Literature DB >> 21582205

2-Methyl-3,5,6-triphenyl-2,3-dihydro-pyrazine.

N Anuradha, A Thiruvalluvar, K Pandiarajan, S Chitra, R J Butcher.   

Abstract

In the title mol-ecule, C(23)H(20)N(2), the heterocyclic ring adopts a screw-boat conformation, with all substituents equatorial. The phenyl ring at position 3 makes dihedral angles of 78.12 (15) and 72.67 (15)°, respectively, with the phenyl rings at positions 5 and 6; the dihedral angle between the phenyl rings at positions 5 and 6 is 67.32 (14)°. A C-H⋯π inter-action is present in the crystal structure.

Entities:  

Year:  2009        PMID： 21582205      PMCID： PMC2968533          DOI： 10.1107/S1600536809005042

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


Related literature

Some 2-alkyl-3,5,6-triphenyl-2,3-dihydro­pyrazines have been reported to exhibit fluorescence in the solid-state, see: Baliah & Pandiarajan (1978 ▶). For the use of dihydro­pyrazines in medicine, in particular with reference to DNA breakage activity, see: Yamaguchi et al. (2003 ▶). For their biological activity, see: Takechi et al. (2004 ▶) and their cyclo­oxygenase inhibitory activity, see: Singh et al. (2004 ▶).

Experimental

Crystal data

C23H20N2 M = 324.41 Triclinic, a = 10.4406 (10) Å b = 10.5753 (7) Å c = 11.0810 (13) Å α = 93.439 (8)° β = 114.161 (10)° γ = 118.343 (9)° V = 931.9 (2) Å3 Z = 2 Cu Kα radiation μ = 0.52 mm−1 T = 295 K 0.41 × 0.36 × 0.28 mm

Data collection

Oxford Diffraction Gemini R diffractometer Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008 ▶) T min = 0.831, T max = 0.885 8513 measured reflections 3852 independent reflections 3195 reflections with I > 2σ(I) R int = 0.045

