(Z)-3-[2-(2,4-Di­nitro­phen­yl)hydrazin-1-yl­idene]isobenzo­furan-1(3H)-one di­chloro­methane hemisolvate

Agarwal, P.; Mishra, P.; Gupta, N.; Neelam; Sahoo, P.; Kumar, S.

doi:10.1107/S1600536814004929

organic compounds

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ISSN: 2056-9890

Volume 70| Part 4| April 2014| Page o418

doi:10.1107/S1600536814004929

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(Z)-3-[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]isobenzofuran-1(3H)-one dichloromethane hemisolvate

Palak Agarwal,^a Pragati Mishra,^a Nikita Gupta,^a Neelam,^a Priyaranjan Sahoo ^a and Satish Kumar ^a ^*

^aDepartment of Chemistry, St. Stephen's College, University Enclave, Delhi, 110007, India
^*Correspondence e-mail: satish@ststephens.edu

(Received 14 February 2014; accepted 3 March 2014; online 12 March 2014)

In the title compound, 2C₁₄H₈N₄O₆·CH₂Cl₂, the dichloromethane solvent molecule resides on a crystallographic twofold axis. The mean plane of the phthalisoimide ring is oriented at a dihedral angle of 32.93 (12)° with respect to the nitro-substituted benzene ring. An intramolecular N—H⋯O hydrogen bond occurs. The crystal packing features a short Cl⋯O halogen-bond interaction [3.093 (3) Å].

CCDC reference: 989735

Related literature

For a general background, see: Kaufmann (1927 ); Maekawa & Nanya (1959 ). For the preparation of hydrazone derivatives of phthalic anhydride, see: Chen et al. (1990 ). For halogen bond interactions, see: Gonnade et al. (2008 ); Metrangalo & Resnati (2007 ); Pedireddi et al. (1992 ). For a related structure, see: Guirado et al. (1997 ).

Experimental

Crystal data

2C₁₄H₈N₄O₆·CH₂Cl₂
M_r = 741.41
Monoclinic, C 2/c
a = 14.0834 (11) Å
b = 8.2605 (6) Å
c = 26.561 (2) Å
β = 93.816 (7)°
V = 3083.2 (3) Å³
Z = 4
Mo Kα radiation
μ = 0.29 mm⁻¹
T = 297 K
0.40 × 0.40 × 0.15 mm

Data collection

Agilent Xcalibur Sapphire3 diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011 ) T_min = 0.824, T_max = 1.000
20814 measured reflections
3832 independent reflections
2568 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.057
wR(F²) = 0.141
S = 1.03
3832 reflections
234 parameters
Only H-atom displacement parameters refined
Δρ_max = 0.44 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N6—H6⋯O3	0.81 (3)	1.99 (3)	2.613 (3)	134 (2)

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: 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: OLEX2 (Dolomanov et al., 2009 ) and Mercury (Macrae et al., 2008 ); software used to prepare material for publication: OLEX2 and publCIF (Westrip, 2010 ).

Supporting information

CCDC reference: 989735

Crystal structure: contains datablock I. DOI: 10.1107/S1600536814004929/fj2664sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536814004929/fj2664Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536814004929/fj2664Isup3.cdx

Supporting information file. DOI: 10.1107/S1600536814004929/fj2664Isup4.cml

checkCIF report

Comment top

Heterocyclic compounds are useful for their ion binding, medicinal and insecticidal properties. The title compound was synthesized as a side product in an effort directed towards development of colorimetric anion sensors and its crystal structure is reported here. The reaction involved treatment of 2,4-dinitrophenylhydrazine with phthaloyl chloride in presence of triethylamine as a base. There are only a few reports on the preparation of hydrazone derivatives of phthalic anhydride in the literature (Chen et al., 1990). The asymmetric unit (Fig. 1) consists of the title compound solvated with half a molecule of dichloromethane which lies on the crystallographic 2-fold axis. The phthalisoimides aromatic ring is nearly coplanar with nitroaromatic ring with a dihedral angle of 32.93 (C23—C11—C17—C10). A intramolecular hydrogen bond O3···H6 is also present in the title compound (Table 1). The crystal packing is stabilized by short Cl···.O halogen bond interaction (Fig 2) as reported in the literature (Gonnade et al., 2008), (Pedireddi et al., 1992), Metrangalo et al., 2007).

