2-Methyl-N-(pyrazin-2-yl)propanamide–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1)

Dziuk, B.; Ośmiałowski, B.; Zarychta, B.; Ejsmont, K.

doi:10.1107/S2414314616014668

organic compounds

IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161466

doi:10.1107/S2414314616014668

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2-Methyl-N-(pyrazin-2-yl)propanamide–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1)

Błażej Dziuk,^a ^* Borys Ośmiałowski,^b Bartosz Zarychta ^a and Krzysztof Ejsmont ^a

^aFaculty of Chemistry, University of Opole, Oleska 48, 45-052 Opole, Poland, and ^bFaculty of Chemical Technology and Engineering, University of Technology and Life Sciences, Seminaryjna 3, 85-326 Bydgoszcz, Poland
^*Correspondence e-mail: bdziuk@uni.opole.pl

Edited by M. Bolte, Goethe-Universität Frankfurt Germany (Received 16 September 2016; accepted 16 September 2016; online 27 September 2016)

In the title compound, C₈H₁₁N₃O·0.5C₆F₄I₂, molecules of ⁱPr-substituted pyrazine are co-crystallized with 1,4-diiodo-2,3,5,6-tetrafluorobenzene. The complete molecule of 1,4-diiodo-2,3,5,6-tetrafluorobenzene is generated by an inversion centre at the middle of the aromatic ring. Both molecules have normal geometry and the ⁱPr acylamine group is disordered over two sets of sites with an occupancy ratio of 0.51:0.49. In the crystal, the components are linked by I⋯N halogen bonds [2.830 (2) Å] and C—H⋯F interactions are observed.

Keywords: 2-aminopyrazine; halogen bonds; disorder; crystal structure.

CCDC reference: 1504625

Structure description

The aim of our study was obtain a series of crystals in which halogen bonding is one of the stabilizing forces. It is known that steric effects can be a factor that tunes the type of doubly hydrogen-bonded dimers both in solution and in the solid state. This has previously been shown for 2-acylaminopyridines (Ośmiałowski et al., 2010 ). Since steric effects may control the stability of the dimer our intention was to check if the dimer carrying a middle-size group (ⁱPr) would be disturbed in the solid state. The same ⁱPr group in 2-acylaminopyridine allowed efficient dimerization, while adamantyl did not either in 2-acylaminopyridine (Ośmiałowski et al., 2010) or in the analogous pyrazine (Dziuk et al., 2016 ). In the present work, the ⁱPr substituted-pyrazine was co-crystallized with 1,4-diiodo-2,3,5,6-tetrafluorobenzene (Fig. 1).

Figure 1
The molecular structure of the title compound with displacement ellipsoids drawn at the 50% probability level. For clarity, only one component of the disordered isopropylacylamine group group is shown.

The asymmetric unit comprises partially disordered 2-methyl-N-(pyrazin-2-yl)propanamide and a half-molecule of 1,2,4,5-tetrafluoro-3,6-diiodobenzene. The geometry of 2-methyl-N-(pyrazin-2-yl)propanamide is normal, and corresponds well with similar compounds (Ośmiałowski et al., 2010; Aakeröy et al., 2006 ; Dziuk et al.,2016). The ⁱPr acylamine group is disordered. The atoms are split between two positions with occupancy factors of 0.49 and 0.51.

In the crystal, I1⋯N2ⁱ [2.830 (2) Å; symmetry code: (i) −x + $[{3\over 2}]$ , y + $[{1\over 2}]$ , −z + $[{1\over 2}]$ ] halogen-bonding interactions connect the molecules into two C₈H₁₁N₃O^.C₆F₄I₂ units arranged in a herringbone packing agreement (Fig. 2). The units are connected through C—H⋯F contacts (Table 1), forming infinite layers. The estimated distance between adjacent layers is 3.636 Å. The 2,2-dimethyl-N-(pyrazin-2-yl)acetamide molecules are connected by N—H⋯O hydrogen bonds (Table 1).

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯F2ⁱ	0.93	2.46	3.388 (3)	178
C4—H4A⋯O1A	0.93	2.29	2.831 (5)	116
C4—H4A⋯O1B	0.93	2.21	2.867 (5)	127
C6A—H6AA⋯I1ⁱⁱ	0.98	3.24	4.035 (5)	140
N3A—H3AA⋯O1Aⁱ	0.86	2.85	3.681 (6)	164
N3B—H3BA⋯O1Bⁱ	0.86	2.13	2.976 (6)	170
Symmetry codes: (i) $[-x+{\script{3\over 2}}, y+{\script{1\over 2}}, -z+{\script{1\over 2}}]$ ; (ii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

Figure 2
The crystal packing of the title compound, viewed along the b axis.

