Literature DB >> 21589066

1,2,4,5-Tetra-fluoro-3,6-diiodo-benzene-2,3-bis-(pyridin-2-yl)pyrazine (1/1).

Hadi D Arman, Trupta Kaulgud, Edward R T Tiekink.   

Abstract

The components of the title 1:1 co-crystal, C(14)H(10)N(4)·C(6)F(4)I(2), are connected via an n class="Chemical">N⋯I [2.959 (4) Å] halogen bond, in which the N atom is part of the relatively electron-rich pyrazine ring. The C(6)F(4)I(2) mol-ecule is almost planar [r.m.s. deviation = 0.038 Å] but there are significant twists in the pyrazine derivative, as seen in the dihedral angles [31.3 (2) and 54.6 (2)°] formed between the pendant pyridyl rings and the central pyrazine ring. The bimolecular aggregates are sustained in the crystal by C-H⋯F and π-π inter-actions [ring centroid(pyrid-yl)-ring centroid(benzene) = 3.678 (3) Å].

Entities:  

Year:  2010        PMID： 21589066      PMCID： PMC3009248          DOI： 10.1107/S1600536810041668

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


Related literature

For related studies on co-crystal formation, see: Broker & Tiekink (2007 ▶); Broker et al. (2008 ▶); Arman et al. (2010 ▶). For background to halogen bonding, see: n class="Chemical">Metrangolo et al. (2008 ▶); Pennington et al. (2008 ▶).

Experimental

Crystal data

C14H10N4·C6F4I2 M = 636.04 Triclinic, a = 6.3997 (15) Å b = 10.737 (2) Å c = 15.092 (4) Å α = 74.237 (10)° β = 85.877 (11)° γ = 80.283 (12)° V = 983.3 (4) Å3 Z = 2 Mo Kα radiation μ = 3.25 mm−1 T = 98 K 0.40 × 0.13 × 0.07 mm

Data collection

Rigaku AFC12/SATURN724 diffractometer Absorption correction: multi-scan (ABSCOR; Higashi, 1995 ▶) T min = 0.504, T max = 1.000 5074 measured reflections 3775 independent reflections 3550 reflections with I > 2σ(I) R int = 0.025

