Literature DB >> 23284476

N-(2-Phen-oxy-phen-yl)pyrazine-2-carboxamide.

Mehri Noroozi Tisseh1, Maryam Kargar Razi, Hamid Reza Khavasi.   

Abstract

In the title compound, C(17)H(13)N(3)O(2), 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.

Entities:  

Year:  2012        PMID： 23284476      PMCID： PMC3515256          DOI： 10.1107/S1600536812041050

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


Related literature

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

Experimental

Crystal data

C17H13N3O2 M = 291.30 Triclinic, 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[F 2 > 2σ(F 2)] = 0.062 wR(F 2) = 0.132 S = 1.07 2811 reflections 199 parameters H-atom parameters constrained Δρmax = 0.13 e Å−3 Δρmin = −0.16 e Å−3 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 ▶). Click here for additional data file. Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812041050/xu5626sup1.cif Click here for additional data file. Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812041050/xu5626Isup2.hkl Click here for additional data file. Supplementary material file. DOI: 10.1107/S1600536812041050/xu5626Isup3.cml Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C17H13N3O2Z = 2
Mr = 291.30F(000) = 304
Triclinic, P1Dx = 1.349 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 5.0913 (10) ÅCell parameters from 5966 reflections
b = 11.769 (2) Åθ = 2.4–26.0°
c = 12.268 (3) ŵ = 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
Stoe IPDS II diffractometer1923 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tubeRint = 0.055
Graphite monochromatorθmax = 26.0°, θmin = 2.4°
rotation method scansh = −6→6
5966 measured reflectionsk = −14→13
2811 independent reflectionsl = −15→15
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.062Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.132H-atom parameters constrained
S = 1.07w = 1/[σ2(Fo2) + (0.0432P)2 + 0.2101P] where P = (Fo2 + 2Fc2)/3
2811 reflections(Δ/σ)max = 0.002
199 parametersΔρmax = 0.13 e Å−3
0 restraintsΔρmin = −0.16 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.
xyzUiso*/Ueq
C11.1804 (5)0.6963 (2)0.4406 (2)0.0618 (7)
H11.24400.76170.48610.074*
C21.2999 (5)0.6018 (2)0.4538 (2)0.0593 (6)
H21.44100.60530.50760.071*
C31.0170 (5)0.50713 (19)0.3160 (2)0.0567 (6)
H30.95520.44190.27000.068*
C40.8953 (4)0.60172 (17)0.30288 (18)0.0462 (5)
C50.6677 (5)0.59753 (18)0.21628 (18)0.0487 (5)
C60.3816 (4)0.72817 (18)0.13538 (17)0.0460 (5)
C70.3225 (5)0.83750 (18)0.15148 (19)0.0494 (5)
C80.1218 (5)0.8733 (2)0.0871 (2)0.0603 (6)
H80.08410.94630.09900.072*
C9−0.0227 (5)0.7994 (2)0.0046 (2)0.0630 (7)
H9−0.15910.8226−0.03890.076*
