1,2,4,5-Tetra­fluoro-3,6-diiodo­benzene–2,3-bis­(pyridin-2-yl)pyrazine (1/1)

Arman, H.D.; Kaulgud, T.; Tiekink, E.R.T.

doi:10.1107/S1600536810041668

organic compounds

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ISSN: 2056-9890

Volume 66| Part 11| November 2010| Page o2885

https://doi.org/10.1107/S1600536810041668

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1,2,4,5-Tetrafluoro-3,6-diiodobenzene–2,3-bis(pyridin-2-yl)pyrazine (1/1)

Hadi D. Arman,^a Trupta Kaulgud ^a and Edward R. T. Tiekink ^b ^*

^aDepartment of Chemistry, The University of Texas at San Antonio, One UTSA Circle, San Antonio, Texas 78249-0698, USA, and ^bDepartment of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia
^*Correspondence e-mail: Edward.Tiekink@gmail.com

(Received 14 October 2010; accepted 15 October 2010; online 23 October 2010)

The components of the title 1:1 co-crystal, C₁₄H₁₀N₄·C₆F₄I₂, are connected via an N⋯I [2.959 (4) Å] halogen bond, in which the N atom is part of the relatively electron-rich pyrazine ring. The C₆F₄I₂ molecule 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 interactions [ring centroid(pyridyl)–ring centroid(benzene) = 3.678 (3) Å].

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: Metrangolo et al. (2008 ); Pennington et al. (2008 ).

Experimental

Crystal data

C₁₄H₁₀N₄·C₆F₄I₂
M_r = 636.04
Triclinic, $[P \overline 1]$
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[F² > 2σ(F²)] = 0.039
wR(F²) = 0.109
S = 1.09
3775 reflections
271 parameters
H-atom parameters constrained
Δρ_max = 1.32 e Å⁻³
Δρ_min = −1.20 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C8—H8⋯F4	0.95	2.54	3.145 (6)	121
C9—H9⋯F4	0.95	2.46	3.100 (6)	125
C18—H18⋯F2ⁱ	0.95	2.52	3.341 (7)	144
Symmetry code: (i) x+1, y+1, z-1.

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 ).

Supporting information

Crystal structure: contains datablocks general, I. DOI: https://doi.org/10.1107/S1600536810041668/hb5683sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810041668/hb5683Isup2.hkl

checkCIF report

Comment top

The title co-crystal was prepared during on-going studies investigating co-crystals with pyridine-type molecules (Broker & Tiekink, 2007; Broker et al., 2008) including halogen bonding (Arman et al., 2010). The co-crystallization experiment whereby equimolar amounts of 1,2,4,5-tetrafluoro-3,6-diiodobenzene and 2,3-bis(pyridin-2-yl)pyrazine were dissolved in methylene chloride resulted in the isolation of the title 1/1 co-crystal, (I).

The molecule of 1,2,4,5-tetrafluoro-3,6-diiodobenzene, Fig. 1, is flat with the r.m.s. deviation of the 12 constituent atoms being 0.038 Å [maximum deviation = 0.084 (1) Å for atom I2]. In the molecule of 2,3-bis(pyridin-2-yl)pyrazine, Fig. 2, the N3- and N4-pyridyl rings form dihedral angles of 31.3 (2) and 54.6 (2) ° with the pyrazine ring; the dihedral angle formed between the pyridyl rings = 60.2 (2) °.

The primary connection between the constituent molecules of (I) is a N2···I2 contact of 2.959 (4) Å, representing an halogen bond (Metrangolo et al., 2008; Pennington et al., 2008). Of note is the observation that the interaction involves a pyrazine-N rather than a pyridine-N, consistent with the N in the pyrazine ring being more electron rich. The molecules are stabilized in the crystal packing via a combination of C—H···F [the F4 atom is bifurcated], Table 1, and π···π interactions [ring centroid(N3,C11–C15)···ring centroid(C1–C6)ⁱ = 3.678 (3) Å for i: 1 - x, 1 - y, 1 - z], Fig. 3.

