research communications
The crystal structures and Hirshfeld surface analysis of N′,N′′′-((1E,1′E)-{[methylenebis(oxy)]bis(6-bromo-3,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) dihydrate and N′,N′′′-((1E,1′E)-{[butane-1,4-diylbis(oxy)]bis(2,1-phenylene)}bis(methanylylidene))bis(isonicotinohydrazide) [+ solvent]
aPG & Research Department of Physics, The New College (Autonomous), Chennai 600 014, Tamil Nadu, India, bDepartment of Biophysics, All India Institute of Medical Sciences, New Delhi 110 029, India, and cDepartment of Inorganic Chemistry, University of Madras, Chennai 600 025, India
*Correspondence e-mail: mnizam.new@gmail.com
The title compounds, C27H20Br2N6O4·2H2O, (I), and C30H28N6O4·[+ solvent], (II), both crystallize with one half-molecule in the The whole molecule of (I) is generated by twofold rotation symmetry, with the twofold rotation axis bisecting the C atom of the –O—CH2—O– bridge. This results in a folded or U-shaped conformation of the molecule. The whole molecule of (II) is generated by inversion symmetry, with the central CH2—CH2 bond of the –O—(CH2)4—O– bridge being located about a center of inversion. This results in a step-like conformation of the molecule. The central C(=O)N—N=C regions of the isonicotinohydrazide moieties in both compounds are planar and the configuration about the imine C=N bonds is E. In compound (I), the benzene and pyridine rings are inclined to each other by 37.60 (6)°. The two symmetry-related pyridine rings are inclined to each other by 74.24 (6)°, and the two symmetry-related benzene rings by 7.69 (6)°. In compound (II), the benzene and pyridine rings are inclined to each other by 25.56 (11)°. The symmetry-related pyridine rings are parallel, as are the two symmetry-related benzene rings. In the crystal of (I), a pair of water molecules link the organic molecules via Owater—H⋯O and Owater—H⋯N hydrogen bonds, forming chains along [001], and enclosing an R42(8) and two R12(5) ring motifs. The chains are linked by N—H⋯Npyridine hydrogen bonds, forming a supramolecular framework. There are also a number of C—H⋯O hydrogen bonds, and C—H⋯π and offset π–π interactions [interplanar distance = 3.294 (1) Å] present reinforcing the framework. In the crystal of (II), molecules are linked by N—H⋯Npyridine hydrogen bonds, forming a supramolecular framework. Here too there are also a number of C—H⋯O hydrogen bonds present, and a C—H⋯π interaction, reinforcing the framework. For compound (II), a region of disordered electron density was corrected for using the SQUEEZE [Spek (2015). Acta Cryst. C71, 9–18] routine in PLATON. Their formula mass and unit-cell characteristics were not taken into account during refinement.
1. Chemical context
Hydrazide-hydrazone compounds are found to be associated with a wide spectrum of biological and medicinal applications. such as antimicrobial, anticonvulsant, analgesic, anti-inflammatory (Kaplancikli et al., 2012), anti-platelet, antibacterial, antifungal, anti-tubercular and anti-tumor properties (Babahan et al., 2013; Bedia et al., 2006). of the general type p-R′-C6H4—CH—N—C6H4—R"-p are well-known reagents that find practical application in various areas, e.g. photography and medicinal and pharmaceutical chemistry (Sethuram et al., 2013). Hydrazide Schiff base ligands arise owing to the presence of electron-donating nitrogen and oxygen atoms, allowing these to act as multidentate ligands, and their transition-metal complexes have been used in the treatment of tuberculosis, in colorimetric or fluorimetric analytic determinations, as well as in applications involving catalytic processes (Torje et al., 2012) and, in some cases, function as supramolecular building blocks in their molecular assemblies (Wei et al., 2015). Hydrazone derivatives containing an azomethine (–CONHN=CH–) group act as cytotoxic agents with the capability to prevent cell series in cancerous cells through different mechanisms (Patil et al., 2011). Pyridine heterocycles and their derivatives are present in many large molecules having photo-chemical, electrochemical and catalytic applications (Thirunavukkarsu et al., 2017; Venda et al., 2017; Jauhar et al., 2016; Babu et al., 2014a,b, 2015; Rajkumar et al., 2014, 2015; Huq et al., 2010). As a part of our research study, we report herein the synthesis and the crystal structures of the title compounds, (I) and (II), which contain several donor functions of a different nature: hydrazide and pyridine.
2. Structural commentary
The molecular structures of the title compounds (I) and (II) are illustrated in Figs. 1 and 2, respectively. Selected bond lengths and angles are given in Tables 1 and 2 for compounds (I) and (II), respectively. The conformations of the two molecules differ considerably. Compound (I) has a folded or U-shaped conformation, while compound (II) has an open step-like conformation. In compound (I), the benzene (C8–C13) and pyridine (N1/C1–C5) rings are inclined to each other by 37.60 (6)°. The two symmetry-related pyridine rings are inclined to each other by 74.24 (6)°, and the two symmetry-related benzene rings by 7.69 (6)°. In compound (II), the benzene and pyridine rings are inclined to each other by 25.56 (11)°. The symmetry-related pyridine rings are parallel, as are the two symmetry-related benzene rings. In both compounds, the hydrazone molecule adopts an E configuration with respect to the hydrazone bridge N3=C7, with torsion angle N2—N3—C7—C8 = 176.82 (11) ° in (I) and 179.5 (2)° in (II). On the other hand, torsion angles N3—N2—C6—C1 [−179.8 (1) ° for (I) and 171.5 (2)° for (II)] and C6—N2—N3—C7 [−173.8 (1) ° for (I) and 179.1 (2)° for (II)], are consistent with an all-trans relationship in the central chain.
