4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)meth­yl]-N′-[(E)-4-nitro­benzyl­idene]benzene­sulfono­hydrazide dimethyl sulfoxide monosolvate

Bortoluzzi, A.J.; Policarpi, E.B.; Mora, C.; Oliveira, K.N.; Nunes, R.J.

doi:10.1107/S1600536811004697

organic compounds

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ISSN: 2056-9890

Volume 67| Part 3| March 2011| Pages o627-o628

doi:10.1107/S1600536811004697

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4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-N′-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide dimethyl sulfoxide monosolvate

Adailton J. Bortoluzzi,^a ^* Everton B. Policarpi,^a Cristiano Mora,^a Kely N. Oliveira ^a and Ricardo J. Nunes ^a

^aDepartamento de Química, Universidade Federal de Santa Catarina, 88040-900 Florianópolis, Brazil
^*Correspondence e-mail: adajb@qmc.ufsc.br

(Received 21 January 2011; accepted 7 February 2011; online 12 February 2011)

The molecular structure of the title compound, C₂₆H₁₈N₄O₆S·C₂H₆OS, shows an E conformation of the hydrazone double bond. The presence of a methylene group between the benzo[de]isoquinoline and benzenesulfonyl moieties allows the 4-nitrophenyl ring and the benzo[de]isoquinoline system to be parallel with respect to each other, so that the molecule adopts a U-shaped spatial conformation. The dihedral angle between mean planes of these aromatic groups is 4.4 (1)°. This special arrangement enables neighboring molecules to be intercalated, forming slipped π–π interactions [centroid–centroid distance = 3.535 (2) Å] between the 4-nitrophenyl and benzo[de]isoquinoline groups and point-to-face C—H⋯π interactions between the benzo[de]isoquinoline and benzenesulfonyl aromatic systems. In addition, the crystal packing also features an intermolecular N—H⋯O interaction involving the amine group and the dimethyl sulfoxide solvent molecule.

Related literature

For the therapeutic properties of sulfonylhydrazones, see: Rollas et al. (2002 ); Frlan et al. (2008 ); Lima et al. (1999 ); Sondhi et al. (2006 ) and for their biological activity, see: Kendall et al. (2007 ); Sadek et al. (2008 ). For the anticancer activity of naphthalimides, see: Braña & Ramos (2001 ); Braña et al. (2001 ); Suárez & Sánchez (1992 ); Ingrassia et al. (2009 ); Wu et al. (2009 ); Norton et al. (2008 ). For the therapeutic properties of cyclic imides, see: Cechinel Filho et al. (2003 ); Walter et al. (2002 ). For background to this study, see: Silva et al. (2006 ); Oliveira & Nunes (2006 ).

Experimental

Crystal data

C₂₆H₁₈N₄O₆S·C₂H₆OS
M_r = 592.63
Triclinic, $[P \overline 1]$
a = 9.152 (1) Å
b = 11.971 (1) Å
c = 13.910 (1) Å
α = 107.268 (7)°
β = 101.789 (7)°
γ = 96.319 (8)°
V = 1400.6 (2) Å³
Z = 2
Mo Kα radiation
μ = 0.24 mm⁻¹
T = 293 K
0.50 × 0.16 × 0.13 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
5055 measured reflections
4737 independent reflections
3075 reflections with I > 2σ(I)
R_int = 0.017
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.052
wR(F²) = 0.163
S = 1.04
4737 reflections
371 parameters
H-atom parameters constrained
Δρ_max = 0.73 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

Cg is the centroid of the p-nitrophenyl (C22–C27) ring.

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2N⋯O1S	0.80	1.99	2.764 (4)	163
C8—H8⋯Cgⁱ	0.93	2.90	3.799 (6)	162
Symmetry code: (i) -x+2, -y+2, -z+2.

Data collection: CAD-4 Software (Enraf–Nonius, 1989 ); cell refinement: CAD-4 Software; data reduction: HELENA (Spek, 1996 ); program(s) used to solve structure: SIR97 (Altomare et al., 1999 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ); molecular graphics: PLATON (Spek, 2009 ) and Mercury (Macrae et al., 2006 ); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811004697/ff2001sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811004697/ff2001Isup2.hkl

checkCIF report

Comment top

Sulfonyl-hydrazones are known for their therapeutic properties, such as, antimicrobial (Rollas et al. 2002, Frlan et al. 2008), analgesic (Lima et al. 1999, Sondhi et al. 2006), etc. Sulfonyl-hydrazones was selective inhibitor of p110α, a phosphoinositide-3-kinase that is over-expressed in 30% of tumors (Kendall et al. 2007). In innovative study, the sulfonyl-hydrazones were reported by enhance myocardial repair by stem cells by activating cardiac differentiation in human mobilized peripheral blood mononuclear cells (M-PBMCs) (Sadek et al. 2008).

