organic compounds
2-Methyl-3-(4-methylphenyl)-5,6-diphenyl-2,3-dihydropyrazine
aPostgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India, bDepartment of Chemistry, KSR College of Engineering, KSR Kalvi Nagar, Tiruchengode 637 215, Tamilnadu, India, cDepartment of Chemistry, Government Arts College, C. Mutlur 608 102, Chidambaram, Tamilnadu, India, and dDepartment of Chemistry, Howard University, 525 College Street NW, Washington, DC 20059, USA
*Correspondence e-mail: thiruvalluvar.a@gmail.com
In the title molecule, C24H22N2, four atoms (N—C—C—N) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions; the site-occupancy factor of the major component is 0.713 (6). The major disorder component of the heterocyclic ring adopts a half-chair conformation, with all substituents equatorial. The benzene ring adjacent to the methyl group forms dihedral angles of 79.68 (11) and 80.92 (11)° with the phenyl rings; the dihedral angle between adjacent phenyl rings is 59.10 (11)°. The features three C—H⋯π interactions.
Related literature
For the biological properties of dihydropyrazines and for closely related crystal structures, see: Anuradha et al. (2009, 2011).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Agilent, 2012); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).
Supporting information
10.1107/S1600536812041438/hg5255sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S1600536812041438/hg5255Isup2.hkl
Supporting information file. DOI: 10.1107/S1600536812041438/hg5255Isup3.cdx
Supporting information file. DOI: 10.1107/S1600536812041438/hg5255Isup4.cml
To a homogeneous solution of benzil (1.05 g, 0.005 mol) and 1-methyl-2-(4'-methylphenyl)-ethanediaminedihydrochloride (1.29 g, 0.005 mol) in ethanol (20 ml), sodium acetate trihydrate (2.04 g, 0.015 mol) was added. The precipitated sodium chloride was filtered off and the filtrate was refluxed for 2 h. On completion of the reaction, as indicated by TLC, the reaction mixture was poured into crushed ice and the resulting solid was filtered and purified by
on silica gel. Elution with benzene-petroleum ether (4:1 v/v) at 333–353 K gave the pure product. Yield 1.60 g (72%). The pure product was recrystallized in ethyl acetate, to obtain crystals suitable for X-ray diffraction studies.The H atoms were positioned geometrically and allowed to ride on their parent atoms, with C—H = 0.95–1.00 Å, and with Uiso(H) = 1.2–1.5Ueq(C). Four atoms (N2/C3/C5/N1) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions. The anisotropic displacement parameters of equivalent atoms were constrained to be equal; the site occupancy factors refined to 0.713 (6) and 0.287 (6). A damping factor (damp 100 in the final