Related literature top

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: Metrangolo et al. (2008); Pennington et al. (2008).

Experimental top

Initially 1,2,4,5-tetrafluoro-3,6-diiodobenzene (Aldrich, 0.09 mmol) and 2,3-bis(pyridin-2-yl)pyrazine (Aldrich, 0.04 mmol) were dissolved in chloroform and after evaporation of the solvent, the powder was then dissolved in tetrahydrafuran (THF). Upon evaporation of THF, methylene chloride was added to the powder. Colourless prisms of (I) were formed after three days through slow evaporation of solvent, m. pt. 409–411 K.

Structure description top

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: Metrangolo et al. (2008); Pennington et al. (2008).

Computing details top

Data collection: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); cell refinement: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); data reduction: CrystalClear (Molecular Structure Corporation & Rigaku, 2005); 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).

Figures top

	Fig. 1. Molecular structure of 1,2,4,5-tetrafluoro-3,6-diiodobenzene found in the structure of (I) showing displacement ellipsoids at the 50% probability level
	Fig. 2. Molecular structure of 2,3-bis(pyridin-2-yl)pyrazine found in the structure of (I) showing displacement ellipsoids at the 50% probability level.
	Fig. 3. A view in projection down the a axis showing the unit-cell contents. The N···I, C—H···F and π···π interactions are shown as blue, orange and purple dashed lines, respectively.

1,2,4,5-Tetrafluoro-3,6-diiodobenzene–2,3-bis(pyridin-2-yl)pyrazine (1/1) top

Crystal data top

C₁₄H₁₀N₄·C₆F₄I₂	Z = 2
M_r = 636.04	F(000) = 600
Triclinic, P1	D_x = 2.148 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 6.3997 (15) Å	Cell parameters from 2870 reflections
b = 10.737 (2) Å	θ = 2.8–40.2°
c = 15.092 (4) Å	µ = 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

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3775 independent reflections
Radiation source: fine-focus sealed tube	3550 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.025
ω scans	θ_max = 26.0°, θ_min = 2.7°
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	h = −7→7
T_min = 0.504, T_max = 1.000	k = −13→13
5074 measured reflections	l = −18→18

Refinement top

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) = 0.109	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0647P)² + 2.2885P] where P = (F_o² + 2F_c²)/3
3775 reflections	(Δ/σ)_max = 0.001
271 parameters	Δρ_max = 1.32 e Å⁻³
0 restraints	Δρ_min = −1.20 e Å⁻³

Crystal data top

C₁₄H₁₀N₄·C₆F₄I₂	γ = 80.283 (12)°
M_r = 636.04	V = 983.3 (4) Å³
Triclinic, P1	Z = 2
a = 6.3997 (15) Å	Mo Kα radiation
b = 10.737 (2) Å	µ = 3.25 mm⁻¹
c = 15.092 (4) Å	T = 98 K
α = 74.237 (10)°	0.40 × 0.13 × 0.07 mm
β = 85.877 (11)°

