N-[2-(5-Bromo-2-morpholin-4-ylpyrim­idin-4-ylsulfan­yl)-4-meth­oxy­phen­yl]-2,4,6-trimethyl­benzene­sulfonamide

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

doi:10.1107/S1600536812040792

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3061

doi:10.1107/S1600536812040792

Open

access

N-[2-(5-Bromo-2-morpholin-4-ylpyrimidin-4-ylsulfanyl)-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 25 September 2012; accepted 27 September 2012; online 3 October 2012)

In the title compound, C₂₄H₂₇BrN₄O₄S₂, the molecule is twisted at the sulfonyl S atom with a C—S(O₂)—N(H)—C torsion angle of 62.6 (3)°. The benzene rings bridged by the sulfonamide group are tilted to each other by a dihedral angle of 60.6 (1)°. The dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 62.7 (1)°. The morpholine ring adopts a chair conformation. 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 = 3.793 (2) Å]. In the crystal, molecules are linked by N—H⋯O hydrogen bonds into a chain along the b axis.

Related literature

For related structures of sulfonamides, see: Rodrigues et al. (2011 ); Akkurt et al. (2011 ); Kant et al. (2012 ). For bond-length data, see: Allen et al. (1987 ). For ring conformations, see: Duax & Norton (1975 ).

Experimental

Crystal data

C₂₄H₂₇BrN₄O₄S₂
M_r = 579.53
Monoclinic, P 2₁ /n
a = 10.2583 (4) Å
b = 17.4727 (6) Å
c = 14.4375 (7) Å
β = 97.199 (4)°
V = 2567.38 (18) Å³
Z = 4
Mo Kα radiation
μ = 1.80 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 = 0.526, T_max = 0.697
19056 measured reflections
5023 independent reflections
3359 reflections with I > 2σ(I)
R_int = 0.045

Refinement

R[F² > 2σ(F²)] = 0.046
wR(F²) = 0.105
S = 1.02
5023 reflections
321 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O25ⁱ	0.86	2.09	2.890 (4)	155
Symmetry code: (i) $[-x+{\script{3\over 2}}, y-{\script{1\over 2}}, -z+{\script{1\over 2}}]$ .

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/S1600536812040792/is5200sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812040792/is5200Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812040792/is5200Isup3.cml

checkCIF report

Comment top

Bond lengths and angles in the title compound (Fig. 1) have normal values (Allen et al., 1987) and are comparable with the similar crystal structures (Rodrigues et al., 2011; Akkurt et al., 2011; Kant et al., 2012). The molecule is twisted at the S atom with the C2—S1—N1—C10 torsion angle of 62.6 (3)°. The morpholine ring is exhibiting chair conformation (asymmetry parameters are: [ΔC2(N22—C27) = 2.51; ΔCs(C24—C27) = 0.92] (Duax & Norton, 1975). The benzene C1–C6 and C10–C15 rings are tilted relative to each other by 60.6 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 62.7 (1) °. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine C16/N17/C18/N19/C20/C21 ring (centroid Cg1) and the 2,4,6-trimethyl benzene C1–C6 ring (centroid Cg2) [Cg1···Cg2 3.793 (2) Å, perpendicular distance of Cg1 on the C1–C6 ring 3.5103 (13) Å and perpendicular distance of Cg2 on the C16/N17/C18/N19/C20/C21 ring 3.3905 (12) Å]. In the crystal, molecules are linked into chains by N1—H1···O25 hydrogen bonds (Table 1 and Fig. 2).

Related literature top

For related structures of sulfonamides, see: Rodrigues et al. (2011); Akkurt et al. (2011); Kant et al. (2012). For bond-length data, see: Allen et al. (1987). For ring conformations, see: Duax & Norton (1975).