Refinement

R[F 2 > 2σ(F 2)] = 0.086 wR(F 2) = 0.270 S = 1.09 3852 reflections 227 parameters H-atom parameters constrained Δρmax = 0.47 e Å−3 Δρmin = −0.27 e Å−3 Data collection: CrysAlis CCD (Oxford Diffraction, 2008 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2008 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SIR2004 (Burla et al., 2005 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶); software used to prepare material for publication: PLATON (Spek, 2009 ▶). Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809005042/tk2373sup1.cif Structure factors: contains datablocks I. DOI: 10.1107/S1600536809005042/tk2373Isup2.hkl Additional supplementary materials: crystallographic information; 3D view; checkCIF report
C23H20N2Z = 2
Mr = 324.41F(000) = 344
Triclinic, P1Dx = 1.156 Mg m−3
Hall symbol: -P 1Melting point: 460 K
a = 10.4406 (10) ÅCu Kα radiation, λ = 1.54184 Å
b = 10.5753 (7) ÅCell parameters from 5680 reflections
c = 11.0810 (13) Åθ = 5.2–77.4°
α = 93.439 (8)°µ = 0.52 mm−1
β = 114.161 (10)°T = 295 K
γ = 118.343 (9)°Prism, pale yellow
V = 931.9 (2) Å30.41 × 0.36 × 0.28 mm
Oxford Diffraction Gemini R diffractometer3852 independent reflections
Radiation source: fine-focus sealed tube3195 reflections with I > 2σ(I)
graphiteRint = 0.045
Detector resolution: 10.5081 pixels mm-1θmax = 77.5°, θmin = 5.2°
φ and ω scansh = −13→13
Absorption correction: analytical (CrysAlis RED; Oxford Diffraction, 2008)k = −13→10
Tmin = 0.831, Tmax = 0.885l = −13→13
8513 measured reflections
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.086Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.270H-atom parameters constrained
S = 1.09w = 1/[σ2(Fo2) + (0.1784P)2 + 0.1376P] where P = (Fo2 + 2Fc2)/3
3852 reflections(Δ/σ)max = 0.001
227 parametersΔρmax = 0.47 e Å−3
0 restraintsΔρmin = −0.27 e Å−3
Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles
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
N10.0780 (2)0.1850 (2)−0.0471 (2)0.0633 (6)
N40.39318 (19)0.25469 (17)−0.01087 (17)0.0512 (5)
C20.0900 (3)0.0714 (2)−0.1158 (3)0.0613 (7)
C30.2375 (3)0.1513 (2)−0.1432 (2)0.0551 (6)
C50.3812 (2)0.3247 (2)0.0777 (2)0.0491 (5)
C60.2163 (2)0.3057 (2)0.0441 (2)0.0536 (6)
C21−0.0774 (3)−0.0383 (3)−0.2471 (3)0.0824 (9)
C310.2605 (3)0.0442 (2)−0.2156 (2)0.0587 (6)
C320.3089 (3)−0.0438 (3)−0.1466 (3)0.0712 (8)
C330.3318 (4)−0.1415 (3)−0.2108 (3)0.0873 (10)
C340.3090 (4)−0.1517 (3)−0.3418 (3)0.0930 (10)
C350.2604 (4)−0.0662 (4)−0.4115 (3)0.0901 (10)
C360.2364 (3)0.0324 (3)−0.3491 (3)0.0732 (8)
C510.5327 (2)0.4176 (2)0.2180 (2)0.0498 (6)
C520.5222 (3)0.4188 (3)0.3387 (3)0.0634 (7)
C530.6663 (3)0.4975 (3)0.4688 (3)0.0739 (9)
C540.8218 (3)0.5780 (3)0.4792 (3)0.0725 (8)
C550.8337 (3)0.5780 (3)0.3593 (3)0.0658 (7)
C560.6909 (2)0.4972 (2)0.2294 (2)0.0539 (6)
C610.2079 (3)0.4259 (2)0.1105 (2)0.0537 (6)
C620.0694 (3)0.3844 (3)0.1264 (3)0.0638 (7)
C630.0531 (3)0.4931 (3)0.1805 (3)0.0762 (10)
C640.1712 (4)0.6439 (3)0.2153 (3)0.0806 (10)
C650.3098 (3)0.6872 (3)0.1991 (3)0.0750 (9)
C660.3283 (3)0.5782 (3)0.1468 (3)0.0630 (7)
H20.112720.01451−0.052490.0736*
H30.216960.21204−0.202810.0661*
H21A−0.16525−0.07906−0.224110.1236*
H21B−0.07434−0.11930−0.287020.1236*
H21C−0.098240.01403−0.313080.1236*
H320.32603−0.03712−0.056630.0854*
H330.36313−0.20078−0.163770.1046*
H340.32629−0.21646−0.383720.1115*
H350.24329−0.07406−0.501590.1078*
H360.204070.09047−0.397210.0879*
