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In the crystal structure of the novel acyl­thio­carbamate derivative O-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)­ethyl] N-(4-methyl­phenyl)-N-(3-nitro­benzoyl)thio­carbamate, C25H19N3O6S, intra- and inter­molecular [pi]-[pi] inter­actions occur between the phthalimide and N-benzoyl moieties. The partial atomic charges, calculated by ab initio methods, are consistent with the observed structure.

Supporting information

cif

Crystallographic Information File (CIF) https://doi.org/10.1107/S0108270106013175/tr1130sup1.cif
Contains datablocks global, I

hkl

Structure factor file (CIF format) https://doi.org/10.1107/S0108270106013175/tr1130Isup2.hkl
Contains datablock I

CCDC reference: 612448

Comment top

Acylthiocarbamates (ATCs) represent a novel chemical class, synthesized through an original highly convergent one-pot three-step procedure that combines, sequentially and covalently, three types of building blocks, namely alcohols, isothiocyanates and acyl chlorides (Ranize et al., 2003). ATCs have proved to be a new class of HIV-1 non-nucleoside reverse transcriptase inhibitors (NNRTIs), structurally related to N-phenyl-N-thiazolylthiourea derivatives. A structure-based optimization strategy led to the identification of O-(2-phthalimidoethyl) ATCs, which proved to be active at low nanomolar concentrations. Docking simulations suggest that phthalimidoethyl ATCs do not share the bioactive `butterfly like' conformation typical of first-generation NNRTIs. According to this model, the ethyl linker would assume an extended conformation, with the N-phenyl and N-acyl moieties positioned at nearly 90° and located at the top of the allosteric binding site RT, while the phthalimide framework would be positioned at the entrance of the cavity.

In order to characterize this novel class of potent NNRTIs at the atomic level, and to provide insights for further chemical modifications, the crystal structure of (I), O-[2-(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl] N-(4-methylphenyl)-N-(3-nitrobenzoyl)thiocarbamate, one of the most potent ATCs currently available (EC50 = 20 nM; Cesarini et al., 2003), has been determined by single-crystal X-ray analysis and the results are presented here.

The structure of (I) is shown in Fig. 1, where the labels A, B and C are used to specify the ring moieties, as follows: 5A is the five-membered ring defined by atoms C1/N1/C8/C7/C2, 6A is the fused aromatic ring defined by atoms C2/C3/C4/C5/C6/C7, B is the 3-nitro benzoyl ring and C is the methylphenyl ring. The shape of (I) is horseshoe-like, with the phthalimide and 3-nitrobenzoyl groups facing each other. The `linker' connecting these two ring systems is formed by atoms C9/C10/O3/C11/N2/C19 and contains an acylthiocarbamic group. The C11—O3 bond distance is in agreement with the value found in an analogous structure of a secondary N-phenyl thiocarbamate (1.330 Å; Sakamoto et al., 1998), indicating a less marked double-bond character compared with the corresponding value reported for a primary acyl thiocarbamate (1.290 Å; Morales et al., 2000)

Ring C is rotated by a dihedral angle of 83.8 (1)° with respect to ring B. All rings are planar to within 0.01 Å. The thiocarbamic moiety shows a planar conformation, atoms C12, C11, C19 and N2 being coplanar to within 0.004 Å. The molecular fragment N2/C19/(O4)/Ph—NO2 also shows a certain degree of planarity, the conformation being partially stabilized by weak intramolecular hydrogen bonds. Notably, rings 5A and B (Fig. 1) are in contact through a ππ stacking interaction. The mean planes of rings 5A and B form a dihedral angle of 9.6 (1)° and the centroid–centroid distance between the rings is 3.84 (2) Å.

In order to compare similar geometries, the Cambridge Structural Database (CSD, Version?; Allen, 2002) was searched, retrieving all molecules with similar A and B rings separated by an intramolecular centroid–centroid distance within 4.5 Å. Among the nine compounds found, only three have a dihedral angle between the stacked rings of less than 13°: CSD refcodes GUTTIY (Aldridge et al., 2003), HONXOX (Barrett et al., 1998) and QANWAD (Singh et al., 2000) (Fig 2). In the HONXOX structure, the presence of a bulky carboxylate substituent at the phenyl ring B very close to the linker causes a perturbation in the ππ interaction. In fact, among the four structures considered, it is the only case for which the centroid–centroid distance 6A···B is less than that of 5A···B.

