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

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ISSN: 2056-9890

N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­­oxy­phen­yl)-2,4,6-tri­methyl­benzene­sulfonamide

aDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, bPG Department of Studies in Chemistry, JSS College of Arts, Commerce and Science, Ooty Road, Mysore 570 025, India, and cX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India
*Correspondence e-mail: mas@physics.uni-mysore.ac.in

(Received 17 August 2012; accepted 18 August 2012; online 25 August 2012)

In the title compound, C25H29BrN4O3S2, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 63.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 64.9 (1)°. The mol­ecular conformation is stabilized by a weak intra­molecular ππ stacking inter­action between the pyrimidine and the 2,4,6-trimethyl­benzene rings [centroid–centroid distance = 3.766 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, mol­ecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds and these dimers are further linked by C—H⋯O hydrogen bonds into chains propagating along [010].

Related literature

For the crystal structures of related sulfonamides, see: Rodrigues et al. (2011[Rodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2891.]); Akkurt et al. (2011[Akkurt, M., Mariam, I., Naseer, I., Khan, I. U. & Sharif, S. (2011). Acta Cryst. E67, o186.]); Kant et al. (2012[Kant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590-o2591.]).

[Scheme 1]

Experimental

Crystal data
  • C25H29BrN4O3S2

  • Mr = 577.55

  • Monoclinic, P 21 /n

  • a = 9.3334 (5) Å

  • b = 10.3635 (4) Å

  • c = 27.8258 (11) Å

  • β = 92.924 (4)°

  • V = 2688.0 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 1.72 mm−1

  • T = 293 K

  • 0.3 × 0.2 × 0.2 mm

Data collection
  • Oxford Diffraction Xcalibur Sapphire3 diffractometer

  • Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]) Tmin = 0.649, Tmax = 1.000

  • 21429 measured reflections

  • 5266 independent reflections

  • 3580 reflections with I > 2σ(I)

  • Rint = 0.043

Refinement
  • R[F2 > 2σ(F2)] = 0.054

  • wR(F2) = 0.123

  • S = 1.06

  • 5266 reflections

  • 320 parameters

  • H-atom parameters constrained

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.43 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N1—H1⋯O2i 0.86 2.03 2.880 (5) 172
C8—H8A⋯O2ii 0.96 2.48 3.242 (5) 136
C11—H11⋯O1iii 0.93 2.50 3.387 (6) 159
Symmetry codes: (i) -x, -y+2, -z; (ii) -x+1, -y+2, -z; (iii) -x, -y+1, -z.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; 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.]); software used to prepare material for publication: PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

Bond lengths and angles in the title compound (Fig. 1) are comparable with those in similar crystal structures (Rodrigues et al., 2011; Akkurt et al., 2011; Kant et al., 2012). The piperidine ring is exhibiting a chair conformation. The two benzene rings (C1—C6/C9—C14) are tilted relative to each other by 63.9 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 64.9 (1)°. The molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 2,4,6 -trimethyl benzene rings [centroid–centroid distance = 3.766 (2) Å, interplanar spacing = 3.507 Å, and centroid shift = 1.37 Å]. In the crystal, molecules are linked into dimers by pairs of N1—H1···O2 hydrogen bonds and these dimers are further linked by C—H···O hydrogen bonds into chains along [010](Fig.2).

Related literature top

For the crystal structures of related sulfonamides, see: Rodrigues et al. (2011); Akkurt et al. (2011); Kant et al. (2012).

Experimental top

The reaction of N-[2-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-2,4,6-trimethyl -benzenesulfonamide(5.29 g, 0.01 mol) with piperidine (0.86 g, 0.01) were carried out in the presence of triethylamine and the reaction mixture was allowed to stir at room temperature for 6–7 h in dry dichloromethane. The progress of the reaction was monitored by TLC. Upon completion, the solvent was removed under reduced pressure and residue was extracted with ethyl acetate. The compound was purified by successive recrystallization from methanol (yield 82%, m.p. 460–462 K).

Refinement top

All H atoms were positioned geometrically and were treated as riding on their parent C/N atoms, with C—H distances of 0.93–0.97 Å and N—H distance of 0.86 with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis PRO (Oxford Diffraction, 2010); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 (Farrugia, 1997); software used to prepare material for publication: PLATON (Spek, 2009).

Figures top
Fig. 1. View of the molecule with displacement ellipsoids drawn at the 40% probability level.

