organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoIUCrDATA
ISSN: 2414-3146

3-Methyl-5,6-di­phenyl-1H-pyrazolo­[1,2-a]cinnolin-1-one

aOrganic & Bio-organic Chemistry, CSIR Central Leather Research Institute, Adyar, Chennai 600 020, India
*Correspondence e-mail: umanarayanclri@gmail.com

Edited by H. Stoeckli-Evans, University of Neuchâtel, Switzerland (Received 24 March 2017; accepted 10 April 2017; online 21 April 2017)

The asymmetric unit of the title compound, C24H18N2O, comprises two crystallographically independent mol­ecules (A and B), with slightly different conformations. In each mol­ecule, there is an intra­molecular C—H⋯O hydrogen bond forming an S(6) ring motif. The pyridazine rings of the pyrazolo­[1,2-a]cinnoline units have screw-boat conformations. Their mean planes are inclined to the phenyl rings by 83.81 (8) and 74.19 (8)° in mol­ecule A, and 89.72 (8) and 71.07 (8)° in mol­ecule B. In the crystal, the A and B mol­ecules are linked by a pair of C—H⋯O hydrogen bonds, forming an A–B dimer with an R22(14) ring motif. These dimers are linked by further C—H⋯O hydrogen bonds, forming ribbons propagating along the b-axis direction. The ribbons are linked by a number of C—H⋯π inter­actions, forming a three-dimensional structure.

3D view (loading...)
[Scheme 3D1]
Chemical scheme
[Scheme 1]

Structure description

Pyrazole derivatives are reported to possess varied biological activities, such as anti-inflammatory (Windholz 2003[Windholz, M. (2003). The Merck Index, 9th ed. Rahaway, New Jersey: Merck & Co.]), analgesic (Windholz 2003[Windholz, M. (2003). The Merck Index, 9th ed. Rahaway, New Jersey: Merck & Co.]), hypoglycemic, sedative (Burger & Iorio, 1979[Burger, J. C. & Iorio, L. C. (1979). Annu. Rep. Med. Chem. 14, 27-64.]), hypnotic (Burger & Iorio, 1980[Burger, J. C. & Iorio, L. C. (1980). Annu. Rep. Med. Chem. 15, 26-50.]), anti­fungal and anti­bacterial (Kalluraya & Ramesh, 2001[Kalluraya, B. & Ramesh, M. C. (2001). Indian J. Heterocycl. Chem. 11, 171-175.]).

The asymmetric unit of the title compound, is composed of two crystallographically independent mol­ecules (A and B), with slightly different conformations (Fig. 1[link]). Intra­molecular C—H⋯O hydrogen bonds generate six-membered rings, producing S(6) ring motifs (Fig1, Table 1[link]). The dihedral angles between the mean plane of the central pyridazine ring (which has a screw-boat conformation in both mol­ecules) and the two outer phenyl rings are 83.81 (8) and 74.19 (8)° in mol­ecule A, and 89.72 (8) and 71.07 (8)° in mol­ecule B.

Table 1
Hydrogen-bond geometry (Å, °)

Cg1, Cg3, Cg4, Cg11 and Cg12 are the centroids of the N1/N2/C21–C24, C1–C6, C8–C13, C1′–C6′ and C8′–C13′ rings, respectively

D—H⋯A D—H H⋯A DA D—H⋯A
C2—H2⋯O1 0.93 2.22 2.862 (2) 125
C2′—H2′⋯O1′ 0.93 2.22 2.865 (2) 126
C3—H3⋯O1′i 0.93 2.49 3.381 (2) 162
C3′—H3′⋯O1i 0.93 2.54 3.456 (2) 170
C11—H11⋯O1ii 0.93 2.49 3.274 (2) 142
C9—H9⋯Cg1iii 0.93 2.92 3.796 (2) 158
C16—H16⋯Cg3iii 0.93 3.00 3.822 (2) 149
C18—H18⋯Cg12iv 0.93 2.95 3.869 (2) 169
C18′—H18′⋯Cg4iv 0.93 2.98 3.867 (2) 161
C19—H19⋯Cg3v 0.93 2.90 3.685 (2) 143
C19′—H19′⋯Cg11vi 0.93 2.78 3.604 (2) 149
Symmetry codes: (i) -x, -y+1, -z+1; (ii) x, y-1, z; (iii) -x, -y, -z+1; (iv) -x+1, -y, -z; (v) -x+1, -y, -z+1; (vi) -x+1, -y+1, -z.
[Figure 1]
Figure 1
The mol­ecular structure of the two independent mol­ecules (A and B) of the title compound, with the atom labelling. Displacement ellipsoids are drawn at the 30% probability level. The intra­molecular C—H⋯O hydrogen bonds are shown as dashed lines (see Table 1[link]).

In the crystal, the A and B mol­ecules are linked by a pair of C—H⋯O hydrogen bonds, forming an AB dimer with an [R_{2}^{2}](14) ring motif (Fig. 2[link] and Table 1[link]). These dimers are linked by further C—H⋯O hydrogen bonds, forming ribbons propagating along the b-axis direction (Fig. 3[link] and Table 1[link]). The ribbons are linked by a number of C—H⋯π inter­actions, forming a three-dimensional structure (Table 1[link]).

