N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfan-yl}-4-meth-oxy-phen-yl)-4-methyl-benzene-sulfonamide.

In the title compound, C(23)H(25)BrN(4)O(3)S(2), the benzene rings bridged by the sulfonamide group are tilted relative to each other by 69.7 (1)° and the dihedral angle between the sulfur-bridged pyrimidine and benzene rings is 70.4 (1)°. The mol-ecular conformation is stabilized by a weak intra-molecular π-π stacking inter-action between the pyrimidine and the 4-methyl benzene rings [centroid-centroid distance = 3.633 (2) Å]. The piperidine ring adopts a chair conformation. In the crystal, mol-ecules are linked into inversion dimers by pairs of N-H⋯O hydrogen bonds.

Related literature

For a related structure and background to sulfonamides, see: Kant et al. (2012 ▶).

Experimental

Crystal data

C23H25BrN4O3S2

M = 549.50

Triclinic,

a = 9.8318 (3) Å

b = 10.3822 (3) Å

c = 13.4393 (4) Å

α = 96.654 (3)°

β = 103.085 (3)°

γ = 107.714 (3)°

V = 1247.36 (6) Å3

Z = 2

Mo Kα radiation

μ = 1.85 mm−1

T = 293 K

0.30 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur CCD, Sapphire3 diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 ▶) T min = 0.764, T max = 1.000

41580 measured reflections

4385 independent reflections

3645 reflections with I > 2σ(I)

R int = 0.038

Refinement

R[F 2 > 2σ(F 2)] = 0.037

wR(F 2) = 0.093

S = 1.03

4385 reflections

300 parameters

H-atom parameters constrained

Δρmax = 0.66 e Å−3

Δρmin = −0.52 e Å−3

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

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812037257/hb6947sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812037257/hb6947Isup2.hkl

Supplementary material file. DOI: 10.1107/S1600536812037257/hb6947Isup3.cml

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

C23H25BrN4O3S2	Z = 2
Mr = 549.50	F(000) = 564
Triclinic, P1	Dx = 1.463 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.8318 (3) Å	Cell parameters from 16775 reflections
b = 10.3822 (3) Å	θ = 3.4–29.1°
c = 13.4393 (4) Å	µ = 1.85 mm−1
α = 96.654 (3)°	T = 293 K
β = 103.085 (3)°	Block, light-brown
γ = 107.714 (3)°	0.30 × 0.20 × 0.20 mm
V = 1247.36 (6) Å3

Oxford Diffraction Xcalibur CCD, Sapphire3 diffractometer	4385 independent reflections
Radiation source: fine-focus sealed tube	3645 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.038
Detector resolution: 16.1049 pixels mm-1	θmax = 25.0°, θmin = 3.4°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −12→12
Tmin = 0.764, Tmax = 1.000	l = −15→15
41580 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)] = 0.037	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.093	H-atom parameters constrained
S = 1.03	w = 1/[σ2(Fo2) + (0.0396P)2 + 0.9744P] where P = (Fo2 + 2Fc2)/3
4385 reflections	(Δ/σ)max = 0.001
300 parameters	Δρmax = 0.66 e Å−3
0 restraints	Δρmin = −0.52 e Å−3

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.

