organic compounds
2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-4-methoxybenzylidene]pyridine-4-carbohydrazide (2/1)
a'Vinča' Institute of Nuclear Sciences, Laboratory of Theoretical Physics and Condensed Matter Physics, University of Belgrade, PO Box 522, 11001 Belgrade, Serbia, bManchester Metropolitan University, Chemistry and Environmental Division, Manchester M1 5GD, England, cKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq, and dChemistry Department, Tikrit University, Tikrit, Iraq
*Correspondence e-mail: snovak@vin.bg.ac.rs
In the 10H7NO4·C14H13N3O2, the two independent acid molecules are connected through strong O—H⋯N and O—H⋯O hydrogen bonds to the central molecule of the antitubercular drug N′-[(E)-4-methoxybenzylidene]pyridine-4-carbohydrazide. Two such trimolecular units related by an inversion centre interact through a pair of N—H⋯O hydrogen bonds, forming a 3 + 3 molecular aggregate. The dihedral angle between the aromatic rings of the hydrazone molecule is 1.99 (12)°. The crystal packing features weak C—H⋯O and π–π stacking interactions, with centroid–centroid distances of 3.8460 (19) and 3.8703 (13) Å.
of the title compound, 2CRelated literature
For anti-tuberculosis drugs containing the isoniazid core structure, see: Bijev (2006); Imramovský et al. (2007); Maccari et al. (2005); Schultheiss & Newman (2009); Shindikar & Viswanathan (2005); Sinha et al. (2005). For crystal structures with N′-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide, see: Jing et al. (2005); Lin & Liu (2007); Shanmuga Sundara Raj et al. (1999); Wardell et al. (2007). For crystal structures with 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Barooah et al. (2006); Feeder & Jones (1994, 1996). For a related see: Mohamed et al. (2012). For the synthesis of 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Rajpurohit & Sah (2005).
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).
Supporting information
https://doi.org/10.1107/S1600536812038032/rz2799sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812038032/rz2799Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812038032/rz2799Isup3.cml
The cocrystallized solid (I) was obtained unintentionally from a reaction of 0.01 mol (2.55 g) of N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide with 0.02 mol (4.10 g) of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid in 50 ml ethanol. The reaction mixture was heated for 6 h at 351 K, then poured on crushed ice (50 g). The resulting solid was filtered off, washed with cold ethanol and recrystallized from ethanol. Yellow crystals suitable for X-ray
were grown up in a diluted ethanolic solution over two days. M.p. 472- 474 K. Crystals of the title compound can also be obtained by a simple crystallization of two components dissolved in ethanol.2-(1,3-Dioxoisoindolin-2-yl)acetic acid was prepared according to the literature procedure (Rajpurohit & Sah, 2005). N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide was prepared by the reaction of an equimolar solution of isoniazid (0.01 mol; 1.37 g) and p-methoxybenzaldehyde (0.01 mol; 1.21 g) in ethanol. The reaction mixture was heated at 351 K and monitored by TLC until completed after 4 h, then left at fume cupboard where the solvent evaporated. The resulting solid was recrystallized from ethanol in a very good yield (87%); m.p. 435–437 K.
H atoms bonded to C atoms were placed at calculated positions, with C—H distances fixed at 0.93 Å for aromatic C(sp2) atoms and at 0.96 and 0.97 Å for methyl and methylene C(sp3) atoms, respectively. The corresponding isotropic displacement parameters of the H atoms were set equal to 1.2Ueq or 1.5Ueq of the parent C(sp2) or C(sp3) atoms, respectively. A rotating model was employed for the methyl group. The H atoms attached to N and O atoms were located in a difference Fourier map and refined isotropically.
Compounds incorporating the isoniazid (INH) core structure have shown high inhibitory activity in vitro (Bijev, 2006; Imramovský et al., 2007) and in mice towards M. tuberculosis H37Rv, ATCC 27294, M. tuberculosis clinical isolates and isoniazid-resistant M. tuberculosis (Maccari et al., 2005; Schultheiss & Newman 2009; Shindikar & Viswanathan, 2005; Sinha et al., 2005). In the present study we report the
of a novel, tricomponent cocrystal (I) containing the isoniazid-related hydrazone N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide and 2-(1,3-dioxoisoindolin-2-yl)acetic acid in a 1:2 molar ratio.The
of (I) contains one hydrazone molecule and two crystallographically independent molecules of the acid denoted as A and B in Fig. 1. The A and B molecules tightly connect to the hydrazone via short and directional O2a—H1Oa···N1 and O2b— H1Ob···O1 hydrogen bond, respectively (Table 1). The interactions of A and B molecules significantly differ as their carboxyl acid groups, serving as proton donors, find different acceptors within the hydrazone molecule i.e. pyridinyl N1 and carboxyl O1 (Fig. 1). The interaction O2a—H1Oa···N1 which directly involves the acidic –COOH group and the most basic pyridinyl N1 atom causes the noticeable elongation of O2—H1Oa bond in molecule A (Table 1), yet no proton transfer occurs and all components remain neutral.Besides the different engagement in the strongest interactions, the important difference between molecules A and B concerns their conformation. Thus the O1 carbonyl atom adopts trans and cis orientation relating to N1 atom in A and B. In addition, the O1—C1—C2—N1 torsion angle is 161.2 (2) and 1.4 (2)°, in molecules A and B respectively. It is worth mentioning that in a previously reported cocrystal (Mohamed et al., 2012) as well as in the crystal structures of 2-(1,3-dioxoisoindolin-2-yl)acetic acid containing one molecule in the
(Feeder & Jones, 1996), two independent molecules (Barooah et al., 2006) or the same molecule as monohydrate (Feeder & Jones, 1994), the value of the corresponding torsion angle O1—C1—C2—N1 is below 15.8° indicating the preferred conformation is similar to that of molecule B.There are several crystal structures of hydrazone N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide describing this compound as monohydrate crystallizing in two forms, monoclinic (Jing et al., 2005; Shanmuga Sundara Raj et al., 1999; Wardell et al., 2007) and orthorhombic (Lin & Liu, 2007). The present form of the molecule shows no particular difference in bond lengths and angles in comparison to the previous ones.
The above described trimer with strongly intermolecular hydrogen-bonded components (Fig. 1), undergoes further arrangement via much weaker interamolecular interactions. Two such trimolecular units related by an inversion centre interact through a pair of N2—H1N2···O4b hydrogen bonds (Table 1) forming a 3 + 3 molecular aggregate.
