5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazo­cine-6,12-dione acetic acid hemisolvate

Abbassi, N.; Bassou, O.; Rakib, E.M.; Saadi, M.; El Ammari, L.

doi:10.1107/S1600536813007903

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 69| Part 4| April 2013| Pages o614-o615

doi:10.1107/S1600536813007903

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5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione acetic acid hemisolvate

Najat Abbassi,^a ^* Oulemda Bassou,^a El Mostapha Rakib,^a Mohamed Saadi ^b and Lahcen El Ammari ^b

^aLaboratoire de Chimie Organique et Analytique, Université Sultan Moulay Slimane, Faculté des Sciences et Techniques, Béni-Mellal, BP 523, Morocco, and ^bLaboratoire de Chimie du Solide Appliquée, Faculté des Sciences, Université Mohammed V-Agdal, Avenue Ibn Battouta, BP 1014, Rabat, Morocco
^*Correspondence e-mail: najat_abbassi@hotmail.com

(Received 27 February 2013; accepted 21 March 2013; online 28 March 2013)

The molecular structure of the title compound, C₂₈H₂₂N₂O₆S₂·0.5CH₃COOH, is built up from three fused rings, two six and one eight membered. The eight-membered ring shows a boat conformation and the dihedral angle between the two benzene groups attached thereto is 66.43 (11)°, resulting in a V-shaped geometry. Two tosyl substituents are bound to the N atoms. The planes through the tolyl rings are roughly perpendicular, as indicated by the dihedral angle of 82.44 (12)°. In the crystal, the molecule and its inversion-related symmetry-equivalent are linked to the acetic acid solvent molecule by non-classical O—H⋯O and C—H⋯O hydrogen bonds. Two half-occupied acetic acid solvent molecules are disordered at the same site and linked by a center of symmetry.

Related literature

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010 ); Drew (2000 ); Garaj et al. (2005 ). For their antiproliferative activity, see: Abbassi et al. (2012 ); Bouissane et al. (2006 ); Lopez et al. (2010 ). For puckering parameters, see: Cremer & Pople (1975 ).

Experimental

Crystal data

C₂₈H₂₂N₂O₆S₂·0.5C₂H₄O₂
M_r = 576.62
Triclinic, $[P \overline 1]$
a = 8.6933 (11) Å
b = 11.1746 (18) Å
c = 14.8051 (19) Å
α = 87.042 (4)°
β = 74.370 (5)°
γ = 75.097 (4)°
V = 1338.2 (3) Å³
Z = 2
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 296 K
0.41 × 0.35 × 0.27 mm

Data collection

Bruker X8 APEX diffractometer
19664 measured reflections
5446 independent reflections
4262 reflections with I > 2σ(I)
R_int = 0.039

Refinement

R[F² > 2σ(F²)] = 0.042
wR(F²) = 0.114
S = 1.02
5446 reflections
370 parameters
H-atom parameters constrained
Δρ_max = 0.41 e Å⁻³
Δρ_min = −0.47 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O8—H8⋯O3	0.95	2.66	3.460 (3)	142
C30—H30C⋯O3ⁱ	0.96	2.71	3.473 (5)	136
C16—H16⋯O2	0.93	2.49	3.190 (3)	132
C11—H11⋯O4ⁱⁱ	0.93	2.54	3.241 (2)	133
Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) 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, 2012 ); software used to prepare material for publication: PLATON (Spek, 2009 ) and publCIF (Westrip, 2010 ).

Supporting information

Crystal structure: contains datablock global. DOI: 10.1107/S1600536813007903/im2423sup1.cif

checkCIF report

Comment top

Sulfonamides constitute an important class of drugs. They possess various types of pharmacological activities such as antibacterial, hypoglycemic, anti-inflammatory, and antitumor (Lopez, et al., 2010), as well as anti-carbonic anhydrase (Brzozowski, et al., 2010), hypoglycemic (Drew, 2000), and anticancer activity (Garaj, et al., 2005). The present work is part of research concerning the synthesis of some new N-(6 (4)-indazolyl)arylsulfonamide derivatives reported recently by our group. Some of these compounds showed an important antiproliferative activity against some human and murine cell lines (Abbassi, et al., 2012, Bouissane et al., 2006).