Synthesis and crystallization

The parent pyrazine was obtained using a reported procedure by reaction of 2-aminopyrazine with isobutyryl chloride (Dziuk et al., 2016) in the presence of triethylamine. The co-crystallization was performed by mixing a 1:1 molar ratio of the studied compounds in chloroform followed by slow evaporation of the solvent.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2. The isopropylacylamine group is disordered over two positions. Refinement of the site-occupation factors lead to a ratio of 0.509 (7)/0.491 (7). Since they correlate with the displacement parameters, they were fixed at 0.51 and 0.49. The displacement parameters of the disordered atoms were restrained to be equal to those of the atoms to which they are bonded and they were restrained to an isotropic behaviour.

Table 2
Experimental details

Crystal data
Chemical formula	C₈H₁₁N₃O·0.5C₆F₄I₂
M_r	366.13
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	100
a, b, c (Å)	10.6503 (2), 10.6112 (2), 11.2086 (2)
β (°)	97.857 (2)
V (Å³)	1254.82 (4)
Z	4
Radiation type	Mo Kα
μ (mm⁻¹)	2.57
Crystal size (mm)	0.03 × 0.02 × 0.01

Data collection
Diffractometer	Oxford Diffraction Xcalibur
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ )
T_min, T_max	0.912, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	7645, 2209, 2073
R_int	0.011
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.015, 0.036, 1.02
No. of reflections	2209
No. of parameters	217
No. of restraints	256
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.63, −0.34
Computer programs: CrysAlis CCD (Oxford Diffraction, 2008 $[Oxford Diffraction (2008). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Abingdon, England.]$ ), SHELXS2013 and SHELXTL (Sheldrick, 2008 ) and SHELXL2013 (Sheldrick, 2015 ).

Structural data

CCDC reference: 1504625

Crystal structure: contains datablocks I, global. DOI: 10.1107/S2414314616014668/bt4027sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S2414314616014668/bt4027Isup2.hkl

checkCIF report

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2008); cell refinement: CrysAlis CCD (Oxford Diffraction, 2008); data reduction: CrysAlis CCD (Oxford Diffraction, 2008); program(s) used to solve structure: SHELXS2013 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2013 (Sheldrick, 2015); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL2013 (Sheldrick, 2015).

2-Methyl-N-(pyrazin-2-yl)propanamide–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1) top

Crystal data top

C₈H₁₁N₃O·0.5C₆F₄I₂	F(000) = 708
M_r = 366.13	D_x = 1.938 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
a = 10.6503 (2) Å	Cell parameters from 7645 reflections
b = 10.6112 (2) Å	θ = 3.1–25.0°
c = 11.2086 (2) Å	µ = 2.57 mm⁻¹
β = 97.857 (2)°	T = 100 K
V = 1254.82 (4) Å³	Plate, colourless
Z = 4	0.03 × 0.02 × 0.01 mm

Data collection top

Oxford Diffraction Xcalibur diffractometer	2209 independent reflections
Radiation source: fine-focus sealed tube	2073 reflections with I > 2σ(I)
Detector resolution: 1024 x 1024 with blocks 2 x 2 pixels mm^-1	R_int = 0.011
ω scans	θ_max = 25.0°, θ_min = 3.1°
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2008)	h = −12→9
T_min = 0.912, T_max = 1.000	k = −12→12
7645 measured reflections	l = −13→13

Refinement top

Refinement on F²	256 restraints
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.015	H-atom parameters constrained
wR(F²) = 0.036	w = 1/[σ²(F_o²) + (0.0188P)² + 1.2735P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.002
2209 reflections	Δρ_max = 0.63 e Å⁻³
217 parameters	Δρ_min = −0.34 e Å⁻³

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.

