N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­oxy­phen­yl)-4-methyl­benzene­sulfonamide

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

doi:10.1107/S1600536812033375

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 68| Part 8| August 2012| Pages o2590-o2591

https://doi.org/10.1107/S1600536812033375

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N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)-4-methylbenzenesulfonamide

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

^aX-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics, University of Jammu, Jammu Tawi 180 006, India, ^bDepartment of Studies in Physics, Manasagangotri, University of Mysore, Mysore 570 006, India, and ^cPG Department of Studies in Chemistry, JSS College of Arts Commerce and Science, Ooty Road Mysore 570 025, India
^*Correspondence e-mail: rkvk.paper11@gmail.com

(Received 19 July 2012; accepted 24 July 2012; online 28 July 2012)

In the title compound, C₂₂H₂₃BrN₄O₄S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by 68.9 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.7 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 4-methylbenzene rings [centroid–centroid distance = 3.934 (2) Å]. The morpholine ring adopts a chair conformation and is disordered over two positions with an occupancy ratio of 0.853 (6):0.147 (6). In the crystal, molecules are linked by N—H⋯O hydrogen bonds into chains extending along the a axis and further, through C—H⋯N and C—H⋯O interactions, into a three-dimensional supramolecular structure.

Related literature

For the crystal structures of sulfonamides, see: Rodrigues et al. (2011 ); Akkurt et al. (2011 ). For their biological activity, see: Gao & Pederson (2005 ). For bond-length data, see: Allen et al. (1987 ). For ring asymmetry parameters and conformations, see: Duax & Norton (1975 ).

Experimental

Crystal data

C₂₂H₂₃BrN₄O₄S₂
M_r = 551.47
Monoclinic, P 2₁ /n
a = 10.0321 (3) Å
b = 17.4842 (6) Å
c = 13.9095 (4) Å
β = 91.699 (3)°
V = 2438.70 (13) Å³
Z = 4
Mo Kα radiation
μ = 1.89 mm⁻¹
T = 293 K
0.3 × 0.2 × 0.1 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 = 0.557, T_max = 1.000
21500 measured reflections
4783 independent reflections
3361 reflections with I > 2σ(I)
R_int = 0.040

Refinement

R[F² > 2σ(F²)] = 0.041
wR(F²) = 0.086
S = 1.01
4783 reflections
321 parameters
1 restraint
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.53 e Å⁻³
Δρ_min = −0.46 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O26Aⁱ	0.85 (2)	2.02 (2)	2.846 (8)	163 (2)
N8—H8⋯O26Bⁱ	0.85 (2)	2.06 (6)	2.895 (5)	165 (3)
C21—H21⋯N20ⁱⁱ	0.93	2.53	3.394 (4)	155
C25A—H251⋯O2ⁱⁱⁱ	0.97	2.59	3.377 (6)	138
C27A—H272⋯O2ⁱⁱⁱ	0.97	2.52	3.341 (6)	143
Symmetry codes: (i) x+1, y, z; (ii) -x+1, -y, -z+1; (iii) $[x-{\script{1\over 2}}, -y+{\script{1\over 2}}, z-{\script{1\over 2}}]$ .

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: https://doi.org/10.1107/S1600536812033375/gk2516sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812033375/gk2516Isup2.hkl

Supporting information file. DOI: https://doi.org/10.1107/S1600536812033375/gk2516Isup3.cml

checkCIF report

Comment top

The amide and sulfonamide moieties are the constituents of many biologically significant compounds. Sulfonamide compounds are well known as antimicrobial agents (Gao & Pederson, 2005). In the present work, the crystal structure of N-[2-(5-bromo-2-morpholin-4-yl-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-4- methyl-benzenesulfonamide has been determined.

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). The morpholine ring is disordered over two positions with the occupancy ratio of 0.853 (6):0.147 (6) and adopts chair conformation (asymmetry parameters:ΔC_s(C24A—C27A) = 1.30; ΔC₂(C24A—C25A) = 1.59; ΔC_s(C25B—C28B) = 2.37; ΔC₂(C25B—O26B) = 3.65 (Duax & Norton, 1975). The two benzene rings are tilted relative to each other by 68.9 (1)°. The dihedral angle formed by the pyrimidine ring with two benzene rings (C9—C14/C1—C6) are 69.7 (1) and 2.2 (1)°, respectively. In the crystal, molecules are connected via N—H···O, C—H···N and C—H···O hydrogen bonds.

