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

Kumar, M.; Mallesha, L.; Sridhar, M.A.; Kapoor, K.; Gupta, V.K.; Kant, R.

doi:10.1107/S1600536812036185

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2767

doi:10.1107/S1600536812036185

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

Mohan Kumar,^a L. Mallesha,^b M. A. Sridhar,^a ^* Kamini Kapoor,^c Vivek K. Gupta ^c and Rajni Kant ^c

^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 π–π 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 ); Akkurt et al. (2011 ); Kant et al. (2012 ).

Experimental

Crystal data

C₂₅H₂₉BrN₄O₃S₂
M_r = 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 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.649, T_max = 1.000
21429 measured reflections
5266 independent reflections
3580 reflections with I > 2σ(I)
R_int = 0.043

Refinement

R[F² > 2σ(F²)] = 0.054
wR(F²) = 0.123
S = 1.06
5266 reflections
320 parameters
H-atom parameters constrained
Δρ_max = 0.35 e Å⁻³
Δρ_min = −0.43 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	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 ); 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 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536812036185/hb6940sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036185/hb6940Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036185/hb6940Isup3.cml

checkCIF report

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).

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

C₂₅H₂₉BrN₄O₃S₂	F(000) = 1192
M_r = 577.55	D_x = 1.427 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6963 reflections
a = 9.3334 (5) Å	θ = 3.5–29.0°
b = 10.3635 (4) Å	µ = 1.72 mm⁻¹
c = 27.8258 (11) Å	T = 293 K
β = 92.924 (4)°	Block, white
V = 2688.0 (2) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5266 independent reflections
Radiation source: fine-focus sealed tube	3580 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.043
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.5°
ω scan	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
T_min = 0.649, T_max = 1.000	l = −34→34
21429 measured reflections

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)] = 0.054	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.123	H-atom parameters constrained
S = 1.06	w = 1/[σ²(F_o²) + (0.0365P)² + 2.6423P] where P = (F_o² + 2F_c²)/3
5266 reflections	(Δ/σ)_max = 0.001
320 parameters	Δρ_max = 0.35 e Å⁻³
0 restraints	Δρ_min = −0.43 e Å⁻³

Crystal data top

C₂₅H₂₉BrN₄O₃S₂	V = 2688.0 (2) Å³
M_r = 577.55	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 9.3334 (5) Å	µ = 1.72 mm⁻¹
b = 10.3635 (4) Å	T = 293 K
c = 27.8258 (11) Å	0.3 × 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)
T_min = 0.649, T_max = 1.000	R_int = 0.043
21429 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.054	0 restraints
wR(F²) = 0.123	H-atom parameters constrained
S = 1.06	Δρ_max = 0.35 e Å⁻³
5266 reflections	Δρ_min = −0.43 e Å⁻³
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

