmin = 2.0°
ω/2θ scans	h = 0→9
Absorption correction: ψ scan (semi-empirical (using intensity measurements); North et al., 1968)	k = −12→12
Tmin = 0.981, Tmax = 0.991	l = −12→13
3294 measured reflections	3 standard reflections every 200 reflections
3058 independent reflections	intensity decay: 1%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.169	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.06P)2 + 0.5P] where P = (Fo2 + 2Fc2)/3
3058 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.37 e Å−3
0 restraints	Δρmin = −0.25 e Å−3

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell esds are taken into account in the estimation of distances, angles and torsion angles

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	0.2727 (5)	−0.1198 (2)	1.0345 (3)	0.0793 (13)
O2	0.2820 (4)	−0.0923 (2)	0.5979 (3)	0.0590 (10)
O3	0.2628 (3)	−0.2323 (2)	0.8421 (2)	0.0535 (9)
N1	0.4176 (4)	0.5786 (2)	0.6850 (3)	0.0442 (10)
N2	0.2265 (4)	0.6279 (3)	0.5721 (3)	0.0598 (11)
N3	0.0259 (5)	0.3444 (3)	0.5868 (4)	0.0697 (14)
C1	0.6885 (5)	0.6715 (3)	0.7396 (4)	0.0529 (12)
C2	0.8049 (5)	0.7227 (4)	0.7807 (4)	0.0641 (16)
C3	0.8678 (5)	0.6491 (4)	0.8747 (4)	0.0630 (16)
C4	0.8153 (5)	0.5217 (4)	0.9273 (4)	0.0600 (14)
C5	0.6991 (5)	0.4705 (3)	0.8868 (4)	0.0512 (11)
C6	0.6330 (4)	0.5439 (3)	0.7930 (3)	0.0433 (11)
C7	0.5053 (4)	0.4907 (3)	0.7504 (3)	0.0413 (11)
C8	0.4765 (5)	0.3580 (3)	0.7747 (3)	0.0459 (11)
C9	0.3556 (4)	0.3108 (3)	0.7332 (3)	0.0429 (11)
C10	0.2667 (4)	0.4028 (3)	0.6648 (3)	0.0436 (11)
C11	0.3040 (4)	0.5356 (3)	0.6404 (3)	0.0423 (11)
C12	0.3250 (4)	0.1688 (3)	0.7618 (4)	0.0453 (11)
C13	0.3115 (5)	0.0937 (3)	0.8868 (4)	0.0528 (14)
C14	0.2894 (5)	−0.0402 (3)	0.9136 (4)	0.0496 (11)
C15	0.2843 (4)	−0.1017 (3)	0.8137 (3)	0.0395 (11)
C16	0.2939 (4)	−0.0246 (3)	0.6902 (3)	0.0428 (11)
C17	0.3166 (4)	0.1081 (3)	0.6633 (3)	0.0438 (11)
C18	0.1322 (5)	0.3671 (3)	0.6226 (4)	0.0477 (11)
C19	0.2036 (7)	−0.0690 (5)	1.1506 (5)	0.096 (2)
C20	0.2425 (5)	−0.0191 (4)	0.4867 (4)	0.0641 (16)
H1B	0.64720	0.72290	0.67560	0.0630*
H2A	0.25100	0.70880	0.55940	0.0720*
H2B	0.15250	0.60600	0.54110	0.0720*
H2C	0.84120	0.80870	0.74410	0.0770*
H3A	0.94520	0.68490	0.90260	0.0750*
H3B	0.25970	−0.26200	0.91900	0.0800*
H4A	0.85840	0.47030	0.99020	0.0720*
H5A	0.66400	0.38430	0.92330	0.0620*
H8A	0.53890	0.29950	0.81940	0.0550*
H13A	0.31720	0.13370	0.95320	0.0640*
H17A	0.32640	0.15730	0.57890	0.0520*
H19A	0.20010	−0.13640	1.22690	0.1430*
H19B	0.08590	−0.03610	1.16140	0.1430*
H19C	0.27690	0.00070	1.14390	0.1430*
H20A	0.23850	−0.07660	0.43050	0.0970*
H20B	0.33230	0.04490	0.43580	0.0970*
H20C	0.12980	0.02400	0.51810	0.0970*