The three fused six- and eight-membered rings in the molecule of the title compound, are linked to two tolyl rings by sulfonyl groups as shown in Fig.1. The eight-membered ring displays a boat conformation, as indicated by the total puckering amplitude QT = 1.4807 (22) Å and spherical polar angles θ2 = 89.89 (8) and θ3 = 177 (3)° (Cremer & Pople, 1975). The dihedral angle between the two phenyl groups attached to the boat ring is 66.43 (11)°, resulting in a V shaped geometry. The planes through the two tolyl rings (C15 to C20) and (C22 to C27) are almost perpendicular as indicated by the dihedral angle between them of 82.44 (12)°.

In the crystal, each molecule and its symmetry through the inversion center are linked to the acetic acid solvent by O8—H8···O3, C30—H30c···O3ⁱ, C16—H16···O2 and C11—H11···O4ⁱⁱ non-classical hydrogen bonds (Table 2).

Two half acetic acid solvent molecules are disordered at the same site of the crystal structure and linked by a center of symmetry.

Related literature top

For the pharmacological activity of sulfonamides, see: Brzozowski et al. (2010); Drew (2000); Garaj et al. (2005). For their antiproliferative activity, see: Abbassi et al. (2012); Bouissane et al. (2006); Lopez et al. (2010). For puckering parameters, see: Cremer & Pople (1975).

Experimental top

A mixture of 2-nitrobenzaldehyde (1.22 mmol) and anhydrous SnCl₂ (1.1 g, 6.1 mmol) in 25 mL of absolute ethanol was stirred for 1 h. After reduction, the starting material disappeared, and the solution was allowed to cool down. The pH was adjusted to 7–8 by addition of 5% aqueous potassium bicarbonate before extraction with ethyl acetate. The organic phase was washed with brine and dried over magnesium sulfate. The solvent was removed to afford the amine, which was immediately dissolved in pyridine (5 ml) and then reacted with 4-methylbenzenesulfonyl chloride (0.26 g, 1.25 mmol) at room temperature for 24 h. After the reaction mixture was concentrated in vacuo, the resulting residue was purified by flash chromatography (eluted with ethyl acetate : hexane 3:7). Colourless prisms of the title compound suitable for X-ray structure determination were collected after recrystallization from ethyl acetate : hexane (3:7 v/v) by slow evaporation of the solvent at room temperature after some days.

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, 2012); software used to prepare material for publication: PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Figures top

Fig. 1. Molecular structure of the title compound with the atom-labelling scheme. Displacement ellipsoids are drawn at the 50% probability level. H atoms are represented as small circles.

5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione acetic acid hemisolvate top

Crystal data top

C₂₈H₂₂N₂O₆S₂·0.5C₂H₄O₂	Z = 2
M_r = 576.62	F(000) = 600
Triclinic, P1	D_x = 1.431 Mg m⁻³
Hall symbol: -p 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.6933 (11) Å	Cell parameters from 5446 reflections
b = 11.1746 (18) Å	θ = 2.4–26.4°
c = 14.8051 (19) Å	µ = 0.25 mm⁻¹
α = 87.042 (4)°	T = 296 K
β = 74.370 (5)°	Prismatic, colourless
γ = 75.097 (4)°	0.41 × 0.35 × 0.27 mm
V = 1338.2 (3) Å³

Data collection top

Bruker X8 APEX diffractometer	4262 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.039
Graphite monochromator	θ_max = 26.4°, θ_min = 2.4°
ϕ and ω scans	h = −10→8
19664 measured reflections	k = −13→13
5447 independent reflections	l = −18→18

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)] = 0.042	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0555P)² + 0.7987P] where P = (F_o² + 2F_c²)/3
5446 reflections	(Δ/σ)_max = 0.001
370 parameters	Δρ_max = 0.41 e Å⁻³
0 restraints	Δρ_min = −0.47 e Å⁻³

Crystal data top

C₂₈H₂₂N₂O₆S₂·0.5C₂H₄O₂	γ = 75.097 (4)°
M_r = 576.62	V = 1338.2 (3) Å³
Triclinic, P1	Z = 2
a = 8.6933 (11) Å	Mo Kα radiation
b = 11.1746 (18) Å	µ = 0.25 mm⁻¹
c = 14.8051 (19) Å	T = 296 K
α = 87.042 (4)°	0.41 × 0.35 × 0.27 mm
β = 74.370 (5)°