Related literature top

For the crystal structures of sulfonamides, see: Rodrigues et al. (2011); Akkurt et al. (2011). For their biological activity, see: Gao & Pederson (2005). For bond-length data, see: Allen et al. (1987). For ring asymmetry parameters and conformations, see: Duax & Norton (1975).

Experimental top

The reaction of N-[2-(5-bromo-2-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]- 4-methyl-benzenesulfonamide (5.01 g, 0.01 mol) with morpholine (0.88g, 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 the residue was extracted with ethyl acetate. The compound was purified by successive recrystallization from methanol (yield 84%, m.p. 485-487 K).

Structure description top

For the crystal structures of sulfonamides, see: Rodrigues et al. (2011); Akkurt et al. (2011). For their biological activity, see: Gao & Pederson (2005). For bond-length data, see: Allen et al. (1987). For ring asymmetry parameters and conformations, see: Duax & Norton (1975).

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 crystal packing view of the title compound down the b axis, showing intermolecular interactions. For clarity, hydrogen atoms which are not involved in hydrogen bonding have been omitted.

N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfanyl}- 4-methoxyphenyl)-4-methylbenzenesulfonamide top

Crystal data top

C₂₂H₂₃BrN₄O₄S₂	F(000) = 1128
M_r = 551.47	D_x = 1.502 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 7219 reflections
a = 10.0321 (3) Å	θ = 3.5–29.0°
b = 17.4842 (6) Å	µ = 1.89 mm⁻¹
c = 13.9095 (4) Å	T = 293 K
β = 91.699 (3)°	Block, brown
V = 2438.70 (13) Å³	0.3 × 0.2 × 0.1 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4783 independent reflections
Radiation source: fine-focus sealed tube	3361 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.040
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
ω scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
T_min = 0.557, T_max = 1.000	l = −17→17
21500 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)] = 0.041	H atoms treated by a mixture of independent and constrained refinement
wR(F²) = 0.086	w = 1/[σ²(F_o²) + (0.0237P)² + 2.0098P] where P = (F_o² + 2F_c²)/3
S = 1.01	(Δ/σ)_max = 0.001
4783 reflections	Δρ_max = 0.53 e Å⁻³
321 parameters	Δρ_min = −0.46 e Å⁻³
1 restraint	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc^*=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0044 (3)