	U11	U22	U33	U12	U13	U23
O1	0.144 (3)	0.0382 (15)	0.0645 (19)	0.0084 (16)	−0.051 (2)	−0.0079 (13)
O2	0.092 (2)	0.0321 (13)	0.0648 (17)	−0.0016 (13)	−0.0419 (16)	−0.0090 (12)
O3	0.0714 (17)	0.0284 (12)	0.0605 (16)	−0.0096 (11)	−0.0277 (14)	0.0025 (11)
N1	0.0520 (18)	0.0311 (14)	0.0546 (18)	−0.0009 (12)	−0.0285 (15)	−0.0023 (13)
N2	0.078 (2)	0.0320 (16)	0.088 (2)	−0.0033 (15)	−0.057 (2)	−0.0006 (15)
N3	0.079 (2)	0.055 (2)	0.098 (3)	−0.0013 (17)	−0.060 (2)	−0.0120 (19)
C1	0.059 (2)	0.043 (2)	0.061 (2)	−0.0062 (17)	−0.033 (2)	0.0034 (17)
C2	0.069 (3)	0.042 (2)	0.086 (3)	−0.0160 (19)	−0.038 (2)	0.002 (2)
C3	0.054 (2)	0.062 (3)	0.083 (3)	−0.015 (2)	−0.036 (2)	−0.009 (2)
C4	0.055 (2)	0.057 (2)	0.075 (3)	−0.0006 (19)	−0.040 (2)	0.002 (2)
C5	0.056 (2)	0.0345 (18)	0.067 (2)	−0.0051 (16)	−0.032 (2)	0.0010 (17)
C6	0.040 (2)	0.0341 (17)	0.056 (2)	−0.0037 (15)	−0.0184 (17)	−0.0061 (16)
C7	0.047 (2)	0.0307 (17)	0.048 (2)	0.0006 (15)	−0.0227 (17)	−0.0021 (15)
C8	0.053 (2)	0.0314 (17)	0.061 (2)	0.0061 (15)	−0.0336 (19)	−0.0043 (16)
C9	0.053 (2)	0.0290 (17)	0.051 (2)	0.0014 (15)	−0.0240 (18)	−0.0082 (15)
C10	0.049 (2)	0.0335 (17)	0.053 (2)	−0.0024 (15)	−0.0237 (18)	−0.0080 (15)
C11	0.048 (2)	0.0345 (18)	0.049 (2)	0.0027 (15)	−0.0250 (18)	−0.0056 (15)
C12	0.049 (2)	0.0311 (17)	0.061 (2)	0.0032 (15)	−0.0280 (19)	−0.0067 (16)
C13	0.069 (3)	0.0368 (19)	0.063 (2)	0.0020 (17)	−0.037 (2)	−0.0086 (17)
C14	0.064 (2)	0.0323 (18)	0.056 (2)	0.0017 (16)	−0.030 (2)	−0.0019 (17)
C15	0.0369 (19)	0.0266 (16)	0.051 (2)	−0.0017 (13)	−0.0140 (16)	−0.0021 (15)
C16	0.043 (2)	0.0313 (17)	0.055 (2)	0.0010 (14)	−0.0181 (17)	−0.0102 (16)
C17	0.050 (2)	0.0322 (17)	0.051 (2)	−0.0021 (15)	−0.0241 (18)	−0.0011 (15)
C18	0.060 (2)	0.0331 (18)	0.058 (2)	0.0024 (16)	−0.032 (2)	−0.0077 (16)
C19	0.113 (4)	0.086 (4)	0.071 (3)	0.020 (3)	−0.026 (3)	−0.001 (3)
C20	0.077 (3)	0.057 (2)	0.075 (3)	0.000 (2)	−0.048 (2)	−0.011 (2)