	x	y	z	U_iso*/U_eq
Br1	0.24625 (5)	1.11199 (4)	0.216359 (17)	0.07602 (19)
S1	0.19179 (12)	0.85193 (11)	0.00058 (3)	0.0626 (3)
S2	0.10025 (10)	0.89654 (9)	0.14471 (3)	0.0513 (3)
O1	0.2090 (4)	0.7302 (3)	−0.02194 (10)	0.0849 (10)
O2	0.1541 (3)	0.9599 (3)	−0.02939 (9)	0.0725 (9)
O3	−0.0197 (3)	0.4244 (3)	0.15889 (9)	0.0700 (8)
N1	0.0612 (4)	0.8411 (3)	0.03700 (10)	0.0628 (9)
H1	0.0005	0.9035	0.0374	0.075*
N4	0.5272 (3)	0.8077 (3)	0.21918 (12)	0.0604 (9)
N5	0.3329 (3)	0.7523 (3)	0.16362 (10)	0.0453 (7)
N7	0.5265 (4)	0.6181 (3)	0.17624 (14)	0.0733 (10)
C1	0.3494 (4)	0.8878 (4)	0.03643 (12)	0.0523 (9)
C2	0.3591 (4)	1.0096 (4)	0.05852 (13)	0.0518 (9)
C3	0.4791 (4)	1.0346 (4)	0.08927 (14)	0.0612 (11)
H3	0.4856	1.1145	0.1045	0.073*
C4	0.5867 (5)	0.9480 (5)	0.09806 (14)	0.0646 (12)
C5	0.5758 (5)	0.8317 (5)	0.07489 (15)	0.0699 (12)
H5	0.6498	0.7725	0.0801	0.084*
C6	0.4601 (5)	0.7970 (4)	0.04384 (15)	0.0652 (11)
C7	0.2507 (5)	1.1154 (4)	0.05177 (17)	0.0712 (12)
H7A	0.2515	1.1474	0.0194	0.107*
H7B	0.2740	1.1842	0.0739	0.107*
H7C	0.1571	1.0825	0.0576	0.107*
C8	0.7134 (5)	0.9787 (6)	0.13240 (16)	0.0922 (17)
H8A	0.7873	1.0196	0.1151	0.138*
H8B	0.7499	0.9002	0.1467	0.138*
H8C	0.6832	1.0356	0.1572	0.138*
C9	0.0417 (4)	0.7345 (4)	0.06810 (12)	0.0555 (10)
C10	−0.0028 (6)	0.6177 (5)	0.04949 (15)	0.0934 (18)
H10	−0.0200	0.6100	0.0164	0.112*
C11	−0.0228 (6)	0.5119 (5)	0.07801 (15)	0.0879 (17)
H11	−0.0506	0.4335	0.0642	0.106*
C12	−0.0016 (4)	0.5222 (4)	0.12717 (13)	0.0549 (10)
C13	0.0332 (4)	0.6404 (4)	0.14644 (12)	0.0500 (9)
H13	0.0404	0.6497	0.1797	0.060*
C14	0.0579 (4)	0.7461 (4)	0.11776 (12)	0.0449 (8)
C15	−0.0514 (6)	0.2991 (4)	0.14117 (17)	0.0791 (14)
H15A	−0.1376	0.3018	0.1209	0.119*
H15B	−0.0645	0.2418	0.1677	0.119*
H15C	0.0265	0.2689	0.1229	0.119*
C16	0.2696 (4)	0.8624 (3)	0.17246 (11)	0.0406 (8)
C17	0.3325 (4)	0.9525 (3)	0.20396 (12)	0.0466 (9)
C18	0.4616 (4)	0.7291 (4)	0.18658 (13)	0.0504 (9)
C21	0.4617 (4)	0.9181 (4)	0.22662 (13)	0.0580 (10)
H21	0.5051	0.9760	0.2484	0.070*
C22	0.6581 (5)	0.5732 (5)	0.2017 (2)	0.0938 (16)
H22A	0.6940	0.6396	0.2237	0.113*
H22B	0.7306	0.5566	0.1787	0.113*
C23	0.6303 (6)	0.4531 (6)	0.2290 (2)	0.110 (2)
H23A	0.5689	0.4732	0.2551	0.131*
H23B	0.7204	0.4206	0.2431	0.131*
C24	0.5602 (7)	0.3496 (6)	0.1980 (3)	0.124 (2)
H24A	0.5336	0.2776	0.2179	0.148*
H24B	0.6275	0.3183	0.1752	0.148*
C25	0.4283 (6)	0.4025 (5)	0.1711 (2)	0.1031 (19)
H25A	0.3898	0.3377	0.1488	0.124*
H25B	0.3556	0.4214	0.1938	0.124*
C26	0.4612 (6)	0.5222 (5)	0.14396 (18)	0.0857 (15)
H26A	0.5261	0.5019	0.1189	0.103*
H26B	0.3735	0.5567	0.1288	0.103*
C27	0.4663 (7)	0.6661 (5)	0.0203 (2)	0.113 (2)