Experimental top

The reaction of N-[2-(5-bromo-2-morpholin-4-yl-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-2,4,6-trimethyl-benzenesulfonamide (5.29 g, 0.01 mol) with morpholine (0.88 g, 0.01 mol) 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 83%, m.p. 454–456 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. ORTEP view of the molecule with the atom-labeling scheme. The displacement ellipsoids are drawn at the 40% probability level. H atoms are shown as small spheres of arbitrary radii.
	Fig. 2. A molecular packing view of the title compound down the a axis, showing intermolecular interactions (dashed lines). For clarity, H atoms not involved in the hydrogen bonds have been omitted.

N-[2-(5-Bromo-2-morpholin-4-ylpyrimidin-4-ylsulfanyl)-4-methoxyphenyl]- 2,4,6-trimethylbenzenesulfonamide top

Crystal data top

C₂₄H₂₇BrN₄O₄S₂	F(000) = 1192
M_r = 579.53	D_x = 1.499 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6670 reflections
a = 10.2583 (4) Å	θ = 3.7–29.0°
b = 17.4727 (6) Å	µ = 1.80 mm⁻¹
c = 14.4375 (7) Å	T = 293 K
β = 97.199 (4)°	Block, brown
V = 2567.38 (18) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5023 independent reflections
Radiation source: fine-focus sealed tube	3359 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.045
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
ω scan	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
T_min = 0.526, T_max = 0.697	l = −17→17
19056 measured reflections

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.046	H-atom parameters constrained
wR(F²) = 0.105	w = 1/[σ²(F_o²) + (0.0338P)² + 1.6315P] where P = (F_o² + 2F_c²)/3
S = 1.02	(Δ/σ)_max = 0.001
5023 reflections	Δρ_max = 0.31 e Å⁻³
321 parameters	Δρ_min = −0.39 e Å⁻³
0 restraints	Extinction correction: SHELXL, Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0057 (4)