Cyclic imides have also many therapeutic properties including antibacterial, antitumor, diuretic and antiviral (Cechinel Filho et al. 2003). In a previous publication, we reported the synthesis of imidobenzenesulfonyl compounds that showed promising analgesic profiles in the acetic acid- induced mice writhing test. The mechanism of action occurred possibly due to additional non-covalent interactions with the COX active site (Walter et al. 2002). The naphthalimides, in special, are known of their high DNA-binding ability and consequently many of them have anticancer property (Braña & Ramos, 2001); Braña et al. 2001). Mitonafide and Amonafide are classical examples of naphthalimides derivatives with antitumoral activity (Suárez et al. 1992). Recently, many similar compounds have been showed activity against different cancer cell lines (Ingrassia et al. 2009, Wu et al. 2009, Norton et al. 2008).

The title compound (I) (Scheme 1) was synthesized as a part of our work to investigate the antitumoral activity of the sulfonyl-hydrazones cyclic imides derivatives (Oliveira et al. 2006, Silva et al. 2006).

The molecular structure of the title compound (Fig. 1) shows E conformation on the hydrazone double bond, which is evidenced by the torsion angle S1–N2–N3–C21 of 165.8 (2)°. The presence of a methylene group among benzo[de]isoquinoline and benzenesulfonyl moieties allows p-nitrophenyl ring and benzo[de]isoquinoline system to be parallel with respect to each other, so that the molecule adopts an U-shaped spatial conformation. The dihedral angle between mean planes of these planar groups is 4.4 (1)°. This special arrangement enables the neighboring molecule be intercalated by a center of symmetry, forming pairs of molecules in a centrosymmetric structure (Fig. 2). Slipped π–π interaction between p-nitrophenyl and benzo[de]isoquinoline, with centroid–C12 distance of 3.589 Å, and point-to-face C–H···π interaction between benzenesulfonyl and benzo[de]isoquinoline aromatic systems, with centroid-H8 distance of 2.903 Å, are observed. In addition, crystal packing also shows an intermolecular N2–H···O1S interaction involving amine group and DMSO solvate.

Related literature top

For the therapeutic properties of sulfonylhydrazones, see: Rollas et al. (2002); Frlan et al. (2008); Lima et al. (1999); Sondhi et al. (2006) and for their biological activity, see: Kendall et al. (2007); Sadek et al. (2008). For the anticancer activity of naphthalimides, see: Braña & Ramos (2001); Braña et al. (2001); Suárez & Sánchez (1992); Ingrassia et al. (2009); Wu et al. (2009); Norton et al. (2008). For the therapeutic properties of cyclic imides, see: Cechinel Filho et al. (2003); Walter et al. (2002). For background to this study, see: Silva et al. (2006); Oliveira & Nunes (2006).

Experimental top

4-nitrobenzaldehyde (79 mg, 0.52 mmol) was added in a mixture of 4-[(1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl] benzenesulfonohydrazide (200 mg, 0.52 mmol) in ethanol (10 ml), with a drop of hydrochloric acid as catalyst, as described for similar compounds (Silva et al. 2006, Oliveira et al. 2006). The reaction was carried out by stirring at room temperature for one hour. The solid was filtered off with suction. The crystal used for data collection was obtained by dissolving 30 mg of (I) in 10 ml of dimethylsulfoxide and by slow evaporation of the solvent.

Computing details top

Data collection: CAD-4 Software (Enraf–Nonius, 1989); cell refinement: CAD-4 Software (Enraf–Nonius, 1989); data reduction: HELENA (Spek, 1996); program(s) used to solve structure: SIR97 (Altomare et al., 1999); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: PLATON (Spek, 2009) and Mercury (Macrae et al., 2006); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title compound with the labelling scheme. Displacement ellipsoids are shown at the 40% probability level.
	Fig. 2. Intermolecular interactions observed in (I).

