2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-2-meth­oxy­benzyl­idene]pyridine-4-carbohydrazide (1/1)

Mohamed, S.K.; Farrukh, M.A.; Akkurt, M.; Albayati, M.R.; Abdelhamid, A.A.

doi:10.1107/S1600536812031388

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Page o2442

https://doi.org/10.1107/S1600536812031388

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2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-2-methoxybenzylidene]pyridine-4-carbohydrazide (1/1)

Shaaban K. Mohamed,^a Muhammad Akhyar Farrukh,^b Mehmet Akkurt,^c ^* Mustafa R. Albayati ^d and Antar A. Abdelhamid ^a

^aChemistry and Environmental Division, Manchester Metropolitan University, Manchester M1 5GD, England, ^bDepartment of Chemistry, Government College University, Lahore 54000, Pakistan, ^cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, and ^dChemistry Department, Tikrit University, Tikrit, Iraq
^*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 6 July 2012; accepted 10 July 2012; online 14 July 2012)

In the title 1:1 cocrystal, C₁₀H₇NO₄·C₁₄H₁₃N₃O₂, molecules are linked by intermolecular C—H⋯O, N—H⋯O and O—H⋯N hydrogen bonds, forming a three-dimensional network. In addition, π–π stacking interactions [with centroid–centroid distances of 3.5723 (19) and 3.6158 (18) Å] are observed.

Related literature

For the use of co-crystals in drug design and delivery, see: Vishweshwar et al. (2009 ); Peterson et al. (2006 ); McNamara et al. (2006 ). 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 ); Sriram et al. (2006 ).

Experimental

Crystal data

C₁₀H₇NO₄·C₁₄H₁₃N₃O₂
M_r = 460.44
Monoclinic, P 2₁ /n
a = 7.0747 (10) Å
b = 43.511 (6) Å
c = 7.5477 (9) Å
β = 110.015 (5)°
V = 2183.1 (5) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 296 K
0.30 × 0.20 × 0.20 mm

Data collection

Bruker Kappa APEXII CCD diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2005 ) T_min = 0.970, T_max = 0.980
19892 measured reflections
4304 independent reflections
2345 reflections with I > 2σ(I)
R_int = 0.061

Refinement

R[F² > 2σ(F²)] = 0.055
wR(F²) = 0.135
S = 1.02
4304 reflections
309 parameters
H-atom parameters constrained
Δρ_max = 0.14 e Å⁻³
Δρ_min = −0.18 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O3—H3A⋯N4ⁱ	0.82	1.86	2.681 (3)	177
N3—H3B⋯O6ⁱⁱ	0.86	2.12	2.958 (3)	164
C4—H4⋯O4ⁱⁱⁱ	0.93	2.44	3.190 (4)	138
C20—H20⋯O3ⁱⁱ	0.93	2.57	3.500 (4)	174
Symmetry codes: (i) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{3\over 2}}]$ ; (ii) $[x+{\script{1\over 2}}, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ ; (iii) -x+1, -y, -z.

Data collection: APEX2 (Bruker, 2009 ); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ); software used to prepare material for publication: WinGX (Farrugia, 1999 ) and PLATON (Spek, 2009 ).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536812031388/qm2075sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812031388/qm2075Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812031388/qm2075Isup3.cml

checkCIF report

Comment top

The use of co-crystals in drug design and delivery and as functional materials with potential applications as pharmaceuticals has recently attracted considerable interest (Vishweshwar et al., 2009; Peterson et al., 2006; McNamara et al., 2006). Moreover, co-crystallization in particular is a reliable method for the modification of drug physical and technical properties such as solubility, dissolution rate, stability, hygroscopisity and compressibility without alternating the pharmacological behaviour of their ingredients (Schultheiss & Newman, 2009). 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; Shindikar & Viswanathan, 2005; Sinha et al., 2005; Sriram et al., 2006). In this context and on continuation of our interest in the synthesis of potentially biologically active molecules based on the core structure of isoniazid we decided to investigate the reaction of isoniazid-related hydrazones with phthalimido-acetic acid. The reaction showed the unexpected co-crystallized product (I) with its ingridients in a 1:1 ratio. In this study we report a new co-crystallization method for the anti-tubercular drug N'-[(E)-(4-methoxyphenyl)methylidene]pyridine-4-carbohydrazide with (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid and the crystal structure of their cocrystal compound.

