organic compounds
4-[5-(Benzofuran-2-yl)-1-phenyl-1H-pyrazol-3-yl]-N,N-dimethylaniline
aDepartment of Studies in Chemistry, Manasagangotri, University of Mysore, Mysore 570 006, India, and bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India
*Correspondence e-mail: mpsadashiva@gmail.com
In the title compound, C25H21N3O, the dihedral angles between the pyrazole ring and its phenyl, aniline and benzofuran (r.m.s. deviation = 0.006 Å) substituents are 47.64 (8), 4.00 (8) and 29.12 (7)°, respectively. The methyl C atoms of the aniline group deviate from their attached ring by 0.521 (3) and 0.010 (3) Å. In the crystal, aromatic π–π stacking between the pyrazole rings [centroid–centroid separation = 3.7899 (9) Å and slippage = 0.66 Å] generates inversion dimers.
Keywords: crystal structure; benzofuran derivative; π–π stacking; inversion dimers.
CCDC reference: 1500846
Structure description
Benzofuran derivatives are found in many natural bioactive compounds (Khanam & Shamsuzzaman, 2015). In this paper, we report the synthesis and of the title benzofuran-pyrazole hybrid.
In the molecular structure of the title compound (Fig. 1), the pyrazole ring makes dihedral angles of 29.12 (7) and 47.64 (8)° withe the phenyl ring (C20–C25) and the mean plane of the benzofuran ring system (O1/C12–C19), respectively. The pyrazole ring is almost coplanar with the benzene ring (C4–C9), as indicated by the dihedral angle of 4.00 (8)°. The methyl C atoms of the aniline group deviate from their attached ring by 0.521 (3) and 0.010 (3) Å. In the crystal, aromatic π–π stacking between the pyrazole rings [centroid–centroid separation = 3.7899 (9); slippage = 0.66 Å) generates inversion dimers.
Synthesis and crystallization
A solution of 1-(benzofuran-2-yl)-3-(4-(dimethylamino)phenyl)-3-thioxopropan-1-one (0.81 g, 2.5 mmol, 1.0 eq.) and phenylhydrazine (0.40 g, 3.75 mmol, 1.5 eq.) in ethanol (10 ml) was refluxed for 3 h. The course of the reaction was monitored by
(TLC). After completion, the solvent was removed under reduced pressure, then the residue was extracted with ethyl acetate. The combined ethyl acetate layers were dried over anhydrous magnesium sulfate, filtered and the solvent removed under reduced pressure to afford the crude product which was purified by using silica gel of mesh size 60–120 using an mixture of ethyl acetate and hexane (ratio 2:8). Finally, the title compound was crystallized as colourless blocks from a solvent mixture of ethyl acetate/hexane (yield 77%, m.p. 178–180 K).Refinement
Crystal data, data collection and structure .