Owing to the importance assumed by aromatic π-systems in chemistry and physics, but mainly in biology, the nature of the ππ interaction has been widely studied (see, for example, Hobza et al., 1994; Hunter & Sanders, 1990). To investigate the contribution of electrostatic components to the 5A···B interaction, an ab initio calculation was performed. Mulliken atomic charges were calculated by single-point methods HF/STO-6–311G*, as implemented in HYPERCHEM (Hypercube, 2005). The same computations were applied on both the title compound and the three molecules selected from the CSD, and the relevant parameters obtained for these four molecules are summarized in Table 2. The charge-distribution analysis in the four molecules shows that atoms C1 and C8 of the phthalimide system have the most positive partial charges, suggesting that the ππ stacked conformation is mainly guided by the electrostatic interactions C1···π and C8···π. Moreover, the variation of the centroid–centroid distance, as well as the relative displacement of the two rings, is surely influenced by a series of parameters, including the nature and number of atoms of the linker, the type and position of the substituent present on the phenyl ring B, and probably the occurrence of (weak) hydrogen-bond interactions.

Even considering the crystal packing (Fig. 3), the molecules tend to arrange in such a way as to realise the AB ππ interactions. The molecules involved in the intermolecular case are the centrosymmetric pairs, but the interaction is weaker than for the intramolecular case and, therefore, the molecules also appear more shifted. In fact, the centroid–centroid distance between the two A rings is 4.22 (3) Å and the two rings superimpose only partially, as atoms O1/C1–C5 overlap with atoms C5'–C1'/O1' [prime indicates symmetry operator (−1 − x, 1 − y, −1 − z), shortest distance O1···C5' = 3.603 (4) Å]. Apart from two intermolecular contacts, which are appreciably shorter than the sum of the van der Waals radii [C20···S(−x, y − 1/2, −z + 1/2) = 3.405 (2) Å and C21···S(−x, y − 1/2, −z + 1/2) = 3.205 (3) Å], all other intermolecular distances, as well as all bond lengths and bond angles, are in normal ranges (Reference for standard values?).

Experimental top

The worked up reaction mixture (Source? Reference?) was dissolved in a dichloromethane–ethanol mixture (Ratio?). The solution was kept at room temperature for 2 d and crystals of (I) grew as colourless rods [Prism below?].

Refinement top

The methyl H atoms were treated as an idealized group, with C—H = 0.96 Å, with a global Uiso value fixed at 1.2Ueq(C18). All other H atoms were located in a difference Fourier map and refined freely. [Please check added text] Atom O6 of the nitro group exhibits a large displacement parameter, indicating its tendency to be disordered over two different positions. However, the structural model with the best agreement indexes was that obtained without considering the split positions.

Computing details top

Data collection: MACH3 (Nonius, 2000); cell refinement: MACH3; data reduction: NRCVAX (Gabe et al., 1989) and CADABS (local software); program(s) used to solve structure: NRCVAX; program(s) used to refine structure: SHELXL97 (Sheldrick, 1997), PARST95 (Nardelli, 1995) and HYPERCHEM (Hypercube, 2005); molecular graphics: ORTEP-3 for Windows (Version 1.05; Farrugia, 1997) and Mercury (Version 1.3; Bruno et al., 2002); software used to prepare material for publication: Please provide missing details.