Data collection top

Bruker X8 APEX diffractometer	4262 reflections with I > 2σ(I)
19664 measured reflections	R_int = 0.039
5447 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.042	0 restraints
wR(F²) = 0.114	H-atom parameters constrained
S = 1.02	Δρ_max = 0.41 e Å⁻³
5446 reflections	Δρ_min = −0.47 e Å⁻³
370 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 F² against all reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) 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	Occ. (<1)
C1	0.1314 (2)	0.04736 (19)	0.66644 (14)	0.0182 (4)
C2	0.1389 (3)	−0.0156 (2)	0.58638 (15)	0.0243 (5)
H2	0.1228	0.0280	0.5331	0.029*
C3	0.1703 (3)	−0.1427 (2)	0.58609 (16)	0.0325 (5)
H3	0.1734	−0.1850	0.5329	0.039*
C4	0.1973 (3)	−0.2080 (2)	0.66490 (16)	0.0352 (6)
H4	0.2197	−0.2940	0.6642	0.042*
C5	0.1909 (3)	−0.1454 (2)	0.74484 (15)	0.0247 (5)
H5	0.2103	−0.1896	0.7973	0.030*
C6	0.1555 (2)	−0.01681 (19)	0.74673 (14)	0.0176 (4)
C7	0.1413 (2)	0.04925 (19)	0.83511 (14)	0.0169 (4)
C8	−0.1527 (2)	0.13023 (18)	0.83944 (13)	0.0152 (4)
C9	−0.2611 (2)	0.06755 (18)	0.89469 (14)	0.0171 (4)
H9	−0.2425	0.0310	0.9499	0.021*
C10	−0.3982 (2)	0.06016 (19)	0.86638 (14)	0.0205 (4)
H10	−0.4706	0.0166	0.9021	0.025*
C11	−0.4279 (3)	0.1172 (2)	0.78530 (14)	0.0224 (5)
H11	−0.5206	0.1123	0.7672	0.027*
C12	−0.3208 (2)	0.1815 (2)	0.73125 (14)	0.0209 (4)
H12	−0.3419	0.2204	0.6772	0.025*
C13	−0.1806 (2)	0.18787 (18)	0.75783 (14)	0.0175 (4)
C14	−0.0645 (3)	0.2544 (2)	0.69667 (15)	0.0232 (5)
C15	0.2483 (3)	0.24962 (19)	0.48932 (14)	0.0194 (4)
C16	0.1234 (3)	0.3396 (2)	0.46486 (16)	0.0274 (5)
H16	0.0445	0.3938	0.5101	0.033*
C17	0.1187 (3)	0.3471 (2)	0.37219 (17)	0.0303 (5)
H17	0.0352	0.4066	0.3552	0.036*
C18	0.2361 (3)	0.2677 (2)	0.30412 (15)	0.0250 (5)
C19	0.3592 (3)	0.1785 (2)	0.33051 (16)	0.0278 (5)
H19	0.4384	0.1247	0.2852	0.033*
C20	0.3662 (3)	0.1682 (2)	0.42303 (15)	0.0268 (5)
H20	0.4485	0.1078	0.4402	0.032*
C21	0.2294 (3)	0.2763 (2)	0.20329 (17)	0.0356 (6)
H21A	0.3194	0.2144	0.1662	0.053*
H21B	0.2377	0.3570	0.1804	0.053*
H21C	0.1267	0.2630	0.1991	0.053*
C22	0.1091 (2)	0.31288 (19)	0.92998 (14)	0.0195 (4)
C23	0.0855 (3)	0.4133 (2)	0.87229 (18)	0.0333 (6)
H23	−0.0072	0.4346	0.8492	0.040*
C24	0.2022 (3)	0.4814 (2)	0.8495 (2)	0.0395 (6)