	x	y	z	Uiso*/Ueq
Br1	0.00669 (4)	0.82027 (4)	0.88239 (3)	0.06852 (14)
S1	0.22673 (8)	0.63699 (8)	0.49289 (5)	0.04950 (19)
S2	0.20227 (7)	0.65245 (7)	0.79943 (5)	0.04366 (17)
O1	0.3610 (3)	0.6577 (2)	0.46369 (16)	0.0639 (6)
O2	0.0875 (3)	0.5665 (2)	0.41649 (15)	0.0656 (6)
C1	0.2248 (3)	0.7998 (3)	0.5459 (2)	0.0449 (6)
C2	0.0995 (4)	0.8109 (3)	0.5695 (3)	0.0582 (8)
H2	0.0164	0.7326	0.5593	0.070*
C3	0.0980 (4)	0.9391 (4)	0.6086 (3)	0.0696 (9)
H3	0.0134	0.9463	0.6252	0.084*
C4	0.2194 (4)	1.0571 (3)	0.6237 (3)	0.0642 (9)
C5	0.3433 (4)	1.0432 (3)	0.6002 (3)	0.0672 (9)
H5	0.4261	1.1216	0.6100	0.081*
C6	0.3486 (3)	0.9157 (3)	0.5622 (2)	0.0574 (8)
H6	0.4344	0.9082	0.5479	0.069*
C7	0.2160 (6)	1.1970 (4)	0.6657 (4)	0.1016 (15)
H7A	0.3102	1.2506	0.7142	0.152*
H7B	0.1391	1.1858	0.7005	0.152*
H7C	0.1965	1.2435	0.6092	0.152*
N8	0.2273 (3)	0.5458 (2)	0.58395 (17)	0.0485 (6)
H8	0.1476	0.4793	0.5805	0.058*
C9	0.3552 (3)	0.5726 (3)	0.6691 (2)	0.0428 (6)
C10	0.4798 (4)	0.5487 (3)	0.6516 (2)	0.0599 (8)
H10	0.4800	0.5182	0.5838	0.072*
C11	0.6028 (4)	0.5690 (4)	0.7322 (3)	0.0629 (8)
H11	0.6868	0.5558	0.7185	0.076*
C12	0.6023 (3)	0.6090 (3)	0.8336 (2)	0.0527 (7)
C13	0.4792 (3)	0.6322 (3)	0.8528 (2)	0.0451 (6)
H13	0.4783	0.6592	0.9210	0.054*
C14	0.3561 (3)	0.6157 (2)	0.7709 (2)	0.0391 (6)
O15	0.7290 (2)	0.6271 (3)	0.9099 (2)	0.0810 (8)
C16	0.7150 (4)	0.5974 (4)	1.0061 (3)	0.0660 (9)
H16A	0.6837	0.6649	1.0407	0.099*
H16B	0.8090	0.5995	1.0480	0.099*
H16C	0.6425	0.5074	0.9960	0.099*
C17	0.2812 (3)	0.8343 (3)	0.83612 (18)	0.0391 (6)
N18	0.4152 (2)	0.8963 (2)	0.82825 (16)	0.0399 (5)
C19	0.4729 (3)	1.0343 (3)	0.8579 (2)	0.0444 (6)
N20	0.4065 (3)	1.1143 (2)	0.8998 (2)	0.0560 (6)
C21	0.2713 (4)	1.0476 (3)	0.9059 (2)	0.0584 (8)
H21	0.2212	1.0990	0.9337	0.070*
C22	0.2008 (3)	0.9085 (3)	0.8739 (2)	0.0480 (7)
N23	0.6066 (3)	1.0965 (2)	0.8425 (2)	0.0548 (6)
C24	0.6954 (4)	1.0140 (3)	0.8157 (3)	0.0648 (9)
H24A	0.6300	0.9209	0.7819	0.078*
H24B	0.7626	1.0088	0.8789	0.078*
C25	0.7831 (4)	1.0749 (4)	0.7447 (3)	0.0768 (10)
H25A	0.7158	1.0658	0.6771	0.092*
H25B	0.8488	1.0242	0.7350	0.092*
C26	0.8740 (4)	1.2256 (4)	0.7879 (3)	0.0828 (11)
H26A	0.9498	1.2343	0.8512	0.099*
H26B	0.9233	1.2638	0.7377	0.099*
C27	0.7764 (4)	1.3046 (4)	0.8112 (3)	0.0788 (11)
H27A	0.8377	1.3992	0.8440	0.095*
H27B	0.7097	1.3061	0.7463	0.095*
C28	0.6865 (4)	1.2435 (3)	0.8813 (3)	0.0685 (9)
H28A	0.7519	1.2578	0.9506	0.082*
H28B	0.6160	1.2903	0.8865	0.082*