Figures top
[Figure 1] Fig. 1. A drawing of (I), with the labelling scheme for the atoms and rings. Displacement parameters are drawn at the 50% probability level and H atoms are shown as small spheres of arbitrary radii.
[Figure 2] Fig. 2. Schematic representations and three-dimensional structures of the three molecules selected from the CSD.
[Figure 3] Fig. 3. The crystal packing of (I), viewed along the a axis.
O-[2-(1,3-Dioxo-2,3-dihydro-1H-isoindol-2-yl)ethyl] N-(4-methylphenyl)-N-(3-nitrobenzoyl)thiocarbamate top
Crystal data top
C25H19N3O6SF(000) = 1016
Mr = 489.49Dx = 1.399 Mg m3
Monoclinic, P21/cMelting point: 452 K
Hall symbol: -P 2ybcMo Kα radiation, λ = 0.71070 Å
a = 7.918 (2) ÅCell parameters from 16 reflections
b = 10.890 (1) Åθ = 15.1–18.3°
c = 27.087 (7) ŵ = 0.19 mm1
β = 95.72 (2)°T = 293 K
V = 2324.0 (9) Å3Prism, colourless
Z = 40.32 × 0.26 × 0.09 mm
Data collection top
Bruker Nonius MACH3
diffractometer
Rint = 0.000
Radiation source: X-Rayθmax = 27.5°, θmin = 2.6°
Graphite monochromatorh = 010
ω/θ scansk = 014
5311 measured reflectionsl = 3534
5311 independent reflections2 standard reflections every 90 min
2977 reflections with I > 2σ(I) intensity decay: none
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.055Hydrogen site location: difference Fourier map
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0565P)2]
where P = (Fo2 + 2Fc2)/3
5311 reflections(Δ/σ)max = 0.013
381 parametersΔρmax = 0.23 e Å3
0 restraintsΔρmin = 0.21 e Å3
Crystal data top
C25H19N3O6SV = 2324.0 (9) Å3
Mr = 489.49Z = 4
Monoclinic, P21/cMo Kα radiation
a = 7.918 (2) ŵ = 0.19 mm1
b = 10.890 (1) ÅT = 293 K
c = 27.087 (7) Å0.32 × 0.26 × 0.09 mm
β = 95.72 (2)°
Data collection top
Bruker Nonius MACH3
diffractometer
Rint = 0.000
5311 measured reflections2 standard reflections every 90 min
5311 independent reflections intensity decay: none
2977 reflections with I > 2σ(I)
Refinement top
R[F2 > 2σ(F2)] = 0.0550 restraints
wR(F2) = 0.127H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.23 e Å3
5311 reflectionsΔρmin = 0.21 e Å3
381 parameters
Special details top