details are summarized in Table 1Structural data
CCDC reference: 1500846
10.1107/S2414314616013602/hb4074sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S2414314616013602/hb4074Isup2.hkl
Supporting information file. DOI: 10.1107/S2414314616013602/hb4074Isup3.cml
Data collection: APEX2 (Bruker, 2009); cell
SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).C25H21N3O | F(000) = 800 |
Mr = 379.45 | Dx = 1.258 Mg m−3 |
Monoclinic, P21/c | Cu Kα radiation, λ = 1.54178 Å |
Hall symbol: -P 2ybc | Cell parameters from 3298 reflections |
a = 9.6600 (8) Å | θ = 6.4–64.6° |
b = 14.9306 (13) Å | µ = 0.62 mm−1 |
c = 14.5976 (13) Å | T = 296 K |
β = 107.832 (3)° | Block, colourless |
V = 2004.3 (3) Å3 | 0.27 × 0.26 × 0.22 mm |
Z = 4 |
Bruker X8 Proteum diffractometer | 3298 independent reflections |
Radiation source: Bruker MicroStar microfocus rotating anode | 3063 reflections with I > 2σ(I) |
Helios multilayer optics monochromator | Rint = 0.042 |
Detector resolution: 10.7 pixels mm-1 | θmax = 64.6°, θmin = 6.4° |
φ and ω scans | h = −11→11 |
Absorption correction: multi-scan (SADABS; Bruker, 2009) | k = −17→17 |
Tmin = 0.851, Tmax = 0.877 | l = −15→17 |
17500 measured reflections |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: inferred from neighbouring sites |
R[F2 > 2σ(F2)] = 0.048 | H-atom parameters constrained |
wR(F2) = 0.135 | w = 1/[σ2(Fo2) + (0.0787P)2 + 0.3177P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max < 0.001 |
3298 reflections | Δρmax = 0.23 e Å−3 |
265 parameters | Δρmin = −0.19 e Å−3 |
0 restraints | Extinction correction: SHELXL97 (Sheldrick, 2008), FC*=KFC[1+0.001XFC2Λ3/SIN(2Θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.0131 (13) |
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 esds are taken into account in the estimation of distances, angles and torsion angles |
Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > 2sigma(F2) is used only for calculating -R-factor-obs 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 | ||
O1 | 0.30155 (11) | 0.72252 (7) | 0.33607 (8) | 0.0575 (4) | |
N1 | 0.64307 (13) | 0.61185 (8) | 0.45780 (9) | 0.0490 (4) | |
N2 | 0.69905 (13) | 0.59191 (8) | 0.55309 (9) | 0.0505 (4) | |
N3 | 0.68633 (17) | 0.56415 (13) | 0.99273 (11) | 0.0744 (6) | |
C1 | 0.50112 (15) | 0.63863 (9) | 0.43519 (11) | 0.0488 (4) | |
C2 | 0.46516 (16) | 0.63547 (10) | 0.51835 (12) | 0.0527 (5) | |
C3 | 0.59079 (16) | 0.60660 (9) | 0.59031 (11) | 0.0485 (4) | |
C4 | 0.61425 (16) | 0.59408 (9) | 0.69352 (11) | 0.0491 (5) | |