[Figure 2]
Figure 2
A view along the a axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1[link]; colour code: mol­ecule A black, mol­ecule B orange).
[Figure 3]
Figure 3
A view along the b axis of the crystal packing of the title compound. The hydrogen bonds are shown as dashed lines (see Table 1[link]; colour code: mol­ecule A black, mol­ecule B orange).

Synthesis and crystallization

To a dried 50 ml round-bottom flask, fitted with a reflux condenser, were added 5-methyl-2-phenyl-2,4-di­hydro-3H-pyrazol-3-one 1 (0.3 mmol), diphenyl acetyl­ene (0.3 mmol), [RuCl2(p-cymene)]2 (5 mol%), Cu(OAc)2 (2 eq.) and AgSbF6 (20 mol%) in toluene. The reaction mixture was refluxed for 16 h. After cooling to room temperature, the reaction mixture was diluted with CH2Cl2, filtered through Celite and the filtrate concentrated under reduced pressure. The crude product was purified through a silica gel column, using hexane and ethyl acetate as eluent, giving the title compound in 70% yield. Colourless block-like crystals were obtained by slow evaporation of a solution in ethanol.

Refinement

Crystal data, data collection and structure refinement details are summarized in Table 2[link].

Table 2
Experimental details

Crystal data
Chemical formula C24H18N2O
Mr 350.40
Crystal system, space group Triclinic, P[\overline{1}]
Temperature (K) 293
a, b, c (Å) 9.9251 (4), 12.2293 (4), 15.1738 (5)
α, β, γ (°) 84.318 (2), 78.538 (2), 89.880 (2)
V3) 1795.86 (11)
Z 4
Radiation type Mo Kα
μ (mm−1) 0.08
Crystal size (mm) 0.20 × 0.15 × 0.10
 
Data collection
Diffractometer Bruker SMART APEXII CCD
Absorption correction Multi-scan (SADABS; Bruker, 20014)
Tmin, Tmax 0.984, 0.992
No. of measured, independent and observed [I > 2σ(I)] reflections 26244, 7471, 5339
Rint 0.024
(sin θ/λ)max−1) 0.629
 
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.045, 0.125, 1.01
No. of reflections 7471
No. of parameters 490
H-atom treatment H-atom parameters constrained
Δρmax, Δρmin (e Å−3) 0.31, −0.15
Computer programs: APEX2 and SAINT (Bruker, 2014[Bruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]), SHELXS97, SHELXL97 and SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Structural data


Computing details top

Data collection: APEX2 (Bruker, 2014); cell refinement: SAINT (Bruker, 2014); data reduction: SAINT (Bruker, 2014); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2009).

3-Methyl-5,6-diphenyl-1H-pyrazolo[1,2-a]cinnolin-1-one top
Crystal data top
C24H18N2OZ = 4
Mr = 350.40F(000) = 736
Triclinic, P1Dx = 1.296 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 9.9251 (4) ÅCell parameters from 7471 reflections
b = 12.2293 (4) Åθ = 1.4–26.6°
c = 15.1738 (5) ŵ = 0.08 mm1
α = 84.318 (2)°T = 293 K
β = 78.538 (2)°Block, colourless
γ = 89.880 (2)°0.20 × 0.15 × 0.10 mm
V = 1795.86 (11) Å3
Data collection top
Bruker SMART APEXII CCD
diffractometer
7471 independent reflections
Radiation source: fine-focus sealed tube5339 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.024
ω and φ scansθmax = 26.6°, θmin = 1.4°
Absorption correction: multi-scan
(SADABS; Bruker, 20014)
h = 1212
Tmin = 0.984, Tmax = 0.992k = 1513
26244 measured reflectionsl = 1719
Refinement top
Refinement on F2Secondary atom site location: difference Fourier map
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.045H-atom parameters constrained
wR(F2) = 0.125 w = 1/[σ2(Fo2) + (0.0499P)2 + 0.4013P]
where P = (Fo2 + 2Fc2)/3
S = 1.01(Δ/σ)max < 0.001
7471 reflectionsΔρmax = 0.31 e Å3
490 parametersΔρmin = 0.15 e Å3
0 restraintsExtinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methodsExtinction coefficient: 0.0046 (7)
Special details top

