research communications
Isoquinolinium 5-(2,4-dinitrophenyl)-1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-olate:
Hirshfeld surface analysis and pharmacological evaluationaPG and Research Department of Chemistry, Seethalakshmi Ramaswami College, Tiruchirappalli 620 002, Tamil Nadu, India
*Correspondence e-mail: kalaivbalaj@yahoo.co.in
The 9H8N+·C12H9N4O7−, which exhibits anticonvulsant and hypnotic activities, comprises one anion and one cation interacting via an N—H⋯O hydrogen bond. In the anion, the six-membered rings are inclined each to other at 42.78 (9)°. The nitro groups in the 2,4-dinitrophenyl fragment attached to the aromatic ring in the para and ortho positions are twisted from its plane by 3.1 (2) and 45.5 (2)°, respectively. In the crystal, weak C—H⋯O hydrogen bonds consolidate the crystal packing. The Hirshfeld surface analysis revealed that O⋯H/H⋯O intermolecular contacts predominate in the crystal packing.
of the title salt CKeywords: crystal structure; 3D Hirshfeld analysis; 1,3-dimethylbarbituric acid; anticonvulsant activity; hypnotic activity.
CCDC reference: 1444879
1. Chemical context
et al., 2003). Epilepsy (convulsion) is a life-threatening neurological disorder which requires immediate treatment with suitable drugs (Shorvon, 2004). have been proved to be potent drugs for this dreadful disorder (Nadkarni et al., 2005). The isoquinoline unit also displays a wide spectrum of activity and it is an important component of many biologically active (Montalban, 2011). Since 2008, we have been periodically synthesizing new barbiturate derivatives and exploring their anticonvulsant activity (Kalaivani et al., 2008; Kalaivani & Malarvizhi, 2009; Kalaivani & Buvaneswari, 2010; Manickkam & Kalaivani, 2011; Babykala & Kalaivani, 2012; Buvaneswari & Kalaivani, 2013; Vaduganathan & Doraisamyraja, 2014; Gomathi & Kalaivani, 2015). The title molecular salt, which is a new derivative of 1,3-dimethylbarbituric acid (barbiturate), was recently obtained by our group. Herewith we report its crystal structure.
play a significant role in biological systems (Hueso-Ureña2. Structural commentary
In the title compound, (I) (Fig. 1), all the bond lengths and bond angles are normal and comparable with those observed in the related (Sridevi & Kalaivani, 2012; Gunaseelan & Doraisamyraja, 2014). The plane of the dinitroaromatic ring C1–C6 and that of the barbiturate ring C7/C8/N4/C9/N3/C10 form a dihedral angle of 42.78 (9)°. The nitro groups in the 2,4-dinitrophenyl fragment attached to the aromatic ring in the para and ortho positions are twisted from its plane by 3.1 (2) and 45.5 (2)°, respectively. Thus the para nitro group is more involved in delocalizing the negative charge than the ortho nitro group in the anionic part. This sort of delocalization of the charge over a large area imparts a maroon red colour to the title compound.
3. Supramolecular features
The aminium group is involved in formation of an N—H⋯O hydrogen bond (Table 1) between the isoquinolinium cation (N5—H5A) and the deprotonated enol oxygen atom O7. In the crystal, weak C—H⋯O hydrogen bonds (Table 1) consolidate the crystal packing (Fig. 2). An R21(6) motif is generated by the C—H groups [C13—H13 and C20—H20] of the isoquinolinium cation and oxygen atom O5 of the carbonyl group of the barbiturate ring of the anion. Although there are three rings with cyclically delocalized π electron clouds, no π–π stacking interactions are observed between them.