cycles) was applied to avoid large displacements of the disordered hydrogen atoms.Data collection: CrysAlis PRO (Agilent, 2012); cell
CrysAlis PRO (Agilent, 2012); data reduction: CrysAlis PRO (Agilent, 2012); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); 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).C24H22N2 | F(000) = 720 |
Mr = 338.44 | Dx = 1.182 Mg m−3 |
Monoclinic, P21/c | Melting point: 450 K |
Hall symbol: -P 2ybc | Cu Kα radiation, λ = 1.54184 Å |
a = 8.1986 (5) Å | Cell parameters from 3179 reflections |
b = 11.8211 (6) Å | θ = 3.7–75.3° |
c = 19.6686 (7) Å | µ = 0.53 mm−1 |
β = 93.638 (4)° | T = 123 K |
V = 1902.38 (17) Å3 | Prism, colourless |
Z = 4 | 0.39 × 0.21 × 0.17 mm |
Agilent Xcalibur Ruby Gemini diffractometer | 3892 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 3044 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.028 |
Detector resolution: 10.5081 pixels mm-1 | θmax = 75.5°, θmin = 4.4° |
ω scans | h = −10→9 |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | k = −13→14 |
Tmin = 0.830, Tmax = 1.000 | l = −24→21 |
12585 measured reflections |
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)] = 0.069 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.07 | w = 1/[σ2(Fo2) + (0.1119P)2 + 0.6381P] where P = (Fo2 + 2Fc2)/3 |
3892 reflections | (Δ/σ)max = 0.001 |
254 parameters | Δρmax = 0.71 e Å−3 |
68 restraints | Δρmin = −0.35 e Å−3 |
C24H22N2 | V = 1902.38 (17) Å3 |
Mr = 338.44 | Z = 4 |
Monoclinic, P21/c | Cu Kα radiation |
a = 8.1986 (5) Å | µ = 0.53 mm−1 |
b = 11.8211 (6) Å | T = 123 K |
c = 19.6686 (7) Å | 0.39 × 0.21 × 0.17 mm |
β = 93.638 (4)° |
Agilent Xcalibur Ruby Gemini diffractometer | 3892 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2012) | 3044 reflections with I > 2σ(I) |
Tmin = 0.830, Tmax = 1.000 | Rint = 0.028 |
12585 measured reflections |
R[F2 > 2σ(F2)] = 0.069 | 68 restraints |
wR(F2) = 0.214 | H-atom parameters constrained |
S = 1.07 | Δρmax = 0.71 e Å−3 |
3892 reflections | Δρmin = −0.35 e Å−3 |
254 parameters |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
N1A | 0.2620 (9) | 0.8818 (4) | 0.1306 (3) | 0.0675 (11) | 0.713 (6) |
N2A | 0.2421 (13) | 0.9429 (5) | −0.0086 (3) | 0.0781 (11) | 0.713 (6) |