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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 > 2sigma(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
xyzUiso*/Ueq
C10.15479 (14)0.09128 (12)0.61216 (10)0.0482 (3)
C1'0.13725 (15)0.56650 (12)0.09148 (10)0.0498 (4)
C2'0.06903 (17)0.60730 (14)0.16999 (11)0.0618 (4)
H2'0.06470.68270.17360.074*
C20.09775 (17)0.13502 (14)0.69203 (11)0.0594 (4)
H20.09620.21070.69430.071*
C3'0.00711 (18)0.53485 (15)0.24336 (12)0.0698 (5)
H3'0.03840.56210.29610.084*
C30.04332 (18)0.06529 (15)0.76824 (11)0.0652 (4)
H30.00410.09450.82150.078*
C4'0.01280 (19)0.42348 (16)0.23837 (12)0.0728 (5)
H4'0.02890.37540.28750.087*
C40.04671 (18)0.04632 (15)0.76597 (11)0.0687 (5)
H40.00950.09250.81750.082*
C50.10524 (18)0.09005 (14)0.68738 (11)0.0627 (4)
H50.10810.16600.68660.075*
C5'0.08075 (17)0.38318 (14)0.16001 (11)0.0641 (4)
H5'0.08340.30760.15690.077*
C60.16065 (15)0.02226 (12)0.60856 (10)0.0485 (3)
C6'0.14578 (15)0.45328 (12)0.08511 (10)0.0499 (4)
C70.22899 (14)0.06595 (11)0.52486 (9)0.0462 (3)
C7'0.22902 (15)0.41255 (11)0.00459 (10)0.0466 (3)
C8'0.25727 (15)0.29247 (11)0.00764 (9)0.0463 (3)
C80.25278 (16)0.18661 (11)0.52569 (9)0.0483 (3)
C9'0.16563 (18)0.21977 (14)0.01398 (12)0.0646 (4)
H9'0.08950.24640.03580.078*
C90.14860 (19)0.25754 (14)0.51906 (13)0.0714 (5)
H90.06440.22970.51040.086*
C100.1679 (2)0.37019 (16)0.52519 (14)0.0842 (6)
H100.09650.41730.52090.101*
C10'0.1860 (2)0.10750 (15)0.00343 (13)0.0736 (5)
H10'0.12350.05930.01810.088*
C110.2905 (3)0.41224 (14)0.53747 (12)0.0785 (6)
H110.30240.48790.54260.094*
C11'0.2976 (2)0.06734 (14)0.02845 (11)0.0698 (5)
H11'0.31020.00810.03660.084*
C12'0.3904 (2)0.13831 (13)0.04833 (12)0.0689 (5)
H12'0.46710.11110.06920.083*
C120.3954 (2)0.34339 (14)0.54221 (12)0.0751 (5)
H120.47980.37210.54960.090*
C13'0.37103 (18)0.25057 (12)0.03771 (11)0.0573 (4)
H13'0.43540.29820.05100.069*
C130.37763 (19)0.23078 (13)0.53616 (11)0.0600 (4)
H130.45040.18440.53920.072*
C14'0.28439 (14)0.48240 (11)0.06700 (9)0.0458 (3)
C140.27179 (14)0.00173 (11)0.44925 (9)0.0450 (3)
C150.34601 (15)0.03659 (11)0.36324 (9)0.0454 (3)
C15'0.37988 (15)0.44902 (11)0.14754 (9)0.0471 (3)
C16'0.33317 (18)0.39598 (13)0.21222 (11)0.0612 (4)
H16'0.24010.37870.20480.073*
C160.27580 (18)0.08795 (14)0.30889 (11)0.0611 (4)
H160.18110.09850.32600.073*
C17'0.4235 (2)0.36848 (16)0.28764 (12)0.0784 (6)
H17'0.39130.33400.33150.094*
C170.3451 (2)0.12393 (15)0.22904 (12)0.0777 (6)
H170.29690.15790.19230.093*
C180.4851 (2)0.10957 (16)0.20403 (12)0.0797 (6)
H180.53180.13370.15020.096*
C18'0.5605 (2)0.39185 (18)0.29805 (13)0.0832 (6)
H18'0.62160.37290.34890.100*
C19'0.60834 (19)0.44324 (18)0.23369 (13)0.0783 (6)
H19'0.70170.45910.24110.094*
C190.5559 (2)0.05984 (16)0.25822 (12)0.0739 (5)
H190.65080.05050.24120.089*
C200.48752 (16)0.02358 (14)0.33765 (11)0.0586 (4)
