6-Meth-oxy-4-(2,4,5-tri-meth-oxy-phen-yl)-2,2'-bi-pyridine-5-carbo-nitrile.

In the title 3-cyano-pyridine derivative, C21H19N3O4, the 3-cyano-substituted pyridine ring forms dihedral angles of 2.35 (5) and 41.60 (5)° with the unsubstituted pyridine and 2,4,5-trimeth-oxy-substituted benzene rings, respectively. The dihedral angle between the unsubstituted pyridine and benzene rings is 39.84 (5)°. The meth-oxy groups form Cmeth-yl-O-C-(C,N) torsion angles in the range 0.80 (15)-11.45 (15)°. In the crystal, mol-ecules related by 21 screw axes are linked by weak C-H⋯N hydrogen bonds along [010]. In addition, weak C-H⋯π inter-actions and π-π stacking inter-actions between pyridine rings, with a centroid-centroid distance of 3.6448 (6) Å, are observed.

Related literature

For the synthesis and applications of 3-cyano­pyridine 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 ▶); Suwunwong et al. (2011 ▶); Zhou et al. (2006 ▶). For related structures, see: Chantrapromma et al. (2010 ▶); Suwunwong et al. (2012 ▶). For standard bond-length data, see: Allen et al. (1987 ▶).

Experimental

Crystal data

C21H19N3O4

M = 377.39

Monoclinic,

a = 14.9967 (3) Å

b = 7.4039 (2) Å

c = 17.5795 (4) Å

β = 114.080 (1)°

V = 1782.06 (7) Å3

Z = 4

Mo Kα radiation

μ = 0.10 mm−1

T = 100 K

0.60 × 0.29 × 0.23 mm

Data collection

Bruker APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.943, T max = 0.977

20323 measured reflections

5182 independent reflections

4386 reflections with I > 2σ(I)

R int = 0.030

Refinement

R[F 2 > 2σ(F 2)] = 0.042

wR(F 2) = 0.116

S = 1.03

5182 reflections

257 parameters

H-atom parameters constrained

Δρmax = 0.40 e Å−3

Δρmin = −0.31 e Å−3

Data collection: APEX2 (Bruker, 2005 ▶); cell refinement: SAINT (Bruker, 2005 ▶); 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/S1600536813023891/lh5641sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536813023891/lh5641Isup2.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536813023891/lh5641Isup3.cml

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

C21H19N3O4	F(000) = 792
Mr = 377.39	Dx = 1.407 Mg m−3
Monoclinic, P21/c	Melting point = 506–507 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 14.9967 (3) Å	Cell parameters from 5182 reflections
b = 7.4039 (2) Å	θ = 2.4–30.0°
c = 17.5795 (4) Å	µ = 0.10 mm−1
β = 114.080 (1)°	T = 100 K
V = 1782.06 (7) Å3	Block, colorless
Z = 4	0.60 × 0.29 × 0.23 mm

Bruker APEXII CCD area-detector diffractometer	5182 independent reflections
Radiation source: sealed tube	4386 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.030
φ and ω scans	θmax = 30.0°, θmin = 2.4°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −21→21
Tmin = 0.943, Tmax = 0.977	k = −10→10
20323 measured reflections	l = −22→24