Apart from this classical N—H···O hydrogen bond, the arrangement of the molecules in the cocrystal is further based on weak C— H···O (Table 1) and π–π interactions. Figure 2 displays the three-dimensional crystal packing as viewed down the a axis. The molecules of hydrazone are stacked in the ac plane with the perpendicular interplanar distances of 3.44 [for molecule at (-x, -y + 2, -z + 1)] and 3.46 Å [for molecule at (-x + 1, -y + 2, -z + 1)]. On the other hand, the acid molecules arrange along the c axis in an AABBAABB sequence, with the perpendicular distances between the rings ranging from 3.31 to 3.43 Å. Considering only the six membered aromatic rings one can observe only a modest overlap: Cg1···Cg2 (-x, -y + 2, -z + 1) = 3.8460 (10) Å, where Cg1 and Cg2 are the centroids of the N1—C5 and C8—C13 rings, respectively and Cg4···Cg4 (x + 1/2, -y + 1, -z) 3.8703 (13) Å where Cg4 is the centroid of the C4a—C9a ring.
For anti-tuberculosis drugs containing the isoniazid core structure, see: Bijev (2006); Imramovský et al. (2007); Maccari et al. (2005); Schultheiss & Newman (2009); Shindikar & Viswanathan (2005); Sinha et al. (2005). For crystal structures with N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide, see: Jing et al. (2005); Lin & Liu (2007); Shanmuga Sundara Raj et al. (1999); Wardell et al. (2007). For crystal structures with 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Barooah et al. (2006); Feeder & Jones (1994, 1996). For a related
see: Mohamed et al. (2012). For the synthesis of 2-(1,3-dioxoisoindolin-2-yl)acetic acid, see: Rajpurohit & Sah (2005).Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell
CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).Fig. 1. The molecular structure of the title compound with displacement ellipsoids drawn at the 35% probability level. Intermolecular hydrogen interactions are shown as dashed bonds. | |
Fig. 2. Crystal packing of the title compound, showing the stacking arrangement of the components within the unit cell. |
2C10H7NO4·C14H13N3O2 | Z = 2 |
Mr = 665.61 | F(000) = 692 |
Triclinic, P1 | Dx = 1.441 Mg m−3 |
Hall symbol: -P 1 | Cu Kα radiation, λ = 1.54184 Å |
a = 8.1238 (4) Å | Cell parameters from 3871 reflections |
b = 12.7963 (7) Å | θ = 3.0–72.3° |
c = 15.9191 (11) Å | µ = 0.91 mm−1 |
α = 105.590 (5)° | T = 293 K |
β = 101.160 (5)° | Prismatic, yellow |
γ = 97.535 (4)° | 0.16 × 0.10 × 0.08 mm |
V = 1534.19 (17) Å3 |
Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer | 5912 independent reflections |
Radiation source: Enhance (Cu) X-ray Source | 4836 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.022 |
Detector resolution: 16.3280 pixels mm-1 | θmax = 72.5°, θmin = 3.0° |
ω scans | h = −6→9 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | k = −15→15 |
Tmin = 0.963, Tmax = 1.000 | l = −19→19 |
10334 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)] = 0.040 | H atoms treated by a mixture of independent and constrained refinement |
wR(F2) = 0.116 | w = 1/[σ2(Fo2) + (0.0523P)2 + 0.272P] where P = (Fo2 + 2Fc2)/3 |
S = 1.06 | (Δ/σ)max = 0.001 |
5912 reflections | Δρmax = 0.28 e Å−3 |
456 parameters | Δρmin = −0.21 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: 0.0024 (3) |
2C10H7NO4·C14H13N3O2 | γ = 97.535 (4)° |
Mr = 665.61 | V = 1534.19 (17) Å3 |
Triclinic, P1 | Z = 2 |
a = 8.1238 (4) Å | Cu Kα radiation |
b = 12.7963 (7) Å | µ = 0.91 mm−1 |
c = 15.9191 (11) Å | T = 293 K |
α = 105.590 (5)° | 0.16 × 0.10 × 0.08 mm |
β = 101.160 (5)° |
Oxford Diffraction Xcalibur (Sapphire3, Gemini) diffractometer | 5912 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) | 4836 reflections with I > 2σ(I) |
Tmin = 0.963, Tmax = 1.000 | Rint = 0.022 |
10334 measured reflections |
R[F2 > 2σ(F2)] = 0.040 | 0 restraints |