Refinement

R[F 2 > 2σ(F 2)] = 0.039 wR(F 2) = 0.109 S = 1.09 3775 reflections 271 parameters H-atom parameters constrained Δρmax = 1.32 e Å−3 Δρmin = −1.20 e Å−3 Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005 ▶); cell refinement: CrystalClear; data reduction: CrystalClear; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and DIAMOND (Brandenburg, 2006 ▶); software used to prepare material for publication: publCIF (Westrip, 2010 ▶). Crystal structure: contains datablocks general, I. DOI: 10.1107/S1600536810041668/hb5683sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536810041668/hb5683Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C14H10N4·C6F4I2Z = 2
Mr = 636.04F(000) = 600
Triclinic, P1Dx = 2.148 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 6.3997 (15) ÅCell parameters from 2870 reflections
b = 10.737 (2) Åθ = 2.8–40.2°
c = 15.092 (4) ŵ = 3.25 mm−1
α = 74.237 (10)°T = 98 K
β = 85.877 (11)°Prism, colourless
γ = 80.283 (12)°0.40 × 0.13 × 0.07 mm
V = 983.3 (4) Å3
Rigaku AFC12K/SATURN724 diffractometer3775 independent reflections
Radiation source: fine-focus sealed tube3550 reflections with I > 2σ(I)
graphiteRint = 0.025
ω scansθmax = 26.0°, θmin = 2.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)h = −7→7
Tmin = 0.504, Tmax = 1.000k = −13→13
5074 measured reflectionsl = −18→18
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.039Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.109H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.0647P)2 + 2.2885P] where P = (Fo2 + 2Fc2)/3
3775 reflections(Δ/σ)max = 0.001
271 parametersΔρmax = 1.32 e Å−3
0 restraintsΔρmin = −1.20 e Å−3
Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'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 > 2σ(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.
xyzUiso*/Ueq
I10.02819 (5)0.31600 (3)0.57773 (2)0.02562 (13)
I20.78603 (5)−0.24672 (3)0.69360 (2)0.02055 (12)
F10.0119 (4)0.0318 (3)0.7123 (2)0.0253 (6)
F20.2992 (5)−0.1842 (3)0.7543 (2)0.0243 (6)
F30.7961 (5)0.0349 (3)0.5483 (2)0.0237 (6)
F40.5096 (5)0.2523 (3)0.5082 (2)0.0235 (6)
C10.2526 (8)0.1487 (5)0.6091 (3)0.0187 (10)
C20.2048 (7)0.0342 (5)0.6718 (3)0.0183 (9)
C30.3548 (8)−0.0770 (5)0.6931 (3)0.0185 (9)
C40.5573 (8)−0.0806 (5)0.6541 (3)0.0184 (9)
C50.6036 (7)0.0330 (4)0.5907 (3)0.0168 (9)
C60.4545 (8)0.1452 (5)0.5692 (3)0.0168 (9)
N10.4973 (6)0.6357 (4)0.3011 (3)0.0207 (8)
N20.8530 (6)0.4641 (4)0.2683 (3)0.0193 (8)
N30.7532 (6)0.8733 (4)0.1407 (3)0.0208 (8)
N40.8477 (6)0.6513 (4)0.0459 (3)0.0191 (8)
C70.6336 (8)0.6725 (4)0.2310 (3)0.0181 (9)
C80.5401 (8)0.5140 (5)0.3545 (3)0.0214 (10)
H80.44400.48420.40360.026*
C90.7207 (8)0.4295 (4)0.3405 (3)0.0215 (10)
H90.75140.34570.38280.026*
C100.8064 (7)0.5845 (4)0.2107 (3)0.0178 (9)
C110.5864 (8)0.8134 (5)0.1779 (3)0.0205 (10)
C120.7097 (8)1.0002 (5)0.0970 (3)0.0213 (10)
H120.82551.04420.07090.026*
C130.5087 (8)1.0721 (5)0.0870 (3)0.0223 (10)
H130.48731.16240.05500.027*
C140.3393 (8)1.0090 (5)0.1249 (3)0.0226 (10)
H140.19851.05520.11920.027*
