Literature DB >> 23284525

5,6-Dimethyl-pyrazine-2,3-dicarbonitrile.

Ghasem Rezanejade Bardajee¹, Alan J Lough, Mitchell A Winnik.

Abstract

The asymmetric unit of the title compound, C(8)H(6)N(4), contains two almost planar independent mol-ecules (r.m.s. deviations = 0.026 and 0.030 Å). The crystal studied was a non-merohedral twin with the components in a 0.513 (2):0.487 (2) ratio.

Entities: Chemical Disease Species

Year: 2012 PMID： 23284525 PMCID： PMC3515305 DOI： 10.1107/S1600536812043474

Source DB: PubMed Journal: Acta Crystallogr Sect E Struct Rep Online ISSN： 1600-5368

Related literature

For applications of pyrazine compounds and their derivatives, see: He et al. (2003 ▶); Yadav et al. (2008 ▶). For the synthesis, see: Bardajee et al. (2012 ▶). For related structures, see: Hökelek et al. (2009 ▶); Donzello et al. (2004 ▶); Cristiano et al. (2007 ▶).

Experimental

Crystal data

C8H6N4 M = 158.17 Monoclinic, a = 24.183 (2) Å b = 9.210 (1) Å c = 18.761 (2) Å β = 130.151 (2)° V = 3193.8 (6) Å3 Z = 16 Mo Kα radiation μ = 0.09 mm−1 T = 150 K 0.28 × 0.22 × 0.18 mm

Data collection

Bruker Kappa APEXII DUO CCD diffractometer Absorption correction: multi-scan (SADABS; Bruker, 2007 ▶) T min = 0.711, T max = 0.746 7543 measured reflections 3650 independent reflections 2927 reflections with I > 2σ(I) R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.110 S = 1.05 3650 reflections 222 parameters H-atom parameters constrained Δρmax = 0.21 e Å−3 Δρmin = −0.21 e Å−3 Data collection: APEX2 (Bruker, 2007 ▶); cell refinement: SAINT (Bruker, 2007 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXTL (Sheldrick, 2008 ▶). Click here for additional data file. Crystal structure: contains datablock(s) global, I. DOI: 10.1107/S1600536812043474/hb6967sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812043474/hb6967Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812043474/hb6967Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C₈H₆N₄	F(000) = 1312
M_r = 158.17	D_x = 1.316 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 3553 reflections
a = 24.183 (2) Å	θ = 2.5–27.5°
b = 9.210 (1) Å	µ = 0.09 mm⁻¹
c = 18.761 (2) Å	T = 150 K
β = 130.151 (2)°	Block, colourless
V = 3193.8 (6) Å³	0.28 × 0.22 × 0.18 mm
Z = 16