H200.53640.00980.37430.070*
C20'0.51909 (17)0.47125 (14)0.15853 (11)0.0613 (4)
H20'0.55220.50530.11480.074*
C21'0.28812 (17)0.68383 (13)0.12931 (11)0.0566 (4)
C210.26618 (16)0.20089 (13)0.38316 (11)0.0574 (4)
C22'0.3399 (2)0.67642 (15)0.22668 (12)0.0765 (5)
H22A0.33790.74770.25920.115*
H22B0.28290.62600.24820.115*
H22C0.43270.65080.23600.115*
C220.2999 (2)0.18924 (15)0.28496 (12)0.0785 (6)
H22D0.39190.16310.26910.118*
H22E0.29280.25930.25170.118*
H22F0.23670.13780.27050.118*
C23'0.25706 (18)0.77768 (13)0.08866 (12)0.0623 (4)
H23'0.27020.84840.11800.075*
C230.24147 (19)0.29558 (14)0.42277 (13)0.0684 (5)
H230.24880.36540.39150.082*
C240.20346 (18)0.27457 (13)0.51675 (13)0.0644 (4)
C24'0.20272 (17)0.75271 (12)0.00338 (12)0.0570 (4)
N1'0.20321 (13)0.63712 (10)0.01742 (9)0.0528 (3)
N10.20948 (13)0.15955 (10)0.53328 (9)0.0533 (3)
N20.24796 (13)0.11533 (9)0.44992 (8)0.0507 (3)
N2'0.25753 (13)0.59608 (9)0.06569 (8)0.0515 (3)
O10.16919 (17)0.33509 (10)0.57734 (10)0.0944 (5)
O1'0.15812 (14)0.81121 (9)0.06473 (9)0.0781 (4)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0416 (8)0.0506 (8)0.0524 (9)0.0037 (6)0.0093 (6)0.0049 (7)
C1'0.0439 (8)0.0501 (8)0.0539 (9)0.0086 (6)0.0078 (7)0.0020 (7)
C2'0.0593 (10)0.0597 (10)0.0626 (10)0.0165 (8)0.0026 (8)0.0075 (8)
C20.0602 (10)0.0574 (9)0.0614 (10)0.0112 (8)0.0100 (8)0.0145 (8)
C3'0.0644 (11)0.0756 (12)0.0605 (10)0.0169 (9)0.0063 (8)0.0024 (9)
C30.0647 (11)0.0761 (12)0.0531 (10)0.0166 (9)0.0047 (8)0.0135 (8)
C4'0.0691 (12)0.0745 (12)0.0607 (11)0.0063 (9)0.0129 (9)0.0093 (9)
C40.0726 (12)0.0734 (12)0.0505 (9)0.0114 (9)0.0058 (8)0.0027 (8)
C50.0715 (11)0.0561 (9)0.0531 (9)0.0072 (8)0.0024 (8)0.0002 (7)
C5'0.0628 (10)0.0613 (10)0.0594 (10)0.0054 (8)0.0053 (8)0.0019 (8)
C60.0452 (8)0.0482 (8)0.0500 (8)0.0040 (6)0.0052 (6)0.0036 (6)
C6'0.0454 (8)0.0482 (8)0.0541 (9)0.0066 (6)0.0064 (7)0.0026 (7)
C70.0458 (8)0.0440 (8)0.0465 (8)0.0002 (6)0.0049 (6)0.0025 (6)
C7'0.0471 (8)0.0428 (7)0.0484 (8)0.0020 (6)0.0075 (6)0.0014 (6)
C8'0.0520 (8)0.0429 (7)0.0402 (7)0.0017 (6)0.0013 (6)0.0022 (6)
C80.0597 (9)0.0431 (8)0.0376 (7)0.0032 (7)0.0004 (6)0.0022 (6)
C9'0.0611 (10)0.0590 (10)0.0739 (11)0.0073 (8)0.0144 (8)0.0048 (8)
C90.0637 (11)0.0624 (11)0.0825 (13)0.0136 (9)0.0004 (9)0.0097 (9)
C100.0969 (16)0.0608 (12)0.0820 (13)0.0337 (11)0.0169 (12)0.0143 (10)
C10'0.0861 (14)0.0561 (10)0.0740 (12)0.0243 (10)0.0017 (10)0.0122 (9)
C110.1251 (19)0.0445 (9)0.0549 (10)0.0006 (11)0.0083 (11)0.0053 (8)
C11'0.1054 (15)0.0416 (9)0.0559 (10)0.0016 (9)0.0014 (10)0.0024 (7)
C12'0.0926 (13)0.0501 (9)0.0675 (11)0.0167 (9)0.0236 (10)0.0081 (8)
C120.1071 (15)0.0523 (10)0.0682 (11)0.0205 (10)0.0210 (10)0.0112 (8)
C13'0.0688 (10)0.0462 (8)0.0607 (10)0.0050 (7)0.0203 (8)0.0093 (7)
C130.0759 (11)0.0492 (9)0.0579 (10)0.0065 (8)0.0181 (8)0.0101 (7)
C14'0.0462 (8)0.0428 (7)0.0483 (8)0.0037 (6)0.0097 (6)0.0030 (6)
