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

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

doi:10.1107/S1600536812036689

organic compounds

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ISSN: 2056-9890

Volume 68| Part 9| September 2012| Page o2800

doi:10.1107/S1600536812036689

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

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 22 August 2012; accepted 23 August 2012; online 31 August 2012)

In the title compound, C₂₁H₂₀BrClN₄O₄S₂, the benzene rings bridged by the sulfonamide group are tilted relative to each other by a dihedral angle of 70.2 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 69.5 (1)°. The molecular conformation is stabilized by a weak intramolecular π–π stacking interaction between the pyrimidine and the 4-chlorobenzene rings [centroid–centroid distance = 3.978 (2) Å]. The morpholine ring adopts a chair conformation. In the crystal, molecules are linked into inversion dimers by pairs of C—H⋯N hydrogen bonds and these dimers are further connected by N—H⋯O hydrogen bonds, forming a tape along the a 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

C₂₁H₂₀BrClN₄O₄S₂
M_r = 571.89
Monoclinic, P 2₁ /n
a = 10.0311 (3) Å
b = 17.3096 (6) Å
c = 13.9223 (4) Å
β = 91.829 (3)°
V = 2416.16 (13) Å³
Z = 4
Mo Kα radiation
μ = 2.02 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 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.438, T_max = 0.668
26979 measured reflections
4744 independent reflections
3408 reflections with I > 2σ(I)
R_int = 0.048

Refinement

R[F² > 2σ(F²)] = 0.045
wR(F²) = 0.117
S = 1.03
4744 reflections
299 parameters
H-atom parameters constrained
Δρ_max = 0.42 e Å⁻³
Δρ_min = −0.65 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N7—H7⋯O25ⁱ	0.86	2.09	2.849 (4)	148
C20—H20⋯N19ⁱⁱ	0.93	2.52	3.352 (5)	149
Symmetry codes: (i) x-1, y, z; (ii) -x+2, -y, -z+1.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis PRO; data reduction: CrysAlis RED (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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/S1600536812036689/is5183sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536812036689/is5183Isup2.hkl

Supporting information file. DOI: 10.1107/S1600536812036689/is5183Isup3.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 atom S1 with a C1—S1—N7—C8 torsion angle of 60.8 (3)°. The morpholine ring is exhibiting a chair conformation [asymmetry parameters are: ΔC2(N22—C23) = 2.53; ΔCs(N22—O25) = 1/5; Duax & Norton, 1975]. The two benzene rings (C1—C6/C8—C13) are tilted relative to each other by 70.2 (1)° and the dihedral angle between the sulfur bridged pyrimidine and benzene rings is 69.5 (1)°. The molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 4-chloro benzene rings [centroid–centroid distance = 3.978 (2) Å, interplanar spacing = 3.340 Å, and centroid shift = 2.16 Å]. In the crystal, molecules are linked into dimers by pairs of C20—H20···N19 hydrogen bonds and these dimers are further linked by N7—H7···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-chloro-pyrimidin-4-ylsulfanyl)-4-methoxy-phenyl]-4-chloro-benzenesulfonamide (5.22 g, 0.01 mol) with morpholine (0.88 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 80%, m.p. 462–464 K)

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell refinement: CrysAlis PRO (Oxford Diffraction, 2010); data reduction: CrysAlis RED (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 title 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. 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-chlorobenzenesulfonamide top

Crystal data top

C₂₁H₂₀BrClN₄O₄S₂	F(000) = 1160
M_r = 571.89	D_x = 1.572 Mg m⁻³
Monoclinic, P2₁/n	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 9194 reflections
a = 10.0311 (3) Å	θ = 3.5–29.0°
b = 17.3096 (6) Å	µ = 2.02 mm⁻¹
c = 13.9223 (4) Å	T = 293 K
β = 91.829 (3)°	Block, white
V = 2416.16 (13) Å³	0.3 × 0.2 × 0.2 mm
Z = 4