Fig. 1 shows the molecules of a 1:1 cocrystal of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid and N'-[(1E)-(2-methoxyphenyl)methylidene]pyridine-4-carbohydrazide. The bond lengths and bond angles are all within the expected ranges. In the molecule of (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid, the 2,3-dihydro-1H-isoindole ring (N1/C1–C8) is planar with a maimum deviation of 0.014 (3) Å for C2 atom. In the molecule of N'-[(1E)-(2-methoxyphenyl)methylidene]pyridine-4-carbohydrazide, the C11–C16 benzene and N4C19–C23 pyridine rings make a dihedral angle of 4.44 (15)° with each other.

The crystal structure is stabilized by intermolecular C—H···O, N—H···O and O—H···N hydrogen bonds, forming a three dimensional network (Table 1, Fig. 2). Furthermore, π-π stacking interactions [Cg3···Cg4(1 - x, -y, 1 - z) = 3.5723 (19) Å and Cg4···Cg4(1 - x, -y, -z) = 3.6158 (18) Å; where Cg3 and Cg4 are centroids of the N1/C1/C2/C7/C8 and C1–C6 rings, respectively] contribute to stabilize the crystal structure.

Related literature top

For the use of co-crystals in drug design and delivery, see: Vishweshwar et al. (2009); Peterson et al. (2006); McNamara et al. (2006). 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); Sriram et al. (2006).

Experimental top

A mixture of 255 mg (1 mmol) N'-[(E)-(2-methoxyphenyl)methylidene]pyridine-4-carbohydrazide and 205 mg (1 mmol) (1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)acetic acid in 50 ml e thanol was refluxed at 351 K for six hours. The reaction mixture was poured onto crushed ice to afford a solid product which was filtered off, washed with ethanol dried under vacuum and recrystallized from ethanol in good yield (78%). Crystals (m.p. 449 K) suitable for X-ray diffraction were grown by slow evaporation from an ethanol solution at room temperature over 24 h.

Structure description top

Computing details top

Data collection: APEX2 (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top

	Fig. 1. The molecular structure of (I) with the atom numbering scheme. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level.
	Fig. 2. The molecular packing and the hydrogen bonding viewed along the c axis. Hydrogen atoms not involved in hydrogen bonding have been omitted for clarity.

2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N'-[(E)-2-methoxybenzylidene]pyridine-4-carbohydrazide (1/1) top

Crystal data top

C₁₀H₇NO₄·C₁₄H₁₃N₃O₂	F(000) = 960
M_r = 460.44	D_x = 1.401 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 410 reflections
a = 7.0747 (10) Å	θ = 2.8–18.3°
b = 43.511 (6) Å	µ = 0.10 mm⁻¹
c = 7.5477 (9) Å	T = 296 K
β = 110.015 (5)°	Prism, white
V = 2183.1 (5) Å³	0.30 × 0.20 × 0.20 mm
Z = 4

Data collection top

Bruker Kappa APEXII CCD diffractometer	4304 independent reflections
Radiation source: fine-focus sealed tube	2345 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.061
ω scans	θ_max = 26.0°, θ_min = 1.9°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −8→8
T_min = 0.970, T_max = 0.980	k = −53→53
19892 measured reflections	l = −9→6

Refinement top

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)] = 0.055	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0485P)² + 0.2903P] where P = (F_o² + 2F_c²)/3
4304 reflections	(Δ/σ)_max < 0.001
309 parameters	Δρ_max = 0.14 e Å⁻³
0 restraints	Δρ_min = −0.18 e Å⁻³

Crystal data top

C₁₀H₇NO₄·C₁₄H₁₃N₃O₂	V = 2183.1 (5) Å³
M_r = 460.44	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 7.0747 (10) Å	µ = 0.10 mm⁻¹
b = 43.511 (6) Å	T = 296 K
c = 7.5477 (9) Å	0.30 × 0.20 × 0.20 mm
β = 110.015 (5)°

