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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages o1505-o1506
doi:10.1107/S1600536812015371

2-[6-(4-Bromo­phen­yl)imidazo[2,1-b][1,3]thia­zol-3-yl]-N-[8-(4-hy­dr­oxy­phen­yl)-2-methyl-3-oxo-1-thia-4-aza­spiro­[4.5]decan-4-yl]acetamide ethanol disolvate

Mehmet Akkurt,a* Elif Gürsoy,b Nuray Ulusoy Güzeldemirci,b Sevim Türktekin-Çelikesira and Muhammad Nawaz Tahirc

aDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, bDepartment of Pharmaceutical Chemistry, Faculty of Pharmacy, University of Istanbul, 34116 Beyazıt, Istanbul, Turkey, and cDepartment of Physics, University of Sargodha, Sargodha, Pakistan
*Correspondence e-mail: akkurt@erciyes.edu.tr

(Received 3 April 2012; accepted 8 April 2012; online 21 April 2012)

In the title compound, C28H27BrN4O3S2·2C2H6O, the cyclo­hexane ring adopts a chair conformation. The imidazo[2,1-b][1,3]thia­zole ring system is essentially planar with a dihedral angle of 1.1 (2)° between the thia­zole and imidazole rings. The mean plane of this ring system makes dihedral angles of 8.11 (16) and 79.43 (17)°, respectively, with the bromo- and hy­droxy-substituted benzene rings. In the 5-methyl-1,3-thia­zolidin-4-one group, the S atom, the methyl group and the ring C atoms bonded to them are disordered over two sets of sites with refined occupancies of 0.610 (19) and 0.390 (19). The crystal structure features N—H⋯O, O—H⋯O, O—H⋯N and C—H⋯O hydrogen bonds and C—H⋯π inter­actions. Furthermore, two weak π–π stacking inter­actions [centroid–centroid distances = 3.967 (3) and 3.892 (2) Å] are also observed.

Related literature

For the biological activity of imidazo[2,1-b][1,3]thia­zole derivatives, see: Barradas et al. (2008[Barradas, J. S., Errea, M. I., D'Accorso, N., Sepúlveda, C. S., Talarico, L. B. & Damonte, E. B. (2008). Carbohydr. Res. 343, 2468-2474.]); Juspin et al. (2010[Juspin, T., Laget, M., Terme, T., Azas, N. & Vanelle, P. (2010). Eur. J. Med. Chem. 45, 840-845.]). For our previous papers on the synthesis of imidazo[2,1-b]thia­zoles, see: Gürsoy & Ulusoy Güzeldemirci (2007[Gürsoy, E. & Ulusoy Güzeldemirci, N. (2007). Eur. J. Med. Chem. 42, 320-326.]); Ulusoy Güzeldemirci & Küçükbasmacı (2010[Ulusoy Güzeldemirci, N. & Küçükbasmacı, Ö. (2010). Eur. J. Med. Chem. 45, 63-68.]), and for their crystal structures, see: Akkurt et al. (2007[Akkurt, M., Yalçın, Ş. P., Gürsoy, E., Güzeldemirci, N. U. & Büyükgüngör, O. (2007). Acta Cryst. E63, o3103.], 2008[Akkurt, M., Yalçın, Ş. P., Güzeldemirci, N. U. & Büyükgüngör, O. (2008). Acta Cryst. E64, o810-o811.], 2011[Akkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184-o185.]). For standard bond lengths, see: Allen et al. (1987[Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1-19.]). For ring-puckering analysis, see: Cremer & Pople (1975[Cremer, D. & Pople, J. A. (1975). J. Am. Chem. Soc. 97, 1354-1358.]).

[Scheme 1]

Experimental

Crystal data

  • C28H27BrN4O3S2·2C2H6O

  • Mr = 703.71

  • Monoclinic, P 21 /c

  • a = 14.9549 (15) Å

  • b = 13.2642 (11) Å

  • c = 17.9393 (17) Å

  • β = 109.015 (3)°

  • V = 3364.4 (5) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.39 mm−1

  • T = 296 K

  • 0.35 × 0.25 × 0.22 mm
Data collection

  • Bruker Kappa APEXII CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2005[Bruker (2005). SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.665, Tmax = 0.736

  • 27860 measured reflections

  • 6971 independent reflections

  • 2926 reflections with I > 2σ(I)

  • Rint = 0.066
Refinement

  • R[F2 > 2σ(F2)] = 0.056

  • wR(F2) = 0.150

  • S = 1.00

  • 6971 reflections

  • 428 parameters

  • 12 restraints

  • H-atom parameters constrained

  • Δρmax = 0.44 e Å−3

  • Δρmin = −0.36 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg5 and Cg7 are the centroids of the C1–C6 and C23–C28 benzene rings, respectively.
D—H⋯A D—H H⋯A D⋯A D—H⋯A
N3—H3⋯O5i 0.86 1.92 2.771 (5) 170
O3—H3A⋯O2ii 0.82 1.91 2.713 (5) 164
O4—H4A⋯N1iii 0.82 2.07 2.857 (5) 161
O5—H5A⋯O4iv 0.82 1.84 2.655 (5) 174
C31—H31B⋯O1 0.96 2.49 3.312 (8) 144
C15A—H15A⋯Cg7iv 0.98 2.81 3.772 (14) 167
C24—H24⋯Cg5 0.93 2.69 3.600 (4) 168
Symmetry codes: (i) [x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]; (ii) x, y-1, z; (iii) x+1, y, z; (iv) [-x+1, y+{\script{1\over 2}}, -z+{\script{3\over 2}}].