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4744 independent reflections
Radiation source: fine-focus sealed tube	3408 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.048
Detector resolution: 16.1049 pixels mm^-1	θ_max = 26.0°, θ_min = 3.7°
w scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
T_min = 0.438, T_max = 0.668	l = −17→17
26979 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)] = 0.045	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0505P)² + 1.7709P] where P = (F_o² + 2F_c²)/3
4744 reflections	(Δ/σ)_max = 0.001
299 parameters	Δρ_max = 0.42 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₂₁H₂₀BrClN₄O₄S₂	V = 2416.16 (13) Å³
M_r = 571.89	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 10.0311 (3) Å	µ = 2.02 mm⁻¹
b = 17.3096 (6) Å	T = 293 K
c = 13.9223 (4) Å	0.3 × 0.2 × 0.2 mm
β = 91.829 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4744 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	3408 reflections with I > 2σ(I)
T_min = 0.438, T_max = 0.668	R_int = 0.048
26979 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.045	0 restraints
wR(F²) = 0.117	H-atom parameters constrained
S = 1.03	Δρ_max = 0.42 e Å⁻³
4744 reflections	Δρ_min = −0.65 e Å⁻³
299 parameters

Special details top

Experimental. Absorption correction: 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
O1	0.5036 (3)	0.16095 (19)	0.0690 (2)	0.0825 (9)
O2	0.6714 (4)	0.24236 (18)	−0.00871 (19)	0.0816 (9)
Br1	0.66487 (4)	0.12100 (3)	0.53546 (3)	0.06449 (16)
S2	0.69475 (8)	0.25466 (5)	0.37229 (6)	0.0451 (2)
S1	0.62576 (11)	0.20307 (6)	0.07413 (7)	0.0605 (3)
Cl1	1.06308 (15)	−0.03829 (9)	0.18890 (14)	0.1136 (5)
C1	0.7553 (4)	0.1383 (2)	0.1103 (3)	0.0516 (9)
C2	0.8716 (5)	0.1366 (3)	0.0617 (3)	0.0750 (12)
H2	0.8858	0.1717	0.0125	0.090*
C3	0.9679 (5)	0.0824 (3)	0.0860 (4)	0.0851 (14)
H3	1.0470	0.0803	0.0531	0.102*
C4	0.9451 (4)	0.0318 (3)	0.1593 (4)	0.0711 (12)
C5	0.8317 (4)	0.0349 (2)	0.2101 (3)	0.0647 (11)
H5	0.8197	0.0012	0.2611	0.078*
C6	0.7347 (4)	0.0882 (2)	0.1854 (3)	0.0582 (10)
H6	0.6561	0.0903	0.2190	0.070*
N7	0.6095 (3)	0.26564 (17)	0.1598 (2)	0.0492 (7)
H7	0.5343	0.2686	0.1876	0.059*
C8	0.7152 (3)	0.31610 (19)	0.1908 (2)	0.0405 (7)
C9	0.7703 (4)	0.3677 (2)	0.1266 (3)	0.0503 (9)
H9	0.7367	0.3699	0.0636	0.060*
C10	0.8737 (4)	0.4154 (2)	0.1548 (3)	0.0509 (9)
H10	0.9106	0.4487	0.1105	0.061*
C11	0.9235 (3)	0.41437 (19)	0.2487 (3)	0.0461 (8)
C12	0.8665 (3)	0.36557 (19)	0.3139 (2)	0.0431 (8)
H12	0.8964	0.3659	0.3779	0.052*
C13	0.7647 (3)	0.31593 (18)	0.2847 (2)	0.0382 (7)
O14	1.0244 (3)	0.46473 (15)	0.2706 (2)	0.0633 (7)
C15	1.0716 (5)	0.4676 (3)	0.3673 (4)	0.0833 (14)
H15A	0.9983	0.4774	0.4083	0.125*
H15B	1.1362	0.5083	0.3748	0.125*
H15C	1.1123	0.4191	0.3845	0.125*
C16	0.8284 (3)	0.18979 (17)	0.3927 (2)	0.0365 (7)
N17	0.9356 (2)	0.19637 (14)	0.33991 (18)	0.0367 (6)
C18	1.0363 (3)	0.14619 (18)	0.3584 (2)	0.0412 (8)
N19	1.0348 (3)	0.08998 (17)	0.4253 (2)	0.0555 (8)
C20	0.9257 (4)	0.0853 (2)	0.4755 (3)	0.0574 (10)
H20	0.9215	0.0474	0.5227	0.069*