4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]- N'-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide dimethyl sulfoxide monosolvate top

Crystal data top

C₂₆H₁₈N₄O₆S·C₂H₆OS	Z = 2
M_r = 592.63	F(000) = 616
Triclinic, P1	D_x = 1.405 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.152 (1) Å	Cell parameters from 25 reflections
b = 11.971 (1) Å	θ = 8.5–13.4°
c = 13.910 (1) Å	µ = 0.24 mm⁻¹
α = 107.268 (7)°	T = 293 K
β = 101.789 (7)°	Prismatic, colourless
γ = 96.319 (8)°	0.50 × 0.16 × 0.13 mm
V = 1400.6 (2) Å³

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.017
Radiation source: fine-focus sealed tube	θ_max = 25.1°, θ_min = 2.3°
Graphite monochromator	h = 0→10
ω–2θ scans	k = −14→14
5055 measured reflections	l = −16→16
4737 independent reflections	3 standard reflections every 200 reflections
3075 reflections with I > 2σ(I)	intensity decay: 1%

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)] = 0.052	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	w = 1/[σ²(F_o²) + (0.0792P)² + 0.613P] where P = (F_o² + 2F_c²)/3
4737 reflections	(Δ/σ)_max < 0.001
371 parameters	Δρ_max = 0.73 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₆H₁₈N₄O₆S·C₂H₆OS	γ = 96.319 (8)°
M_r = 592.63	V = 1400.6 (2) Å³
Triclinic, P1	Z = 2
a = 9.152 (1) Å	Mo Kα radiation
b = 11.971 (1) Å	µ = 0.24 mm⁻¹
c = 13.910 (1) Å	T = 293 K
α = 107.268 (7)°	0.50 × 0.16 × 0.13 mm
β = 101.789 (7)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	R_int = 0.017
5055 measured reflections	3 standard reflections every 200 reflections
4737 independent reflections	intensity decay: 1%
3075 reflections with I > 2σ(I)

Refinement top

R[F² > 2σ(F²)] = 0.052	0 restraints
wR(F²) = 0.163	H-atom parameters constrained
S = 1.04	Δρ_max = 0.73 e Å⁻³
4737 reflections	Δρ_min = −0.43 e Å⁻³
371 parameters