H520.417480.366260.332460.0761*
H530.657830.495900.549110.0886*
H540.918240.632050.566370.0869*
H550.938640.632790.366180.0790*
H560.700220.495940.149490.0647*
H62−0.012990.282420.100220.0765*
H63−0.038350.464140.193380.0914*
H640.158480.716990.249760.0967*
H650.390290.789410.223420.0900*
H660.421240.607290.136140.0757*
U11U22U33U12U13U23
N10.0477 (9)0.0567 (10)0.0707 (12)0.0264 (8)0.0224 (8)0.0037 (8)
N40.0459 (8)0.0449 (8)0.0534 (9)0.0233 (7)0.0207 (7)0.0036 (6)
C20.0515 (11)0.0536 (11)0.0620 (12)0.0248 (9)0.0216 (9)0.0032 (9)
C30.0529 (10)0.0477 (10)0.0524 (11)0.0283 (8)0.0171 (9)0.0030 (8)
C50.0431 (9)0.0440 (9)0.0542 (10)0.0234 (7)0.0211 (8)0.0071 (7)
C60.0453 (9)0.0514 (10)0.0587 (11)0.0266 (8)0.0229 (8)0.0072 (8)
C210.0577 (13)0.0709 (15)0.0799 (17)0.0244 (11)0.0199 (12)−0.0044 (12)
C310.0504 (10)0.0485 (10)0.0551 (11)0.0260 (8)0.0127 (8)−0.0046 (8)
C320.0698 (14)0.0611 (12)0.0694 (14)0.0411 (11)0.0196 (11)0.0067 (10)
C330.0798 (17)0.0651 (14)0.092 (2)0.0482 (13)0.0160 (14)−0.0018 (13)
C340.0795 (17)0.0765 (17)0.093 (2)0.0488 (14)0.0179 (15)−0.0205 (15)
C350.0881 (19)0.094 (2)0.0633 (15)0.0484 (16)0.0244 (14)−0.0110 (14)
C360.0730 (14)0.0702 (14)0.0593 (13)0.0419 (12)0.0185 (11)0.0014 (10)
C510.0462 (9)0.0463 (9)0.0546 (11)0.0275 (8)0.0221 (8)0.0048 (7)
C520.0570 (11)0.0717 (13)0.0623 (12)0.0368 (10)0.0303 (10)0.0081 (10)
C530.0755 (15)0.0947 (17)0.0516 (12)0.0510 (14)0.0290 (11)0.0056 (11)
C540.0594 (12)0.0782 (15)0.0551 (12)0.0384 (11)0.0115 (10)−0.0064 (10)
C550.0464 (10)0.0626 (12)0.0670 (13)0.0249 (9)0.0197 (10)−0.0003 (10)
C560.0481 (10)0.0512 (10)0.0552 (11)0.0256 (8)0.0233 (8)0.0057 (8)
C610.0484 (10)0.0577 (10)0.0552 (11)0.0330 (9)0.0224 (8)0.0101 (8)
C620.0544 (11)0.0722 (13)0.0677 (13)0.0380 (10)0.0296 (10)0.0164 (10)
C630.0703 (14)0.1005 (19)0.0767 (16)0.0583 (15)0.0393 (12)0.0184 (14)
C640.0844 (17)0.0880 (17)0.0815 (17)0.0620 (15)0.0363 (14)0.0059 (13)
C650.0728 (14)0.0619 (13)0.0844 (17)0.0404 (12)0.0326 (13)0.0053 (11)
C660.0554 (11)0.0586 (12)0.0741 (14)0.0331 (10)0.0309 (10)0.0084 (10)
N1—C21.466 (4)C62—C631.377 (5)
N1—C61.279 (3)C63—C641.372 (4)
N4—C31.469 (3)C64—C651.389 (6)
N4—C51.276 (3)C65—C661.387 (5)
C2—C31.535 (4)C2—H20.9800
C2—C211.519 (4)C3—H30.9800
C3—C311.514 (4)C21—H21A0.9600
C5—C61.510 (3)C21—H21B0.9600
C5—C511.487 (3)C21—H21C0.9600
C6—C611.487 (3)C32—H320.9300
C31—C321.386 (4)C33—H330.9300
C31—C361.382 (4)C34—H340.9300
C32—C331.384 (5)C35—H350.9300
C33—C341.360 (4)C36—H360.9300
C34—C351.368 (5)C52—H520.9300
C35—C361.390 (5)C53—H530.9300
C51—C521.386 (4)C54—H540.9300
C51—C561.396 (3)C55—H550.9300
C52—C531.388 (4)C56—H560.9300
C53—C541.377 (5)C62—H620.9300
C54—C551.384 (4)C63—H630.9300
C55—C561.382 (4)C64—H640.9300
C61—C621.389 (5)C65—H650.9300
C61—C661.386 (4)C66—H660.9300
N1···N42.848 (3)H2···C52.8400
N4···N12.848 (3)H2···C322.9200
N1···H622.5700H2···H322.5500
N1···H2i2.7800H2···N1i2.7800
N4···H322.7800H3···C62.8600
N4···H562.6400H3···H21C2.5600
N4···H33ii2.8300H3···H362.3600
N4···H66iii2.7500H3···C55iii3.0100
C32···C32ii3.585 (5)H3···C56iii2.8300
C51···C663.207 (4)H21B···C312.7700
C52···C663.407 (5)H21C···H32.5600
C52···C613.261 (4)H21C···C35v3.0600
C61···C523.261 (4)H21C···H35v2.3300
C62···C64iv3.479 (4)H32···N42.7800
C64···C62iv3.479 (4)H32···C23.0500
C66···C513.207 (4)H32···H22.5500
C66···C523.407 (5)H32···C33ii3.0600
C2···H323.0500H33···N4ii2.8300
C5···H22.8400H33···C51ii3.0900
C5···H662.8100H33···C56ii2.9000