Bruker Kappa APEXII DUO CCD diffractometer	3650 independent reflections
Radiation source: fine-focus sealed tube	2927 reflections with I > 2σ(I)
Bruker Triumph monochromator	R_int = 0.034
φ and ω scans	θ_max = 27.5°, θ_min = 2.2°
Absorption correction: multi-scan (SADABS; Bruker, 2007)	h = −31→31
T_min = 0.711, T_max = 0.746	k = −11→11
7543 measured reflections	l = −23→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)] = 0.039	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.110	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.057P)² + 0.5454P] where P = (F_o² + 2F_c²)/3
3650 reflections	(Δ/σ)_max = 0.001
222 parameters	Δρ_max = 0.21 e Å⁻³
0 restraints	Δρ_min = −0.21 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	U_iso*/U_eq
N1A	0.04856 (10)	0.48725 (16)	0.69738 (13)	0.0248 (4)
N2A	0.19891 (9)	0.49247 (15)	0.79770 (12)	0.0243 (4)
N3A	0.02419 (9)	0.11627 (19)	0.68396 (15)	0.0406 (4)
N4A	0.23018 (9)	0.12325 (19)	0.81987 (14)	0.0376 (4)
C1A	0.08817 (10)	0.3648 (2)	0.72638 (13)	0.0236 (4)
C2A	0.16196 (10)	0.3674 (2)	0.77523 (12)	0.0227 (4)
C3A	0.08416 (11)	0.6117 (2)	0.71857 (12)	0.0249 (4)
C4A	0.16036 (11)	0.6147 (2)	0.76943 (14)	0.0245 (4)
C5A	0.05086 (12)	0.2266 (2)	0.70240 (16)	0.0275 (5)
C6A	0.20185 (12)	0.2326 (2)	0.80236 (17)	0.0269 (5)
C7A	0.04121 (14)	0.7493 (2)	0.68703 (18)	0.0338 (6)
H7AA	−0.0082	0.7271	0.6615	0.051*
H7AB	0.0398	0.7954	0.6388	0.051*
H7AC	0.0639	0.8155	0.7402	0.051*
C8A	0.19974 (14)	0.7552 (2)	0.79508 (18)	0.0312 (5)
H8AA	0.2503	0.7364	0.8246	0.047*
H8AB	0.1977	0.8079	0.8387	0.047*
H8AC	0.1771	0.8138	0.7388	0.047*
N1B	0.09889 (10)	0.74478 (15)	0.54586 (13)	0.0259 (4)
N2B	0.14892 (10)	0.73602 (17)	0.44671 (13)	0.0272 (4)
N3B	0.07877 (10)	0.3751 (2)	0.55725 (13)	0.0378 (4)
N4B	0.15302 (10)	0.36510 (18)	0.42592 (13)	0.0367 (4)
C1B	0.10706 (10)	0.6194 (2)	0.51766 (13)	0.0234 (4)
C2B	0.13235 (10)	0.6149 (2)	0.46911 (13)	0.0234 (4)
C3B	0.11532 (10)	0.8655 (2)	0.52460 (13)	0.0258 (4)
C4B	0.14069 (10)	0.8614 (2)	0.47436 (13)	0.0268 (4)
C5B	0.09057 (12)	0.4855 (2)	0.54051 (15)	0.0276 (5)
C6B	0.14345 (12)	0.4770 (3)	0.44367 (16)	0.0277 (5)
C7B	0.10652 (13)	1.0064 (3)	0.55575 (18)	0.0347 (6)
H7BA	0.0831	0.9892	0.5823	0.052*
H7BB	0.0766	1.0721	0.5023	0.052*
H7BC	0.1541	1.0504	0.6031	0.052*
C8B	0.15737 (15)	0.9966 (3)	0.44719 (19)	0.0385 (6)
H8BA	0.1780	0.9705	0.4180	0.058*
H8BB	0.1922	1.0555	0.5029	0.058*
H8BC	0.1128	1.0523	0.4029	0.058*

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
N1A	0.0244 (9)	0.0262 (8)	0.0213 (8)	−0.0012 (6)	0.0135 (8)	−0.0013 (6)
N2A	0.0252 (9)	0.0241 (9)	0.0209 (8)	−0.0027 (6)	0.0136 (8)	−0.0024 (6)
N3A	0.0297 (9)	0.0301 (8)	0.0433 (9)	−0.0022 (7)	0.0150 (8)	0.0007 (8)
N4A	0.0269 (8)	0.0308 (8)	0.0386 (9)	0.0008 (7)	0.0135 (8)	−0.0011 (7)
C1A	0.0265 (9)	0.0230 (10)	0.0198 (8)	−0.0027 (8)	0.0142 (8)	−0.0011 (7)
C2A	0.0217 (9)	0.0237 (9)	0.0183 (8)	−0.0001 (7)	0.0109 (7)	−0.0010 (7)
C3A	0.0306 (10)	0.0235 (9)	0.0215 (9)	0.0014 (8)	0.0172 (8)	−0.0013 (7)
C4A	0.0289 (10)	0.0238 (9)	0.0232 (9)	−0.0033 (8)	0.0178 (8)	−0.0027 (7)
C5A	0.0205 (10)	0.0266 (11)	0.0260 (9)	−0.0008 (8)	0.0107 (8)	0.0018 (8)
C6A	0.0220 (10)	0.0256 (11)	0.0265 (10)	−0.0046 (8)	0.0127 (9)	−0.0022 (8)
C7A	0.0375 (13)	0.0221 (12)	0.0402 (13)	0.0047 (8)	0.0242 (12)	0.0000 (8)
C8A	0.0340 (12)	0.0226 (12)	0.0319 (11)	−0.0049 (8)	0.0190 (10)	−0.0034 (7)
N1B	0.0249 (9)	0.0257 (10)	0.0246 (10)	0.0005 (6)	0.0148 (8)	−0.0026 (6)
N2B	0.0265 (10)	0.0275 (9)	0.0250 (9)	−0.0025 (6)	0.0155 (9)	0.0003 (6)
N3B	0.0564 (12)	0.0305 (8)	0.0387 (9)	−0.0069 (8)	0.0362 (9)	−0.0043 (7)
N4B	0.0504 (11)	0.0293 (8)	0.0418 (9)	0.0023 (8)	0.0349 (9)	0.0005 (7)
C1B	0.0215 (9)	0.0252 (10)	0.0201 (8)	−0.0014 (7)	0.0119 (8)	−0.0008 (7)
C2B	0.0213 (9)	0.0246 (10)	0.0198 (8)	−0.0013 (7)	0.0113 (8)	−0.0008 (7)
C3B	0.0187 (9)	0.0250 (10)	0.0226 (9)	−0.0008 (7)	0.0083 (8)	−0.0009 (7)
C4B	0.0216 (9)	0.0274 (10)	0.0231 (9)	−0.0002 (8)	0.0106 (8)	0.0010 (8)
C5B	0.0333 (11)	0.0283 (12)	0.0242 (10)	−0.0009 (8)	0.0198 (9)	−0.0025 (8)
C6B	0.0294 (11)	0.0323 (12)	0.0247 (10)	−0.0021 (9)	0.0190 (9)	0.0015 (8)
C7B	0.0325 (12)	0.0301 (12)	0.0384 (12)	0.0015 (9)	0.0215 (11)	−0.0023 (9)
C8B	0.0439 (14)	0.0301 (13)	0.0432 (14)	−0.0044 (9)	0.0288 (12)	0.0023 (9)