H24	0.1867	0.5494	0.8111	0.047*
C25	0.3419 (3)	0.4508 (2)	0.88264 (18)	0.0324 (6)
C26	0.3612 (3)	0.3508 (2)	0.94126 (17)	0.0292 (5)
H26	0.4532	0.3301	0.9650	0.035*
C27	0.2464 (3)	0.2812 (2)	0.96518 (15)	0.0239 (5)
H27	0.2611	0.2139	1.0044	0.029*
C28	0.4722 (3)	0.5229 (3)	0.8558 (2)	0.0508 (8)
H28A	0.4406	0.5887	0.8150	0.076*
H28B	0.5760	0.4687	0.8241	0.076*
H28C	0.4827	0.5571	0.9113	0.076*
O8	0.4362 (4)	0.5295 (3)	0.47416 (19)	0.0648 (8)	0.50
H8	0.3384	0.5054	0.5060	0.097*	0.50
C29	0.4362 (4)	0.5295 (3)	0.47416 (19)	0.0648 (8)	0.50
C30	0.4689 (5)	0.4823 (4)	0.3786 (3)	0.0253 (9)	0.50
H30A	0.3799	0.5254	0.3529	0.038*	0.50
H30B	0.4762	0.3951	0.3790	0.038*	0.50
H30C	0.5707	0.4971	0.3408	0.038*	0.50
O7	0.3037 (5)	0.5905 (3)	0.5167 (3)	0.0489 (10)	0.50
N1	0.0986 (2)	0.18137 (16)	0.66594 (12)	0.0186 (4)
N2	−0.00829 (19)	0.13646 (15)	0.86839 (11)	0.0164 (4)
O1	0.25131 (17)	0.03120 (13)	0.87404 (10)	0.0209 (3)
O2	−0.1071 (2)	0.36032 (16)	0.67434 (14)	0.0436 (5)
O3	0.2235 (2)	0.36337 (15)	0.64412 (11)	0.0315 (4)
O4	0.40207 (18)	0.15004 (16)	0.61277 (11)	0.0303 (4)
O5	−0.20005 (18)	0.30902 (15)	0.96957 (11)	0.0310 (4)
O6	−0.0125 (2)	0.15277 (15)	1.04057 (10)	0.0287 (4)
S1	0.25694 (6)	0.24198 (5)	0.60663 (4)	0.02218 (14)
S2	−0.04108 (6)	0.22883 (5)	0.96340 (4)	0.02004 (14)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
C1	0.0126 (10)	0.0221 (11)	0.0204 (10)	−0.0069 (8)	−0.0035 (8)	0.0043 (8)
C2	0.0239 (11)	0.0320 (12)	0.0178 (10)	−0.0102 (10)	−0.0045 (9)	0.0051 (9)
C3	0.0425 (14)	0.0328 (13)	0.0190 (11)	−0.0085 (11)	−0.0029 (10)	−0.0051 (9)
C4	0.0491 (16)	0.0214 (12)	0.0251 (12)	−0.0001 (11)	−0.0009 (11)	−0.0022 (9)
C5	0.0255 (12)	0.0243 (12)	0.0178 (10)	0.0008 (9)	−0.0021 (9)	0.0038 (9)
C6	0.0110 (9)	0.0225 (11)	0.0175 (10)	−0.0033 (8)	−0.0022 (8)	0.0030 (8)
C7	0.0134 (10)	0.0202 (10)	0.0186 (10)	−0.0086 (8)	−0.0038 (8)	0.0069 (8)
C8	0.0105 (9)	0.0169 (10)	0.0200 (10)	−0.0036 (8)	−0.0066 (8)	−0.0015 (8)
C9	0.0145 (10)	0.0211 (10)	0.0168 (10)	−0.0056 (8)	−0.0051 (8)	0.0009 (8)
C10	0.0139 (10)	0.0264 (11)	0.0235 (11)	−0.0101 (9)	−0.0042 (8)	0.0016 (9)
C11	0.0160 (10)	0.0329 (12)	0.0224 (11)	−0.0096 (9)	−0.0085 (8)	0.0006 (9)
C12	0.0176 (10)	0.0272 (12)	0.0196 (10)	−0.0046 (9)	−0.0093 (8)	0.0036 (8)