H27A	0.5549	0.6244	0.0300	0.169*
H27B	0.4606	0.6762	−0.0141	0.169*
H27C	0.3873	0.6144	0.0299	0.169*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0919 (4)	0.0579 (3)	0.0777 (3)	−0.0032 (2)	−0.0005 (3)	−0.0240 (2)
S1	0.0804 (8)	0.0720 (7)	0.0346 (5)	−0.0331 (6)	−0.0047 (5)	0.0008 (5)
S2	0.0549 (6)	0.0503 (5)	0.0476 (5)	−0.0009 (5)	−0.0081 (4)	−0.0051 (4)
O1	0.117 (3)	0.085 (2)	0.0528 (17)	−0.039 (2)	−0.0007 (17)	−0.0228 (16)
O2	0.077 (2)	0.095 (2)	0.0442 (15)	−0.0272 (17)	−0.0060 (14)	0.0220 (15)
O3	0.103 (2)	0.0584 (17)	0.0485 (15)	−0.0251 (16)	0.0001 (15)	0.0052 (14)
N1	0.069 (2)	0.077 (2)	0.0421 (17)	−0.0288 (19)	−0.0059 (15)	0.0138 (17)
N4	0.055 (2)	0.067 (2)	0.058 (2)	−0.0087 (18)	−0.0134 (16)	−0.0050 (18)
N5	0.0479 (18)	0.0480 (18)	0.0394 (16)	−0.0064 (14)	−0.0029 (13)	−0.0011 (14)
N7	0.067 (2)	0.062 (2)	0.088 (3)	0.0127 (19)	−0.018 (2)	−0.008 (2)
C1	0.063 (2)	0.055 (2)	0.0388 (19)	−0.016 (2)	0.0010 (17)	−0.0008 (18)
C2	0.051 (2)	0.059 (2)	0.046 (2)	−0.013 (2)	0.0029 (17)	0.0005 (19)
C3	0.061 (3)	0.073 (3)	0.049 (2)	−0.024 (2)	0.003 (2)	−0.009 (2)
C4	0.052 (3)	0.099 (4)	0.043 (2)	−0.016 (3)	0.0038 (19)	0.008 (2)
C5	0.060 (3)	0.089 (3)	0.061 (3)	0.007 (3)	0.008 (2)	0.016 (3)
C6	0.080 (3)	0.062 (3)	0.054 (2)	−0.008 (2)	0.010 (2)	−0.003 (2)
C7	0.075 (3)	0.061 (3)	0.077 (3)	−0.009 (2)	−0.004 (2)	−0.013 (2)
C8	0.058 (3)	0.154 (5)	0.063 (3)	−0.027 (3)	−0.008 (2)	0.016 (3)
C9	0.067 (3)	0.063 (2)	0.0353 (19)	−0.032 (2)	−0.0038 (17)	0.0024 (18)
C10	0.156 (5)	0.090 (4)	0.034 (2)	−0.069 (4)	0.004 (3)	−0.008 (2)
C11	0.146 (5)	0.075 (3)	0.043 (2)	−0.061 (3)	0.013 (3)	−0.012 (2)
C12	0.067 (3)	0.057 (2)	0.041 (2)	−0.023 (2)	0.0038 (18)	0.0000 (19)
C13	0.054 (2)	0.064 (3)	0.0313 (18)	−0.0146 (19)	−0.0020 (16)	−0.0010 (18)
C14	0.043 (2)	0.055 (2)	0.0353 (18)	−0.0125 (17)	−0.0051 (15)	−0.0019 (17)
C15	0.102 (4)	0.052 (3)	0.083 (3)	−0.015 (3)	0.005 (3)	0.000 (2)
C16	0.048 (2)	0.045 (2)	0.0282 (16)	−0.0126 (17)	0.0002 (14)	0.0024 (15)
C17	0.055 (2)	0.048 (2)	0.0370 (19)	−0.0115 (18)	0.0042 (17)	−0.0042 (16)
C18	0.051 (2)	0.054 (2)	0.046 (2)	−0.0048 (19)	−0.0029 (18)	0.0033 (18)
C21	0.065 (3)	0.064 (3)	0.045 (2)	−0.019 (2)	−0.0068 (19)	−0.009 (2)
C22	0.058 (3)	0.093 (4)	0.129 (5)	0.014 (3)	−0.007 (3)	0.003 (4)
C23	0.064 (3)	0.132 (5)	0.131 (5)	0.015 (3)	−0.015 (3)	0.053 (4)
C24	0.085 (4)	0.083 (4)	0.200 (7)	−0.002 (3)	−0.019 (4)	0.042 (5)
C25	0.088 (4)	0.073 (3)	0.145 (5)	−0.006 (3)	−0.022 (4)	0.006 (4)
C26	0.099 (4)	0.072 (3)	0.085 (3)	0.023 (3)	−0.010 (3)	−0.016 (3)
C27	0.159 (6)	0.076 (4)	0.102 (4)	0.015 (4)	−0.002 (4)	−0.023 (3)