	U11	U22	U33	U12	U13	U23
Br1	0.0502 (2)	0.0873 (3)	0.0799 (3)	0.03164 (18)	0.02998 (17)	0.01633 (19)
S1	0.0587 (4)	0.0511 (4)	0.0322 (3)	0.0106 (3)	0.0140 (3)	0.0029 (3)
S2	0.0408 (4)	0.0443 (4)	0.0436 (4)	0.0102 (3)	0.0162 (3)	0.0030 (3)
O1	0.0750 (15)	0.0739 (15)	0.0493 (12)	0.0249 (12)	0.0317 (11)	0.0101 (11)
O2	0.0735 (15)	0.0658 (14)	0.0344 (10)	0.0018 (11)	0.0058 (10)	−0.0003 (10)
C1	0.0497 (16)	0.0481 (16)	0.0329 (13)	0.0118 (13)	0.0089 (12)	0.0108 (12)
C2	0.0544 (18)	0.0514 (18)	0.066 (2)	0.0141 (14)	0.0163 (15)	0.0143 (15)
C3	0.070 (2)	0.072 (2)	0.079 (2)	0.0362 (19)	0.0254 (19)	0.0203 (19)
C4	0.081 (2)	0.0513 (19)	0.058 (2)	0.0264 (18)	0.0082 (17)	0.0154 (15)
C5	0.071 (2)	0.0516 (19)	0.061 (2)	0.0040 (16)	0.0074 (17)	0.0133 (16)
C6	0.0541 (18)	0.0562 (19)	0.0553 (18)	0.0088 (15)	0.0157 (14)	0.0115 (15)
C7	0.137 (4)	0.063 (2)	0.107 (3)	0.050 (3)	0.019 (3)	0.012 (2)
N8	0.0601 (15)	0.0382 (12)	0.0391 (12)	0.0074 (11)	0.0136 (11)	0.0029 (10)
C9	0.0565 (16)	0.0323 (13)	0.0421 (15)	0.0160 (12)	0.0181 (13)	0.0060 (11)
C10	0.082 (2)	0.065 (2)	0.0509 (18)	0.0386 (18)	0.0351 (17)	0.0115 (15)
C11	0.065 (2)	0.076 (2)	0.071 (2)	0.0401 (18)	0.0359 (18)	0.0246 (18)
C12	0.0499 (17)	0.0580 (18)	0.0585 (18)	0.0205 (14)	0.0216 (14)	0.0241 (15)
C13	0.0482 (15)	0.0457 (15)	0.0420 (15)	0.0128 (12)	0.0170 (12)	0.0111 (12)
C14	0.0446 (14)	0.0304 (13)	0.0436 (14)	0.0107 (11)	0.0181 (12)	0.0065 (11)
O15	0.0464 (13)	0.125 (2)	0.0810 (17)	0.0292 (13)	0.0216 (12)	0.0489 (16)
C16	0.062 (2)	0.065 (2)	0.062 (2)	0.0191 (17)	0.0039 (16)	0.0112 (17)
C17	0.0440 (15)	0.0459 (15)	0.0286 (12)	0.0183 (12)	0.0095 (11)	0.0053 (11)
N18	0.0460 (12)	0.0388 (12)	0.0372 (11)	0.0153 (10)	0.0164 (10)	0.0046 (9)
C19	0.0560 (17)	0.0430 (15)	0.0368 (14)	0.0187 (13)	0.0165 (12)	0.0052 (12)
N20	0.0729 (17)	0.0441 (14)	0.0582 (15)	0.0233 (13)	0.0301 (13)	0.0045 (11)
C21	0.074 (2)	0.0546 (19)	0.0634 (19)	0.0356 (17)	0.0342 (17)	0.0089 (15)
C22	0.0498 (16)	0.0595 (18)	0.0442 (15)	0.0268 (14)	0.0198 (13)	0.0107 (13)
N23	0.0581 (15)	0.0410 (13)	0.0651 (16)	0.0119 (11)	0.0273 (13)	0.0036 (11)
C24	0.0604 (19)	0.0529 (19)	0.085 (2)	0.0163 (15)	0.0339 (18)	0.0089 (17)
C25	0.069 (2)	0.091 (3)	0.084 (3)	0.033 (2)	0.037 (2)	0.021 (2)
C26	0.065 (2)	0.087 (3)	0.101 (3)	0.016 (2)	0.036 (2)	0.039 (2)
C27	0.080 (2)	0.062 (2)	0.094 (3)	0.0160 (19)	0.027 (2)	0.029 (2)
C28	0.076 (2)	0.0458 (18)	0.073 (2)	0.0069 (16)	0.0225 (18)	0.0026 (16)

