Dimethyl 6,6'-dicyano-2,2'-bipyridine-3,3'-dicarboxyl-ate.

In the title compound, C(16)H(10)N(4)O(4), the two pyridine rings are twisted by 44.41 (2)° and the ester groups form dihedral angles of 48.77 (4) and 45.75 (2)° with the corresponding pyridine rings. The crystal structure is stabilized by inter-molecular C-H⋯O hydrogen bonds and π-π stacking inter-actions between the pyridine rings [centroid-to-centroid distance 3.797 (2) Å].

Related literature

For the synthetic procedures relevant to preparation of the title compound, see: Tichy et al. (1995 ▶); Glaup et al. (2005 ▶); Heirtzler (1999 ▶)

Experimental

Crystal data

C16H10N4O4

M = 322.28

Triclinic,

a = 8.201 (3) Å

b = 10.302 (6) Å

c = 10.768 (3) Å

α = 109.148 (4)°

β = 106.091 (3)°

γ = 100.404 (5)°

V = 787.9 (6) Å3

Z = 2

Mo Kα radiation

μ = 0.10 mm−1

T = 296 K

0.49 × 0.45 × 0.41 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.952, T max = 0.960

5613 measured reflections

2845 independent reflections

2391 reflections with I > 2σ(I)

R int = 0.014

Refinement

R[F 2 > 2σ(F 2)] = 0.034

wR(F 2) = 0.094

S = 1.05

2845 reflections

218 parameters

H-atom parameters constrained

Δρmax = 0.15 e Å−3

Δρmin = −0.12 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXS97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: SHELXTL and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012446/gk2200sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012446/gk2200Isup2.hkl

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

C16H10N4O4	Z = 2
Mr = 322.28	F(000) = 332
Triclinic, P1	Dx = 1.358 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.201 (3) Å	Cell parameters from 2697 reflections
b = 10.302 (6) Å	θ = 2.4–25.5°
c = 10.768 (3) Å	µ = 0.10 mm−1
α = 109.148 (4)°	T = 296 K
β = 106.091 (3)°	Block, yellow
γ = 100.404 (5)°	0.49 × 0.45 × 0.41 mm
V = 787.9 (6) Å3

Bruker APEXII CCD diffractometer	2845 independent reflections
Radiation source: fine-focus sealed tube	2391 reflections with I > 2σ(I)
graphite	Rint = 0.014
Detector resolution: 0 pixels mm-1	θmax = 25.5°, θmin = 2.4°
phi and ω scans	h = −9→9
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	k = −12→12
Tmin = 0.952, Tmax = 0.960	l = −13→12
5613 measured reflections

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.034	H-atom parameters constrained
wR(F2) = 0.094	w = 1/[σ2(Fo2) + (0.0434P)2 + 0.140P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max < 0.001
2845 reflections	Δρmax = 0.15 e Å−3
218 parameters	Δρmin = −0.11 e Å−3
0 restraints	Extinction correction: SHELXL, Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.044 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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	0.24082 (14)	0.31796 (12)	0.50125 (12)	0.0430 (3)
N2	0.10699 (15)	−0.04177 (12)	0.29318 (12)	0.0441 (3)
N3	0.2207 (3)	0.64855 (17)	0.68504 (19)	0.0880 (5)
N4	−0.1464 (3)	−0.37966 (17)	0.06250 (18)	0.0918 (6)
O1	0.21123 (14)	0.07920 (12)	0.04429 (10)	0.0584 (3)
O3	0.39330 (14)	0.18868 (11)	0.78250 (10)	0.0537 (3)
O4	0.55513 (13)	0.24358 (11)	0.65966 (11)	0.0589 (3)
O2	0.41072 (15)	0.03548 (12)	0.20273 (11)	0.0611 (3)
C2	0.28278 (17)	0.22264 (15)	0.28064 (14)	0.0425 (3)
C1	0.25460 (16)	0.20947 (14)	0.39931 (14)	0.0392 (3)
C12	0.30974 (18)	0.10132 (15)	0.17406 (14)	0.0448 (3)
C3	0.2918 (2)	0.35319 (16)	0.26803 (16)	0.0520 (4)
H3A	0.3070	0.3642	0.1892	0.062*
C4	0.2783 (2)	0.46654 (16)	0.37267 (17)	0.0534 (4)
H4A	0.2850	0.5553	0.3668	0.064*
C5	0.25452 (18)	0.44348 (14)	0.48638 (16)	0.0461 (3)
C11	0.2373 (2)	0.55804 (17)	0.59939 (19)	0.0585 (4)
C15	0.2181 (3)	−0.0415 (2)	−0.06874 (17)	0.0693 (5)
H15A	0.1425	−0.0479	−0.1578	0.104*
H15B	0.1782	−0.1288	−0.0572	0.104*
H15C	0.3381	−0.0277	−0.0661	0.104*
C9	0.10581 (18)	−0.19269 (14)	0.42201 (15)	0.0448 (3)
H9A	0.0618	−0.2823	0.4223	0.054*
C7	0.28339 (16)	0.05361 (13)	0.54006 (13)	0.0379 (3)
C6	0.21790 (16)	0.06783 (13)	0.41195 (14)	0.0382 (3)
C8	0.22261 (18)	−0.07911 (14)	0.54392 (15)	0.0432 (3)
H8A	0.2603	−0.0914	0.6280	0.052*
C10	0.05610 (17)	−0.16976 (14)	0.29983 (14)	0.0436 (3)
C14	0.42572 (18)	0.17362 (14)	0.66546 (14)	0.0416 (3)
C13	−0.0581 (2)	−0.28668 (17)	0.16696 (18)	0.0595 (4)
C16	0.5312 (3)	0.2948 (2)	0.91195 (18)	0.0781 (6)
H16D	0.4957	0.2978	0.9904	0.117*
H16A	0.5497	0.3878	0.9077	0.117*
H16B	0.6398	0.2692	0.9235	0.117*