4. 3D Hirshfeld Surface Analysis and 2D Fingerprint Analysis
Hirshfeld surfaces (Spackman & Jayatilaka, 2009) and the associated 2D-fingerprint plots (McKinnon et al., 2007) of the title molecular salt have been generated using Crystal Explorer 3.1 (Wolff et al., 2013). Hirshfeld surfaces mapped with different properties, e.g. de, dnorm, di, shapeindex, curvedness, have proven to be a useful visualization tool for the analysis of intermolecular interactions. The 2D-fingerprint plots of Hirshfeld surfaces have been used to pinpoint and scrutinize the percentage of hydrogen-bonding interactions present in the The presented graphical plots use the same red-white-blue color scheme, wherein red highlights the shortest intermolecular atomic contacts (negative dnorm values), white is used for contacts around the van der Waals separation, and blue corresponds to longer ones (positive dnorm values). Hirshfeld surface analysis of the new barbiturate of present interest has dnorm values ranging from −0.723 (red) to 1.464 (blue), as specified in Fig. 3. The globularity value (a measure of the degree to which the surface area differs from that of the shape) is less than 1 (0.743), implying a more structured molecular surface and it is an oblate object (asphericity, 0.282). 2D-Fingerprint plots showing contributions from different contacts: (a) overall interactions (b) C⋯H/H⋯C (c) C⋯O/O⋯C (d) H⋯H (e) O⋯H/H⋯O (f) N⋯O/O⋯N are depicted in Fig. 4, and Fig. 5 (pie chart) clearly demonstrates that the O⋯H/H⋯O interactions dominate in the crystal.
5. Pharmacological activity
Epilepsy affects about 0.5% of the world's population. A seizure is caused by an asynchronous high-frequency discharge of a group of neurons, starting locally and spreading to a varying extent to affect other parts of the brain. 1,3-Dimethylbarbituric acid is the most significant compound with a heterocyclic structure and exists in two tautomeric forms (keto and enol) due to the mobility of active methylene group hydrogen atoms in its molecule. et al.,1973; Kulkarni, 1999). It reduces all phases of convulsion (tonic-flexor, tonic-extensor, clonic-convulsion and stupor) even at low dosage (25 mg kg−1) and the animals recovered after the experiment.
are drugs that act as central nervous system depressants and can therefore produce a wide spectrum of effects from mild sedation to total anaesthesia. They are also effective as anxiolytics, hypnotics and anticonvulsants. As the molecular salt of the present investigation is a derivative of 1,3-dimethylbarbituric acid, it has been subjected to the Maximal Electro Shock method to evaluate its anticonvulsant activity (Misra6. Synthesis and crystallization