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

	x	y	z	U_iso*/U_eq
S1	0.34031 (11)	0.73620 (8)	0.53120 (6)	0.0597 (3)
N1	0.8354 (3)	1.1992 (2)	0.8805 (2)	0.0571 (7)
N2	0.4477 (3)	0.6426 (2)	0.55446 (19)	0.0540 (7)
H2N	0.5170	0.6398	0.5273	0.058 (12)*
N3	0.4776 (3)	0.6399 (2)	0.65605 (19)	0.0501 (6)
O1	0.6771 (4)	1.2526 (3)	0.9840 (2)	0.1026 (11)
O2	0.9903 (3)	1.1379 (3)	0.7756 (2)	0.0987 (10)
O3	0.3260 (3)	0.7192 (2)	0.42331 (18)	0.0797 (8)
O4	0.2088 (3)	0.7188 (2)	0.5685 (2)	0.0766 (8)
C2	0.7994 (4)	1.2237 (3)	0.9760 (3)	0.0626 (9)
C3	0.9105 (4)	1.2127 (3)	1.0630 (2)	0.0547 (8)
C4	0.8859 (5)	1.2441 (4)	1.1612 (3)	0.0767 (11)
H4	0.7994	1.2747	1.1724	0.092*
C5	0.9881 (6)	1.2309 (4)	1.2432 (3)	0.0864 (13)
H5	0.9706	1.2547	1.3092	0.104*
C6	1.1117 (6)	1.1846 (4)	1.2296 (3)	0.0803 (13)
H6	1.1779	1.1753	1.2858	0.096*
C7	1.1429 (4)	1.1495 (3)	1.1304 (3)	0.0645 (10)
C8	1.2697 (5)	1.1010 (4)	1.1103 (5)	0.0918 (15)
H8	1.3383	1.0895	1.1643	0.110*
C9	1.2953 (5)	1.0705 (4)	1.0149 (6)	0.1053 (19)
H9	1.3799	1.0370	1.0038	0.126*
C10	1.1970 (5)	1.0884 (4)	0.9325 (4)	0.0845 (13)
H10	1.2170	1.0683	0.8672	0.101*
C11	1.0701 (4)	1.1359 (3)	0.9479 (3)	0.0547 (8)
C12	1.0410 (4)	1.1663 (3)	1.0464 (3)	0.0492 (8)
C13	0.9662 (4)	1.1572 (3)	0.8612 (3)	0.0636 (10)
C14	0.7269 (5)	1.2149 (3)	0.7930 (3)	0.0737 (11)
H14A	0.7827	1.2462	0.7515	0.088*
H14B	0.6660	1.2723	0.8202	0.088*
C15	0.6233 (4)	1.0984 (3)	0.7248 (3)	0.0602 (9)
C16	0.6623 (5)	1.0275 (3)	0.6388 (3)	0.0680 (10)
H16	0.7496	1.0539	0.6214	0.082*
C17	0.5738 (4)	0.9184 (3)	0.5784 (3)	0.0636 (9)
H17	0.6009	0.8715	0.5208	0.076*
C18	0.4443 (4)	0.8797 (3)	0.6049 (2)	0.0535 (8)
C19	0.4011 (4)	0.9501 (4)	0.6880 (3)	0.0714 (10)
H19	0.3127	0.9246	0.7045	0.086*
C20	0.4909 (5)	1.0596 (4)	0.7469 (3)	0.0765 (11)
H20	0.4611	1.1079	0.8027	0.092*
C21	0.5844 (4)	0.5873 (3)	0.6806 (2)	0.0500 (8)
H21	0.6372	0.5541	0.6320	0.060*
C22	0.6255 (4)	0.5781 (3)	0.7849 (2)	0.0475 (7)
C23	0.7517 (4)	0.5304 (3)	0.8140 (3)	0.0580 (9)
H23	0.8057	0.4994	0.7655	0.070*
C24	0.7984 (4)	0.5285 (3)	0.9143 (3)	0.0613 (9)
H24	0.8839	0.4973	0.9341	0.074*
C25	0.7162 (4)	0.5734 (3)	0.9838 (2)	0.0550 (8)
C26	0.5894 (4)	0.6196 (3)	0.9578 (3)	0.0638 (9)
H26	0.5356	0.6495	1.0067	0.077*
C27	0.5431 (4)	0.6209 (3)	0.8576 (3)	0.0615 (9)
H27	0.4561	0.6507	0.8382	0.074*
N4	0.7691 (4)	0.5767 (3)	1.0923 (3)	0.0733 (9)
O5	0.6974 (4)	0.6209 (4)	1.1535 (2)	0.1111 (12)
O6	0.8819 (4)	0.5387 (4)	1.1166 (2)	0.1188 (13)
S2	0.74498 (12)	0.64956 (10)	0.39415 (8)	0.0747 (3)
O1S	0.7208 (3)	0.6673 (3)	0.5003 (2)	0.0830 (8)
C1S	0.8748 (5)	0.5522 (4)	0.3777 (3)	0.0833 (12)
H1S1	0.8257	0.4734	0.3689	0.125*
H1S2	0.9591	0.5784	0.4379	0.125*
H1S3	0.9105	0.5515	0.3173	0.125*
C2S	0.8693 (6)	0.7814 (4)	0.4070 (4)	0.1081 (17)
H2S1	0.8157	0.8468	0.4170	0.162*
H2S2	0.9049	0.7705	0.3451	0.162*