	U11	U22	U33	U12	U13	U23
N1	0.0426 (6)	0.0382 (6)	0.0467 (7)	0.0097 (5)	0.0153 (5)	0.0172 (5)
N2	0.0445 (6)	0.0400 (6)	0.0427 (7)	0.0101 (5)	0.0113 (5)	0.0153 (5)
N3	0.1169 (15)	0.0572 (10)	0.0928 (13)	0.0325 (10)	0.0510 (11)	0.0193 (9)
N4	0.0980 (13)	0.0583 (10)	0.0702 (11)	0.0005 (9)	0.0005 (10)	0.0035 (9)
O1	0.0661 (7)	0.0712 (7)	0.0413 (6)	0.0318 (6)	0.0166 (5)	0.0232 (5)
O3	0.0612 (6)	0.0478 (6)	0.0391 (5)	0.0067 (5)	0.0151 (5)	0.0092 (5)
O4	0.0460 (6)	0.0583 (7)	0.0626 (7)	0.0006 (5)	0.0143 (5)	0.0246 (6)
O2	0.0594 (7)	0.0714 (7)	0.0530 (6)	0.0332 (6)	0.0153 (5)	0.0225 (6)
C2	0.0385 (7)	0.0450 (8)	0.0438 (8)	0.0108 (6)	0.0120 (6)	0.0209 (6)
C1	0.0361 (7)	0.0385 (7)	0.0406 (7)	0.0093 (5)	0.0106 (5)	0.0167 (6)
C12	0.0417 (7)	0.0506 (8)	0.0437 (8)	0.0114 (6)	0.0155 (6)	0.0220 (7)
C3	0.0543 (9)	0.0559 (9)	0.0567 (9)	0.0159 (7)	0.0229 (7)	0.0335 (8)
C4	0.0556 (9)	0.0434 (8)	0.0701 (10)	0.0160 (7)	0.0239 (8)	0.0317 (8)
C5	0.0422 (7)	0.0380 (7)	0.0571 (9)	0.0109 (6)	0.0168 (6)	0.0191 (7)
C11	0.0652 (10)	0.0415 (9)	0.0706 (11)	0.0165 (7)	0.0269 (8)	0.0225 (8)
C15	0.0746 (11)	0.0858 (13)	0.0416 (9)	0.0346 (10)	0.0174 (8)	0.0161 (9)
C9	0.0437 (7)	0.0360 (7)	0.0567 (9)	0.0096 (6)	0.0208 (6)	0.0200 (7)
C7	0.0376 (7)	0.0376 (7)	0.0402 (7)	0.0117 (5)	0.0162 (6)	0.0158 (6)
C6	0.0380 (7)	0.0369 (7)	0.0406 (7)	0.0111 (5)	0.0149 (6)	0.0159 (6)
C8	0.0467 (7)	0.0426 (8)	0.0448 (8)	0.0132 (6)	0.0183 (6)	0.0216 (6)
C10	0.0396 (7)	0.0370 (7)	0.0463 (8)	0.0083 (6)	0.0119 (6)	0.0118 (6)
C14	0.0433 (7)	0.0370 (7)	0.0442 (8)	0.0128 (6)	0.0135 (6)	0.0175 (6)
C13	0.0613 (10)	0.0434 (9)	0.0568 (10)	0.0070 (7)	0.0098 (8)	0.0136 (8)
C16	0.0843 (13)	0.0666 (11)	0.0445 (10)	0.0064 (10)	0.0046 (9)	−0.0007 (9)