Crystal data top

C₂₂H₂₃BrN₄O₄S₂	V = 2438.70 (13) Å³
M_r = 551.47	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0321 (3) Å	µ = 1.89 mm⁻¹
b = 17.4842 (6) Å	T = 293 K
c = 13.9095 (4) Å	0.3 × 0.2 × 0.1 mm
β = 91.699 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4783 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3361 reflections with I > 2σ(I)
T_min = 0.557, T_max = 1.000	R_int = 0.040
21500 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.041	1 restraint
wR(F²) = 0.086	H atoms treated by a mixture of independent and constrained refinement
S = 1.01	Δρ_max = 0.53 e Å⁻³
4783 reflections	Δρ_min = −0.46 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 esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	Occ. (<1)
Br1	0.83360 (4)	0.11861 (2)	0.46770 (3)	0.06867 (15)
S1	0.87974 (10)	0.20496 (6)	0.92605 (6)	0.0704 (3)
S2	0.80399 (7)	0.25279 (5)	0.62864 (5)	0.0479 (2)
O1	1.0028 (3)	0.16380 (17)	0.9297 (2)	0.0948 (9)
O2	0.8356 (3)	0.24415 (16)	1.00940 (17)	0.0942 (9)
C1	0.7515 (3)	0.14086 (19)	0.8915 (2)	0.0580 (9)
C2	0.7717 (4)	0.0890 (2)	0.8185 (3)	0.0658 (9)
H2	0.8513	0.0896	0.7858	0.079*
C3	0.6747 (4)	0.0365 (2)	0.7942 (3)	0.0705 (10)
H3	0.6889	0.0025	0.7441	0.085*
C4	0.5572 (4)	0.0332 (2)	0.8422 (3)	0.0750 (11)
C5	0.5381 (4)	0.0859 (3)	0.9135 (3)	0.0899 (13)
H5	0.4585	0.0852	0.9462	0.108*
C6	0.6332 (4)	0.1399 (2)	0.9384 (3)	0.0805 (11)
H6	0.6173	0.1754	0.9865	0.097*
C7	0.4547 (5)	−0.0272 (3)	0.8165 (4)	0.1122 (16)
H71	0.3785	−0.0209	0.8559	0.168*
H72	0.4926	−0.0770	0.8274	0.168*
H73	0.4279	−0.0222	0.7500	0.168*
N8	0.8941 (3)	0.26764 (16)	0.84004 (19)	0.0557 (7)
C9	0.7866 (3)	0.31561 (17)	0.8096 (2)	0.0451 (7)
C10	0.7358 (3)	0.31454 (16)	0.71564 (19)	0.0415 (7)
C11	0.6332 (3)	0.36306 (17)	0.6863 (2)	0.0465 (7)
H11	0.6023	0.3627	0.6226	0.056*
C12	0.5771 (3)	0.41192 (18)	0.7516 (2)	0.0510 (8)
C13	0.6270 (3)	0.41381 (19)	0.8452 (2)	0.0575 (9)
H13	0.5896	0.4468	0.8894	0.069*
C14	0.7313 (3)	0.36729 (19)	0.8733 (2)	0.0552 (8)
H14	0.7657	0.3704	0.9361	0.066*
O15	0.4760 (2)	0.46199 (13)	0.72933 (18)	0.0700 (7)
C16	0.4322 (4)	0.4661 (2)	0.6311 (3)	0.0917 (13)
H161	0.5074	0.4750	0.5915	0.138*
H162	0.3695	0.5072	0.6229	0.138*
H163	0.3902	0.4187	0.6127	0.138*
C17	0.6708 (3)	0.18839 (16)	0.61096 (18)	0.0383 (6)
N18	0.5635 (2)	0.19533 (13)	0.66305 (15)	0.0399 (5)
C19	0.4636 (3)	0.14544 (17)	0.6460 (2)	0.0435 (7)
N20	0.4648 (3)	0.08807 (15)	0.5818 (2)	0.0587 (7)
C21	0.5749 (3)	0.08278 (19)	0.5312 (2)	0.0606 (9)
H21	0.5801	0.0439	0.4858	0.073*
C22	0.6803 (3)	0.13110 (17)	0.5425 (2)	0.0471 (7)
N23	0.3546 (2)	0.15296 (15)	0.70003 (19)	0.0545 (7)
C24A	0.2340 (5)	0.1087 (3)	0.6840 (4)	0.0640 (14)	0.853 (6)
H241	0.2103	0.0832	0.7430	0.077*	0.853 (6)
H242	0.2484	0.0699	0.6355	0.077*	0.853 (6)
C25A	0.1230 (4)	0.1615 (3)	0.6511 (4)	0.0714 (15)	0.853 (6)
H251	0.1428	0.1825	0.5886	0.086*	0.853 (6)
H252	0.0403	0.1329	0.6447	0.086*	0.853 (6)
O26A	0.1073 (7)	0.2244 (3)	0.7210 (6)	0.093 (2)	0.853 (6)
C27A	0.2260 (4)	0.2649 (3)	0.7336 (4)	0.0690 (14)	0.853 (6)
H271	0.2130	0.3061	0.7791	0.083*	0.853 (6)
H272	0.2497	0.2876	0.6728	0.083*	0.853 (6)
C28A	0.3385 (5)	0.2149 (3)	0.7696 (3)	0.0578 (14)	0.853 (6)
H281	0.4202	0.2444	0.7759	0.069*	0.853 (6)
H282	0.3184	0.1940	0.8321	0.069*	0.853 (6)
C24B	0.217 (4)	0.128 (2)	0.650 (3)	0.0640 (14)	0.147 (6)
H243	0.2028	0.1556	0.5906	0.077*	0.147 (6)