H2S3	0.9542	0.7979	0.4657	0.162*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S1	0.0667 (6)	0.0595 (5)	0.0449 (5)	−0.0013 (4)	−0.0036 (4)	0.0219 (4)
N1	0.0665 (19)	0.0523 (16)	0.0478 (16)	0.0087 (14)	0.0064 (14)	0.0155 (13)
N2	0.0696 (19)	0.0552 (16)	0.0371 (14)	0.0016 (14)	0.0122 (14)	0.0193 (12)
N3	0.0566 (16)	0.0536 (15)	0.0412 (14)	0.0033 (13)	0.0094 (12)	0.0217 (12)
O1	0.084 (2)	0.137 (3)	0.079 (2)	0.060 (2)	0.0151 (16)	0.0140 (19)
O2	0.103 (2)	0.127 (3)	0.0623 (18)	−0.0099 (19)	0.0389 (17)	0.0240 (17)
O3	0.113 (2)	0.0723 (17)	0.0391 (13)	−0.0025 (15)	−0.0086 (13)	0.0230 (12)
O4	0.0539 (15)	0.0878 (19)	0.0830 (19)	0.0021 (13)	0.0062 (13)	0.0319 (15)
C2	0.064 (2)	0.062 (2)	0.055 (2)	0.0181 (18)	0.0125 (18)	0.0088 (17)
C3	0.059 (2)	0.055 (2)	0.0449 (19)	0.0089 (16)	0.0094 (16)	0.0111 (15)
C4	0.077 (3)	0.085 (3)	0.059 (2)	0.014 (2)	0.019 (2)	0.010 (2)
C5	0.103 (4)	0.097 (3)	0.046 (2)	−0.003 (3)	0.011 (2)	0.019 (2)
C6	0.094 (3)	0.068 (3)	0.062 (3)	−0.011 (2)	−0.012 (2)	0.028 (2)
C7	0.058 (2)	0.0424 (18)	0.079 (3)	−0.0036 (16)	−0.0068 (19)	0.0200 (17)
C8	0.062 (3)	0.057 (2)	0.136 (5)	0.007 (2)	−0.012 (3)	0.028 (3)
C9	0.053 (3)	0.075 (3)	0.170 (6)	0.020 (2)	0.022 (3)	0.015 (3)
C10	0.062 (3)	0.068 (3)	0.111 (4)	0.003 (2)	0.038 (3)	0.004 (2)
C11	0.0454 (19)	0.0446 (17)	0.066 (2)	−0.0026 (15)	0.0159 (17)	0.0083 (16)
C12	0.0477 (19)	0.0370 (16)	0.057 (2)	−0.0010 (14)	0.0091 (15)	0.0119 (14)
C13	0.073 (3)	0.054 (2)	0.058 (2)	−0.0128 (18)	0.0226 (19)	0.0129 (17)
C14	0.099 (3)	0.054 (2)	0.058 (2)	0.008 (2)	−0.003 (2)	0.0214 (17)
C15	0.083 (3)	0.0477 (19)	0.0437 (19)	0.0127 (18)	−0.0020 (18)	0.0186 (15)
C16	0.082 (3)	0.060 (2)	0.059 (2)	−0.0055 (19)	0.014 (2)	0.0247 (18)
C17	0.080 (3)	0.056 (2)	0.051 (2)	0.0032 (19)	0.0152 (19)	0.0167 (16)
C18	0.062 (2)	0.0540 (19)	0.0415 (18)	0.0084 (16)	0.0002 (15)	0.0211 (15)
C19	0.067 (2)	0.080 (3)	0.061 (2)	0.007 (2)	0.0146 (19)	0.017 (2)
C20	0.080 (3)	0.072 (3)	0.060 (2)	0.009 (2)	0.012 (2)	0.004 (2)
C21	0.061 (2)	0.0471 (17)	0.0396 (17)	0.0028 (16)	0.0122 (15)	0.0141 (14)
C22	0.0561 (19)	0.0409 (16)	0.0446 (17)	0.0047 (14)	0.0108 (15)	0.0152 (13)
C23	0.073 (2)	0.053 (2)	0.051 (2)	0.0212 (17)	0.0210 (17)	0.0152 (16)
C24	0.069 (2)	0.062 (2)	0.055 (2)	0.0231 (18)	0.0075 (18)	0.0227 (17)
C25	0.064 (2)	0.055 (2)	0.0431 (18)	0.0007 (17)	0.0074 (16)	0.0192 (15)
C26	0.068 (2)	0.081 (3)	0.053 (2)	0.017 (2)	0.0235 (18)	0.0292 (19)
C27	0.057 (2)	0.083 (3)	0.057 (2)	0.0212 (19)	0.0184 (17)	0.0352 (19)
N4	0.080 (2)	0.087 (2)	0.052 (2)	0.0088 (19)	0.0094 (18)	0.0279 (17)
O5	0.115 (3)	0.171 (3)	0.0557 (18)	0.032 (2)	0.0289 (19)	0.043 (2)
O6	0.121 (3)	0.182 (4)	0.072 (2)	0.070 (3)	0.0121 (19)	0.062 (2)
S2	0.0732 (7)	0.1007 (8)	0.0565 (6)	0.0068 (6)	0.0234 (5)	0.0332 (5)
O1S	0.103 (2)	0.095 (2)	0.0608 (16)	0.0099 (16)	0.0414 (15)	0.0291 (14)
C1S	0.080 (3)	0.094 (3)	0.077 (3)	0.010 (2)	0.028 (2)	0.025 (2)
C2S	0.130 (4)	0.101 (4)	0.115 (4)	0.005 (3)	0.060 (3)	0.053 (3)