C150.3776 (8)0.8781 (5)0.1710 (3)0.0205 (10)
H150.26380.83270.19770.025*
C160.9470 (8)0.6132 (4)0.1261 (3)0.0189 (9)
C170.9704 (9)0.6689 (5)−0.0306 (4)0.0244 (10)
H170.90380.6948−0.08840.029*
C181.1934 (8)0.6509 (5)−0.0298 (4)0.0241 (10)
H181.27510.6654−0.08570.029*
C191.2907 (8)0.6117 (5)0.0544 (4)0.0242 (10)
H191.44090.59790.05730.029*
C201.1658 (7)0.5928 (4)0.1341 (3)0.0191 (10)
H201.22810.56650.19290.023*
U11U22U33U12U13U23
I10.0227 (2)0.0220 (2)0.0325 (2)0.00505 (13)−0.00955 (14)−0.01061 (15)
I20.02250 (19)0.01648 (18)0.02206 (19)0.00093 (12)−0.00667 (13)−0.00489 (13)
F10.0179 (14)0.0322 (16)0.0267 (16)−0.0065 (12)0.0029 (12)−0.0084 (13)
F20.0296 (15)0.0220 (14)0.0202 (15)−0.0091 (12)−0.0007 (12)−0.0006 (12)
F30.0172 (13)0.0283 (16)0.0228 (15)−0.0035 (12)0.0027 (11)−0.0031 (12)
F40.0250 (15)0.0171 (14)0.0234 (15)−0.0021 (11)−0.0037 (12)0.0032 (11)
C10.017 (2)0.018 (2)0.021 (2)0.0012 (18)−0.0094 (18)−0.0060 (19)
C20.018 (2)0.021 (2)0.018 (2)−0.0044 (18)0.0010 (18)−0.0076 (18)
C30.025 (2)0.016 (2)0.015 (2)−0.0054 (18)−0.0046 (18)−0.0036 (17)
C40.023 (2)0.016 (2)0.016 (2)−0.0024 (18)−0.0045 (18)−0.0042 (18)
C50.017 (2)0.016 (2)0.015 (2)0.0020 (17)−0.0042 (17)−0.0019 (17)
C60.022 (2)0.015 (2)0.012 (2)−0.0050 (18)−0.0021 (18)−0.0007 (17)
N10.0182 (19)0.0185 (19)0.024 (2)−0.0023 (15)−0.0028 (16)−0.0035 (16)
N20.0173 (19)0.0190 (19)0.021 (2)−0.0005 (15)−0.0022 (16)−0.0060 (16)
N30.022 (2)0.020 (2)0.022 (2)−0.0056 (16)−0.0040 (16)−0.0063 (16)
N40.024 (2)0.0169 (19)0.017 (2)−0.0011 (15)−0.0036 (16)−0.0062 (15)
C70.022 (2)0.016 (2)0.016 (2)−0.0019 (18)−0.0047 (18)−0.0044 (18)
C80.023 (2)0.021 (2)0.019 (2)−0.0053 (19)−0.0006 (19)−0.0020 (18)
C90.030 (3)0.012 (2)0.022 (2)−0.0043 (19)−0.004 (2)−0.0030 (18)
C100.022 (2)0.015 (2)0.018 (2)−0.0013 (17)−0.0074 (18)−0.0069 (17)
C110.026 (2)0.016 (2)0.020 (2)−0.0035 (18)0.0012 (19)−0.0052 (18)
C120.027 (2)0.020 (2)0.019 (2)−0.0094 (19)0.0001 (19)−0.0038 (18)
C130.033 (3)0.014 (2)0.020 (2)−0.0060 (19)−0.006 (2)−0.0026 (18)
C140.025 (2)0.018 (2)0.022 (2)0.0032 (19)−0.003 (2)−0.0050 (19)
C150.022 (2)0.020 (2)0.020 (2)−0.0082 (19)−0.0005 (19)−0.0024 (19)
C160.024 (2)0.0089 (19)0.023 (2)−0.0007 (17)−0.0031 (19)−0.0027 (17)
C170.037 (3)0.014 (2)0.019 (2)0.000 (2)−0.006 (2)−0.0005 (18)
C180.031 (3)0.017 (2)0.023 (3)−0.0058 (19)0.007 (2)−0.0056 (19)
C190.021 (2)0.023 (2)0.029 (3)−0.0014 (19)−0.001 (2)−0.009 (2)
C200.016 (2)0.014 (2)0.023 (2)−0.0018 (17)−0.0075 (18)0.0032 (18)
I1—C12.068 (5)C7—C111.497 (6)
I2—C42.085 (5)C8—C91.385 (7)
F1—C21.339 (5)C8—H80.9500
F2—C31.348 (5)C9—H90.9500
F3—C51.348 (5)C10—C161.500 (7)
F4—C61.346 (5)C11—C151.395 (7)
C1—C61.385 (7)C12—C131.380 (7)
C1—C21.398 (7)C12—H120.9500
C2—C31.378 (7)C13—C141.382 (7)
C3—C41.383 (7)C13—H130.9500
C4—C51.392 (7)C14—C151.377 (7)
C5—C61.382 (6)C14—H140.9500
N1—C81.331 (6)C15—H150.9500
N1—C71.340 (6)C16—C201.389 (6)
N2—C91.340 (7)C17—C181.408 (7)
N2—C101.345 (6)C17—H170.9500
N3—C121.333 (6)C18—C191.383 (7)
N3—C111.349 (6)C18—H180.9500
N4—C161.338 (6)C19—C201.383 (7)
N4—C171.337 (7)C19—H190.9500