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The bond lengths and angles in the carbohydrazide group of the title compounds can be compared with the values reported for related structures (Prabhu et al., 2011; Bikas et al., 2010). The N3—N2—C6—O1 torsion angle of 0.2 (2) and −5.6 (3)° for (I) and (II), respectively, indicates the cis configuration of the O1 atom with respect to the hydrazine nitrogen atom N3. The C6—N2 and C7=N3 bond lengths differ by 0.068 (2) Å in (I) and by 0.077 (2) Å in (II), hence these two bonds are properly assigned as single and double bonds, respectively. Bond lengths in the amide unit of aroyl are in the ranges 1.218–1.292 Å for C=O bonds and 1.313–1.365 Å for C—N bonds in the keto tautomeric form, and 1.284—1.314 Å for C=O bonds and 1.291–1.331 Å for C—N bonds in the enol tautomeric form (Hosseini-Monfared et al., 2013). Hence, compounds (I) and (II) are in the keto tautomeric form, which can be verified from the C=O and C—NH bond lengths of the amide unit: O1=C6 [1.230 (2) Å for (I) and 1.223 (2) Å for (II)] and N2—C6 [1.351 (2) Å for (I) and 1.355 (2) Å for (II)]. The bond distances C7=N3 [1.282 (2) Å for (I) and 1.278 (2) Å for (II)] and C6=O1 [1.229 (2) Å for (I) and 1.220 (2) Å for (II)], are very close to the recognized double C=N and C=O bond lengths (Prasanna et al., 2013; Wang et al., 2010), confirming that the carbohydrazide exists as an amido tautomer in the solid state. In the two compounds, the three bond angles around atom C6 (see Tables 1 and 2) differ from 120°, probably in order to decrease the repulsion between the lone pairs present on atoms N2 and O1.
3. Supramolecular features
In the crystal of (I), a pair of water molecules link the organic molecules via Owater—H⋯O and Owater—H⋯N hydrogen bonds, forming chains along [001] and enclosing an R42(8) and two R12(5) ring motifs (Table 3 and Fig. 3). The chains are linked by N—H⋯Npyridine hydrogen bonds, forming a supramolecular framework. There are also a number of C—H⋯O hydrogen bonds, and C—H⋯π and offset π–π interactions [interplanar distance = 3.294 (1) Å] present, reinforcing the framework (Table 3). The offset π-π- interactions involve inversion-related C8–C13 benzene rings, centroid Cg2. The intercentroid distance Cg2⋯Cg2(−x + 1, −y + 1, −z + 1) is 3.766 (1) Å, α = 0.00 (6)°, β = 29°, interplanar distance = 3.294 (1) Å, offset of 1.824 Å.
In the crystal of (II), molecules are linked by N—H⋯Npyridine hydrogen bonds, forming a supramolecular framework (Table 4 and Fig. 4). Here too there are also a number of C—H⋯O hydrogen bonds present, and a C—H⋯π interaction (Table 4), reinforcing the framework, but no π–π interactions are observed.
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For compound (II) a region of disordered electron density with a potential solvent-accessible void of volume 1220 Å3 with an electron count of 357 per was corrected for using the SQUEEZE routine in PLATON (Spek, 2015). The voids in the of (II) are illustrated in Fig. 4.
4. Hirshfeld surface analysis
The Hirshfeld surface analysis (Spackman & Jayatilaka, 2009), and the associated two-dimensional fingerprint plots (McKinnon et al., 2007), were calculated to analyse the intermolecular contacts in the crystals. The various calculations were performed with CrystalExplorer17 (Turner et al., 2017). The use of such calculations to analyse intermolecular contacts in crystals has been reported on recently by Tiekink and collaborators (Tan et al., 2019).
The Hirshfeld surfaces of compounds (I) and (II) mapped over dnorm are given in Figs. 5 and 6, respectively. For (I) the intermolecular contacts are illustrated in Fig. 7, and for (II) in Fig. 8. They are colour-mapped with the normalized contact distance, dnorm, from red (distances shorter than the sum of the van der Waals radii) through white to blue (distances longer than the sum of the van der Waals radii). The dnorm surface was mapped over a fixed colour scale of −0.512 (red) to 1.285 (blue) for compound (I) and −0.490 (red) to 4.945 (blue) for compound (II), where the red spots indicate the intermolecular contacts involved in hydrogen bonding (remembering that the disordered solvent in the channels of (II) have been SQUEEZED out).
The fingerprint plots are given in Figs. 9 and 10, for compounds (I) and (II), respectively. For compound (I), the principal intermolecular contacts are H⋯H at 28.9% (Fig. 9b), O⋯H/H⋯O at 13.8% (Fig. 9c), N⋯H/H⋯N at 11.3% (Fig. 9d), Br⋯H/H⋯Br at 14.3% (Fig. 9e) and C⋯H/H⋯C contacts at 13.6% (Fig. 9f). C⋯C contacts account for 8.4%, while C⋯Br are 3.0%, C⋯N are 3.0%, and finally C⋯O contacts amount to 1.4%.
For compound (II), the fingerprint plots reveal that the principal intermolecular contacts are H⋯H at 35.0% (Fig. 10b), O⋯H/H⋯O at 13.3% (Fig. 10c), N⋯H/H⋯N at 16.2% (Fig. 10d), and C⋯H/H⋯C at 33.6% (Fig. 10e). The remaining contacts are extremely weak, ca 1% each.
5. Database survey
A search of the Cambridge Structural Database (CSD, Version 5.40, February 2019; Groom et al., 2016) for compounds with an O atom in position 3 of the benzylidene ring, i.e. (3-OR-benzylidene)isonicotinohydrazide (R = C) skeleton gave 51 hits (supporting information file S1). The majority of these compounds were with an OMe or an OEt substituent.