Related literature top

For a general background, see: Kaufmann (1927); Maekawa & Nanya (1959). For the preparation of hydrazone derivatives of phthalic anhydride, see: Chen et al. (1990). For halogen bond interactions, see: Gonnade et al. (2008); Metrangalo & Resnati (2007); Pedireddi et al. (1992). For [please specify], see: Guirado et al. (1997).

Experimental top

2,4-Dinitrophenylhydrazine (1.51 g, 7.65 mmol), dichloromethane (20 ml) and triethylamine (1 ml, 7.20 mmol) were taken in a 100 ml round bottom flask equipped with a magnetic stirrer bar. Phthalolyl chloride (0.5 ml, 2.46 mmol) was added to the stirred reaction mixture in a dropwise manner. The reaction mixture was stirred for 12 h and the precipitate obtained were filtered. The filtrate was added to 50 ml water. The organic layer was separated and washed thrice with 50 ml portion of 10% NaHCO₃ solution followed by water. Organic layer was dried over sodium sulfate and kept overnight to yield light yellowish red crystals of the title compound as the side product of the reaction. Melting point 94–95°C.

Computing details top

Data collection: CrysAlis PRO (Agilent, 2011); cell refinement: CrysAlis PRO (Agilent, 2011); data reduction: CrysAlis PRO (Agilent, 2011); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: OLEX2 (Dolomanov et al., 2009) and Mercury (Macrae et al., 2008); software used to prepare material for publication: OLEX2 (Dolomanov et al., 2009) and publCIF (Westrip, 2010).

Figures top

	Fig. 1. The molecular structure of the title compound, with atom labels and 50% probability displacement ellipsoids for non-H atoms.
	Fig. 2. The packing diagram of the title compound viewed viewed along b axis, showing short intermolecular O···Cl halogen bonds and intramolecular N—H···O hydrogen bonds.

(Z)-3-[2-(2,4-Dinitrophenyl)hydrazin-1-ylidene]isobenzofuran-1(3H)-one dichloromethane hemisolvate top

Crystal data top

2C₁₄H₈N₄O₆·CH₂Cl₂	F(000) = 1512
M_r = 741.41	D_x = 1.597 Mg m⁻³
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
a = 14.0834 (11) Å	Cell parameters from 3399 reflections
b = 8.2605 (6) Å	θ = 3.0–29.2°
c = 26.561 (2) Å	µ = 0.29 mm⁻¹
β = 93.816 (7)°	T = 297 K
V = 3083.2 (3) Å³	Rect. prism, clear yellow–red
Z = 4	0.4 × 0.4 × 0.15 mm

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	3832 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2568 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.039
Detector resolution: 15.9853 pixels mm^-1	θ_max = 29.3°, θ_min = 3.0°
ω scans	h = −19→19
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	k = −11→10
T_min = 0.824, T_max = 1.000	l = −35→36
20814 measured reflections

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Hydrogen site location: mixed
R[F² > 2σ(F²)] = 0.057	Only H-atom displacement parameters refined
wR(F²) = 0.141	w = 1/[σ²(F_o²) + (0.053P)² + 3.247P] where P = (F_o² + 2F_c²)/3
S = 1.03	(Δ/σ)_max < 0.001
3832 reflections	Δρ_max = 0.44 e Å⁻³
234 parameters	Δρ_min = −0.35 e Å⁻³
0 restraints

Crystal data top

2C₁₄H₈N₄O₆·CH₂Cl₂	V = 3083.2 (3) Å³
M_r = 741.41	Z = 4
Monoclinic, C2/c	Mo Kα radiation
a = 14.0834 (11) Å	µ = 0.29 mm⁻¹
b = 8.2605 (6) Å	T = 297 K
c = 26.561 (2) Å	0.4 × 0.4 × 0.15 mm
β = 93.816 (7)°

