2-Amino-6-(naphthalen-1-yl)-4-phenyl-pyridine-3-carbonitrile.

In the title compound, C(22)H(15)N(3), the naphthyl ring system makes dihedral angles of 67.40 (2) and 59.80 (3)° with the pyridyl and phenyl rings, respectively. In the crystal, the mol-ecules are connected via inter-molecular N-H⋯N hydrogen bonds, forming a three-dimensional network.

Related literature

For the synthetic procedure, see: Mantri et al. (2008 ▶). For related structures, see: Mkhalid et al. (2006 ▶). For general background, see: Moreau et al. (1999 ▶).

Experimental

Crystal data

C22H15N3

M = 321.37

Monoclinic,

a = 11.799 (2) Å

b = 17.284 (3) Å

c = 17.492 (4) Å

β = 98.26 (3)°

V = 3530.2 (12) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 293 K

0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer

Absorption correction: ψ scan (North et al., 1968 ▶) T min = 0.979, T max = 0.993

3367 measured reflections

3240 independent reflections

1717 reflections with I > 2σ(I)

R int = 0.030

3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F 2 > 2σ(F 2)] = 0.066

wR(F 2) = 0.180

S = 1.01

3240 reflections

208 parameters

1 restraint

H-atom parameters constrained

Δρmax = 0.13 e Å−3

Δρmin = −0.13 e Å−3

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994) ▶; cell refinement: CAD-4 EXPRESS ▶; data reduction: XCAD4 (Harms & Wocadlo,1995 ▶); 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/S1600536811002765/bv2172sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811002765/bv2172Isup2.hkl

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

C22H15N3	F(000) = 1344
Mr = 321.37	Dx = 1.209 Mg m−3
Monoclinic, C2/c	Melting point: 438 K
Hall symbol: -C 2yc	Mo Kα radiation, λ = 0.71073 Å
a = 11.799 (2) Å	Cell parameters from 25 reflections
b = 17.284 (3) Å	θ = 9–12°
c = 17.492 (4) Å	µ = 0.07 mm−1
β = 98.26 (3)°	T = 293 K
V = 3530.2 (12) Å3	Block, colorless
Z = 8	0.30 × 0.20 × 0.10 mm

Enraf–Nonius CAD-4 diffractometer	1717 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.030
graphite	θmax = 25.4°, θmin = 2.1°
ω/2θ scans	h = 0→14
Absorption correction: ψ scan (North et al., 1968)	k = 0→20
Tmin = 0.979, Tmax = 0.993	l = −21→20
3367 measured reflections	3 standard reflections every 200 reflections
3240 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)] = 0.066	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.180	H-atom parameters constrained
S = 1.01	w = 1/[σ2(Fo2) + (0.050P)2 + 3.8P] where P = (Fo2 + 2Fc2)/3
3240 reflections	(Δ/σ)max < 0.001
208 parameters	Δρmax = 0.13 e Å−3
1 restraint	Δρmin = −0.13 e Å−3