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

	x	y	z	U_iso*/U_eq	Occ. (<1)
I1	0.94381 (2)	0.23915 (2)	0.78247 (2)	0.01620 (6)
F1	1.07201 (16)	0.23859 (11)	1.06151 (12)	0.0363 (4)
F2	0.89029 (14)	−0.05718 (12)	0.77398 (11)	0.0293 (3)
N1	0.66750 (18)	0.17037 (18)	−0.00151 (18)	0.0265 (4)
N2	0.61307 (16)	−0.05394 (16)	−0.12506 (15)	0.0179 (4)
C1	0.6789 (2)	0.0598 (2)	0.05489 (19)	0.0227 (5)
C2	0.6296 (2)	0.1675 (2)	−0.1196 (2)	0.0240 (5)
H2A	0.6214	0.2432	−0.1618	0.029*
C3	0.60207 (19)	0.05664 (19)	−0.18178 (19)	0.0190 (4)
H3A	0.5755	0.0591	−0.2643	0.023*
C4	0.6516 (2)	−0.0536 (2)	−0.00667 (18)	0.0204 (4)
H4A	0.6604	−0.1294	0.0352	0.024*
N3A	0.7268 (4)	0.0522 (4)	0.1841 (4)	0.0145 (10)	0.51
H3AA	0.7500	0.1233	0.2169	0.017*	0.51
O1A	0.7017 (4)	−0.1154 (5)	0.2410 (4)	0.0215 (10)	0.51
C5A	0.7410 (5)	−0.0491 (6)	0.2620 (4)	0.0156 (10)	0.51
C6A	0.7550 (4)	0.0511 (4)	0.3894 (4)	0.0182 (8)	0.51
H6AA	0.7166	0.1344	0.3734	0.022*	0.51
C7A	0.6945 (8)	−0.0258 (8)	0.4767 (9)	0.028 (2)	0.51
H7AA	0.6988	0.0188	0.5517	0.042*	0.51
H7AB	0.7383	−0.1047	0.4897	0.042*	0.51
H7AC	0.6074	−0.0410	0.4452	0.042*	0.51
C8A	0.8965 (5)	0.0535 (6)	0.4199 (5)	0.0451 (13)	0.51
H8AA	0.9196	0.1040	0.4905	0.068*	0.51
H8AB	0.9332	0.0888	0.3538	0.068*	0.51
H8AC	0.9274	−0.0308	0.4349	0.068*	0.51
N3B	0.7097 (4)	0.0885 (4)	0.1731 (4)	0.0140 (11)	0.49
H3BA	0.7229	0.1661	0.1934	0.017*	0.49
O1B	0.7231 (4)	−0.1556 (4)	0.2297 (4)	0.0187 (10)	0.49
C5B	0.7207 (4)	−0.0021 (5)	0.2620 (4)	0.0121 (10)	0.49
C6B	0.7841 (4)	−0.0153 (4)	0.3948 (4)	0.0140 (8)	0.49
H6BA	0.8511	−0.0793	0.4058	0.017*	0.49
C7B	0.6716 (7)	−0.0435 (8)	0.4675 (8)	0.0176 (16)	0.49
H7BA	0.7041	−0.0554	0.5510	0.026*	0.49
H7BB	0.6284	−0.1184	0.4366	0.026*	0.49
H7BC	0.6136	0.0262	0.4596	0.026*	0.49
C8B	0.8330 (4)	0.1179 (4)	0.4183 (4)	0.0203 (9)	0.49
H8BA	0.8771	0.1234	0.4988	0.030*	0.49
H8BB	0.7629	0.1756	0.4094	0.030*	0.49
H8BC	0.8898	0.1389	0.3618	0.030*	0.49
C9	0.97972 (18)	0.09653 (18)	0.91234 (17)	0.0146 (4)
C10	1.0348 (2)	0.12112 (18)	1.02892 (18)	0.0188 (4)
C11	0.94546 (19)	−0.02697 (19)	0.88570 (18)	0.0168 (4)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
I1	0.02291 (8)	0.01364 (8)	0.01189 (8)	0.00054 (5)	0.00183 (5)	0.00207 (5)
F1	0.0709 (11)	0.0135 (6)	0.0202 (7)	−0.0117 (6)	−0.0093 (7)	0.0003 (5)
F2	0.0500 (8)	0.0209 (6)	0.0134 (6)	−0.0078 (6)	−0.0085 (6)	−0.0003 (5)
N1	0.0237 (10)	0.0266 (10)	0.0299 (11)	−0.0054 (8)	0.0066 (8)	−0.0123 (8)
N2	0.0209 (9)	0.0187 (9)	0.0141 (9)	−0.0022 (7)	0.0026 (7)	−0.0027 (7)
C1	0.0160 (10)	0.0363 (13)	0.0169 (11)	−0.0085 (9)	0.0063 (9)	−0.0085 (9)
C2	0.0229 (11)	0.0191 (11)	0.0303 (13)	−0.0013 (9)	0.0053 (9)	0.0004 (9)
C3	0.0201 (11)	0.0228 (11)	0.0145 (10)	0.0002 (8)	0.0044 (8)	0.0000 (8)
C4	0.0215 (11)	0.0249 (11)	0.0148 (11)	−0.0055 (9)	0.0028 (9)	0.0010 (8)
N3A	0.0159 (13)	0.0136 (13)	0.0136 (13)	0.0007 (9)	0.0003 (9)	−0.0022 (9)
O1A	0.0263 (17)	0.0198 (17)	0.0177 (15)	0.0012 (15)	0.0009 (13)	0.0009 (14)
C5A	0.0153 (13)	0.0164 (13)	0.0154 (13)	0.0006 (10)	0.0026 (9)	0.0017 (9)
C6A	0.0192 (12)	0.0183 (12)	0.0171 (11)	0.0010 (9)	0.0021 (9)	−0.0007 (9)
C7A	0.032 (3)	0.027 (3)	0.026 (3)	−0.0028 (18)	0.0053 (18)	0.0005 (16)
C8A	0.0382 (19)	0.057 (2)	0.039 (2)	−0.0001 (17)	0.0031 (16)	−0.0132 (16)
N3B	0.0150 (13)	0.0136 (13)	0.0131 (13)	0.0009 (9)	0.0005 (9)	−0.0006 (9)
O1B	0.0217 (16)	0.0184 (17)	0.0157 (15)	0.0061 (14)	0.0018 (12)	−0.0010 (13)
C5B	0.0118 (13)	0.0119 (13)	0.0127 (13)	−0.0011 (9)	0.0023 (9)	−0.0007 (9)
C6B	0.0146 (11)	0.0141 (11)	0.0129 (11)	−0.0001 (9)	0.0008 (9)	0.0002 (9)
C7B	0.018 (2)	0.023 (2)	0.013 (2)	−0.0051 (16)	0.0037 (16)	0.0014 (15)
C8B	0.0250 (16)	0.0171 (15)	0.0173 (16)	−0.0028 (14)	−0.0019 (14)	0.0003 (13)
C9	0.0166 (10)	0.0144 (10)	0.0131 (10)	0.0022 (8)	0.0034 (8)	0.0028 (7)
C10	0.0263 (11)	0.0118 (9)	0.0180 (11)	−0.0025 (8)	0.0014 (9)	−0.0015 (8)
C11	0.0204 (11)	0.0187 (10)	0.0106 (10)	−0.0004 (8)	−0.0006 (8)	−0.0013 (8)