Crystal data top

C₂₄H₂₇BrN₄O₄S₂	V = 2567.38 (18) Å³
M_r = 579.53	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.2583 (4) Å	µ = 1.80 mm⁻¹
b = 17.4727 (6) Å	T = 293 K
c = 14.4375 (7) Å	0.3 × 0.2 × 0.2 mm
β = 97.199 (4)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	5023 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3359 reflections with I > 2σ(I)
T_min = 0.526, T_max = 0.697	R_int = 0.045
19056 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.046	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.02	Δρ_max = 0.31 e Å⁻³
5023 reflections	Δρ_min = −0.39 e Å⁻³
321 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	1.02664 (4)	0.10295 (2)	0.23807 (3)	0.07706 (19)
S1	0.50455 (9)	0.24940 (6)	0.00299 (6)	0.0566 (3)
S2	0.74901 (8)	0.19238 (5)	0.24649 (6)	0.0472 (2)
N1	0.5008 (2)	0.22120 (16)	0.11087 (18)	0.0487 (7)
H1	0.4848	0.1739	0.1215	0.058*
O1	0.4808 (3)	0.18139 (17)	−0.05220 (17)	0.0788 (8)
O2	0.4152 (2)	0.31164 (17)	−0.01409 (18)	0.0774 (8)
O3	0.5639 (3)	0.42389 (15)	0.41145 (19)	0.0704 (7)
C1	0.6672 (3)	0.28269 (18)	−0.0041 (2)	0.0430 (8)
C2	0.6972 (4)	0.36148 (19)	−0.0014 (2)	0.0508 (9)
C3	0.8256 (4)	0.3831 (2)	−0.0079 (2)	0.0562 (9)
H3	0.8455	0.4350	−0.0071	0.067*
C4	0.9252 (3)	0.3316 (2)	−0.0154 (2)	0.0535 (9)
C5	0.8941 (3)	0.2553 (2)	−0.0154 (2)	0.0527 (9)
H5	0.9608	0.2197	−0.0187	0.063*
C6	0.7666 (3)	0.22861 (18)	−0.0106 (2)	0.0460 (8)
C7	0.7498 (4)	0.14289 (19)	−0.0125 (3)	0.0681 (11)
H7A	0.7078	0.1274	−0.0727	0.102*
H7B	0.6966	0.1278	0.0346	0.102*
H7C	0.8344	0.1188	−0.0005	0.102*
C8	1.0642 (4)	0.3581 (3)	−0.0207 (3)	0.0791 (12)
H8A	1.0826	0.3555	−0.0842	0.119*
H8B	1.1244	0.3257	0.0176	0.119*
H8C	1.0740	0.4100	0.0011	0.119*
C9	0.6004 (4)	0.4257 (2)	0.0093 (3)	0.0787 (13)
H9A	0.5321	0.4249	−0.0427	0.118*
H9B	0.6453	0.4739	0.0110	0.118*
H9C	0.5625	0.4187	0.0662	0.118*
C10	0.5231 (3)	0.27276 (18)	0.1873 (2)	0.0412 (7)
C11	0.4332 (3)	0.3308 (2)	0.1984 (2)	0.0532 (9)
H11	0.3594	0.3360	0.1544	0.064*
C12	0.4508 (3)	0.3801 (2)	0.2724 (3)	0.0553 (9)
H12	0.3902	0.4191	0.2774	0.066*
C13	0.5583 (3)	0.3723 (2)	0.3399 (2)	0.0503 (8)
C14	0.6476 (3)	0.31466 (18)	0.3324 (2)	0.0446 (8)
H14	0.7183	0.3082	0.3787	0.054*
C15	0.6321 (3)	0.26588 (18)	0.2552 (2)	0.0409 (7)
C16	0.8899 (3)	0.24701 (19)	0.2337 (2)	0.0404 (7)
N17	0.8793 (2)	0.32166 (15)	0.22635 (17)	0.0414 (6)
C18	0.9896 (3)	0.3618 (2)	0.2209 (2)	0.0490 (8)
N19	1.1113 (3)	0.33241 (18)	0.2232 (2)	0.0611 (8)
C20	1.1185 (3)	0.2570 (2)	0.2294 (3)	0.0614 (10)
H20	1.2006	0.2341	0.2313	0.074*
C21	1.0110 (3)	0.2104 (2)	0.2331 (2)	0.0504 (8)
N22	0.9747 (3)	0.43869 (16)	0.2097 (2)	0.0575 (8)
C23	0.8513 (3)	0.4755 (2)	0.2241 (3)	0.0623 (10)
H23A	0.7806	0.4382	0.2173	0.075*
H23B	0.8303	0.5154	0.1780	0.075*
C24	0.8650 (4)	0.5089 (2)	0.3196 (3)	0.0726 (12)
H24A	0.7834	0.5335	0.3300	0.087*
H24B	0.8829	0.4685	0.3655	0.087*
O25	0.9689 (3)	0.56335 (15)	0.3307 (2)	0.0848 (9)
