N-(2-Phen­oxy­phen­yl)pyrazine-2-carboxamide

Noroozi Tisseh, M.; Kargar Razi, M.; Khavasi, H.R.

doi:10.1107/S1600536812041050

organic compounds

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ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3161

doi:10.1107/S1600536812041050

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N-(2-Phenoxyphenyl)pyrazine-2-carboxamide

Mehri Noroozi Tisseh,^a ^* Maryam Kargar Razi ^a and Hamid Reza Khavasi ^b

^aDepartment of Chemistry, Islamic Azad University, North Tehran Branch, Tehran, Iran, and ^bDepartment of Chemistry, Shahid Beheshti University, G. C., Evin, Tehran, 1983963113, Iran
^*Correspondence e-mail: mehri.noroozi@gmail.com

(Received 28 September 2012; accepted 30 September 2012; online 20 October 2012)

In the title compound, C₁₇H₁₃N₃O₂, the pyrazine ring is oriented at 1.65 (11) and 88.33 (17)° with respect to the benzene rings. The benzene rings are nearly perpendicular to each other [dihedral angle 87.14 (17)°]. In the crystal, a weak C—H⋯N hydrogen bond occurs.

Related literature

For related structures, see: Wardell et al. (2008 ); de Lima Ferreira et al. (2010 ).

Experimental

Crystal data

C₁₇H₁₃N₃O₂
M_r = 291.30
Triclinic, $[P \overline 1]$
a = 5.0913 (10) Å
b = 11.769 (2) Å
c = 12.268 (3) Å
α = 91.058 (16)°
β = 94.541 (16)°
γ = 101.648 (15)°
V = 717.3 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.09 mm⁻¹
T = 298 K
0.40 × 0.20 × 0.15 mm

Data collection

Stoe IPDS II diffractometer
5966 measured reflections
2811 independent reflections
1923 reflections with I > 2σ(I)
R_int = 0.055

Refinement

R[F² > 2σ(F²)] = 0.062
wR(F²) = 0.132
S = 1.07
2811 reflections
199 parameters
H-atom parameters constrained
Δρ_max = 0.13 e Å⁻³
Δρ_min = −0.16 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2⋯N2ⁱ	0.93	2.62	3.439 (3)	147
Symmetry code: (i) -x+3, -y+1, -z+1.

Data collection: X-AREA (Stoe & Cie, 2005 ); cell refinement: X-AREA; data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812041050/xu5626sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812041050/xu5626Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812041050/xu5626Isup3.cml

checkCIF report

Comment top

The carboxamide [C(O)NH] group, ubiquitous throughout the nature in the primary structure of proteins, is an important ligand construction unit for coordination chemists. Pyrazine carboxamides are available from condensation reactions between pyrazine acid and amines, promoted by coupling agents such as triphenylphosphite (Wardell et al. (2008); de Lima Ferreira et al. (2010)). As part of our ongoing studies in this area, we report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the pyrazine ring is oriented with respect to the two benzene rings at 1.65 (11) and 88.33 (17)°, respectively, and the two benzenerings are nearly perpendicular to each other [dihedral angle 87.14 (17)°]. In the crystal structure, intermolecular C—H···N non-classical hydrogen bonds (Table 1, Fig. 2) may stabilize the structure.

Related literature top

For related structures, see: Wardell et al. (2008); de Lima Ferreira et al. (2010).

Experimental top

2-Pyridinedicarboxylic acid (0.124 g, 1 mmol) was suspended in pyridine (10 ml). 8-aminoquinoline (0.182 g, 1 mmol) was added to the mixture, and the mixture was stirred at 313–318 K, for 10 min. Triphenylphosphite (2 mmol, 0..53 ml) was added dropwise to the resulting solution. The temperature of the reaction mixture was increased to 363–373 K, and the mixture was magnetically stirred for 4 h. After cooling to room temperature, the reaction mixture was left in the hood for 24 h. The white precipitate was filtered off. Recrystallization was achieved by diethyl ether diffusion into a chloroform solution of the compound at room temperature (yield; 78%, m.p. 550 K).

Computing details top

Data collection: X-AREA (Stoe & Cie, 2005); cell refinement: X-AREA (Stoe & Cie, 2005); data reduction: X-RED (Stoe & Cie, 2005); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level. Hydrogen bonds are shown as dashed lines.
	Fig. 2. Unit-cell packing diagram for title molecule in a-direction. Hydrogen bonds and C—H···pi interactions are shown as dashed lines.