wR(F2) = 0.116 | H atoms treated by a mixture of independent and constrained refinement |
S = 1.06 | Δρmax = 0.28 e Å−3 |
5912 reflections | Δρmin = −0.21 e Å−3 |
456 parameters |
Experimental. Absorption correction: Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. 'CrysAlisPro, (Oxford Diffraction, 2009)' |
x | y | z | Uiso*/Ueq | ||
C1 | −0.2642 (2) | 0.95037 (14) | 0.17010 (12) | 0.0549 (4) | |
H1 | −0.3093 | 0.9940 | 0.1368 | 0.066* | |
C2 | −0.1425 (2) | 1.00139 (13) | 0.24952 (11) | 0.0493 (4) | |
H2 | −0.1069 | 1.0778 | 0.2689 | 0.059* | |
C3 | −0.07405 (18) | 0.93782 (11) | 0.30007 (9) | 0.0366 (3) | |
C4 | −0.1314 (2) | 0.82441 (12) | 0.26761 (11) | 0.0451 (4) | |
H4 | −0.0881 | 0.7786 | 0.2992 | 0.054* | |
C5 | −0.2535 (2) | 0.78039 (13) | 0.18774 (11) | 0.0508 (4) | |
H5 | −0.2915 | 0.7041 | 0.1667 | 0.061* | |
C6 | 0.05450 (18) | 0.99688 (11) | 0.38761 (9) | 0.0367 (3) | |
C7 | 0.33689 (19) | 0.92085 (12) | 0.54388 (10) | 0.0401 (3) | |
H7 | 0.3112 | 0.8449 | 0.5156 | 0.048* | |
C8 | 0.46634 (18) | 0.96649 (12) | 0.62817 (9) | 0.0384 (3) | |
C9 | 0.5239 (2) | 1.08025 (13) | 0.66447 (11) | 0.0495 (4) | |
H9 | 0.4785 | 1.1271 | 0.6346 | 0.059* | |
C10 | 0.6462 (2) | 1.12434 (13) | 0.74335 (12) | 0.0534 (4) | |
H10 | 0.6852 | 1.2005 | 0.7656 | 0.064* | |
C11 | 0.7124 (2) | 1.05611 (13) | 0.79041 (10) | 0.0440 (3) | |
C12 | 0.6576 (2) | 0.94290 (13) | 0.75570 (11) | 0.0479 (4) | |
H12 | 0.7014 | 0.8965 | 0.7865 | 0.057* | |
C13 | 0.5365 (2) | 0.89881 (13) | 0.67442 (11) | 0.0455 (4) | |
H13 | 0.5017 | 0.8225 | 0.6505 | 0.055* | |
C14 | 0.8949 (3) | 1.04657 (17) | 0.92371 (12) | 0.0657 (5) | |
H14A | 0.8023 | 1.0151 | 0.9443 | 0.099* | |
H14B | 0.9823 | 1.0934 | 0.9744 | 0.099* | |
H14C | 0.9415 | 0.9884 | 0.8901 | 0.099* | |
N1 | −0.31974 (17) | 0.84128 (11) | 0.13922 (9) | 0.0491 (3) | |
N2 | 0.13864 (16) | 0.93389 (10) | 0.42826 (8) | 0.0406 (3) | |
N3 | 0.25843 (15) | 0.98456 (10) | 0.50851 (8) | 0.0406 (3) | |
O1 | 0.07630 (14) | 1.09815 (8) | 0.41843 (7) | 0.0474 (3) | |
O2 | 0.83335 (17) | 1.11023 (10) | 0.86773 (8) | 0.0597 (3) | |
C1A | −0.5342 (2) | 0.78299 (14) | −0.07334 (12) | 0.0535 (4) | |
C2A | −0.6544 (2) | 0.71923 (15) | −0.16347 (11) | 0.0555 (4) | |
H2A1 | −0.6875 | 0.7711 | −0.1952 | 0.067* | |
H2A2 | −0.5940 | 0.6709 | −0.1989 | 0.067* | |
C3A | −0.8216 (2) | 0.54517 (13) | −0.15390 (10) | 0.0475 (4) | |
C4A | −0.9875 (2) | 0.51700 (15) | −0.13116 (11) | 0.0511 (4) | |
C5A | −1.0643 (3) | 0.42141 (17) | −0.11908 (12) | 0.0647 (5) | |
H5A | −1.0149 | 0.3590 | −0.1273 | 0.078* | |
C6A | −1.2187 (3) | 0.4222 (2) | −0.09410 (14) | 0.0840 (7) | |
H6A | −1.2740 | 0.3594 | −0.0848 | 0.101* | |
C7A | −1.2915 (3) | 0.5161 (3) | −0.08276 (16) | 0.0940 (9) | |
H7A | −1.3951 | 0.5146 | −0.0660 | 0.113* | |
C8A | −1.2142 (3) | 0.6116 (3) | −0.09567 (15) | 0.0828 (7) | |
H8A | −1.2638 | 0.6739 | −0.0882 | 0.099* | |
C9A | −1.0608 (2) | 0.61061 (17) | −0.11997 (11) | 0.0585 (5) | |
C10A | −0.9459 (2) | 0.69870 (15) | −0.13613 (11) | 0.0569 (4) | |
N1A | −0.80682 (17) | 0.65359 (11) | −0.15608 (9) | 0.0493 (3) | |
O1A | −0.4285 (3) | 0.85939 (17) | −0.06654 (12) | 0.1289 (9) | |
O2A | −0.55221 (17) | 0.74356 (11) | −0.00883 (8) | 0.0626 (4) | |
O3A | −0.71648 (17) | 0.48833 (10) | −0.16856 (10) | 0.0637 (3) | |
O4A | −0.9621 (2) | 0.79203 (12) | −0.13410 (10) | 0.0829 (5) | |
C1B | 0.40479 (19) | 1.30491 (12) | 0.57084 (10) | 0.0425 (3) | |
C2B | 0.5016 (2) | 1.37468 (13) | 0.66499 (10) | 0.0454 (4) | |
H2B1 | 0.4301 | 1.4222 | 0.6920 | 0.054* | |
H2B2 | 0.5286 | 1.3267 | 0.7015 | 0.054* | |
C3B | 0.67039 (19) | 1.55202 (12) | 0.66280 (10) | 0.0405 (3) | |
C4B | 0.83781 (19) | 1.58248 (12) | 0.64317 (10) | 0.0395 (3) | |
C5B | 0.9136 (2) | 1.67982 (13) | 0.63322 (11) | 0.0470 (4) | |
H5B | 0.8603 | 1.7406 | 0.6396 | 0.056* | |