Data collection top

Agilent Xcalibur Sapphire3 diffractometer	3832 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Agilent, 2011)	2568 reflections with I > 2σ(I)
T_min = 0.824, T_max = 1.000	R_int = 0.039
20814 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.057	0 restraints
wR(F²) = 0.141	Only H-atom displacement parameters refined
S = 1.03	Δρ_max = 0.44 e Å⁻³
3832 reflections	Δρ_min = −0.35 e Å⁻³
234 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > σ(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ 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
Cl1	0.39898 (6)	0.54376 (10)	0.73756 (3)	0.0797 (3)
O2	0.41801 (11)	0.47047 (18)	0.54833 (5)	0.0411 (4)
O3	0.30079 (13)	0.1587 (2)	0.45274 (6)	0.0566 (5)
O4	0.48996 (13)	0.4056 (2)	0.62423 (6)	0.0562 (5)
O5	0.24791 (13)	0.0449 (2)	0.38349 (7)	0.0554 (5)
N6	0.33004 (14)	0.4709 (2)	0.45706 (7)	0.0407 (4)
H6	0.3319 (18)	0.386 (3)	0.4723 (9)	0.049*
N7	0.26939 (13)	0.1660 (2)	0.40803 (7)	0.0408 (4)
N8	0.16035 (16)	0.4760 (3)	0.26002 (7)	0.0529 (5)
N9	0.35397 (13)	0.6171 (2)	0.47867 (6)	0.0403 (4)
C10	0.21556 (15)	0.3263 (3)	0.33550 (8)	0.0381 (5)
H10	0.1961	0.2307	0.3195	0.046*
C11	0.42937 (14)	0.7496 (3)	0.55314 (8)	0.0357 (5)
C12	0.39564 (15)	0.6131 (3)	0.52246 (8)	0.0371 (5)
C13	0.47111 (15)	0.6872 (3)	0.59783 (8)	0.0377 (5)
C14	0.46430 (15)	0.5103 (3)	0.59583 (8)	0.0400 (5)
O15	0.1569 (2)	0.6044 (3)	0.23776 (8)	0.0904 (8)
O16	0.13589 (19)	0.3503 (3)	0.23967 (7)	0.0891 (8)
C17	0.28732 (14)	0.4683 (3)	0.40931 (7)	0.0355 (5)
C18	0.25776 (14)	0.3240 (3)	0.38441 (8)	0.0351 (5)
C19	0.20337 (15)	0.4720 (3)	0.31152 (8)	0.0396 (5)
C20	0.42629 (17)	0.9146 (3)	0.54405 (9)	0.0443 (5)
H20	0.3976	0.9565	0.5143	0.053*
C21	0.46757 (18)	1.0142 (3)	0.58095 (10)	0.0508 (6)
H21	0.4676	1.1255	0.5757	0.061*
C22	0.23198 (16)	0.6165 (3)	0.33451 (8)	0.0440 (5)
H22	0.2230	0.7141	0.3174	0.053*
C23	0.50939 (17)	0.9519 (3)	0.62607 (9)	0.0495 (6)
H23	0.5361	1.0227	0.6503	0.059*
C24	0.27340 (16)	0.6143 (3)	0.38250 (8)	0.0410 (5)
H24	0.2928	0.7112	0.3978	0.049*
C25	0.51179 (16)	0.7874 (3)	0.63543 (9)	0.0449 (6)
H25	0.5393	0.7456	0.6655	0.054*
C26	0.5000	0.4238 (5)	0.7500	0.0587 (10)
H26	0.4913	0.3631	0.7795	0.070*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0687 (5)	0.0757 (5)	0.0948 (6)	0.0155 (4)	0.0049 (4)	0.0027 (4)
O2	0.0502 (9)	0.0379 (8)	0.0340 (8)	0.0005 (7)	−0.0059 (7)	−0.0030 (7)
O3	0.0822 (13)	0.0478 (10)	0.0378 (9)	0.0001 (9)	−0.0120 (8)	0.0103 (8)
O4	0.0750 (12)	0.0465 (10)	0.0451 (10)	0.0060 (9)	−0.0122 (8)	0.0055 (8)
O5	0.0755 (12)	0.0371 (9)	0.0523 (10)	−0.0031 (8)	−0.0053 (9)	−0.0018 (8)
N6	0.0515 (11)	0.0388 (11)	0.0306 (10)	−0.0002 (9)	−0.0056 (8)	−0.0004 (8)
N7	0.0447 (10)	0.0401 (11)	0.0371 (10)	0.0008 (8)	−0.0003 (8)	0.0028 (8)
N8	0.0681 (14)	0.0512 (13)	0.0371 (11)	0.0025 (11)	−0.0126 (10)	0.0015 (10)
N9	0.0465 (10)	0.0418 (11)	0.0321 (9)	0.0003 (8)	−0.0013 (8)	−0.0045 (8)
C10	0.0406 (11)	0.0419 (12)	0.0311 (11)	0.0021 (10)	−0.0026 (9)	−0.0042 (9)
C11	0.0364 (10)	0.0406 (12)	0.0300 (10)	0.0003 (9)	0.0015 (8)	−0.0046 (9)
C12	0.0407 (11)	0.0391 (12)	0.0312 (11)	0.0045 (9)	−0.0001 (9)	−0.0010 (9)
C13	0.0372 (11)	0.0420 (12)	0.0339 (11)	0.0013 (9)	0.0011 (9)	−0.0034 (9)
C14	0.0418 (12)	0.0427 (13)	0.0348 (11)	0.0023 (10)	−0.0019 (9)	−0.0021 (10)
O15	0.151 (2)	0.0621 (13)	0.0527 (12)	0.0099 (14)	−0.0355 (13)	0.0106 (10)
O16	0.142 (2)	0.0669 (14)	0.0526 (12)	−0.0249 (14)	−0.0391 (13)	0.0023 (11)
C17	0.0340 (10)	0.0435 (12)	0.0287 (10)	0.0018 (9)	−0.0002 (8)	−0.0007 (9)
C18	0.0366 (10)	0.0362 (11)	0.0325 (11)	0.0033 (9)	0.0021 (8)	0.0006 (9)
C19	0.0421 (12)	0.0476 (13)	0.0282 (11)	0.0032 (10)	−0.0045 (9)	−0.0002 (10)
C20	0.0512 (13)	0.0395 (13)	0.0422 (12)	0.0028 (10)	0.0029 (10)	0.0016 (10)
C21	0.0580 (15)	0.0380 (13)	0.0570 (15)	−0.0044 (11)	0.0085 (12)	−0.0060 (11)
C22	0.0537 (14)	0.0413 (13)	0.0360 (12)	0.0056 (11)	−0.0032 (10)	0.0068 (10)
C23	0.0505 (14)	0.0505 (15)	0.0475 (14)	−0.0073 (11)	0.0028 (11)	−0.0169 (12)
C24	0.0489 (13)	0.0360 (12)	0.0374 (12)	0.0006 (10)	−0.0028 (10)	−0.0018 (9)
C25	0.0441 (12)	0.0541 (15)	0.0356 (12)	−0.0018 (11)	−0.0033 (9)	−0.0085 (10)
C26	0.070 (2)	0.052 (2)	0.053 (2)	0.000	−0.0091 (18)	0.000