C13	0.0132 (10)	0.0168 (10)	0.0223 (10)	−0.0036 (8)	−0.0049 (8)	0.0013 (8)
C14	0.0197 (11)	0.0251 (12)	0.0279 (11)	−0.0085 (9)	−0.0097 (9)	0.0078 (9)
C15	0.0216 (11)	0.0240 (11)	0.0187 (10)	−0.0144 (9)	−0.0092 (8)	0.0095 (8)
C16	0.0365 (13)	0.0183 (11)	0.0285 (12)	−0.0044 (10)	−0.0131 (10)	0.0013 (9)
C17	0.0431 (14)	0.0190 (11)	0.0345 (13)	−0.0049 (10)	−0.0237 (11)	0.0059 (9)
C18	0.0340 (13)	0.0258 (12)	0.0243 (11)	−0.0173 (10)	−0.0149 (10)	0.0079 (9)
C19	0.0229 (11)	0.0371 (13)	0.0230 (11)	−0.0092 (10)	−0.0043 (9)	0.0027 (10)
C20	0.0164 (11)	0.0371 (13)	0.0271 (12)	−0.0072 (10)	−0.0075 (9)	0.0094 (10)
C21	0.0499 (16)	0.0386 (14)	0.0274 (12)	−0.0171 (12)	−0.0204 (11)	0.0054 (10)
C22	0.0189 (10)	0.0189 (10)	0.0235 (10)	−0.0088 (8)	−0.0062 (8)	−0.0018 (8)
C23	0.0315 (13)	0.0292 (13)	0.0463 (15)	−0.0118 (11)	−0.0201 (11)	0.0097 (11)
C24	0.0443 (16)	0.0269 (13)	0.0523 (16)	−0.0172 (12)	−0.0155 (13)	0.0126 (12)
C25	0.0271 (13)	0.0231 (12)	0.0455 (15)	−0.0120 (10)	−0.0002 (11)	−0.0082 (10)
C26	0.0215 (11)	0.0292 (12)	0.0418 (14)	−0.0104 (10)	−0.0111 (10)	−0.0081 (10)
C27	0.0258 (12)	0.0239 (11)	0.0278 (11)	−0.0102 (9)	−0.0127 (9)	−0.0005 (9)
C28	0.0350 (15)	0.0342 (15)	0.081 (2)	−0.0223 (13)	0.0026 (14)	−0.0080 (14)
O8	0.0622 (18)	0.081 (2)	0.0552 (17)	−0.0210 (16)	−0.0189 (14)	−0.0014 (15)
C29	0.0622 (18)	0.081 (2)	0.0552 (17)	−0.0210 (16)	−0.0189 (14)	−0.0014 (15)
C30	0.020 (2)	0.024 (2)	0.031 (2)	−0.0067 (18)	−0.0053 (18)	0.0017 (18)
O7	0.042 (2)	0.036 (2)	0.048 (2)	0.0165 (18)	0.0000 (18)	−0.0187 (18)
N1	0.0158 (9)	0.0224 (9)	0.0197 (9)	−0.0085 (7)	−0.0056 (7)	0.0066 (7)
N2	0.0119 (8)	0.0215 (9)	0.0184 (8)	−0.0061 (7)	−0.0063 (6)	−0.0018 (7)
O1	0.0144 (7)	0.0274 (8)	0.0258 (8)	−0.0099 (6)	−0.0107 (6)	0.0090 (6)
O2	0.0271 (9)	0.0274 (10)	0.0717 (13)	−0.0078 (7)	−0.0091 (9)	0.0254 (9)
O3	0.0396 (10)	0.0400 (10)	0.0240 (8)	−0.0280 (8)	−0.0070 (7)	0.0044 (7)
O4	0.0172 (8)	0.0515 (11)	0.0263 (8)	−0.0142 (7)	−0.0102 (6)	0.0159 (7)
O5	0.0176 (8)	0.0341 (9)	0.0403 (10)	−0.0046 (7)	−0.0046 (7)	−0.0164 (7)
O6	0.0370 (9)	0.0392 (9)	0.0173 (8)	−0.0229 (8)	−0.0071 (7)	0.0027 (7)
S1	0.0199 (3)	0.0336 (3)	0.0191 (3)	−0.0163 (2)	−0.0078 (2)	0.0087 (2)
S2	0.0173 (3)	0.0259 (3)	0.0197 (3)	−0.0102 (2)	−0.0041 (2)	−0.0039 (2)