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.116	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0629P)2 + 0.5246P] where P = (Fo2 + 2Fc2)/3
5182 reflections	(Δ/σ)max = 0.001
257 parameters	Δρmax = 0.40 e Å−3
0 restraints	Δρmin = −0.31 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	0.08878 (6)	0.11337 (11)	−0.09750 (5)	0.01663 (17)
O2	0.21018 (6)	0.46941 (10)	0.24541 (5)	0.01852 (17)
O3	0.48961 (5)	0.12019 (10)	0.42643 (5)	0.01676 (17)
O4	0.44854 (6)	−0.13384 (11)	0.31664 (5)	0.02014 (18)
N1	−0.10990 (7)	0.40828 (13)	0.10405 (6)	0.01619 (19)
N2	−0.00502 (6)	0.22953 (12)	−0.03257 (5)	0.01373 (18)
N3	0.32255 (7)	0.04540 (15)	0.03661 (7)	0.0231 (2)
C1	−0.19408 (8)	0.48087 (15)	0.09883 (7)	0.0174 (2)
H1A	−0.1982	0.5191	0.1489	0.021*
C2	−0.27560 (8)	0.50345 (15)	0.02446 (7)	0.0176 (2)
H2A	−0.3340	0.5543	0.0239	0.021*
C3	−0.26961 (8)	0.44990 (16)	−0.04895 (7)	0.0187 (2)
H3A	−0.3240	0.4640	−0.1009	0.022*
C4	−0.18290 (8)	0.37531 (15)	−0.04529 (7)	0.0160 (2)
H4A	−0.1768	0.3381	−0.0947	0.019*
C5	−0.10496 (7)	0.35617 (13)	0.03249 (6)	0.01291 (19)
C6	−0.01002 (7)	0.27984 (13)	0.03969 (6)	0.01266 (19)
C7	0.06802 (7)	0.26430 (14)	0.11670 (6)	0.0139 (2)
H7A	0.0605	0.2991	0.1658	0.017*
C8	0.15792 (7)	0.19739 (13)	0.12237 (6)	0.01287 (19)
C9	0.16324 (7)	0.14605 (14)	0.04744 (6)	0.01298 (19)
C10	0.07884 (7)	0.16495 (14)	−0.02772 (6)	0.01309 (19)
C11	0.24309 (7)	0.18194 (14)	0.20364 (6)	0.01303 (19)
C12	0.26734 (7)	0.31794 (14)	0.26440 (6)	0.0139 (2)
C13	0.34940 (7)	0.30003 (14)	0.33993 (6)	0.0140 (2)
H13A	0.3648	0.3925	0.3808	0.017*
C14	0.40836 (7)	0.14785 (14)	0.35544 (6)	0.01330 (19)
C15	0.38513 (7)	0.00954 (14)	0.29540 (7)	0.0144 (2)
C16	0.30335 (7)	0.02751 (14)	0.22149 (6)	0.01395 (19)
H16A	0.2872	−0.0669	0.1815	0.017*
C17	0.00747 (8)	0.15056 (17)	−0.17547 (7)	0.0197 (2)
H17A	0.0223	0.1065	−0.2216	0.030*
H17B	−0.0042	0.2811	−0.1813	0.030*
H17C	−0.0510	0.0894	−0.1766	0.030*
C18	0.25207 (8)	0.08862 (14)	0.04235 (7)	0.0156 (2)
C19	0.22509 (8)	0.59686 (15)	0.31086 (7)	0.0179 (2)
H19A	0.1754	0.6919	0.2905	0.027*
H19B	0.2901	0.6508	0.3286	0.027*
H19C	0.2199	0.5350	0.3582	0.027*
C20	0.51581 (8)	0.25983 (15)	0.48834 (7)	0.0176 (2)
H20A	0.5748	0.2240	0.5366	0.026*
H20B	0.4622	0.2786	0.5057	0.026*
H20C	0.5284	0.3722	0.4649	0.026*
C21	0.43561 (9)	−0.26391 (16)	0.25325 (8)	0.0222 (2)
H21A	0.4884	−0.3531	0.2740	0.033*
H21B	0.4369	−0.2032	0.2042	0.033*
H21C	0.3727	−0.3249	0.2380	0.033*