C21	0.8188 (3)	0.13305 (19)	0.4616 (2)	0.0424 (8)
N22	1.1446 (3)	0.15306 (17)	0.3042 (2)	0.0521 (7)
C23	1.2648 (4)	0.1067 (3)	0.3206 (4)	0.0713 (12)
H23A	1.2512	0.0708	0.3729	0.086*
H23B	1.2824	0.0769	0.2634	0.086*
C24	1.3790 (4)	0.1560 (3)	0.3443 (4)	0.0766 (13)
H24A	1.3669	0.1796	0.4066	0.092*
H24B	1.4591	0.1246	0.3486	0.092*
O25	1.3958 (3)	0.2151 (2)	0.2743 (2)	0.0899 (11)
C26	1.2790 (4)	0.2613 (3)	0.2621 (4)	0.0846 (15)
H26A	1.2934	0.2995	0.2125	0.101*
H26B	1.2632	0.2886	0.3215	0.101*
C27	1.1609 (4)	0.2154 (3)	0.2354 (3)	0.0649 (11)
H27A	1.0824	0.2482	0.2343	0.078*
H27B	1.1704	0.1940	0.1716	0.078*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
O1	0.0727 (19)	0.083 (2)	0.089 (2)	−0.0082 (16)	−0.0313 (16)	−0.0141 (18)
O2	0.127 (3)	0.079 (2)	0.0388 (15)	0.0099 (19)	−0.0027 (15)	0.0047 (14)
Br1	0.0599 (3)	0.0763 (3)	0.0583 (3)	−0.0100 (2)	0.01681 (19)	0.0202 (2)
S2	0.0322 (4)	0.0552 (5)	0.0482 (5)	0.0007 (4)	0.0061 (3)	0.0165 (4)
S1	0.0729 (7)	0.0615 (6)	0.0461 (5)	−0.0010 (5)	−0.0126 (5)	−0.0021 (5)
Cl1	0.0878 (9)	0.0894 (10)	0.1623 (15)	0.0286 (8)	−0.0144 (9)	−0.0113 (9)
C1	0.058 (2)	0.049 (2)	0.048 (2)	−0.0077 (17)	−0.0057 (17)	−0.0081 (17)
C2	0.082 (3)	0.076 (3)	0.068 (3)	−0.001 (3)	0.018 (2)	0.006 (2)
C3	0.069 (3)	0.091 (4)	0.096 (4)	0.000 (3)	0.018 (3)	−0.014 (3)
C4	0.064 (3)	0.058 (3)	0.091 (3)	0.003 (2)	−0.006 (2)	−0.014 (2)
C5	0.064 (3)	0.048 (2)	0.082 (3)	−0.010 (2)	−0.007 (2)	0.005 (2)
C6	0.057 (2)	0.054 (2)	0.063 (2)	−0.0094 (19)	−0.0005 (19)	0.001 (2)
N7	0.0450 (16)	0.0564 (18)	0.0462 (16)	−0.0007 (14)	−0.0001 (13)	0.0004 (14)
C8	0.0393 (17)	0.0421 (19)	0.0405 (18)	0.0066 (14)	0.0061 (14)	0.0035 (14)
C9	0.063 (2)	0.052 (2)	0.0365 (18)	0.0063 (18)	0.0070 (16)	0.0057 (16)
C10	0.057 (2)	0.045 (2)	0.052 (2)	0.0012 (17)	0.0192 (17)	0.0131 (17)
C11	0.0397 (18)	0.0387 (19)	0.060 (2)	0.0016 (15)	0.0103 (16)	0.0091 (16)
C12	0.0398 (17)	0.044 (2)	0.0454 (19)	0.0028 (15)	−0.0019 (15)	0.0102 (15)
C13	0.0346 (16)	0.0376 (17)	0.0426 (18)	0.0048 (13)	0.0061 (14)	0.0103 (14)
O14	0.0573 (15)	0.0597 (16)	0.0730 (19)	−0.0169 (13)	0.0053 (14)	0.0132 (14)
C15	0.073 (3)	0.086 (3)	0.089 (3)	−0.032 (3)	−0.016 (3)	0.017 (3)
C16	0.0339 (16)	0.0369 (17)	0.0384 (17)	−0.0049 (13)	−0.0027 (13)	0.0033 (14)
N17	0.0300 (13)	0.0380 (15)	0.0420 (15)	−0.0040 (11)	−0.0004 (11)	0.0057 (12)
C18	0.0352 (17)	0.0381 (18)	0.050 (2)	−0.0063 (14)	−0.0007 (15)	0.0013 (15)
N19	0.0500 (17)	0.0424 (17)	0.074 (2)	0.0040 (14)	0.0052 (16)	0.0190 (15)
C20	0.060 (2)	0.047 (2)	0.065 (2)	−0.0005 (18)	0.0028 (19)	0.0229 (19)
C21	0.0440 (18)	0.0411 (19)	0.0425 (19)	−0.0075 (15)	0.0064 (15)	0.0137 (15)
N22	0.0364 (15)	0.0505 (18)	0.070 (2)	0.0009 (13)	0.0085 (14)	0.0098 (16)
C23	0.048 (2)	0.067 (3)	0.099 (3)	0.015 (2)	0.013 (2)	0.000 (2)
C24	0.042 (2)	0.092 (3)	0.095 (3)	−0.005 (2)	−0.006 (2)	0.032 (3)
O25	0.0371 (14)	0.136 (3)	0.096 (2)	−0.0163 (16)	−0.0023 (14)	0.056 (2)
C26	0.064 (3)	0.101 (4)	0.088 (3)	−0.025 (3)	−0.010 (2)	0.043 (3)
C27	0.040 (2)	0.095 (3)	0.060 (2)	−0.003 (2)	0.0070 (17)	0.017 (2)