1-Chloro-2,4-dinitrobenzene (2.02 g, 0.01 mol) in 40 mL of absolute alcohol was mixed with 1,3-dimethylbarbituric acid (1.56 g, 0.01 mol) in 30 mL ethanol. To this mixture, 0.02 mol of isoquinoline was added and the mixture was shaken well for 5 h and kept as such for 24 h. Excess ethanol was removed through evaporation. A maroon-red pasty mass was obtained. This paste was digested with hot ethanol to obtain a maroon-red solid. The solid deposited at the bottom of the flask was filtered, powdered well using an agate mortar, washed again with 20 mL of dry ether and recrystallized from absolute alcohol. Good quality single crystals suitable for X-ray
were obtained by slow evaporation of ethanol at room temperature (yield: 80%; m.p. 413 K).7. Refinement
Crystal data, data collection and structure . The N-bound H atom was located in a difference Fourier map and refined isotropically. C-bound H atoms were positioned geometrically and refined as riding, with C—H = 0.93–0.96 Å and Uiso(H) = 1.2–1.5 Ueq(C).
details are summarized in Table 2Supporting information
CCDC reference: 1444879
https://doi.org/10.1107/S2056989016005004/cv5504sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989016005004/cv5504Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989016005004/cv5504Isup3.cml
Data collection: APEX2 (Bruker, 2004); cell
APEX2 and SAINT (Bruker, 2004); data reduction: SAINT and XPREP (Bruker, 2004); program(s) used to solve structure: SIR92 (Altomare et al., 1993); program(s) used to refine structure: SHELXL2014 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: SHELXL2014 (Sheldrick, 2015).C9H8N+·C12H9N4O7− | Dx = 1.471 Mg m−3 |
Mr = 451.40 | Mo Kα radiation, λ = 0.71073 Å |
Orthorhombic, P212121 | Cell parameters from 9400 reflections |
a = 7.5315 (3) Å | θ = 2.3–24.0° |
b = 15.5640 (8) Å | µ = 0.11 mm−1 |
c = 17.3901 (8) Å | T = 296 K |
V = 2038.47 (16) Å3 | Block, brown |
Z = 4 | 0.35 × 0.30 × 0.25 mm |
F(000) = 936 |
Bruker Kappa APEXII CCD diffractometer | 3588 independent reflections |
Radiation source: fine-focus sealed tube | 2797 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.038 |
ω and φ scan | θmax = 25.0°, θmin = 2.3° |
Absorption correction: multi-scan (SADABS; Bruker, 2004) | h = −8→8 |
Tmin = 0.958, Tmax = 0.984 | k = −18→18 |
27633 measured reflections | l = −20→20 |
Refinement on F2 | Hydrogen site location: mixed |
Least-squares matrix: full | H atoms treated by a mixture of independent and constrained refinement |
R[F2 > 2σ(F2)] = 0.055 | w = 1/[σ2(Fo2) + (0.0596P)2 + 2.2423P] where P = (Fo2 + 2Fc2)/3 |
wR(F2) = 0.164 | (Δ/σ)max < 0.001 |
S = 1.11 | Δρmax = 0.29 e Å−3 |
3588 reflections | Δρmin = −0.26 e Å−3 |
302 parameters | Absolute structure: Flack x determined using 1033 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons et al., 2013) |
0 restraints | Absolute structure parameter: 0.5 (4) |