N-(2-Phenoxyphenyl)pyrazine-2-carboxamide top

Crystal data top

C₁₇H₁₃N₃O₂	Z = 2
M_r = 291.30	F(000) = 304
Triclinic, P1	D_x = 1.349 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 5.0913 (10) Å	Cell parameters from 5966 reflections
b = 11.769 (2) Å	θ = 2.4–26.0°
c = 12.268 (3) Å	µ = 0.09 mm⁻¹
α = 91.058 (16)°	T = 298 K
β = 94.541 (16)°	Block, yellow
γ = 101.648 (15)°	0.40 × 0.20 × 0.15 mm
V = 717.3 (3) Å³

Data collection top

Stoe IPDS II diffractometer	1923 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.055
Graphite monochromator	θ_max = 26.0°, θ_min = 2.4°
rotation method scans	h = −6→6
5966 measured reflections	k = −14→13
2811 independent reflections	l = −15→15

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)] = 0.062	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.132	H-atom parameters constrained
S = 1.07	w = 1/[σ²(F_o²) + (0.0432P)² + 0.2101P] where P = (F_o² + 2F_c²)/3
2811 reflections	(Δ/σ)_max = 0.002
199 parameters	Δρ_max = 0.13 e Å⁻³
0 restraints	Δρ_min = −0.16 e Å⁻³

Crystal data top

C₁₇H₁₃N₃O₂	γ = 101.648 (15)°
M_r = 291.30	V = 717.3 (3) Å³
Triclinic, P1	Z = 2
a = 5.0913 (10) Å	Mo Kα radiation
b = 11.769 (2) Å	µ = 0.09 mm⁻¹
c = 12.268 (3) Å	T = 298 K
α = 91.058 (16)°	0.40 × 0.20 × 0.15 mm
β = 94.541 (16)°