C100.0351 (5)0.6921 (2)−0.0129 (2)0.0661 (7)
H10−0.06270.6430−0.06860.079*
C110.2372 (5)0.6556 (2)0.05113 (19)0.0578 (6)
H110.27590.58290.03780.069*
C120.4185 (5)1.01105 (19)0.2637 (2)0.0546 (6)
C130.5372 (6)1.1083 (2)0.2146 (3)0.0775 (8)
H130.65701.10420.16200.093*
C140.4776 (9)1.2133 (3)0.2440 (4)0.1099 (15)
H140.55631.28050.21050.132*
C150.3048 (11)1.2189 (4)0.3215 (4)0.130 (2)
H150.26531.28970.34160.156*
C160.1901 (10)1.1207 (4)0.3694 (4)0.1308 (17)
H160.07241.12480.42290.157*
C170.2438 (7)1.0151 (3)0.3406 (3)0.0896 (10)
H170.16220.94780.37320.108*
N10.9782 (4)0.69785 (16)0.36570 (16)0.0559 (5)
N21.2183 (4)0.50575 (17)0.39150 (18)0.0621 (6)
N30.5854 (4)0.69918 (15)0.20727 (15)0.0500 (5)
H3B0.66960.75420.25190.060*
O10.5723 (4)0.50845 (13)0.16236 (15)0.0687 (5)
O20.4781 (4)0.90428 (14)0.23700 (15)0.0714 (6)
U11U22U33U12U13U23
C10.0680 (16)0.0505 (14)0.0679 (16)0.0208 (12)−0.0077 (14)−0.0076 (12)
C20.0609 (15)0.0574 (15)0.0646 (16)0.0240 (12)0.0036 (13)0.0053 (12)
C30.0668 (15)0.0416 (12)0.0660 (16)0.0218 (11)0.0043 (13)−0.0005 (11)
C40.0525 (13)0.0382 (11)0.0518 (13)0.0152 (9)0.0123 (10)0.0034 (9)
C50.0589 (14)0.0368 (11)0.0532 (13)0.0147 (10)0.0100 (11)0.0004 (10)
C60.0503 (12)0.0410 (11)0.0474 (12)0.0116 (9)0.0024 (10)0.0021 (9)
C70.0518 (13)0.0415 (12)0.0539 (13)0.0097 (10)−0.0021 (11)−0.0021 (10)
C80.0623 (15)0.0496 (13)0.0693 (16)0.0186 (12)−0.0103 (13)−0.0005 (12)
C90.0600 (15)0.0663 (16)0.0606 (16)0.0147 (12)−0.0130 (13)0.0036 (13)
C100.0739 (17)0.0612 (16)0.0579 (15)0.0090 (13)−0.0118 (13)−0.0076 (12)
C110.0726 (16)0.0435 (12)0.0562 (14)0.0118 (11)0.0003 (13)−0.0039 (10)
C120.0604 (14)0.0384 (11)0.0650 (15)0.0196 (10)−0.0166 (12)−0.0082 (10)
C130.0769 (19)0.0607 (17)0.089 (2)0.0049 (14)−0.0105 (16)0.0104 (15)
C140.128 (3)0.0379 (16)0.143 (4)0.0001 (18)−0.072 (3)0.0060 (19)
C150.176 (5)0.072 (2)0.146 (4)0.079 (3)−0.094 (4)−0.056 (3)
C160.169 (4)0.132 (4)0.119 (3)0.100 (3)0.009 (3)−0.029 (3)
C170.105 (2)0.075 (2)0.100 (2)0.0375 (18)0.029 (2)0.0095 (17)
N10.0652 (13)0.0419 (10)0.0638 (12)0.0212 (9)−0.0005 (11)−0.0027 (9)
N20.0707 (14)0.0496 (11)0.0725 (14)0.0292 (10)0.0020 (12)0.0035 (10)
N30.0595 (12)0.0378 (10)0.0541 (11)0.0168 (8)−0.0027 (9)−0.0043 (8)
O10.0871 (13)0.0430 (9)0.0761 (12)0.0212 (9)−0.0087 (10)−0.0118 (8)
O20.0782 (12)0.0495 (10)0.0877 (13)0.0331 (9)−0.0328 (10)−0.0241 (9)
C1—N11.328 (3)C9—C101.371 (3)
C1—C21.378 (3)C9—H90.9300
C1—H10.9300C10—C111.387 (3)
C2—N21.327 (3)C10—H100.9300
C2—H20.9300C11—H110.9300
C3—N21.329 (3)C12—C171.353 (4)
C3—C41.385 (3)C12—C131.357 (4)
C3—H30.9300C12—O21.391 (3)
C4—N11.333 (3)C13—C141.379 (5)
C4—C51.501 (3)C13—H130.9300
C5—O11.221 (3)C14—C151.355 (6)
C5—N31.349 (3)C14—H140.9300