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. The elements in the sample do not have sufficient anomalous scattering power for Mo(kα) radiation. Hence the Flack parameter and its standard deviation obtained from refinement have no physical significance. |
x | y | z | Uiso*/Ueq | ||
C1 | 1.0128 (8) | 0.1849 (4) | 0.6047 (3) | 0.0420 (13) | |
C2 | 0.9775 (8) | 0.1140 (3) | 0.5603 (3) | 0.0430 (13) | |
H2 | 0.9489 | 0.0617 | 0.5830 | 0.052* | |
C3 | 0.9850 (7) | 0.1217 (3) | 0.4818 (3) | 0.0380 (12) | |
C4 | 1.0322 (7) | 0.1979 (3) | 0.4434 (3) | 0.0360 (11) | |
C5 | 1.0660 (8) | 0.2679 (3) | 0.4922 (3) | 0.0443 (13) | |
H5 | 1.0970 | 0.3204 | 0.4705 | 0.053* | |
C6 | 1.0549 (8) | 0.2615 (4) | 0.5715 (3) | 0.0495 (14) | |
H6 | 1.0761 | 0.3094 | 0.6021 | 0.059* | |
C7 | 1.0594 (7) | 0.2047 (3) | 0.3605 (3) | 0.0337 (11) | |
C8 | 1.1510 (7) | 0.1402 (3) | 0.3218 (3) | 0.0357 (11) | |
C9 | 1.1333 (8) | 0.2196 (3) | 0.2030 (3) | 0.0421 (13) | |
C10 | 1.0069 (7) | 0.2807 (3) | 0.3207 (3) | 0.0388 (12) | |
C11 | 0.9855 (12) | 0.3574 (4) | 0.1982 (4) | 0.072 (2) | |
H11A | 0.9241 | 0.3963 | 0.2317 | 0.108* | |
H11B | 1.0872 | 0.3856 | 0.1766 | 0.108* | |
H11C | 0.9074 | 0.3396 | 0.1576 | 0.108* | |
C12 | 1.2891 (9) | 0.0820 (4) | 0.2065 (3) | 0.0569 (16) | |
H12A | 1.3142 | 0.0369 | 0.2426 | 0.085* | |
H12B | 1.2236 | 0.0590 | 0.1639 | 0.085* | |
H12C | 1.3985 | 0.1062 | 0.1884 | 0.085* | |
C13 | 1.4554 (8) | 0.0032 (4) | 0.5236 (3) | 0.0486 (14) | |
H13 | 1.4114 | 0.0499 | 0.5511 | 0.058* | |
C14 | 1.5694 (7) | −0.0536 (3) | 0.5585 (3) | 0.0404 (12) | |
C15 | 1.6326 (7) | −0.1244 (4) | 0.5152 (3) | 0.0449 (13) | |
C16 | 1.5786 (8) | −0.1322 (4) | 0.4383 (3) | 0.0522 (15) | |
H16 | 1.6195 | −0.1776 | 0.4084 | 0.063* | |
C17 | 1.4675 (8) | −0.0738 (4) | 0.4083 (3) | 0.0546 (15) | |
H17 | 1.4313 | −0.0788 | 0.3573 | 0.065* | |
C18 | 1.6259 (8) | −0.0443 (4) | 0.6357 (3) | 0.0554 (15) | |
H18 | 1.5888 | 0.0026 | 0.6647 | 0.066* | |
C19 | 1.7348 (9) | −0.1043 (6) | 0.6669 (4) | 0.069 (2) | |
H19 | 1.7689 | −0.0991 | 0.7181 | 0.083* | |
C20 | 1.7960 (10) | −0.1728 (5) | 0.6242 (4) | 0.074 (2) | |
H20 | 1.8716 | −0.2126 | 0.6471 | 0.088* | |
C21 | 1.7487 (9) | −0.1835 (4) | 0.5502 (4) | 0.0642 (18) | |
H21 | 1.7926 | −0.2298 | 0.5223 | 0.077* | |
N1 | 1.0035 (8) | 0.1760 (4) | 0.6875 (3) | 0.0628 (15) | |
N2 | 0.9243 (7) | 0.0456 (3) | 0.4385 (3) | 0.0496 (12) | |
N3 | 1.0427 (7) | 0.2826 (3) | 0.2415 (2) | 0.0435 (11) | |
N4 | 1.1845 (6) | 0.1485 (3) | 0.2441 (2) | 0.0389 (10) | |
N5 | 1.4081 (7) | −0.0079 (3) | 0.4514 (3) | 0.0508 (13) | |
O1 | 1.0316 (9) | 0.2406 (4) | 0.7261 (3) | 0.0887 (18) | |
O2 | 0.9721 (10) | 0.1063 (4) | 0.7153 (3) | 0.099 (2) | |
O3 | 0.8197 (6) | 0.0553 (3) | 0.3865 (3) | 0.0632 (12) | |