Data collection top

Bruker Kappa APEXII CCD diffractometer	4304 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2005)	2345 reflections with I > 2σ(I)
T_min = 0.970, T_max = 0.980	R_int = 0.061
19892 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.055	0 restraints
wR(F²) = 0.135	H-atom parameters constrained
S = 1.02	Δρ_max = 0.14 e Å⁻³
4304 reflections	Δρ_min = −0.18 e Å⁻³
309 parameters

Special details top

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F² for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The observed criterion of F² > σ(F²) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
O5	0.9659 (3)	0.13677 (4)	0.9365 (3)	0.0713 (9)
O6	0.7705 (3)	0.28342 (4)	0.8630 (2)	0.0491 (7)
N2	0.9227 (3)	0.22710 (5)	0.8728 (3)	0.0448 (8)
N3	0.9636 (3)	0.24511 (5)	1.0332 (3)	0.0431 (8)
N4	0.9687 (3)	0.32666 (5)	1.5100 (3)	0.0475 (9)
C11	0.9448 (4)	0.17874 (6)	0.7399 (4)	0.0426 (10)
C12	0.9519 (4)	0.14724 (6)	0.7626 (4)	0.0527 (11)
C13	0.9412 (5)	0.12788 (7)	0.6119 (5)	0.0733 (14)
C14	0.9201 (5)	0.14100 (10)	0.4399 (5)	0.0838 (16)
C15	0.9080 (5)	0.17224 (9)	0.4141 (5)	0.0780 (16)
C16	0.9193 (4)	0.19068 (7)	0.5638 (4)	0.0574 (11)
C17	0.9700 (4)	0.19899 (6)	0.9011 (4)	0.0425 (9)
C18	0.8817 (4)	0.27317 (6)	1.0142 (4)	0.0383 (9)
C19	0.9250 (3)	0.29134 (5)	1.1918 (3)	0.0345 (8)
C20	0.9321 (4)	0.32285 (6)	1.1838 (4)	0.0425 (9)
C21	0.9562 (4)	0.33942 (6)	1.3457 (4)	0.0478 (10)
C22	0.9617 (4)	0.29627 (6)	1.5154 (4)	0.0474 (10)
C23	0.9432 (4)	0.27773 (6)	1.3624 (3)	0.0432 (9)
C24	0.9578 (6)	0.10465 (7)	0.9630 (5)	0.0989 (18)
O1	0.1383 (4)	0.04421 (5)	0.1887 (3)	0.0801 (9)
O2	0.8106 (4)	0.05255 (5)	0.4959 (3)	0.0820 (9)
O3	0.4269 (3)	0.13691 (4)	0.2806 (3)	0.0563 (7)
O4	0.5019 (4)	0.09977 (4)	0.1147 (3)	0.0768 (9)
N1	0.4681 (4)	0.05545 (5)	0.3577 (3)	0.0530 (9)
C1	0.3116 (5)	0.03656 (7)	0.2495 (4)	0.0554 (11)
C2	0.4075 (5)	0.00722 (6)	0.2291 (4)	0.0524 (10)
C3	0.3233 (5)	−0.01899 (7)	0.1349 (4)	0.0665 (14)
C4	0.4514 (7)	−0.04291 (7)	0.1340 (4)	0.0748 (14)
C5	0.6539 (7)	−0.04044 (7)	0.2267 (5)	0.0771 (14)
C6	0.7384 (6)	−0.01406 (7)	0.3214 (4)	0.0711 (14)
C7	0.6119 (5)	0.00973 (6)	0.3213 (4)	0.0528 (10)
C8	0.6528 (5)	0.04091 (7)	0.4045 (4)	0.0562 (11)
C9	0.4417 (5)	0.08717 (6)	0.3977 (4)	0.0571 (10)
C10	0.4610 (4)	0.10833 (6)	0.2468 (4)	0.0495 (10)
H3B	1.03930	0.23840	1.14160	0.0520*
H13	0.94820	0.10670	0.62710	0.0880*
H14	0.91390	0.12830	0.33880	0.1000*
H15	0.89240	0.18070	0.29680	0.0940*
H16	0.90950	0.21190	0.54670	0.0690*
H17	1.02040	0.19130	1.02330	0.0510*
H20	0.92090	0.33280	1.07150	0.0510*
H21	0.96430	0.36070	1.34000	0.0570*
H22	0.96960	0.28690	1.62860	0.0570*
H23	0.94310	0.25640	1.37370	0.0520*
H24A	0.83290	0.09670	0.87840	0.1490*
H24B	0.96730	0.10060	1.09080	0.1490*
H24C	1.06770	0.09490	0.93790	0.1490*
H3	0.18520	−0.02070	0.07370	0.0800*