C140.0425 (8)0.0428 (7)0.0493 (8)0.0000 (6)0.0089 (6)0.0037 (6)
C150.0501 (8)0.0428 (7)0.0417 (7)0.0005 (6)0.0080 (6)0.0011 (6)
C15'0.0512 (9)0.0449 (8)0.0432 (8)0.0018 (6)0.0082 (6)0.0025 (6)
C16'0.0658 (10)0.0636 (10)0.0555 (10)0.0019 (8)0.0153 (8)0.0055 (8)
C160.0643 (10)0.0670 (10)0.0528 (9)0.0109 (8)0.0150 (8)0.0027 (8)
C17'0.1082 (17)0.0792 (13)0.0503 (10)0.0105 (11)0.0180 (10)0.0149 (9)
C170.1137 (18)0.0716 (12)0.0523 (10)0.0074 (11)0.0253 (11)0.0102 (9)
C180.1079 (17)0.0764 (13)0.0472 (10)0.0192 (12)0.0021 (10)0.0057 (9)
C18'0.0907 (16)0.0978 (15)0.0504 (11)0.0261 (12)0.0074 (10)0.0000 (10)
C19'0.0547 (10)0.1083 (15)0.0637 (12)0.0098 (10)0.0003 (9)0.0070 (11)
C190.0629 (11)0.0847 (13)0.0644 (11)0.0144 (10)0.0055 (9)0.0026 (10)
C200.0508 (9)0.0670 (10)0.0561 (9)0.0002 (8)0.0075 (7)0.0042 (8)
C20'0.0540 (10)0.0767 (11)0.0519 (9)0.0005 (8)0.0096 (7)0.0019 (8)
C21'0.0596 (10)0.0503 (9)0.0579 (9)0.0009 (7)0.0142 (7)0.0097 (7)
C210.0536 (9)0.0503 (9)0.0644 (10)0.0013 (7)0.0104 (7)0.0097 (7)
C22'0.0976 (15)0.0638 (11)0.0606 (11)0.0032 (10)0.0077 (10)0.0136 (8)
C220.1015 (15)0.0645 (11)0.0625 (11)0.0042 (10)0.0113 (10)0.0177 (9)
C23'0.0667 (11)0.0463 (9)0.0728 (11)0.0015 (7)0.0160 (9)0.0036 (8)
C230.0709 (11)0.0463 (9)0.0822 (13)0.0048 (8)0.0094 (9)0.0093 (8)
C240.0689 (11)0.0429 (9)0.0784 (12)0.0070 (8)0.0073 (9)0.0056 (8)
C24'0.0586 (10)0.0428 (8)0.0698 (11)0.0020 (7)0.0128 (8)0.0061 (7)
N1'0.0562 (8)0.0447 (7)0.0556 (8)0.0068 (6)0.0059 (6)0.0071 (6)
N10.0580 (8)0.0427 (7)0.0574 (8)0.0003 (6)0.0065 (6)0.0071 (6)
N20.0557 (8)0.0441 (7)0.0497 (7)0.0024 (5)0.0062 (6)0.0004 (5)
N2'0.0579 (8)0.0435 (7)0.0497 (7)0.0058 (6)0.0057 (6)0.0013 (5)
O10.1340 (13)0.0476 (7)0.0939 (10)0.0064 (7)0.0012 (9)0.0177 (7)
O1'0.0954 (10)0.0518 (7)0.0843 (9)0.0024 (6)0.0063 (7)0.0170 (6)
Geometric parameters (Å, º) top
C1—C21.389 (2)C13—H130.9300
C1—C61.396 (2)C14'—N2'1.4164 (17)
C1—N11.4036 (19)C14'—C15'1.4817 (19)
C1'—C2'1.386 (2)C14—N21.4094 (17)
C1'—N1'1.3982 (19)C14—C151.4844 (19)
C1'—C6'1.399 (2)C15—C161.376 (2)
C2'—C3'1.392 (2)C15—C201.386 (2)
C2'—H2'0.9300C15'—C16'1.381 (2)
C2—C31.384 (2)C15'—C20'1.383 (2)
C2—H20.9300C16'—C17'1.376 (2)
C3'—C4'1.372 (2)C16'—H16'0.9300
C3'—H3'0.9300C16—C171.381 (2)
C3—C41.369 (2)C16—H160.9300
C3—H30.9300C17'—C18'1.365 (3)
C4'—C5'1.381 (2)C17'—H17'0.9300
C4'—H4'0.9300C17—C181.373 (3)
C4—C51.377 (2)C17—H170.9300
C4—H40.9300C18—C191.367 (3)
C5—C61.402 (2)C18—H180.9300
C5—H50.9300C18'—C19'1.371 (3)
C5'—C6'1.400 (2)C18'—H18'0.9300
C5'—H5'0.9300C19'—C20'1.370 (2)
C6—C71.4660 (19)C19'—H19'0.9300
C6'—C7'1.463 (2)C19—C201.374 (2)
C7—C141.3422 (19)C19—H190.9300
C7—C81.4931 (19)C20—H200.9300
C7'—C14'1.3388 (19)C20'—H20'0.9300
C7'—C8'1.4924 (19)C21'—C23'1.362 (2)
C8'—C13'1.379 (2)C21'—N2'1.3621 (18)
C8'—C9'1.380 (2)C21'—C22'1.476 (2)
C8—C91.376 (2)C21—C231.357 (2)