Data collection: APEX2 (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). APEX2 and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 (Farrugia, 1997[Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]); software used to prepare material for publication: WinGX (Farrugia, 1999[Farrugia, L. J. (1999). J. Appl. Cryst. 32, 837-838.]) and PLATON.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536812015371/is5113sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812015371/is5113Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812015371/is5113Isup3.cml

checkCIF report


Comment top

Imidazo[2,1-b][1,3]thiazole derivatives have demonstrated a broad range of biological activities, including antiviral (Barradas et al., 2008) and antibacterial (Juspin et al., 2010). In connection with our previous papers on the synthesis of imidazo[2,1-b]thiazoles (Gürsoy & Ulusoy Güzeldemirci, 2007; Ulusoy Güzeldemirci & Küçükbasmacı, 2010) and their crystal structures (Akkurt et al., 2007, 2008, 2011), we report here the crystal structure of the title spiro derivative, 2-[6-(4-bromophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]-N-(8-(4-hydroxyphenyl)-2-methyl-1-thia-4-azaspiro[4.5]decan-3-one)acetamide ethanol disolvate (Fig. 1).

In the title compound (I), the S1/N2/C9–C11 thiazole and N1/N2/C7–C9 imidazole rings of the imidazo[2,1-b][1,3]thiazole group (S1/N1/N2/C7–C11) make a dihedral angle of 1.1 (2)° with each other. The imidazo[2,1-b][1,3]thiazole group makes dihedral angles of 8.11 (16) and 79.43 (17)°, with the benzene rings which have the bromo atom and the hydroxyl group, respectively. The dihedral angle between these two benzene rings is 86.7 (2)°. The bond lengths and bond angles in (I) are comparable with the values reported in related structures (Allen et al., 1987; Akkurt et al., 2007; 2008; 2011).

In the disordered 1,3-thiazolidine group, the S2A/N4/C14/C15A/C17 five-membered ring, with the major components of the disorder, has a twisted conformation on the S2A—C15A bond [puckering parameters (Cremer & Pople, 1975): Q(2) = 0.360 (10) Å, ϕ(2) = 195.4 (11) °], and the S2B/N4/C14/C15B/C17 ring, with the minor components of the disorder, adopts an envelope conformation with the C15B atom at the flap [Q(2) = 0.315 (14) Å, ϕ(2) = 66.3 (16) °].

In the crystal structure, molecules are connected by intermolecular N—H···O, O—H···O, O—H···N and C—H···O hydrogen bonds (Table 1, Fig. 2) and C—H···π interactions, forming a three dimensional network. Two weak π–π stacking interactions [Cg1···Cg5(-x, 1 - y, 1 - z) = 3.967 (3) Å and Cg3···Cg5(-x, 1 - y, 1 - z) = 3.892 (2) Å; where Cg1, Cg3 and Cg5 are the centroids of the S1/N2/C9—C11 thiazole, N1/N2/C7—C9 imidazole and C1—C6 benzene rings, respectively] are also observed.

Related literature top

For the biological activity of imidazo[2,1-b][1,3]thiazole derivatives, see: Barradas et al. (2008); Juspin et al. (2010). For our previous papers on the synthesis of imidazo[2,1-b]thiazoles, see: Gürsoy & Ulusoy Güzeldemirci (2007); Ulusoy Güzeldemirci & Küçükbasmacı (2010), and for their crystal structures, see: Akkurt et al. (2007, 2008, 2011). For standard bond lengths, see: Allen et al. (1987). For ring-puckering analysis, see: Cremer & Pople (1975).

Experimental top

A mixture of 6-(4-bromophenyl)-N-(4-(4-hydroxyphenyl)cyclohexylidene)imidazo[2,1-b]thiazole-3-acetohydrazide (0.005 mol) and 2-mercaptopropionic acid (0.01 mol) was refluxed in dry benzene (30 ml) using a Dean-Stark trap for 48 h. Excess benzene was evaporated in vacuo. The residue was triturated with saturated NaHCO3 until CO2 evolution ceased and then allowed to stand overnight. The solid thus obtained was filtered, washed with H2O and recrystallized from C2H5OH to yield colourless prisms of compound. Yield (%): 54. M.p. (K): 558–559. IR [ν, cm-1, KBr]: 3226, 3138 (O—H, N—H), 1724,1670 (C=O). Analysis calculated for C28H27N4O3S2. 2C2H5OH: C 54.62, H 5.59, N 7.96%. Found: C 54.16, H 5.75, N 7.35%.