Fig. 2. A molecular packing view of the title compound down the a axis, showing intermolecular interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.
N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfanyl}-4- methoxyphenyl)-2,4,6-trimethylbenzenesulfonamide top
Crystal data top
C25H29BrN4O3S2F(000) = 1192
Mr = 577.55Dx = 1.427 Mg m3
Monoclinic, P21/nMo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ynCell parameters from 6963 reflections
a = 9.3334 (5) Åθ = 3.5–29.0°
b = 10.3635 (4) ŵ = 1.72 mm1
c = 27.8258 (11) ÅT = 293 K
β = 92.924 (4)°Block, white
V = 2688.0 (2) Å30.3 × 0.2 × 0.2 mm
Z = 4
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
5266 independent reflections
Radiation source: fine-focus sealed tube3580 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.043
Detector resolution: 16.1049 pixels mm-1θmax = 26.0°, θmin = 3.5°
ω scanh = 1111
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
k = 1212
Tmin = 0.649, Tmax = 1.000l = 3434
21429 measured reflections
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)] = 0.054Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.123H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0365P)2 + 2.6423P]
where P = (Fo2 + 2Fc2)/3
5266 reflections(Δ/σ)max = 0.001
320 parametersΔρmax = 0.35 e Å3
0 restraintsΔρmin = 0.43 e Å3
Crystal data top
C25H29BrN4O3S2V = 2688.0 (2) Å3
Mr = 577.55Z = 4
Monoclinic, P21/nMo Kα radiation
a = 9.3334 (5) ŵ = 1.72 mm1
b = 10.3635 (4) ÅT = 293 K
c = 27.8258 (11) Å0.3 × 0.2 × 0.2 mm
β = 92.924 (4)°
Data collection top
Oxford Diffraction Xcalibur Sapphire3
diffractometer
5266 independent reflections
Absorption correction: multi-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
3580 reflections with I > 2σ(I)
Tmin = 0.649, Tmax = 1.000Rint = 0.043
21429 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0540 restraints
wR(F2) = 0.123H-atom parameters constrained
S = 1.06Δρmax = 0.35 e Å3
5266 reflectionsΔρmin = 0.43 e Å3
320 parameters
Special details top