N1—C1	1.3328 (17)	C4—C5	1.378 (2)
N1—C5	1.3430 (18)	C4—H4A	0.9300
N2—C6	1.3322 (17)	C5—C11	1.451 (2)
N2—C10	1.3406 (18)	C15—H15A	0.9600
N3—C11	1.136 (2)	C15—H15B	0.9600
N4—C13	1.139 (2)	C15—H15C	0.9600
O1—C12	1.3252 (17)	C9—C10	1.376 (2)
O1—C15	1.4495 (19)	C9—C8	1.3786 (19)
O3—C14	1.3249 (17)	C9—H9A	0.9300
O3—C16	1.4483 (19)	C7—C8	1.3864 (19)
O4—C14	1.1999 (16)	C7—C6	1.4011 (18)
O2—C12	1.1997 (17)	C7—C14	1.4913 (19)
C2—C3	1.386 (2)	C8—H8A	0.9300
C2—C1	1.4038 (19)	C10—C13	1.447 (2)
C2—C12	1.492 (2)	C16—H16D	0.9600
C1—C6	1.4942 (19)	C16—H16A	0.9600
C3—C4	1.378 (2)	C16—H16B	0.9600
C3—H3A	0.9300
C1—N1—C5	117.06 (12)	H15A—C15—H15C	109.5
C6—N2—C10	117.28 (12)	H15B—C15—H15C	109.5
C12—O1—C15	116.20 (12)	C10—C9—C8	118.15 (12)
C14—O3—C16	115.67 (13)	C10—C9—H9A	120.9
C3—C2—C1	118.21 (13)	C8—C9—H9A	120.9
C3—C2—C12	120.91 (12)	C8—C7—C6	118.08 (12)
C1—C2—C12	120.83 (12)	C8—C7—C14	120.67 (12)
N1—C1—C2	122.74 (12)	C6—C7—C14	121.05 (11)
N1—C1—C6	115.11 (11)	N2—C6—C7	122.92 (12)
C2—C1—C6	121.83 (12)	N2—C6—C1	114.08 (11)
O2—C12—O1	124.85 (14)	C7—C6—C1	122.83 (12)
O2—C12—C2	124.19 (13)	C9—C8—C7	119.38 (13)
O1—C12—C2	110.93 (12)	C9—C8—H8A	120.3
C4—C3—C2	119.75 (13)	C7—C8—H8A	120.3
C4—C3—H3A	120.1	N2—C10—C9	124.06 (12)
C2—C3—H3A	120.1	N2—C10—C13	115.18 (13)
C3—C4—C5	117.53 (13)	C9—C10—C13	120.76 (13)
C3—C4—H4A	121.2	O4—C14—O3	125.10 (13)
C5—C4—H4A	121.2	O4—C14—C7	123.42 (13)
N1—C5—C4	124.68 (13)	O3—C14—C7	111.43 (11)
N1—C5—C11	115.08 (13)	N4—C13—C10	179.1 (2)
C4—C5—C11	120.23 (13)	O3—C16—H16D	109.5
N3—C11—C5	178.05 (19)	O3—C16—H16A	109.5
O1—C15—H15A	109.5	H16D—C16—H16A	109.5
O1—C15—H15B	109.5	O3—C16—H16B	109.5
H15A—C15—H15B	109.5	H16D—C16—H16B	109.5
O1—C15—H15C	109.5	H16A—C16—H16B	109.5
C5—N1—C1—C2	0.20 (19)	C8—C7—C6—N2	−3.22 (19)
C5—N1—C1—C6	−173.30 (11)	C14—C7—C6—N2	171.65 (12)
C3—C2—C1—N1	−1.7 (2)	C8—C7—C6—C1	171.66 (11)
C12—C2—C1—N1	175.79 (12)	C14—C7—C6—C1	−13.47 (18)
C3—C2—C1—C6	171.35 (12)	N1—C1—C6—N2	132.04 (13)
C12—C2—C1—C6	−11.14 (19)	C2—C1—C6—N2	−41.53 (17)
C15—O1—C12—O2	5.1 (2)	N1—C1—C6—C7	−43.25 (17)
C15—O1—C12—C2	−176.63 (12)	C2—C1—C6—C7	143.18 (13)
C3—C2—C12—O2	129.19 (16)	C10—C9—C8—C7	0.99 (19)
C1—C2—C12—O2	−48.3 (2)	C6—C7—C8—C9	2.17 (19)
C3—C2—C12—O1	−49.07 (17)	C14—C7—C8—C9	−172.72 (12)
C1—C2—C12—O1	133.48 (13)	C6—N2—C10—C9	2.6 (2)
C1—C2—C3—C4	1.8 (2)	C6—N2—C10—C13	−177.41 (12)
C12—C2—C3—C4	−175.66 (13)	C8—C9—C10—N2	−3.6 (2)
C2—C3—C4—C5	−0.5 (2)	C8—C9—C10—C13	176.48 (13)
C1—N1—C5—C4	1.3 (2)	C16—O3—C14—O4	−2.7 (2)
C1—N1—C5—C11	179.56 (13)	C16—O3—C14—C7	175.13 (13)
C3—C4—C5—N1	−1.1 (2)	C8—C7—C14—O4	130.87 (15)
C3—C4—C5—C11	−179.31 (14)	C6—C7—C14—O4	−43.86 (19)
C10—N2—C6—C7	0.86 (19)	C8—C7—C14—O3	−46.97 (16)
C10—N2—C6—C1	−174.43 (11)	C6—C7—C14—O3	138.30 (12)

D—H···A	D—H	H···A	D···A	D—H···A
C4—H4A···O4i	0.93	2.39	3.222 (3)	149

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C4—H4A⋯O4i	0.93	2.39	3.222 (3)	149

Symmetry code: (i) .