Geometric parameters (Å, º) top

Br1—C17	1.878 (4)	C8—H8C	0.9600
S1—O1	1.422 (3)	C9—C10	1.373 (5)
S1—O2	1.429 (3)	C9—C14	1.388 (5)
S1—N1	1.628 (3)	C10—C11	1.372 (6)
S1—C1	1.774 (4)	C10—H10	0.9300
S2—C16	1.760 (4)	C11—C12	1.376 (5)
S2—C14	1.766 (4)	C11—H11	0.9300
O3—C12	1.360 (4)	C12—C13	1.369 (5)
O3—C15	1.415 (5)	C13—C14	1.382 (5)
N1—C9	1.420 (5)	C13—H13	0.9300
N1—H1	0.8600	C15—H15A	0.9600
N4—C21	1.319 (5)	C15—H15B	0.9600
N4—C18	1.343 (5)	C15—H15C	0.9600
N5—C16	1.313 (4)	C16—C17	1.390 (4)
N5—C18	1.353 (4)	C17—C21	1.379 (5)
N7—C18	1.339 (5)	C21—H21	0.9300
N7—C26	1.452 (6)	C22—C23	1.488 (7)
N7—C22	1.461 (6)	C22—H22A	0.9700
C1—C2	1.405 (5)	C22—H22B	0.9700
C1—C6	1.405 (6)	C23—C24	1.505 (8)
C2—C3	1.398 (5)	C23—H23A	0.9700
C2—C7	1.497 (6)	C23—H23B	0.9700
C3—C4	1.360 (6)	C24—C25	1.511 (7)
C3—H3	0.9300	C24—H24A	0.9700
C4—C5	1.368 (6)	C24—H24B	0.9700
C4—C8	1.516 (6)	C25—C26	1.493 (7)
C5—C6	1.395 (6)	C25—H25A	0.9700
C5—H5	0.9300	C25—H25B	0.9700
C6—C27	1.509 (6)	C26—H26A	0.9700
C7—H7A	0.9600	C26—H26B	0.9700
C7—H7B	0.9600	C27—H27A	0.9600
C7—H7C	0.9600	C27—H27B	0.9600
C8—H8A	0.9600	C27—H27C	0.9600
C8—H8B	0.9600