Experimental. CrysAlis PRO, Oxford Diffraction Ltd., Version 1.171.34.40 (release 27–08-2010 CrysAlis171. NET) (compiled Aug 27 2010,11:50:40) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
xyzUiso*/Ueq
Br10.24625 (5)1.11199 (4)0.216359 (17)0.07602 (19)
S10.19179 (12)0.85193 (11)0.00058 (3)0.0626 (3)
S20.10025 (10)0.89654 (9)0.14471 (3)0.0513 (3)
O10.2090 (4)0.7302 (3)0.02194 (10)0.0849 (10)
O20.1541 (3)0.9599 (3)0.02939 (9)0.0725 (9)
O30.0197 (3)0.4244 (3)0.15889 (9)0.0700 (8)
N10.0612 (4)0.8411 (3)0.03700 (10)0.0628 (9)
H10.00050.90350.03740.075*
N40.5272 (3)0.8077 (3)0.21918 (12)0.0604 (9)
N50.3329 (3)0.7523 (3)0.16362 (10)0.0453 (7)
N70.5265 (4)0.6181 (3)0.17624 (14)0.0733 (10)
C10.3494 (4)0.8878 (4)0.03643 (12)0.0523 (9)
C20.3591 (4)1.0096 (4)0.05852 (13)0.0518 (9)
C30.4791 (4)1.0346 (4)0.08927 (14)0.0612 (11)
H30.48561.11450.10450.073*
C40.5867 (5)0.9480 (5)0.09806 (14)0.0646 (12)
C50.5758 (5)0.8317 (5)0.07489 (15)0.0699 (12)
H50.64980.77250.08010.084*
C60.4601 (5)0.7970 (4)0.04384 (15)0.0652 (11)
C70.2507 (5)1.1154 (4)0.05177 (17)0.0712 (12)
H7A0.25151.14740.01940.107*
H7B0.27401.18420.07390.107*
H7C0.15711.08250.05760.107*
C80.7134 (5)0.9787 (6)0.13240 (16)0.0922 (17)
H8A0.78731.01960.11510.138*
H8B0.74990.90020.14670.138*
H8C0.68321.03560.15720.138*
C90.0417 (4)0.7345 (4)0.06810 (12)0.0555 (10)
C100.0028 (6)0.6177 (5)0.04949 (15)0.0934 (18)
H100.02000.61000.01640.112*
C110.0228 (6)0.5119 (5)0.07801 (15)0.0879 (17)
H110.05060.43350.06420.106*
C120.0016 (4)0.5222 (4)0.12717 (13)0.0549 (10)
C130.0332 (4)0.6404 (4)0.14644 (12)0.0500 (9)
H130.04040.64970.17970.060*
C140.0579 (4)0.7461 (4)0.11776 (12)0.0449 (8)
C150.0514 (6)0.2991 (4)0.14117 (17)0.0791 (14)
H15A0.13760.30180.12090.119*
H15B0.06450.24180.16770.119*
H15C0.02650.26890.12290.119*
C160.2696 (4)0.8624 (3)0.17246 (11)0.0406 (8)
C170.3325 (4)0.9525 (3)0.20396 (12)0.0466 (9)
C180.4616 (4)0.7291 (4)0.18658 (13)0.0504 (9)
C210.4617 (4)0.9181 (4)0.22662 (13)0.0580 (10)
H210.50510.97600.24840.070*
C220.6581 (5)0.5732 (5)0.2017 (2)0.0938 (16)
H22A0.69400.63960.22370.113*
H22B0.73060.55660.17870.113*
C230.6303 (6)0.4531 (6)0.2290 (2)0.110 (2)
H23A0.56890.47320.25510.131*
H23B0.72040.42060.24310.131*
C240.5602 (7)0.3496 (6)0.1980 (3)0.124 (2)
H24A0.53360.27760.21790.148*
H24B0.62750.31830.17520.148*
C250.4283 (6)0.4025 (5)0.1711 (2)0.1031 (19)
H25A0.38980.33770.14880.124*
H25B0.35560.42140.19380.124*
C260.4612 (6)0.5222 (5)0.14396 (18)0.0857 (15)
H26A0.52610.50190.11890.103*
H26B0.37350.55670.12880.103*
C270.4663 (7)0.6661 (5)0.0203 (2)0.113 (2)
H27A0.55490.62440.03000.169*
H27B0.46060.67620.01410.169*
H27C0.38730.61440.02990.169*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0919 (4)0.0579 (3)0.0777 (3)0.0032 (2)0.0005 (3)0.0240 (2)
S10.0804 (8)0.0720 (7)0.0346 (5)0.0331 (6)0.0047 (5)0.0008 (5)
S20.0549 (6)0.0503 (5)0.0476 (5)0.0009 (5)0.0081 (4)0.0051 (4)
O10.117 (3)0.085 (2)0.0528 (17)0.039 (2)0.0007 (17)0.0228 (16)
O20.077 (2)0.095 (2)0.0442 (15)0.0272 (17)0.0060 (14)0.0220 (15)
O30.103 (2)0.0584 (17)0.0485 (15)0.0251 (16)0.0001 (15)0.0052 (14)
N10.069 (2)0.077 (2)0.0421 (17)0.0288 (19)0.0059 (15)0.0138 (17)
N40.055 (2)0.067 (2)0.058 (2)0.0087 (18)0.0134 (16)0.0050 (18)