C25	0.6630 (4)	0.4143 (2)	0.4887 (3)	0.0773 (12)
H25A	0.6544	0.3647	0.5158	0.116*
H25B	0.6535	0.4531	0.5345	0.116*
H25C	0.7479	0.4187	0.4679	0.116*
C26	1.0905 (4)	0.5289 (2)	0.3180 (3)	0.0808 (14)
H26A	1.1128	0.4909	0.3663	0.097*
H26B	1.1589	0.5676	0.3241	0.097*
C27	1.0850 (3)	0.4917 (2)	0.2245 (3)	0.0679 (11)
H27A	1.0756	0.5306	0.1761	0.082*
H27B	1.1663	0.4643	0.2204	0.082*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0695 (3)	0.0623 (3)	0.1013 (4)	0.0199 (2)	0.0181 (2)	0.0000 (2)
S1	0.0426 (5)	0.0840 (7)	0.0398 (5)	−0.0032 (5)	−0.0080 (4)	−0.0043 (5)
S2	0.0379 (4)	0.0491 (5)	0.0532 (5)	−0.0001 (4)	0.0004 (4)	−0.0006 (4)
N1	0.0435 (16)	0.0588 (17)	0.0423 (16)	−0.0127 (14)	−0.0004 (12)	−0.0017 (14)
O1	0.0723 (18)	0.108 (2)	0.0522 (16)	−0.0252 (16)	−0.0088 (13)	−0.0267 (16)
O2	0.0485 (15)	0.118 (2)	0.0611 (17)	0.0205 (15)	−0.0109 (12)	0.0180 (16)
O3	0.0646 (17)	0.0829 (18)	0.0653 (18)	0.0025 (14)	0.0142 (14)	−0.0251 (15)
C1	0.0422 (18)	0.056 (2)	0.0294 (16)	0.0062 (16)	0.0000 (14)	−0.0014 (15)
C2	0.062 (2)	0.048 (2)	0.043 (2)	0.0115 (17)	0.0059 (17)	0.0018 (16)
C3	0.072 (3)	0.046 (2)	0.053 (2)	−0.0036 (19)	0.0172 (19)	0.0023 (17)
C4	0.056 (2)	0.062 (2)	0.045 (2)	−0.0007 (19)	0.0162 (16)	0.0007 (18)
C5	0.053 (2)	0.054 (2)	0.052 (2)	0.0127 (17)	0.0136 (17)	−0.0006 (17)
C6	0.057 (2)	0.0443 (18)	0.0370 (18)	0.0048 (16)	0.0079 (15)	−0.0056 (15)
C7	0.080 (3)	0.050 (2)	0.078 (3)	0.002 (2)	0.024 (2)	−0.011 (2)
C8	0.068 (3)	0.090 (3)	0.083 (3)	−0.013 (2)	0.024 (2)	−0.002 (2)
C9	0.079 (3)	0.061 (2)	0.097 (3)	0.027 (2)	0.014 (2)	0.000 (2)
C10	0.0296 (16)	0.0559 (19)	0.0381 (17)	−0.0055 (15)	0.0044 (13)	0.0027 (16)
C11	0.0321 (18)	0.072 (2)	0.054 (2)	0.0021 (17)	0.0027 (15)	0.006 (2)
C12	0.040 (2)	0.067 (2)	0.061 (2)	0.0101 (17)	0.0152 (17)	−0.003 (2)
C13	0.043 (2)	0.061 (2)	0.049 (2)	−0.0048 (17)	0.0149 (16)	−0.0064 (18)
C14	0.0362 (17)	0.062 (2)	0.0356 (18)	−0.0064 (16)	0.0027 (14)	0.0004 (16)
C15	0.0289 (16)	0.0535 (19)	0.0403 (18)	−0.0021 (14)	0.0043 (13)	0.0047 (15)
C16	0.0340 (17)	0.056 (2)	0.0294 (16)	0.0019 (15)	−0.0008 (12)	−0.0041 (15)
N17	0.0294 (14)	0.0520 (17)	0.0424 (15)	0.0012 (12)	0.0025 (11)	−0.0056 (13)
C18	0.0378 (19)	0.058 (2)	0.050 (2)	0.0022 (17)	0.0043 (15)	−0.0052 (17)
N19	0.0327 (16)	0.068 (2)	0.084 (2)	0.0034 (15)	0.0117 (15)	−0.0023 (18)
C20	0.0334 (19)	0.074 (3)	0.079 (3)	0.0102 (19)	0.0130 (18)	−0.001 (2)
C21	0.0423 (19)	0.058 (2)	0.051 (2)	0.0100 (17)	0.0057 (15)	−0.0047 (17)
N22	0.0324 (15)	0.0558 (18)	0.085 (2)	−0.0048 (14)	0.0119 (14)	−0.0099 (16)
C23	0.041 (2)	0.049 (2)	0.096 (3)	0.0003 (17)	0.007 (2)	0.002 (2)
C24	0.078 (3)	0.054 (2)	0.092 (3)	0.013 (2)	0.033 (2)	0.010 (2)
O25	0.081 (2)	0.0571 (17)	0.113 (3)	0.0073 (16)	−0.0002 (18)	−0.0187 (16)
C25	0.079 (3)	0.100 (3)	0.055 (2)	−0.021 (2)	0.014 (2)	−0.026 (2)
C26	0.065 (3)	0.057 (2)	0.112 (4)	−0.005 (2)	−0.022 (3)	0.001 (3)
C27	0.040 (2)	0.061 (2)	0.104 (3)	−0.0081 (18)	0.014 (2)	0.008 (2)