C8—C131.382 (2)C21—N21.3682 (18)
C9'—C10'1.386 (2)C21—C221.482 (2)
C9'—H9'0.9300C22'—H22A0.9600
C9—C101.387 (3)C22'—H22B0.9600
C9—H90.9300C22'—H22C0.9600
C10—C111.359 (3)C22—H22D0.9600
C10—H100.9300C22—H22E0.9600
C10'—C11'1.365 (3)C22—H22F0.9600
C10'—H10'0.9300C23'—C24'1.397 (2)
C11—C121.358 (3)C23'—H23'0.9300
C11—H110.9300C23—C241.399 (3)
C11'—C12'1.363 (3)C23—H230.9300
C11'—H11'0.9300C24—O11.232 (2)
C12'—C13'1.384 (2)C24—N11.4074 (19)
C12'—H12'0.9300C24'—O1'1.2415 (19)
C12—C131.384 (2)C24'—N1'1.4087 (19)
C12—H120.9300N1'—N2'1.4095 (17)
C13'—H13'0.9300N1—N21.4075 (17)
C2—C1—C6120.69 (14)C7—C14—N2119.67 (13)
C2—C1—N1121.18 (13)C7—C14—C15123.21 (13)
C6—C1—N1118.12 (13)N2—C14—C15117.11 (12)
C2'—C1'—N1'121.02 (14)C16—C15—C20119.05 (14)
C2'—C1'—C6'120.91 (14)C16—C15—C14120.50 (14)
N1'—C1'—C6'118.03 (13)C20—C15—C14120.42 (13)
C1'—C2'—C3'119.71 (16)C16'—C15'—C20'118.99 (15)
C1'—C2'—H2'120.1C16'—C15'—C14'121.52 (14)
C3'—C2'—H2'120.1C20'—C15'—C14'119.49 (13)
C3—C2—C1119.63 (15)C17'—C16'—C15'120.37 (17)
C3—C2—H2120.2C17'—C16'—H16'119.8
C1—C2—H2120.2C15'—C16'—H16'119.8
C4'—C3'—C2'120.44 (16)C15—C16—C17120.42 (17)
C4'—C3'—H3'119.8C15—C16—H16119.8
C2'—C3'—H3'119.8C17—C16—H16119.8
C4—C3—C2120.64 (15)C18'—C17'—C16'120.01 (18)
C4—C3—H3119.7C18'—C17'—H17'120.0
C2—C3—H3119.7C16'—C17'—H17'120.0
C3'—C4'—C5'119.67 (16)C18—C17—C16119.95 (17)
C3'—C4'—H4'120.2C18—C17—H17120.0
C5'—C4'—H4'120.2C16—C17—H17120.0
C3—C4—C5119.92 (16)C19—C18—C17119.99 (17)
C3—C4—H4120.0C19—C18—H18120.0
C5—C4—H4120.0C17—C18—H18120.0
C4—C5—C6121.22 (15)C17'—C18'—C19'120.12 (17)
C4—C5—H5119.4C17'—C18'—H18'119.9
C6—C5—H5119.4C19'—C18'—H18'119.9
C4'—C5'—C6'121.63 (16)C20'—C19'—C18'120.29 (18)
C4'—C5'—H5'119.2C20'—C19'—H19'119.9
C6'—C5'—H5'119.2C18'—C19'—H19'119.9
C1—C6—C5117.89 (14)C18—C19—C20120.38 (18)
C1—C6—C7119.40 (13)C18—C19—H19119.8
C5—C6—C7122.66 (13)C20—C19—H19119.8
C1'—C6'—C5'117.62 (14)C19—C20—C15120.20 (16)
C1'—C6'—C7'119.61 (13)C19—C20—H20119.9
C5'—C6'—C7'122.62 (13)C15—C20—H20119.9
C14—C7—C6120.49 (13)C19'—C20'—C15'120.20 (16)
C14—C7—C8120.62 (13)C19'—C20'—H20'119.9
C6—C7—C8118.88 (12)C15'—C20'—H20'119.9
C14'—C7'—C6'120.53 (13)C23'—C21'—N2'108.69 (14)
C14'—C7'—C8'121.55 (13)C23'—C21'—C22'126.36 (15)
C6'—C7'—C8'117.81 (12)N2'—C21'—C22'124.89 (15)
C13'—C8'—C9'118.28 (14)C23—C21—N2108.06 (15)
C13'—C8'—C7'120.80 (13)C23—C21—C22126.95 (15)
C9'—C8'—C7'120.79 (14)N2—C21—C22124.91 (15)
C9—C8—C13118.08 (15)C21'—C22'—H22A109.5
C9—C8—C7120.53 (15)C21'—C22'—H22B109.5
C13—C8—C7121.36 (14)H22A—C22'—H22B109.5
C8'—C9'—C10'120.64 (17)C21'—C22'—H22C109.5
C8'—C9'—H9'119.7H22A—C22'—H22C109.5
C10'—C9'—H9'119.7H22B—C22'—H22C109.5
C8—C9—C10120.65 (19)C21—C22—H22D109.5
C8—C9—H9119.7C21—C22—H22E109.5
C10—C9—H9119.7H22D—C22—H22E109.5
C11—C10—C9120.41 (18)C21—C22—H22F109.5
C11—C10—H10119.8H22D—C22—H22F109.5
C9—C10—H10119.8H22E—C22—H22F109.5