C1 | 0.2458 (3) | 0.80641 (19) | 0.08145 (10) | 0.0556 (7) | |
C2 | 0.2522 (3) | 0.8383 (2) | 0.00937 (11) | 0.0604 (7) | |
C3A | 0.2008 (6) | 1.0239 (3) | 0.04467 (17) | 0.0605 (12) | 0.713 (6) |
C4A | 0.2286 (11) | 1.1422 (5) | 0.0181 (4) | 0.0792 (15) | 0.713 (6) |
C5A | 0.3136 (7) | 0.9952 (4) | 0.1078 (2) | 0.0682 (15) | 0.713 (6) |
C6 | 0.2095 (3) | 0.68882 (18) | 0.10250 (10) | 0.0518 (6) | |
C7 | 0.2969 (3) | 0.64263 (19) | 0.15892 (11) | 0.0548 (6) | |
C8 | 0.2641 (3) | 0.53339 (19) | 0.18009 (12) | 0.0584 (7) | |
C9 | 0.1433 (3) | 0.47028 (19) | 0.14630 (11) | 0.0590 (7) | |
C10 | 0.0534 (3) | 0.5165 (2) | 0.09150 (11) | 0.0590 (7) | |
C11 | 0.0877 (3) | 0.62512 (19) | 0.06909 (10) | 0.0553 (7) | |
C12 | 0.2806 (3) | 0.75362 (19) | −0.04483 (11) | 0.0566 (7) | |
C13 | 0.3907 (3) | 0.6650 (2) | −0.03313 (11) | 0.0601 (7) | |
C14 | 0.4185 (3) | 0.5879 (2) | −0.08442 (13) | 0.0666 (8) | |
C15 | 0.3345 (3) | 0.5981 (2) | −0.14751 (12) | 0.0664 (8) | |
C16 | 0.2262 (3) | 0.6859 (2) | −0.16006 (12) | 0.0649 (8) | |
C17 | 0.1998 (3) | 0.7640 (2) | −0.10907 (11) | 0.0617 (7) | |
C18 | 0.2782 (4) | 1.0771 (2) | 0.16632 (11) | 0.0667 (8) | |
C19 | 0.3912 (3) | 1.16373 (19) | 0.17894 (12) | 0.0636 (8) | |
C20 | 0.3719 (3) | 1.24072 (18) | 0.23056 (11) | 0.0562 (7) | |
C21 | 0.2402 (3) | 1.23338 (19) | 0.27160 (10) | 0.0548 (7) | |
C22 | 0.1289 (3) | 1.1477 (2) | 0.25858 (12) | 0.0644 (8) | |
C23 | 0.1480 (3) | 1.0702 (2) | 0.20701 (12) | 0.0685 (8) | |
C24 | 0.2223 (4) | 1.3153 (2) | 0.32921 (13) | 0.0775 (10) | |
N1B | 0.291 (3) | 0.8782 (12) | 0.1267 (9) | 0.0675 (11) | 0.287 (6) |
N2B | 0.220 (4) | 0.9433 (14) | −0.0092 (8) | 0.0781 (11) | 0.287 (6) |
C3B | 0.2792 (15) | 1.0317 (8) | 0.0396 (4) | 0.0605 (12) | 0.287 (6) |
C4B | 0.195 (3) | 1.1406 (13) | 0.0178 (12) | 0.0792 (15) | 0.287 (6) |
C5B | 0.2419 (19) | 0.9953 (10) | 0.1111 (5) | 0.0682 (15) | 0.287 (6) |
H7A | 0.37917 | 0.68605 | 0.18298 | 0.0657* | |
H8A | 0.32533 | 0.50200 | 0.21814 | 0.0701* | |
H1A | 0.08386 | 1.01444 | 0.05527 | 0.0724* | 0.713 (6) |
H2A | 0.15954 | 1.15427 | −0.02381 | 0.1186* | 0.713 (6) |
H3A | 0.20059 | 1.19772 | 0.05242 | 0.1186* | 0.713 (6) |
H4A | 0.34371 | 1.15099 | 0.00839 | 0.1186* | 0.713 (6) |
H5A | 0.43148 | 0.99642 | 0.09751 | 0.0819* | 0.713 (6) |
H15A | 0.35169 | 0.54430 | −0.18224 | 0.0797* | |
H16A | 0.16954 | 0.69305 | −0.20351 | 0.0778* | |
H17A | 0.12614 | 0.82504 | −0.11808 | 0.0740* | |
H19A | 0.48250 | 1.16990 | 0.15174 | 0.0763* | |