C6···H522.8300H35···H21Cv2.3300
C6···H32.8600H36···H32.3600
C31···H21B2.7700H52···C62.8300
C32···H22.9200H52···C612.8900
C33···H32ii3.0600H52···H53vi2.4800
C35···H65iii3.0200H53···C52vi3.0500
C35···H21Cv3.0600H53···H52vi2.4800
C36···H65iii2.9900H56···N42.6400
C51···H662.7900H62···N12.5700
C51···H33ii3.0900H65···C35iii3.0200
C52···H53vi3.0500H65···C36iii2.9900
C55···H3iii3.0100H66···C52.8100
C56···H33ii2.9000H66···C512.7900
C56···H3iii2.8300H66···N4iii2.7500
C61···H522.8900
C2—N1—C6116.8 (2)C21—C2—H2108.00
C3—N4—C5116.3 (2)N4—C3—H3108.00
N1—C2—C3109.45 (18)C2—C3—H3108.00
N1—C2—C21109.0 (3)C31—C3—H3108.00
C3—C2—C21113.5 (2)C2—C21—H21A109.00
N4—C3—C2109.53 (19)C2—C21—H21B109.00
N4—C3—C31109.3 (2)C2—C21—H21C109.00
C2—C3—C31113.97 (18)H21A—C21—H21B109.00
N4—C5—C6121.10 (19)H21A—C21—H21C110.00
N4—C5—C51117.5 (2)H21B—C21—H21C109.00
C6—C5—C51121.34 (19)C31—C32—H32120.00
N1—C6—C5120.0 (2)C33—C32—H32120.00
N1—C6—C61117.9 (2)C32—C33—H33120.00
C5—C6—C61122.14 (19)C34—C33—H33120.00
C3—C31—C32119.6 (2)C33—C34—H34120.00
C3—C31—C36121.8 (2)C35—C34—H34120.00
C32—C31—C36118.5 (3)C34—C35—H35120.00
C31—C32—C33120.4 (3)C36—C35—H35120.00
C32—C33—C34120.7 (3)C31—C36—H36120.00
C33—C34—C35119.6 (4)C35—C36—H36120.00
C34—C35—C36120.7 (3)C51—C52—H52120.00
C31—C36—C35120.1 (3)C53—C52—H52120.00
C5—C51—C52121.7 (2)C52—C53—H53120.00
C5—C51—C56119.25 (19)C54—C53—H53120.00
C52—C51—C56118.9 (2)C53—C54—H54120.00
C51—C52—C53120.7 (3)C55—C54—H54120.00
C52—C53—C54120.1 (3)C54—C55—H55120.00
C53—C54—C55119.7 (3)C56—C55—H55120.00
C54—C55—C56120.5 (3)C51—C56—H56120.00
C51—C56—C55120.1 (2)C55—C56—H56120.00
C6—C61—C62119.0 (2)C61—C62—H62120.00
C6—C61—C66121.5 (3)C63—C62—H62120.00
C62—C61—C66119.4 (3)C62—C63—H63120.00
C61—C62—C63120.5 (3)C64—C63—H63120.00
C62—C63—C64120.2 (4)C63—C64—H64120.00
C63—C64—C65119.9 (3)C65—C64—H64120.00
C64—C65—C66120.1 (3)C64—C65—H65120.00
C61—C66—C65119.8 (3)C66—C65—H65120.00
N1—C2—H2108.00C61—C66—H66120.00
C3—C2—H2108.00C65—C66—H66120.00
C6—N1—C2—C3−38.6 (3)C5—C6—C61—C62−151.9 (2)
C6—N1—C2—C21−163.2 (2)C5—C6—C61—C6633.1 (3)
C2—N1—C6—C5−0.8 (3)C3—C31—C32—C33−179.5 (3)
C2—N1—C6—C61177.16 (19)C36—C31—C32—C33−0.2 (5)
C5—N4—C3—C2−37.2 (3)C3—C31—C36—C35179.4 (3)
C5—N4—C3—C31−162.71 (18)C32—C31—C36—C350.1 (5)
C3—N4—C5—C6−2.4 (3)C31—C32—C33—C340.7 (5)
C3—N4—C5—C51173.76 (17)C32—C33—C34—C35−1.0 (6)
N1—C2—C3—N457.9 (3)C33—C34—C35—C360.9 (6)
N1—C2—C3—C31−179.37 (19)C34—C35—C36—C31−0.4 (6)
C21—C2—C3—N4179.9 (2)C5—C51—C52—C53175.2 (3)
C21—C2—C3—C31−57.3 (3)C56—C51—C52—C53−0.1 (4)
N4—C3—C31—C3256.1 (3)C5—C51—C56—C55−176.7 (2)
N4—C3—C31—C36−123.2 (3)C52—C51—C56—C55−1.3 (4)
C2—C3—C31—C32−66.8 (3)C51—C52—C53—C541.3 (5)
C2—C3—C31—C36113.9 (3)C52—C53—C54—C55−1.0 (5)
N4—C5—C6—N125.0 (3)C53—C54—C55—C56−0.4 (5)
N4—C5—C6—C61−152.88 (19)C54—C55—C56—C511.6 (4)
C51—C5—C6—N1−151.0 (2)C6—C61—C62—C63−176.5 (2)
C51—C5—C6—C6131.1 (3)C66—C61—C62—C63−1.4 (4)
N4—C5—C51—C52−138.4 (2)C6—C61—C66—C65175.3 (2)
N4—C5—C51—C5636.9 (3)C62—C61—C66—C650.3 (4)
C6—C5—C51—C5237.7 (3)C61—C62—C63—C642.0 (4)
C6—C5—C51—C56−147.0 (2)C62—C63—C64—C65−1.6 (4)
N1—C6—C61—C6230.2 (3)C63—C64—C65—C660.5 (4)
N1—C6—C61—C66−144.8 (2)C64—C65—C66—C610.1 (4)
D—H···AD—HH···AD···AD—H···A
C65—H65···Cg(C31–C36)iii0.932.973.834 (3)156
Table 1

Hydrogen-bond geometry (Å, °)

Cg is the centroid of the C31–C36 ring.

D—H⋯AD—HH⋯AD⋯AD—H⋯A
C65—H65⋯Cgi0.932.973.834 (3)156

Symmetry code: (i) .

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