Data collection top

Rigaku AFC12K/SATURN724 diffractometer	3775 independent reflections
Absorption correction: multi-scan (ABSCOR; Higashi, 1995)	3550 reflections with I > 2σ(I)
T_min = 0.504, T_max = 1.000	R_int = 0.025
5074 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.039	0 restraints
wR(F²) = 0.109	H-atom parameters constrained
S = 1.09	Δρ_max = 1.32 e Å⁻³
3775 reflections	Δρ_min = −1.20 e Å⁻³
271 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
I1	0.02819 (5)	0.31600 (3)	0.57773 (2)	0.02562 (13)
I2	0.78603 (5)	−0.24672 (3)	0.69360 (2)	0.02055 (12)
F1	0.0119 (4)	0.0318 (3)	0.7123 (2)	0.0253 (6)
F2	0.2992 (5)	−0.1842 (3)	0.7543 (2)	0.0243 (6)
F3	0.7961 (5)	0.0349 (3)	0.5483 (2)	0.0237 (6)
F4	0.5096 (5)	0.2523 (3)	0.5082 (2)	0.0235 (6)
C1	0.2526 (8)	0.1487 (5)	0.6091 (3)	0.0187 (10)
C2	0.2048 (7)	0.0342 (5)	0.6718 (3)	0.0183 (9)
C3	0.3548 (8)	−0.0770 (5)	0.6931 (3)	0.0185 (9)
C4	0.5573 (8)	−0.0806 (5)	0.6541 (3)	0.0184 (9)
C5	0.6036 (7)	0.0330 (4)	0.5907 (3)	0.0168 (9)
C6	0.4545 (8)	0.1452 (5)	0.5692 (3)	0.0168 (9)
N1	0.4973 (6)	0.6357 (4)	0.3011 (3)	0.0207 (8)
N2	0.8530 (6)	0.4641 (4)	0.2683 (3)	0.0193 (8)
N3	0.7532 (6)	0.8733 (4)	0.1407 (3)	0.0208 (8)
N4	0.8477 (6)	0.6513 (4)	0.0459 (3)	0.0191 (8)
C7	0.6336 (8)	0.6725 (4)	0.2310 (3)	0.0181 (9)
C8	0.5401 (8)	0.5140 (5)	0.3545 (3)	0.0214 (10)
H8	0.4440	0.4842	0.4036	0.026*
C9	0.7207 (8)	0.4295 (4)	0.3405 (3)	0.0215 (10)
H9	0.7514	0.3457	0.3828	0.026*
C10	0.8064 (7)	0.5845 (4)	0.2107 (3)	0.0178 (9)
C11	0.5864 (8)	0.8134 (5)	0.1779 (3)	0.0205 (10)
C12	0.7097 (8)	1.0002 (5)	0.0970 (3)	0.0213 (10)
H12	0.8255	1.0442	0.0709	0.026*
C13	0.5087 (8)	1.0721 (5)	0.0870 (3)	0.0223 (10)
H13	0.4873	1.1624	0.0550	0.027*
C14	0.3393 (8)	1.0090 (5)	0.1249 (3)	0.0226 (10)
H14	0.1985	1.0552	0.1192	0.027*
C15	0.3776 (8)	0.8781 (5)	0.1710 (3)	0.0205 (10)
H15	0.2638	0.8327	0.1977	0.025*
C16	0.9470 (8)	0.6132 (4)	0.1261 (3)	0.0189 (9)
C17	0.9704 (9)	0.6689 (5)	−0.0306 (4)	0.0244 (10)
H17	0.9038	0.6948	−0.0884	0.029*
C18	1.1934 (8)	0.6509 (5)	−0.0298 (4)	0.0241 (10)
H18	1.2751	0.6654	−0.0857	0.029*
C19	1.2907 (8)	0.6117 (5)	0.0544 (4)	0.0242 (10)
H19	1.4409	0.5979	0.0573	0.029*
C20	1.1658 (7)	0.5928 (4)	0.1341 (3)	0.0191 (10)