H20A | 0.44973 | 1.29963 | 0.23819 | 0.0675* | |
H22A | 0.03708 | 1.14176 | 0.28552 | 0.0772* | |
H23A | 0.07014 | 1.01130 | 0.19956 | 0.0822* | |
H24A | 0.10614 | 1.32498 | 0.33688 | 0.1160* | |
H24B | 0.27968 | 1.28581 | 0.37071 | 0.1160* | |
H24C | 0.26928 | 1.38848 | 0.31757 | 0.1160* | |
H9A | 0.12204 | 0.39527 | 0.16064 | 0.0708* | |
H10A | −0.03236 | 0.47404 | 0.06897 | 0.0708* | |
H11A | 0.02715 | 0.65567 | 0.03060 | 0.0663* | |
H13A | 0.44729 | 0.65724 | 0.01028 | 0.0720* | |
H14A | 0.49501 | 0.52833 | −0.07626 | 0.0798* | |
H6B | 0.39999 | 1.04078 | 0.03728 | 0.0724* | 0.287 (6) |
H7B | 0.12757 | 1.12787 | −0.02437 | 0.1186* | 0.287 (6) |
H8B | 0.12589 | 1.16604 | 0.05365 | 0.1186* | 0.287 (6) |
H9B | 0.27751 | 1.19846 | 0.01009 | 0.1186* | 0.287 (6) |
H10B | 0.11982 | 0.99121 | 0.10842 | 0.0819* | 0.287 (6) |
U11 | U22 | U33 | U12 | U13 | U23 | |
N1A | 0.109 (3) | 0.0531 (11) | 0.0414 (12) | −0.0068 (14) | 0.0131 (15) | 0.0041 (9) |
N2A | 0.130 (3) | 0.0623 (12) | 0.0421 (10) | 0.0090 (15) | 0.0068 (13) | 0.0061 (9) |
C1 | 0.0714 (13) | 0.0551 (11) | 0.0412 (10) | 0.0034 (10) | 0.0114 (9) | 0.0037 (8) |
C2 | 0.0792 (14) | 0.0596 (12) | 0.0427 (10) | 0.0019 (11) | 0.0074 (10) | 0.0046 (9) |
C3A | 0.079 (3) | 0.0616 (15) | 0.0408 (12) | −0.006 (2) | 0.0041 (17) | 0.0034 (11) |
C4A | 0.107 (4) | 0.0719 (16) | 0.0580 (14) | 0.006 (2) | 0.001 (2) | 0.0083 (12) |
C5A | 0.109 (4) | 0.0531 (13) | 0.0435 (13) | 0.002 (2) | 0.012 (2) | 0.0063 (10) |
C6 | 0.0628 (12) | 0.0521 (11) | 0.0420 (10) | 0.0023 (9) | 0.0151 (8) | 0.0009 (8) |
C7 | 0.0601 (11) | 0.0573 (12) | 0.0477 (10) | −0.0011 (10) | 0.0090 (9) | 0.0031 (9) |
C8 | 0.0653 (13) | 0.0580 (12) | 0.0532 (12) | 0.0075 (10) | 0.0149 (10) | 0.0097 (10) |
C9 | 0.0693 (13) | 0.0523 (11) | 0.0581 (12) | −0.0006 (10) | 0.0247 (10) | 0.0006 (9) |
C10 | 0.0647 (12) | 0.0634 (13) | 0.0508 (11) | −0.0094 (10) | 0.0192 (10) | −0.0084 (10) |
C11 | 0.0634 (12) | 0.0632 (12) | 0.0403 (10) | 0.0030 (10) | 0.0112 (9) | −0.0014 (9) |
C12 | 0.0698 (13) | 0.0591 (12) | 0.0424 (10) | −0.0054 (10) | 0.0150 (9) | 0.0026 (9) |
C13 | 0.0699 (13) | 0.0636 (13) | 0.0483 (11) | −0.0033 (11) | 0.0167 (10) | 0.0029 (10) |
C14 | 0.0758 (14) | 0.0649 (14) | 0.0622 (13) | −0.0046 (12) | 0.0299 (11) | −0.0002 (11) |
C15 | 0.0770 (14) | 0.0694 (14) | 0.0561 (13) | −0.0192 (12) | 0.0293 (11) | −0.0120 (10) |
C16 | 0.0688 (13) | 0.0823 (16) | 0.0451 (11) | −0.0186 (12) | 0.0166 (10) | −0.0057 (10) |