C11'—C10'—C9'120.26 (17)C21'—C23'—C24'110.44 (14)
C11'—C10'—H10'119.9C21'—C23'—H23'124.8
C9'—C10'—H10'119.9C24'—C23'—H23'124.8
C12—C11—C10119.77 (17)C21—C23—C24111.16 (15)
C12—C11—H11120.1C21—C23—H23124.4
C10—C11—H11120.1C24—C23—H23124.4
C12'—C11'—C10'119.70 (16)O1—C24—C23132.52 (16)
C12'—C11'—H11'120.1O1—C24—N1123.03 (16)
C10'—C11'—H11'120.1C23—C24—N1104.44 (14)
C11'—C12'—C13'120.41 (17)O1'—C24'—C23'132.34 (15)
C11'—C12'—H12'119.8O1'—C24'—N1'122.78 (15)
C13'—C12'—H12'119.8C23'—C24'—N1'104.86 (14)
C11—C12—C13120.43 (19)C1'—N1'—C24'129.65 (13)
C11—C12—H12119.8C1'—N1'—N2'120.51 (11)
C13—C12—H12119.8C24'—N1'—N2'108.48 (12)
C8'—C13'—C12'120.68 (16)C1—N1—N2120.48 (11)
C8'—C13'—H13'119.7C1—N1—C24129.01 (13)
C12'—C13'—H13'119.7N2—N1—C24108.60 (12)
C8—C13—C12120.63 (17)C21—N2—N1107.72 (12)
C8—C13—H13119.7C21—N2—C14132.80 (13)
C12—C13—H13119.7N1—N2—C14119.19 (11)
C7'—C14'—N2'119.45 (13)C21'—N2'—N1'107.52 (12)
C7'—C14'—C15'123.80 (13)C21'—N2'—C14'132.91 (13)
N2'—C14'—C15'116.67 (12)N1'—N2'—C14'119.08 (11)
N1'—C1'—C2'—C3'178.48 (15)N2'—C14'—C15'—C16'106.61 (16)
C6'—C1'—C2'—C3'0.5 (2)C7'—C14'—C15'—C20'103.33 (18)
C6—C1—C2—C31.5 (2)N2'—C14'—C15'—C20'73.41 (18)
N1—C1—C2—C3179.25 (14)C20'—C15'—C16'—C17'1.8 (2)
C1'—C2'—C3'—C4'0.2 (3)C14'—C15'—C16'—C17'178.25 (15)
C1—C2—C3—C40.8 (3)C20—C15—C16—C171.3 (2)
C2'—C3'—C4'—C5'0.1 (3)C14—C15—C16—C17179.75 (14)
C2—C3—C4—C50.3 (3)C15'—C16'—C17'—C18'1.2 (3)
C3—C4—C5—C60.7 (3)C15—C16—C17—C180.7 (3)
C3'—C4'—C5'—C6'0.6 (3)C16—C17—C18—C190.1 (3)
C2—C1—C6—C51.1 (2)C16'—C17'—C18'—C19'0.3 (3)
N1—C1—C6—C5179.67 (14)C17'—C18'—C19'—C20'0.1 (3)
C2—C1—C6—C7176.28 (13)C17—C18—C19—C200.3 (3)
N1—C1—C6—C73.0 (2)C18—C19—C20—C150.4 (3)
C4—C5—C6—C10.1 (2)C16—C15—C20—C191.2 (2)
C4—C5—C6—C7177.30 (15)C14—C15—C20—C19179.58 (14)
C2'—C1'—C6'—C5'1.2 (2)C18'—C19'—C20'—C15'0.7 (3)
N1'—C1'—C6'—C5'179.27 (14)C16'—C15'—C20'—C19'1.6 (2)
C2'—C1'—C6'—C7'174.41 (14)C14'—C15'—C20'—C19'178.47 (15)
N1'—C1'—C6'—C7'3.6 (2)N2'—C21'—C23'—C24'0.97 (19)
C4'—C5'—C6'—C1'1.3 (2)C22'—C21'—C23'—C24'176.27 (16)
C4'—C5'—C6'—C7'174.20 (16)N2—C21—C23—C241.2 (2)
C1—C6—C7—C147.5 (2)C22—C21—C23—C24175.78 (17)
C5—C6—C7—C14175.24 (15)C21—C23—C24—O1177.8 (2)
C1—C6—C7—C8171.18 (13)C21—C23—C24—N11.4 (2)
C5—C6—C7—C86.0 (2)C21'—C23'—C24'—O1'177.99 (18)
C1'—C6'—C7'—C14'7.5 (2)C21'—C23'—C24'—N1'0.52 (19)
C5'—C6'—C7'—C14'177.10 (15)C2'—C1'—N1'—C24'7.1 (2)
C1'—C6'—C7'—C8'168.57 (13)C6'—C1'—N1'—C24'174.87 (14)
C5'—C6'—C7'—C8'6.9 (2)C2'—C1'—N1'—N2'172.14 (13)
C14'—C7'—C8'—C13'86.48 (19)C6'—C1'—N1'—N2'9.8 (2)
C6'—C7'—C8'—C13'89.52 (18)O1'—C24'—N1'—C1'12.4 (3)
C14'—C7'—C8'—C9'97.74 (18)C23'—C24'—N1'—C1'166.32 (15)
C6'—C7'—C8'—C9'86.27 (18)O1'—C24'—N1'—N2'178.79 (15)
C14—C7—C8—C9100.48 (18)C23'—C24'—N1'—N2'0.10 (16)
C6—C7—C8—C980.80 (18)C2—C1—N1—N2170.43 (13)
C14—C7—C8—C1381.75 (19)C6—C1—N1—N210.3 (2)
C6—C7—C8—C1396.97 (17)C2—C1—N1—C248.1 (2)