Geometric parameters (Å, º) top

I1—C9	2.0983 (19)	C7A—H7AB	0.9600
F1—C10	1.343 (2)	C7A—H7AC	0.9600
F2—C11	1.347 (2)	C8A—H8AA	0.9600
N1—C2	1.330 (3)	C8A—H8AB	0.9600
N1—C1	1.330 (3)	C8A—H8AC	0.9600
N2—C3	1.332 (3)	N3B—C5B	1.378 (7)
N2—C4	1.334 (3)	N3B—H3BA	0.8600
C1—N3B	1.356 (5)	O1B—C5B	1.670 (6)
C1—C4	1.398 (3)	C5B—C6B	1.554 (6)
C1—N3A	1.471 (5)	C6B—C8B	1.517 (6)
C2—C3	1.379 (3)	C6B—C7B	1.567 (9)
C2—H2A	0.9300	C6B—H6BA	0.9800
C3—H3A	0.9300	C7B—H7BA	0.9600
C4—H4A	0.9300	C7B—H7BB	0.9600
N3A—C5A	1.380 (7)	C7B—H7BC	0.9600
N3A—H3AA	0.8600	C8B—H8BA	0.9600
O1A—C5A	0.836 (6)	C8B—H8BB	0.9600
C5A—C6A	1.770 (7)	C8B—H8BC	0.9600
C6A—C7A	1.487 (10)	C9—C11	1.382 (3)
C6A—C8A	1.500 (7)	C9—C10	1.382 (3)
C6A—H6AA	0.9800	C10—C11ⁱ	1.379 (3)
C7A—H7AA	0.9600	C11—C10ⁱ	1.379 (3)