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
N1	0.3542 (2)	0.1427 (2)	0.69970 (17)	0.1156 (13)
C1	0.0883 (3)	0.0618 (2)	0.4510 (2)	0.1035 (13)
H1B	0.1191	0.0169	0.4749	0.124*
N2	0.4951 (2)	0.08860 (18)	0.64401 (14)	0.1002 (10)
H2A	0.5373	0.0942	0.6880	0.120*
H2B	0.5231	0.0682	0.6060	0.120*
C2	0.0113 (4)	0.0532 (3)	0.3842 (3)	0.1361 (17)
H2C	−0.0090	0.0049	0.3630	0.163*
N3	0.3832 (3)	0.0285 (2)	0.45458 (14)	0.1147 (13)
C3	−0.0341 (4)	0.1219 (4)	0.3506 (3)	0.1341 (17)
H3A	−0.0854	0.1198	0.3050	0.161*
C4	−0.0050 (5)	0.1915 (4)	0.3830 (3)	0.1376 (17)
H4A	−0.0356	0.2367	0.3596	0.165*
C5	0.0720 (4)	0.1953 (3)	0.4525 (3)	0.1277 (16)
H5A	0.0882	0.2428	0.4765	0.153*
C6	0.1229 (3)	0.1301 (3)	0.4846 (2)	0.0905 (11)
C7	0.2017 (3)	0.1324 (2)	0.55800 (18)	0.0783 (9)
C8	0.1731 (3)	0.1668 (2)	0.6244 (2)	0.0958 (12)
H8A	0.1027	0.1917	0.6214	0.115*
C9	0.2443 (3)	0.1661 (3)	0.6957 (2)	0.1076 (13)
C10	0.3872 (3)	0.1114 (2)	0.63484 (18)	0.0819 (10)
C11	0.3122 (3)	0.10289 (18)	0.56551 (16)	0.0704 (8)
C12	0.2128 (3)	0.1874 (3)	0.7756 (3)	0.1025 (13)
C13	0.1864 (3)	0.2620 (3)	0.7827 (2)	0.0940 (12)
C14	0.1949 (4)	0.3212 (3)	0.7187 (2)	0.1173 (15)
H14A	0.2117	0.3065	0.6704	0.141*
C15	0.1767 (4)	0.3959 (3)	0.7358 (3)	0.115
H15A	0.1869	0.4339	0.6999	0.138*
C16	0.1480 (4)	0.4143 (3)	0.7956 (3)	0.114
H16A	0.1390	0.4673	0.8020	0.137*
C17	0.1279 (3)	0.3736 (2)	0.8516 (2)	0.092
H17A	0.0958	0.3958	0.8918	0.110*
C18	0.1548 (3)	0.2920 (2)	0.8532 (2)	0.0879 (11)
C19	0.1452 (3)	0.2408 (3)	0.9156 (3)	0.1128 (14)
H19A	0.1199	0.2579	0.9607	0.135*
C20	0.1769 (4)	0.1602 (3)	0.9057 (3)	0.1198 (14)
H20A	0.1759	0.1232	0.9442	0.144*
C21	0.2098 (4)	0.1426 (3)	0.8311 (3)	0.1124 (14)
H21A	0.2313	0.0916	0.8237	0.135*
C22	0.3531 (3)	0.0621 (2)	0.50320 (16)	0.0783 (10)

	U11	U22	U33	U12	U13	U23
N1	0.0609 (18)	0.192 (3)	0.099 (2)	−0.014 (2)	0.0263 (16)	−0.087 (2)
C1	0.109 (3)	0.111 (3)	0.077 (2)	0.000 (2)	−0.035 (2)	0.003 (2)
N2	0.0698 (19)	0.171 (3)	0.0560 (16)	0.0290 (19)	−0.0046 (13)	−0.0224 (17)
C2	0.162 (5)	0.141 (4)	0.092 (3)	−0.015 (4)	−0.026 (3)	−0.030 (3)
N3	0.134 (3)	0.167 (3)	0.0374 (15)	0.083 (2)	−0.0051 (16)	−0.0141 (17)
C3	0.124 (4)	0.165 (5)	0.099 (3)	0.035 (4)	−0.032 (3)	−0.007 (4)
C4	0.121 (4)	0.136 (5)	0.151 (5)	0.008 (3)	0.002 (4)	0.031 (4)
C5	0.103 (3)	0.123 (4)	0.150 (4)	0.016 (3)	−0.004 (3)	−0.015 (3)
C6	0.067 (2)	0.117 (3)	0.084 (2)	0.024 (2)	0.0001 (18)	−0.036 (2)
C7	0.060 (2)	0.102 (3)	0.072 (2)	0.0134 (18)	0.0038 (16)	−0.0270 (18)
C8	0.074 (2)	0.117 (3)	0.094 (3)	0.028 (2)	0.005 (2)	−0.040 (2)
C9	0.084 (3)	0.140 (4)	0.101 (3)	0.011 (2)	0.023 (2)	−0.042 (3)
C10	0.069 (2)	0.114 (3)	0.0649 (19)	0.007 (2)	0.0169 (15)	−0.0229 (19)
C11	0.075 (2)	0.081 (2)	0.0555 (17)	0.0086 (17)	0.0104 (14)	−0.0132 (15)
C12	0.080 (3)	0.119 (4)	0.105 (3)	−0.004 (3)	0.006 (2)	−0.028 (3)
C13	0.067 (2)	0.119 (3)	0.092 (3)	0.002 (2)	−0.0036 (19)	−0.042 (3)
C14	0.112 (3)	0.154 (4)	0.077 (3)	0.022 (3)	−0.016 (2)	−0.032 (3)
C15	0.115	0.115	0.115	0.000	0.016	0.000
C16	0.114	0.114	0.114	0.000	0.016	0.000
C17	0.092	0.092	0.092	0.000	0.013	0.000
C18	0.0534 (19)	0.123 (3)	0.081 (2)	0.0281 (19)	−0.0125 (17)	−0.038 (2)
C19	0.083 (3)	0.151 (4)	0.107 (3)	−0.019 (3)	0.020 (2)	−0.023 (3)
C20	0.114 (3)	0.131 (4)	0.114 (4)	−0.032 (3)	0.016 (3)	0.014 (3)
C21	0.095 (3)	0.133 (4)	0.113 (4)	−0.024 (3)	0.026 (3)	−0.028 (3)
C22	0.082 (2)	0.120 (3)	0.0287 (14)	0.030 (2)	−0.0034 (14)	0.0008 (17)