Geometric parameters (Å, º) top

S1—O4	1.423 (3)	C15—C20	1.375 (5)
S1—O3	1.429 (2)	C15—C16	1.384 (5)
S1—N2	1.630 (3)	C16—C17	1.381 (5)
S1—C18	1.762 (3)	C16—H16	0.9300
N1—C2	1.388 (4)	C17—C18	1.383 (5)
N1—C13	1.394 (5)	C17—H17	0.9300
N1—C14	1.478 (4)	C18—C19	1.373 (5)
N2—N3	1.394 (3)	C19—C20	1.383 (5)
N2—H2N	0.8006	C19—H19	0.9300
N3—C21	1.263 (4)	C20—H20	0.9300
O1—C2	1.224 (4)	C21—C22	1.462 (4)
O2—C13	1.214 (4)	C21—H21	0.9300
C2—C3	1.461 (5)	C22—C23	1.383 (4)
C3—C4	1.377 (5)	C22—C27	1.394 (4)
C3—C12	1.404 (5)	C23—C24	1.381 (5)
C4—C5	1.380 (6)	C23—H23	0.9300
C4—H4	0.9300	C24—C25	1.367 (5)
C5—C6	1.336 (6)	C24—H24	0.9300
C5—H5	0.9300	C25—C26	1.369 (5)
C6—C7	1.415 (6)	C25—N4	1.474 (4)
C6—H6	0.9300	C26—C27	1.377 (5)
C7—C8	1.395 (6)	C26—H26	0.9300
C7—C12	1.418 (5)	C27—H27	0.9300
C8—C9	1.344 (7)	N4—O6	1.200 (4)
C8—H8	0.9300	N4—O5	1.213 (4)
C9—C10	1.391 (7)	S2—O1S	1.494 (3)
C9—H9	0.9300	S2—C1S	1.755 (4)
C10—C11	1.375 (5)	S2—C2S	1.781 (5)
C10—H10	0.9300	C1S—H1S1	0.9600
C11—C12	1.399 (5)	C1S—H1S2	0.9600
C11—C13	1.481 (5)	C1S—H1S3	0.9600
C14—C15	1.517 (5)	C2S—H2S1	0.9600
C14—H14A	0.9700	C2S—H2S2	0.9600
C14—H14B	0.9700	C2S—H2S3	0.9600