Refinement. The methylic hydrogen atoms have been treated as idealized group (AFIX 137 instruction), with a global Uiso fixed to 1.2 times that of the bonded carbon atom (C18). One of the oxygen atoms (O6) of the nitro group exhibits a large displacement parameter, indicating its tendency to be disordered over two different positions. However, the structural model with the best agreement indexes was that obtained not considering the split positions.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
C10.3824 (3)0.5149 (3)0.42214 (9)0.0498 (6)
C20.4409 (3)0.4042 (2)0.44791 (8)0.0460 (6)
C30.6017 (4)0.3618 (3)0.45431 (11)0.0621 (8)
C40.6158 (4)0.2572 (3)0.48120 (12)0.0721 (9)
C50.4748 (5)0.1945 (3)0.50153 (13)0.0714 (9)
C60.3104 (4)0.2353 (3)0.49532 (11)0.0600 (7)
C70.2986 (3)0.3417 (2)0.46799 (8)0.0447 (6)
C80.1464 (3)0.4090 (2)0.45546 (9)0.0454 (6)
C90.0989 (4)0.6132 (3)0.41576 (10)0.0545 (7)
C100.0676 (4)0.6157 (2)0.36218 (10)0.0501 (7)
C110.1038 (3)0.5105 (2)0.30868 (9)0.0386 (5)
C120.3261 (3)0.4080 (2)0.26844 (8)0.0360 (5)
C130.4604 (3)0.4877 (2)0.27377 (10)0.0448 (6)
C140.5765 (3)0.4865 (3)0.23867 (11)0.0528 (7)
C150.5622 (3)0.4064 (2)0.19940 (10)0.0523 (7)
C160.4254 (4)0.3281 (3)0.19480 (11)0.0597 (8)
C170.3060 (3)0.3290 (3)0.22914 (10)0.0537 (7)
C180.6913 (4)0.4044 (3)0.16143 (13)0.0857 (11)
H18A0.66770.47020.13820.103*
H18B0.68440.32740.14410.103*
H18C0.80330.41450.17800.103*
C190.1929 (3)0.2991 (2)0.33312 (8)0.0357 (5)
C200.0250 (3)0.25505 (19)0.34709 (8)0.0315 (5)
C210.1298 (3)0.2944 (2)0.32394 (9)0.0377 (5)
C220.2790 (3)0.2390 (2)0.33466 (10)0.0488 (6)
C230.2761 (3)0.1424 (2)0.36730 (11)0.0518 (7)
C240.1218 (3)0.1040 (2)0.38912 (9)0.0468 (6)
C250.0285 (3)0.1588 (2)0.38016 (9)0.0399 (5)
S0.06127 (9)0.60838 (7)0.26357 (3)0.0642 (2)
N10.2066 (3)0.51110 (18)0.42882 (7)0.0462 (5)
N20.2016 (2)0.40733 (16)0.30457 (7)0.0363 (4)
N30.1162 (4)0.0029 (2)0.42241 (11)0.0783 (8)
O10.4658 (3)0.5932 (2)0.39966 (7)0.0735 (6)
O20.0022 (2)0.38436 (18)0.46578 (7)0.0606 (5)
O30.05238 (19)0.51825 (14)0.35399 (6)0.0414 (4)
O40.31815 (19)0.23620 (16)0.34132 (7)0.0556 (5)
O50.2464 (3)0.0502 (2)0.43169 (10)0.1078 (9)
O60.0208 (4)0.0414 (3)0.43877 (14)0.1471 (15)
H30.696 (4)0.413 (3)0.4404 (10)0.067 (9)*
H40.725 (4)0.222 (3)0.4898 (12)0.099 (11)*
H50.480 (4)0.125 (3)0.5206 (12)0.093 (11)*
H60.210 (3)0.192 (3)0.5099 (10)0.066 (9)*
H910.015 (3)0.607 (2)0.4370 (8)0.040 (6)*
H920.157 (3)0.691 (3)0.4230 (10)0.074 (9)*
H1010.181 (4)0.597 (2)0.3395 (10)0.066 (8)*
H1020.016 (3)0.694 (3)0.3541 (10)0.067 (8)*
H130.467 (3)0.544 (2)0.3003 (9)0.050 (7)*
H140.673 (3)0.536 (2)0.2443 (9)0.065 (8)*
H160.415 (4)0.272 (3)0.1694 (11)0.079 (10)*
H170.212 (3)0.272 (3)0.2262 (10)0.069 (8)*
H210.132 (3)0.357 (2)0.3005 (8)0.041 (6)*
H220.375 (3)0.266 (2)0.3181 (9)0.058 (8)*
H230.376 (4)0.108 (3)0.3785 (10)0.072 (9)*
H250.127 (3)0.132 (2)0.3947 (8)0.032 (6)*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.0542 (16)0.0592 (17)0.0366 (13)0.0124 (13)0.0069 (11)0.0021 (13)
C20.0468 (14)0.0556 (16)0.0360 (13)0.0021 (12)0.0066 (11)0.0036 (11)
C30.0442 (16)0.087 (2)0.0562 (17)0.0002 (16)0.0090 (13)0.0083 (17)
C40.059 (2)0.094 (3)0.066 (2)0.0239 (19)0.0184 (17)0.0068 (19)