	U11	U22	U33	U12	U13	U23
O1	0.0182 (4)	0.0217 (4)	0.0112 (3)	0.0019 (3)	0.0073 (3)	−0.0016 (3)
O2	0.0206 (4)	0.0147 (4)	0.0154 (4)	0.0058 (3)	0.0025 (3)	−0.0031 (3)
O3	0.0152 (3)	0.0164 (4)	0.0146 (4)	0.0022 (3)	0.0019 (3)	−0.0016 (3)
O4	0.0214 (4)	0.0175 (4)	0.0186 (4)	0.0082 (3)	0.0052 (3)	−0.0020 (3)
N1	0.0170 (4)	0.0174 (4)	0.0164 (4)	0.0018 (3)	0.0091 (3)	0.0008 (3)
N2	0.0147 (4)	0.0135 (4)	0.0135 (4)	−0.0011 (3)	0.0063 (3)	−0.0006 (3)
N3	0.0234 (5)	0.0244 (5)	0.0266 (5)	0.0047 (4)	0.0154 (4)	0.0035 (4)
C1	0.0202 (5)	0.0171 (5)	0.0187 (5)	0.0027 (4)	0.0119 (4)	0.0012 (4)
C2	0.0152 (5)	0.0150 (5)	0.0248 (6)	0.0012 (4)	0.0104 (4)	0.0006 (4)
C3	0.0143 (4)	0.0197 (5)	0.0196 (5)	0.0000 (4)	0.0043 (4)	−0.0017 (4)
C4	0.0160 (4)	0.0168 (5)	0.0152 (5)	−0.0007 (4)	0.0062 (4)	−0.0025 (4)
C5	0.0141 (4)	0.0111 (4)	0.0153 (5)	−0.0013 (3)	0.0077 (4)	0.0000 (3)
C6	0.0142 (4)	0.0110 (4)	0.0144 (5)	−0.0008 (3)	0.0075 (4)	−0.0004 (3)
C7	0.0150 (4)	0.0148 (4)	0.0135 (5)	−0.0001 (4)	0.0074 (4)	−0.0011 (3)
C8	0.0141 (4)	0.0120 (4)	0.0129 (4)	−0.0006 (3)	0.0059 (4)	−0.0001 (3)
C9	0.0139 (4)	0.0122 (4)	0.0142 (5)	0.0003 (3)	0.0072 (4)	−0.0002 (3)
C10	0.0167 (4)	0.0119 (4)	0.0120 (4)	−0.0006 (3)	0.0073 (4)	−0.0005 (3)
C11	0.0128 (4)	0.0144 (5)	0.0125 (4)	0.0001 (3)	0.0058 (3)	0.0000 (3)
C12	0.0140 (4)	0.0135 (5)	0.0146 (5)	0.0013 (4)	0.0061 (4)	0.0005 (4)
C13	0.0152 (4)	0.0136 (5)	0.0134 (5)	0.0001 (4)	0.0059 (4)	−0.0011 (4)
C14	0.0123 (4)	0.0152 (5)	0.0124 (4)	−0.0005 (3)	0.0051 (4)	0.0014 (3)
C15	0.0151 (4)	0.0130 (5)	0.0167 (5)	0.0022 (4)	0.0083 (4)	0.0010 (4)
C16	0.0158 (4)	0.0136 (5)	0.0135 (5)	−0.0004 (4)	0.0071 (4)	−0.0016 (4)
C17	0.0215 (5)	0.0256 (6)	0.0107 (5)	−0.0002 (4)	0.0051 (4)	0.0000 (4)
C18	0.0183 (5)	0.0152 (5)	0.0143 (5)	0.0003 (4)	0.0078 (4)	0.0011 (4)
C19	0.0188 (5)	0.0158 (5)	0.0172 (5)	0.0028 (4)	0.0055 (4)	−0.0041 (4)
C20	0.0156 (5)	0.0177 (5)	0.0162 (5)	−0.0018 (4)	0.0030 (4)	−0.0029 (4)
C21	0.0273 (6)	0.0188 (5)	0.0225 (6)	0.0059 (4)	0.0122 (5)	−0.0033 (4)