C13'—C8'—C9'—C10'1.6 (2)C6—C1—N1—C24172.68 (15)
C7'—C8'—C9'—C10'174.26 (15)O1—C24—N1—C114.2 (3)
C13—C8—C9—C101.7 (2)C23—C24—N1—C1165.04 (15)
C7—C8—C9—C10176.15 (15)O1—C24—N1—N2178.26 (17)
C8—C9—C10—C110.3 (3)C23—C24—N1—N21.02 (17)
C8'—C9'—C10'—C11'0.1 (3)C23—C21—N2—N10.54 (17)
C9—C10—C11—C121.1 (3)C22—C21—N2—N1176.55 (16)
C9'—C10'—C11'—C12'1.2 (3)C23—C21—N2—C14173.02 (15)
C10'—C11'—C12'—C13'1.0 (3)C22—C21—N2—C149.9 (3)
C10—C11—C12—C131.1 (3)C1—N1—N2—C21165.95 (13)
C9'—C8'—C13'—C12'1.8 (2)C24—N1—N2—C210.32 (16)
C7'—C8'—C13'—C12'174.04 (14)C1—N1—N2—C1419.45 (19)
C11'—C12'—C13'—C8'0.6 (3)C24—N1—N2—C14174.92 (13)
C9—C8—C13—C121.7 (2)C7—C14—N2—C21172.29 (15)
C7—C8—C13—C12176.11 (14)C15—C14—N2—C218.5 (2)
C11—C12—C13—C80.3 (3)C7—C14—N2—N114.7 (2)
C6'—C7'—C14'—N2'2.4 (2)C15—C14—N2—N1164.52 (12)
C8'—C7'—C14'—N2'178.27 (13)C23'—C21'—N2'—N1'1.00 (17)
C6'—C7'—C14'—C15'174.27 (13)C22'—C21'—N2'—N1'176.29 (15)
C8'—C7'—C14'—C15'1.6 (2)C23'—C21'—N2'—C14'170.62 (15)
C6—C7—C14—N21.5 (2)C22'—C21'—N2'—C14'12.1 (3)
C8—C7—C14—N2179.84 (13)C1'—N1'—N2'—C21'167.21 (13)
C6—C7—C14—C15177.75 (13)C24'—N1'—N2'—C21'0.68 (16)
C8—C7—C14—C151.0 (2)C1'—N1'—N2'—C14'19.80 (19)
C7—C14—C15—C1677.33 (19)C24'—N1'—N2'—C14'172.30 (12)
N2—C14—C15—C16103.45 (16)C7'—C14'—N2'—C21'173.38 (15)
C7—C14—C15—C20101.06 (17)C15'—C14'—N2'—C21'9.7 (2)
N2—C14—C15—C2078.16 (17)C7'—C14'—N2'—N1'15.8 (2)
C7'—C14'—C15'—C16'76.6 (2)C15'—C14'—N2'—N1'161.12 (12)
Hydrogen-bond geometry (Å, º) top
Cg1, Cg3, Cg4, Cg11 and Cg12 are the centroids of the N1/N2/C21–C24, C1–C6, C8–C13, C1'–C6' and C8'–C13' rings, respectively
D—H···AD—HH···AD···AD—H···A
C2—H2···O10.932.222.862 (2)125
C2—H2···O10.932.222.865 (2)126
C3—H3···O1i0.932.493.381 (2)162
C3—H3···O1i0.932.543.456 (2)170
C11—H11···O1ii0.932.493.274 (2)142
C9—H9···Cg1iii0.932.923.796 (2)158
C16—H16···Cg3iii0.933.003.822 (2)149
C18—H18···Cg12iv0.932.953.869 (2)169
C18—H18···Cg4iv0.932.983.867 (2)161
C19—H19···Cg3v0.932.903.685 (2)143
C19—H19···Cg11vi0.932.783.604 (2)149
Symmetry codes: (i) x, y+1, z+1; (ii) x, y1, z; (iii) x, y, z+1; (iv) x+1, y, z; (v) x+1, y, z+1; (vi) x+1, y+1, z.
 

Acknowledgements

The authors thank the Department of Chemistry, IIT, Chennai, India, for the X-ray intensity data collection.

References

First citationBruker (2014). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationBurger, J. C. & Iorio, L. C. (1979). Annu. Rep. Med. Chem. 14, 27–64.  Google Scholar
First citationBurger, J. C. & Iorio, L. C. (1980). Annu. Rep. Med. Chem. 15, 26–50.  Google Scholar
First citationKalluraya, B. & Ramesh, M. C. (2001). Indian J. Heterocycl. Chem. 11, 171–175.  CAS Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals Google Scholar
First citationWindholz, M. (2003). The Merck Index, 9th ed. Rahaway, New Jersey: Merck & Co.  Google Scholar

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