C50.092 (3)0.062 (2)0.064 (2)0.0190 (19)0.0274 (19)0.0059 (17)
C60.067 (2)0.0591 (18)0.0544 (17)0.0076 (16)0.0108 (15)0.0058 (14)
C70.0455 (14)0.0518 (15)0.0380 (13)0.0002 (12)0.0108 (11)0.0008 (12)
C80.0475 (15)0.0511 (15)0.0394 (13)0.0026 (12)0.0129 (11)0.0054 (11)
C90.070 (2)0.0447 (16)0.0517 (16)0.0050 (15)0.0213 (15)0.0040 (13)
C100.0618 (18)0.0364 (14)0.0558 (16)0.0047 (13)0.0246 (14)0.0033 (12)
C110.0360 (12)0.0387 (13)0.0428 (13)0.0019 (10)0.0123 (10)0.0042 (10)
C120.0299 (11)0.0358 (12)0.0439 (13)0.0002 (10)0.0112 (9)0.0064 (10)
C130.0400 (13)0.0445 (15)0.0500 (15)0.0064 (11)0.0056 (11)0.0001 (12)
C140.0335 (13)0.0582 (17)0.0682 (19)0.0114 (13)0.0123 (12)0.0120 (15)
C150.0503 (15)0.0451 (15)0.0658 (17)0.0101 (12)0.0277 (13)0.0131 (13)
C160.073 (2)0.0471 (16)0.0643 (19)0.0070 (14)0.0314 (15)0.0099 (15)
C170.0535 (16)0.0501 (16)0.0611 (17)0.0189 (13)0.0228 (13)0.0077 (14)
C180.085 (2)0.078 (2)0.105 (3)0.0091 (18)0.062 (2)0.014 (2)
C190.0282 (11)0.0403 (13)0.0386 (12)0.0020 (10)0.0044 (9)0.0035 (10)
C200.0293 (11)0.0307 (11)0.0355 (11)0.0003 (9)0.0084 (9)0.0005 (9)
C210.0334 (12)0.0358 (13)0.0441 (14)0.0018 (10)0.0052 (10)0.0001 (11)
C220.0308 (13)0.0515 (16)0.0643 (17)0.0002 (12)0.0061 (12)0.0045 (14)
C230.0403 (14)0.0494 (16)0.0691 (18)0.0085 (12)0.0223 (13)0.0040 (14)
C240.0524 (15)0.0367 (13)0.0550 (15)0.0008 (11)0.0232 (12)0.0071 (12)
C250.0359 (13)0.0389 (13)0.0461 (14)0.0046 (11)0.0101 (11)0.0041 (11)
S0.0685 (5)0.0675 (5)0.0615 (4)0.0283 (4)0.0304 (4)0.0314 (4)
N10.0490 (13)0.0476 (12)0.0440 (12)0.0016 (10)0.0145 (9)0.0011 (10)
N20.0320 (9)0.0351 (10)0.0438 (11)0.0007 (8)0.0132 (8)0.0057 (9)
N30.080 (2)0.0602 (16)0.100 (2)0.0030 (15)0.0371 (17)0.0340 (15)
O10.0774 (14)0.0780 (15)0.0649 (12)0.0258 (12)0.0063 (11)0.0162 (11)
O20.0401 (10)0.0753 (13)0.0673 (12)0.0093 (9)0.0094 (9)0.0004 (10)
O30.0486 (10)0.0365 (9)0.0410 (9)0.0023 (7)0.0135 (7)0.0028 (7)
O40.0304 (9)0.0598 (11)0.0784 (13)0.0107 (8)0.0144 (8)0.0254 (10)
O50.1043 (19)0.0876 (17)0.140 (2)0.0248 (15)0.0525 (17)0.0473 (17)
O60.101 (2)0.135 (3)0.209 (4)0.019 (2)0.034 (2)0.129 (3)
Geometric parameters (Å, º) top
C1—O11.205 (3)C13—C141.387 (3)
C1—N11.386 (3)C13—H130.95 (2)
C1—C21.490 (4)C14—C151.372 (4)
C2—C71.381 (3)C14—H140.94 (3)
C2—C31.381 (4)C15—C161.374 (4)
C3—C41.363 (5)C15—C181.521 (3)
C3—H30.98 (3)C16—C171.391 (3)
C4—C51.376 (5)C16—H160.92 (3)
C4—H41.00 (3)C17—H170.96 (3)
C5—C61.401 (4)C18—H18A0.9600
C5—H50.92 (3)C18—H18B0.9600
C6—C71.383 (4)C18—H18C0.9600
C6—H60.97 (3)C19—O41.208 (2)
C7—C81.479 (3)C19—N21.415 (3)
C8—O21.212 (3)C19—C201.497 (3)
C8—N11.384 (3)C20—C251.377 (3)
C9—N11.466 (3)C20—C211.388 (3)
C9—C101.497 (3)C21—C221.383 (3)
C9—H911.02 (2)C21—H210.93 (2)
C9—H921.00 (3)C22—C231.373 (4)
C10—O31.456 (3)C22—H220.89 (3)
C10—H1011.06 (3)C23—C241.369 (4)
C10—H1020.98 (3)C23—H230.95 (3)
C11—O31.334 (3)C24—C251.374 (3)
C11—N21.375 (3)C24—N31.471 (3)
C11—S1.632 (2)C25—H250.89 (2)
C12—C171.366 (3)N3—O51.201 (3)
C12—C131.370 (3)N3—O61.205 (3)
C12—N21.456 (3)
O1—C1—N1125.4 (3)C13—C14—H14117.9 (16)
O1—C1—C2129.0 (2)C14—C15—C16117.9 (2)
N1—C1—C2105.6 (2)C14—C15—C18121.6 (3)
C7—C2—C3120.8 (3)C16—C15—C18120.5 (3)
C7—C2—C1107.7 (2)C15—C16—C17121.2 (3)