H3A	0.44340	0.14810	0.19960	0.0840*
H4	0.39910	−0.06090	0.06940	0.0900*
H5	0.73670	−0.05700	0.22570	0.0920*
H6	0.87640	−0.01250	0.38320	0.0850*
H9A	0.54170	0.09270	0.51780	0.0680*
H9B	0.30990	0.08980	0.40850	0.0680*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O5	0.0945 (17)	0.0458 (13)	0.0698 (15)	0.0059 (11)	0.0233 (12)	0.0036 (11)
O6	0.0610 (13)	0.0456 (11)	0.0326 (10)	0.0085 (9)	0.0054 (9)	0.0006 (8)
N2	0.0474 (14)	0.0426 (14)	0.0398 (13)	0.0021 (11)	0.0089 (10)	−0.0081 (10)
N3	0.0519 (14)	0.0403 (13)	0.0301 (12)	0.0075 (11)	0.0050 (10)	−0.0024 (10)
N4	0.0560 (16)	0.0456 (15)	0.0419 (14)	−0.0016 (11)	0.0179 (11)	−0.0047 (11)
C11	0.0352 (16)	0.0470 (17)	0.0452 (17)	−0.0030 (12)	0.0132 (12)	−0.0063 (13)
C12	0.0480 (19)	0.0502 (19)	0.0577 (19)	−0.0030 (14)	0.0154 (15)	−0.0086 (15)
C13	0.064 (2)	0.061 (2)	0.092 (3)	−0.0124 (17)	0.0228 (19)	−0.034 (2)
C14	0.079 (3)	0.108 (3)	0.068 (2)	−0.026 (2)	0.030 (2)	−0.044 (2)
C15	0.079 (3)	0.107 (3)	0.053 (2)	−0.030 (2)	0.0289 (18)	−0.019 (2)
C16	0.059 (2)	0.071 (2)	0.0436 (18)	−0.0141 (15)	0.0193 (15)	−0.0080 (15)
C17	0.0410 (16)	0.0442 (17)	0.0432 (15)	0.0010 (13)	0.0157 (12)	−0.0013 (13)
C18	0.0391 (16)	0.0390 (16)	0.0369 (15)	−0.0013 (12)	0.0131 (12)	0.0007 (12)
C19	0.0288 (14)	0.0390 (15)	0.0340 (14)	0.0002 (11)	0.0084 (11)	0.0010 (11)
C20	0.0460 (17)	0.0449 (17)	0.0360 (15)	−0.0030 (13)	0.0131 (12)	0.0019 (12)
C21	0.0545 (19)	0.0391 (16)	0.0489 (18)	−0.0064 (13)	0.0166 (14)	−0.0018 (14)
C22	0.0557 (19)	0.0493 (18)	0.0380 (15)	0.0031 (14)	0.0170 (13)	0.0041 (13)
C23	0.0527 (18)	0.0374 (15)	0.0407 (16)	0.0046 (13)	0.0177 (13)	0.0039 (12)
C24	0.125 (4)	0.047 (2)	0.114 (3)	0.001 (2)	0.027 (3)	0.014 (2)
O1	0.0718 (17)	0.0643 (15)	0.0895 (16)	0.0049 (13)	0.0088 (13)	0.0052 (12)
O2	0.0728 (17)	0.0660 (15)	0.0948 (17)	−0.0089 (13)	0.0128 (14)	−0.0199 (13)
O3	0.0881 (15)	0.0373 (11)	0.0495 (12)	0.0022 (10)	0.0312 (11)	0.0029 (9)
O4	0.136 (2)	0.0485 (13)	0.0652 (14)	0.0040 (12)	0.0592 (15)	−0.0054 (11)
N1	0.0680 (18)	0.0366 (13)	0.0507 (14)	−0.0013 (12)	0.0155 (13)	0.0014 (11)
C1	0.069 (2)	0.0473 (18)	0.0458 (17)	−0.0029 (17)	0.0143 (16)	0.0084 (14)
C2	0.080 (2)	0.0372 (17)	0.0402 (16)	−0.0030 (15)	0.0207 (16)	0.0047 (13)
C3	0.094 (3)	0.050 (2)	0.0545 (19)	−0.0154 (19)	0.0243 (18)	−0.0047 (15)
C4	0.127 (3)	0.043 (2)	0.062 (2)	−0.014 (2)	0.042 (2)	−0.0098 (16)
C5	0.119 (3)	0.048 (2)	0.075 (2)	0.013 (2)	0.047 (2)	0.0021 (18)
C6	0.087 (3)	0.055 (2)	0.071 (2)	0.0114 (19)	0.0266 (19)	−0.0008 (17)
C7	0.072 (2)	0.0431 (18)	0.0423 (16)	−0.0014 (15)	0.0181 (16)	0.0025 (13)
C8	0.071 (2)	0.0447 (18)	0.0505 (18)	−0.0034 (17)	0.0178 (17)	−0.0006 (14)
C9	0.083 (2)	0.0366 (16)	0.0546 (18)	−0.0009 (15)	0.0275 (16)	0.0006 (13)
C10	0.063 (2)	0.0380 (17)	0.0460 (17)	−0.0006 (13)	0.0168 (15)	−0.0031 (14)