O4—S1—O3	120.25 (16)	C20—C15—C14	121.5 (4)
O4—S1—N2	108.61 (16)	C16—C15—C14	120.0 (4)
O3—S1—N2	103.64 (16)	C17—C16—C15	121.1 (4)
O4—S1—C18	107.94 (17)	C17—C16—H16	119.5
O3—S1—C18	109.03 (15)	C15—C16—H16	119.5
N2—S1—C18	106.58 (15)	C16—C17—C18	119.1 (4)
C2—N1—C13	123.8 (3)	C16—C17—H17	120.4
C2—N1—C14	118.4 (3)	C18—C17—H17	120.4
C13—N1—C14	117.7 (3)	C19—C18—C17	120.7 (3)
N3—N2—S1	115.3 (2)	C19—C18—S1	121.3 (3)
N3—N2—H2N	117.1	C17—C18—S1	118.0 (3)
S1—N2—H2N	114.1	C18—C19—C20	119.2 (4)
C21—N3—N2	115.5 (3)	C18—C19—H19	120.4
O1—C2—N1	119.3 (3)	C20—C19—H19	120.4
O1—C2—C3	122.8 (3)	C15—C20—C19	121.4 (4)
N1—C2—C3	117.9 (3)	C15—C20—H20	119.3
C4—C3—C12	119.4 (3)	C19—C20—H20	119.3
C4—C3—C2	120.4 (3)	N3—C21—C22	120.5 (3)
C12—C3—C2	120.1 (3)	N3—C21—H21	119.7
C3—C4—C5	120.8 (4)	C22—C21—H21	119.7
C3—C4—H4	119.6	C23—C22—C27	118.9 (3)
C5—C4—H4	119.6	C23—C22—C21	119.9 (3)
C6—C5—C4	121.3 (4)	C27—C22—C21	121.1 (3)
C6—C5—H5	119.4	C24—C23—C22	120.7 (3)
C4—C5—H5	119.4	C24—C23—H23	119.6
C5—C6—C7	120.7 (4)	C22—C23—H23	119.6
C5—C6—H6	119.6	C25—C24—C23	118.5 (3)
C7—C6—H6	119.6	C25—C24—H24	120.7
C8—C7—C6	124.0 (4)	C23—C24—H24	120.7
C8—C7—C12	117.6 (4)	C24—C25—C26	122.6 (3)
C6—C7—C12	118.3 (4)	C24—C25—N4	118.9 (3)
C9—C8—C7	121.7 (5)	C26—C25—N4	118.5 (3)
C9—C8—H8	119.1	C25—C26—C27	118.6 (3)
C7—C8—H8	119.1	C25—C26—H26	120.7
C8—C9—C10	120.9 (4)	C27—C26—H26	120.7
C8—C9—H9	119.6	C26—C27—C22	120.6 (3)
C10—C9—H9	119.6	C26—C27—H27	119.7
C11—C10—C9	119.9 (5)	C22—C27—H27	119.7
C11—C10—H10	120.1	O6—N4—O5	123.1 (4)
C9—C10—H10	120.1	O6—N4—C25	119.1 (4)
C10—C11—C12	119.8 (4)	O5—N4—C25	117.7 (4)
C10—C11—C13	120.2 (4)	O1S—S2—C1S	106.61 (19)
C12—C11—C13	119.9 (3)	O1S—S2—C2S	104.8 (2)
C11—C12—C3	120.5 (3)	C1S—S2—C2S	97.5 (2)
C11—C12—C7	120.1 (3)	S2—C1S—H1S1	109.5
C3—C12—C7	119.4 (3)	S2—C1S—H1S2	109.5
O2—C13—N1	120.1 (4)	H1S1—C1S—H1S2	109.5
O2—C13—C11	122.6 (4)	S2—C1S—H1S3	109.5
N1—C13—C11	117.3 (3)	H1S1—C1S—H1S3	109.5
N1—C14—C15	111.5 (3)	H1S2—C1S—H1S3	109.5
N1—C14—H14A	109.3	S2—C2S—H2S1	109.5
C15—C14—H14A	109.3	S2—C2S—H2S2	109.5
N1—C14—H14B	109.3	H2S1—C2S—H2S2	109.5
C15—C14—H14B	109.3	S2—C2S—H2S3	109.5
H14A—C14—H14B	108.0	H2S1—C2S—H2S3	109.5
C20—C15—C16	118.5 (3)	H2S2—C2S—H2S3	109.5