A search for compounds with an O atom in position 2 of the benzylidene ring, i.e. (2-OR-benzylidene)isonicotinohydrazide (R = C) skeleton gave 23 hits (supporting information file S2). Again, the majority of these compounds have an OMe or an OEt substituent. However, here the most interesting and relevant compound concerns the ligand N′,N′′-[ethane-1,2-diylbis(oxy-2,1-phenylenemethylylidene)]bis(pyridine-4-carbohydrazide), in which a 1,2-dioxyethane bridge links two N′-benzylideneisonicotinohydrazide units. The crystal structures of two polymorphs have been described: a monoclinic P21 polymorph that crystallizes as a methanol disolvate (BAXLAQ; Mahmoudi et al., 2017) and a triclinic P polymorph (FIXJIG; Tai et al., 2004). The conformation of both compounds is U-shaped, similar to that of compound (I). The molecular structures of compounds (I), BAXLAQ and FIXJIG are compared in Fig. 11. The principal difference in the conformation of the three molecules is reflected in the dihedral angle involving the benzene rings, which are inclined to each other by 7.69 (6)° in (I), by 25.0 (2)° in BAXLAQ and by 55.27 (7)° in FIXJIG.
An interesting HgI2 complex of this ligand, bis(μ-{N′,N′′-[ethane-1,2-diylbis(oxy-2,1-phenylenemethylylidene)] bis(pyridine-4-carbohydrazide)})tetrakis(iodo)dimercury methanol disolvate (BAXKUJ; Mahmoudi et al., 2017), has a metallamacrocyclic architecture.
6. Synthesis and crystallization
Compound I: To 2-hydroxybenzaldehyde (5 mmol), in a 250 ml round-bottom (RB) flask was added DMF (30 ml) and potassium carbonate (12.5 mmol). The mixture was stirred at room temperature and then 1,1-diiodobutane (2.5 mmol) was added dropwise and the reaction mixture was stirred for 12 h. It was then partitioned between water and ethyl acetate. The ethyl acetate layer was collected and concentrated under reduced pressure. To 1,4-bis(2-carboxyaldehydephenoxy)butane (2 mmol) and isonicotinic acid hydrazide (4 mmol) in a 250 ml RB flask was added 100 ml of methanol and two drops of glacial acetic acid. The reaction mixture was stirred at room temperature and within 5 min a white-coloured product had formed. The reaction was continued for a further 30 min. The title compound was isolated by filtration and washed with methanol, then chloroform and followed by acetone. The final product was recrystallized using DMSO and yielded colourless block-like crystals of compound (I).
Compound I: To 5-bromo-2-hydroxybenzaldehyde (5 mmol), in a 250 ml RB flask, was added 50 ml of DMF and potassium carbonate (12.5 mmol). The mixture was stirred at room temperature and then 1,1-diiodomethane (2.5 mmol) was added dropwise. Then, the reaction mixture was stirred for 12 h. The product obtained was extracted in ethyl acetate medium. Methanol (100 ml) and two drops of glacial acetic acid were added to a mixture of 6,6′-[methylenebis(oxy)] bis(3-bromobenzaldehyde) (2 mmol) and isoniazid (4 mmol) in a 250 ml RB flask. The reaction mixture was stirred at room temperature and within 5 min a white-coloured product had formed and the reaction was continued for a further 30 min. The solid obtained was washed with methanol, then chloroform and followed by acetone. The final product was recrystallized using DMSO and yielded colourless block-like crystals of compound (II).
7. Refinement
Crystal data, data collection and structure . The NH H atoms for both compounds, and the water molecule H atoms for compound (I), were located in difference-Fourier maps and refined freely. For both compounds the C-bound H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms: C—H = 0.93-0.97 Å with Uiso(H) = 1.2Ueq(C).
details are summarized in Table 5