Geometric parameters (Å, º) top

Cl1—C26	1.747 (2)	C11—C20	1.385 (3)
O2—C12	1.389 (3)	C13—C14	1.466 (3)
O2—C14	1.419 (3)	C13—C25	1.391 (3)
O3—N7	1.241 (2)	C17—C18	1.413 (3)
O4—C14	1.188 (3)	C17—C24	1.407 (3)
O5—N7	1.221 (2)	C19—C22	1.389 (3)
N6—H6	0.81 (3)	C20—H20	0.9300
N6—N9	1.370 (3)	C20—C21	1.378 (3)
N6—C17	1.367 (3)	C21—H21	0.9300
N7—C18	1.453 (3)	C21—C23	1.398 (4)
N8—O15	1.214 (3)	C22—H22	0.9300
N8—O16	1.210 (3)	C22—C24	1.366 (3)
N8—C19	1.459 (3)	C23—H23	0.9300
N9—C12	1.268 (3)	C23—C25	1.382 (3)
C10—H10	0.9300	C24—H24	0.9300
C10—C18	1.392 (3)	C25—H25	0.9300
C10—C19	1.367 (3)	C26—Cl1ⁱ	1.747 (2)
C11—C12	1.453 (3)	C26—H26	0.9440
C11—C13	1.388 (3)