C6B | 1.0719 (2) | 1.68341 (15) | 0.61333 (12) | 0.0538 (4) | |
H6B | 1.1261 | 1.7478 | 0.6059 | 0.065* | |
C7B | 1.1523 (2) | 1.59280 (16) | 0.60421 (11) | 0.0544 (4) | |
H7B | 1.2594 | 1.5979 | 0.5913 | 0.065* | |
C8B | 1.0751 (2) | 1.49488 (14) | 0.61414 (11) | 0.0492 (4) | |
H8B | 1.1285 | 1.4342 | 0.6082 | 0.059* | |
C9B | 0.91670 (19) | 1.49099 (12) | 0.63309 (9) | 0.0401 (3) | |
C10B | 0.7997 (2) | 1.39932 (12) | 0.64460 (10) | 0.0422 (3) | |
N1B | 0.65796 (16) | 1.44176 (10) | 0.66338 (9) | 0.0422 (3) | |
O1B | 0.45570 (17) | 1.30518 (12) | 0.50517 (8) | 0.0671 (4) | |
O2B | 0.26246 (15) | 1.24440 (9) | 0.57228 (8) | 0.0516 (3) | |
O3B | 0.56253 (15) | 1.60611 (10) | 0.67685 (9) | 0.0556 (3) | |
O4B | 0.81814 (16) | 1.30561 (9) | 0.63963 (8) | 0.0569 (3) | |
H1OA | −0.464 (3) | 0.784 (2) | 0.0486 (18) | 0.101 (8)* | |
H1OB | 0.210 (3) | 1.1927 (18) | 0.5169 (16) | 0.078 (7)* | |
H1N2 | 0.126 (2) | 0.8633 (16) | 0.4029 (13) | 0.056 (5)* |
U11 | U22 | U33 | U12 | U13 | U23 | |
C1 | 0.0628 (11) | 0.0486 (9) | 0.0472 (9) | 0.0083 (8) | −0.0060 (8) | 0.0194 (7) |
C2 | 0.0578 (10) | 0.0374 (8) | 0.0453 (9) | 0.0048 (7) | −0.0030 (7) | 0.0135 (7) |
C3 | 0.0358 (7) | 0.0373 (7) | 0.0347 (7) | 0.0062 (6) | 0.0053 (6) | 0.0102 (6) |
C4 | 0.0475 (9) | 0.0371 (7) | 0.0457 (8) | 0.0063 (6) | −0.0004 (7) | 0.0135 (6) |
C5 | 0.0539 (9) | 0.0381 (8) | 0.0491 (9) | 0.0017 (7) | −0.0016 (7) | 0.0077 (7) |
C6 | 0.0367 (7) | 0.0350 (7) | 0.0358 (7) | 0.0037 (6) | 0.0059 (6) | 0.0098 (6) |
C7 | 0.0418 (8) | 0.0365 (7) | 0.0397 (8) | 0.0067 (6) | 0.0058 (6) | 0.0110 (6) |
C8 | 0.0379 (7) | 0.0409 (8) | 0.0365 (7) | 0.0083 (6) | 0.0067 (6) | 0.0129 (6) |
C9 | 0.0550 (9) | 0.0395 (8) | 0.0492 (9) | 0.0098 (7) | −0.0045 (7) | 0.0169 (7) |
C10 | 0.0605 (10) | 0.0387 (8) | 0.0508 (9) | 0.0060 (7) | −0.0050 (8) | 0.0112 (7) |
C11 | 0.0446 (8) | 0.0473 (8) | 0.0365 (8) | 0.0084 (7) | 0.0030 (6) | 0.0117 (6) |
C12 | 0.0550 (9) | 0.0477 (9) | 0.0421 (8) | 0.0130 (7) | 0.0021 (7) | 0.0207 (7) |
C13 | 0.0522 (9) | 0.0382 (8) | 0.0437 (8) | 0.0076 (7) | 0.0047 (7) | 0.0138 (6) |
C14 | 0.0744 (13) | 0.0714 (12) | 0.0439 (10) | 0.0109 (10) | −0.0080 (9) | 0.0223 (9) |
N1 | 0.0493 (8) | 0.0489 (8) | 0.0396 (7) | 0.0038 (6) | −0.0030 (6) | 0.0103 (6) |
N2 | 0.0432 (7) | 0.0340 (6) | 0.0364 (6) | 0.0068 (5) | −0.0026 (5) | 0.0063 (5) |
N3 | 0.0396 (6) | 0.0400 (6) | 0.0358 (6) | 0.0054 (5) | −0.0006 (5) | 0.0088 (5) |
O1 | 0.0505 (6) | 0.0348 (5) | 0.0468 (6) | 0.0030 (4) | −0.0050 (5) | 0.0100 (5) |
O2 | 0.0673 (8) | 0.0539 (7) | 0.0438 (6) | 0.0057 (6) | −0.0126 (5) | 0.0126 (5) |
C1A | 0.0593 (10) | 0.0482 (9) | 0.0460 (9) | −0.0015 (8) | 0.0067 (8) | 0.0126 (7) |
C2A | 0.0667 (11) | 0.0522 (9) | 0.0428 (9) | 0.0047 (8) | 0.0062 (8) | 0.0147 (7) |
C3A | 0.0489 (9) | 0.0448 (8) | 0.0397 (8) | 0.0092 (7) | −0.0003 (7) | 0.0055 (7) |
C4A | 0.0451 (9) | 0.0580 (10) | 0.0373 (8) | 0.0054 (7) | −0.0017 (7) | 0.0034 (7) |
C5A | 0.0617 (11) | 0.0676 (12) | 0.0490 (10) | −0.0037 (9) | 0.0045 (8) | 0.0058 (9) |
C6A | 0.0640 (13) | 0.1115 (19) | 0.0524 (12) | −0.0225 (13) | 0.0051 (10) | 0.0102 (12) |
C7A | 0.0479 (12) | 0.154 (3) | 0.0619 (14) | 0.0113 (15) | 0.0099 (10) | 0.0095 (15) |
C8A | 0.0557 (12) | 0.121 (2) | 0.0680 (14) | 0.0321 (13) | 0.0120 (10) | 0.0173 (13) |
C9A | 0.0498 (10) | 0.0750 (12) | 0.0404 (9) | 0.0219 (9) | −0.0015 (7) | 0.0044 (8) |
C10A | 0.0659 (11) | 0.0573 (10) | 0.0384 (8) | 0.0239 (9) | −0.0017 (8) | 0.0038 (7) |
N1A | 0.0500 (8) | 0.0448 (7) | 0.0424 (7) | 0.0095 (6) | −0.0027 (6) | 0.0053 (6) |
O1A | 0.1529 (18) | 0.1220 (15) | 0.0688 (10) | −0.0829 (14) | −0.0089 (11) | 0.0354 (10) |
O2A | 0.0641 (8) | 0.0649 (8) | 0.0428 (7) | −0.0146 (6) | −0.0080 (6) | 0.0175 (6) |
O3A | 0.0600 (8) | 0.0566 (7) | 0.0794 (9) | 0.0226 (6) | 0.0205 (7) | 0.0204 (7) |