O1—S1—O2	117.88 (18)	C12—C13—H13	119.1
O1—S1—N1	108.56 (19)	C14—C13—H13	119.1
O2—S1—N1	104.34 (19)	C13—C14—C9	119.6 (3)
O1—S1—C1	108.9 (2)	C13—C14—S2	119.7 (3)
O2—S1—C1	109.66 (17)	C9—C14—S2	120.7 (3)
N1—S1—C1	106.87 (16)	O3—C15—H15A	109.5
C16—S2—C14	100.67 (17)	O3—C15—H15B	109.5
C12—O3—C15	119.2 (3)	H15A—C15—H15B	109.5
C9—N1—S1	123.8 (3)	O3—C15—H15C	109.5
C9—N1—H1	118.1	H15A—C15—H15C	109.5
S1—N1—H1	118.1	H15B—C15—H15C	109.5
C21—N4—C18	115.7 (3)	N5—C16—C17	121.5 (3)
C16—N5—C18	117.5 (3)	N5—C16—S2	119.7 (2)
C18—N7—C26	122.7 (4)	C17—C16—S2	118.8 (3)
C18—N7—C22	123.2 (4)	C21—C17—C16	116.4 (3)
C26—N7—C22	113.4 (4)	C21—C17—Br1	121.1 (3)
C2—C1—C6	120.5 (4)	C16—C17—Br1	122.4 (3)
C2—C1—S1	117.9 (3)	N7—C18—N4	118.1 (4)
C6—C1—S1	121.6 (3)	N7—C18—N5	116.9 (3)
C3—C2—C1	117.8 (4)	N4—C18—N5	125.1 (4)
C3—C2—C7	117.1 (4)	N4—C21—C17	123.7 (3)
C1—C2—C7	125.1 (3)	N4—C21—H21	118.2
C4—C3—C2	123.3 (4)	C17—C21—H21	118.2
C4—C3—H3	118.4	N7—C22—C23	110.5 (4)
C2—C3—H3	118.4	N7—C22—H22A	109.6
C3—C4—C5	117.4 (4)	C23—C22—H22A	109.6
C3—C4—C8	121.4 (5)	N7—C22—H22B	109.6
C5—C4—C8	121.2 (5)	C23—C22—H22B	109.6
C4—C5—C6	123.7 (4)	H22A—C22—H22B	108.1
C4—C5—H5	118.1	C22—C23—C24	112.6 (5)
C6—C5—H5	118.1	C22—C23—H23A	109.1
C5—C6—C1	117.3 (4)	C24—C23—H23A	109.1
C5—C6—C27	117.1 (5)	C22—C23—H23B	109.1
C1—C6—C27	125.6 (4)	C24—C23—H23B	109.1
C2—C7—H7A	109.5	H23A—C23—H23B	107.8
C2—C7—H7B	109.5	C23—C24—C25	110.1 (5)
H7A—C7—H7B	109.5	C23—C24—H24A	109.6
C2—C7—H7C	109.5	C25—C24—H24A	109.6
H7A—C7—H7C	109.5	C23—C24—H24B	109.6
H7B—C7—H7C	109.5	C25—C24—H24B	109.6
C4—C8—H8A	109.5	H24A—C24—H24B	108.1
C4—C8—H8B	109.5	C26—C25—C24	111.6 (5)
H8A—C8—H8B	109.5	C26—C25—H25A	109.3
C4—C8—H8C	109.5	C24—C25—H25A	109.3
H8A—C8—H8C	109.5	C26—C25—H25B	109.3
H8B—C8—H8C	109.5	C24—C25—H25B	109.3
C10—C9—C14	117.9 (3)	H25A—C25—H25B	108.0
C10—C9—N1	120.1 (3)	N7—C26—C25	110.3 (4)
C14—C9—N1	121.9 (3)	N7—C26—H26A	109.6
C11—C10—C9	122.3 (4)	C25—C26—H26A	109.6
C11—C10—H10	118.9	N7—C26—H26B	109.6
C9—C10—H10	118.9	C25—C26—H26B	109.6
C10—C11—C12	119.7 (4)	H26A—C26—H26B	108.1
C10—C11—H11	120.1	C6—C27—H27A	109.5
C12—C11—H11	120.1	C6—C27—H27B	109.5
O3—C12—C13	116.6 (3)	H27A—C27—H27B	109.5
O3—C12—C11	124.8 (4)	C6—C27—H27C	109.5
C13—C12—C11	118.6 (4)	H27A—C27—H27C	109.5
C12—C13—C14	121.7 (3)	H27B—C27—H27C	109.5