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For compound (II), a region of disordered electron density with a potential solvent accessible void of volume 1220 Å3 with an electron count of 357 per was corrected for using the SQUEEZE routine in PLATON (Spek, 2015). Their formula mass and unit-cell characteristics were not taken into account during refinement.
Supporting information
https://doi.org/10.1107/S2056989019005048/su5495sup1.cif
contains datablocks global, I, II. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S2056989019005048/su5495Isup4.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019005048/su5495Isup4.cml
Structure factors: contains datablock II. DOI: https://doi.org/10.1107/S2056989019005048/su5495IIsup5.hkl
Supporting information file. DOI: https://doi.org/10.1107/S2056989019005048/su5495IIsup5.cml
CSD search S1. DOI: https://doi.org/10.1107/S2056989019005048/su5495sup6.pdf
CSD Search S2. DOI: https://doi.org/10.1107/S2056989019005048/su5495sup7.pdf
For both structures, data collection: APEX2 (Bruker, 2008); cell
SAINT (Bruker, 2008); data reduction: SAINT (Bruker, 2008); program(s) used to solve structure: SHELXS2018 (Sheldrick, 2008); program(s) used to refine structure: SHELXL2018 (Sheldrick, 2015); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012) and Mercury (Macrae et al., 2008); software used to prepare material for publication: WinGX (Farrugia, 2012), publCIF (Westrip, 2010) and PLATON (Spek, 2009).C27H20Br2N6O4·2H2O | F(000) = 1384 |
Mr = 688.34 | Dx = 1.683 Mg m−3 |
Monoclinic, C2/c | Mo Kα radiation, λ = 0.71073 Å |
a = 15.1206 (2) Å | Cell parameters from 3387 reflections |
b = 10.1497 (2) Å | θ = 1.8–26.9° |
c = 18.0253 (3) Å | µ = 3.04 mm−1 |
β = 100.7960 (4)° | T = 293 K |
V = 2717.37 (8) Å3 | Block, colourless |
Z = 4 | 0.38 × 0.28 × 0.21 mm |
Bruker Kappa APEXII CCD diffractometer | 3202 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.033 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 28.4°, θmin = 2.8° |
Tmin = 0.499, Tmax = 0.746 | h = −20→20 |
29418 measured reflections | k = −13→13 |
3387 independent reflections | l = −24→24 |
Refinement on F2 | Secondary atom site location: difference Fourier map |
Least-squares matrix: full | Hydrogen site location: mixed |
R[F2 > 2σ(F2)] = 0.021 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.054 | w = 1/[σ2(Fo2) + (0.0247P)2 + 3.4271P] where P = (Fo2 + 2Fc2)/3 |
S = 1.05 | (Δ/σ)max = 0.002 |
3387 reflections | Δρmax = 0.49 e Å−3 |
199 parameters | Δρmin = −0.32 e Å−3 |
0 restraints | Extinction correction: (SHELXL2018; Sheldrick, 2015), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4 |
Primary atom site location: structure-invariant direct methods | Extinction coefficient: 0.00152 (17) |
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. |
x | y | z | Uiso*/Ueq | Occ. (<1) | |
Br1 | 0.70412 (2) | 0.52186 (2) | 0.47663 (2) | 0.01933 (6) | |
O1 | 0.45281 (7) | 1.00457 (9) | 0.61053 (6) | 0.0176 (2) | |
O2 | 0.45956 (6) | 0.35751 (9) | 0.68829 (5) | 0.01363 (18) | |
N1 | 0.22417 (8) | 1.19161 (11) | 0.75048 (7) | 0.0152 (2) | |
N2 | 0.41385 (7) | 0.82530 (10) | 0.67331 (6) | 0.0115 (2) | |
HN2 | 0.3760 (12) | 0.7919 (18) | 0.6974 (10) | 0.019 (4)* | |
N3 | 0.47208 (7) | 0.74664 (10) | 0.64190 (6) | 0.0120 (2) | |
C1 | 0.34534 (8) | 1.03494 (11) | 0.68973 (7) | 0.0105 (2) | |
C2 | 0.30431 (9) | 1.14287 (12) | 0.65037 (7) | 0.0125 (2) | |
H2 | 0.317244 | 1.165550 | 0.603561 | 0.015* | |
C3 | 0.24360 (9) | 1.21635 (13) | 0.68217 (7) | 0.0144 (2) | |
H3 | 0.214768 | 1.286668 | 0.654615 | 0.017* | |
C4 | 0.26812 (9) | 1.09117 (13) | 0.78941 (8) | 0.0160 (3) | |
H4 | 0.257654 | 1.074883 | 0.837801 | 0.019* | |
C5 | 0.32847 (9) | 1.00994 (12) | 0.76160 (8) | 0.0135 (2) | |
H5 | 0.356824 | 0.940616 | 0.790387 | 0.016* | |
C6 | 0.40899 (9) | 0.95414 (12) | 0.65410 (7) | 0.0111 (2) | |