Geometric parameters (Å, º) top

O5—C12	1.361 (4)	C22—C23	1.378 (4)
O5—C24	1.416 (4)	C13—H13	0.9300
O6—C18	1.227 (3)	C14—H14	0.9300
O1—C1	1.200 (5)	C15—H15	0.9300
O2—C8	1.205 (4)	C16—H16	0.9300
O3—C10	1.308 (3)	C17—H17	0.9300
O4—C10	1.189 (4)	C20—H20	0.9300
O3—H3A	0.8200	C21—H21	0.9300
N2—N3	1.387 (3)	C22—H22	0.9300
N2—C17	1.267 (3)	C23—H23	0.9300
N3—C18	1.338 (3)	C24—H24A	0.9600
N4—C21	1.334 (4)	C24—H24B	0.9600
N4—C22	1.324 (3)	C24—H24C	0.9600
N3—H3B	0.8600	C1—C2	1.478 (4)
N1—C9	1.439 (3)	C2—C3	1.368 (4)
N1—C8	1.384 (4)	C2—C7	1.378 (5)
N1—C1	1.396 (4)	C3—C4	1.382 (5)
C11—C17	1.463 (4)	C4—C5	1.367 (7)
C11—C12	1.380 (4)	C5—C6	1.376 (5)
C11—C16	1.380 (4)	C6—C7	1.368 (5)
C12—C13	1.397 (4)	C7—C8	1.481 (4)
C13—C14	1.379 (5)	C9—C10	1.507 (4)
C14—C15	1.372 (6)	C3—H3	0.9300
C15—C16	1.366 (5)	C4—H4	0.9300
C18—C19	1.495 (4)	C5—H5	0.9300
C19—C23	1.383 (3)	C6—H6	0.9300
C19—C20	1.374 (3)	C9—H9A	0.9700
C20—C21	1.378 (4)	C9—H9B	0.9700