Data collection top

Stoe IPDS II diffractometer	1923 reflections with I > 2σ(I)
5966 measured reflections	R_int = 0.055
2811 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.062	0 restraints
wR(F²) = 0.132	H-atom parameters constrained
S = 1.07	Δρ_max = 0.13 e Å⁻³
2811 reflections	Δρ_min = −0.16 e Å⁻³
199 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
C1	1.1804 (5)	0.6963 (2)	0.4406 (2)	0.0618 (7)
H1	1.2440	0.7617	0.4861	0.074*
C2	1.2999 (5)	0.6018 (2)	0.4538 (2)	0.0593 (6)
H2	1.4410	0.6053	0.5076	0.071*
C3	1.0170 (5)	0.50713 (19)	0.3160 (2)	0.0567 (6)
H3	0.9552	0.4419	0.2700	0.068*
C4	0.8953 (4)	0.60172 (17)	0.30288 (18)	0.0462 (5)
C5	0.6677 (5)	0.59753 (18)	0.21628 (18)	0.0487 (5)
C6	0.3816 (4)	0.72817 (18)	0.13538 (17)	0.0460 (5)
C7	0.3225 (5)	0.83750 (18)	0.15148 (19)	0.0494 (5)
C8	0.1218 (5)	0.8733 (2)	0.0871 (2)	0.0603 (6)
H8	0.0841	0.9463	0.0990	0.072*
C9	−0.0227 (5)	0.7994 (2)	0.0046 (2)	0.0630 (7)
H9	−0.1591	0.8226	−0.0389	0.076*
C10	0.0351 (5)	0.6921 (2)	−0.0129 (2)	0.0661 (7)
H10	−0.0627	0.6430	−0.0686	0.079*
C11	0.2372 (5)	0.6556 (2)	0.05113 (19)	0.0578 (6)
H11	0.2759	0.5829	0.0378	0.069*
C12	0.4185 (5)	1.01105 (19)	0.2637 (2)	0.0546 (6)
C13	0.5372 (6)	1.1083 (2)	0.2146 (3)	0.0775 (8)
H13	0.6570	1.1042	0.1620	0.093*
C14	0.4776 (9)	1.2133 (3)	0.2440 (4)	0.1099 (15)
H14	0.5563	1.2805	0.2105	0.132*
C15	0.3048 (11)	1.2189 (4)	0.3215 (4)	0.130 (2)
H15	0.2653	1.2897	0.3416	0.156*
C16	0.1901 (10)	1.1207 (4)	0.3694 (4)	0.1308 (17)
H16	0.0724	1.1248	0.4229	0.157*
C17	0.2438 (7)	1.0151 (3)	0.3406 (3)	0.0896 (10)
H17	0.1622	0.9478	0.3732	0.108*
N1	0.9782 (4)	0.69785 (16)	0.36570 (16)	0.0559 (5)
N2	1.2183 (4)	0.50575 (17)	0.39150 (18)	0.0621 (6)
N3	0.5854 (4)	0.69918 (15)	0.20727 (15)	0.0500 (5)
H3B	0.6696	0.7542	0.2519	0.060*
O1	0.5723 (4)	0.50845 (13)	0.16236 (15)	0.0687 (5)
O2	0.4781 (4)	0.90428 (14)	0.23700 (15)	0.0714 (6)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0680 (16)	0.0505 (14)	0.0679 (16)	0.0208 (12)	−0.0077 (14)	−0.0076 (12)
C2	0.0609 (15)	0.0574 (15)	0.0646 (16)	0.0240 (12)	0.0036 (13)	0.0053 (12)
C3	0.0668 (15)	0.0416 (12)	0.0660 (16)	0.0218 (11)	0.0043 (13)	−0.0005 (11)
C4	0.0525 (13)	0.0382 (11)	0.0518 (13)	0.0152 (9)	0.0123 (10)	0.0034 (9)
C5	0.0589 (14)	0.0368 (11)	0.0532 (13)	0.0147 (10)	0.0100 (11)	0.0004 (10)
C6	0.0503 (12)	0.0410 (11)	0.0474 (12)	0.0116 (9)	0.0024 (10)	0.0021 (9)
C7	0.0518 (13)	0.0415 (12)	0.0539 (13)	0.0097 (10)	−0.0021 (11)	−0.0021 (10)
C8	0.0623 (15)	0.0496 (13)	0.0693 (16)	0.0186 (12)	−0.0103 (13)	−0.0005 (12)
C9	0.0600 (15)	0.0663 (16)	0.0606 (16)	0.0147 (12)	−0.0130 (13)	0.0036 (13)
C10	0.0739 (17)	0.0612 (16)	0.0579 (15)	0.0090 (13)	−0.0118 (13)	−0.0076 (12)
C11	0.0726 (16)	0.0435 (12)	0.0562 (14)	0.0118 (11)	0.0003 (13)	−0.0039 (10)
C12	0.0604 (14)	0.0384 (11)	0.0650 (15)	0.0196 (10)	−0.0166 (12)	−0.0082 (10)
C13	0.0769 (19)	0.0607 (17)	0.089 (2)	0.0049 (14)	−0.0105 (16)	0.0104 (15)
C14	0.128 (3)	0.0379 (16)	0.143 (4)	0.0001 (18)	−0.072 (3)	0.0060 (19)
C15	0.176 (5)	0.072 (2)	0.146 (4)	0.079 (3)	−0.094 (4)	−0.056 (3)
C16	0.169 (4)	0.132 (4)	0.119 (3)	0.100 (3)	0.009 (3)	−0.029 (3)
C17	0.105 (2)	0.075 (2)	0.100 (2)	0.0375 (18)	0.029 (2)	0.0095 (17)
N1	0.0652 (13)	0.0419 (10)	0.0638 (12)	0.0212 (9)	−0.0005 (11)	−0.0027 (9)
N2	0.0707 (14)	0.0496 (11)	0.0725 (14)	0.0292 (10)	0.0020 (12)	0.0035 (10)
N3	0.0595 (12)	0.0378 (10)	0.0541 (11)	0.0168 (8)	−0.0027 (9)	−0.0043 (8)
O1	0.0871 (13)	0.0430 (9)	0.0761 (12)	0.0212 (9)	−0.0087 (10)	−0.0118 (8)
O2	0.0782 (12)	0.0495 (10)	0.0877 (13)	0.0331 (9)	−0.0328 (10)	−0.0241 (9)

Geometric parameters (Å, º) top

C1—N1	1.328 (3)	C9—C10	1.371 (3)
C1—C2	1.378 (3)	C9—H9	0.9300
C1—H1	0.9300	C10—C11	1.387 (3)
C2—N2	1.327 (3)	C10—H10	0.9300
C2—H2	0.9300	C11—H11	0.9300
C3—N2	1.329 (3)	C12—C17	1.353 (4)
C3—C4	1.385 (3)	C12—C13	1.357 (4)
C3—H3	0.9300	C12—O2	1.391 (3)
C4—N1	1.333 (3)	C13—C14	1.379 (5)
C4—C5	1.501 (3)	C13—H13	0.9300
C5—O1	1.221 (3)	C14—C15	1.355 (6)
C5—N3	1.349 (3)	C14—H14	0.9300
C6—C11	1.390 (3)	C15—C16	1.352 (7)
C6—C7	1.393 (3)	C15—H15	0.9300
C6—N3	1.407 (3)	C16—C17	1.371 (5)
C7—C8	1.380 (3)	C16—H16	0.9300
C7—O2	1.390 (3)	C17—H17	0.9300
C8—C9	1.382 (3)	N3—H3B	0.8600
C8—H8	0.9300