N50.0479 (18)0.0480 (18)0.0394 (16)0.0064 (14)0.0029 (13)0.0011 (14)
N70.067 (2)0.062 (2)0.088 (3)0.0127 (19)0.018 (2)0.008 (2)
C10.063 (2)0.055 (2)0.0388 (19)0.016 (2)0.0010 (17)0.0008 (18)
C20.051 (2)0.059 (2)0.046 (2)0.013 (2)0.0029 (17)0.0005 (19)
C30.061 (3)0.073 (3)0.049 (2)0.024 (2)0.003 (2)0.009 (2)
C40.052 (3)0.099 (4)0.043 (2)0.016 (3)0.0038 (19)0.008 (2)
C50.060 (3)0.089 (3)0.061 (3)0.007 (3)0.008 (2)0.016 (3)
C60.080 (3)0.062 (3)0.054 (2)0.008 (2)0.010 (2)0.003 (2)
C70.075 (3)0.061 (3)0.077 (3)0.009 (2)0.004 (2)0.013 (2)
C80.058 (3)0.154 (5)0.063 (3)0.027 (3)0.008 (2)0.016 (3)
C90.067 (3)0.063 (2)0.0353 (19)0.032 (2)0.0038 (17)0.0024 (18)
C100.156 (5)0.090 (4)0.034 (2)0.069 (4)0.004 (3)0.008 (2)
C110.146 (5)0.075 (3)0.043 (2)0.061 (3)0.013 (3)0.012 (2)
C120.067 (3)0.057 (2)0.041 (2)0.023 (2)0.0038 (18)0.0000 (19)
C130.054 (2)0.064 (3)0.0313 (18)0.0146 (19)0.0020 (16)0.0010 (18)
C140.043 (2)0.055 (2)0.0353 (18)0.0125 (17)0.0051 (15)0.0019 (17)
C150.102 (4)0.052 (3)0.083 (3)0.015 (3)0.005 (3)0.000 (2)
C160.048 (2)0.045 (2)0.0282 (16)0.0126 (17)0.0002 (14)0.0024 (15)
C170.055 (2)0.048 (2)0.0370 (19)0.0115 (18)0.0042 (17)0.0042 (16)
C180.051 (2)0.054 (2)0.046 (2)0.0048 (19)0.0029 (18)0.0033 (18)
C210.065 (3)0.064 (3)0.045 (2)0.019 (2)0.0068 (19)0.009 (2)
C220.058 (3)0.093 (4)0.129 (5)0.014 (3)0.007 (3)0.003 (4)
C230.064 (3)0.132 (5)0.131 (5)0.015 (3)0.015 (3)0.053 (4)
C240.085 (4)0.083 (4)0.200 (7)0.002 (3)0.019 (4)0.042 (5)
C250.088 (4)0.073 (3)0.145 (5)0.006 (3)0.022 (4)0.006 (4)
C260.099 (4)0.072 (3)0.085 (3)0.023 (3)0.010 (3)0.016 (3)
C270.159 (6)0.076 (4)0.102 (4)0.015 (4)0.002 (4)0.023 (3)
Geometric parameters (Å, º) top
Br1—C171.878 (4)C8—H8C0.9600
S1—O11.422 (3)C9—C101.373 (5)
S1—O21.429 (3)C9—C141.388 (5)
S1—N11.628 (3)C10—C111.372 (6)
S1—C11.774 (4)C10—H100.9300
S2—C161.760 (4)C11—C121.376 (5)
S2—C141.766 (4)C11—H110.9300
O3—C121.360 (4)C12—C131.369 (5)
O3—C151.415 (5)C13—C141.382 (5)
N1—C91.420 (5)C13—H130.9300
N1—H10.8600C15—H15A0.9600
N4—C211.319 (5)C15—H15B0.9600
N4—C181.343 (5)C15—H15C0.9600
N5—C161.313 (4)C16—C171.390 (4)
N5—C181.353 (4)C17—C211.379 (5)
N7—C181.339 (5)C21—H210.9300
N7—C261.452 (6)C22—C231.488 (7)
N7—C221.461 (6)C22—H22A0.9700
C1—C21.405 (5)C22—H22B0.9700
C1—C61.405 (6)C23—C241.505 (8)
C2—C31.398 (5)C23—H23A0.9700
C2—C71.497 (6)C23—H23B0.9700
C3—C41.360 (6)C24—C251.511 (7)
C3—H30.9300C24—H24A0.9700
C4—C51.368 (6)C24—H24B0.9700
C4—C81.516 (6)C25—C261.493 (7)
C5—C61.395 (6)C25—H25A0.9700
C5—H50.9300C25—H25B0.9700
C6—C271.509 (6)C26—H26A0.9700
C7—H7A0.9600C26—H26B0.9700
C7—H7B0.9600C27—H27A0.9600
C7—H7C0.9600C27—H27B0.9600
C8—H8A0.9600C27—H27C0.9600
C8—H8B0.9600
O1—S1—O2117.88 (18)C12—C13—H13119.1
O1—S1—N1108.56 (19)C14—C13—H13119.1
O2—S1—N1104.34 (19)C13—C14—C9119.6 (3)
O1—S1—C1108.9 (2)C13—C14—S2119.7 (3)
O2—S1—C1109.66 (17)C9—C14—S2120.7 (3)
N1—S1—C1106.87 (16)O3—C15—H15A109.5
C16—S2—C14100.67 (17)O3—C15—H15B109.5
C12—O3—C15119.2 (3)H15A—C15—H15B109.5
C9—N1—S1123.8 (3)O3—C15—H15C109.5
C9—N1—H1118.1H15A—C15—H15C109.5
S1—N1—H1118.1H15B—C15—H15C109.5
C21—N4—C18115.7 (3)N5—C16—C17121.5 (3)
C16—N5—C18117.5 (3)N5—C16—S2119.7 (2)
C18—N7—C26122.7 (4)C17—C16—S2118.8 (3)
C18—N7—C22123.2 (4)C21—C17—C16116.4 (3)
C26—N7—C22113.4 (4)C21—C17—Br1121.1 (3)