C7 | 0.46797 (8) | 0.62336 (12) | 0.65637 (7) | 0.0105 (2) | |
H7 | 0.430077 | 0.593995 | 0.688011 | 0.013* | |
C8 | 0.52265 (8) | 0.52824 (12) | 0.62335 (7) | 0.0101 (2) | |
C9 | 0.51576 (8) | 0.39410 (12) | 0.63961 (7) | 0.0114 (2) | |
C10 | 0.55993 (9) | 0.29921 (13) | 0.60449 (8) | 0.0154 (3) | |
H10 | 0.552015 | 0.210250 | 0.613749 | 0.018* | |
C11 | 0.61571 (9) | 0.33760 (14) | 0.55570 (8) | 0.0164 (3) | |
H11 | 0.646693 | 0.275109 | 0.532790 | 0.020* | |
C12 | 0.62469 (9) | 0.47104 (13) | 0.54149 (7) | 0.0136 (2) | |
C13 | 0.57828 (8) | 0.56652 (13) | 0.57324 (7) | 0.0118 (2) | |
H13 | 0.583938 | 0.654965 | 0.561477 | 0.014* | |
C14 | 0.500000 | 0.27859 (17) | 0.750000 | 0.0157 (4) | |
H14A | 0.454724 | 0.222442 | 0.765344 | 0.019* | 0.5 |
H14B | 0.545278 | 0.222447 | 0.734654 | 0.019* | 0.5 |
O1W | 0.60456 (7) | 0.90764 (12) | 0.55169 (7) | 0.0256 (2) | |
H1W | 0.5551 (16) | 0.914 (2) | 0.5685 (12) | 0.037 (6)* | |
H2W | 0.5926 (16) | 0.934 (2) | 0.5072 (14) | 0.041 (6)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
Br1 | 0.01383 (9) | 0.03079 (10) | 0.01546 (8) | −0.00484 (5) | 0.00808 (5) | −0.00590 (5) |
O1 | 0.0203 (5) | 0.0125 (4) | 0.0235 (5) | 0.0021 (4) | 0.0133 (4) | 0.0048 (4) |
O2 | 0.0142 (4) | 0.0126 (4) | 0.0148 (4) | 0.0007 (3) | 0.0046 (3) | 0.0048 (3) |
N1 | 0.0150 (5) | 0.0127 (5) | 0.0192 (6) | −0.0003 (4) | 0.0067 (4) | −0.0031 (4) |
N2 | 0.0114 (5) | 0.0095 (5) | 0.0158 (5) | 0.0010 (4) | 0.0080 (4) | 0.0013 (4) |
N3 | 0.0116 (5) | 0.0108 (5) | 0.0147 (5) | 0.0021 (4) | 0.0052 (4) | −0.0003 (4) |
C1 | 0.0095 (6) | 0.0082 (5) | 0.0143 (6) | −0.0016 (4) | 0.0035 (4) | −0.0019 (4) |
C2 | 0.0138 (6) | 0.0123 (5) | 0.0115 (5) | 0.0001 (4) | 0.0024 (4) | −0.0008 (4) |
C3 | 0.0144 (6) | 0.0122 (5) | 0.0163 (6) | 0.0023 (5) | 0.0020 (5) | −0.0008 (5) |
C4 | 0.0204 (7) | 0.0135 (6) | 0.0167 (6) | −0.0017 (5) | 0.0099 (5) | −0.0003 (5) |
C5 | 0.0164 (6) | 0.0097 (5) | 0.0154 (6) | −0.0013 (4) | 0.0055 (5) | 0.0015 (4) |
C6 | 0.0104 (6) | 0.0106 (5) | 0.0125 (6) | 0.0000 (4) | 0.0027 (4) | 0.0000 (4) |
C7 | 0.0091 (5) | 0.0116 (5) | 0.0108 (5) | 0.0003 (4) | 0.0023 (4) | 0.0008 (4) |
C8 | 0.0080 (6) | 0.0104 (5) | 0.0112 (6) | 0.0006 (4) | 0.0003 (4) | 0.0000 (4) |
C9 | 0.0098 (6) | 0.0117 (5) | 0.0124 (5) | 0.0006 (4) | 0.0012 (4) | 0.0012 (4) |
C10 | 0.0176 (6) | 0.0112 (6) | 0.0169 (6) | 0.0028 (5) | 0.0020 (5) | −0.0006 (5) |
C11 | 0.0144 (6) | 0.0178 (6) | 0.0170 (6) | 0.0044 (5) | 0.0030 (5) | −0.0044 (5) |
C12 | 0.0087 (6) | 0.0211 (6) | 0.0118 (6) | −0.0007 (5) | 0.0036 (5) | −0.0018 (5) |
C13 | 0.0095 (6) | 0.0128 (5) | 0.0128 (6) | −0.0004 (4) | 0.0014 (4) | 0.0000 (4) |
C14 | 0.0271 (10) | 0.0076 (7) | 0.0118 (8) | 0.000 | 0.0019 (7) | 0.000 |
O1W | 0.0151 (5) | 0.0396 (7) | 0.0241 (6) | 0.0057 (5) | 0.0085 (4) | 0.0119 (5) |
Br1—C12 | 1.8978 (13) | C4—H4 | 0.9300 |
O1—C6 | 1.2300 (16) | C5—H5 | 0.9300 |
O2—C9 | 1.3818 (16) | C7—C8 | 1.4677 (17) |
O2—C14 | 1.4134 (13) | C7—H7 | 0.9300 |
N1—C4 | 1.3412 (18) | C8—C13 | 1.3997 (18) |
N1—C3 | 1.3421 (18) | C8—C9 | 1.4007 (17) |
N2—C6 | 1.3512 (16) | C9—C10 | 1.3904 (18) |
N2—N3 | 1.3857 (15) | C10—C11 | 1.384 (2) |
N2—HN2 | 0.851 (18) | C10—H10 | 0.9300 |
N3—C7 | 1.2820 (16) | C11—C12 | 1.3897 (19) |
C1—C2 | 1.3869 (17) | C11—H11 | 0.9300 |
C1—C5 | 1.3898 (18) | C12—C13 | 1.3818 (18) |
C1—C6 | 1.4976 (17) | C13—H13 | 0.9300 |
C2—C3 | 1.3873 (18) | C14—H14A | 0.9700 |
C2—H2 | 0.9300 | C14—H14B | 0.9700 |
C3—H3 | 0.9300 | O1W—H1W | 0.86 (2) |
C4—C5 | 1.3910 (19) | O1W—H2W | 0.83 (3) |
C9—O2—C14 | 115.16 (8) | C8—C7—H7 | 119.8 |
C4—N1—C3 | 116.75 (11) | C13—C8—C9 | 118.83 (12) |
C6—N2—N3 | 117.46 (11) | C13—C8—C7 | 122.10 (11) |
C6—N2—HN2 | 120.5 (12) | C9—C8—C7 | 119.00 (11) |