Geometric parameters (Å, º) top

Br1—C21	1.885 (3)	C11—C12	1.368 (5)
S1—O2	1.424 (3)	C11—H11	0.9300
S1—O1	1.434 (3)	C12—C13	1.384 (5)
S1—N1	1.639 (3)	C12—H12	0.9300
S1—C1	1.782 (3)	C13—C14	1.376 (4)
S2—C16	1.761 (3)	C14—C15	1.396 (4)
S2—C15	1.772 (3)	C14—H14	0.9300
N1—C10	1.421 (4)	C16—N17	1.312 (4)
N1—H1	0.8600	C16—C21	1.399 (4)
O3—C13	1.367 (4)	N17—C18	1.342 (4)
O3—C25	1.421 (5)	C18—N19	1.347 (4)
C1—C6	1.402 (4)	C18—N22	1.359 (4)
C1—C2	1.410 (4)	N19—C20	1.322 (4)
C2—C3	1.385 (5)	C20—C21	1.377 (5)
C2—C9	1.519 (5)	C20—H20	0.9300
C3—C4	1.375 (5)	N22—C27	1.457 (4)
C3—H3	0.9300	N22—C23	1.458 (4)
C4—C5	1.371 (5)	C23—C24	1.487 (5)
C4—C8	1.511 (5)	C23—H23A	0.9700
C5—C6	1.398 (5)	C23—H23B	0.9700
C5—H5	0.9300	C24—O25	1.423 (5)
C6—C7	1.508 (4)	C24—H24A	0.9700
C7—H7A	0.9600	C24—H24B	0.9700
C7—H7B	0.9600	O25—C26	1.417 (5)
C7—H7C	0.9600	C25—H25A	0.9600
C8—H8A	0.9600	C25—H25B	0.9600
C8—H8B	0.9600	C25—H25C	0.9600
C8—H8C	0.9600	C26—C27	1.493 (6)
C9—H9A	0.9600	C26—H26A	0.9700
C9—H9B	0.9600	C26—H26B	0.9700
C9—H9C	0.9600	C27—H27A	0.9700
C10—C11	1.393 (4)	C27—H27B	0.9700
C10—C15	1.396 (4)