C12—O2—C14	108.59 (16)	C24—C17—C18	117.35 (18)
N9—N6—H6	123.9 (18)	C10—C18—N7	116.37 (19)
C17—N6—H6	116.5 (18)	C10—C18—C17	121.29 (19)
C17—N6—N9	118.88 (18)	C17—C18—N7	122.34 (18)
O3—N7—C18	118.66 (18)	C10—C19—N8	119.2 (2)
O5—N7—O3	122.09 (19)	C10—C19—C22	121.89 (19)
O5—N7—C18	119.25 (17)	C22—C19—N8	118.9 (2)
O15—N8—C19	118.5 (2)	C11—C20—H20	121.4
O16—N8—O15	122.1 (2)	C21—C20—C11	117.2 (2)
O16—N8—C19	119.2 (2)	C21—C20—H20	121.4
C12—N9—N6	116.54 (18)	C20—C21—H21	119.2
C18—C10—H10	120.7	C20—C21—C23	121.6 (2)
C19—C10—H10	120.7	C23—C21—H21	119.2
C19—C10—C18	118.7 (2)	C19—C22—H22	120.3
C13—C11—C12	107.21 (19)	C24—C22—C19	119.5 (2)
C20—C11—C12	131.4 (2)	C24—C22—H22	120.3
C20—C11—C13	121.4 (2)	C21—C23—H23	119.3
O2—C12—C11	109.01 (17)	C25—C23—C21	121.4 (2)
N9—C12—O2	123.53 (19)	C25—C23—H23	119.3
N9—C12—C11	127.5 (2)	C17—C24—H24	119.3
C11—C13—C14	108.41 (19)	C22—C24—C17	121.3 (2)
C11—C13—C25	121.6 (2)	C22—C24—H24	119.3
C25—C13—C14	130.0 (2)	C13—C25—H25	121.6
O2—C14—C13	106.77 (18)	C23—C25—C13	116.9 (2)
O4—C14—O2	119.9 (2)	C23—C25—H25	121.6
O4—C14—C13	133.3 (2)	Cl1—C26—Cl1ⁱ	110.9 (2)
N6—C17—C18	123.03 (19)	Cl1—C26—H26	108.0
N6—C17—C24	119.6 (2)	Cl1ⁱ—C26—H26	107.0

O3—N7—C18—C10	−175.26 (19)	C14—O2—C12—N9	179.8 (2)
O3—N7—C18—C17	4.7 (3)	C14—O2—C12—C11	1.0 (2)
O5—N7—C18—C10	4.6 (3)	C14—C13—C25—C23	178.5 (2)
O5—N7—C18—C17	−175.45 (19)	O15—N8—C19—C10	−174.2 (2)
N6—N9—C12—O2	0.6 (3)	O15—N8—C19—C22	5.0 (4)
N6—N9—C12—C11	179.12 (19)	O16—N8—C19—C10	0.4 (4)
N6—C17—C18—N7	0.8 (3)	O16—N8—C19—C22	179.5 (2)
N6—C17—C18—C10	−179.2 (2)	C17—N6—N9—C12	−178.2 (2)
N6—C17—C24—C22	179.2 (2)	C18—C10—C19—N8	179.22 (19)
N8—C19—C22—C24	−179.2 (2)	C18—C10—C19—C22	0.1 (3)
N9—N6—C17—C18	−178.27 (18)	C18—C17—C24—C22	0.7 (3)
N9—N6—C17—C24	3.3 (3)	C19—C10—C18—N7	−179.73 (18)
C10—C19—C22—C24	−0.1 (3)	C19—C10—C18—C17	0.3 (3)
C11—C13—C14—O2	0.5 (2)	C19—C22—C24—C17	−0.3 (3)
C11—C13—C14—O4	179.2 (3)	C20—C11—C12—O2	178.5 (2)
C11—C13—C25—C23	−0.5 (3)	C20—C11—C12—N9	−0.1 (4)
C11—C20—C21—C23	−1.1 (3)	C20—C11—C13—C14	−179.2 (2)
C12—O2—C14—O4	−179.9 (2)	C20—C11—C13—C25	−0.1 (3)
C12—O2—C14—C13	−1.0 (2)	C20—C21—C23—C25	0.5 (4)
C12—C11—C13—C14	0.1 (2)	C21—C23—C25—C13	0.3 (3)
C12—C11—C13—C25	179.23 (19)	C24—C17—C18—N7	179.32 (19)
C12—C11—C20—C21	−178.3 (2)	C24—C17—C18—C10	−0.7 (3)
C13—C11—C12—O2	−0.7 (2)	C25—C13—C14—O2	−178.5 (2)
C13—C11—C12—N9	−179.4 (2)	C25—C13—C14—O4	0.2 (4)
C13—C11—C20—C21	0.9 (3)

Symmetry code: (i) −x+1, y, −z+3/2.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O3	0.81 (3)	1.99 (3)	2.613 (3)	134 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N6—H6···O3	0.81 (3)	1.99 (3)	2.613 (3)	134 (2)

Acknowledgements

The authors are thankful to the UGC (No. 41–235/2012) for providing a research grant. The authors are also thankful to the Principal of St Stephen's College and USIC (University of Delhi) for providing facilities.

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Volume 70| Part 4| April 2014| Page o418

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