N-(2-{[5-Bromo-2-(morpholin-4-yl)pyrimidin-4-yl]sulfan-yl}-4-meth-oxy-phen-yl)-4-chloro-benzene-sulfonamide.

In the title compound, C(21)H(20)BrClN(4)O(4)S(2), 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 mol-ecular conformation is stabilized by a weak intra-molecular π-π stacking inter-action between the pyrimidine and the 4-chloro-benzene rings [centroid-centroid distance = 3.978 (2) Å]. The morpholine ring adopts a chair conformation. In the crystal, mol-ecules 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 = 571.89

Monoclinic,

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 ▶) 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[F 2 > 2σ(F 2)] = 0.045

wR(F 2) = 0.117

S = 1.03

4744 reflections

299 parameters

H-atom parameters constrained

Δρmax = 0.42 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 ▶); cell refinement: CrysAlis PRO; 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 ▶).

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812036689/is5183sup1.cif

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

Supplementary material file. DOI: 10.1107/S1600536812036689/is5183Isup3.cml

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C21H20BrClN4O4S2	F(000) = 1160
Mr = 571.89	Dx = 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

Oxford Diffraction Xcalibur Sapphire3 diffractometer	4744 independent reflections
Radiation source: fine-focus sealed tube	3408 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.048
Detector resolution: 16.1049 pixels mm-1	θmax = 26.0°, θmin = 3.7°
w scans	h = −12→12
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −21→21
Tmin = 0.438, Tmax = 0.668	l = −17→17
26979 measured reflections

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(Fo2) + (0.0505P)2 + 1.7709P] where P = (Fo2 + 2Fc2)/3
4744 reflections	(Δ/σ)max = 0.001
299 parameters	Δρmax = 0.42 e Å−3
0 restraints	Δρmin = −0.65 e Å−3

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.

	x	y	z	Uiso*/Ueq
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*

	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)

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)

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

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) ; (ii) .