C17 | 0.0686 (13) | 0.0726 (14) | 0.0451 (11) | −0.0058 (11) | 0.0132 (10) | 0.0018 (10) |
C18 | 0.111 (2) | 0.0513 (12) | 0.0378 (10) | −0.0028 (12) | 0.0060 (11) | 0.0081 (9) |
C19 | 0.0850 (15) | 0.0542 (12) | 0.0542 (12) | 0.0065 (11) | 0.0249 (11) | 0.0092 (9) |
C20 | 0.0645 (12) | 0.0511 (11) | 0.0539 (11) | 0.0012 (10) | 0.0101 (9) | 0.0056 (9) |
C21 | 0.0672 (12) | 0.0562 (12) | 0.0416 (10) | 0.0042 (10) | 0.0093 (9) | 0.0067 (9) |
C22 | 0.0682 (13) | 0.0724 (15) | 0.0539 (12) | −0.0063 (12) | 0.0141 (10) | 0.0115 (11) |
C23 | 0.0898 (17) | 0.0626 (13) | 0.0522 (12) | −0.0185 (12) | −0.0031 (12) | 0.0072 (10) |
C24 | 0.104 (2) | 0.0758 (16) | 0.0554 (13) | 0.0010 (15) | 0.0260 (13) | −0.0034 (12) |
N1B | 0.109 (3) | 0.0531 (11) | 0.0414 (12) | −0.0068 (14) | 0.0131 (15) | 0.0041 (9) |
N2B | 0.130 (3) | 0.0623 (12) | 0.0421 (10) | 0.0090 (15) | 0.0068 (13) | 0.0061 (9) |
C3B | 0.079 (3) | 0.0616 (15) | 0.0408 (12) | −0.006 (2) | 0.0041 (17) | 0.0034 (11) |
C4B | 0.107 (4) | 0.0719 (16) | 0.0580 (14) | 0.006 (2) | 0.001 (2) | 0.0083 (12) |
C5B | 0.109 (4) | 0.0531 (13) | 0.0435 (13) | 0.002 (2) | 0.012 (2) | 0.0063 (10) |
N1A—C1 | 1.315 (6) | C20—C21 | 1.391 (3) |
N1A—C5A | 1.484 (7) | C21—C22 | 1.376 (3) |
N1B—C5B | 1.47 (2) | C21—C24 | 1.505 (3) |
N1B—C1 | 1.268 (17) | C22—C23 | 1.383 (3) |
N2A—C3A | 1.475 (7) | C3A—H1A | 1.0000 |
N2A—C2 | 1.287 (6) | C3B—H6B | 1.0000 |
N2B—C2 | 1.316 (17) | C4A—H3A | 0.9800 |
N2B—C3B | 1.48 (2) | C4A—H4A | 0.9800 |
C1—C6 | 1.486 (3) | C4A—H2A | 0.9800 |
C1—C2 | 1.471 (3) | C4B—H7B | 0.9800 |
C2—C12 | 1.491 (3) | C4B—H8B | 0.9800 |
C3A—C4A | 1.515 (7) | C4B—H9B | 0.9800 |
C3A—C5A | 1.538 (6) | C5A—H5A | 1.0000 |
C3B—C4B | 1.51 (2) | C5B—H10B | 1.0000 |
C3B—C5B | 1.520 (13) | C7—H7A | 0.9500 |
C5A—C18 | 1.546 (5) | C8—H8A | 0.9500 |
C5B—C18 | 1.470 (11) | C9—H9A | 0.9500 |
C6—C7 | 1.394 (3) | C10—H10A | 0.9500 |
C6—C11 | 1.383 (3) | C11—H11A | 0.9500 |
C7—C8 | 1.388 (3) | C13—H13A | 0.9500 |
C8—C9 | 1.377 (3) | C14—H14A | 0.9500 |
C9—C10 | 1.379 (3) | C15—H15A | 0.9500 |
C10—C11 | 1.392 (3) | C16—H16A | 0.9500 |
C12—C13 | 1.392 (3) | C17—H17A | 0.9500 |
C12—C17 | 1.394 (3) | C19—H19A | 0.9500 |
C13—C14 | 1.389 (3) | C20—H20A | 0.9500 |
C14—C15 | 1.386 (3) | C22—H22A | 0.9500 |
C15—C16 | 1.378 (3) | C23—H23A | 0.9500 |
C16—C17 | 1.390 (3) | C24—H24B | 0.9800 |
C18—C19 | 1.393 (4) | C24—H24C | 0.9800 |
C18—C23 | 1.377 (4) | C24—H24A | 0.9800 |
C19—C20 | 1.380 (3) | ||