Refinement top

All H atoms were placed geometrically with C—H = 0.93, 0.96, 0.97 and 0.98 Å for phenyl, methyl, methylene and methine H atoms, respectively, N—H = 0.86 Å and O—H = 0.82 Å and refined by using the riding model [Uiso(H) = xUeq(C,O), x = 1.5 for methyl and hydroxyl H and 1.2 for all other H atoms]. In the 5-methyl-1,3-thiazolidin-4-one group of (I), the S2 atom, the methyl group (C16) and the C15 atom bound to them are disordered over two sets of sites with refined occupancies of 0.59 (2) and 0.41 (2). Three poorly fitted reflections (1 0 0), (1 6 1) and (-1 0 2) were omitted from the refinement. Distance restraints were applied for the ethanol molecules [C29—C30 and C31—C32 = 1.56 (2) Å, C29—O4 and C32—O5 = 1.35 (2) Å, C30—O4 and C31—O5 = 2.32 (2) Å] and the disordered ring [C15A C16A and C15B C16B 1.56 (2), C17—S2A, C17—S2B, C15A—S2A and C15B—S2B = 1.82 (2) Å].

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 (Farrugia, 1997) and PLATON (Spek, 2009); software used to prepare material for publication: WinGX (Farrugia, 1999) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound. Displacement ellipsoids for non-H atoms are drawn at the 30% probability level. For clarity, only the major components of disorder are shown.
[Figure 2] Fig. 2. A packing diagram and hydrogen bonding of the title compound, viewed down the b axis. H atoms not involved in hydrogen bonds have been omitted for clarity. Only the major components of disorder are shown.
2-[6-(4-Bromophenyl)imidazo[2,1-b][1,3]thiazol-3-yl]-N- [8-(4-hydroxyphenyl)-2-methyl-3-oxo-1-thia-4-azaspiro[4.5]decan-4-yl]acetamide ethanol disolvate top
Crystal data top
C28H27BrN4O3S2·2C2H6OF(000) = 1464
Mr = 703.71Dx = 1.389 Mg m−3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybcCell parameters from 327 reflections
a = 14.9549 (15) Åθ = 3.5–20°
b = 13.2642 (11) ŵ = 1.39 mm−1
c = 17.9393 (17) ÅT = 296 K
β = 109.015 (3)°Prism, white
V = 3364.4 (5) Å30.35 × 0.25 × 0.22 mm
Z = 4
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6971 independent reflections
Radiation source: fine-focus sealed tube2926 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.066
ω scansθmax = 26.5°, θmin = 2.0°
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		h = −18→17
Tmin = 0.665, Tmax = 0.736k = −16→14
27860 measured reflectionsl = −20→22
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)] = 0.056Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.150H-atom parameters constrained
S = 1.00 w = 1/[σ2(Fo2) + (0.059P)2 + 0.1004P]
where P = (Fo2 + 2Fc2)/3
6971 reflections(Δ/σ)max < 0.001
428 parametersΔρmax = 0.44 e Å−3
12 restraintsΔρmin = −0.36 e Å−3
Crystal data top
C28H27BrN4O3S2·2C2H6OV = 3364.4 (5) Å3
Mr = 703.71Z = 4
Monoclinic, P21/cMo Kα radiation
a = 14.9549 (15) ŵ = 1.39 mm−1
b = 13.2642 (11) ÅT = 296 K
c = 17.9393 (17) Å0.35 × 0.25 × 0.22 mm
β = 109.015 (3)°
Data collection top
Bruker Kappa APEXII CCD
diffractometer		6971 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2005)		2926 reflections with I > 2σ(I)
Tmin = 0.665, Tmax = 0.736Rint = 0.066
27860 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.05612 restraints
wR(F2) = 0.150H-atom parameters constrained
S = 1.00Δρmax = 0.44 e Å−3
6971 reflectionsΔρmin = −0.36 e Å−3
428 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
xyzUiso*/UeqOcc. (<1)
Br10.09539 (5)0.08007 (4)0.42261 (3)0.0994 (3)