H244	0.2195	0.0735	0.6355	0.077*	0.147 (6)
C25B	0.117 (3)	0.143 (2)	0.711 (3)	0.0714 (15)	0.147 (6)
H253	0.0360	0.1206	0.6835	0.086*	0.147 (6)
H254	0.1368	0.1154	0.7708	0.086*	0.147 (6)
O26B	0.097 (5)	0.195 (3)	0.728 (4)	0.093 (2)	0.147 (6)
C27B	0.215 (2)	0.2360 (18)	0.795 (2)	0.0690 (14)	0.147 (6)
H273	0.1920	0.2885	0.8100	0.083*	0.147 (6)
H274	0.2302	0.2082	0.8549	0.083*	0.147 (6)
C28B	0.333 (4)	0.233 (2)	0.735 (2)	0.0578 (14)	0.147 (6)
H283	0.4109	0.2495	0.7721	0.069*	0.147 (6)
H284	0.3206	0.2667	0.6805	0.069*	0.147 (6)
H8	0.945 (2)	0.2490 (16)	0.7983 (17)	0.056 (10)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Br1	0.0627 (2)	0.0822 (3)	0.0620 (2)	0.00876 (19)	0.01777 (17)	−0.02139 (19)
S1	0.0824 (7)	0.0747 (7)	0.0529 (5)	0.0012 (5)	−0.0187 (5)	0.0044 (5)
S2	0.0329 (4)	0.0586 (5)	0.0525 (4)	−0.0022 (4)	0.0058 (3)	−0.0169 (4)
O1	0.0833 (19)	0.094 (2)	0.104 (2)	0.0119 (17)	−0.0426 (16)	0.0176 (17)
O2	0.146 (3)	0.095 (2)	0.0411 (13)	−0.0125 (19)	−0.0076 (14)	−0.0056 (13)
C1	0.065 (2)	0.057 (2)	0.0509 (19)	0.0106 (18)	−0.0055 (16)	0.0103 (16)
C2	0.056 (2)	0.064 (2)	0.077 (2)	0.0132 (19)	−0.0008 (18)	−0.001 (2)
C3	0.071 (2)	0.054 (2)	0.086 (3)	0.014 (2)	−0.008 (2)	−0.0039 (19)
C4	0.070 (3)	0.069 (3)	0.086 (3)	0.002 (2)	−0.007 (2)	0.018 (2)
C5	0.071 (3)	0.107 (4)	0.093 (3)	−0.004 (3)	0.018 (2)	0.015 (3)
C6	0.091 (3)	0.086 (3)	0.066 (2)	0.003 (3)	0.014 (2)	−0.001 (2)
C7	0.092 (3)	0.094 (4)	0.150 (5)	−0.019 (3)	−0.017 (3)	0.018 (3)
N8	0.0513 (16)	0.0634 (19)	0.0523 (16)	0.0050 (14)	−0.0011 (13)	−0.0056 (14)
C9	0.0397 (16)	0.0506 (19)	0.0454 (17)	−0.0066 (14)	0.0055 (13)	−0.0053 (14)
C10	0.0342 (15)	0.0445 (18)	0.0461 (16)	−0.0066 (13)	0.0063 (12)	−0.0112 (13)
C11	0.0386 (16)	0.0492 (19)	0.0515 (17)	−0.0026 (14)	−0.0006 (13)	−0.0106 (14)
C12	0.0408 (17)	0.0457 (19)	0.067 (2)	−0.0020 (15)	0.0113 (15)	−0.0096 (16)
C13	0.060 (2)	0.054 (2)	0.060 (2)	−0.0027 (18)	0.0227 (17)	−0.0143 (17)
C14	0.068 (2)	0.058 (2)	0.0398 (16)	−0.0088 (18)	0.0082 (15)	−0.0064 (15)
O15	0.0602 (14)	0.0639 (16)	0.0861 (18)	0.0172 (13)	0.0062 (13)	−0.0164 (13)
C16	0.078 (3)	0.088 (3)	0.108 (3)	0.036 (2)	−0.021 (2)	−0.021 (3)
C17	0.0350 (15)	0.0425 (17)	0.0371 (15)	0.0052 (13)	−0.0036 (12)	−0.0042 (13)
N18	0.0323 (12)	0.0437 (14)	0.0435 (13)	0.0020 (11)	−0.0002 (10)	−0.0055 (11)
C19	0.0349 (15)	0.0416 (17)	0.0540 (17)	0.0031 (14)	−0.0006 (13)	−0.0026 (14)
N20	0.0505 (16)	0.0478 (16)	0.0780 (19)	−0.0068 (13)	0.0068 (14)	−0.0197 (14)
C21	0.063 (2)	0.050 (2)	0.069 (2)	−0.0033 (18)	0.0038 (17)	−0.0260 (17)
C22	0.0452 (17)	0.0495 (19)	0.0466 (17)	0.0032 (15)	0.0032 (13)	−0.0120 (14)
N23	0.0362 (13)	0.0539 (17)	0.0735 (18)	−0.0021 (13)	0.0045 (12)	−0.0110 (14)
C24A	0.047 (2)	0.064 (4)	0.081 (4)	−0.014 (2)	0.002 (3)	0.004 (3)
C25A	0.040 (2)	0.105 (4)	0.069 (3)	0.007 (2)	−0.007 (2)	−0.031 (3)
O26A	0.0384 (19)	0.119 (5)	0.120 (3)	0.016 (4)	−0.0075 (17)	−0.068 (5)
C27A	0.063 (3)	0.090 (4)	0.054 (3)	0.020 (2)	−0.004 (2)	−0.030 (3)
C28A	0.0385 (18)	0.088 (4)	0.047 (3)	0.003 (2)	0.004 (2)	−0.009 (3)
C24B	0.047 (2)	0.064 (4)	0.081 (4)	−0.014 (2)	0.002 (3)	0.004 (3)
C25B	0.040 (2)	0.105 (4)	0.069 (3)	0.007 (2)	−0.007 (2)	−0.031 (3)
O26B	0.0384 (19)	0.119 (5)	0.120 (3)	0.016 (4)	−0.0075 (17)	−0.068 (5)
C27B	0.063 (3)	0.090 (4)	0.054 (3)	0.020 (2)	−0.004 (2)	−0.030 (3)
C28B	0.0385 (18)	0.088 (4)	0.047 (3)	0.003 (2)	0.004 (2)	−0.009 (3)