O1—C10	1.3499 (12)	C8—C9	1.4041 (14)
O1—C17	1.4415 (13)	C8—C11	1.4820 (13)
O2—C12	1.3676 (12)	C9—C10	1.4152 (13)
O2—C19	1.4332 (13)	C9—C18	1.4355 (14)
O3—C14	1.3576 (12)	C11—C12	1.4036 (14)
O3—C20	1.4349 (13)	C11—C16	1.4110 (14)
O4—C15	1.3715 (12)	C12—C13	1.4006 (14)
O4—C21	1.4250 (14)	C13—C14	1.3888 (14)
N1—C1	1.3403 (14)	C13—H13A	0.9500
N1—C5	1.3465 (13)	C14—C15	1.4085 (14)
N2—C10	1.3152 (13)	C15—C16	1.3819 (14)
N2—C6	1.3549 (13)	C16—H16A	0.9500
N3—C18	1.1476 (14)	C17—H17A	0.9800
C1—C2	1.3883 (15)	C17—H17B	0.9800
C1—H1A	0.9500	C17—H17C	0.9800
C2—C3	1.3876 (16)	C19—H19A	0.9800
C2—H2A	0.9500	C19—H19B	0.9800
C3—C4	1.3899 (15)	C19—H19C	0.9800
C3—H3A	0.9500	C20—H20A	0.9800
C4—C5	1.3970 (14)	C20—H20B	0.9800
C4—H4A	0.9500	C20—H20C	0.9800
C5—C6	1.4885 (14)	C21—H21A	0.9800
C6—C7	1.3866 (14)	C21—H21B	0.9800
C7—C8	1.4013 (14)	C21—H21C	0.9800
C7—H7A	0.9500
C10—O1—C17	116.48 (8)	O2—C12—C11	117.43 (9)
C12—O2—C19	117.84 (8)	C13—C12—C11	120.54 (9)
C14—O3—C20	116.99 (8)	C14—C13—C12	120.38 (9)
C15—O4—C21	116.88 (8)	C14—C13—H13A	119.8
C1—N1—C5	117.40 (9)	C12—C13—H13A	119.8
C10—N2—C6	117.15 (9)	O3—C14—C13	124.30 (9)
N1—C1—C2	123.76 (10)	O3—C14—C15	115.72 (9)
N1—C1—H1A	118.1	C13—C14—C15	119.98 (9)
C2—C1—H1A	118.1	O4—C15—C16	125.54 (9)
C3—C2—C1	118.37 (10)	O4—C15—C14	115.26 (9)
C3—C2—H2A	120.8	C16—C15—C14	119.20 (9)
C1—C2—H2A	120.8	C15—C16—C11	121.96 (9)
C2—C3—C4	119.00 (10)	C15—C16—H16A	119.0
C2—C3—H3A	120.5	C11—C16—H16A	119.0
C4—C3—H3A	120.5	O1—C17—H17A	109.5
C3—C4—C5	118.62 (10)	O1—C17—H17B	109.5
C3—C4—H4A	120.7	H17A—C17—H17B	109.5
C5—C4—H4A	120.7	O1—C17—H17C	109.5
N1—C5—C4	122.85 (9)	H17A—C17—H17C	109.5
N1—C5—C6	116.40 (9)	H17B—C17—H17C	109.5
C4—C5—C6	120.73 (9)	N3—C18—C9	178.32 (12)
N2—C6—C7	123.03 (9)	O2—C19—H19A	109.5
N2—C6—C5	116.20 (9)	O2—C19—H19B	109.5
C7—C6—C5	120.77 (9)	H19A—C19—H19B	109.5
C6—C7—C8	120.21 (9)	O2—C19—H19C	109.5
C6—C7—H7A	119.9	H19A—C19—H19C	109.5
C8—C7—H7A	119.9	H19B—C19—H19C	109.5
C7—C8—C9	116.76 (9)	O3—C20—H20A	109.5
C7—C8—C11	121.44 (9)	O3—C20—H20B	109.5
C9—C8—C11	121.80 (9)	H20A—C20—H20B	109.5
C8—C9—C10	118.53 (9)	O3—C20—H20C	109.5