S1−0.10100 (11)0.59938 (11)0.71949 (9)0.0991 (7)
S2A0.4804 (7)0.5211 (7)0.8893 (6)0.096 (3)0.610 (19)
O10.2141 (2)0.7185 (2)0.8423 (2)0.0855 (16)
O20.4304 (2)0.79805 (19)0.8429 (2)0.0910 (13)
O30.3050 (3)−0.09257 (17)0.72779 (19)0.0849 (15)
N1−0.0424 (3)0.4494 (3)0.6353 (2)0.0689 (17)
N20.0378 (3)0.5929 (2)0.66586 (19)0.0559 (14)
N30.2814 (3)0.6861 (2)0.74894 (18)0.0506 (13)
N40.3622 (2)0.6463 (2)0.80216 (19)0.0509 (11)
C10.1150 (3)0.3626 (3)0.5243 (2)0.0609 (17)
C20.1293 (3)0.2796 (3)0.4821 (2)0.0668 (19)
C30.0752 (4)0.1946 (3)0.4789 (3)0.0656 (19)
C40.0080 (4)0.1910 (3)0.5150 (3)0.0671 (19)
C5−0.0056 (3)0.2744 (3)0.5564 (2)0.0610 (17)
C60.0481 (3)0.3622 (3)0.5622 (2)0.0506 (16)
C70.0329 (3)0.4491 (3)0.6061 (2)0.0537 (17)
C80.0823 (3)0.5370 (3)0.6244 (2)0.0525 (16)
C9−0.0363 (3)0.5371 (4)0.6704 (3)0.0674 (19)
C10−0.0244 (4)0.7006 (4)0.7329 (3)0.079 (2)
C110.0444 (4)0.6885 (3)0.7021 (3)0.0635 (17)
C120.1249 (3)0.7561 (3)0.7072 (3)0.0647 (16)
C130.2113 (3)0.7209 (3)0.7744 (3)0.058 (2)
C140.4321 (3)0.7062 (3)0.8446 (3)0.0741 (19)
C15A0.5213 (9)0.6475 (5)0.8785 (8)0.059 (4)0.610 (19)
C16A0.5789 (17)0.6842 (17)0.9598 (11)0.090 (6)0.610 (19)
C170.3723 (3)0.5360 (2)0.8059 (2)0.0484 (15)
C180.2902 (3)0.4860 (3)0.8227 (2)0.0588 (18)
C190.2988 (3)0.3717 (2)0.8228 (2)0.0610 (18)
C200.3065 (3)0.3332 (2)0.7463 (2)0.0506 (15)
C210.3890 (3)0.3819 (3)0.7294 (2)0.0629 (18)
C220.3829 (3)0.4969 (2)0.7299 (2)0.0605 (16)
C230.3094 (3)0.2193 (2)0.7425 (2)0.0478 (15)
C240.2489 (3)0.1687 (3)0.6804 (2)0.0575 (16)
C250.2484 (3)0.0647 (3)0.6751 (3)0.0649 (18)
C260.3112 (3)0.0097 (3)0.7335 (2)0.0562 (16)
C270.3751 (3)0.0577 (3)0.7953 (3)0.0600 (16)
C280.3738 (3)0.1618 (3)0.7991 (2)0.0619 (16)
C16B0.594 (2)0.689 (3)0.940 (2)0.097 (10)0.390 (19)
S2B0.4827 (10)0.5145 (10)0.8849 (9)0.091 (5)0.390 (19)
C15B0.4954 (10)0.6441 (7)0.9219 (13)0.045 (5)0.390 (19)
O40.7754 (2)0.4226 (3)0.51981 (19)0.0853 (14)
C290.6290 (5)0.5002 (7)0.4923 (4)0.198 (5)
C300.7073 (4)0.4545 (5)0.5521 (3)0.110 (3)
O50.2790 (4)0.7871 (3)1.0951 (2)0.125 (2)
C310.2786 (7)0.6425 (6)1.0282 (4)0.206 (5)
C320.3415 (7)0.7079 (5)1.0729 (5)0.172 (5)
H20.174300.281400.456600.0800*
H3A0.35030−0.117900.761700.1270*
H4−0.028300.133200.511800.0810*
H30.275500.688900.699700.0610*
H10.151600.420000.527100.0730*
H10−0.031000.758800.759500.0950*
H12A0.109200.824800.716800.0780*
H12B0.138500.754800.657900.0780*
H15A0.558900.647800.842900.0710*0.610 (19)
H16A0.635600.644800.979200.1350*0.610 (19)
H5−0.051600.271900.581000.0730*
H80.135400.555300.611400.0630*
H18A0.231600.506100.783000.0710*
H18B0.288200.508300.873600.0710*
H19A0.354300.351100.865800.0730*
H19B0.243800.341900.831500.0730*
H200.249200.354900.704500.0610*
H21A0.390400.359600.678300.0750*
H21B0.447400.360500.768800.0750*
H22A0.439600.525200.723200.0720*
H22B0.329200.518800.685800.0720*
H240.206400.205400.640100.0690*
H250.205800.032300.632100.0780*
H270.419000.020800.834600.0720*
H280.418000.194200.841200.0740*
H16B0.542500.677400.994800.1350*0.610 (19)
H16C0.595200.753800.956900.1350*0.610 (19)
H15B0.471400.652100.966300.0540*0.390 (19)
H16D0.636800.657500.985900.1460*0.390 (19)
H16E0.592100.760300.949000.1460*0.390 (19)
H16F0.616400.678000.895800.1460*0.390 (19)
H4A0.826300.416300.555000.1280*
H29A0.582400.521600.515200.2960*
H29B0.601400.452000.451300.2960*
H29C0.651000.557400.470500.2960*
H30A0.735000.502900.593800.1320*
H30B0.685000.397300.574900.1320*