O4 | 0.9781 (7) | −0.0246 (3) | 0.4618 (3) | 0.0690 (14) | |
O5 | 0.9298 (6) | 0.3428 (3) | 0.3499 (2) | 0.0578 (11) | |
O6 | 1.1665 (7) | 0.2254 (3) | 0.1336 (2) | 0.0643 (12) | |
O7 | 1.2084 (6) | 0.0724 (2) | 0.3535 (2) | 0.0534 (11) | |
H5A | 1.330 (8) | 0.032 (4) | 0.431 (3) | 0.043 (15)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.050 (3) | 0.052 (3) | 0.025 (2) | 0.002 (3) | 0.002 (2) | −0.005 (2) |
C2 | 0.053 (3) | 0.039 (3) | 0.037 (3) | −0.001 (3) | −0.001 (3) | 0.005 (2) |
C3 | 0.042 (3) | 0.037 (3) | 0.035 (3) | −0.002 (2) | 0.000 (2) | −0.002 (2) |
C4 | 0.036 (3) | 0.039 (3) | 0.034 (3) | 0.002 (2) | −0.005 (2) | −0.003 (2) |
C5 | 0.050 (3) | 0.040 (3) | 0.044 (3) | 0.000 (3) | −0.004 (3) | 0.002 (2) |
C6 | 0.054 (3) | 0.051 (3) | 0.043 (3) | 0.002 (3) | −0.010 (3) | −0.018 (3) |
C7 | 0.041 (3) | 0.030 (2) | 0.030 (3) | −0.002 (2) | −0.004 (2) | 0.000 (2) |
C8 | 0.035 (3) | 0.039 (3) | 0.033 (3) | 0.000 (2) | −0.004 (2) | 0.002 (2) |
C9 | 0.047 (3) | 0.042 (3) | 0.038 (3) | −0.013 (3) | 0.001 (2) | 0.006 (2) |
C10 | 0.042 (3) | 0.032 (3) | 0.043 (3) | −0.004 (2) | −0.001 (2) | 0.002 (2) |
C11 | 0.108 (6) | 0.053 (4) | 0.054 (4) | 0.004 (4) | −0.006 (4) | 0.015 (3) |
C12 | 0.059 (4) | 0.065 (4) | 0.047 (3) | 0.008 (3) | 0.012 (3) | 0.000 (3) |
C13 | 0.048 (3) | 0.042 (3) | 0.055 (4) | 0.004 (3) | 0.003 (3) | −0.004 (3) |
C14 | 0.037 (3) | 0.039 (3) | 0.045 (3) | −0.002 (2) | 0.002 (2) | 0.004 (2) |
C15 | 0.039 (3) | 0.046 (3) | 0.049 (3) | 0.005 (3) | 0.002 (3) | 0.008 (3) |
C16 | 0.051 (3) | 0.052 (3) | 0.054 (4) | 0.007 (3) | 0.002 (3) | −0.011 (3) |
C17 | 0.055 (4) | 0.064 (4) | 0.045 (3) | −0.002 (3) | −0.006 (3) | 0.004 (3) |
C18 | 0.054 (4) | 0.063 (4) | 0.049 (4) | −0.006 (3) | −0.001 (3) | −0.004 (3) |
C19 | 0.053 (4) | 0.105 (6) | 0.049 (4) | −0.014 (4) | −0.013 (3) | 0.012 (4) |
C20 | 0.066 (4) | 0.082 (5) | 0.073 (5) | 0.019 (4) | −0.013 (4) | 0.021 (4) |
C21 | 0.062 (4) | 0.057 (4) | 0.074 (5) | 0.020 (3) | −0.007 (4) | 0.008 (3) |
N1 | 0.070 (4) | 0.081 (4) | 0.037 (3) | 0.018 (3) | −0.002 (3) | −0.004 (3) |
N2 | 0.057 (3) | 0.041 (3) | 0.051 (3) | −0.010 (2) | 0.009 (3) | −0.007 (2) |
N3 | 0.062 (3) | 0.033 (2) | 0.036 (2) | 0.002 (2) | −0.002 (2) | 0.0105 (19) |
N4 | 0.040 (2) | 0.042 (2) | 0.035 (2) | 0.003 (2) | 0.0034 (19) | 0.0010 (19) |
N5 | 0.051 (3) | 0.048 (3) | 0.054 (3) | 0.008 (2) | −0.008 (2) | 0.008 (3) |
O1 | 0.122 (5) | 0.099 (4) | 0.045 (3) | 0.009 (4) | −0.011 (3) | −0.026 (3) |
O2 | 0.158 (6) | 0.094 (4) | 0.046 (3) | −0.004 (4) | 0.003 (4) | 0.015 (3) |
O3 | 0.066 (3) | 0.065 (3) | 0.058 (3) | −0.014 (2) | −0.012 (2) | −0.016 (2) |
O4 | 0.099 (4) | 0.040 (2) | 0.068 (3) | −0.005 (2) | 0.012 (3) | −0.001 (2) |
O5 | 0.076 (3) | 0.044 (2) | 0.054 (2) | 0.010 (2) | −0.002 (2) | 0.006 (2) |