N1—C9	1.351 (4)	C9—C12	1.542 (5)
N1—C10	1.363 (4)	C10—C11	1.403 (4)
C1—C6	1.356 (5)	C11—C22	1.439 (4)
C1—C2	1.382 (5)	C12—C21	1.247 (5)
C1—H1B	0.9300	C12—C13	1.337 (5)
N2—C10	1.320 (4)	C13—C18	1.435 (5)
N2—H2A	0.8600	C13—C14	1.532 (6)
N2—H2B	0.8600	C14—C15	1.349 (5)
C2—C3	1.397 (6)	C14—H14A	0.9300
C2—H2C	0.9300	C15—C16	1.189 (5)
N3—C22	1.128 (4)	C15—H15A	0.9300
C3—C4	1.353 (6)	C16—C17	1.255 (5)
C3—H3A	0.9300	C16—H16A	0.9300
C4—C5	1.410 (6)	C17—C18	1.444 (5)
C4—H4A	0.9300	C17—H17A	0.9300
C5—C6	1.359 (5)	C18—C19	1.422 (5)
C5—H5A	0.9300	C19—C20	1.459 (6)
C6—C7	1.473 (5)	C19—H19A	0.9300
C7—C11	1.389 (4)	C20—C21	1.446 (6)
C7—C8	1.389 (4)	C20—H20A	0.9300
C8—C9	1.399 (5)	C21—H21A	0.9300
C8—H8A	0.9300
C9—N1—C10	117.5 (3)	C7—C11—C10	120.7 (3)
C6—C1—C2	125.6 (4)	C7—C11—C22	121.4 (3)
C6—C1—H1B	117.2	C10—C11—C22	117.9 (3)
C2—C1—H1B	117.2	C21—C12—C13	119.6 (5)
C10—N2—H2A	120.0	C21—C12—C9	126.5 (5)
C10—N2—H2B	120.0	C13—C12—C9	113.9 (5)
H2A—N2—H2B	120.0	C12—C13—C18	121.4 (5)
C1—C2—C3	115.4 (4)	C12—C13—C14	122.4 (4)
C1—C2—H2C	122.3	C18—C13—C14	116.1 (4)
C3—C2—H2C	122.3	C15—C14—C13	116.6 (4)
C4—C3—C2	121.4 (4)	C15—C14—H14A	121.7
C4—C3—H3A	119.3	C13—C14—H14A	121.7
C2—C3—H3A	119.3	C16—C15—C14	121.8 (5)
C3—C4—C5	119.7 (5)	C16—C15—H15A	119.1
C3—C4—H4A	120.2	C14—C15—H15A	119.1
C5—C4—H4A	120.2	C15—C16—C17	130.1 (5)
C6—C5—C4	120.7 (5)	C15—C16—H16A	114.9
C6—C5—H5A	119.7	C17—C16—H16A	114.9
C4—C5—H5A	119.7	C16—C17—C18	119.9 (4)
C1—C6—C5	117.0 (4)	C16—C17—H17A	120.1
C1—C6—C7	121.0 (4)	C18—C17—H17A	120.1
C5—C6—C7	121.6 (4)	C19—C18—C13	119.6 (4)
C11—C7—C8	114.5 (3)	C19—C18—C17	125.5 (4)
C11—C7—C6	122.6 (3)	C13—C18—C17	114.7 (4)
C8—C7—C6	122.8 (3)	C18—C19—C20	116.9 (4)
C7—C8—C9	123.7 (3)	C18—C19—H19A	121.5
C7—C8—H8A	118.2	C20—C19—H19A	121.5
C9—C8—H8A	118.2	C21—C20—C19	114.6 (4)