H5A0.258300.826801.058400.1880*
H31A0.311300.589201.011700.3090*
H31B0.237700.676700.982700.3090*
H31C0.241700.614801.058100.3090*
H32A0.378800.738201.043600.2060*
H32B0.383600.675201.119600.2060*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.1375 (6)0.0619 (3)0.1037 (5)0.0105 (3)0.0460 (4)−0.0123 (3)
S10.0933 (12)0.1140 (11)0.1082 (12)−0.0111 (9)0.0580 (10)−0.0321 (9)
S2A0.098 (6)0.044 (3)0.092 (5)0.014 (3)−0.042 (4)0.008 (3)
O10.085 (3)0.112 (3)0.056 (2)0.018 (2)0.018 (2)−0.0131 (19)
O20.077 (2)0.0332 (16)0.136 (3)−0.0046 (15)−0.002 (2)−0.0040 (16)
O30.114 (3)0.0291 (15)0.098 (3)0.0003 (16)0.016 (2)−0.0035 (13)
N10.067 (3)0.072 (3)0.071 (3)−0.012 (2)0.027 (2)−0.010 (2)
N20.051 (3)0.060 (2)0.052 (2)0.0003 (19)0.0102 (19)−0.0076 (17)
N30.062 (3)0.0352 (16)0.046 (2)0.0022 (17)0.006 (2)−0.0024 (15)
N40.054 (2)0.0318 (16)0.057 (2)0.0033 (17)0.0047 (19)0.0034 (15)
C10.061 (3)0.051 (3)0.062 (3)−0.004 (2)0.008 (3)0.004 (2)
C20.074 (4)0.066 (3)0.061 (3)0.010 (3)0.023 (3)0.003 (2)
C30.076 (4)0.049 (3)0.064 (3)0.009 (3)0.012 (3)−0.005 (2)
C40.067 (4)0.050 (3)0.080 (3)−0.003 (2)0.018 (3)−0.002 (2)
C50.055 (3)0.059 (3)0.067 (3)−0.001 (2)0.017 (2)−0.002 (2)
C60.043 (3)0.049 (2)0.054 (3)0.002 (2)0.008 (2)0.0069 (19)
C70.051 (3)0.058 (3)0.049 (3)−0.002 (2)0.012 (2)0.000 (2)
C80.048 (3)0.051 (2)0.059 (3)0.003 (2)0.018 (2)0.000 (2)
C90.061 (4)0.075 (3)0.069 (3)−0.005 (3)0.025 (3)−0.012 (3)
C100.071 (4)0.092 (4)0.072 (4)0.010 (3)0.020 (3)−0.022 (3)
C110.060 (3)0.058 (3)0.061 (3)0.012 (3)0.004 (3)−0.005 (2)
C120.062 (3)0.044 (2)0.076 (3)0.011 (2)0.006 (3)−0.002 (2)
C130.064 (4)0.041 (2)0.063 (4)0.003 (2)0.011 (3)−0.008 (2)
C140.056 (3)0.040 (3)0.107 (4)0.001 (2)0.000 (3)−0.003 (2)
C15A0.057 (7)0.059 (5)0.062 (7)−0.003 (4)0.019 (6)0.005 (4)
C16A0.114 (14)0.070 (7)0.060 (11)−0.034 (8)−0.006 (8)0.012 (8)
C170.054 (3)0.0316 (19)0.056 (3)0.0023 (19)0.013 (2)0.0024 (17)
C180.080 (4)0.042 (2)0.065 (3)−0.005 (2)0.038 (3)−0.0074 (19)
C190.086 (4)0.034 (2)0.074 (3)−0.004 (2)0.041 (3)−0.0009 (19)
C200.062 (3)0.0323 (19)0.054 (3)0.006 (2)0.014 (2)0.0019 (18)
C210.083 (4)0.038 (2)0.077 (3)0.003 (2)0.039 (3)0.000 (2)
C220.079 (3)0.037 (2)0.073 (3)0.001 (2)0.035 (3)0.0052 (19)
C230.053 (3)0.0334 (19)0.055 (3)0.002 (2)0.015 (2)0.0010 (19)
C240.069 (3)0.042 (2)0.056 (3)0.003 (2)0.013 (2)0.005 (2)
C250.081 (4)0.041 (2)0.061 (3)−0.004 (2)0.007 (3)−0.006 (2)
C260.073 (3)0.028 (2)0.069 (3)0.000 (2)0.025 (3)−0.001 (2)
C270.064 (3)0.040 (2)0.069 (3)0.005 (2)0.012 (3)0.008 (2)
C280.066 (3)0.038 (2)0.070 (3)−0.003 (2)0.006 (2)0.001 (2)
C16B0.086 (17)0.122 (17)0.067 (18)0.001 (14)0.002 (14)0.065 (14)
S2B0.096 (10)0.042 (5)0.117 (9)−0.006 (5)0.010 (7)−0.001 (5)
C15B0.037 (9)0.039 (6)0.061 (11)−0.002 (5)0.019 (7)−0.001 (6)
O40.068 (2)0.095 (2)0.092 (3)−0.001 (2)0.025 (2)−0.015 (2)
C290.152 (8)0.293 (11)0.149 (7)0.113 (8)0.051 (6)0.045 (7)
C300.098 (5)0.133 (5)0.103 (5)0.005 (4)0.038 (4)−0.014 (4)
O50.232 (5)0.079 (2)0.087 (3)0.030 (3)0.082 (3)0.0068 (19)
C310.296 (13)0.153 (7)0.120 (7)−0.032 (8)0.002 (7)0.027 (6)
C320.253 (11)0.101 (6)0.143 (7)0.015 (6)0.038 (7)0.028 (5)
Geometric parameters (Å, º) top
Br1—C31.902 (5)C23—C241.361 (5)
S1—C91.717 (5)C23—C281.380 (5)
S1—C101.730 (6)C24—C251.383 (6)
S2A—C15A1.817 (13)C25—C261.368 (6)
S2A—C171.821 (11)C26—C271.363 (6)
S2B—C171.814 (16)C27—C281.383 (6)
S2B—C15B1.830 (18)C1—H10.9300
O1—C131.206 (6)C2—H20.9300