Geometric parameters (Å, º) top

O1—S1	1.426 (3)	C12—C13	1.386 (4)
O2—S1	1.427 (3)	C12—H12	0.9300
Br1—C21	1.894 (3)	O14—C15	1.414 (5)
S2—C16	1.765 (3)	C15—H15A	0.9600
S2—C13	1.777 (3)	C15—H15B	0.9600
S1—N7	1.623 (3)	C15—H15C	0.9600
S1—C1	1.777 (4)	C16—N17	1.326 (4)
Cl1—C4	1.736 (5)	C16—C21	1.379 (4)
C1—C2	1.367 (6)	N17—C18	1.351 (4)
C1—C6	1.379 (5)	C18—N19	1.347 (4)
C2—C3	1.381 (7)	C18—N22	1.348 (4)
C2—H2	0.9300	N19—C20	1.320 (5)
C3—C4	1.368 (7)	C20—C21	1.363 (5)
C3—H3	0.9300	C20—H20	0.9300
C4—C5	1.360 (6)	N22—C27	1.455 (5)
C5—C6	1.376 (6)	N22—C23	1.461 (5)
C5—H5	0.9300	C23—C24	1.458 (6)
C6—H6	0.9300	C23—H23A	0.9700
N7—C8	1.430 (4)	C23—H23B	0.9700
N7—H7	0.8600	C24—O25	1.426 (5)
C8—C13	1.384 (4)	C24—H24A	0.9700
C8—C9	1.391 (5)	C24—H24B	0.9700
C9—C10	1.374 (5)	O25—C26	1.424 (5)
C9—H9	0.9300	C26—C27	1.465 (6)
C10—C11	1.384 (5)	C26—H26A	0.9700
C10—H10	0.9300	C26—H26B	0.9700
C11—O14	1.363 (4)	C27—H27A	0.9700
C11—C12	1.378 (4)	C27—H27B	0.9700