N1A—C3A	1.331 (2)	N1B—C3B	1.326 (3)
N1A—C1A	1.346 (3)	N1B—C1B	1.337 (3)
N2A—C4A	1.334 (2)	N2B—C4B	1.333 (3)
N2A—C2A	1.348 (2)	N2B—C2B	1.341 (3)
N3A—C5A	1.132 (3)	N3B—C5B	1.153 (3)
N4A—C6A	1.141 (3)	N4B—C6B	1.151 (3)
C1A—C2A	1.384 (3)	C1B—C2B	1.387 (3)
C1A—C5A	1.454 (3)	C1B—C5B	1.444 (3)
C2A—C6A	1.448 (3)	C2B—C6B	1.442 (3)
C3A—C4A	1.428 (3)	C3B—C4B	1.418 (3)
C3A—C7A	1.497 (3)	C3B—C7B	1.494 (3)
C4A—C8A	1.491 (3)	C4B—C8B	1.496 (3)
C7A—H7AA	0.9800	C7B—H7BA	0.9800
C7A—H7AB	0.9800	C7B—H7BB	0.9800
C7A—H7AC	0.9800	C7B—H7BC	0.9800
C8A—H8AA	0.9800	C8B—H8BA	0.9800
C8A—H8AB	0.9800	C8B—H8BB	0.9800
C8A—H8AC	0.9800	C8B—H8BC	0.9800

C3A—N1A—C1A	116.49 (17)	C3B—N1B—C1B	117.12 (19)
C4A—N2A—C2A	116.36 (17)	C4B—N2B—C2B	116.69 (19)
N1A—C1A—C2A	122.05 (17)	N1B—C1B—C2B	121.73 (17)
N1A—C1A—C5A	118.06 (17)	N1B—C1B—C5B	118.72 (18)
C2A—C1A—C5A	119.86 (17)	C2B—C1B—C5B	119.53 (17)
N2A—C2A—C1A	122.25 (17)	N2B—C2B—C1B	121.89 (17)
N2A—C2A—C6A	117.74 (17)	N2B—C2B—C6B	118.18 (18)
C1A—C2A—C6A	120.00 (17)	C1B—C2B—C6B	119.91 (17)
N1A—C3A—C4A	121.55 (17)	N1B—C3B—C4B	121.32 (17)
N1A—C3A—C7A	117.42 (18)	N1B—C3B—C7B	117.71 (19)
C4A—C3A—C7A	121.03 (18)	C4B—C3B—C7B	120.97 (19)
N2A—C4A—C3A	121.30 (16)	N2B—C4B—C3B	121.25 (18)
N2A—C4A—C8A	117.84 (18)	N2B—C4B—C8B	116.6 (2)
C3A—C4A—C8A	120.83 (17)	C3B—C4B—C8B	122.12 (18)
N3A—C5A—C1A	176.9 (2)	N3B—C5B—C1B	176.8 (2)
N4A—C6A—C2A	176.6 (3)	N4B—C6B—C2B	177.9 (2)
C3A—C7A—H7AA	109.5	C3B—C7B—H7BA	109.5
C3A—C7A—H7AB	109.5	C3B—C7B—H7BB	109.5
H7AA—C7A—H7AB	109.5	H7BA—C7B—H7BB	109.5
C3A—C7A—H7AC	109.5	C3B—C7B—H7BC	109.5
H7AA—C7A—H7AC	109.5	H7BA—C7B—H7BC	109.5
H7AB—C7A—H7AC	109.5	H7BB—C7B—H7BC	109.5
C4A—C8A—H8AA	109.5	C4B—C8B—H8BA	109.5
C4A—C8A—H8AB	109.5	C4B—C8B—H8BB	109.5
H8AA—C8A—H8AB	109.5	H8BA—C8B—H8BB	109.5
C4A—C8A—H8AC	109.5	C4B—C8B—H8BC	109.5
H8AA—C8A—H8AC	109.5	H8BA—C8B—H8BC	109.5
H8AB—C8A—H8AC	109.5	H8BB—C8B—H8BC	109.5