C12—O5—C24	118.3 (2)	N4—C21—H21	118.00
C10—O3—H3A	110.00	N4—C22—H22	118.00
N3—N2—C17	115.7 (2)	C23—C22—H22	118.00
N2—N3—C18	118.0 (2)	C22—C23—H23	121.00
C21—N4—C22	116.9 (2)	C19—C23—H23	121.00
C18—N3—H3B	121.00	O5—C24—H24C	109.00
N2—N3—H3B	121.00	H24B—C24—H24C	110.00
C1—N1—C9	123.6 (3)	H24A—C24—H24B	110.00
C1—N1—C8	111.8 (2)	H24A—C24—H24C	109.00
C8—N1—C9	124.3 (3)	O5—C24—H24B	109.00
C12—C11—C16	118.7 (3)	O5—C24—H24A	110.00
C16—C11—C17	120.9 (2)	O1—C1—N1	124.2 (3)
C12—C11—C17	120.4 (3)	O1—C1—C2	130.2 (3)
C11—C12—C13	120.6 (3)	N1—C1—C2	105.6 (3)
O5—C12—C13	123.3 (2)	C1—C2—C3	129.8 (3)
O5—C12—C11	116.1 (2)	C1—C2—C7	108.6 (3)
C12—C13—C14	118.4 (3)	C3—C2—C7	121.6 (3)
C13—C14—C15	121.7 (3)	C2—C3—C4	117.5 (3)
C14—C15—C16	118.8 (3)	C3—C4—C5	120.9 (3)
C11—C16—C15	121.8 (3)	C4—C5—C6	121.6 (4)
N2—C17—C11	119.4 (3)	C5—C6—C7	117.6 (4)
N3—C18—C19	116.0 (2)	C2—C7—C8	107.8 (3)
O6—C18—C19	120.7 (2)	C6—C7—C8	131.3 (3)
O6—C18—N3	123.2 (2)	C2—C7—C6	120.9 (3)
C18—C19—C23	122.3 (2)	O2—C8—C7	129.5 (3)
C20—C19—C23	118.4 (2)	N1—C8—C7	106.3 (3)
C18—C19—C20	119.2 (2)	O2—C8—N1	124.2 (3)
C19—C20—C21	118.6 (2)	N1—C9—C10	112.1 (2)
N4—C21—C20	123.7 (2)	O3—C10—C9	111.3 (2)
N4—C22—C23	123.6 (3)	O4—C10—C9	123.6 (2)
C19—C23—C22	118.8 (2)	O3—C10—O4	125.1 (3)
C12—C13—H13	121.00	C2—C3—H3	121.00
C14—C13—H13	121.00	C4—C3—H3	121.00
C15—C14—H14	119.00	C3—C4—H4	120.00
C13—C14—H14	119.00	C5—C4—H4	120.00
C16—C15—H15	121.00	C4—C5—H5	119.00
C14—C15—H15	121.00	C6—C5—H5	119.00
C11—C16—H16	119.00	C5—C6—H6	121.00
C15—C16—H16	119.00	C7—C6—H6	121.00
N2—C17—H17	120.00	N1—C9—H9A	109.00
C11—C17—H17	120.00	N1—C9—H9B	109.00
C21—C20—H20	121.00	C10—C9—H9A	109.00
C19—C20—H20	121.00	C10—C9—H9B	109.00
C20—C21—H21	118.00	H9A—C9—H9B	108.00