C16—S2—C13	100.11 (14)	O14—C15—H15B	109.5
O1—S1—O2	120.05 (19)	H15A—C15—H15B	109.5
O1—S1—N7	105.76 (18)	O14—C15—H15C	109.5
O2—S1—N7	108.56 (17)	H15A—C15—H15C	109.5
O1—S1—C1	108.13 (18)	H15B—C15—H15C	109.5
O2—S1—C1	106.19 (19)	N17—C16—C21	121.5 (3)
N7—S1—C1	107.62 (16)	N17—C16—S2	118.8 (2)
C2—C1—C6	120.8 (4)	C21—C16—S2	119.7 (2)
C2—C1—S1	120.1 (3)	C16—N17—C18	117.0 (3)
C6—C1—S1	119.1 (3)	N19—C18—N22	118.5 (3)
C1—C2—C3	119.6 (4)	N19—C18—N17	124.9 (3)
C1—C2—H2	120.2	N22—C18—N17	116.6 (3)
C3—C2—H2	120.2	C20—N19—C18	116.0 (3)
C4—C3—C2	119.0 (4)	N19—C20—C21	123.3 (3)
C4—C3—H3	120.5	N19—C20—H20	118.3
C2—C3—H3	120.5	C21—C20—H20	118.3
C5—C4—C3	121.7 (4)	C20—C21—C16	117.3 (3)
C5—C4—Cl1	118.6 (4)	C20—C21—Br1	120.5 (2)
C3—C4—Cl1	119.7 (4)	C16—C21—Br1	122.2 (2)
C4—C5—C6	119.6 (4)	C18—N22—C27	122.9 (3)
C4—C5—H5	120.2	C18—N22—C23	122.7 (3)
C6—C5—H5	120.2	C27—N22—C23	113.7 (3)
C5—C6—C1	119.3 (4)	C24—C23—N22	110.6 (4)
C5—C6—H6	120.4	C24—C23—H23A	109.5
C1—C6—H6	120.4	N22—C23—H23A	109.5
C8—N7—S1	122.6 (2)	C24—C23—H23B	109.5
C8—N7—H7	118.7	N22—C23—H23B	109.5
S1—N7—H7	118.7	H23A—C23—H23B	108.1
C13—C8—C9	118.1 (3)	O25—C24—C23	112.0 (4)
C13—C8—N7	121.6 (3)	O25—C24—H24A	109.2
C9—C8—N7	120.3 (3)	C23—C24—H24A	109.2
C10—C9—C8	120.9 (3)	O25—C24—H24B	109.2
C10—C9—H9	119.5	C23—C24—H24B	109.2
C8—C9—H9	119.5	H24A—C24—H24B	107.9
C9—C10—C11	120.6 (3)	C26—O25—C24	111.7 (3)
C9—C10—H10	119.7	O25—C26—C27	112.4 (4)
C11—C10—H10	119.7	O25—C26—H26A	109.1
O14—C11—C12	124.5 (3)	C27—C26—H26A	109.1
O14—C11—C10	116.4 (3)	O25—C26—H26B	109.1
C12—C11—C10	119.0 (3)	C27—C26—H26B	109.1
C11—C12—C13	120.3 (3)	H26A—C26—H26B	107.8
C11—C12—H12	119.9	N22—C27—C26	110.0 (3)
C13—C12—H12	119.9	N22—C27—H27A	109.7
C8—C13—C12	121.0 (3)	C26—C27—H27A	109.7
C8—C13—S2	120.8 (2)	N22—C27—H27B	109.7
C12—C13—S2	118.1 (2)	C26—C27—H27B	109.7
C11—O14—C15	117.3 (3)	H27A—C27—H27B	108.2
O14—C15—H15A	109.5