C5 | 0.74975 (17) | 0.57019 (11) | 0.75589 (12) | 0.0571 (5) | |
C6 | 0.77438 (18) | 0.56078 (12) | 0.85328 (12) | 0.0613 (5) | |
C7 | 0.66317 (19) | 0.57498 (11) | 0.89460 (12) | 0.0573 (5) | |
C8 | 0.52667 (19) | 0.59812 (11) | 0.83193 (12) | 0.0588 (5) | |
C9 | 0.50328 (17) | 0.60728 (10) | 0.73467 (12) | 0.0545 (5) | |
C10 | 0.5955 (3) | 0.6120 (2) | 1.03840 (17) | 0.1018 (11) | |
C11 | 0.8309 (2) | 0.54142 (18) | 1.05430 (14) | 0.0906 (8) | |
C12 | 0.41158 (15) | 0.66189 (10) | 0.33844 (11) | 0.0504 (4) | |
C13 | 0.22834 (16) | 0.73479 (10) | 0.24000 (12) | 0.0570 (5) | |
C14 | 0.11052 (19) | 0.79098 (13) | 0.20348 (17) | 0.0768 (7) | |
C15 | 0.0528 (2) | 0.79331 (16) | 0.10493 (19) | 0.0887 (8) | |
C16 | 0.1111 (2) | 0.74309 (17) | 0.04622 (17) | 0.0891 (8) | |
C17 | 0.2296 (2) | 0.68770 (14) | 0.08376 (14) | 0.0748 (7) | |
C18 | 0.28960 (16) | 0.68347 (11) | 0.18382 (12) | 0.0560 (5) | |
C19 | 0.40827 (17) | 0.63671 (11) | 0.25015 (12) | 0.0564 (5) | |
C20 | 0.74029 (15) | 0.61106 (10) | 0.40139 (10) | 0.0472 (4) | |
C21 | 0.74874 (17) | 0.68401 (11) | 0.34471 (12) | 0.0575 (5) | |
C22 | 0.84898 (19) | 0.68341 (12) | 0.29489 (13) | 0.0648 (6) | |
C23 | 0.94310 (19) | 0.61256 (13) | 0.30358 (12) | 0.0645 (6) | |
C24 | 0.93492 (18) | 0.54034 (12) | 0.36047 (12) | 0.0635 (6) | |
C25 | 0.83201 (17) | 0.53859 (11) | 0.40866 (11) | 0.0554 (5) | |
H2 | 0.37560 | 0.64960 | 0.52600 | 0.0630* | |
H5 | 0.82610 | 0.56030 | 0.73080 | 0.0690* | |
H6 | 0.86650 | 0.54470 | 0.89240 | 0.0740* | |
H8 | 0.44990 | 0.60750 | 0.85670 | 0.0710* | |
H9 | 0.41100 | 0.62270 | 0.69530 | 0.0650* | |
H10A | 0.61000 | 0.67520 | 1.03400 | 0.1530* | |
H10B | 0.62070 | 0.59480 | 1.10490 | 0.1530* | |
H10C | 0.49530 | 0.59760 | 1.00680 | 0.1530* | |
H11A | 0.86730 | 0.49130 | 1.02740 | 0.1360* | |
H11B | 0.82660 | 0.52610 | 1.11720 | 0.1360* | |
H11C | 0.89440 | 0.59180 | 1.05900 | 0.1360* | |
H14 | 0.07250 | 0.82520 | 0.24330 | 0.0920* | |
H15 | −0.02740 | 0.82960 | 0.07710 | 0.1060* | |
H16 | 0.06950 | 0.74660 | −0.02020 | 0.1070* | |
H17 | 0.26820 | 0.65430 | 0.04370 | 0.0900* | |
H19 | 0.47100 | 0.59650 | 0.23450 | 0.0680* | |
H21 | 0.68740 | 0.73290 | 0.34030 | 0.0690* | |
H22 | 0.85300 | 0.73130 | 0.25510 | 0.0780* | |
H23 | 1.01220 | 0.61340 | 0.27110 | 0.0770* | |
H24 | 0.99890 | 0.49260 | 0.36650 | 0.0760* | |
H25 | 0.82460 | 0.48910 | 0.44560 | 0.0660* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0438 (6) | 0.0580 (6) | 0.0693 (7) | 0.0088 (4) | 0.0151 (5) | 0.0108 (5) |
N1 | 0.0407 (6) | 0.0544 (7) | 0.0485 (7) | 0.0045 (5) | 0.0087 (5) | 0.0034 (5) |