O2—C141.219 (5)C4—H40.9300
O3—C261.361 (5)C5—H50.9300
O3—H3A0.8200C8—H80.9300
O4—C301.392 (7)C10—H100.9300
O4—H4A0.8200C12—H12B0.9700
O5—C321.542 (10)C12—H12A0.9700
O5—H5A0.8200C15A—H15A0.9800
N1—C91.312 (7)C15B—H15B0.9800
N1—C71.388 (6)C16A—H16C0.9600
N2—C111.414 (5)C16A—H16B0.9600
N2—C81.367 (6)C16A—H16A0.9600
N2—C91.357 (6)C16B—H16F0.9700
N3—N41.378 (5)C16B—H16E0.9600
N3—C131.354 (6)C16B—H16D0.9600
N4—C141.336 (6)C18—H18A0.9700
N4—C171.470 (4)C18—H18B0.9700
N3—H30.8600C19—H19B0.9700
C1—C61.381 (6)C19—H19A0.9700
C1—C21.392 (6)C20—H200.9800
C2—C31.378 (6)C21—H21B0.9700
C3—C41.362 (9)C21—H21A0.9700
C4—C51.384 (6)C22—H22A0.9700
C5—C61.399 (6)C22—H22B0.9700
C6—C71.455 (6)C24—H240.9300
C7—C81.362 (6)C25—H250.9300
C10—C111.327 (9)C27—H270.9300
C11—C121.480 (7)C28—H280.9300
C12—C131.525 (7)C29—C301.439 (10)
C14—C15B1.63 (2)C29—H29B0.9600
C14—C15A1.492 (13)C29—H29A0.9600
C15A—C16A1.51 (2)C29—H29C0.9600
C15B—C16B1.52 (4)C30—H30A0.9700
C17—C181.510 (6)C30—H30B0.9700
C17—C221.515 (5)C31—C321.338 (12)
C18—C191.522 (5)C31—H31A0.9600
C19—C201.504 (5)C31—H31B0.9600
C20—C231.514 (4)C31—H31C0.9600
C20—C211.508 (6)C32—H32A0.9700
C21—C221.528 (5)C32—H32B0.9700
C9—S1—C1089.2 (3)C4—C5—H5119.00
C15A—S2A—C1793.0 (6)C6—C5—H5119.00
C15B—S2B—C1795.5 (9)C7—C8—H8127.00
C26—O3—H3A109.00N2—C8—H8127.00
C30—O4—H4A109.00C11—C10—H10123.00
C32—O5—H5A109.00S1—C10—H10123.00
C7—N1—C9104.2 (4)C11—C12—H12A110.00
C9—N2—C11113.4 (4)C11—C12—H12B110.00
C8—N2—C11139.8 (4)C13—C12—H12B110.00
C8—N2—C9106.8 (3)H12A—C12—H12B108.00
N4—N3—C13119.8 (3)C13—C12—H12A110.00
N3—N4—C17117.8 (3)C16A—C15A—H15A111.00
C14—N4—C17121.1 (3)S2A—C15A—H15A111.00
N3—N4—C14120.9 (3)C14—C15A—H15A111.00
C13—N3—H3120.00C16B—C15B—H15B112.00
N4—N3—H3120.00C14—C15B—H15B112.00
C2—C1—C6122.0 (4)S2B—C15B—H15B112.00
C1—C2—C3118.5 (4)C15A—C16A—H16C109.00
C2—C3—C4121.5 (4)H16A—C16A—H16B110.00
Br1—C3—C4119.6 (3)H16A—C16A—H16C109.00
Br1—C3—C2118.9 (4)H16B—C16A—H16C109.00
C3—C4—C5119.2 (4)C15A—C16A—H16B110.00
C4—C5—C6121.6 (4)C15A—C16A—H16A109.00
C5—C6—C7120.8 (4)C15B—C16B—H16E110.00
C1—C6—C7122.0 (4)H16D—C16B—H16E109.00
C1—C6—C5117.2 (4)H16D—C16B—H16F109.00
N1—C7—C8110.5 (4)C15B—C16B—H16F110.00
C6—C7—C8129.8 (4)H16E—C16B—H16F109.00
N1—C7—C6119.7 (4)C15B—C16B—H16D110.00
N2—C8—C7105.9 (4)C19—C18—H18A109.00
N1—C9—N2112.7 (4)C19—C18—H18B109.00
S1—C9—N2112.1 (4)H18A—C18—H18B108.00
S1—C9—N1135.2 (4)C17—C18—H18B109.00
S1—C10—C11114.6 (4)C17—C18—H18A109.00
N2—C11—C10110.7 (5)C18—C19—H19B109.00
N2—C11—C12120.4 (5)C18—C19—H19A109.00
C10—C11—C12128.8 (4)C20—C19—H19B109.00
C11—C12—C13109.0 (4)C20—C19—H19A109.00
O1—C13—C12123.3 (4)H19A—C19—H19B108.00
N3—C13—C12112.8 (4)C21—C20—H20107.00
O1—C13—N3123.8 (4)C23—C20—H20107.00
O2—C14—C15B122.0 (6)C19—C20—H20107.00
N4—C14—C15B108.4 (5)C20—C21—H21B109.00
O2—C14—C15A122.7 (5)C22—C21—H21A109.00
N4—C14—C15A110.6 (5)C20—C21—H21A109.00
O2—C14—N4125.0 (4)H21A—C21—H21B108.00
C14—C15A—C16A112.2 (11)C22—C21—H21B109.00
S2A—C15A—C16A107.5 (11)C17—C22—H22B109.00
S2A—C15A—C14103.8 (8)H22A—C22—H22B108.00
S2B—C15B—C16B115.0 (17)C21—C22—H22A109.00
S2B—C15B—C14101.8 (12)C21—C22—H22B109.00
C14—C15B—C16B103.8 (16)C17—C22—H22A109.00
N4—C17—C18111.6 (3)C23—C24—H24119.00
S2A—C17—N4101.3 (4)C25—C24—H24119.00
S2A—C17—C22112.2 (4)C24—C25—H25120.00
S2B—C17—N4104.2 (5)C26—C25—H25120.00
S2A—C17—C18110.5 (4)C28—C27—H27120.00
S2B—C17—C18111.6 (5)C26—C27—H27120.00
S2B—C17—C22108.3 (6)C23—C28—H28119.00