O1—S1—C1—C2	132.3 (3)	C11—C12—C13—S2	−179.8 (2)
O2—S1—C1—C2	2.2 (4)	C16—S2—C13—C8	111.6 (3)
N7—S1—C1—C2	−113.9 (3)	C16—S2—C13—C12	−70.9 (3)
O1—S1—C1—C6	−45.3 (3)	C12—C11—O14—C15	−1.2 (5)
O2—S1—C1—C6	−175.4 (3)	C10—C11—O14—C15	176.6 (4)
N7—S1—C1—C6	68.5 (3)	C13—S2—C16—N17	−4.3 (3)
C6—C1—C2—C3	2.1 (6)	C13—S2—C16—C21	176.6 (3)
S1—C1—C2—C3	−175.5 (4)	C21—C16—N17—C18	−1.6 (4)
C1—C2—C3—C4	−0.6 (7)	S2—C16—N17—C18	179.3 (2)
C2—C3—C4—C5	−1.6 (7)	C16—N17—C18—N19	0.8 (5)
C2—C3—C4—Cl1	178.4 (4)	C16—N17—C18—N22	179.7 (3)
C3—C4—C5—C6	2.4 (7)	N22—C18—N19—C20	−179.2 (3)
Cl1—C4—C5—C6	−177.6 (3)	N17—C18—N19—C20	−0.3 (5)
C4—C5—C6—C1	−0.9 (6)	C18—N19—C20—C21	0.6 (6)
C2—C1—C6—C5	−1.3 (6)	N19—C20—C21—C16	−1.4 (6)
S1—C1—C6—C5	176.3 (3)	N19—C20—C21—Br1	178.9 (3)
O1—S1—N7—C8	176.2 (3)	N17—C16—C21—C20	1.9 (5)
O2—S1—N7—C8	−53.7 (3)	S2—C16—C21—C20	−179.0 (3)
C1—S1—N7—C8	60.8 (3)	N17—C16—C21—Br1	−178.3 (2)
S1—N7—C8—C13	−121.0 (3)	S2—C16—C21—Br1	0.8 (4)
S1—N7—C8—C9	59.7 (4)	N19—C18—N22—C27	−175.0 (3)
C13—C8—C9—C10	2.0 (5)	N17—C18—N22—C27	6.0 (5)
N7—C8—C9—C10	−178.7 (3)	N19—C18—N22—C23	−5.6 (5)
C8—C9—C10—C11	−1.4 (5)	N17—C18—N22—C23	175.4 (3)
C9—C10—C11—O14	−178.8 (3)	C18—N22—C23—C24	−118.5 (4)
C9—C10—C11—C12	−1.0 (5)	C27—N22—C23—C24	51.7 (5)
O14—C11—C12—C13	−179.6 (3)	N22—C23—C24—O25	−53.3 (5)
C10—C11—C12—C13	2.8 (5)	C23—C24—O25—C26	56.6 (6)
C9—C8—C13—C12	−0.2 (5)	C24—O25—C26—C27	−56.8 (5)
N7—C8—C13—C12	−179.5 (3)	C18—N22—C27—C26	118.8 (4)
C9—C8—C13—S2	177.3 (2)	C23—N22—C27—C26	−51.5 (5)
N7—C8—C13—S2	−2.0 (4)	O25—C26—C27—N22	53.5 (5)
C11—C12—C13—C8	−2.2 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N7—H7···O25ⁱ	0.86	2.09	2.849 (4)	148
C20—H20···N19ⁱⁱ	0.93	2.52	3.352 (5)	149

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

Experimental details

Crystal data
Chemical formula	C₂₁H₂₀BrClN₄O₄S₂
M_r	571.89
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	293
a, b, c (Å)	10.0311 (3), 17.3096 (6), 13.9223 (4)
β (°)	91.829 (3)
V (Å³)	2416.16 (13)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.02
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	0.438, 0.668
No. of measured, independent and observed [I > 2σ(I)] reflections	26979, 4744, 3408
R_int	0.048
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.045, 0.117, 1.03
No. of reflections	4744
No. of parameters	299
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.42, −0.65

Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), CrysAlis RED (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
N7—H7···O25ⁱ	0.86	2.09	2.849 (4)	148
C20—H20···N19ⁱⁱ	0.93	2.52	3.352 (5)	149

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

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
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 and CrysAlis RED. 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 o2800

doi:10.1107/S1600536812036689

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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-chloro­benzene­sulfonamide

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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-chlorobenzenesulfonamide