C6—C111.390 (3)C15—C161.352 (7)
C6—C71.393 (3)C15—H150.9300
C6—N31.407 (3)C16—C171.371 (5)
C7—C81.380 (3)C16—H160.9300
C7—O21.390 (3)C17—H170.9300
C8—C91.382 (3)N3—H3B0.8600
C8—H80.9300
N1—C1—C2122.8 (2)C11—C10—H10119.5
N1—C1—H1118.6C10—C11—C6119.7 (2)
C2—C1—H1118.6C10—C11—H11120.2
N2—C2—C1121.5 (2)C6—C11—H11120.2
N2—C2—H2119.2C17—C12—C13121.5 (3)
C1—C2—H2119.2C17—C12—O2118.3 (2)
N2—C3—C4122.7 (2)C13—C12—O2120.3 (3)
N2—C3—H3118.6C12—C13—C14119.0 (3)
C4—C3—H3118.6C12—C13—H13120.5
N1—C4—C3121.0 (2)C14—C13—H13120.5
N1—C4—C5118.89 (18)C15—C14—C13120.2 (4)
C3—C4—C5120.1 (2)C15—C14—H14119.9
O1—C5—N3125.8 (2)C13—C14—H14119.9
O1—C5—C4121.02 (19)C16—C15—C14119.5 (3)
N3—C5—C4113.19 (18)C16—C15—H15120.2
C11—C6—C7118.6 (2)C14—C15—H15120.2
C11—C6—N3124.6 (2)C15—C16—C17121.3 (4)
C7—C6—N3116.74 (19)C15—C16—H16119.3
C8—C7—O2124.1 (2)C17—C16—H16119.3
C8—C7—C6121.3 (2)C12—C17—C16118.4 (4)
O2—C7—C6114.61 (19)C12—C17—H17120.8
C7—C8—C9119.4 (2)C16—C17—H17120.8
C7—C8—H8120.3C1—N1—C4116.03 (19)
C9—C8—H8120.3C2—N2—C3115.9 (2)
C10—C9—C8120.0 (2)C5—N3—C6129.29 (19)
C10—C9—H9120.0C5—N3—H3B115.4
C8—C9—H9120.0C6—N3—H3B115.4
C9—C10—C11121.0 (2)C7—O2—C12118.20 (17)
C9—C10—H10119.5
N1—C1—C2—N20.0 (4)C13—C14—C15—C16−0.3 (6)
N2—C3—C4—N10.8 (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—C16178.2 (3)
C3—C4—C5—O16.0 (3)C15—C16—C17—C120.9 (6)
N1—C4—C5—N34.8 (3)C2—C1—N1—C40.1 (4)
C3—C4—C5—N3−174.7 (2)C3—C4—N1—C1−0.4 (3)
C11—C6—C7—C81.2 (4)C5—C4—N1—C1−179.9 (2)
N3—C6—C7—C8−178.5 (2)C1—C2—N2—C30.4 (4)
C11—C6—C7—O2−179.6 (2)C4—C3—N2—C2−0.8 (4)
N3—C6—C7—O20.7 (3)O1—C5—N3—C6−1.3 (4)
O2—C7—C8—C9−179.4 (2)C4—C5—N3—C6179.3 (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—C5174.0 (2)
C8—C9—C10—C110.1 (4)C8—C7—O2—C123.9 (4)
C9—C10—C11—C60.8 (4)C6—C7—O2—C12−175.3 (2)
O2—C12—C13—C14−179.0 (2)C17—C12—O2—C791.4 (3)
C12—C13—C14—C150.6 (5)C13—C12—O2—C7−89.7 (3)
D—H···AD—HH···AD···AD—H···A
C2—H2···N2i0.932.623.439 (3)147
Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A D—HH⋯A D⋯A D—H⋯A
C2—H2⋯N2i 0.932.623.439 (3)147

Symmetry code: (i) .

  3 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.  Patterns of hydrogen bonding in mono- and di-substituted N-arylpyrazinecarboxamides.

Authors:  Solange M S V Wardell; Marcus V N de Souza; Thatyana R A Vasconcelos; Marcelle de L Ferreira; James L Wardell; John N Low; Christopher Glidewell
Journal:  Acta Crystallogr B       Date:  2008-01-17

3.  N-(4-Bromo-phen-yl)pyrazine-2-carbox-amide.

Authors:  Marcelle de Lima Ferreira; Marcus V N de Souza; Solange M S V Wardell; James L Wardell; Edward R T Tiekink
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-10-09
  3 in total

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