N4—C17—C22109.8 (3)C27—C28—H28119.00
C18—C17—C22111.1 (3)O4—C30—C29110.2 (5)
C17—C18—C19111.4 (3)C30—C29—H29A109.00
C18—C19—C20111.7 (3)C30—C29—H29B109.00
C21—C20—C23112.4 (4)H29A—C29—H29B110.00
C19—C20—C23113.1 (3)H29A—C29—H29C109.00
C19—C20—C21110.4 (3)C30—C29—H29C109.00
C20—C21—C22111.8 (3)H29B—C29—H29C109.00
C17—C22—C21111.8 (3)O4—C30—H30B110.00
C24—C23—C28116.6 (3)C29—C30—H30A110.00
C20—C23—C24120.5 (3)O4—C30—H30A110.00
C20—C23—C28122.8 (3)H30A—C30—H30B108.00
C23—C24—C25122.4 (4)C29—C30—H30B110.00
C24—C25—C26119.5 (4)O5—C32—C31103.3 (8)
C25—C26—C27119.9 (4)C32—C31—H31A109.00
O3—C26—C27122.6 (4)C32—C31—H31B109.00
O3—C26—C25117.5 (4)C32—C31—H31C109.00
C26—C27—C28119.3 (4)H31A—C31—H31B109.00
C23—C28—C27122.2 (4)H31A—C31—H31C110.00
C2—C1—H1119.00H31B—C31—H31C109.00
C6—C1—H1119.00O5—C32—H32A111.00
C3—C2—H2121.00O5—C32—H32B111.00
C1—C2—H2121.00C31—C32—H32A111.00
C5—C4—H4120.00C31—C32—H32B111.00
C3—C4—H4120.00H32A—C32—H32B109.00
C9—S1—C10—C110.4 (4)C4—C5—C6—C10.5 (6)
C10—S1—C9—N2−0.2 (4)C4—C5—C6—C7−179.9 (4)
C10—S1—C9—N1−178.8 (6)C5—C6—C7—N1−7.1 (5)
C15A—S2A—C17—C2293.9 (6)C5—C6—C7—C8173.6 (4)
C15A—S2A—C17—C18−141.6 (5)C1—C6—C7—C8−6.8 (6)
C17—S2A—C15A—C1430.0 (8)C1—C6—C7—N1172.5 (4)
C17—S2A—C15A—C16A149.0 (12)C6—C7—C8—N2179.6 (4)
C15A—S2A—C17—N4−23.2 (6)N1—C7—C8—N20.3 (4)
C7—N1—C9—S1178.5 (4)S1—C10—C11—N2−0.6 (6)
C9—N1—C7—C6−179.5 (4)S1—C10—C11—C12−175.5 (4)
C7—N1—C9—N2−0.1 (5)C10—C11—C12—C1395.9 (6)
C9—N1—C7—C8−0.1 (5)N2—C11—C12—C13−78.6 (5)
C8—N2—C11—C12−6.3 (8)C11—C12—C13—N3113.7 (4)
C11—N2—C9—S1−0.1 (5)C11—C12—C13—O1−61.9 (5)
C11—N2—C9—N1178.9 (4)O2—C14—C15A—C16A50.0 (14)
C11—N2—C8—C7−178.3 (5)N4—C14—C15A—S2A−28.4 (9)
C8—N2—C9—N10.3 (5)N4—C14—C15A—C16A−144.1 (11)
C9—N2—C11—C100.4 (6)O2—C14—C15A—S2A165.7 (6)
C8—N2—C9—S1−178.7 (3)S2A—C17—C18—C19−70.7 (4)
C9—N2—C11—C12175.8 (4)N4—C17—C18—C19177.4 (3)
C9—N2—C8—C7−0.4 (4)C22—C17—C18—C1954.5 (4)
C8—N2—C11—C10178.3 (5)S2A—C17—C22—C2170.8 (5)
N4—N3—C13—C12−176.4 (3)N4—C17—C22—C21−177.3 (3)
C13—N3—N4—C14−82.1 (5)C18—C17—C22—C21−53.4 (4)
C13—N3—N4—C17102.9 (4)C17—C18—C19—C20−56.6 (4)
N4—N3—C13—O1−0.9 (6)C18—C19—C20—C2156.5 (4)
C17—N4—C14—O2177.6 (4)C18—C19—C20—C23−176.6 (4)
N3—N4—C14—O22.7 (7)C19—C20—C21—C22−55.2 (4)
C14—N4—C17—C22−108.1 (4)C23—C20—C21—C22177.5 (3)
N3—N4—C14—C15A−162.8 (6)C19—C20—C23—C24127.9 (4)
C17—N4—C14—C15A12.1 (8)C19—C20—C23—C28−54.1 (6)
N3—N4—C17—S2A−174.3 (4)C21—C20—C23—C24−106.2 (5)
C14—N4—C17—S2A10.7 (6)C21—C20—C23—C2871.8 (5)
N3—N4—C17—C18−56.7 (4)C20—C21—C22—C1754.2 (4)
C14—N4—C17—C18128.3 (4)C20—C23—C24—C25−179.2 (4)
N3—N4—C17—C2267.0 (5)C28—C23—C24—C252.7 (7)
C2—C1—C6—C5−0.2 (6)C20—C23—C28—C27179.4 (4)
C6—C1—C2—C3−0.5 (6)C24—C23—C28—C27−2.5 (7)
C2—C1—C6—C7−179.8 (4)C23—C24—C25—C26−0.7 (7)
C1—C2—C3—Br1−179.1 (3)C24—C25—C26—O3176.8 (4)
C1—C2—C3—C40.9 (7)C24—C25—C26—C27−1.6 (7)
C2—C3—C4—C5−0.6 (8)O3—C26—C27—C28−176.6 (4)
Br1—C3—C4—C5179.4 (4)C25—C26—C27—C281.7 (7)
C3—C4—C5—C6−0.1 (7)C26—C27—C28—C230.4 (7)
Hydrogen-bond geometry (Å, º) top
Cg5 and Cg7 are the centroids of the C1–C6 and C23–C28 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N3—H3···O5i0.861.922.771 (5)170
O3—H3A···O2ii0.821.912.713 (5)164
O4—H4A···N1iii0.822.072.857 (5)161
O5—H5A···O4iv0.821.842.655 (5)174
C5—H5···N10.932.532.864 (6)101
C31—H31B···O10.962.493.312 (8)144
C15A—H15A···Cg7iv0.982.813.772 (14)167
C24—H24···Cg50.932.693.600 (4)168
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+3/2.