O4A | 0.1137 (13) | 0.0643 (9) | 0.0734 (10) | 0.0459 (9) | 0.0155 (9) | 0.0164 (7) |
C1B | 0.0432 (8) | 0.0369 (7) | 0.0429 (8) | 0.0079 (6) | 0.0024 (6) | 0.0103 (6) |
C2B | 0.0483 (9) | 0.0400 (8) | 0.0426 (8) | 0.0018 (6) | 0.0056 (7) | 0.0108 (6) |
C3B | 0.0431 (8) | 0.0367 (7) | 0.0374 (7) | 0.0087 (6) | 0.0009 (6) | 0.0096 (6) |
C4B | 0.0410 (8) | 0.0365 (7) | 0.0358 (7) | 0.0082 (6) | 0.0000 (6) | 0.0085 (6) |
C5B | 0.0493 (9) | 0.0408 (8) | 0.0484 (9) | 0.0073 (7) | 0.0037 (7) | 0.0155 (7) |
C6B | 0.0514 (9) | 0.0533 (9) | 0.0506 (9) | −0.0018 (7) | 0.0043 (7) | 0.0170 (8) |
C7B | 0.0390 (8) | 0.0720 (11) | 0.0448 (9) | 0.0057 (8) | 0.0031 (7) | 0.0130 (8) |
C8B | 0.0434 (8) | 0.0551 (9) | 0.0424 (8) | 0.0167 (7) | 0.0002 (7) | 0.0076 (7) |
C9B | 0.0411 (8) | 0.0378 (7) | 0.0333 (7) | 0.0088 (6) | −0.0035 (6) | 0.0057 (6) |
C10B | 0.0465 (8) | 0.0359 (7) | 0.0356 (7) | 0.0095 (6) | −0.0036 (6) | 0.0056 (6) |
N1B | 0.0421 (7) | 0.0339 (6) | 0.0445 (7) | 0.0049 (5) | 0.0015 (5) | 0.0092 (5) |
O1B | 0.0629 (8) | 0.0824 (9) | 0.0427 (7) | −0.0045 (7) | 0.0081 (6) | 0.0092 (6) |
O2B | 0.0517 (7) | 0.0436 (6) | 0.0470 (6) | −0.0037 (5) | 0.0027 (5) | 0.0058 (5) |
O3B | 0.0522 (7) | 0.0508 (7) | 0.0704 (8) | 0.0220 (5) | 0.0183 (6) | 0.0208 (6) |
O4B | 0.0673 (8) | 0.0347 (6) | 0.0633 (7) | 0.0158 (5) | 0.0027 (6) | 0.0124 (5) |
C1—N1 | 1.332 (2) | C3A—N1A | 1.387 (2) |
C1—C2 | 1.380 (2) | C3A—C4A | 1.486 (2) |
C1—H1 | 0.9300 | C4A—C5A | 1.377 (3) |
C2—C3 | 1.384 (2) | C4A—C9A | 1.391 (3) |
C2—H2 | 0.9300 | C5A—C6A | 1.388 (3) |
C3—C4 | 1.384 (2) | C5A—H5A | 0.9300 |
C3—C6 | 1.5058 (19) | C6A—C7A | 1.392 (4) |
C4—C5 | 1.378 (2) | C6A—H6A | 0.9300 |
C4—H4 | 0.9300 | C7A—C8A | 1.384 (4) |
C5—N1 | 1.329 (2) | C7A—H7A | 0.9300 |
C5—H5 | 0.9300 | C8A—C9A | 1.375 (3) |
C6—O1 | 1.2312 (17) | C8A—H8A | 0.9300 |
C6—N2 | 1.3376 (19) | C9A—C10A | 1.477 (3) |
C7—N3 | 1.2775 (19) | C10A—O4A | 1.211 (2) |
C7—C8 | 1.456 (2) | C10A—N1A | 1.386 (2) |
C7—H7 | 0.9300 | O2A—H1OA | 1.00 (3) |
C8—C13 | 1.388 (2) | C1B—O1B | 1.197 (2) |
C8—C9 | 1.392 (2) | C1B—O2B | 1.3123 (19) |
C9—C10 | 1.368 (2) | C1B—C2B | 1.517 (2) |
C9—H9 | 0.9300 | C2B—N1B | 1.445 (2) |
C10—C11 | 1.390 (2) | C2B—H2B1 | 0.9700 |
C10—H10 | 0.9300 | C2B—H2B2 | 0.9700 |
C11—O2 | 1.3619 (18) | C3B—O3B | 1.2036 (18) |
C11—C12 | 1.381 (2) | C3B—N1B | 1.4038 (18) |
C12—C13 | 1.389 (2) | C3B—C4B | 1.480 (2) |
C12—H12 | 0.9300 | C4B—C5B | 1.378 (2) |
C13—H13 | 0.9300 | C4B—C9B | 1.394 (2) |
C14—O2 | 1.425 (2) | C5B—C6B | 1.381 (2) |
C14—H14A | 0.9600 | C5B—H5B | 0.9300 |
C14—H14B | 0.9600 | C6B—C7B | 1.391 (3) |
C14—H14C | 0.9600 | C6B—H6B | 0.9300 |
N2—N3 | 1.3811 (16) | C7B—C8B | 1.388 (2) |
N2—H1N2 | 0.87 (2) | C7B—H7B | 0.9300 |
C1A—O1A | 1.180 (2) | C8B—C9B | 1.375 (2) |
C1A—O2A | 1.284 (2) | C8B—H8B | 0.9300 |
C1A—C2A | 1.516 (2) | C9B—C10B | 1.484 (2) |
C2A—N1A | 1.446 (2) | C10B—O4B | 1.2114 (18) |
C2A—H2A1 | 0.9700 | C10B—N1B | 1.386 (2) |
C2A—H2A2 | 0.9700 | O2B—H1OB | 0.93 (2) |
C3A—O3A | 1.2090 (19) | ||
N1—C1—C2 | 122.73 (15) | C5A—C4A—C9A | 122.03 (18) |
N1—C1—H1 | 118.6 | C5A—C4A—C3A | 130.83 (17) |
C2—C1—H1 | 118.6 | C9A—C4A—C3A | 107.11 (16) |
C1—C2—C3 | 119.45 (15) | C4A—C5A—C6A | 117.2 (2) |
C1—C2—H2 | 120.3 | C4A—C5A—H5A | 121.4 |
C3—C2—H2 | 120.3 | C6A—C5A—H5A | 121.4 |
C4—C3—C2 | 117.70 (14) | C5A—C6A—C7A | 120.7 (2) |
C4—C3—C6 | 124.47 (13) | C5A—C6A—H6A | 119.7 |
C2—C3—C6 | 117.81 (13) | C7A—C6A—H6A | 119.7 |
C5—C4—C3 | 119.02 (14) | C8A—C7A—C6A | 121.9 (2) |
C5—C4—H4 | 120.5 | C8A—C7A—H7A | 119.1 |
C3—C4—H4 | 120.5 | C6A—C7A—H7A | 119.1 |
N1—C5—C4 | 123.38 (15) | C9A—C8A—C7A | 117.3 (2) |
N1—C5—H5 | 118.3 | C9A—C8A—H8A | 121.4 |
C4—C5—H5 | 118.3 | C7A—C8A—H8A | 121.4 |
O1—C6—N2 | 123.53 (13) | C8A—C9A—C4A | 121.0 (2) |