O2—S1—O1	118.40 (17)	O3—C13—C12	115.0 (3)
O2—S1—N1	107.62 (16)	C14—C13—C12	119.8 (3)
O1—S1—N1	104.85 (16)	C13—C14—C15	120.0 (3)
O2—S1—C1	109.14 (16)	C13—C14—H14	120.0
O1—S1—C1	109.49 (16)	C15—C14—H14	120.0
N1—S1—C1	106.67 (13)	C14—C15—C10	120.6 (3)
C16—S2—C15	100.73 (15)	C14—C15—S2	119.2 (2)
C10—N1—S1	121.8 (2)	C10—C15—S2	120.1 (2)
C10—N1—H1	119.1	N17—C16—C21	121.2 (3)
S1—N1—H1	119.1	N17—C16—S2	119.1 (2)
C13—O3—C25	118.3 (3)	C21—C16—S2	119.6 (3)
C6—C1—C2	120.1 (3)	C16—N17—C18	117.6 (3)
C6—C1—S1	118.6 (2)	N17—C18—N19	125.8 (3)
C2—C1—S1	121.3 (2)	N17—C18—N22	116.2 (3)
C3—C2—C1	118.0 (3)	N19—C18—N22	118.1 (3)
C3—C2—C9	116.5 (3)	C20—N19—C18	115.2 (3)
C1—C2—C9	125.5 (3)	N19—C20—C21	123.6 (3)
C4—C3—C2	123.3 (3)	N19—C20—H20	118.2
C4—C3—H3	118.3	C21—C20—H20	118.2
C2—C3—H3	118.3	C20—C21—C16	116.5 (3)
C5—C4—C3	117.4 (3)	C20—C21—Br1	121.7 (3)
C5—C4—C8	121.3 (3)	C16—C21—Br1	121.8 (3)
C3—C4—C8	121.3 (3)	C18—N22—C27	122.5 (3)
C4—C5—C6	122.9 (3)	C18—N22—C23	120.3 (3)
C4—C5—H5	118.6	C27—N22—C23	111.8 (3)
C6—C5—H5	118.6	N22—C23—C24	108.8 (3)
C5—C6—C1	118.1 (3)	N22—C23—H23A	109.9
C5—C6—C7	115.8 (3)	C24—C23—H23A	109.9
C1—C6—C7	126.0 (3)	N22—C23—H23B	109.9
C6—C7—H7A	109.5	C24—C23—H23B	109.9
C6—C7—H7B	109.5	H23A—C23—H23B	108.3
H7A—C7—H7B	109.5	O25—C24—C23	110.5 (3)
C6—C7—H7C	109.5	O25—C24—H24A	109.6
H7A—C7—H7C	109.5	C23—C24—H24A	109.6
H7B—C7—H7C	109.5	O25—C24—H24B	109.6
C4—C8—H8A	109.5	C23—C24—H24B	109.6
C4—C8—H8B	109.5	H24A—C24—H24B	108.1
H8A—C8—H8B	109.5	C26—O25—C24	111.1 (3)
C4—C8—H8C	109.5	O3—C25—H25A	109.5
H8A—C8—H8C	109.5	O3—C25—H25B	109.5
H8B—C8—H8C	109.5	H25A—C25—H25B	109.5
C2—C9—H9A	109.5	O3—C25—H25C	109.5
C2—C9—H9B	109.5	H25A—C25—H25C	109.5
H9A—C9—H9B	109.5	H25B—C25—H25C	109.5
C2—C9—H9C	109.5	O25—C26—C27	111.6 (3)
H9A—C9—H9C	109.5	O25—C26—H26A	109.3
H9B—C9—H9C	109.5	C27—C26—H26A	109.3
C11—C10—C15	117.7 (3)	O25—C26—H26B	109.3
C11—C10—N1	120.4 (3)	C27—C26—H26B	109.3
C15—C10—N1	121.9 (3)	H26A—C26—H26B	108.0
C12—C11—C10	121.6 (3)	N22—C27—C26	110.5 (3)
C12—C11—H11	119.2	N22—C27—H27A	109.6
C10—C11—H11	119.2	C26—C27—H27A	109.6
C11—C12—C13	120.2 (3)	N22—C27—H27B	109.6
C11—C12—H12	119.9	C26—C27—H27B	109.6
C13—C12—H12	119.9	H27A—C27—H27B	108.1
O3—C13—C14	125.2 (3)