C1—N1A—C5A | 114.1 (4) | C5A—C3A—H1A | 110.00 |
C1—N1B—C5B | 114.9 (14) | C5B—C3B—H6B | 109.00 |
C2—N2A—C3A | 116.3 (5) | N2B—C3B—H6B | 109.00 |
C2—N2B—C3B | 115.7 (14) | C4B—C3B—H6B | 109.00 |
N1A—C1—C6 | 116.2 (3) | C3A—C4A—H3A | 110.00 |
C2—C1—C6 | 121.89 (19) | H2A—C4A—H4A | 109.00 |
N1B—C1—C6 | 119.0 (7) | C3A—C4A—H4A | 109.00 |
N1B—C1—C2 | 118.6 (8) | H2A—C4A—H3A | 110.00 |
N1A—C1—C2 | 121.8 (3) | C3A—C4A—H2A | 109.00 |
N2A—C2—C1 | 120.3 (3) | H3A—C4A—H4A | 110.00 |
N2B—C2—C1 | 119.4 (8) | C3B—C4B—H7B | 109.00 |
N2B—C2—C12 | 118.2 (7) | C3B—C4B—H9B | 109.00 |
N2A—C2—C12 | 117.3 (3) | H7B—C4B—H8B | 110.00 |
C1—C2—C12 | 122.3 (2) | C3B—C4B—H8B | 109.00 |
C4A—C3A—C5A | 112.7 (4) | H8B—C4B—H9B | 109.00 |
N2A—C3A—C4A | 107.9 (4) | H7B—C4B—H9B | 110.00 |
N2A—C3A—C5A | 106.1 (4) | C3A—C5A—H5A | 112.00 |
N2B—C3B—C4B | 107.0 (14) | C18—C5A—H5A | 112.00 |
N2B—C3B—C5B | 108.9 (11) | N1A—C5A—H5A | 112.00 |
C4B—C3B—C5B | 112.9 (12) | C18—C5B—H10B | 103.00 |
C3A—C5A—C18 | 109.4 (4) | C3B—C5B—H10B | 103.00 |
N1A—C5A—C3A | 106.0 (4) | N1B—C5B—H10B | 103.00 |
N1A—C5A—C18 | 105.7 (4) | C8—C7—H7A | 120.00 |
N1B—C5B—C18 | 115.2 (10) | C6—C7—H7A | 120.00 |
C3B—C5B—C18 | 117.0 (9) | C7—C8—H8A | 120.00 |
N1B—C5B—C3B | 113.1 (11) | C9—C8—H8A | 120.00 |
C7—C6—C11 | 119.0 (2) | C10—C9—H9A | 120.00 |
C1—C6—C7 | 119.1 (2) | C8—C9—H9A | 120.00 |
C1—C6—C11 | 121.89 (19) | C9—C10—H10A | 120.00 |
C6—C7—C8 | 120.2 (2) | C11—C10—H10A | 120.00 |
C7—C8—C9 | 120.4 (2) | C6—C11—H11A | 120.00 |
C8—C9—C10 | 119.7 (2) | C10—C11—H11A | 120.00 |
C9—C10—C11 | 120.3 (2) | C12—C13—H13A | 120.00 |
C6—C11—C10 | 120.4 (2) | C14—C13—H13A | 120.00 |
C2—C12—C13 | 121.1 (2) | C15—C14—H14A | 120.00 |
C2—C12—C17 | 120.1 (2) | C13—C14—H14A | 120.00 |
C13—C12—C17 | 118.8 (2) | C14—C15—H15A | 120.00 |
C12—C13—C14 | 120.5 (2) | C16—C15—H15A | 120.00 |
C13—C14—C15 | 119.9 (2) | C17—C16—H16A | 120.00 |
C14—C15—C16 | 120.3 (2) | C15—C16—H16A | 120.00 |
C15—C16—C17 | 119.9 (2) | C12—C17—H17A | 120.00 |
C12—C17—C16 | 120.6 (2) | C16—C17—H17A | 120.00 |
C5A—C18—C19 | 116.1 (3) | C18—C19—H19A | 120.00 |
C5A—C18—C23 | 125.8 (3) | C20—C19—H19A | 120.00 |
C19—C18—C23 | 118.1 (2) | C21—C20—H20A | 119.00 |
C5B—C18—C19 | 135.8 (6) | C19—C20—H20A | 119.00 |
C5B—C18—C23 | 105.2 (6) | C21—C22—H22A | 119.00 |
C18—C19—C20 | 120.7 (2) | C23—C22—H22A | 119.00 |
C19—C20—C21 | 121.0 (2) | C18—C23—H23A | 119.00 |
C20—C21—C22 | 117.9 (2) | C22—C23—H23A | 120.00 |
C20—C21—C24 | 120.9 (2) | H24B—C24—H24C | 109.00 |