O1—C14	1.364 (5)	C10—C11	1.401 (5)
O1—C19	1.387 (6)	C10—C18	1.440 (5)
O2—C16	1.389 (4)	C12—C17	1.389 (5)
O2—C20	1.413 (5)	C12—C13	1.388 (5)
O3—C15	1.350 (4)	C13—C14	1.386 (5)
O3—H3B	0.8200	C14—C15	1.398 (5)
N1—C7	1.354 (4)	C15—C16	1.390 (4)
N1—C11	1.342 (5)	C16—C17	1.374 (5)
N2—C11	1.344 (5)	C1—H1B	0.9300
N3—C18	1.134 (6)	C2—H2C	0.9300
N2—H2B	0.8600	C3—H3A	0.9300
N2—H2A	0.8600	C4—H4A	0.9300
C1—C2	1.378 (6)	C5—H5A	0.9300
C1—C6	1.383 (5)	C8—H8A	0.9300
C2—C3	1.370 (6)	C13—H13A	0.9300
C3—C4	1.374 (6)	C17—H17A	0.9300
C4—C5	1.373 (6)	C19—H19A	0.9600
C5—C6	1.383 (5)	C19—H19B	0.9600
C6—C7	1.478 (5)	C19—H19C	0.9600
C7—C8	1.385 (5)	C20—H20A	0.9600
C8—C9	1.391 (5)	C20—H20B	0.9600
C9—C10	1.401 (5)	C20—H20C	0.9600
C9—C12	1.479 (5)
C14—O1—C19	119.3 (3)	O3—C15—C16	122.4 (3)
C16—O2—C20	117.4 (3)	C14—C15—C16	118.3 (3)
C15—O3—H3B	109.00	O2—C16—C15	114.9 (3)
C7—N1—C11	119.1 (3)	C15—C16—C17	121.4 (3)
C11—N2—H2B	120.00	O2—C16—C17	123.7 (3)
H2A—N2—H2B	120.00	C12—C17—C16	120.1 (3)
C11—N2—H2A	120.00	N3—C18—C10	177.1 (4)
C2—C1—C6	120.3 (4)	C2—C1—H1B	120.00
C1—C2—C3	121.1 (4)	C6—C1—H1B	120.00
C2—C3—C4	119.2 (4)	C1—C2—H2C	119.00
C3—C4—C5	119.9 (4)	C3—C2—H2C	119.00
C4—C5—C6	121.7 (3)	C2—C3—H3A	120.00
C5—C6—C7	122.2 (3)	C4—C3—H3A	120.00
C1—C6—C5	117.9 (3)	C3—C4—H4A	120.00
C1—C6—C7	119.9 (3)	C5—C4—H4A	120.00
C6—C7—C8	122.3 (3)	C4—C5—H5A	119.00
N1—C7—C8	121.2 (3)	C6—C5—H5A	119.00
N1—C7—C6	116.5 (3)	C7—C8—H8A	120.00
C7—C8—C9	121.0 (3)	C9—C8—H8A	119.00
C8—C9—C10	117.2 (3)	C12—C13—H13A	120.00
C8—C9—C12	120.1 (3)	C14—C13—H13A	120.00
C10—C9—C12	122.7 (3)	C12—C17—H17A	120.00
C9—C10—C11	119.3 (3)	C16—C17—H17A	120.00
C9—C10—C18	122.6 (3)	O1—C19—H19A	109.00
C11—C10—C18	118.0 (3)	O1—C19—H19B	109.00
N1—C11—C10	122.1 (3)	O1—C19—H19C	109.00
N2—C11—C10	122.0 (3)	H19A—C19—H19B	109.00
N1—C11—N2	115.9 (3)	H19A—C19—H19C	109.00
C13—C12—C17	119.2 (3)	H19B—C19—H19C	109.00
C9—C12—C13	119.9 (3)	O2—C20—H20A	109.00
C9—C12—C17	120.9 (3)	O2—C20—H20B	110.00
C12—C13—C14	120.6 (3)	O2—C20—H20C	110.00
O1—C14—C15	116.0 (3)	H20A—C20—H20B	109.00
C13—C14—C15	120.2 (3)	H20A—C20—H20C	109.00
O1—C14—C13	123.8 (3)	H20B—C20—H20C	109.00
O3—C15—C14	119.2 (3)
C19—O1—C14—C13	27.2 (7)	C12—C9—C10—C11	−179.4 (3)
C19—O1—C14—C15	−153.2 (4)	C12—C9—C10—C18	3.1 (5)
C20—O2—C16—C15	163.1 (3)	C8—C9—C12—C13	42.3 (5)
C20—O2—C16—C17	−18.0 (5)	C8—C9—C12—C17	−135.1 (4)
C11—N1—C7—C6	178.0 (3)	C10—C9—C12—C13	−137.6 (4)
C11—N1—C7—C8	−1.6 (5)	C10—C9—C12—C17	45.0 (5)
C7—N1—C11—N2	−177.7 (3)	C9—C10—C11—N1	−2.6 (5)
C7—N1—C11—C10	3.1 (5)	C9—C10—C11—N2	178.1 (3)
C6—C1—C2—C3	−0.1 (6)	C18—C10—C11—N1	175.0 (3)
C2—C1—C6—C5	−0.6 (5)	C18—C10—C11—N2	−4.3 (5)
C2—C1—C6—C7	178.7 (3)	C9—C12—C13—C14	−177.6 (4)
C1—C2—C3—C4	0.8 (6)	C17—C12—C13—C14	−0.2 (6)
C2—C3—C4—C5	−1.0 (6)	C9—C12—C17—C16	177.9 (3)
C3—C4—C5—C6	0.3 (6)	C13—C12—C17—C16	0.5 (5)
C4—C5—C6—C1	0.5 (6)	C12—C13—C14—O1	−179.1 (4)
C4—C5—C6—C7	−178.9 (3)	C12—C13—C14—C15	1.4 (6)
C1—C6—C7—N1	−15.1 (5)	O1—C14—C15—O3	0.4 (5)
C1—C6—C7—C8	164.5 (3)	O1—C14—C15—C16	177.6 (4)
C5—C6—C7—N1	164.2 (3)	C13—C14—C15—O3	179.9 (4)
C5—C6—C7—C8	−16.2 (5)	C13—C14—C15—C16	−2.8 (6)
N1—C7—C8—C9	−0.3 (5)	O3—C15—C16—O2	−0.8 (5)
C6—C7—C8—C9	−179.9 (3)	O3—C15—C16—C17	−179.7 (3)
C7—C8—C9—C10	0.8 (5)	C14—C15—C16—O2	−177.9 (3)
C7—C8—C9—C12	−179.2 (3)	C14—C15—C16—C17	3.2 (5)
C8—C9—C10—C11	0.7 (4)	O2—C16—C17—C12	179.2 (3)
C8—C9—C10—C18	−176.8 (3)	C15—C16—C17—C12	−2.0 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···O2i	0.86	2.27	3.101 (4)	162
N2—H2B···N3ii	0.86	2.31	3.098 (5)	152
O3—H3B···O1	0.82	2.19	2.654 (4)	116
C1—H1B···N1	0.93	2.47	2.790 (5)	100

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯O2i	0.86	2.27	3.101 (4)	162
N2—H2B⋯N3ii	0.86	2.31	3.098 (5)	152

Symmetry codes: (i) ; (ii) .