H20	1.2281	0.5665	0.1929	0.023*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.0227 (2)	0.0220 (2)	0.0325 (2)	0.00505 (13)	−0.00955 (14)	−0.01061 (15)
I2	0.02250 (19)	0.01648 (18)	0.02206 (19)	0.00093 (12)	−0.00667 (13)	−0.00489 (13)
F1	0.0179 (14)	0.0322 (16)	0.0267 (16)	−0.0065 (12)	0.0029 (12)	−0.0084 (13)
F2	0.0296 (15)	0.0220 (14)	0.0202 (15)	−0.0091 (12)	−0.0007 (12)	−0.0006 (12)
F3	0.0172 (13)	0.0283 (16)	0.0228 (15)	−0.0035 (12)	0.0027 (11)	−0.0031 (12)
F4	0.0250 (15)	0.0171 (14)	0.0234 (15)	−0.0021 (11)	−0.0037 (12)	0.0032 (11)
C1	0.017 (2)	0.018 (2)	0.021 (2)	0.0012 (18)	−0.0094 (18)	−0.0060 (19)
C2	0.018 (2)	0.021 (2)	0.018 (2)	−0.0044 (18)	0.0010 (18)	−0.0076 (18)
C3	0.025 (2)	0.016 (2)	0.015 (2)	−0.0054 (18)	−0.0046 (18)	−0.0036 (17)
C4	0.023 (2)	0.016 (2)	0.016 (2)	−0.0024 (18)	−0.0045 (18)	−0.0042 (18)
C5	0.017 (2)	0.016 (2)	0.015 (2)	0.0020 (17)	−0.0042 (17)	−0.0019 (17)
C6	0.022 (2)	0.015 (2)	0.012 (2)	−0.0050 (18)	−0.0021 (18)	−0.0007 (17)
N1	0.0182 (19)	0.0185 (19)	0.024 (2)	−0.0023 (15)	−0.0028 (16)	−0.0035 (16)
N2	0.0173 (19)	0.0190 (19)	0.021 (2)	−0.0005 (15)	−0.0022 (16)	−0.0060 (16)
N3	0.022 (2)	0.020 (2)	0.022 (2)	−0.0056 (16)	−0.0040 (16)	−0.0063 (16)
N4	0.024 (2)	0.0169 (19)	0.017 (2)	−0.0011 (15)	−0.0036 (16)	−0.0062 (15)
C7	0.022 (2)	0.016 (2)	0.016 (2)	−0.0019 (18)	−0.0047 (18)	−0.0044 (18)
C8	0.023 (2)	0.021 (2)	0.019 (2)	−0.0053 (19)	−0.0006 (19)	−0.0020 (18)
C9	0.030 (3)	0.012 (2)	0.022 (2)	−0.0043 (19)	−0.004 (2)	−0.0030 (18)
C10	0.022 (2)	0.015 (2)	0.018 (2)	−0.0013 (17)	−0.0074 (18)	−0.0069 (17)
C11	0.026 (2)	0.016 (2)	0.020 (2)	−0.0035 (18)	0.0012 (19)	−0.0052 (18)
C12	0.027 (2)	0.020 (2)	0.019 (2)	−0.0094 (19)	0.0001 (19)	−0.0038 (18)
C13	0.033 (3)	0.014 (2)	0.020 (2)	−0.0060 (19)	−0.006 (2)	−0.0026 (18)
C14	0.025 (2)	0.018 (2)	0.022 (2)	0.0032 (19)	−0.003 (2)	−0.0050 (19)
C15	0.022 (2)	0.020 (2)	0.020 (2)	−0.0082 (19)	−0.0005 (19)	−0.0024 (19)
C16	0.024 (2)	0.0089 (19)	0.023 (2)	−0.0007 (17)	−0.0031 (19)	−0.0027 (17)
C17	0.037 (3)	0.014 (2)	0.019 (2)	0.000 (2)	−0.006 (2)	−0.0005 (18)
C18	0.031 (3)	0.017 (2)	0.023 (3)	−0.0058 (19)	0.007 (2)	−0.0056 (19)
C19	0.021 (2)	0.023 (2)	0.029 (3)	−0.0014 (19)	−0.001 (2)	−0.009 (2)
C20	0.016 (2)	0.014 (2)	0.023 (2)	−0.0018 (17)	−0.0075 (18)	0.0032 (18)