N1—C1—C2	122.8 (2)	C11—C10—H10	119.5
N1—C1—H1	118.6	C10—C11—C6	119.7 (2)
C2—C1—H1	118.6	C10—C11—H11	120.2
N2—C2—C1	121.5 (2)	C6—C11—H11	120.2
N2—C2—H2	119.2	C17—C12—C13	121.5 (3)
C1—C2—H2	119.2	C17—C12—O2	118.3 (2)
N2—C3—C4	122.7 (2)	C13—C12—O2	120.3 (3)
N2—C3—H3	118.6	C12—C13—C14	119.0 (3)
C4—C3—H3	118.6	C12—C13—H13	120.5
N1—C4—C3	121.0 (2)	C14—C13—H13	120.5
N1—C4—C5	118.89 (18)	C15—C14—C13	120.2 (4)
C3—C4—C5	120.1 (2)	C15—C14—H14	119.9
O1—C5—N3	125.8 (2)	C13—C14—H14	119.9
O1—C5—C4	121.02 (19)	C16—C15—C14	119.5 (3)
N3—C5—C4	113.19 (18)	C16—C15—H15	120.2
C11—C6—C7	118.6 (2)	C14—C15—H15	120.2
C11—C6—N3	124.6 (2)	C15—C16—C17	121.3 (4)
C7—C6—N3	116.74 (19)	C15—C16—H16	119.3
C8—C7—O2	124.1 (2)	C17—C16—H16	119.3
C8—C7—C6	121.3 (2)	C12—C17—C16	118.4 (4)
O2—C7—C6	114.61 (19)	C12—C17—H17	120.8
C7—C8—C9	119.4 (2)	C16—C17—H17	120.8
C7—C8—H8	120.3	C1—N1—C4	116.03 (19)
C9—C8—H8	120.3	C2—N2—C3	115.9 (2)
C10—C9—C8	120.0 (2)	C5—N3—C6	129.29 (19)
C10—C9—H9	120.0	C5—N3—H3B	115.4
C8—C9—H9	120.0	C6—N3—H3B	115.4
C9—C10—C11	121.0 (2)	C7—O2—C12	118.20 (17)
C9—C10—H10	119.5

N1—C1—C2—N2	0.0 (4)	C13—C14—C15—C16	−0.3 (6)
N2—C3—C4—N1	0.8 (4)	C14—C15—C16—C17	−0.4 (6)
N2—C3—C4—C5	−179.7 (2)	C13—C12—C17—C16	−0.7 (5)
N1—C4—C5—O1	−174.6 (2)	O2—C12—C17—C16	178.2 (3)
C3—C4—C5—O1	6.0 (3)	C15—C16—C17—C12	0.9 (6)
N1—C4—C5—N3	4.8 (3)	C2—C1—N1—C4	0.1 (4)
C3—C4—C5—N3	−174.7 (2)	C3—C4—N1—C1	−0.4 (3)
C11—C6—C7—C8	1.2 (4)	C5—C4—N1—C1	−179.9 (2)
N3—C6—C7—C8	−178.5 (2)	C1—C2—N2—C3	0.4 (4)
C11—C6—C7—O2	−179.6 (2)	C4—C3—N2—C2	−0.8 (4)
N3—C6—C7—O2	0.7 (3)	O1—C5—N3—C6	−1.3 (4)
O2—C7—C8—C9	−179.4 (2)	C4—C5—N3—C6	179.3 (2)
C6—C7—C8—C9	−0.3 (4)	C11—C6—N3—C5	−5.7 (4)
C7—C8—C9—C10	−0.4 (4)	C7—C6—N3—C5	174.0 (2)
C8—C9—C10—C11	0.1 (4)	C8—C7—O2—C12	3.9 (4)
C9—C10—C11—C6	0.8 (4)	C6—C7—O2—C12	−175.3 (2)
O2—C12—C13—C14	−179.0 (2)	C17—C12—O2—C7	91.4 (3)
C12—C13—C14—C15	0.6 (5)	C13—C12—O2—C7	−89.7 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2ⁱ	0.93	2.62	3.439 (3)	147

Symmetry code: (i) −x+3, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₇H₁₃N₃O₂
M_r	291.30
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	5.0913 (10), 11.769 (2), 12.268 (3)
α, β, γ (°)	91.058 (16), 94.541 (16), 101.648 (15)
V (Å³)	717.3 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.09
Crystal size (mm)	0.40 × 0.20 × 0.15

Data collection
Diffractometer	Stoe IPDS II diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5966, 2811, 1923
R_int	0.055
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.062, 0.132, 1.07
No. of reflections	2811
No. of parameters	199
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.13, −0.16

Computer programs: X-AREA (Stoe & Cie, 2005), X-RED (Stoe & Cie, 2005), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2···N2ⁱ	0.93	2.62	3.439 (3)	147

Symmetry code: (i) −x+3, −y+1, −z+1.

Acknowledgements

We are grateful to the Islamic Azad University, North Tehran Branch, for financial support.

References

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