C3—C2—C1131.5 (3)C15—C16—H16119.5 (19)
C4—C3—C2118.2 (3)C17—C16—H16119.3 (19)
C4—C3—H3125.4 (16)C12—C17—C16119.4 (2)
C2—C3—H3116.3 (17)C12—C17—H17119.8 (16)
C3—C4—C5121.5 (3)C16—C17—H17120.7 (16)
C3—C4—H4124 (2)C15—C18—H18A109.5
C5—C4—H4114 (2)C15—C18—H18B109.5
C4—C5—C6121.4 (3)H18A—C18—H18B109.5
C4—C5—H5124 (2)C15—C18—H18C109.5
C6—C5—H5115 (2)H18A—C18—H18C109.5
C7—C6—C5116.3 (3)H18B—C18—H18C109.5
C7—C6—H6121.7 (16)O4—C19—N2119.27 (19)
C5—C6—H6122.0 (16)O4—C19—C20120.3 (2)
C2—C7—C6121.9 (2)N2—C19—C20119.89 (18)
C2—C7—C8108.5 (2)C25—C20—C21119.2 (2)
C6—C7—C8129.6 (2)C25—C20—C19116.61 (19)
O2—C8—N1125.0 (2)C21—C20—C19123.6 (2)
O2—C8—C7129.2 (2)C22—C21—C20120.3 (2)
N1—C8—C7105.7 (2)C22—C21—H21120.4 (14)
N1—C9—C10113.9 (2)C20—C21—H21119.2 (14)
N1—C9—H91108.4 (13)C23—C22—C21120.7 (3)
C10—C9—H91109.0 (12)C23—C22—H22122.3 (17)
N1—C9—H92107.8 (16)C21—C22—H22116.9 (17)
C10—C9—H92107.5 (16)C24—C23—C22118.0 (2)
H91—C9—H92110 (2)C24—C23—H23118.2 (17)
O3—C10—C9108.0 (2)C22—C23—H23123.4 (17)
O3—C10—H101107.4 (15)C23—C24—C25122.8 (2)
C9—C10—H101110.4 (14)C23—C24—N3118.5 (2)
O3—C10—H102108.1 (15)C25—C24—N3118.6 (2)
C9—C10—H102110.1 (16)C24—C25—C20119.0 (2)
H101—C10—H102113 (2)C24—C25—H25120.9 (14)
O3—C11—N2110.66 (19)C20—C25—H25120.1 (14)
O3—C11—S126.03 (17)C8—N1—C1112.4 (2)
N2—C11—S123.30 (17)C8—N1—C9123.8 (2)
C17—C12—C13120.7 (2)C1—N1—C9123.1 (2)
C17—C12—N2119.1 (2)C11—N2—C19125.25 (17)
C13—C12—N2120.2 (2)C11—N2—C12118.36 (17)
C12—C13—C14118.9 (3)C19—N2—C12116.39 (17)
C12—C13—H13118.5 (15)O5—N3—O6122.3 (3)
C14—C13—H13122.5 (15)O5—N3—C24119.6 (3)
C15—C14—C13121.9 (2)O6—N3—C24118.1 (3)
C15—C14—H14119.9 (16)C11—O3—C10116.77 (18)
O1—C1—C2—C7179.5 (3)C21—C22—C23—C240.7 (4)
N1—C1—C2—C70.2 (3)C22—C23—C24—C250.8 (4)
O1—C1—C2—C31.6 (5)C22—C23—C24—N3177.3 (2)
N1—C1—C2—C3178.6 (3)C23—C24—C25—C201.3 (4)
C7—C2—C3—C40.4 (4)N3—C24—C25—C20176.8 (2)
C1—C2—C3—C4178.3 (3)C21—C20—C25—C240.3 (3)
C2—C3—C4—C50.1 (5)C19—C20—C25—C24171.3 (2)
C3—C4—C5—C60.3 (5)O2—C8—N1—C1179.4 (2)
C4—C5—C6—C70.3 (4)C7—C8—N1—C11.2 (3)
C3—C2—C7—C60.3 (4)O2—C8—N1—C99.5 (4)
C1—C2—C7—C6178.7 (2)C7—C8—N1—C9170.0 (2)
C3—C2—C7—C8179.5 (2)O1—C1—N1—C8178.8 (2)
C1—C2—C7—C80.5 (3)C2—C1—N1—C80.9 (3)
C5—C6—C7—C20.1 (4)O1—C1—N1—C99.9 (4)
C5—C6—C7—C8179.0 (3)C2—C1—N1—C9170.4 (2)
C2—C7—C8—O2179.5 (2)C10—C9—N1—C8106.3 (3)
C6—C7—C8—O21.3 (4)C10—C9—N1—C183.5 (3)
C2—C7—C8—N11.0 (3)O3—C11—N2—C1925.5 (3)
C6—C7—C8—N1178.1 (2)S—C11—N2—C19155.09 (18)
N1—C9—C10—O374.2 (3)O3—C11—N2—C12153.93 (18)
C17—C12—C13—C140.3 (4)S—C11—N2—C1225.5 (3)
N2—C12—C13—C14179.7 (2)O4—C19—N2—C11151.3 (2)
C12—C13—C14—C151.2 (4)C20—C19—N2—C1136.7 (3)
C13—C14—C15—C161.7 (4)O4—C19—N2—C1228.1 (3)
C13—C14—C15—C18179.1 (3)C20—C19—N2—C12143.9 (2)
C14—C15—C16—C170.7 (4)C17—C12—N2—C11114.9 (3)
C18—C15—C16—C17179.9 (3)C13—C12—N2—C1164.5 (3)
C13—C12—C17—C161.3 (4)C17—C12—N2—C1965.6 (3)
N2—C12—C17—C16179.3 (2)C13—C12—N2—C19115.0 (2)
C15—C16—C17—C120.8 (4)C23—C24—N3—O53.7 (4)
O4—C19—C20—C2516.3 (3)C25—C24—N3—O5178.2 (3)
N2—C19—C20—C25171.8 (2)C23—C24—N3—O6175.0 (3)
O4—C19—C20—C21154.9 (2)C25—C24—N3—O63.2 (5)
N2—C19—C20—C2117.0 (3)N2—C11—O3—C10173.5 (2)
C25—C20—C21—C221.2 (3)S—C11—O3—C107.1 (3)
C19—C20—C21—C22172.2 (2)C9—C10—O3—C11176.2 (2)
C20—C21—C22—C231.7 (4)