C7—C101.402 (7)C20—H200.9500
C6—C1—C2117.4 (4)N2—C10—C16115.6 (4)
C6—C1—I1121.8 (4)C7—C10—C16124.4 (4)
C2—C1—I1120.8 (4)N3—C11—C15122.8 (4)
F1—C2—C3119.2 (4)N3—C11—C7117.1 (4)
F1—C2—C1120.0 (4)C15—C11—C7120.1 (4)
C3—C2—C1120.8 (4)N3—C12—C13124.7 (4)
F2—C3—C2117.9 (4)N3—C12—H12117.6
F2—C3—C4120.1 (4)C13—C12—H12117.6
C2—C3—C4122.0 (4)C14—C13—C12118.1 (4)
C3—C4—C5117.1 (4)C14—C13—H13121.0
C3—C4—I2121.1 (4)C12—C13—H13121.0
C5—C4—I2121.7 (4)C13—C14—C15119.0 (5)
F3—C5—C6118.6 (4)C13—C14—H14120.5
F3—C5—C4120.1 (4)C15—C14—H14120.5
C6—C5—C4121.3 (4)C14—C15—C11118.9 (4)
F4—C6—C5118.5 (4)C14—C15—H15120.5
F4—C6—C1120.2 (4)C11—C15—H15120.5
C5—C6—C1121.4 (4)N4—C16—C20124.3 (5)
C8—N1—C7117.1 (4)N4—C16—C10115.5 (4)
C9—N2—C10117.8 (4)C20—C16—C10120.0 (4)
C12—N3—C11116.5 (4)N4—C17—C18123.3 (5)
C16—N4—C17116.7 (4)N4—C17—H17118.4
N1—C7—C10121.6 (4)C18—C17—H17118.4
N1—C7—C11114.6 (4)C19—C18—C17118.4 (5)
C10—C7—C11123.7 (4)C19—C18—H18120.8
N1—C8—C9121.9 (4)C17—C18—H18120.8
N1—C8—H8119.0C18—C19—C20118.9 (5)
C9—C8—H8119.0C18—C19—H19120.5
N2—C9—C8121.1 (4)C20—C19—H19120.5
N2—C9—H9119.5C16—C20—C19118.3 (5)
C8—C9—H9119.5C16—C20—H20120.8
N2—C10—C7120.0 (4)C19—C20—H20120.8
C6—C1—C2—F1−179.7 (4)C9—N2—C10—C16−174.1 (4)
I1—C1—C2—F10.1 (6)N1—C7—C10—N2−7.7 (7)
C6—C1—C2—C30.6 (7)C11—C7—C10—N2171.8 (4)
I1—C1—C2—C3−179.6 (4)N1—C7—C10—C16171.1 (4)
F1—C2—C3—F20.1 (7)C11—C7—C10—C16−9.4 (7)
C1—C2—C3—F2179.8 (4)C12—N3—C11—C150.7 (7)
F1—C2—C3—C4−179.6 (4)C12—N3—C11—C7−177.3 (4)
C1—C2—C3—C40.1 (7)N1—C7—C11—N3148.1 (4)
F2—C3—C4—C5179.3 (4)C10—C7—C11—N3−31.5 (7)
C2—C3—C4—C5−1.0 (7)N1—C7—C11—C15−29.9 (7)
F2—C3—C4—I2−3.4 (6)C10—C7—C11—C15150.5 (5)
C2—C3—C4—I2176.3 (4)C11—N3—C12—C13−0.5 (7)
C3—C4—C5—F3−178.1 (4)N3—C12—C13—C140.0 (8)
I2—C4—C5—F34.6 (6)C12—C13—C14—C150.3 (7)
C3—C4—C5—C61.2 (7)C13—C14—C15—C11−0.1 (7)
I2—C4—C5—C6−176.1 (3)N3—C11—C15—C14−0.4 (8)
F3—C5—C6—F4−1.4 (6)C7—C11—C15—C14177.5 (5)
C4—C5—C6—F4179.2 (4)C17—N4—C16—C200.8 (7)
F3—C5—C6—C1178.8 (4)C17—N4—C16—C10−175.5 (4)
C4—C5—C6—C1−0.6 (7)N2—C10—C16—N4124.0 (4)
C2—C1—C6—F4179.9 (4)C7—C10—C16—N4−54.8 (6)
I1—C1—C6—F40.0 (6)N2—C10—C16—C20−52.5 (6)
C2—C1—C6—C5−0.3 (7)C7—C10—C16—C20128.7 (5)
I1—C1—C6—C5179.9 (4)C16—N4—C17—C18−0.8 (7)
C8—N1—C7—C104.1 (7)N4—C17—C18—C190.8 (7)
C8—N1—C7—C11−175.5 (4)C17—C18—C19—C20−0.6 (7)
C7—N1—C8—C92.0 (7)N4—C16—C20—C19−0.6 (7)
C10—N2—C9—C81.1 (7)C10—C16—C20—C19175.5 (4)
N1—C8—C9—N2−4.8 (8)C18—C19—C20—C160.5 (7)
C9—N2—C10—C74.8 (7)
D—H···AD—HH···AD···AD—H···A
C8—H8···F40.952.543.145 (6)121
C9—H9···F40.952.463.100 (6)125
C18—H18···F2i0.952.523.341 (7)144
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C8—H8⋯F40.952.543.145 (6)121
C9—H9⋯F40.952.463.100 (6)125
C18—H18⋯F2i0.952.523.341 (7)144

Symmetry code: (i) .

  2 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.  1,2,4,5-Tetra-fluoro-3,6-diiodo-benzene-4-(pyridin-4-ylsulfan-yl)pyridine (1/1).

Authors:  Hadi D Arman; Trupta Kaulgud; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-09-30
  2 in total

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