O1—C6—C3 | 119.79 (13) | C8A—C9A—C10A | 130.3 (2) |
N2—C6—C3 | 116.68 (12) | C4A—C9A—C10A | 108.63 (16) |
N3—C7—C8 | 120.32 (13) | O4A—C10A—N1A | 124.2 (2) |
N3—C7—H7 | 119.8 | O4A—C10A—C9A | 129.96 (19) |
C8—C7—H7 | 119.8 | N1A—C10A—C9A | 105.85 (15) |
C13—C8—C9 | 118.05 (14) | C10A—N1A—C3A | 112.07 (15) |
C13—C8—C7 | 121.51 (14) | C10A—N1A—C2A | 122.47 (15) |
C9—C8—C7 | 120.44 (13) | C3A—N1A—C2A | 124.74 (14) |
C10—C9—C8 | 121.12 (14) | C1A—O2A—H1OA | 112.8 (14) |
C10—C9—H9 | 119.4 | O1B—C1B—O2B | 125.65 (15) |
C8—C9—H9 | 119.4 | O1B—C1B—C2B | 123.35 (15) |
C9—C10—C11 | 120.42 (15) | O2B—C1B—C2B | 110.99 (14) |
C9—C10—H10 | 119.8 | N1B—C2B—C1B | 111.00 (13) |
C11—C10—H10 | 119.8 | N1B—C2B—H2B1 | 109.4 |
O2—C11—C12 | 125.81 (14) | C1B—C2B—H2B1 | 109.4 |
O2—C11—C10 | 114.62 (14) | N1B—C2B—H2B2 | 109.4 |
C12—C11—C10 | 119.54 (14) | C1B—C2B—H2B2 | 109.4 |
C11—C12—C13 | 119.55 (14) | H2B1—C2B—H2B2 | 108.0 |
C11—C12—H12 | 120.2 | O3B—C3B—N1B | 124.21 (15) |
C13—C12—H12 | 120.2 | O3B—C3B—C4B | 130.12 (14) |
C8—C13—C12 | 121.27 (14) | N1B—C3B—C4B | 105.68 (12) |
C8—C13—H13 | 119.4 | C5B—C4B—C9B | 121.58 (15) |
C12—C13—H13 | 119.4 | C5B—C4B—C3B | 130.30 (14) |
O2—C14—H14A | 109.5 | C9B—C4B—C3B | 108.11 (13) |
O2—C14—H14B | 109.5 | C4B—C5B—C6B | 117.23 (15) |
H14A—C14—H14B | 109.5 | C4B—C5B—H5B | 121.4 |
O2—C14—H14C | 109.5 | C6B—C5B—H5B | 121.4 |
H14A—C14—H14C | 109.5 | C5B—C6B—C7B | 121.48 (16) |
H14B—C14—H14C | 109.5 | C5B—C6B—H6B | 119.3 |
C5—N1—C1 | 117.72 (14) | C7B—C6B—H6B | 119.3 |
C6—N2—N3 | 118.70 (12) | C8B—C7B—C6B | 121.01 (16) |
C6—N2—H1N2 | 121.2 (13) | C8B—C7B—H7B | 119.5 |
N3—N2—H1N2 | 119.8 (12) | C6B—C7B—H7B | 119.5 |
C7—N3—N2 | 116.20 (12) | C9B—C8B—C7B | 117.49 (15) |
C11—O2—C14 | 117.57 (14) | C9B—C8B—H8B | 121.3 |
O1A—C1A—O2A | 124.36 (17) | C7B—C8B—H8B | 121.3 |
O1A—C1A—C2A | 120.76 (17) | C8B—C9B—C4B | 121.20 (15) |
O2A—C1A—C2A | 114.78 (15) | C8B—C9B—C10B | 130.71 (14) |
N1A—C2A—C1A | 113.27 (14) | C4B—C9B—C10B | 108.08 (13) |
N1A—C2A—H2A1 | 108.9 | O4B—C10B—N1B | 124.78 (15) |
C1A—C2A—H2A1 | 108.9 | O4B—C10B—C9B | 129.25 (15) |
N1A—C2A—H2A2 | 108.9 | N1B—C10B—C9B | 105.98 (12) |
C1A—C2A—H2A2 | 108.9 | C10B—N1B—C3B | 112.14 (13) |
H2A1—C2A—H2A2 | 107.7 | C10B—N1B—C2B | 123.63 (13) |
O3A—C3A—N1A | 124.53 (16) | C3B—N1B—C2B | 123.10 (13) |
O3A—C3A—C4A | 129.13 (16) | C1B—O2B—H1OB | 112.4 (14) |
N1A—C3A—C4A | 106.33 (14) | ||
N1—C1—C2—C3 | 0.0 (3) | C3A—C4A—C9A—C10A | 0.63 (18) |
C1—C2—C3—C4 | 0.4 (2) | C8A—C9A—C10A—O4A | −2.3 (3) |
C1—C2—C3—C6 | −178.24 (15) | C4A—C9A—C10A—O4A | 179.28 (18) |
C2—C3—C4—C5 | −0.5 (2) | C8A—C9A—C10A—N1A | 178.19 (19) |
C6—C3—C4—C5 | 178.00 (15) | C4A—C9A—C10A—N1A | −0.28 (18) |
C3—C4—C5—N1 | 0.3 (3) | O4A—C10A—N1A—C3A | −179.81 (16) |
C4—C3—C6—O1 | −167.66 (15) | C9A—C10A—N1A—C3A | −0.21 (18) |
C2—C3—C6—O1 | 10.8 (2) | O4A—C10A—N1A—C2A | 9.5 (3) |
C4—C3—C6—N2 | 11.7 (2) | C9A—C10A—N1A—C2A | −170.92 (14) |
C2—C3—C6—N2 | −169.80 (14) | O3A—C3A—N1A—C10A | −179.69 (16) |
N3—C7—C8—C13 | 170.94 (14) | C4A—C3A—N1A—C10A | 0.59 (17) |
N3—C7—C8—C9 | −9.4 (2) | O3A—C3A—N1A—C2A | −9.2 (3) |
C13—C8—C9—C10 | 0.1 (3) | C4A—C3A—N1A—C2A | 171.05 (14) |
C7—C8—C9—C10 | −179.63 (16) | C1A—C2A—N1A—C10A | 80.2 (2) |
C8—C9—C10—C11 | −1.8 (3) | C1A—C2A—N1A—C3A | −89.3 (2) |
C9—C10—C11—O2 | 179.91 (16) | O1B—C1B—C2B—N1B | 1.4 (2) |
C9—C10—C11—C12 | 1.8 (3) | O2B—C1B—C2B—N1B | −179.70 (12) |
O2—C11—C12—C13 | −178.07 (16) | O3B—C3B—C4B—C5B | −2.0 (3) |
C10—C11—C12—C13 | −0.2 (3) | N1B—C3B—C4B—C5B | 178.67 (15) |
C9—C8—C13—C12 | 1.5 (2) | O3B—C3B—C4B—C9B | 179.29 (16) |
C7—C8—C13—C12 | −178.76 (15) | N1B—C3B—C4B—C9B | −0.02 (16) |
C11—C12—C13—C8 | −1.5 (3) | C9B—C4B—C5B—C6B | −0.4 (2) |
C4—C5—N1—C1 | 0.0 (3) | C3B—C4B—C5B—C6B | −178.94 (15) |
C2—C1—N1—C5 | −0.1 (3) | C4B—C5B—C6B—C7B | −0.4 (2) |