C8—C9—C18	123.23 (9)	H20A—C20—H20C	109.5
C10—C9—C18	118.06 (9)	H20B—C20—H20C	109.5
N2—C10—O1	120.08 (9)	O4—C21—H21A	109.5
N2—C10—C9	124.32 (9)	O4—C21—H21B	109.5
O1—C10—C9	115.60 (9)	H21A—C21—H21B	109.5
C12—C11—C16	117.94 (9)	O4—C21—H21C	109.5
C12—C11—C8	122.14 (9)	H21A—C21—H21C	109.5
C16—C11—C8	119.92 (9)	H21B—C21—H21C	109.5
O2—C12—C13	121.99 (9)
C5—N1—C1—C2	0.52 (16)	C8—C9—C10—O1	179.95 (9)
N1—C1—C2—C3	−0.76 (17)	C18—C9—C10—O1	4.76 (14)
C1—C2—C3—C4	0.29 (16)	C7—C8—C11—C12	−42.34 (15)
C2—C3—C4—C5	0.33 (16)	C9—C8—C11—C12	137.61 (11)
C1—N1—C5—C4	0.16 (15)	C7—C8—C11—C16	138.34 (10)
C1—N1—C5—C6	178.65 (9)	C9—C8—C11—C16	−41.70 (14)
C3—C4—C5—N1	−0.58 (16)	C19—O2—C12—C13	−11.45 (15)
C3—C4—C5—C6	−179.01 (10)	C19—O2—C12—C11	171.00 (9)
C10—N2—C6—C7	−0.63 (15)	C16—C11—C12—O2	178.04 (9)
C10—N2—C6—C5	178.74 (9)	C8—C11—C12—O2	−1.29 (15)
N1—C5—C6—N2	−179.26 (9)	C16—C11—C12—C13	0.46 (15)
C4—C5—C6—N2	−0.74 (14)	C8—C11—C12—C13	−178.87 (9)
N1—C5—C6—C7	0.12 (14)	O2—C12—C13—C14	−176.97 (10)
C4—C5—C6—C7	178.65 (10)	C11—C12—C13—C14	0.50 (16)
N2—C6—C7—C8	1.31 (16)	C20—O3—C14—C13	−0.80 (15)
C5—C6—C7—C8	−178.03 (9)	C20—O3—C14—C15	179.26 (9)
C6—C7—C8—C9	−0.94 (15)	C12—C13—C14—O3	179.36 (10)
C6—C7—C8—C11	179.02 (9)	C12—C13—C14—C15	−0.70 (16)
C7—C8—C9—C10	0.02 (14)	C21—O4—C15—C16	8.11 (16)
C11—C8—C9—C10	−179.94 (9)	C21—O4—C15—C14	−171.38 (10)
C7—C8—C9—C18	174.95 (9)	O3—C14—C15—O4	−0.60 (14)
C11—C8—C9—C18	−5.01 (16)	C13—C14—C15—O4	179.45 (9)
C6—N2—C10—O1	−179.62 (9)	O3—C14—C15—C16	179.88 (9)
C6—N2—C10—C9	−0.37 (15)	C13—C14—C15—C16	−0.07 (15)
C17—O1—C10—N2	6.18 (14)	O4—C15—C16—C11	−178.40 (10)
C17—O1—C10—C9	−173.13 (9)	C14—C15—C16—C11	1.06 (16)
C8—C9—C10—N2	0.67 (16)	C12—C11—C16—C15	−1.25 (15)
C18—C9—C10—N2	−174.53 (10)	C8—C11—C16—C15	178.09 (10)

D—H···A	D—H	H···A	D···A	D—H···A
C20—H20C···N3i	0.98	2.59	3.3774 (17)	138
C1—H1A···Cg3ii	0.95	2.89	3.7062 (13)	145

Table 1

Hydrogen-bond geometry (Å, °)

Cg 3 is the centroid of the C11–C16 ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C20—H20C⋯N3i	0.98	2.59	3.3774 (17)	138
C1—H1A⋯Cg3ii	0.95	2.89	3.7062 (13)	145

Symmetry codes: (i) ; (ii) .