Geometric parameters (Å, º) top

Br1—C22	1.894 (3)	C17—N18	1.321 (3)
S1—O2	1.428 (3)	C17—C22	1.388 (4)
S1—O1	1.428 (3)	N18—C19	1.344 (3)
S1—N8	1.632 (3)	C19—N20	1.343 (4)
S1—C1	1.762 (4)	C19—N23	1.351 (3)
S2—C17	1.759 (3)	N20—C21	1.330 (4)
S2—C10	1.774 (3)	C21—C22	1.359 (4)
C1—C6	1.370 (5)	C21—H21	0.9300
C1—C2	1.382 (5)	N23—C24A	1.448 (6)
C2—C3	1.372 (5)	N23—C28A	1.464 (6)
C2—H2	0.9300	N23—C28B	1.49 (4)
C3—C4	1.373 (5)	N23—C24B	1.58 (4)
C3—H3	0.9300	C24A—C25A	1.508 (8)
C4—C5	1.372 (6)	C24A—H241	0.9700
C4—C7	1.509 (5)	C24A—H242	0.9700
C5—C6	1.380 (6)	C25A—O26A	1.480 (8)
C5—H5	0.9300	C25A—H251	0.9700
C6—H6	0.9300	C25A—H252	0.9700
C7—H71	0.9600	O26A—C27A	1.392 (8)
C7—H72	0.9600	C27A—C28A	1.502 (7)
C7—H73	0.9600	C27A—H271	0.9700
N8—C9	1.421 (4)	C27A—H272	0.9700
N8—H8	0.850 (10)	C28A—H281	0.9700
C9—C10	1.389 (4)	C28A—H282	0.9700
C9—C14	1.392 (4)	C24B—C25B	1.36 (5)
C10—C11	1.385 (4)	C24B—H243	0.9700
C11—C12	1.379 (4)	C24B—H244	0.9700
C11—H11	0.9300	C25B—O26B	0.97 (4)
C12—O15	1.369 (4)	C25B—H253	0.9700
C12—C13	1.381 (4)	C25B—H254	0.9700
C13—C14	1.373 (4)	O26B—C27B	1.65 (5)
C13—H13	0.9300	C27B—C28B	1.47 (4)
C14—H14	0.9300	C27B—H273	0.9700
O15—C16	1.424 (4)	C27B—H274	0.9700
C16—H161	0.9600	C28B—H283	0.9700
C16—H162	0.9600	C28B—H284	0.9700
C16—H163	0.9600