N2 | 0.0442 (6) | 0.0556 (7) | 0.0496 (7) | 0.0042 (5) | 0.0111 (5) | 0.0028 (5) |
N3 | 0.0762 (10) | 0.0937 (11) | 0.0555 (8) | 0.0022 (8) | 0.0236 (7) | −0.0031 (7) |
C1 | 0.0406 (7) | 0.0445 (7) | 0.0579 (9) | 0.0018 (6) | 0.0099 (6) | 0.0030 (6) |
C2 | 0.0426 (8) | 0.0514 (8) | 0.0638 (9) | 0.0037 (6) | 0.0159 (7) | 0.0027 (7) |
C3 | 0.0460 (8) | 0.0427 (7) | 0.0563 (8) | 0.0008 (6) | 0.0149 (7) | 0.0007 (6) |
C4 | 0.0477 (8) | 0.0423 (7) | 0.0581 (9) | 0.0010 (6) | 0.0172 (7) | 0.0001 (6) |
C5 | 0.0470 (8) | 0.0673 (10) | 0.0592 (9) | 0.0034 (7) | 0.0195 (7) | 0.0000 (7) |
C6 | 0.0492 (8) | 0.0735 (10) | 0.0582 (9) | 0.0029 (8) | 0.0121 (7) | 0.0024 (8) |
C7 | 0.0625 (9) | 0.0558 (9) | 0.0567 (9) | −0.0027 (7) | 0.0227 (8) | −0.0034 (7) |
C8 | 0.0571 (9) | 0.0588 (9) | 0.0678 (10) | 0.0050 (7) | 0.0301 (8) | −0.0008 (7) |
C9 | 0.0491 (8) | 0.0510 (8) | 0.0640 (10) | 0.0061 (6) | 0.0184 (7) | 0.0020 (7) |
C10 | 0.123 (2) | 0.121 (2) | 0.0741 (14) | 0.0178 (16) | 0.0490 (14) | −0.0075 (13) |
C11 | 0.0872 (14) | 0.1205 (18) | 0.0563 (11) | −0.0023 (13) | 0.0105 (10) | −0.0008 (11) |
C12 | 0.0383 (7) | 0.0450 (7) | 0.0632 (9) | 0.0029 (6) | 0.0085 (6) | 0.0068 (6) |
C13 | 0.0387 (7) | 0.0545 (9) | 0.0725 (10) | −0.0014 (6) | 0.0094 (7) | 0.0188 (7) |
C14 | 0.0480 (9) | 0.0678 (11) | 0.1079 (16) | 0.0106 (8) | 0.0142 (9) | 0.0262 (10) |
C15 | 0.0556 (11) | 0.0802 (13) | 0.1105 (17) | 0.0051 (10) | −0.0038 (11) | 0.0389 (13) |
C16 | 0.0684 (12) | 0.0938 (15) | 0.0817 (13) | −0.0118 (11) | −0.0118 (11) | 0.0356 (12) |
C17 | 0.0642 (11) | 0.0815 (12) | 0.0674 (11) | −0.0074 (9) | 0.0035 (9) | 0.0099 (9) |
C18 | 0.0425 (8) | 0.0537 (8) | 0.0641 (9) | −0.0065 (6) | 0.0049 (7) | 0.0109 (7) |
C19 | 0.0465 (8) | 0.0540 (9) | 0.0621 (9) | 0.0066 (6) | 0.0069 (7) | 0.0020 (7) |
C20 | 0.0397 (7) | 0.0532 (8) | 0.0443 (7) | −0.0005 (6) | 0.0064 (6) | −0.0022 (6) |
C21 | 0.0513 (8) | 0.0533 (8) | 0.0643 (9) | 0.0009 (7) | 0.0126 (7) | 0.0042 (7) |
C22 | 0.0639 (10) | 0.0680 (10) | 0.0631 (10) | −0.0070 (8) | 0.0204 (8) | 0.0071 (8) |
C23 | 0.0596 (10) | 0.0790 (11) | 0.0587 (10) | −0.0065 (8) | 0.0238 (8) | −0.0087 (8) |
C24 | 0.0587 (9) | 0.0687 (10) | 0.0641 (10) | 0.0099 (8) | 0.0205 (8) | −0.0068 (8) |
C25 | 0.0546 (8) | 0.0551 (9) | 0.0543 (8) | 0.0051 (7) | 0.0134 (7) | 0.0014 (7) |
O1—C12 | 1.3885 (19) | C20—C21 | 1.385 (2) |
O1—C13 | 1.376 (2) | C20—C25 | 1.382 (2) |
N1—N2 | 1.3621 (18) | C21—C22 | 1.378 (3) |
N1—C1 | 1.368 (2) | C22—C23 | 1.375 (3) |
N1—C20 | 1.426 (2) | C23—C24 | 1.378 (3) |
N2—C3 | 1.336 (2) | C24—C25 | 1.383 (2) |