Geometric parameters (Å, º) top

I1—C1	2.068 (5)	C7—C11	1.497 (6)
I2—C4	2.085 (5)	C8—C9	1.385 (7)
F1—C2	1.339 (5)	C8—H8	0.9500
F2—C3	1.348 (5)	C9—H9	0.9500
F3—C5	1.348 (5)	C10—C16	1.500 (7)
F4—C6	1.346 (5)	C11—C15	1.395 (7)
C1—C6	1.385 (7)	C12—C13	1.380 (7)
C1—C2	1.398 (7)	C12—H12	0.9500
C2—C3	1.378 (7)	C13—C14	1.382 (7)
C3—C4	1.383 (7)	C13—H13	0.9500
C4—C5	1.392 (7)	C14—C15	1.377 (7)
C5—C6	1.382 (6)	C14—H14	0.9500
N1—C8	1.331 (6)	C15—H15	0.9500
N1—C7	1.340 (6)	C16—C20	1.389 (6)
N2—C9	1.340 (7)	C17—C18	1.408 (7)
N2—C10	1.345 (6)	C17—H17	0.9500
N3—C12	1.333 (6)	C18—C19	1.383 (7)
N3—C11	1.349 (6)	C18—H18	0.9500
N4—C16	1.338 (6)	C19—C20	1.383 (7)
N4—C17	1.337 (7)	C19—H19	0.9500
C7—C10	1.402 (7)	C20—H20	0.9500

C6—C1—C2	117.4 (4)	N2—C10—C16	115.6 (4)
C6—C1—I1	121.8 (4)	C7—C10—C16	124.4 (4)
C2—C1—I1	120.8 (4)	N3—C11—C15	122.8 (4)
F1—C2—C3	119.2 (4)	N3—C11—C7	117.1 (4)
F1—C2—C1	120.0 (4)	C15—C11—C7	120.1 (4)
C3—C2—C1	120.8 (4)	N3—C12—C13	124.7 (4)
F2—C3—C2	117.9 (4)	N3—C12—H12	117.6
F2—C3—C4	120.1 (4)	C13—C12—H12	117.6
C2—C3—C4	122.0 (4)	C14—C13—C12	118.1 (4)
C3—C4—C5	117.1 (4)	C14—C13—H13	121.0
C3—C4—I2	121.1 (4)	C12—C13—H13	121.0
C5—C4—I2	121.7 (4)	C13—C14—C15	119.0 (5)
F3—C5—C6	118.6 (4)	C13—C14—H14	120.5
F3—C5—C4	120.1 (4)	C15—C14—H14	120.5
C6—C5—C4	121.3 (4)	C14—C15—C11	118.9 (4)
F4—C6—C5	118.5 (4)	C14—C15—H15	120.5
F4—C6—C1	120.2 (4)	C11—C15—H15	120.5
C5—C6—C1	121.4 (4)	N4—C16—C20	124.3 (5)
C8—N1—C7	117.1 (4)	N4—C16—C10	115.5 (4)
C9—N2—C10	117.8 (4)	C20—C16—C10	120.0 (4)
C12—N3—C11	116.5 (4)	N4—C17—C18	123.3 (5)
C16—N4—C17	116.7 (4)	N4—C17—H17	118.4
N1—C7—C10	121.6 (4)	C18—C17—H17	118.4
N1—C7—C11	114.6 (4)	C19—C18—C17	118.4 (5)
C10—C7—C11	123.7 (4)	C19—C18—H18	120.8
N1—C8—C9	121.9 (4)	C17—C18—H18	120.8
N1—C8—H8	119.0	C18—C19—C20	118.9 (5)
C9—C8—H8	119.0	C18—C19—H19	120.5
N2—C9—C8	121.1 (4)	C20—C19—H19	120.5
N2—C9—H9	119.5	C16—C20—C19	118.3 (5)
C8—C9—H9	119.5	C16—C20—H20	120.8
N2—C10—C7	120.0 (4)	C19—C20—H20	120.8