C2—C1—C6120.5 (4)C16—C17—Br1122.4 (3)
C2—C1—S1117.9 (3)N7—C18—N4118.1 (4)
C6—C1—S1121.6 (3)N7—C18—N5116.9 (3)
C3—C2—C1117.8 (4)N4—C18—N5125.1 (4)
C3—C2—C7117.1 (4)N4—C21—C17123.7 (3)
C1—C2—C7125.1 (3)N4—C21—H21118.2
C4—C3—C2123.3 (4)C17—C21—H21118.2
C4—C3—H3118.4N7—C22—C23110.5 (4)
C2—C3—H3118.4N7—C22—H22A109.6
C3—C4—C5117.4 (4)C23—C22—H22A109.6
C3—C4—C8121.4 (5)N7—C22—H22B109.6
C5—C4—C8121.2 (5)C23—C22—H22B109.6
C4—C5—C6123.7 (4)H22A—C22—H22B108.1
C4—C5—H5118.1C22—C23—C24112.6 (5)
C6—C5—H5118.1C22—C23—H23A109.1
C5—C6—C1117.3 (4)C24—C23—H23A109.1
C5—C6—C27117.1 (5)C22—C23—H23B109.1
C1—C6—C27125.6 (4)C24—C23—H23B109.1
C2—C7—H7A109.5H23A—C23—H23B107.8
C2—C7—H7B109.5C23—C24—C25110.1 (5)
H7A—C7—H7B109.5C23—C24—H24A109.6
C2—C7—H7C109.5C25—C24—H24A109.6
H7A—C7—H7C109.5C23—C24—H24B109.6
H7B—C7—H7C109.5C25—C24—H24B109.6
C4—C8—H8A109.5H24A—C24—H24B108.1
C4—C8—H8B109.5C26—C25—C24111.6 (5)
H8A—C8—H8B109.5C26—C25—H25A109.3
C4—C8—H8C109.5C24—C25—H25A109.3
H8A—C8—H8C109.5C26—C25—H25B109.3
H8B—C8—H8C109.5C24—C25—H25B109.3
C10—C9—C14117.9 (3)H25A—C25—H25B108.0
C10—C9—N1120.1 (3)N7—C26—C25110.3 (4)
C14—C9—N1121.9 (3)N7—C26—H26A109.6
C11—C10—C9122.3 (4)C25—C26—H26A109.6
C11—C10—H10118.9N7—C26—H26B109.6
C9—C10—H10118.9C25—C26—H26B109.6
C10—C11—C12119.7 (4)H26A—C26—H26B108.1
C10—C11—H11120.1C6—C27—H27A109.5
C12—C11—H11120.1C6—C27—H27B109.5
O3—C12—C13116.6 (3)H27A—C27—H27B109.5
O3—C12—C11124.8 (4)C6—C27—H27C109.5
C13—C12—C11118.6 (4)H27A—C27—H27C109.5
C12—C13—C14121.7 (3)H27B—C27—H27C109.5
O1—S1—N1—C942.9 (3)C12—C13—C14—C92.6 (6)
O2—S1—N1—C9169.4 (3)C12—C13—C14—S2179.2 (3)
C1—S1—N1—C974.5 (3)C10—C9—C14—C131.8 (6)
O1—S1—C1—C2174.6 (3)N1—C9—C14—C13177.9 (4)
O2—S1—C1—C244.2 (3)C10—C9—C14—S2174.7 (4)
N1—S1—C1—C268.3 (3)N1—C9—C14—S21.4 (5)
O1—S1—C1—C67.1 (4)C16—S2—C14—C1367.1 (3)
O2—S1—C1—C6137.5 (3)C16—S2—C14—C9116.3 (3)
N1—S1—C1—C6110.0 (3)C18—N5—C16—C170.4 (5)
C6—C1—C2—C32.4 (5)C18—N5—C16—S2178.6 (2)
S1—C1—C2—C3175.9 (3)C14—S2—C16—N58.3 (3)
C6—C1—C2—C7177.6 (4)C14—S2—C16—C17170.8 (3)
S1—C1—C2—C74.1 (5)N5—C16—C17—C212.3 (5)
C1—C2—C3—C41.0 (6)S2—C16—C17—C21176.7 (3)
C7—C2—C3—C4179.0 (4)N5—C16—C17—Br1178.8 (2)
C2—C3—C4—C50.8 (6)S2—C16—C17—Br12.2 (4)
C2—C3—C4—C8178.9 (4)C26—N7—C18—N4175.9 (4)
C3—C4—C5—C61.3 (6)C22—N7—C18—N45.7 (6)
C8—C4—C5—C6178.4 (4)C26—N7—C18—N53.1 (6)
C4—C5—C6—C10.1 (6)C22—N7—C18—N5173.3 (4)
C4—C5—C6—C27178.7 (4)C21—N4—C18—N7177.3 (4)
C2—C1—C6—C52.0 (6)C21—N4—C18—N53.7 (6)
S1—C1—C6—C5176.3 (3)C16—N5—C18—N7178.3 (3)
C2—C1—C6—C27176.6 (4)C16—N5—C18—N42.8 (5)
S1—C1—C6—C275.1 (6)C18—N4—C21—C171.5 (6)
S1—N1—C9—C1071.3 (5)C16—C17—C21—N41.3 (6)
S1—N1—C9—C14112.7 (4)Br1—C17—C21—N4179.8 (3)
C14—C9—C10—C114.0 (8)C18—N7—C22—C23114.5 (5)
N1—C9—C10—C11179.8 (5)C26—N7—C22—C2356.6 (6)
C9—C10—C11—C121.7 (9)N7—C22—C23—C2453.4 (7)
C15—O3—C12—C13178.0 (4)C22—C23—C24—C2552.3 (7)
C15—O3—C12—C115.4 (7)C23—C24—C25—C2653.1 (7)
C10—C11—C12—O3179.3 (5)C18—N7—C26—C25113.2 (5)
C10—C11—C12—C132.8 (8)C22—N7—C26—C2557.9 (6)
O3—C12—C13—C14178.3 (3)C24—C25—C26—N755.7 (7)
C11—C12—C13—C145.0 (6)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.880 (5)172
C8—H8A···O2ii0.962.483.242 (5)136
C11—H11···O1iii0.932.503.387 (6)159
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z; (iii) x, y+1, z.