Geometric parameters (Å, º) top

C1—C2	1.387 (3)	C18—C21	1.507 (3)
C1—C6	1.393 (3)	C19—C20	1.385 (3)
C1—N1	1.451 (3)	C19—H19	0.9300
C2—C3	1.376 (3)	C20—H20	0.9300
C2—H2	0.9300	C21—H21A	0.9600
C3—C4	1.386 (3)	C21—H21B	0.9600
C3—H3	0.9300	C21—H21C	0.9600
C4—C5	1.387 (3)	C22—C23	1.381 (3)
C4—H4	0.9300	C22—C27	1.386 (3)
C5—C6	1.390 (3)	C22—S2	1.751 (2)
C5—H5	0.9300	C23—C24	1.382 (3)
C6—C7	1.496 (3)	C23—H23	0.9300
C7—O1	1.214 (2)	C24—C25	1.386 (4)
C7—N2	1.392 (3)	C24—H24	0.9300
C8—C9	1.383 (3)	C25—C26	1.382 (3)
C8—C13	1.390 (3)	C25—C28	1.511 (3)
C8—N2	1.450 (2)	C26—C27	1.382 (3)
C9—C10	1.388 (3)	C26—H26	0.9300
C9—H9	0.9300	C27—H27	0.9300
C10—C11	1.385 (3)	C28—H28A	0.9600
C10—H10	0.9300	C28—H28B	0.9600
C11—C12	1.380 (3)	C28—H28C	0.9600
C11—H11	0.9300	O8—O7	1.199 (4)
C12—C13	1.397 (3)	O8—C30	1.465 (5)
C12—H12	0.9300	O8—O8ⁱ	1.510 (5)
C13—C14	1.488 (3)	O8—H8	0.9518
C14—O2	1.203 (3)	C30—H30A	0.9600
C14—N1	1.407 (3)	C30—H30B	0.9600
C15—C20	1.382 (3)	C30—H30C	0.9600
C15—C16	1.391 (3)	O7—H8	0.9283
C15—S1	1.755 (2)	N1—S1	1.7000 (17)
C16—C17	1.381 (3)	N2—S2	1.7052 (17)
C16—H16	0.9300	O3—S1	1.4215 (17)
C17—C18	1.384 (3)	O4—S1	1.4287 (16)
C17—H17	0.9300	O5—S2	1.4229 (16)
C18—C19	1.389 (3)	O6—S2	1.4260 (16)

C2—C1—C6	120.69 (19)	C18—C21—H21B	109.5
C2—C1—N1	119.37 (18)	H21A—C21—H21B	109.5
C6—C1—N1	119.95 (18)	C18—C21—H21C	109.5
C3—C2—C1	119.8 (2)	H21A—C21—H21C	109.5
C3—C2—H2	120.1	H21B—C21—H21C	109.5
C1—C2—H2	120.1	C23—C22—C27	120.87 (19)
C2—C3—C4	120.2 (2)	C23—C22—S2	119.55 (16)
C2—C3—H3	119.9	C27—C22—S2	119.52 (16)
C4—C3—H3	119.9	C22—C23—C24	118.8 (2)
C3—C4—C5	120.1 (2)	C22—C23—H23	120.6
C3—C4—H4	119.9	C24—C23—H23	120.6
C5—C4—H4	119.9	C23—C24—C25	121.6 (2)
C4—C5—C6	120.2 (2)	C23—C24—H24	119.2
C4—C5—H5	119.9	C25—C24—H24	119.2
C6—C5—H5	119.9	C26—C25—C24	118.4 (2)
C5—C6—C1	118.95 (19)	C26—C25—C28	119.8 (2)
C5—C6—C7	119.38 (17)	C24—C25—C28	121.8 (2)
C1—C6—C7	121.67 (18)	C27—C26—C25	121.2 (2)
O1—C7—N2	122.21 (19)	C27—C26—H26	119.4
O1—C7—C6	123.48 (18)	C25—C26—H26	119.4
N2—C7—C6	114.29 (16)	C26—C27—C22	119.2 (2)
C9—C8—C13	121.32 (17)	C26—C27—H27	120.4
C9—C8—N2	118.90 (17)	C22—C27—H27	120.4
C13—C8—N2	119.78 (17)	C25—C28—H28A	109.5
C8—C9—C10	118.93 (18)	C25—C28—H28B	109.5
C8—C9—H9	120.5	H28A—C28—H28B	109.5
C10—C9—H9	120.5	C25—C28—H28C	109.5
C11—C10—C9	120.46 (19)	H28A—C28—H28C	109.5
C11—C10—H10	119.8	H28B—C28—H28C	109.5
C9—C10—H10	119.8	O7—O8—C30	122.8 (3)
C12—C11—C10	120.37 (18)	O7—O8—O8ⁱ	119.8 (4)
C12—C11—H11	119.8	C30—O8—O8ⁱ	115.6 (3)
C10—C11—H11	119.8	O7—O8—H8	49.5
C11—C12—C13	119.90 (18)	C30—O8—H8	102.6
C11—C12—H12	120.0	O8ⁱ—O8—H8	106.1
C13—C12—H12	120.0	O8—C30—H30A	108.4
C8—C13—C12	119.01 (18)	O8—C30—H30B	110.4
C8—C13—C14	122.23 (17)	H30A—C30—H30B	109.5
C12—C13—C14	118.75 (18)	O8—C30—H30C	109.6
O2—C14—N1	123.2 (2)	H30A—C30—H30C	109.5
O2—C14—C13	123.0 (2)	H30B—C30—H30C	109.5
N1—C14—C13	113.85 (17)	O8—O7—H8	51.3
C20—C15—C16	121.33 (19)	C14—N1—C1	119.97 (16)
C20—C15—S1	119.85 (16)	C14—N1—S1	122.16 (14)
C16—C15—S1	118.81 (17)	C1—N1—S1	116.64 (13)
C17—C16—C15	118.7 (2)	C7—N2—C8	120.46 (16)
C17—C16—H16	120.6	C7—N2—S2	120.92 (13)
C15—C16—H16	120.6	C8—N2—S2	116.82 (13)
C16—C17—C18	121.2 (2)	O3—S1—O4	120.61 (10)
C16—C17—H17	119.4	O3—S1—N1	106.68 (9)
C18—C17—H17	119.4	O4—S1—N1	104.34 (9)
C17—C18—C19	118.8 (2)	O3—S1—C15	110.00 (10)
C17—C18—C21	120.8 (2)	O4—S1—C15	108.42 (10)
C19—C18—C21	120.4 (2)	N1—S1—C15	105.68 (9)
C20—C19—C18	121.2 (2)	O5—S2—O6	119.90 (10)
C20—C19—H19	119.4	O5—S2—N2	103.20 (8)
C18—C19—H19	119.4	O6—S2—N2	109.03 (9)
C15—C20—C19	118.7 (2)	O5—S2—C22	109.77 (10)
C15—C20—H20	120.7	O6—S2—C22	109.15 (10)
C19—C20—H20	120.7	N2—S2—C22	104.62 (9)
C18—C21—H21A	109.5