C6—C1—C2—F1	−179.7 (4)	C9—N2—C10—C16	−174.1 (4)
I1—C1—C2—F1	0.1 (6)	N1—C7—C10—N2	−7.7 (7)
C6—C1—C2—C3	0.6 (7)	C11—C7—C10—N2	171.8 (4)
I1—C1—C2—C3	−179.6 (4)	N1—C7—C10—C16	171.1 (4)
F1—C2—C3—F2	0.1 (7)	C11—C7—C10—C16	−9.4 (7)
C1—C2—C3—F2	179.8 (4)	C12—N3—C11—C15	0.7 (7)
F1—C2—C3—C4	−179.6 (4)	C12—N3—C11—C7	−177.3 (4)
C1—C2—C3—C4	0.1 (7)	N1—C7—C11—N3	148.1 (4)
F2—C3—C4—C5	179.3 (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—C15	150.5 (5)
C2—C3—C4—I2	176.3 (4)	C11—N3—C12—C13	−0.5 (7)
C3—C4—C5—F3	−178.1 (4)	N3—C12—C13—C14	0.0 (8)
I2—C4—C5—F3	4.6 (6)	C12—C13—C14—C15	0.3 (7)
C3—C4—C5—C6	1.2 (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—C14	177.5 (5)
C4—C5—C6—F4	179.2 (4)	C17—N4—C16—C20	0.8 (7)
F3—C5—C6—C1	178.8 (4)	C17—N4—C16—C10	−175.5 (4)
C4—C5—C6—C1	−0.6 (7)	N2—C10—C16—N4	124.0 (4)
C2—C1—C6—F4	179.9 (4)	C7—C10—C16—N4	−54.8 (6)
I1—C1—C6—F4	0.0 (6)	N2—C10—C16—C20	−52.5 (6)
C2—C1—C6—C5	−0.3 (7)	C7—C10—C16—C20	128.7 (5)
I1—C1—C6—C5	179.9 (4)	C16—N4—C17—C18	−0.8 (7)
C8—N1—C7—C10	4.1 (7)	N4—C17—C18—C19	0.8 (7)
C8—N1—C7—C11	−175.5 (4)	C17—C18—C19—C20	−0.6 (7)
C7—N1—C8—C9	2.0 (7)	N4—C16—C20—C19	−0.6 (7)
C10—N2—C9—C8	1.1 (7)	C10—C16—C20—C19	175.5 (4)
N1—C8—C9—N2	−4.8 (8)	C18—C19—C20—C16	0.5 (7)
C9—N2—C10—C7	4.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F4	0.95	2.54	3.145 (6)	121
C9—H9···F4	0.95	2.46	3.100 (6)	125
C18—H18···F2ⁱ	0.95	2.52	3.341 (7)	144

Symmetry code: (i) x+1, y+1, z−1.

Experimental details

Crystal data
Chemical formula	C₁₄H₁₀N₄·C₆F₄I₂
M_r	636.04
Crystal system, space group	Triclinic, P1
Temperature (K)	98
a, b, c (Å)	6.3997 (15), 10.737 (2), 15.092 (4)
α, β, γ (°)	74.237 (10), 85.877 (11), 80.283 (12)
V (Å³)	983.3 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	3.25
Crystal size (mm)	0.40 × 0.13 × 0.07

Data collection
Diffractometer	Rigaku AFC12K/SATURN724
Absorption correction	Multi-scan (ABSCOR; Higashi, 1995)
T_min, T_max	0.504, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5074, 3775, 3550
R_int	0.025
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.039, 0.109, 1.09
No. of reflections	3775
No. of parameters	271
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.32, −1.20

Computer programs: CrystalClear (Molecular Structure Corporation & Rigaku, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C8—H8···F4	0.95	2.54	3.145 (6)	121
C9—H9···F4	0.95	2.46	3.100 (6)	125
C18—H18···F2ⁱ	0.95	2.52	3.341 (7)	144

Symmetry code: (i) x+1, y+1, z−1.

References

Arman, H. D., Kaulgud, T. & Tiekink, E. R. T. (2010). Acta Cryst. E66, o2683. Web of Science CSD CrossRef IUCr Journals Google Scholar
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Pennington, W. T., Hanks, T. W. & Arman, H. D. (2008). Struct. Bond. 126, 65–104. Web of Science CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Westrip, S. P. (2010). J. Appl. Cryst. 43, 920–925. Web of Science CrossRef CAS IUCr Journals Google Scholar

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