O6 | 0.086 (3) | 0.063 (3) | 0.044 (3) | −0.011 (3) | 0.009 (2) | 0.013 (2) |
O7 | 0.060 (3) | 0.055 (3) | 0.045 (2) | 0.017 (2) | 0.003 (2) | 0.007 (2) |
C1—C6 | 1.362 (8) | C12—H12A | 0.9600 |
C1—C2 | 1.372 (7) | C12—H12B | 0.9600 |
C1—N1 | 1.448 (7) | C12—H12C | 0.9600 |
C2—C3 | 1.372 (7) | C13—N5 | 1.316 (7) |
C2—H2 | 0.9300 | C13—C14 | 1.374 (8) |
C3—C4 | 1.406 (7) | C13—H13 | 0.9300 |
C3—N2 | 1.476 (7) | C14—C18 | 1.415 (8) |
C4—C5 | 1.404 (7) | C14—C15 | 1.418 (7) |
C4—C7 | 1.460 (7) | C15—C16 | 1.402 (8) |
C5—C6 | 1.385 (8) | C15—C21 | 1.408 (8) |
C5—H5 | 0.9300 | C16—C17 | 1.342 (8) |
C6—H6 | 0.9300 | C16—H16 | 0.9300 |
C7—C8 | 1.391 (7) | C17—N5 | 1.346 (8) |
C7—C10 | 1.425 (7) | C17—H17 | 0.9300 |
C8—O7 | 1.267 (6) | C18—C19 | 1.357 (10) |
C8—N4 | 1.381 (6) | C18—H18 | 0.9300 |
C9—O6 | 1.235 (6) | C19—C20 | 1.379 (10) |
C9—N3 | 1.369 (7) | C19—H19 | 0.9300 |
C9—N4 | 1.373 (7) | C20—C21 | 1.346 (10) |
C10—O5 | 1.236 (6) | C20—H20 | 0.9300 |
C10—N3 | 1.404 (7) | C21—H21 | 0.9300 |
C11—N3 | 1.452 (7) | N1—O2 | 1.211 (7) |
C11—H11A | 0.9600 | N1—O1 | 1.228 (8) |
C11—H11B | 0.9600 | N2—O3 | 1.209 (6) |
C11—H11C | 0.9600 | N2—O4 | 1.234 (6) |
C12—N4 | 1.455 (7) | N5—H5A | 0.93 (6) |
C6—C1—C2 | 120.6 (5) | N5—C13—C14 | 120.4 (5) |
C6—C1—N1 | 121.1 (5) | N5—C13—H13 | 119.8 |
C2—C1—N1 | 118.3 (5) | C14—C13—H13 | 119.8 |
C3—C2—C1 | 118.9 (5) | C13—C14—C18 | 122.8 (6) |
C3—C2—H2 | 120.6 | C13—C14—C15 | 118.3 (5) |
C1—C2—H2 | 120.6 | C18—C14—C15 | 118.9 (5) |
C2—C3—C4 | 123.8 (5) | C16—C15—C21 | 122.4 (6) |
C2—C3—N2 | 115.1 (5) | C16—C15—C14 | 118.5 (5) |
C4—C3—N2 | 120.9 (5) | C21—C15—C14 | 119.1 (6) |
C5—C4—C3 | 114.5 (5) | C17—C16—C15 | 119.5 (6) |
C5—C4—C7 | 121.0 (5) | C17—C16—H16 | 120.2 |
C3—C4—C7 | 124.4 (4) | C15—C16—H16 | 120.2 |
C6—C5—C4 | 122.3 (5) | C16—C17—N5 | 120.5 (6) |
C6—C5—H5 | 118.9 | C16—C17—H17 | 119.8 |
C4—C5—H5 | 118.9 | N5—C17—H17 | 119.8 |
C1—C6—C5 | 120.0 (5) | C19—C18—C14 | 119.5 (6) |
C1—C6—H6 | 120.0 | C19—C18—H18 | 120.3 |
C5—C6—H6 | 120.0 | C14—C18—H18 | 120.3 |
C8—C7—C10 | 120.1 (4) | C18—C19—C20 | 121.2 (6) |
C8—C7—C4 | 119.6 (4) | C18—C19—H19 | 119.4 |
C10—C7—C4 | 120.0 (4) | C20—C19—H19 | 119.4 |
O7—C8—N4 | 116.1 (4) | C21—C20—C19 | 121.5 (7) |
O7—C8—C7 | 124.1 (4) | C21—C20—H20 | 119.3 |
N4—C8—C7 | 119.8 (4) | C19—C20—H20 | 119.3 |
O6—C9—N3 | 121.8 (5) | C20—C21—C15 | 119.9 (7) |
O6—C9—N4 | 120.8 (5) | C20—C21—H21 | 120.1 |
N3—C9—N4 | 117.5 (4) | C15—C21—H21 | 120.1 |
O5—C10—N3 | 118.4 (5) | O2—N1—O1 | 123.3 (6) |
O5—C10—C7 | 125.4 (5) | O2—N1—C1 | 119.5 (6) |
N3—C10—C7 | 116.1 (5) | O1—N1—C1 | 117.2 (6) |
N3—C11—H11A | 109.5 | O3—N2—O4 | 124.8 (5) |
N3—C11—H11B | 109.5 | O3—N2—C3 | 118.9 (5) |
H11A—C11—H11B | 109.5 | O4—N2—C3 | 116.2 (5) |
N3—C11—H11C | 109.5 | C9—N3—C10 | 124.1 (4) |