O4—S1—N2—N3	−49.9 (3)	C12—C11—C13—O2	176.2 (3)
O3—S1—N2—N3	−178.9 (2)	C10—C11—C13—N1	176.5 (3)
C18—S1—N2—N3	66.1 (3)	C12—C11—C13—N1	−4.8 (4)
S1—N2—N3—C21	−165.8 (2)	C2—N1—C14—C15	−96.1 (4)
C13—N1—C2—O1	−175.1 (3)	C13—N1—C14—C15	82.0 (4)
C14—N1—C2—O1	2.9 (5)	N1—C14—C15—C20	86.5 (5)
C13—N1—C2—C3	4.6 (5)	N1—C14—C15—C16	−92.5 (4)
C14—N1—C2—C3	−177.4 (3)	C20—C15—C16—C17	−2.3 (5)
O1—C2—C3—C4	−5.1 (6)	C14—C15—C16—C17	176.8 (3)
N1—C2—C3—C4	175.2 (3)	C15—C16—C17—C18	−0.1 (5)
O1—C2—C3—C12	172.8 (4)	C16—C17—C18—C19	2.1 (5)
N1—C2—C3—C12	−6.8 (5)	C16—C17—C18—S1	−176.1 (3)
C12—C3—C4—C5	0.2 (6)	O4—S1—C18—C19	5.1 (3)
C2—C3—C4—C5	178.1 (4)	O3—S1—C18—C19	137.3 (3)
C3—C4—C5—C6	−1.7 (7)	N2—S1—C18—C19	−111.5 (3)
C4—C5—C6—C7	1.1 (7)	O4—S1—C18—C17	−176.8 (3)
C5—C6—C7—C8	179.7 (4)	O3—S1—C18—C17	−44.6 (3)
C5—C6—C7—C12	0.8 (5)	N2—S1—C18—C17	66.7 (3)
C6—C7—C8—C9	−179.1 (4)	C17—C18—C19—C20	−1.6 (5)
C12—C7—C8—C9	−0.2 (6)	S1—C18—C19—C20	176.6 (3)
C7—C8—C9—C10	1.2 (7)	C16—C15—C20—C19	2.8 (6)
C8—C9—C10—C11	−1.2 (7)	C14—C15—C20—C19	−176.2 (3)
C9—C10—C11—C12	0.2 (5)	C18—C19—C20—C15	−0.9 (6)
C9—C10—C11—C13	179.0 (4)	N2—N3—C21—C22	−179.6 (2)
C10—C11—C12—C3	−178.8 (3)	N3—C21—C22—C23	−173.8 (3)
C13—C11—C12—C3	2.5 (4)	N3—C21—C22—C27	3.6 (5)
C10—C11—C12—C7	0.7 (5)	C27—C22—C23—C24	−2.0 (5)
C13—C11—C12—C7	−178.0 (3)	C21—C22—C23—C24	175.5 (3)
C4—C3—C12—C11	−178.7 (3)	C22—C23—C24—C25	0.7 (5)
C2—C3—C12—C11	3.3 (5)	C23—C24—C25—C26	0.3 (5)
C4—C3—C12—C7	1.8 (5)	C23—C24—C25—N4	−177.2 (3)
C2—C3—C12—C7	−176.2 (3)	C24—C25—C26—C27	−0.1 (5)
C8—C7—C12—C11	−0.7 (5)	N4—C25—C26—C27	177.5 (3)
C6—C7—C12—C11	178.2 (3)	C25—C26—C27—C22	−1.2 (5)
C8—C7—C12—C3	178.8 (3)	C23—C22—C27—C26	2.2 (5)
C6—C7—C12—C3	−2.3 (5)	C21—C22—C27—C26	−175.3 (3)
C2—N1—C13—O2	−179.9 (3)	C24—C25—N4—O6	−0.8 (5)
C14—N1—C13—O2	2.1 (5)	C26—C25—N4—O6	−178.5 (4)
C2—N1—C13—C11	1.1 (5)	C24—C25—N4—O5	177.4 (4)
C14—N1—C13—C11	−176.9 (3)	C26—C25—N4—O5	−0.3 (5)
C10—C11—C13—O2	−2.5 (5)

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the p-nitrophenyl (C22–C27) ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1S	0.80	1.99	2.764 (4)	163
C8—H8···Cgⁱ	0.93	2.90	3.799 (6)	162

Symmetry code: (i) −x+2, −y+2, −z+2.

Experimental details

Crystal data
Chemical formula	C₂₆H₁₈N₄O₆S·C₂H₆OS
M_r	592.63
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.152 (1), 11.971 (1), 13.910 (1)
α, β, γ (°)	107.268 (7), 101.789 (7), 96.319 (8)
V (Å³)	1400.6 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.24
Crystal size (mm)	0.50 × 0.16 × 0.13

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	5055, 4737, 3075
R_int	0.017
(sin θ/λ)_max (Å⁻¹)	0.596

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.052, 0.163, 1.04
No. of reflections	4737
No. of parameters	371
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.73, −0.43

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), HELENA (Spek, 1996), SIR97 (Altomare et al., 1999), SHELXL97 (Sheldrick, 2008), PLATON (Spek, 2009) and Mercury (Macrae et al., 2006).

Hydrogen-bond geometry (Å, º) top

Cg is the centroid of the p-nitrophenyl (C22–C27) ring.

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2N···O1S	0.80	1.99	2.764 (4)	163
C8—H8···Cgⁱ	0.93	2.903	3.799 (6)	162

Symmetry code: (i) −x+2, −y+2, −z+2.

Acknowledgements

The authors thank CAPES and CNPq for financial support.

References

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Volume 67| Part 3| March 2011| Pages o627-o628

doi:10.1107/S1600536811004697

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

4-[(1,3-Dioxo-2,3-di­hydro-1H-benzo[de]isoquinolin-2-yl)meth­yl]-N′-[(E)-4-nitro­benzyl­­idene]benzene­sulfono­hydrazide di­methyl sulfoxide monosolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

4-[(1,3-Dioxo-2,3-dihydro-1H-benzo[de]isoquinolin-2-yl)methyl]-N′-[(E)-4-nitrobenzylidene]benzenesulfonohydrazide dimethyl sulfoxide monosolvate