C22—C21—C24 | 121.2 (2) | H24A—C24—H24B | 109.00 |
C21—C22—C23 | 121.3 (2) | H24A—C24—H24C | 109.00 |
C18—C23—C22 | 121.0 (2) | C21—C24—H24A | 109.00 |
N2A—C3A—H1A | 110.00 | C21—C24—H24B | 109.00 |
C4A—C3A—H1A | 110.00 | C21—C24—H24C | 109.00 |
C5A—N1A—C1—C2 | −9.5 (7) | C3A—C5A—C18—C23 | 77.9 (4) |
C5A—N1A—C1—C6 | 174.5 (4) | C1—C6—C7—C8 | 179.3 (2) |
C1—N1A—C5A—C18 | 164.4 (5) | C11—C6—C7—C8 | 1.4 (3) |
C1—N1A—C5A—C3A | 48.4 (7) | C1—C6—C11—C10 | −177.9 (2) |
C3A—N2A—C2—C1 | −8.4 (10) | C7—C6—C11—C10 | −0.1 (3) |
C2—N2A—C3A—C5A | 47.6 (9) | C6—C7—C8—C9 | −1.1 (4) |
C2—N2A—C3A—C4A | 168.7 (7) | C7—C8—C9—C10 | −0.6 (4) |
C3A—N2A—C2—C12 | 175.2 (5) | C8—C9—C10—C11 | 1.9 (4) |
C6—C1—C2—C12 | −21.6 (4) | C9—C10—C11—C6 | −1.6 (3) |
N1A—C1—C6—C7 | −44.7 (5) | C2—C12—C13—C14 | −178.8 (2) |
N1A—C1—C2—C12 | 162.6 (4) | C17—C12—C13—C14 | −0.5 (4) |
C6—C1—C2—N2A | 162.2 (6) | C2—C12—C17—C16 | 179.6 (2) |
N1A—C1—C6—C11 | 133.2 (4) | C13—C12—C17—C16 | 1.3 (4) |
C2—C1—C6—C11 | −42.8 (3) | C12—C13—C14—C15 | −0.9 (4) |
N1A—C1—C2—N2A | −13.6 (7) | C13—C14—C15—C16 | 1.5 (4) |
C2—C1—C6—C7 | 139.4 (2) | C14—C15—C16—C17 | −0.6 (4) |
N2A—C2—C12—C13 | 137.5 (6) | C15—C16—C17—C12 | −0.8 (4) |
N2A—C2—C12—C17 | −40.8 (6) | C5A—C18—C19—C20 | −179.3 (3) |
C1—C2—C12—C17 | 143.0 (2) | C23—C18—C19—C20 | −0.5 (4) |
C1—C2—C12—C13 | −38.8 (4) | C5A—C18—C23—C22 | 179.4 (3) |
N2A—C3A—C5A—N1A | −66.7 (6) | C19—C18—C23—C22 | 0.6 (4) |
C4A—C3A—C5A—C18 | 61.9 (6) | C18—C19—C20—C21 | 0.5 (4) |
N2A—C3A—C5A—C18 | 179.8 (4) | C19—C20—C21—C22 | −0.7 (3) |
C4A—C3A—C5A—N1A | 175.4 (5) | C19—C20—C21—C24 | 178.1 (2) |
N1A—C5A—C18—C19 | 143.0 (4) | C20—C21—C22—C23 | 0.9 (3) |
N1A—C5A—C18—C23 | −35.7 (5) | C24—C21—C22—C23 | −177.9 (2) |
C3A—C5A—C18—C19 | −103.3 (4) | C21—C22—C23—C18 | −0.9 (4) |
Cg3 and Cg4 are the centroids of the C6–C11 and C12–C17 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···Cg4i | 0.95 | 2.95 | 3.743 (3) | 142 |
C19—H19A···Cg4ii | 0.95 | 2.77 | 3.578 (3) | 143 |
C22—H22A···Cg3iii | 0.95 | 2.66 | 3.590 (3) | 165 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, y+1/2, −z+1/2. |
Experimental details
Crystal data | |
Chemical formula | C24H22N2 |
Mr | 338.44 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 123 |
a, b, c (Å) | 8.1986 (5), 11.8211 (6), 19.6686 (7) |
β (°) | 93.638 (4) |
V (Å3) | 1902.38 (17) |
Z | 4 |
Radiation type | Cu Kα |
µ (mm−1) | 0.53 |
Crystal size (mm) | 0.39 × 0.21 × 0.17 |
Data collection | |