N3—C7 | 1.390 (2) | C2—H2 | 0.9300 |
N3—C10 | 1.443 (3) | C5—H5 | 0.9300 |
N3—C11 | 1.451 (3) | C6—H6 | 0.9300 |
C1—C2 | 1.362 (2) | C8—H8 | 0.9300 |
C1—C12 | 1.454 (2) | C9—H9 | 0.9300 |
C2—C3 | 1.408 (2) | C10—H10A | 0.9600 |
C3—C4 | 1.465 (2) | C10—H10B | 0.9600 |
C4—C5 | 1.393 (2) | C10—H10C | 0.9600 |
C4—C9 | 1.394 (2) | C11—H11A | 0.9600 |
C5—C6 | 1.375 (2) | C11—H11B | 0.9600 |
C6—C7 | 1.400 (3) | C11—H11C | 0.9600 |
C7—C8 | 1.399 (3) | C14—H14 | 0.9300 |
C8—C9 | 1.374 (2) | C15—H15 | 0.9300 |
C12—C19 | 1.334 (2) | C16—H16 | 0.9300 |
C13—C14 | 1.383 (3) | C17—H17 | 0.9300 |
C13—C18 | 1.381 (2) | C19—H19 | 0.9300 |
C14—C15 | 1.375 (4) | C21—H21 | 0.9300 |
C15—C16 | 1.382 (3) | C22—H22 | 0.9300 |
C16—C17 | 1.382 (3) | C23—H23 | 0.9300 |
C17—C18 | 1.398 (3) | C24—H24 | 0.9300 |
C18—C19 | 1.435 (2) | C25—H25 | 0.9300 |
C12—O1—C13 | 105.24 (12) | C23—C24—C25 | 120.28 (17) |
N2—N1—C1 | 111.43 (12) | C20—C25—C24 | 119.35 (15) |
N2—N1—C20 | 117.53 (12) | C1—C2—H2 | 127.00 |
C1—N1—C20 | 130.67 (13) | C3—C2—H2 | 127.00 |
N1—N2—C3 | 105.31 (12) | C4—C5—H5 | 119.00 |
C7—N3—C10 | 119.32 (17) | C6—C5—H5 | 119.00 |
C7—N3—C11 | 119.10 (16) | C5—C6—H6 | 119.00 |
C10—N3—C11 | 115.83 (17) | C7—C6—H6 | 119.00 |
N1—C1—C2 | 106.57 (13) | C7—C8—H8 | 119.00 |
N1—C1—C12 | 123.93 (14) | C9—C8—H8 | 119.00 |
C2—C1—C12 | 129.47 (14) | C4—C9—H9 | 119.00 |
C1—C2—C3 | 106.19 (14) | C8—C9—H9 | 119.00 |
N2—C3—C2 | 110.50 (14) | N3—C10—H10A | 110.00 |
N2—C3—C4 | 120.22 (14) | N3—C10—H10B | 109.00 |
C2—C3—C4 | 129.27 (15) | N3—C10—H10C | 109.00 |
C3—C4—C5 | 121.56 (15) | H10A—C10—H10B | 109.00 |
C3—C4—C9 | 121.86 (14) | H10A—C10—H10C | 110.00 |
C5—C4—C9 | 116.57 (14) | H10B—C10—H10C | 109.00 |
C4—C5—C6 | 122.18 (16) | N3—C11—H11A | 109.00 |
C5—C6—C7 | 121.16 (16) | N3—C11—H11B | 109.00 |
N3—C7—C6 | 121.59 (16) | N3—C11—H11C | 110.00 |
N3—C7—C8 | 121.66 (17) | H11A—C11—H11B | 110.00 |
C6—C7—C8 | 116.73 (15) | H11A—C11—H11C | 110.00 |
C7—C8—C9 | 121.61 (17) | H11B—C11—H11C | 109.00 |
C4—C9—C8 | 121.75 (16) | C13—C14—H14 | 122.00 |
O1—C12—C1 | 113.76 (13) | C15—C14—H14 | 122.00 |
O1—C12—C19 | 111.60 (14) | C14—C15—H15 | 119.00 |
C1—C12—C19 | 134.62 (15) | C16—C15—H15 | 119.00 |
O1—C13—C14 | 125.40 (16) | C15—C16—H16 | 119.00 |
O1—C13—C18 | 110.58 (14) | C17—C16—H16 | 119.00 |
C14—C13—C18 | 124.02 (17) | C16—C17—H17 | 121.00 |
C13—C14—C15 | 116.17 (19) | C18—C17—H17 | 121.00 |
C14—C15—C16 | 121.6 (2) | C12—C19—H19 | 127.00 |
C15—C16—C17 | 121.6 (2) | C18—C19—H19 | 126.00 |
C16—C17—C18 | 117.99 (19) | C20—C21—H21 | 120.00 |
