Dimethyl 6,6′-dicyano-2,2′-bipyridine-3,3′-dicarboxyl­ate

He, X.; Qu, G.-R.; Deng, D.; Ji, B.

doi:10.1107/S1600536809012446

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o985

doi:10.1107/S1600536809012446

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Dimethyl 6,6′-dicyano-2,2′-bipyridine-3,3′-dicarboxylate

Xiao He,^a,^b Gui-Rong Qu,^a Dongsheng Deng ^b and Baoming Ji ^b ^*

^aCollege of Chemistry and Environmental Science, Henan Normal University, Xinxiang 453007, People's Republic of China, and ^bCollege of Chemistry and Chemical Engineering, Luoyang Normal University, Luoyang 471022, People's Republic of China
^*Correspondence e-mail: lyhxxjbm@126.com

(Received 17 March 2009; accepted 2 April 2009; online 8 April 2009)

In the title compound, C₁₆H₁₀N₄O₄, 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 intermolecular C—H⋯O hydrogen bonds and π–π stacking interactions 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_r = 322.28
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.034
wR(F²) = 0.094
S = 1.05
2845 reflections
218 parameters
H-atom parameters constrained
Δρ_max = 0.15 e Å⁻³
Δρ_min = −0.12 e Å⁻³

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) -x+1, -y+1, -z+1.

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 ).

Supporting information

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

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

checkCIF report

Comment top

Binicotinic acid and its derivatives have been proved to be a kind of multifunctional and flexible ligand in the construction of complexes possessing novel and interesting topological structures. Our interest in these compounds has led us to prepare the title compound. First, we synthesized dimethyl 2,2'-bipyridine-3,3'-dicarboxylate 1,1'-dioxide according to the reported method (Tichy et al. 1995). Second, the incorporation of cyano group onto 6 and 6' positions of the above compound could be readily performed when adopting the literature methods (Glaup et al. 2005; Heirtzler 1999). In this contribution, we report the synthesis and crystal structure of the title compound.

The asymmetric unit of the title compound contains one molecule (Fig. 1.). In the crystal structure, the most striking feature of the title compound is the interesting arrangement of the title molecules, which are linked into centrosymmetric dimers by formation of intermolecular C—H···O hydrogen bonds, in which C4—H4A is a donor and O4 is an acceptor (Table 1, Fig. 2). Short π···π contacts between two pyridine rings with centroid-centroid distance of 3.797 (2) Å are observed in the structure.

Related literature top

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

Experimental top

To an ice-cooled solution of dimethyl 2,2'-bipyridine-3,3'-dicarboxylate 1,1'-dioxide (1.22 g, 4 mmol) and trimethylsilyl cyanide (5.2 ml, 40 mmol) in ca 40 ml dry CH₂Cl₂ under N₂ was carefully added benzoyl chloride (1.9 ml, 17 mmol). After stirring overnight at room temperature, 10% aq Na₂CO₃ was carefully added to the chilled reaction mixture and it was concentrated at 200 mbar to complete crude product precipitation. This was collected by filtration, washed with water and dried. Purification by silica gel chromatography using 100 ~200 mesh ZCX II eluted by hexane-ethyl acetate (3:1, v/v) gave the yellow solid. The crystalline compound was obtained by slow evaporation of CH₂Cl₂ solution containing the title compound.

Computing details top

Data collection: APEX2 (Bruker, 2004); cell refinement: SAINT (Bruker, 2004); data reduction: SAINT (Bruker, 2004; 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

	Fig. 1. View of the title molecule with the atom numbering scheme and 30% probability displacement ellipsoids for non-hydrogen atoms. Hydrogen atoms are omitted for clarity.
	Fig. 2. View of the centrosymmetric dimer; C—H···O hydrogen bonds are indicated with broken lines.

(I) top

Crystal data top

C₁₆H₁₀N₄O₄	Z = 2
M_r = 322.28	F(000) = 332
Triclinic, P1	D_x = 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

Data collection top

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

Refinement top

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(F_o²) + (0.0434P)² + 0.140P] where P = (F_o² + 2F_c²)/3
S = 1.05	(Δ/σ)_max < 0.001
2845 reflections	Δρ_max = 0.15 e Å⁻³
218 parameters	Δρ_min = −0.12 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)

Crystal data top

C₁₆H₁₀N₄O₄	γ = 100.404 (5)°
M_r = 322.28	V = 787.9 (6) Å³
Triclinic, P1	Z = 2
a = 8.201 (3) Å	Mo Kα radiation
b = 10.302 (6) Å	µ = 0.10 mm⁻¹
c = 10.768 (3) Å	T = 296 K
α = 109.148 (4)°	0.49 × 0.45 × 0.41 mm
β = 106.091 (3)°

Data collection top

Bruker APEXII CCD diffractometer	2845 independent reflections
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	2391 reflections with I > 2σ(I)
T_min = 0.952, T_max = 0.960	R_int = 0.014
5613 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.034	0 restraints
wR(F²) = 0.094	H-atom parameters constrained
S = 1.05	Δρ_max = 0.15 e Å⁻³
2845 reflections	Δρ_min = −0.12 e Å⁻³
218 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₀N₄O₄
M_r	322.28
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.201 (3), 10.302 (6), 10.768 (3)
α, β, γ (°)	109.148 (4), 106.091 (3), 100.404 (5)
V (Å³)	787.9 (6)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.49 × 0.45 × 0.41

Data collection
Diffractometer	Bruker APEXII CCD diffractometer
Absorption correction	Multi-scan (SADABS; Sheldrick, 1996)
T_min, T_max	0.952, 0.960
No. of measured, independent and observed [I > 2σ(I)] reflections	5613, 2845, 2391
R_int	0.014
(sin θ/λ)_max (Å⁻¹)	0.606

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.034, 0.094, 1.05
No. of reflections	2845
No. of parameters	218
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.15, −0.12

Computer programs: APEX2 (Bruker, 2004), SAINT (Bruker, 2004), SAINT (Bruker, 2004, SHELXS97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008) and DIAMOND (Brandenburg, 2006), SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1.

Acknowledgements

We are grateful to the National Natural Science Foundation of China (grant No. 20872057) and the Natural Science Foundation of Henan Province (No. 082300420040) for financial support.

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