O2—S1—O1	120.06 (17)	C21—N20—C19	115.3 (3)
O2—S1—N8	108.00 (16)	N20—C21—C22	123.5 (3)
O1—S1—N8	105.63 (16)	N20—C21—H21	118.3
O2—S1—C1	106.56 (18)	C22—C21—H21	118.3
O1—S1—C1	108.22 (17)	C21—C22—C17	117.3 (3)
N8—S1—C1	107.88 (14)	C21—C22—Br1	120.4 (2)
C17—S2—C10	100.27 (12)	C17—C22—Br1	122.3 (2)
C6—C1—C2	119.3 (4)	C19—N23—C24A	123.2 (3)
C6—C1—S1	120.9 (3)	C19—N23—C28A	123.1 (3)
C2—C1—S1	119.7 (3)	C24A—N23—C28A	112.9 (4)
C3—C2—C1	120.1 (3)	C19—N23—C28B	113.6 (14)
C3—C2—H2	120.0	C24A—N23—C28B	114.9 (14)
C1—C2—H2	120.0	C19—N23—C24B	115.9 (16)
C2—C3—C4	121.4 (4)	C28A—N23—C24B	112.5 (17)
C2—C3—H3	119.3	C28B—N23—C24B	106 (2)
C4—C3—H3	119.3	N23—C24A—C25A	109.0 (4)
C5—C4—C3	117.6 (4)	N23—C24A—H241	109.9
C5—C4—C7	122.1 (4)	C25A—C24A—H241	109.9
C3—C4—C7	120.2 (4)	N23—C24A—H242	109.9
C4—C5—C6	122.0 (4)	C25A—C24A—H242	109.9
C4—C5—H5	119.0	H241—C24A—H242	108.3
C6—C5—H5	119.0	O26A—C25A—C24A	110.4 (5)
C1—C6—C5	119.4 (4)	O26A—C25A—H251	109.6
C1—C6—H6	120.3	C24A—C25A—H251	109.6
C5—C6—H6	120.3	O26A—C25A—H252	109.6
C4—C7—H71	109.5	C24A—C25A—H252	109.6
C4—C7—H72	109.5	H251—C25A—H252	108.1
H71—C7—H72	109.5	C27A—O26A—C25A	110.7 (6)
C4—C7—H73	109.5	O26A—C27A—C28A	112.2 (5)
H71—C7—H73	109.5	O26A—C27A—H271	109.2
H72—C7—H73	109.5	C28A—C27A—H271	109.2
C9—N8—S1	122.1 (2)	O26A—C27A—H272	109.2
C9—N8—H8	119 (2)	C28A—C27A—H272	109.2
S1—N8—H8	108 (2)	H271—C27A—H272	107.9
C10—C9—C14	117.8 (3)	N23—C28A—C27A	107.8 (4)
C10—C9—N8	121.8 (3)	N23—C28A—H281	110.1
C14—C9—N8	120.4 (3)	C27A—C28A—H281	110.1
C11—C10—C9	121.2 (3)	N23—C28A—H282	110.1
C11—C10—S2	118.0 (2)	C27A—C28A—H282	110.1
C9—C10—S2	120.8 (2)	H281—C28A—H282	108.5
C12—C11—C10	120.0 (3)	C25B—C24B—N23	109 (3)
C12—C11—H11	120.0	C25B—C24B—H243	109.9
C10—C11—H11	120.0	N23—C24B—H243	109.9
O15—C12—C11	124.1 (3)	C25B—C24B—H244	109.9
O15—C12—C13	116.3 (3)	N23—C24B—H244	109.9
C11—C12—C13	119.5 (3)	H243—C24B—H244	108.3
C14—C13—C12	120.4 (3)	O26B—C25B—C24B	119 (5)
C14—C13—H13	119.8	O26B—C25B—H253	107.5
C12—C13—H13	119.8	C24B—C25B—H253	107.5
C13—C14—C9	121.2 (3)	O26B—C25B—H254	107.5
C13—C14—H14	119.4	C24B—C25B—H254	107.5
C9—C14—H14	119.4	H253—C25B—H254	107.0
C12—O15—C16	117.0 (3)	C25B—O26B—C27B	114 (5)
O15—C16—H161	109.5	C28B—C27B—O26B	104 (3)
O15—C16—H162	109.5	C28B—C27B—H273	111.0
H161—C16—H162	109.5	O26B—C27B—H273	111.0
O15—C16—H163	109.5	C28B—C27B—H274	111.0
H161—C16—H163	109.5	O26B—C27B—H274	111.0
H162—C16—H163	109.5	H273—C27B—H274	109.0
N18—C17—C22	121.1 (3)	C27B—C28B—N23	111 (3)
N18—C17—S2	119.5 (2)	C27B—C28B—H283	109.5
C22—C17—S2	119.4 (2)	N23—C28B—H283	109.5
C17—N18—C19	117.3 (2)	C27B—C28B—H284	109.5
N20—C19—N18	125.4 (3)	N23—C28B—H284	109.5
N20—C19—N23	117.8 (3)	H283—C28B—H284	108.1
N18—C19—N23	116.8 (3)