O2—S1—N1—C10	−54.4 (3)	C13—C14—C15—C10	−3.0 (5)
O1—S1—N1—C10	178.7 (2)	C13—C14—C15—S2	179.5 (2)
C1—S1—N1—C10	62.6 (3)	C11—C10—C15—C14	1.5 (4)
O2—S1—C1—C6	−165.8 (2)	N1—C10—C15—C14	−176.3 (3)
O1—S1—C1—C6	−34.8 (3)	C11—C10—C15—S2	179.0 (2)
N1—S1—C1—C6	78.2 (3)	N1—C10—C15—S2	1.2 (4)
O2—S1—C1—C2	15.5 (3)	C16—S2—C15—C14	−65.8 (3)
O1—S1—C1—C2	146.6 (3)	C16—S2—C15—C10	116.7 (3)
N1—S1—C1—C2	−100.5 (3)	C15—S2—C16—N17	−4.9 (3)
C6—C1—C2—C3	1.8 (5)	C15—S2—C16—C21	174.0 (3)
S1—C1—C2—C3	−179.6 (2)	C21—C16—N17—C18	−1.8 (4)
C6—C1—C2—C9	−177.5 (3)	S2—C16—N17—C18	177.1 (2)
S1—C1—C2—C9	1.2 (5)	C16—N17—C18—N19	−0.7 (5)
C1—C2—C3—C4	−1.0 (5)	C16—N17—C18—N22	177.5 (3)
C9—C2—C3—C4	178.3 (3)	N17—C18—N19—C20	1.6 (5)
C2—C3—C4—C5	−0.7 (5)	N22—C18—N19—C20	−176.6 (3)
C2—C3—C4—C8	−179.0 (3)	C18—N19—C20—C21	0.1 (6)
C3—C4—C5—C6	1.8 (5)	N19—C20—C21—C16	−2.4 (5)
C8—C4—C5—C6	180.0 (3)	N19—C20—C21—Br1	178.1 (3)
C4—C5—C6—C1	−1.0 (5)	N17—C16—C21—C20	3.3 (5)
C4—C5—C6—C7	179.3 (3)	S2—C16—C21—C20	−175.6 (3)
C2—C1—C6—C5	−0.8 (5)	N17—C16—C21—Br1	−177.2 (2)
S1—C1—C6—C5	−179.5 (2)	S2—C16—C21—Br1	3.9 (4)
C2—C1—C6—C7	178.9 (3)	N17—C18—N22—C27	165.2 (3)
S1—C1—C6—C7	0.2 (4)	N19—C18—N22—C27	−16.4 (5)
S1—N1—C10—C11	67.5 (4)	N17—C18—N22—C23	13.2 (5)
S1—N1—C10—C15	−114.8 (3)	N19—C18—N22—C23	−168.4 (3)
C15—C10—C11—C12	0.7 (5)	C18—N22—C23—C24	98.4 (4)
N1—C10—C11—C12	178.5 (3)	C27—N22—C23—C24	−56.4 (4)
C10—C11—C12—C13	−1.4 (5)	N22—C23—C24—O25	59.2 (4)
C25—O3—C13—C14	−5.5 (5)	C23—C24—O25—C26	−60.5 (4)
C25—O3—C13—C12	173.0 (3)	C24—O25—C26—C27	57.3 (5)
C11—C12—C13—O3	−178.6 (3)	C18—N22—C27—C26	−100.5 (4)
C11—C12—C13—C14	−0.1 (5)	C23—N22—C27—C26	53.6 (4)
O3—C13—C14—C15	−179.3 (3)	O25—C26—C27—N22	−53.4 (4)
C12—C13—C14—C15	2.3 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O25ⁱ	0.86	2.09	2.890 (4)	155

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Experimental details

Crystal data
Chemical formula	C₂₄H₂₇BrN₄O₄S₂
M_r	579.53
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.2583 (4), 17.4727 (6), 14.4375 (7)
β (°)	97.199 (4)
V (Å³)	2567.38 (18)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.80
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	0.526, 0.697
No. of measured, independent and observed [I > 2σ(I)] reflections	19056, 5023, 3359
R_int	0.045
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.046, 0.105, 1.02
No. of reflections	5023
No. of parameters	321
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), 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···O25ⁱ	0.86	2.09	2.890 (4)	155

Symmetry code: (i) −x+3/2, y−1/2, −z+1/2.

Acknowledgements

MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola 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
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. CrossRef Web of Science Google Scholar
Duax, W. L. & Norton, D. A. (1975). Atlas of Steroid Structures, Vol. 1. New York: Plenum Press. 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

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 11| November 2012| Page o3061

doi:10.1107/S1600536812040792

Open

access

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Format		BIBTeX
		EndNote
		RefMan
		Refer
		Medline
		CIF
		SGML
		Plain Text

Search IUCr Journals		doi		Advanced search
Author		volume	page

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

N-[2-(5-Bromo-2-morpholin-4-ylpyrim­idin-4-ylsulfan­yl)-4-meth­­oxy­phen­yl]-2,4,6-tri­methyl­benzene­sulfonamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-[2-(5-Bromo-2-morpholin-4-ylpyrimidin-4-ylsulfanyl)-4-methoxyphenyl]-2,4,6-trimethylbenzenesulfonamide