O1—C6—N2—N3 | −1.0 (2) | C5B—C6B—C7B—C8B | 0.5 (3) |
C3—C6—N2—N3 | 179.68 (12) | C6B—C7B—C8B—C9B | 0.1 (2) |
C8—C7—N3—N2 | 179.59 (13) | C7B—C8B—C9B—C4B | −0.9 (2) |
C6—N2—N3—C7 | −179.03 (13) | C7B—C8B—C9B—C10B | 177.81 (15) |
C12—C11—O2—C14 | −8.0 (3) | C5B—C4B—C9B—C8B | 1.0 (2) |
C10—C11—O2—C14 | 174.13 (16) | C3B—C4B—C9B—C8B | 179.88 (13) |
O1A—C1A—C2A—N1A | −161.2 (2) | C5B—C4B—C9B—C10B | −177.90 (13) |
O2A—C1A—C2A—N1A | 22.3 (2) | C3B—C4B—C9B—C10B | 0.93 (16) |
O3A—C3A—C4A—C5A | 1.4 (3) | C8B—C9B—C10B—O4B | −0.1 (3) |
N1A—C3A—C4A—C5A | −178.94 (17) | C4B—C9B—C10B—O4B | 178.70 (15) |
O3A—C3A—C4A—C9A | 179.55 (17) | C8B—C9B—C10B—N1B | 179.68 (15) |
N1A—C3A—C4A—C9A | −0.75 (17) | C4B—C9B—C10B—N1B | −1.50 (16) |
C9A—C4A—C5A—C6A | −0.7 (3) | O4B—C10B—N1B—C3B | −178.65 (14) |
C3A—C4A—C5A—C6A | 177.28 (17) | C9B—C10B—N1B—C3B | 1.54 (16) |
C4A—C5A—C6A—C7A | 0.5 (3) | O4B—C10B—N1B—C2B | −10.5 (2) |
C5A—C6A—C7A—C8A | 0.0 (3) | C9B—C10B—N1B—C2B | 169.65 (13) |
C6A—C7A—C8A—C9A | −0.3 (3) | O3B—C3B—N1B—C10B | 179.65 (14) |
C7A—C8A—C9A—C4A | 0.1 (3) | C4B—C3B—N1B—C10B | −0.99 (16) |
C7A—C8A—C9A—C10A | −178.19 (19) | O3B—C3B—N1B—C2B | 11.5 (2) |
C5A—C4A—C9A—C8A | 0.4 (3) | C4B—C3B—N1B—C2B | −169.17 (13) |
C3A—C4A—C9A—C8A | −178.01 (17) | C1B—C2B—N1B—C10B | −71.42 (18) |
C5A—C4A—C9A—C10A | 179.01 (15) | C1B—C2B—N1B—C3B | 95.41 (16) |
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H1OA···N1 | 1.00 (3) | 1.60 (3) | 2.5997 (19) | 177 (2) |
O2B—H1OB···O1 | 0.93 (2) | 1.75 (2) | 2.6736 (16) | 170 (2) |
N2—H1N2···O4Bi | 0.87 (2) | 2.22 (2) | 3.0549 (18) | 161 (2) |
C2A—H2A2···O3Bii | 0.97 | 2.57 | 3.477 (2) | 156 |
C5B—H5B···O1iii | 0.93 | 2.51 | 3.158 (2) | 126 |
C7B—H7B···O3Biv | 0.93 | 2.55 | 3.275 (2) | 135 |
C5—H5···O3Av | 0.93 | 2.48 | 3.341 (2) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y−1, z−1; (iii) −x+1, −y+3, −z+1; (iv) x+1, y, z; (v) −x−1, −y+1, −z. |
Experimental details
Crystal data | |
Chemical formula | 2C10H7NO4·C14H13N3O2 |
Mr | 665.61 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 8.1238 (4), 12.7963 (7), 15.9191 (11) |
α, β, γ (°) | 105.590 (5), 101.160 (5), 97.535 (4) |
V (Å3) | 1534.19 (17) |
Z | 2 |
Radiation type | Cu Kα |
µ (mm−1) | 0.91 |
Crystal size (mm) | 0.16 × 0.10 × 0.08 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur (Sapphire3, Gemini) |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009) |
Tmin, Tmax | 0.963, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 10334, 5912, 4836 |
Rint | 0.022 |
(sin θ/λ)max (Å−1) | 0.618 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.040, 0.116, 1.06 |
No. of reflections | 5912 |
No. of parameters | 456 |
H-atom treatment | H atoms treated by a mixture of independent and constrained refinement |
Δρmax, Δρmin (e Å−3) | 0.28, −0.21 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2009) and PARST (Nardelli, 1995).
D—H···A | D—H | H···A | D···A | D—H···A |
O2A—H1OA···N1 | 1.00 (3) | 1.60 (3) | 2.5997 (19) | 177 (2) |
O2B—H1OB···O1 | 0.93 (2) | 1.75 (2) | 2.6736 (16) | 170 (2) |
N2—H1N2···O4Bi | 0.87 (2) | 2.22 (2) | 3.0549 (18) | 161 (2) |
C2A—H2A2···O3Bii | 0.97 | 2.57 | 3.477 (2) | 156 |
C5B—H5B···O1iii | 0.93 | 2.51 | 3.158 (2) | 126 |
C7B—H7B···O3Biv | 0.93 | 2.55 | 3.275 (2) | 135 |
C5—H5···O3Av | 0.93 | 2.48 | 3.341 (2) | 154 |
Symmetry codes: (i) −x+1, −y+2, −z+1; (ii) x−1, y−1, z−1; (iii) −x+1, −y+3, −z+1; (iv) x+1, y, z; (v) −x−1, −y+1, −z. |
Acknowledgements
The authors are grateful to the Higher Education Authority of Iraq for sponsoring this project. Our gratitude is also extended to the Manchester Metropolitan University for facilitating and supporting this study. SBN and GAB thank the Ministry of Education, Science and Technological Development of the Republic of Serbia for the financial support (projects 172014 and 172035).