C13—C18—C17 | 118.65 (16) | C22—C21—H21 | 120.00 |
C13—C18—C19 | 105.56 (14) | C21—C22—H22 | 120.00 |
C17—C18—C19 | 135.79 (16) | C23—C22—H22 | 120.00 |
C12—C19—C18 | 107.02 (15) | C22—C23—H23 | 120.00 |
N1—C20—C21 | 120.53 (14) | C24—C23—H23 | 120.00 |
N1—C20—C25 | 118.83 (13) | C23—C24—H24 | 120.00 |
C21—C20—C25 | 120.52 (14) | C25—C24—H24 | 120.00 |
C20—C21—C22 | 119.32 (15) | C20—C25—H25 | 120.00 |
C21—C22—C23 | 120.53 (17) | C24—C25—H25 | 120.00 |
C22—C23—C24 | 119.95 (17) | ||
C13—O1—C12—C1 | −178.98 (12) | C9—C4—C5—C6 | −0.6 (2) |
C13—O1—C12—C19 | −0.42 (17) | C3—C4—C9—C8 | −178.01 (14) |
C12—O1—C13—C14 | −179.22 (16) | C5—C4—C9—C8 | 0.7 (2) |
C12—O1—C13—C18 | 0.24 (17) | C4—C5—C6—C7 | 0.0 (3) |
C1—N1—N2—C3 | −0.12 (15) | C5—C6—C7—N3 | 178.89 (17) |
C20—N1—N2—C3 | 173.62 (12) | C5—C6—C7—C8 | 0.6 (3) |
N2—N1—C1—C2 | −0.18 (16) | N3—C7—C8—C9 | −178.84 (16) |
N2—N1—C1—C12 | −178.26 (13) | C6—C7—C8—C9 | −0.6 (2) |
C20—N1—C1—C2 | −172.85 (14) | C7—C8—C9—C4 | −0.1 (2) |
C20—N1—C1—C12 | 9.1 (2) | O1—C12—C19—C18 | 0.42 (18) |
N2—N1—C20—C21 | −127.92 (15) | C1—C12—C19—C18 | 178.58 (17) |
N2—N1—C20—C25 | 48.26 (19) | O1—C13—C14—C15 | −179.84 (17) |
C1—N1—C20—C21 | 44.4 (2) | C18—C13—C14—C15 | 0.8 (3) |
C1—N1—C20—C25 | −139.44 (16) | O1—C13—C18—C17 | −179.69 (15) |
N1—N2—C3—C2 | 0.36 (15) | O1—C13—C18—C19 | 0.0 (2) |
N1—N2—C3—C4 | −178.30 (12) | C14—C13—C18—C17 | −0.2 (3) |
C10—N3—C7—C6 | 154.9 (2) | C14—C13—C18—C19 | 179.47 (16) |
C10—N3—C7—C8 | −26.9 (3) | C13—C14—C15—C16 | −0.9 (3) |
C11—N3—C7—C6 | 2.8 (3) | C14—C15—C16—C17 | 0.4 (4) |
C11—N3—C7—C8 | −179.09 (19) | C15—C16—C17—C18 | 0.2 (3) |
N1—C1—C2—C3 | 0.39 (16) | C16—C17—C18—C13 | −0.3 (3) |
C12—C1—C2—C3 | 178.32 (14) | C16—C17—C18—C19 | −179.8 (2) |
N1—C1—C12—O1 | −152.67 (13) | C13—C18—C19—C12 | −0.25 (18) |
N1—C1—C12—C19 | 29.2 (3) | C17—C18—C19—C12 | 179.4 (2) |
C2—C1—C12—O1 | 29.7 (2) | N1—C20—C21—C22 | 176.61 (15) |
C2—C1—C12—C19 | −148.41 (19) | C25—C20—C21—C22 | 0.5 (2) |
C1—C2—C3—N2 | −0.48 (17) | N1—C20—C25—C24 | −174.72 (14) |
C1—C2—C3—C4 | 178.03 (14) | C21—C20—C25—C24 | 1.5 (2) |
N2—C3—C4—C5 | 2.5 (2) | C20—C21—C22—C23 | −2.1 (3) |
N2—C3—C4—C9 | −178.89 (13) | C21—C22—C23—C24 | 1.8 (3) |
C2—C3—C4—C5 | −175.87 (15) | C22—C23—C24—C25 | 0.3 (3) |
C2—C3—C4—C9 | 2.7 (2) | C23—C24—C25—C20 | −1.8 (2) |
C3—C4—C5—C6 | 178.05 (15) |
Acknowledgements
GSL and MPS are thankful to the UGC for financial support (grant F. No. 37–456/2009 [SR]), UGC–SAP Phase-III, New Delhi and IOE, University of Mysore, Karnataka, for analyses.
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