Diffractometer | Agilent Xcalibur Ruby Gemini diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Agilent, 2012) |
Tmin, Tmax | 0.830, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 12585, 3892, 3044 |
Rint | 0.028 |
(sin θ/λ)max (Å−1) | 0.628 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.069, 0.214, 1.07 |
No. of reflections | 3892 |
No. of parameters | 254 |
No. of restraints | 68 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.71, −0.35 |
Computer programs: CrysAlis PRO (Agilent, 2012), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
Cg3 and Cg4 are the centroids of the C6–C11 and C12–C17 phenyl rings, respectively. |
D—H···A | D—H | H···A | D···A | D—H···A |
C10—H10A···Cg4i | 0.95 | 2.95 | 3.743 (3) | 142 |
C19—H19A···Cg4ii | 0.95 | 2.77 | 3.578 (3) | 143 |
C22—H22A···Cg3iii | 0.95 | 2.66 | 3.590 (3) | 165 |
Symmetry codes: (i) −x, −y+1, −z; (ii) −x+1, −y+2, −z; (iii) −x, y+1/2, −z+1/2. |
Acknowledgements
RJB acknowledges the NSF MRI program (grant No. CHE-0619278) for funds to purchase an X-ray diffractometer.
References
Agilent (2012). CrysAlis PRO. Agilent Technologies, Yarnton, England. Google Scholar
Anuradha, N., Chitra, S., Thiruvalluvar, A., Pandiarajan, K., Butcher, R. J., Jasinski, J. P. & Golen, J. A. (2011). Acta Cryst. E67, o2598. Web of Science CSD CrossRef IUCr Journals Google Scholar
Anuradha, N., Thiruvalluvar, A., Pandiarajan, K., Chitra, S. & Butcher, R. J. (2009). Acta Cryst. E65, o546. Web of Science CSD CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
As part of our investigations of dihydropyrazine derivatives (Anuradha et al., 2009, 2011) to compare their chemical and biological activities, we have undertaken the X-ray crystal structure analysis of the title compound.
In the title molecule, C24H22N2, Fig.1., the heterocyclic ring with the major disorder component, adopts a half-chair conformation, with all substituents equatorial. The phenyl ring at C1 makes a dihedral angle of 59.10 (11) and 79.68 (11)° with the phenyl ring at C2 and benzene ring at C5A respectively. The dihedral angle between the phenyl ring at C2 and benzene ring at C5A is 80.92 (11)°. Four atoms (N2—C3—C5—N1) of the heterocyclic ring, with their attached H atoms, and all atoms of the methyl group, are disordered over two positions; the site occupancy factors refined to 0.713 (6) and 0.287 (6). The crystal structure is stabilized by three C—H···π interactions (Table 1). No hydrogen bonds are found in the crystal structure.