N3—N2—HN2 | 121.2 (12) | O2—C9—C10 | 120.53 (11) |
C7—N3—N2 | 114.86 (11) | O2—C9—C8 | 118.22 (11) |
C2—C1—C5 | 118.58 (12) | C10—C9—C8 | 121.14 (12) |
C2—C1—C6 | 118.36 (11) | C11—C10—C9 | 119.76 (12) |
C5—C1—C6 | 123.00 (11) | C11—C10—H10 | 120.1 |
C1—C2—C3 | 118.72 (12) | C9—C10—H10 | 120.1 |
C1—C2—H2 | 120.6 | C10—C11—C12 | 118.94 (12) |
C3—C2—H2 | 120.6 | C10—C11—H11 | 120.5 |
N1—C3—C2 | 123.64 (12) | C12—C11—H11 | 120.5 |
N1—C3—H3 | 118.2 | C13—C12—C11 | 122.17 (12) |
C2—C3—H3 | 118.2 | C13—C12—Br1 | 119.57 (10) |
N1—C4—C5 | 123.79 (13) | C11—C12—Br1 | 118.26 (10) |
N1—C4—H4 | 118.1 | C12—C13—C8 | 119.06 (12) |
C5—C4—H4 | 118.1 | C12—C13—H13 | 120.5 |
C1—C5—C4 | 118.37 (12) | C8—C13—H13 | 120.5 |
C1—C5—H5 | 120.8 | O2i—C14—O2 | 110.96 (14) |
C4—C5—H5 | 120.8 | O2i—C14—H14A | 109.4 |
O1—C6—N2 | 123.81 (12) | O2—C14—H14A | 109.4 |
O1—C6—C1 | 120.81 (11) | O2i—C14—H14B | 109.4 |
N2—C6—C1 | 115.38 (11) | O2—C14—H14B | 109.4 |
N3—C7—C8 | 120.47 (11) | H14A—C14—H14B | 108.0 |
N3—C7—H7 | 119.8 | H1W—O1W—H2W | 106 (2) |
C6—N2—N3—C7 | −173.82 (11) | N3—C7—C8—C9 | −179.26 (12) |
C5—C1—C2—C3 | −4.17 (18) | C14—O2—C9—C10 | 57.04 (16) |
C6—C1—C2—C3 | 178.46 (11) | C14—O2—C9—C8 | −126.67 (12) |
C4—N1—C3—C2 | 1.2 (2) | C13—C8—C9—O2 | −179.05 (11) |
C1—C2—C3—N1 | 2.3 (2) | C7—C8—C9—O2 | −2.05 (17) |
C3—N1—C4—C5 | −2.8 (2) | C13—C8—C9—C10 | −2.79 (18) |
C2—C1—C5—C4 | 2.71 (19) | C7—C8—C9—C10 | 174.21 (12) |
C6—C1—C5—C4 | 179.95 (12) | O2—C9—C10—C11 | 179.78 (11) |
N1—C4—C5—C1 | 0.9 (2) | C8—C9—C10—C11 | 3.60 (19) |
N3—N2—C6—O1 | 0.24 (19) | C9—C10—C11—C12 | −1.5 (2) |
N3—N2—C6—C1 | −179.82 (10) | C10—C11—C12—C13 | −1.4 (2) |
C2—C1—C6—O1 | 29.80 (18) | C10—C11—C12—Br1 | 178.26 (10) |
C5—C1—C6—O1 | −147.44 (13) | C11—C12—C13—C8 | 2.17 (19) |
C2—C1—C6—N2 | −150.15 (12) | Br1—C12—C13—C8 | −177.48 (9) |
C5—C1—C6—N2 | 32.61 (18) | C9—C8—C13—C12 | −0.08 (18) |
N2—N3—C7—C8 | 176.82 (11) | C7—C8—C13—C12 | −176.98 (11) |
N3—C7—C8—C13 | −2.37 (19) | C9—O2—C14—O2i | 87.86 (9) |
Symmetry code: (i) −x+1, y, −z+3/2. |
Cg1 is the centroid of N1/C1–C5 pyridine ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—HN2···N1ii | 0.85 (2) | 2.179 (19) | 3.0261 (16) | 174 (2) |
O1W—H1W···O1 | 0.86 (2) | 2.06 (2) | 2.8756 (15) | 158 (2) |
O1W—H1W···N3 | 0.86 (2) | 2.61 (2) | 3.2476 (16) | 131.3 (19) |
O1W—H2W···O1iii | 0.83 (3) | 2.19 (3) | 3.0244 (16) | 174 (2) |
C3—H3···O1Wiv | 0.93 | 2.56 | 3.4450 (17) | 159 |
C4—H4···Br1v | 0.93 | 2.94 | 3.8554 (13) | 169 |
C10—H10···O1vi | 0.93 | 2.56 | 3.4123 (17) | 152 |
C13—H13···O1W | 0.93 | 2.59 | 3.5148 (18) | 171 |
C14—H14A···Cg1vi | 0.97 | 2.74 | 3.594 (1) | 144 |
C14—H14B···Cg1vii | 0.97 | 2.74 | 3.594 (1) | 144 |
Symmetry codes: (ii) −x+1/2, y−1/2, −z+3/2; (iii) −x+1, −y+2, −z+1; (iv) x−1/2, y+1/2, z; (v) x−1/2, −y+3/2, z+1/2; (vi) x, y−1, z; (vii) −x+1, y−1, −z+3/2. |
C30H28N6O4[+solvent] | Dx = 1.159 Mg m−3 |
Mr = 536.58 | Mo Kα radiation, λ = 0.71073 Å |
Trigonal, R3:H | Cell parameters from 3792 reflections |
a = 34.3186 (2) Å | θ = 1.8–26.9° |
c = 6.7855 (3) Å | µ = 0.08 mm−1 |
V = 6921.0 (3) Å3 | T = 293 K |
Z = 9 | Block, colourless |
F(000) = 2538 | 0.30 × 0.25 × 0.20 mm |
Bruker Kappa APEXII CCD diffractometer | 2619 reflections with I > 2σ(I) |
ω and φ scans | Rint = 0.076 |
Absorption correction: multi-scan (SADABS; Bruker, 2008) | θmax = 28.3°, θmin = 2.1° |
Tmin = 0.630, Tmax = 0.746 | h = −45→36 |
22262 measured reflections | k = −29→45 |
3805 independent reflections | l = −9→9 |
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)] = 0.057 | Hydrogen site location: mixed |
wR(F2) = 0.142 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.05 | w = 1/[σ2(Fo2) + (0.0533P)2 + 11.1328P] where P = (Fo2 + 2Fc2)/3 |
3805 reflections | (Δ/σ)max < 0.001 |