O1—S1—N1—C9	42.9 (3)	C12—C13—C14—C9	2.6 (6)
O2—S1—N1—C9	169.4 (3)	C12—C13—C14—S2	179.2 (3)
C1—S1—N1—C9	−74.5 (3)	C10—C9—C14—C13	1.8 (6)
O1—S1—C1—C2	174.6 (3)	N1—C9—C14—C13	177.9 (4)
O2—S1—C1—C2	44.2 (3)	C10—C9—C14—S2	−174.7 (4)
N1—S1—C1—C2	−68.3 (3)	N1—C9—C14—S2	1.4 (5)
O1—S1—C1—C6	−7.1 (4)	C16—S2—C14—C13	67.1 (3)
O2—S1—C1—C6	−137.5 (3)	C16—S2—C14—C9	−116.3 (3)
N1—S1—C1—C6	110.0 (3)	C18—N5—C16—C17	0.4 (5)
C6—C1—C2—C3	−2.4 (5)	C18—N5—C16—S2	−178.6 (2)
S1—C1—C2—C3	175.9 (3)	C14—S2—C16—N5	8.3 (3)
C6—C1—C2—C7	177.6 (4)	C14—S2—C16—C17	−170.8 (3)
S1—C1—C2—C7	−4.1 (5)	N5—C16—C17—C21	−2.3 (5)
C1—C2—C3—C4	1.0 (6)	S2—C16—C17—C21	176.7 (3)
C7—C2—C3—C4	−179.0 (4)	N5—C16—C17—Br1	178.8 (2)
C2—C3—C4—C5	0.8 (6)	S2—C16—C17—Br1	−2.2 (4)
C2—C3—C4—C8	−178.9 (4)	C26—N7—C18—N4	175.9 (4)
C3—C4—C5—C6	−1.3 (6)	C22—N7—C18—N4	5.7 (6)
C8—C4—C5—C6	178.4 (4)	C26—N7—C18—N5	−3.1 (6)
C4—C5—C6—C1	−0.1 (6)	C22—N7—C18—N5	−173.3 (4)
C4—C5—C6—C27	178.7 (4)	C21—N4—C18—N7	177.3 (4)
C2—C1—C6—C5	2.0 (6)	C21—N4—C18—N5	−3.7 (6)
S1—C1—C6—C5	−176.3 (3)	C16—N5—C18—N7	−178.3 (3)
C2—C1—C6—C27	−176.6 (4)	C16—N5—C18—N4	2.8 (5)
S1—C1—C6—C27	5.1 (6)	C18—N4—C21—C17	1.5 (6)
S1—N1—C9—C10	−71.3 (5)	C16—C17—C21—N4	1.3 (6)
S1—N1—C9—C14	112.7 (4)	Br1—C17—C21—N4	−179.8 (3)
C14—C9—C10—C11	−4.0 (8)	C18—N7—C22—C23	114.5 (5)
N1—C9—C10—C11	179.8 (5)	C26—N7—C22—C23	−56.6 (6)
C9—C10—C11—C12	1.7 (9)	N7—C22—C23—C24	53.4 (7)
C15—O3—C12—C13	−178.0 (4)	C22—C23—C24—C25	−52.3 (7)
C15—O3—C12—C11	5.4 (7)	C23—C24—C25—C26	53.1 (7)
C10—C11—C12—O3	179.3 (5)	C18—N7—C26—C25	−113.2 (5)
C10—C11—C12—C13	2.8 (8)	C22—N7—C26—C25	57.9 (6)
O3—C12—C13—C14	178.3 (3)	C24—C25—C26—N7	−55.7 (7)
C11—C12—C13—C14	−5.0 (6)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	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.

Experimental details

Crystal data
Chemical formula	C₂₅H₂₉BrN₄O₃S₂
M_r	577.55
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	9.3334 (5), 10.3635 (4), 27.8258 (11)
β (°)	92.924 (4)
V (Å³)	2688.0 (2)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.72
Crystal size (mm)	0.3 × 0.2 × 0.2

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.649, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21429, 5266, 3580
R_int	0.043
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.054, 0.123, 1.06
No. of reflections	5266
No. of parameters	320
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	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···A	D—H	H···A	D···A	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.

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

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

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Volume 68| Part 9| September 2012| Page o2767

doi:10.1107/S1600536812036185

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

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

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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