O2—S1—C1—C6	4.6 (3)	C17—N18—C19—N23	179.8 (3)
O1—S1—C1—C6	135.0 (3)	N18—C19—N20—C21	−1.1 (5)
N8—S1—C1—C6	−111.2 (3)	N23—C19—N20—C21	−179.3 (3)
O2—S1—C1—C2	−173.2 (3)	C19—N20—C21—C22	0.1 (5)
O1—S1—C1—C2	−42.8 (3)	N20—C21—C22—C17	0.3 (5)
N8—S1—C1—C2	71.1 (3)	N20—C21—C22—Br1	179.6 (3)
C6—C1—C2—C3	−0.8 (5)	N18—C17—C22—C21	0.1 (4)
S1—C1—C2—C3	177.0 (3)	S2—C17—C22—C21	−179.9 (2)
C1—C2—C3—C4	−1.2 (5)	N18—C17—C22—Br1	−179.1 (2)
C2—C3—C4—C5	2.1 (6)	S2—C17—C22—Br1	0.8 (3)
C2—C3—C4—C7	−177.5 (4)	N20—C19—N23—C24A	−7.8 (5)
C3—C4—C5—C6	−1.1 (6)	N18—C19—N23—C24A	173.8 (3)
C7—C4—C5—C6	178.5 (4)	N20—C19—N23—C28A	−177.4 (3)
C2—C1—C6—C5	1.8 (6)	N18—C19—N23—C28A	4.2 (5)
S1—C1—C6—C5	−176.0 (3)	N20—C19—N23—C28B	−154.3 (14)
C4—C5—C6—C1	−0.8 (6)	N18—C19—N23—C28B	27.2 (15)
O2—S1—N8—C9	−55.5 (3)	N20—C19—N23—C24B	−31.8 (17)
O1—S1—N8—C9	174.9 (2)	N18—C19—N23—C24B	149.8 (16)
C1—S1—N8—C9	59.3 (3)	C19—N23—C24A—C25A	−113.5 (5)
S1—N8—C9—C10	−120.3 (3)	C28A—N23—C24A—C25A	57.0 (6)
S1—N8—C9—C14	61.8 (4)	C28B—N23—C24A—C25A	32.7 (16)
C14—C9—C10—C11	−0.3 (4)	C24B—N23—C24A—C25A	−37 (5)
N8—C9—C10—C11	−178.3 (3)	N23—C24A—C25A—O26A	−55.1 (7)
C14—C9—C10—S2	177.9 (2)	C24A—C25A—O26A—C27A	57.5 (8)
N8—C9—C10—S2	−0.1 (4)	C25A—O26A—C27A—C28A	−59.4 (8)
C17—S2—C10—C11	−70.7 (2)	C19—N23—C28A—C27A	113.4 (4)
C17—S2—C10—C9	111.1 (2)	C24A—N23—C28A—C27A	−57.2 (6)
C9—C10—C11—C12	−2.0 (4)	C28B—N23—C28A—C27A	43 (4)
S2—C10—C11—C12	179.9 (2)	C24B—N23—C28A—C27A	−33.3 (16)
C10—C11—C12—O15	179.7 (3)	O26A—C27A—C28A—N23	58.2 (6)
C10—C11—C12—C13	2.2 (4)	C19—N23—C24B—C25B	−177 (2)
O15—C12—C13—C14	−178.0 (3)	C24A—N23—C24B—C25B	68 (4)
C11—C12—C13—C14	−0.2 (5)	C28A—N23—C24B—C25B	−27 (3)
C12—C13—C14—C9	−2.0 (5)	C28B—N23—C24B—C25B	−50 (4)
C10—C9—C14—C13	2.3 (4)	N23—C24B—C25B—O26B	65 (7)
N8—C9—C14—C13	−179.7 (3)	C24B—C25B—O26B—C27B	−69 (7)
C11—C12—O15—C16	−3.6 (5)	C25B—O26B—C27B—C28B	60 (7)
C13—C12—O15—C16	174.1 (3)	O26B—C27B—C28B—N23	−52 (4)
C10—S2—C17—N18	−3.3 (3)	C19—N23—C28B—C27B	−178.5 (19)
C10—S2—C17—C22	176.7 (2)	C24A—N23—C28B—C27B	32 (3)
C22—C17—N18—C19	−0.9 (4)	C28A—N23—C28B—C27B	−58 (3)
S2—C17—N18—C19	179.1 (2)	C24B—N23—C28B—C27B	53 (3)
C17—N18—C19—N20	1.5 (4)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O26Aⁱ	0.85 (2)	2.02 (2)	2.846 (8)	163 (2)
N8—H8···O26Bⁱ	0.85 (2)	2.06 (6)	2.895 (5)	165 (3)
C21—H21···N20ⁱⁱ	0.93	2.53	3.394 (4)	155
C25A—H251···O2ⁱⁱⁱ	0.97	2.59	3.377 (6)	138
C27A—H272···O2ⁱⁱⁱ	0.97	2.52	3.341 (6)	143