185 parameters | Δρmax = 0.47 e Å−3 |
0 restraints | Δρmin = −0.34 e Å−3 |
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. |
x | y | z | Uiso*/Ueq | ||
O1 | 0.20009 (4) | 0.45231 (5) | 0.72823 (18) | 0.0262 (3) | |
O2 | 0.02621 (4) | 0.46026 (4) | 0.34035 (18) | 0.0214 (3) | |
N1 | 0.31092 (6) | 0.49292 (7) | 0.1812 (2) | 0.0346 (4) | |
N2 | 0.16142 (5) | 0.46016 (5) | 0.4732 (2) | 0.0218 (3) | |
H2N | 0.1653 (8) | 0.4749 (8) | 0.358 (3) | 0.033 (6)* | |
N3 | 0.12211 (5) | 0.44325 (5) | 0.5828 (2) | 0.0210 (3) | |
C1 | 0.23686 (6) | 0.47415 (6) | 0.4186 (3) | 0.0223 (4) | |
C2 | 0.27559 (8) | 0.47786 (10) | 0.4947 (3) | 0.0471 (7) | |
H2 | 0.277753 | 0.474161 | 0.629269 | 0.056* | |
C3 | 0.31139 (8) | 0.48705 (10) | 0.3729 (3) | 0.0480 (7) | |
H3 | 0.337126 | 0.489203 | 0.428924 | 0.058* | |
C4 | 0.27280 (9) | 0.48779 (11) | 0.1061 (3) | 0.0538 (8) | |
H4 | 0.271346 | 0.490922 | −0.029363 | 0.065* | |
C5 | 0.23528 (8) | 0.47810 (10) | 0.2170 (3) | 0.0457 (7) | |
H5 | 0.209289 | 0.474298 | 0.156458 | 0.055* | |
C6 | 0.19813 (6) | 0.46179 (6) | 0.5561 (3) | 0.0201 (4) | |
C7 | 0.08925 (6) | 0.44343 (6) | 0.4950 (3) | 0.0207 (4) | |
H7 | 0.093119 | 0.454627 | 0.367374 | 0.025* | |
C8 | 0.04564 (6) | 0.42628 (6) | 0.5923 (3) | 0.0197 (4) | |
C9 | 0.03514 (7) | 0.40109 (6) | 0.7662 (3) | 0.0240 (4) | |
H9 | 0.056366 | 0.395193 | 0.822447 | 0.029* | |
C10 | −0.00624 (7) | 0.38487 (7) | 0.8553 (3) | 0.0243 (4) | |
H10 | −0.012915 | 0.368208 | 0.970983 | 0.029* | |
C11 | −0.03787 (6) | 0.39371 (6) | 0.7700 (3) | 0.0216 (4) | |
H11 | −0.065758 | 0.382899 | 0.830143 | 0.026* | |
C12 | −0.02860 (6) | 0.41838 (6) | 0.5968 (3) | 0.0188 (4) | |
H12 | −0.050141 | 0.423846 | 0.540846 | 0.023* | |
C13 | 0.01323 (6) | 0.43478 (6) | 0.5082 (2) | 0.0177 (4) | |
C14 | −0.00685 (6) | 0.46611 (6) | 0.2364 (2) | 0.0178 (4) | |
H14A | −0.018719 | 0.480568 | 0.320625 | 0.021* | |
H14B | −0.031546 | 0.437179 | 0.195219 | 0.021* | |
C15 | 0.01615 (6) | 0.49521 (6) | 0.0585 (3) | 0.0186 (4) | |
H15A | 0.027315 | 0.480095 | −0.025658 | 0.022* | |
H15B | 0.041679 | 0.523411 | 0.101427 | 0.022* |
U11 | U22 | U33 | U12 | U13 | U23 | |
O1 | 0.0225 (7) | 0.0348 (8) | 0.0211 (6) | 0.0142 (6) | −0.0014 (5) | 0.0027 (6) |
O2 | 0.0183 (6) | 0.0283 (7) | 0.0212 (6) | 0.0143 (6) | −0.0004 (5) | 0.0057 (5) |
N1 | 0.0244 (9) | 0.0535 (12) | 0.0251 (9) | 0.0188 (9) | 0.0017 (7) | −0.0010 (8) |
N2 | 0.0211 (8) | 0.0262 (9) | 0.0211 (8) | 0.0142 (7) | 0.0002 (6) | 0.0028 (7) |
N3 | 0.0177 (8) | 0.0254 (8) | 0.0232 (8) | 0.0132 (7) | 0.0008 (6) | 0.0005 (6) |
C1 | 0.0206 (9) | 0.0237 (9) | 0.0228 (9) | 0.0113 (8) | −0.0012 (7) | −0.0003 (7) |
C2 | 0.0322 (12) | 0.094 (2) | 0.0212 (10) | 0.0365 (14) | 0.0023 (9) | 0.0105 (12) |
C3 | 0.0279 (12) | 0.092 (2) | 0.0276 (11) | 0.0325 (13) | −0.0028 (9) | 0.0021 (12) |
C4 | 0.0447 (15) | 0.110 (2) | 0.0207 (10) | 0.0492 (17) | 0.0037 (10) | 0.0085 (13) |
C5 | 0.0340 (13) | 0.087 (2) | 0.0291 (11) | 0.0399 (14) | −0.0010 (10) | 0.0054 (12) |
C6 | 0.0206 (9) | 0.0199 (9) | 0.0205 (9) | 0.0108 (8) | −0.0020 (7) | −0.0010 (7) |
C7 | 0.0232 (9) | 0.0244 (10) | 0.0186 (8) | 0.0149 (8) | −0.0006 (7) | 0.0017 (7) |
C8 | 0.0202 (9) | 0.0204 (9) | 0.0206 (8) | 0.0118 (8) | −0.0023 (7) | −0.0034 (7) |
C9 | 0.0255 (10) | 0.0283 (10) | 0.0233 (9) | 0.0174 (9) | −0.0037 (8) | 0.0000 (8) |
C10 | 0.0298 (10) | 0.0259 (10) | 0.0203 (9) | 0.0162 (9) | 0.0024 (8) | 0.0045 (8) |
C11 | 0.0204 (9) | 0.0228 (9) | 0.0223 (9) | 0.0113 (8) | 0.0009 (7) | −0.0027 (7) |
C12 | 0.0178 (9) | 0.0194 (9) | 0.0206 (8) | 0.0103 (7) | −0.0043 (7) | −0.0043 (7) |
C13 | 0.0204 (9) | 0.0169 (8) | 0.0172 (8) | 0.0103 (7) | −0.0024 (7) | −0.0027 (7) |
C14 | 0.0157 (8) | 0.0215 (9) | 0.0193 (8) | 0.0116 (7) | −0.0022 (7) | −0.0004 (7) |