H11A—C11—H11C | 109.5 | C9—N3—C11 | 117.9 (5) |
H11B—C11—H11C | 109.5 | C10—N3—C11 | 118.0 (5) |
N4—C12—H12A | 109.5 | C9—N4—C8 | 122.3 (4) |
N4—C12—H12B | 109.5 | C9—N4—C12 | 119.4 (4) |
H12A—C12—H12B | 109.5 | C8—N4—C12 | 118.2 (4) |
N4—C12—H12C | 109.5 | C13—N5—C17 | 122.8 (5) |
H12A—C12—H12C | 109.5 | C13—N5—H5A | 117 (3) |
H12B—C12—H12C | 109.5 | C17—N5—H5A | 121 (3) |
C6—C1—C2—C3 | −0.1 (9) | C13—C14—C18—C19 | 178.2 (6) |
N1—C1—C2—C3 | 179.7 (5) | C15—C14—C18—C19 | −1.8 (9) |
C1—C2—C3—C4 | 1.9 (9) | C14—C18—C19—C20 | 2.1 (10) |
C1—C2—C3—N2 | −172.9 (5) | C18—C19—C20—C21 | −0.8 (12) |
C2—C3—C4—C5 | −2.1 (8) | C19—C20—C21—C15 | −0.8 (11) |
N2—C3—C4—C5 | 172.5 (5) | C16—C15—C21—C20 | −180.0 (7) |
C2—C3—C4—C7 | 173.1 (5) | C14—C15—C21—C20 | 0.9 (9) |
N2—C3—C4—C7 | −12.4 (8) | C6—C1—N1—O2 | −177.3 (7) |
C3—C4—C5—C6 | 0.5 (8) | C2—C1—N1—O2 | 2.9 (10) |
C7—C4—C5—C6 | −174.8 (6) | C6—C1—N1—O1 | 1.3 (9) |
C2—C1—C6—C5 | −1.4 (9) | C2—C1—N1—O1 | −178.4 (6) |
N1—C1—C6—C5 | 178.9 (5) | C2—C3—N2—O3 | 131.3 (5) |
C4—C5—C6—C1 | 1.2 (9) | C4—C3—N2—O3 | −43.7 (8) |
C5—C4—C7—C8 | 132.9 (5) | C2—C3—N2—O4 | −44.6 (7) |
C3—C4—C7—C8 | −41.9 (8) | C4—C3—N2—O4 | 140.4 (5) |
C5—C4—C7—C10 | −41.3 (7) | O6—C9—N3—C10 | −177.7 (5) |
C3—C4—C7—C10 | 143.8 (5) | N4—C9—N3—C10 | 3.2 (8) |
C10—C7—C8—O7 | 177.1 (5) | O6—C9—N3—C11 | 0.2 (9) |
C4—C7—C8—O7 | 2.9 (8) | N4—C9—N3—C11 | −179.0 (6) |
C10—C7—C8—N4 | −2.6 (7) | O5—C10—N3—C9 | 177.3 (5) |
C4—C7—C8—N4 | −176.8 (5) | C7—C10—N3—C9 | −4.4 (8) |
C8—C7—C10—O5 | −177.8 (5) | O5—C10—N3—C11 | −0.5 (8) |
C4—C7—C10—O5 | −3.6 (8) | C7—C10—N3—C11 | 177.7 (5) |
C8—C7—C10—N3 | 4.0 (7) | O6—C9—N4—C8 | 179.4 (5) |
C4—C7—C10—N3 | 178.2 (5) | N3—C9—N4—C8 | −1.4 (8) |
N5—C13—C14—C18 | 179.4 (6) | O6—C9—N4—C12 | 4.0 (8) |
N5—C13—C14—C15 | −0.6 (8) | N3—C9—N4—C12 | −176.8 (5) |
C13—C14—C15—C16 | 1.2 (8) | O7—C8—N4—C9 | −178.5 (5) |
C18—C14—C15—C16 | −178.8 (5) | C7—C8—N4—C9 | 1.2 (7) |
C13—C14—C15—C21 | −179.7 (5) | O7—C8—N4—C12 | −3.1 (7) |
C18—C14—C15—C21 | 0.4 (8) | C7—C8—N4—C12 | 176.7 (5) |
C21—C15—C16—C17 | 179.9 (6) | C14—C13—N5—C17 | −0.3 (9) |
C14—C15—C16—C17 | −0.9 (9) | C16—C17—N5—C13 | 0.6 (9) |
C15—C16—C17—N5 | 0.1 (9) |
D—H···A | D—H | H···A | D···A | D—H···A |
N5—H5A···O7 | 0.93 (6) | 1.74 (6) | 2.592 (6) | 150 (5) |
C13—H13···O5i | 0.93 | 2.40 | 3.260 (7) | 153 |
C16—H16···O6ii | 0.93 | 2.33 | 3.187 (7) | 154 |
C17—H17···O2iii | 0.93 | 2.61 | 3.424 (8) | 146 |
Symmetry codes: (i) x+1/2, −y+1/2, −z+1; (ii) −x+3, y−1/2, −z+1/2; (iii) −x+5/2, −y, z−1/2. |
Acknowledgements
The authors are thankful to the DST for financial support, the SAIF, IIT Madras, Chennai − 36, for the single crystal XRD data collection and KMCH College of Pharmacy, Coimbatore, for the anticonvulsant activity results.
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