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x−1/2, −y+1/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₂₂H₂₃BrN₄O₄S₂
M_r	551.47
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.0321 (3), 17.4842 (6), 13.9095 (4)
β (°)	91.699 (3)
V (Å³)	2438.70 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	1.89
Crystal size (mm)	0.3 × 0.2 × 0.1

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)
T_min, T_max	0.557, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	21500, 4783, 3361
R_int	0.040
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.041, 0.086, 1.01
No. of reflections	4783
No. of parameters	321
No. of restraints	1
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.53, −0.46

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
N8—H8···O26Aⁱ	0.85 (2)	2.02 (2)	2.846 (8)	163 (2)
N8—H8···O26Bⁱ	0.85 (2)	2.06 (6)	2.895 (5)	165 (3)
C21—H21···N20ⁱⁱ	0.93	2.53	3.394 (4)	155
C25A—H251···O2ⁱⁱⁱ	0.97	2.59	3.377 (6)	138
C27A—H272···O2ⁱⁱⁱ	0.97	2.52	3.341 (6)	143

Symmetry codes: (i) x+1, y, z; (ii) −x+1, −y, −z+1; (iii) x−1/2, −y+1/2, z−1/2.

Acknowledgements

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. CSD 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
Gao, J. & Pederson, J. A. (2005). Environ. Sci. Technol. 39, 9509–9516. Web of Science CrossRef PubMed CAS 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 8| August 2012| Pages o2590-o2591

https://doi.org/10.1107/S1600536812033375

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

N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan­yl}-4-meth­­oxy­phen­yl)-4-methyl­benzene­sulfonamide

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Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)-4-methylbenzenesulfonamide