Experimental details

Crystal data
Chemical formulaC25H19N3O6S
Mr489.49
Crystal system, space groupMonoclinic, P21/c
Temperature (K)293
a, b, c (Å)7.918 (2), 10.890 (1), 27.087 (7)
β (°) 95.72 (2)
V3)2324.0 (9)
Z4
Radiation typeMo Kα
µ (mm1)0.19
Crystal size (mm)0.32 × 0.26 × 0.09
Data collection
DiffractometerBruker Nonius MACH3
diffractometer
Absorption correction
No. of measured, independent and
observed [I > 2σ(I)] reflections
5311, 5311, 2977
Rint0.000
(sin θ/λ)max1)0.649
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.055, 0.127, 1.00
No. of reflections5311
No. of parameters381
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.23, 0.21

Computer programs: MACH3 (Nonius, 2000), MACH3, NRCVAX (Gabe et al., 1989) and CADABS (local software), NRCVAX, SHELXL97 (Sheldrick, 1997), PARST95 (Nardelli, 1995) and HYPERCHEM (Hypercube, 2005), ORTEP-3 for Windows (Version 1.05; Farrugia, 1997) and Mercury (Version 1.3; Bruno et al., 2002), Please provide missing details.

Selected geometric parameters (Å, º) top
C9—N11.466 (3)C12—N21.456 (3)
C11—O31.334 (3)C19—O41.208 (2)
C11—N21.375 (3)C19—N21.415 (3)
C11—S1.632 (2)C19—C201.497 (3)
N1—C9—C10113.9 (2)C11—N2—C19125.25 (17)
O3—C10—C9108.0 (2)C11—O3—C10116.77 (18)
O3—C11—N2110.66 (19)
C20—C19—N2—C12143.9 (2)
Calculated charges (a.u.) and geometric parameters (Å, °) for compound (I) and the three compounds selected from the CSD top
CompoundCharge onCharge on5 A···B6 A···BA–B dihedralAtoms in
C8 (a.u.)C1 (a.u.)distancedistanceanglelinker
(I)0.6570.6273.844.469.046
GUTTIY0.6270.6733.343.8511.673
HONXOX0.6580.6644.773.965.957
QANWAD0.5970.6123.543.795.073
References: (I): this work. GUTTIY: Aldridge et al. (2003). HONXOX: Barrett et al. (1998). QANWAD: Singh et al. (2000).
 

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