C6—C1—C2—C3	0.1 (3)	C24—C25—C26—C27	1.2 (4)
N1—C1—C2—C3	179.86 (19)	C28—C25—C26—C27	−178.4 (2)
C1—C2—C3—C4	−1.2 (4)	C25—C26—C27—C22	−0.4 (3)
C2—C3—C4—C5	0.7 (4)	C23—C22—C27—C26	−0.5 (3)
C3—C4—C5—C6	0.8 (4)	S2—C22—C27—C26	−177.60 (17)
C4—C5—C6—C1	−1.8 (3)	O2—C14—N1—C1	−158.1 (2)
C4—C5—C6—C7	177.1 (2)	C13—C14—N1—C1	20.7 (3)
C2—C1—C6—C5	1.4 (3)	O2—C14—N1—S1	8.8 (3)
N1—C1—C6—C5	−178.39 (18)	C13—C14—N1—S1	−172.40 (14)
C2—C1—C6—C7	−177.50 (18)	C2—C1—N1—C14	92.5 (2)
N1—C1—C6—C7	2.7 (3)	C6—C1—N1—C14	−87.8 (2)
C5—C6—C7—O1	57.8 (3)	C2—C1—N1—S1	−75.2 (2)
C1—C6—C7—O1	−123.3 (2)	C6—C1—N1—S1	104.62 (18)
C5—C6—C7—N2	−123.7 (2)	O1—C7—N2—C8	−160.90 (18)
C1—C6—C7—N2	55.2 (2)	C6—C7—N2—C8	20.6 (2)
C13—C8—C9—C10	1.5 (3)	O1—C7—N2—S2	3.3 (3)
N2—C8—C9—C10	−179.16 (17)	C6—C7—N2—S2	−175.14 (13)
C8—C9—C10—C11	−1.6 (3)	C9—C8—N2—C7	93.3 (2)
C9—C10—C11—C12	0.5 (3)	C13—C8—N2—C7	−87.3 (2)
C10—C11—C12—C13	0.7 (3)	C9—C8—N2—S2	−71.5 (2)
C9—C8—C13—C12	−0.3 (3)	C13—C8—N2—S2	107.86 (18)
N2—C8—C13—C12	−179.68 (18)	C14—N1—S1—O3	34.98 (18)
C9—C8—C13—C14	−179.19 (19)	C1—N1—S1—O3	−157.71 (14)
N2—C8—C13—C14	1.5 (3)	C14—N1—S1—O4	163.68 (16)
C11—C12—C13—C8	−0.8 (3)	C1—N1—S1—O4	−29.01 (16)
C11—C12—C13—C14	178.13 (19)	C14—N1—S1—C15	−82.08 (18)
C8—C13—C14—O2	−125.5 (2)	C1—N1—S1—C15	85.23 (15)
C12—C13—C14—O2	55.7 (3)	C20—C15—S1—O3	137.50 (17)
C8—C13—C14—N1	55.7 (3)	C16—C15—S1—O3	−41.45 (19)
C12—C13—C14—N1	−123.1 (2)	C20—C15—S1—O4	3.7 (2)
C20—C15—C16—C17	−0.2 (3)	C16—C15—S1—O4	−175.27 (16)
S1—C15—C16—C17	178.73 (17)	C20—C15—S1—N1	−107.71 (18)
C15—C16—C17—C18	−0.5 (3)	C16—C15—S1—N1	73.34 (18)
C16—C17—C18—C19	0.6 (3)	C7—N2—S2—O5	175.75 (15)
C16—C17—C18—C21	179.7 (2)	C8—N2—S2—O5	−19.48 (16)
C17—C18—C19—C20	−0.1 (3)	C7—N2—S2—O6	−55.75 (17)
C21—C18—C19—C20	−179.2 (2)	C8—N2—S2—O6	109.02 (15)
C16—C15—C20—C19	0.7 (3)	C7—N2—S2—C22	60.89 (17)
S1—C15—C20—C19	−178.24 (17)	C8—N2—S2—C22	−134.34 (15)
C18—C19—C20—C15	−0.5 (3)	C23—C22—S2—O5	−31.5 (2)
C27—C22—C23—C24	0.5 (4)	C27—C22—S2—O5	145.58 (17)
S2—C22—C23—C24	177.5 (2)	C23—C22—S2—O6	−164.81 (18)
C22—C23—C24—C25	0.4 (4)	C27—C22—S2—O6	12.3 (2)
C23—C24—C25—C26	−1.3 (4)	C23—C22—S2—N2	78.6 (2)
C23—C24—C25—C28	178.3 (3)	C27—C22—S2—N2	−104.27 (18)