Experimental details

Crystal data
Chemical formulaC28H27BrN4O3S2·2C2H6O
Mr703.71
Crystal system, space groupMonoclinic, P21/c
Temperature (K)296
a, b, c (Å)14.9549 (15), 13.2642 (11), 17.9393 (17)
β (°) 109.015 (3)
V (Å3)3364.4 (5)
Z4
Radiation typeMo Kα
µ (mm−1)1.39
Crystal size (mm)0.35 × 0.25 × 0.22
Data collection
DiffractometerBruker Kappa APEXII CCD
diffractometer
Absorption correctionMulti-scan
(SADABS; Bruker, 2005)
Tmin, Tmax0.665, 0.736
No. of measured, independent and
observed [I > 2σ(I)] reflections		27860, 6971, 2926
Rint0.066
(sin θ/λ)max (Å−1)0.628
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.056, 0.150, 1.00
No. of reflections6971
No. of parameters428
No. of restraints12
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.44, −0.36

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

Hydrogen-bond geometry (Å, º) top
Cg5 and Cg7 are the centroids of the C1–C6 and C23–C28 benzene rings, respectively.
D—H···AD—HH···AD···AD—H···A
N3—H3···O5i0.861.922.771 (5)170
O3—H3A···O2ii0.821.912.713 (5)164
O4—H4A···N1iii0.822.072.857 (5)161
O5—H5A···O4iv0.821.842.655 (5)174
C31—H31B···O10.962.493.312 (8)144
C15A—H15A···Cg7iv0.982.813.772 (14)167
C24—H24···Cg50.932.693.600 (4)168
Symmetry codes: (i) x, −y+3/2, z−1/2; (ii) x, y−1, z; (iii) x+1, y, z; (iv) −x+1, y+1/2, −z+3/2.
 

Acknowledgements

The authors acknowledge the provision of funds for the purchase of a diffractometer and encouragement by Dr Muhammad Akram Chaudhary, Vice Chancellor, University of Sargodha, Pakistan.

References

First citationAkkurt, M., Güzeldemirci, N. U., Karaman, B. & Büyükgüngör, O. (2011). Acta Cryst. E67, o184–o185.  Web of Science CrossRef CAS IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 68| Part 5| May 2012| Pages o1505-o1506
doi:10.1107/S1600536812015371
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