C15 | 0.0173 (9) | 0.0198 (9) | 0.0199 (8) | 0.0102 (8) | −0.0011 (7) | −0.0003 (7) |
O1—C6 | 1.223 (2) | C7—C8 | 1.463 (3) |
O2—C13 | 1.368 (2) | C7—H7 | 0.9300 |
O2—C14 | 1.433 (2) | C8—C9 | 1.399 (3) |
N1—C3 | 1.318 (3) | C8—C13 | 1.405 (2) |
N1—C4 | 1.331 (3) | C9—C10 | 1.379 (3) |
N2—C6 | 1.355 (2) | C9—H9 | 0.9300 |
N2—N3 | 1.388 (2) | C10—C11 | 1.391 (3) |
N2—H2N | 0.91 (2) | C10—H10 | 0.9300 |
N3—C7 | 1.278 (2) | C11—C12 | 1.389 (3) |
C1—C2 | 1.371 (3) | C11—H11 | 0.9300 |
C1—C5 | 1.379 (3) | C12—C13 | 1.390 (2) |
C1—C6 | 1.501 (3) | C12—H12 | 0.9300 |
C2—C3 | 1.380 (3) | C14—C15 | 1.513 (2) |
C2—H2 | 0.9300 | C14—H14A | 0.9700 |
C3—H3 | 0.9300 | C14—H14B | 0.9700 |
C4—C5 | 1.381 (3) | C15—C15i | 1.527 (3) |
C4—H4 | 0.9300 | C15—H15A | 0.9700 |
C5—H5 | 0.9300 | C15—H15B | 0.9700 |
C13—O2—C14 | 118.16 (13) | C13—C8—C7 | 119.36 (16) |
C3—N1—C4 | 116.33 (19) | C10—C9—C8 | 120.95 (17) |
C6—N2—N3 | 118.93 (15) | C10—C9—H9 | 119.5 |
C6—N2—H2N | 117.6 (15) | C8—C9—H9 | 119.5 |
N3—N2—H2N | 122.5 (15) | C9—C10—C11 | 119.22 (17) |
C7—N3—N2 | 115.07 (15) | C9—C10—H10 | 120.4 |
C2—C1—C5 | 116.64 (18) | C11—C10—H10 | 120.4 |
C2—C1—C6 | 118.21 (17) | C12—C11—C10 | 121.25 (17) |
C5—C1—C6 | 124.87 (17) | C12—C11—H11 | 119.4 |
C1—C2—C3 | 120.44 (19) | C10—C11—H11 | 119.4 |
C1—C2—H2 | 119.8 | C11—C12—C13 | 119.25 (17) |
C3—C2—H2 | 119.8 | C11—C12—H12 | 120.4 |
N1—C3—C2 | 123.3 (2) | C13—C12—H12 | 120.4 |
N1—C3—H3 | 118.4 | O2—C13—C12 | 124.04 (16) |
C2—C3—H3 | 118.4 | O2—C13—C8 | 115.63 (15) |
N1—C4—C5 | 124.1 (2) | C12—C13—C8 | 120.32 (16) |
N1—C4—H4 | 118.0 | O2—C14—C15 | 107.28 (13) |
C5—C4—H4 | 118.0 | O2—C14—H14A | 110.3 |
C1—C5—C4 | 119.1 (2) | C15—C14—H14A | 110.3 |
C1—C5—H5 | 120.4 | O2—C14—H14B | 110.3 |
C4—C5—H5 | 120.4 | C15—C14—H14B | 110.3 |
O1—C6—N2 | 124.00 (17) | H14A—C14—H14B | 108.5 |
O1—C6—C1 | 120.65 (16) | C14—C15—C15i | 111.20 (18) |
N2—C6—C1 | 115.29 (15) | C14—C15—H15A | 109.4 |
N3—C7—C8 | 121.04 (16) | C15i—C15—H15A | 109.4 |
N3—C7—H7 | 119.5 | C14—C15—H15B | 109.4 |
C8—C7—H7 | 119.5 | C15i—C15—H15B | 109.4 |
C9—C8—C13 | 119.01 (17) | H15A—C15—H15B | 108.0 |
C9—C8—C7 | 121.63 (16) | ||
C6—N2—N3—C7 | 179.08 (17) | N3—C7—C8—C13 | 167.81 (17) |
C5—C1—C2—C3 | 2.7 (4) | C13—C8—C9—C10 | −0.3 (3) |
C6—C1—C2—C3 | 176.9 (2) | C7—C8—C9—C10 | −179.49 (17) |
C4—N1—C3—C2 | −2.6 (4) | C8—C9—C10—C11 | 0.2 (3) |
C1—C2—C3—N1 | 0.3 (5) | C9—C10—C11—C12 | 0.2 (3) |
C3—N1—C4—C5 | 1.8 (4) | C10—C11—C12—C13 | −0.5 (3) |
C2—C1—C5—C4 | −3.4 (4) | C14—O2—C13—C12 | −7.6 (2) |
C6—C1—C5—C4 | −177.2 (2) | C14—O2—C13—C8 | 173.57 (15) |
N1—C4—C5—C1 | 1.2 (5) | C11—C12—C13—O2 | −178.45 (16) |
N3—N2—C6—O1 | −5.6 (3) | C11—C12—C13—C8 | 0.4 (3) |
N3—N2—C6—C1 | 171.51 (15) | C9—C8—C13—O2 | 178.94 (16) |
C2—C1—C6—O1 | −4.9 (3) | C7—C8—C13—O2 | −1.8 (2) |
C5—C1—C6—O1 | 168.8 (2) | C9—C8—C13—C12 | 0.0 (3) |
C2—C1—C6—N2 | 177.9 (2) | C7—C8—C13—C12 | 179.25 (16) |
C5—C1—C6—N2 | −8.4 (3) | C13—O2—C14—C15 | −179.86 (14) |
N2—N3—C7—C8 | 179.54 (15) | O2—C14—C15—C15i | −178.00 (17) |
N3—C7—C8—C9 | −13.0 (3) |
Symmetry code: (i) −x, −y+1, −z. |
Cg2 is the centroid of the C8–C13 benzene ring. |
D—H···A | D—H | H···A | D···A | D—H···A |
N2—H2N···N1ii | 0.91 (2) | 2.04 (2) | 2.907 (2) | 159 (2) |
C3—H3···O1iii | 0.93 | 2.60 | 3.449 (3) | 153 |
C3—H3···N3iii | 0.93 | 2.55 | 3.223 (3) | 129 |
C7—H7···N1ii | 0.93 | 2.63 | 3.372 (3) | 137 |
C12—H12···O1iv | 0.93 | 2.43 | 3.331 (2) | 163 |
C15—H15A···Cg2v | 0.97 | 2.91 | 3.748 (2) | 145 |
Symmetry codes: (ii) y−1/3, −x+y+1/3, −z+1/3; (iii) x−y+2/3, x+1/3, −z+4/3; (iv) −y+1/3, x−y+2/3, z−1/3; (v) x, y, z−1. |
Acknowledgements
The authors are grateful to the SAIF, IIT, Madras, India, for the data collection.
References
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