Symmetry code: (i) −x+1, −y+1, −z+1.

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O3	0.95	2.66	3.460 (3)	142
C30—H30C···O3ⁱ	0.96	2.71	3.473 (5)	136
C16—H16···O2	0.93	2.49	3.190 (3)	132
C11—H11···O4ⁱⁱ	0.93	2.54	3.241 (2)	133

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

Experimental details

Crystal data
Chemical formula	C₂₈H₂₂N₂O₆S₂·0.5C₂H₄O₂
M_r	576.62
Crystal system, space group	Triclinic, P1
Temperature (K)	296
a, b, c (Å)	8.6933 (11), 11.1746 (18), 14.8051 (19)
α, β, γ (°)	87.042 (4), 74.370 (5), 75.097 (4)
V (Å³)	1338.2 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
Crystal size (mm)	0.41 × 0.35 × 0.27

Data collection
Diffractometer	Bruker X8 APEX diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	19664, 5447, 4262
R_int	0.039
(sin θ/λ)_max (Å⁻¹)	0.625

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.042, 0.114, 1.02
No. of reflections	5446
No. of parameters	370
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.41, −0.47

Computer programs: APEX2 (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 for Windows (Farrugia, 2012), PLATON (Spek, 2009) and publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
O8—H8···O3	0.95	2.66	3.460 (3)	141.9
C30—H30C···O3ⁱ	0.96	2.71	3.473 (5)	136.4
C16—H16···O2	0.93	2.49	3.190 (3)	131.7
C11—H11···O4ⁱⁱ	0.93	2.54	3.241 (2)	132.7

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

Acknowledgements

The authors thank the Unit of Support for Technical and Scientific Research (UATRS, CNRST) for the X-ray measurements.

References

Abbassi, N., Chicha, H., Rakib, E. M., Hannioui, A., Alaoui, M., Hajjaji, A., Geffken, D., Aiello, C., Gangemi, R., Rosano, C. & Viale, M. (2012). Eur. J. Med. Chem. 57, 240–249. Web of Science CrossRef CAS PubMed Google Scholar
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Volume 69| Part 4| April 2013| Pages o614-o615

doi:10.1107/S1600536813007903

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

5,11-Di­tosyl-5H,11H-dibenzo[b,f][1,5]diazo­cine-6,12-dione acetic acid hemisolvate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

5,11-Ditosyl-5H,11H-dibenzo[b,f][1,5]diazocine-6,12-dione acetic acid hemisolvate