References
Barooah, N., Sarma, R. J., Batsanov, A. S. & Baruah, J. B. (2006). J. Mol. Struct. 791, 122–130. Web of Science CSD CrossRef CAS Google Scholar
Bijev, A. (2006). Lett. Drug. Des. Discov. 3, 506–512. Web of Science CrossRef CAS Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837–838. CrossRef CAS IUCr Journals Google Scholar
Feeder, N. & Jones, W. (1994). Acta Cryst. C50, 820–823. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Feeder, N. & Jones, W. (1996). Acta Cryst. C52, 913–919. CSD CrossRef CAS Web of Science IUCr Journals Google Scholar
Imramovský, A., Polanc, S., Vinšnová, J., Kočevar, M., Jampílek, J., Rečková, Z. & Kaustová, J. (2007). Bioorg. Med. Chem. 15, 2551–2559. Web of Science PubMed Google Scholar
Jing, Z.-L., Fan, Z., Yu, M., Chen, X. & Deng, Q.-L. (2005). Acta Cryst. E61, o3208–o3209. Web of Science CSD CrossRef IUCr Journals Google Scholar
Lin, M. & Liu, S.-X. (2007). Acta Cryst. E63, o3974. Web of Science CSD CrossRef IUCr Journals Google Scholar
Maccari, R., Ottana, R. & Vigorita, M. G. (2005). Bioorg. Med. Chem. Lett. 15, 2509–2513. Web of Science CrossRef PubMed CAS Google Scholar
Mohamed, S. K., Farrukh, M. A., Akkurt, M., Albayati, M. R. & Abdelhamid, A. A. (2012). Acta Cryst. E68, o2442. CSD CrossRef IUCr Journals Google Scholar
Nardelli, M. (1995). J. Appl. Cryst. 28, 659. CrossRef IUCr Journals Google Scholar
Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rajpurohit, S. & Sah, P. (2005). Asian J. Chem. 17, 949–954. CAS Google Scholar
Schultheiss, N. & Newman, A. (2009). Cryst. Growth Des. 9, 2950–2967. Web of Science CSD CrossRef PubMed CAS Google Scholar
Shanmuga Sundara Raj, S., Fun, H.-K., Lu, Z.-L., Xiao, W., Tong, Y.-X. & Kang, B.-S. (1999). Acta Cryst. C55, 942–944. CSD CrossRef IUCr Journals Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Shindikar, A. V. & Viswanathan, C. L. (2005). Bioorg. Med. Chem. Lett. 15, 1803–1806. Web of Science CrossRef PubMed CAS Google Scholar
Sinha, N., Jain, S., Tilekar, A., Upadhayaya, R. S., Kishore, N., Jana, G. H. & Arora, S. K. (2005). Bioorg. Med. Chem. Lett. 15, 1573–1576. Web of Science CrossRef PubMed CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wardell, S. M. S. V., de Souza, M. V. N., Wardell, J. L., Low, J. N. & Glidewell, C. (2007). Acta Cryst. B63, 879–895. Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Compounds incorporating the isoniazid (INH) core structure have shown high inhibitory activity in vitro (Bijev, 2006; Imramovský et al., 2007) and in mice towards M. tuberculosis H37Rv, ATCC 27294, M. tuberculosis clinical isolates and isoniazid-resistant M. tuberculosis (Maccari et al., 2005; Schultheiss & Newman 2009; Shindikar & Viswanathan, 2005; Sinha et al., 2005). In the present study we report the crystal structure of a novel, tricomponent cocrystal (I) containing the isoniazid-related hydrazone N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide and 2-(1,3-dioxoisoindolin-2-yl)acetic acid in a 1:2 molar ratio.
The asymmetric unit of (I) contains one hydrazone molecule and two crystallographically independent molecules of the acid denoted as A and B in Fig. 1. The A and B molecules tightly connect to the hydrazone via short and directional O2a—H1Oa···N1 and O2b— H1Ob···O1 hydrogen bond, respectively (Table 1). The interactions of A and B molecules significantly differ as their carboxyl acid groups, serving as proton donors, find different acceptors within the hydrazone molecule i.e. pyridinyl N1 and carboxyl O1 (Fig. 1). The interaction O2a—H1Oa···N1 which directly involves the acidic –COOH group and the most basic pyridinyl N1 atom causes the noticeable elongation of O2—H1Oa bond in molecule A (Table 1), yet no proton transfer occurs and all components remain neutral.
Besides the different engagement in the strongest interactions, the important difference between molecules A and B concerns their conformation. Thus the O1 carbonyl atom adopts trans and cis orientation relating to N1 atom in A and B. In addition, the O1—C1—C2—N1 torsion angle is 161.2 (2) and 1.4 (2)°, in molecules A and B respectively. It is worth mentioning that in a previously reported cocrystal (Mohamed et al., 2012) as well as in the crystal structures of 2-(1,3-dioxoisoindolin-2-yl)acetic acid containing one molecule in the asymmetric unit (Feeder & Jones, 1996), two independent molecules (Barooah et al., 2006) or the same molecule as monohydrate (Feeder & Jones, 1994), the value of the corresponding torsion angle O1—C1—C2—N1 is below 15.8° indicating the preferred conformation is similar to that of molecule B.
There are several crystal structures of hydrazone N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide describing this compound as monohydrate crystallizing in two forms, monoclinic (Jing et al., 2005; Shanmuga Sundara Raj et al., 1999; Wardell et al., 2007) and orthorhombic (Lin & Liu, 2007). The present form of the molecule shows no particular difference in bond lengths and angles in comparison to the previous ones.
The above described trimer with strongly intermolecular hydrogen-bonded components (Fig. 1), undergoes further arrangement via much weaker interamolecular interactions. Two such trimolecular units related by an inversion centre interact through a pair of N2—H1N2···O4b hydrogen bonds (Table 1) forming a 3 + 3 molecular aggregate.
Apart from this classical N—H···O hydrogen bond, the arrangement of the molecules in the cocrystal is further based on weak C— H···O (Table 1) and π–π interactions. Figure 2 displays the three-dimensional crystal packing as viewed down the a axis. The molecules of hydrazone are stacked in the ac plane with the perpendicular interplanar distances of 3.44 [for molecule at (-x, -y + 2, -z + 1)] and 3.46 Å [for molecule at (-x + 1, -y + 2, -z + 1)]. On the other hand, the acid molecules arrange along the c axis in an AABBAABB sequence, with the perpendicular distances between the rings ranging from 3.31 to 3.43 Å. Considering only the six membered aromatic rings one can observe only a modest overlap: Cg1···Cg2 (-x, -y + 2, -z + 1) = 3.8460 (10) Å, where Cg1 and Cg2 are the centroids of the N1—C5 and C8—C13 rings, respectively and Cg4···Cg4 (x + 1/2, -y + 1, -z) 3.8703 (13) Å where Cg4 is the centroid of the C4a—C9a ring.