C2—N1—C1	116.62 (19)	C6A—C8A—H8AC	109.5
C3—N2—C4	117.87 (18)	H8AA—C8A—H8AC	109.5
N1—C1—N3B	105.1 (3)	H8AB—C8A—H8AC	109.5
N1—C1—C4	121.70 (19)	C1—N3B—C5B	122.3 (4)
N3B—C1—C4	133.0 (3)	C1—N3B—H3BA	118.8
N1—C1—N3A	120.9 (2)	C5B—N3B—H3BA	118.8
C4—C1—N3A	117.4 (3)	N3B—C5B—C6B	137.6 (4)
N1—C2—C3	122.5 (2)	N3B—C5B—O1B	121.8 (4)
N1—C2—H2A	118.7	C6B—C5B—O1B	95.8 (4)
C3—C2—H2A	118.7	C8B—C6B—C5B	100.2 (3)
N2—C3—C2	120.77 (19)	C8B—C6B—C7B	110.8 (5)
N2—C3—H3A	119.6	C5B—C6B—C7B	104.6 (4)
C2—C3—H3A	119.6	C8B—C6B—H6BA	113.4
N2—C4—C1	120.5 (2)	C5B—C6B—H6BA	113.4
N2—C4—H4A	119.7	C7B—C6B—H6BA	113.4
C1—C4—H4A	119.7	C6B—C7B—H7BA	109.5
C5A—N3A—C1	131.2 (4)	C6B—C7B—H7BB	109.5
C5A—N3A—H3AA	114.4	H7BA—C7B—H7BB	109.5
C1—N3A—H3AA	114.4	C6B—C7B—H7BC	109.5
O1A—C5A—N3A	118.0 (6)	H7BA—C7B—H7BC	109.5
O1A—C5A—C6A	135.7 (6)	H7BB—C7B—H7BC	109.5
N3A—C5A—C6A	91.8 (4)	C6B—C8B—H8BA	109.5
C7A—C6A—C8A	111.8 (5)	C6B—C8B—H8BB	109.5
C7A—C6A—C5A	101.9 (5)	H8BA—C8B—H8BB	109.5
C8A—C6A—C5A	99.5 (4)	C6B—C8B—H8BC	109.5
C7A—C6A—H6AA	114.1	H8BA—C8B—H8BC	109.5
C8A—C6A—H6AA	114.1	H8BB—C8B—H8BC	109.5
C5A—C6A—H6AA	114.1	C11—C9—C10	116.65 (18)
C6A—C7A—H7AA	109.5	C11—C9—I1	121.09 (14)
C6A—C7A—H7AB	109.5	C10—C9—I1	122.23 (15)
H7AA—C7A—H7AB	109.5	F1—C10—C11ⁱ	118.16 (18)
C6A—C7A—H7AC	109.5	F1—C10—C9	120.23 (18)
H7AA—C7A—H7AC	109.5	C11ⁱ—C10—C9	121.60 (19)
H7AB—C7A—H7AC	109.5	F2—C11—C10ⁱ	118.57 (18)
C6A—C8A—H8AA	109.5	F2—C11—C9	119.68 (17)
C6A—C8A—H8AB	109.5	C10ⁱ—C11—C9	121.75 (18)
H8AA—C8A—H8AB	109.5

Symmetry code: (i) −x+2, −y, −z+2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···F2ⁱⁱ	0.93	2.46	3.388 (3)	178
C4—H4A···O1A	0.93	2.29	2.831 (5)	116
C4—H4A···O1B	0.93	2.21	2.867 (5)	127
C6A—H6AA···I1ⁱⁱⁱ	0.98	3.24	4.035 (5)	140
N3A—H3AA···O1Aⁱⁱ	0.86	2.85	3.681 (6)	164
N3B—H3BA···O1Bⁱⁱ	0.86	2.13	2.976 (6)	170

Symmetry codes: (ii) −x+3/2, y+1/2, −z+1/2; (iii) x−1/2, −y+1/2, z−1/2.

References

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IUCrDATA

ISSN: 2414-3146

Volume 1| Part 9| September 2016| x161466

doi:10.1107/S2414314616014668

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

2-Methyl-N-(pyrazin-2-yl)propanamide–1,2,4,5-tetra­fluoro-3,6-di­iodo­benzene (2/1)

Structure description

Synthesis and crystallization

Refinement

Structural data

References

organic compounds

2-Methyl-N-(pyrazin-2-yl)propanamide–1,2,4,5-tetrafluoro-3,6-diiodobenzene (2/1)