C3A—N1A—C1A—C2A	−0.4 (3)	C3B—N1B—C1B—C2B	0.7 (3)
C3A—N1A—C1A—C5A	−178.40 (18)	C3B—N1B—C1B—C5B	179.24 (18)
C4A—N2A—C2A—C1A	−0.7 (3)	C4B—N2B—C2B—C1B	0.7 (3)
C4A—N2A—C2A—C6A	178.1 (2)	C4B—N2B—C2B—C6B	−177.5 (2)
N1A—C1A—C2A—N2A	0.7 (3)	N1B—C1B—C2B—N2B	−1.0 (3)
C5A—C1A—C2A—N2A	178.75 (17)	C5B—C1B—C2B—N2B	−179.54 (17)
N1A—C1A—C2A—C6A	−178.02 (17)	N1B—C1B—C2B—C6B	177.20 (19)
C5A—C1A—C2A—C6A	0.0 (3)	C5B—C1B—C2B—C6B	−1.3 (3)
C1A—N1A—C3A—C4A	0.0 (3)	C1B—N1B—C3B—C4B	−0.2 (3)
C1A—N1A—C3A—C7A	−179.98 (19)	C1B—N1B—C3B—C7B	−179.94 (19)
C2A—N2A—C4A—C3A	0.3 (3)	C2B—N2B—C4B—C3B	−0.3 (3)
C2A—N2A—C4A—C8A	178.52 (19)	C2B—N2B—C4B—C8B	−178.47 (19)
N1A—C3A—C4A—N2A	0.0 (3)	N1B—C3B—C4B—N2B	0.0 (3)
C7A—C3A—C4A—N2A	−179.99 (18)	C7B—C3B—C4B—N2B	179.73 (19)
N1A—C3A—C4A—C8A	−178.13 (18)	N1B—C3B—C4B—C8B	178.10 (19)
C7A—C3A—C4A—C8A	1.8 (3)	C7B—C3B—C4B—C8B	−2.2 (3)

5 in total

1. A short history of SHELX.

Authors: George M Sheldrick
Journal: Acta Crystallogr A Date: 2007-12-21 Impact factor: 2.290

2. Potent quinoxaline-based inhibitors of PDGF receptor tyrosine kinase activity. Part 2: the synthesis and biological activities of RPR127963 an orally bioavailable inhibitor.

Authors: Wei He; Michael R Myers; Barbara Hanney; Alfred P Spada; Glenda Bilder; Helen Galzcinski; Dilip Amin; Saul Needle; Ken Page; Zaid Jayyosi; Mark H Perrone
Journal: Bioorg Med Chem Lett Date: 2003-09-15 Impact factor: 2.823

3. Tetra-2,3-pyrazinoporphyrazines with externally appended pyridine rings. 1. Tetrakis-2,3-[5,6-di(2-pyridyl)pyrazino]porphyrazine: a new macrocycle with remarkable electron-deficient properties.

Authors: Maria Pia Donzello; Zhongping Ou; Fabrizio Monacelli; Giampaolo Ricciardi; Corrado Rizzoli; Claudio Ercolani; Karl M Kadish
Journal: Inorg Chem Date: 2004-12-27 Impact factor: 5.165

4. 5,6-Diphenyl-pyrazine-2,3-dicarbonitrile.

Authors: Tuncer Hökelek; Ergin Yalçın; Zeynel Seferoğlu; Ertan Sahin
Journal: Acta Crystallogr Sect E Struct Rep Online Date: 2009-08-22

5. Structure validation in chemical crystallography.

Authors: Anthony L Spek
Journal: Acta Crystallogr D Biol Crystallogr Date: 2009-01-20

5 in total