N1—C9—C8	119.9 (3)	C21—C20—H20A	122.7
N1—C9—C12	112.2 (4)	C19—C20—H20A	122.7
C8—C9—C12	127.9 (3)	C12—C21—C20	127.8 (5)
N2—C10—N1	113.8 (3)	C12—C21—H21A	116.1
N2—C10—C11	123.5 (3)	C20—C21—H21A	116.1
N1—C10—C11	122.8 (3)	N3—C22—C11	178.1 (4)
C6—C1—C2—C3	−0.8 (7)	N1—C9—C12—C21	−64.7 (6)
C1—C2—C3—C4	−1.1 (8)	C8—C9—C12—C21	113.5 (6)
C2—C3—C4—C5	−0.5 (9)	N1—C9—C12—C13	115.7 (4)
C3—C4—C5—C6	4.2 (8)	C8—C9—C12—C13	−66.2 (6)
C2—C1—C6—C5	4.3 (7)	C21—C12—C13—C18	0.2 (6)
C2—C1—C6—C7	177.2 (4)	C9—C12—C13—C18	179.9 (3)
C4—C5—C6—C1	−5.9 (7)	C21—C12—C13—C14	176.4 (4)
C4—C5—C6—C7	−178.7 (4)	C9—C12—C13—C14	−3.9 (5)
C1—C6—C7—C11	62.2 (5)	C12—C13—C14—C15	−173.7 (4)
C5—C6—C7—C11	−125.2 (4)	C18—C13—C14—C15	2.7 (5)
C1—C6—C7—C8	−120.2 (4)	C13—C14—C15—C16	−4.9 (7)
C5—C6—C7—C8	52.3 (6)	C14—C15—C16—C17	−1.0 (8)
C11—C7—C8—C9	−5.7 (6)	C15—C16—C17—C18	8.9 (8)
C6—C7—C8—C9	176.6 (4)	C12—C13—C18—C19	−3.5 (5)
C10—N1—C9—C8	−7.9 (6)	C14—C13—C18—C19	−179.9 (3)
C10—N1—C9—C12	170.4 (4)	C12—C13—C18—C17	−179.6 (3)
C7—C8—C9—N1	11.3 (7)	C14—C13—C18—C17	4.0 (4)
C7—C8—C9—C12	−166.7 (4)	C16—C17—C18—C19	174.6 (4)
C9—N1—C10—N2	−178.7 (4)	C16—C17—C18—C13	−9.6 (5)
C9—N1—C10—C11	−0.1 (6)	C13—C18—C19—C20	4.4 (5)
C8—C7—C11—C10	−2.5 (5)	C17—C18—C19—C20	−179.9 (3)
C6—C7—C11—C10	175.2 (4)	C18—C19—C20—C21	−2.5 (5)
C8—C7—C11—C22	176.9 (3)	C13—C12—C21—C20	2.0 (7)
C6—C7—C11—C22	−5.4 (5)	C9—C12—C21—C20	−177.7 (4)
N2—C10—C11—C7	−176.0 (3)	C19—C20—C21—C12	−0.8 (7)
N1—C10—C11—C7	5.5 (6)	C7—C11—C22—N3	−68 (11)
N2—C10—C11—C22	4.7 (5)	C10—C11—C22—N3	111 (11)
N1—C10—C11—C22	−173.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2A···N1i	0.86	2.34	3.180 (4)	165
N2—H2B···N3ii	0.86	2.34	3.138 (4)	154

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2A⋯N1i	0.86	2.34	3.180 (4)	165
N2—H2B⋯N3ii	0.86	2.34	3.138 (4)	154

Symmetry codes: (i) ; (ii) .