Experimental details

Crystal data
Chemical formulaC25H29BrN4O3S2
Mr577.55
Crystal system, space groupMonoclinic, P21/n
Temperature (K)293
a, b, c (Å)9.3334 (5), 10.3635 (4), 27.8258 (11)
β (°) 92.924 (4)
V3)2688.0 (2)
Z4
Radiation typeMo Kα
µ (mm1)1.72
Crystal size (mm)0.3 × 0.2 × 0.2
Data collection
DiffractometerOxford Diffraction Xcalibur Sapphire3
diffractometer
Absorption correctionMulti-scan
(CrysAlis PRO; Oxford Diffraction, 2010)
Tmin, Tmax0.649, 1.000
No. of measured, independent and
observed [I > 2σ(I)] reflections
21429, 5266, 3580
Rint0.043
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.054, 0.123, 1.06
No. of reflections5266
No. of parameters320
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å3)0.35, 0.43

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.862.032.880 (5)172
C8—H8A···O2ii0.962.483.242 (5)136
C11—H11···O1iii0.932.503.387 (6)159
Symmetry codes: (i) x, y+2, z; (ii) x+1, y+2, z; (iii) x, y+1, z.
 

Acknowledgements

MK acknowledges the help of Bahubali College of Engin­eering for his research work. RK acknowledges the Department of Science & Technology for the single-crystal X-ray diffractometer sanctioned as a National Facility under project No. SR/S2/CMP-47/2003.

References

First citationAkkurt, M., Mariam, I., Naseer, I., Khan, I. U. & Sharif, S. (2011). Acta Cryst. E67, o186.  Web of Science CrossRef IUCr Journals
First citationFarrugia, L. J. (1997). J. Appl. Cryst. 30, 565.  CrossRef IUCr Journals
First citationKant, R., Gupta, V. K., Kapoor, K., Kumar, M., Mallesha, L. & Sridhar, M. A. (2012). Acta Cryst. E68, o2590–o2591.  CSD CrossRef IUCr Journals
First citationOxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.
First citationRodrigues, V. Z., Foro, S. & Gowda, B. T. (2011). Acta Cryst. E67, o2891.  Web of Science CSD CrossRef IUCr Journals
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals
First citationSpek, A. L. (2009). Acta Cryst. D65, 148–155.  Web of Science CrossRef CAS IUCr Journals

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