C24—O5—C12—C11	175.1 (3)	O6—C18—C19—C23	142.3 (3)
C24—O5—C12—C13	−3.7 (5)	O6—C18—C19—C20	−32.7 (4)
C17—N2—N3—C18	−167.0 (3)	N3—C18—C19—C23	−34.9 (4)
N3—N2—C17—C11	−175.9 (2)	N3—C18—C19—C20	150.1 (3)
N2—N3—C18—O6	1.1 (4)	C18—C19—C23—C22	−173.1 (3)
N2—N3—C18—C19	178.2 (2)	C23—C19—C20—C21	−0.3 (4)
C22—N4—C21—C20	1.6 (4)	C18—C19—C20—C21	174.9 (3)
C21—N4—C22—C23	0.2 (4)	C20—C19—C23—C22	1.9 (4)
C1—N1—C9—C10	−87.7 (4)	C19—C20—C21—N4	−1.6 (5)
C8—N1—C9—C10	85.4 (3)	N4—C22—C23—C19	−1.9 (4)
C8—N1—C1—C2	0.9 (3)	O1—C1—C2—C3	0.1 (6)
C9—N1—C1—O1	−4.7 (5)	O1—C1—C2—C7	178.7 (3)
C9—N1—C1—C2	174.7 (3)	N1—C1—C2—C3	−179.2 (3)
C1—N1—C8—O2	179.4 (3)	N1—C1—C2—C7	−0.7 (3)
C1—N1—C8—C7	−0.8 (3)	C1—C2—C3—C4	177.8 (3)
C9—N1—C8—O2	5.7 (5)	C7—C2—C3—C4	−0.6 (5)
C8—N1—C1—O1	−178.5 (3)	C1—C2—C7—C6	−178.6 (3)
C9—N1—C8—C7	−174.5 (2)	C1—C2—C7—C8	0.2 (3)
C17—C11—C12—C13	−175.8 (3)	C3—C2—C7—C6	0.1 (5)
C12—C11—C16—C15	−2.3 (5)	C3—C2—C7—C8	178.9 (3)
C17—C11—C12—O5	5.4 (4)	C2—C3—C4—C5	1.1 (5)
C12—C11—C17—N2	−165.6 (3)	C3—C4—C5—C6	−1.1 (6)
C16—C11—C17—N2	16.3 (4)	C4—C5—C6—C7	0.6 (5)
C17—C11—C16—C15	175.9 (3)	C5—C6—C7—C2	−0.1 (5)
C16—C11—C12—O5	−176.4 (3)	C5—C6—C7—C8	−178.6 (3)
C16—C11—C12—C13	2.4 (5)	C2—C7—C8—O2	−179.9 (3)
C11—C12—C13—C14	−1.1 (5)	C2—C7—C8—N1	0.3 (3)
O5—C12—C13—C14	177.7 (3)	C6—C7—C8—O2	−1.3 (6)
C12—C13—C14—C15	−0.5 (6)	C6—C7—C8—N1	179.0 (3)
C13—C14—C15—C16	0.7 (6)	N1—C9—C10—O3	176.9 (3)
C14—C15—C16—C11	0.8 (5)	N1—C9—C10—O4	−3.0 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N4ⁱ	0.82	1.86	2.681 (3)	177
N3—H3B···O6ⁱⁱ	0.86	2.12	2.958 (3)	164
C4—H4···O4ⁱⁱⁱ	0.93	2.44	3.190 (4)	138
C20—H20···O3ⁱⁱ	0.93	2.57	3.500 (4)	174

Symmetry codes: (i) x−1/2, −y+1/2, z−3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z.

Experimental details

Crystal data
Chemical formula	C₁₀H₇NO₄·C₁₄H₁₃N₃O₂
M_r	460.44
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	296
a, b, c (Å)	7.0747 (10), 43.511 (6), 7.5477 (9)
β (°)	110.015 (5)
V (Å³)	2183.1 (5)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Bruker Kappa APEXII CCD
Absorption correction	Multi-scan (SADABS; Bruker, 2005)
T_min, T_max	0.970, 0.980
No. of measured, independent and observed [I > 2σ(I)] reflections	19892, 4304, 2345
R_int	0.061
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.055, 0.135, 1.02
No. of reflections	4304
No. of parameters	309
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.14, −0.18

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 1997), WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O3—H3A···N4ⁱ	0.82	1.86	2.681 (3)	177
N3—H3B···O6ⁱⁱ	0.86	2.12	2.958 (3)	164
C4—H4···O4ⁱⁱⁱ	0.93	2.44	3.190 (4)	138
C20—H20···O3ⁱⁱ	0.93	2.57	3.500 (4)	174

Symmetry codes: (i) x−1/2, −y+1/2, z−3/2; (ii) x+1/2, −y+1/2, z+1/2; (iii) −x+1, −y, −z.

Acknowledgements

The authors thank the Iraqi Higher Education Authority for their financial support. Manchester Metropolitan University is gratefully acknowledged for facilitating this study.

References

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

2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-2-meth­­oxy­benzyl­­idene]pyridine-4-carbohydrazide (1/1)

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

2-(1,3-Dioxoisoindolin-2-yl)acetic acid–N′-[(E)-2-methoxybenzylidene]pyridine-4-carbohydrazide (1/1)