Br1—C22	1.885 (3)	C13—C14	1.390 (4)
S1—O1	1.423 (2)	C13—H13	0.9300
S1—O2	1.429 (2)	O15—C16	1.390 (4)
S1—N8	1.632 (2)	C16—H16A	0.9600
S1—C1	1.764 (3)	C16—H16B	0.9600
S2—C17	1.769 (3)	C16—H16C	0.9600
S2—C14	1.778 (3)	C17—N18	1.313 (3)
C1—C2	1.374 (4)	C17—C22	1.393 (4)
C1—C6	1.380 (4)	N18—C19	1.343 (3)
C2—C3	1.379 (5)	C19—N20	1.350 (3)
C2—H2	0.9300	C19—N23	1.351 (4)
C3—C4	1.382 (5)	N20—C21	1.325 (4)
C3—H3	0.9300	C21—C22	1.365 (4)
C4—C5	1.370 (5)	C21—H21	0.9300
C4—C7	1.509 (5)	N23—C28	1.456 (4)
C5—C6	1.383 (5)	N23—C24	1.467 (4)
C5—H5	0.9300	C24—C25	1.494 (5)
C6—H6	0.9300	C24—H24A	0.9700
C7—H7A	0.9600	C24—H24B	0.9700
C7—H7B	0.9600	C25—C26	1.513 (5)
C7—H7C	0.9600	C25—H25A	0.9700
N8—C9	1.425 (4)	C25—H25B	0.9700
N8—H8	0.8600	C26—C27	1.499 (5)
C9—C10	1.385 (4)	C26—H26A	0.9700
C9—C14	1.386 (4)	C26—H26B	0.9700
C10—C11	1.371 (5)	C27—C28	1.498 (5)
C10—H10	0.9300	C27—H27A	0.9700
C11—C12	1.380 (4)	C27—H27B	0.9700
C11—H11	0.9300	C28—H28A	0.9700
C12—O15	1.369 (4)	C28—H28B	0.9700
C12—C13	1.376 (4)
O1—S1—O2	119.46 (13)	O15—C16—H16A	109.5
O1—S1—N8	108.46 (14)	O15—C16—H16B	109.5
O2—S1—N8	104.72 (13)	H16A—C16—H16B	109.5
O1—S1—C1	107.97 (14)	O15—C16—H16C	109.5
O2—S1—C1	107.66 (14)	H16A—C16—H16C	109.5
N8—S1—C1	108.12 (12)	H16B—C16—H16C	109.5
C17—S2—C14	99.34 (12)	N18—C17—C22	121.4 (3)
C2—C1—C6	120.3 (3)	N18—C17—S2	119.23 (19)
C2—C1—S1	119.8 (2)	C22—C17—S2	119.4 (2)
C6—C1—S1	119.9 (2)	C17—N18—C19	117.9 (2)
C1—C2—C3	119.4 (3)	N18—C19—N20	125.1 (3)
C1—C2—H2	120.3	N18—C19—N23	116.7 (2)
C3—C2—H2	120.3	N20—C19—N23	118.2 (3)
C2—C3—C4	121.5 (3)	C21—N20—C19	115.0 (3)
C2—C3—H3	119.3	N20—C21—C22	124.3 (3)
C4—C3—H3	119.3	N20—C21—H21	117.8
C5—C4—C3	118.0 (3)	C22—C21—H21	117.8
C5—C4—C7	121.0 (4)	C21—C22—C17	116.3 (3)
C3—C4—C7	121.0 (4)	C21—C22—Br1	122.2 (2)
C4—C5—C6	121.7 (3)	C17—C22—Br1	121.5 (2)
C4—C5—H5	119.1	C19—N23—C28	121.4 (2)
C6—C5—H5	119.1	C19—N23—C24	120.1 (2)
C1—C6—C5	119.1 (3)	C28—N23—C24	115.9 (3)
C1—C6—H6	120.4	N23—C24—C25	111.5 (3)
C5—C6—H6	120.4	N23—C24—H24A	109.3
C4—C7—H7A	109.5	C25—C24—H24A	109.3
C4—C7—H7B	109.5	N23—C24—H24B	109.3
H7A—C7—H7B	109.5	C25—C24—H24B	109.3
C4—C7—H7C	109.5	H24A—C24—H24B	108.0
H7A—C7—H7C	109.5	C24—C25—C26	111.6 (3)
H7B—C7—H7C	109.5	C24—C25—H25A	109.3
C9—N8—S1	122.28 (19)	C26—C25—H25A	109.3
C9—N8—H8	118.9	C24—C25—H25B	109.3
S1—N8—H8	118.9	C26—C25—H25B	109.3
C10—C9—C14	118.4 (3)	H25A—C25—H25B	108.0
C10—C9—N8	120.0 (2)	C27—C26—C25	110.4 (3)
C14—C9—N8	121.5 (2)	C27—C26—H26A	109.6
C11—C10—C9	121.4 (3)	C25—C26—H26A	109.6
C11—C10—H10	119.3	C27—C26—H26B	109.6
C9—C10—H10	119.3	C25—C26—H26B	109.6
C10—C11—C12	120.0 (3)	H26A—C26—H26B	108.1
C10—C11—H11	120.0	C28—C27—C26	112.5 (3)
C12—C11—H11	120.0	C28—C27—H27A	109.1
O15—C12—C13	123.8 (3)	C26—C27—H27A	109.1
O15—C12—C11	116.7 (3)	C28—C27—H27B	109.1
C13—C12—C11	119.5 (3)	C26—C27—H27B	109.1
C12—C13—C14	120.4 (3)	H27A—C27—H27B	107.8
C12—C13—H13	119.8	N23—C28—C27	111.5 (3)
C14—C13—H13	119.8	N23—C28—H28A	109.3
C9—C14—C13	120.1 (2)	C27—C28—H28A	109.3
C9—C14—S2	121.1 (2)	N23—C28—H28B	109.3
C13—C14—S2	118.7 (2)	C27—C28—H28B	109.3
C12—O15—C16	118.1 (2)	H28A—C28—H28B	108.0
O1—S1—C1—C2	172.6 (2)	C12—C13—C14—S2	−178.0 (2)
O2—S1—C1—C2	42.4 (3)	C17—S2—C14—C9	−108.1 (2)
N8—S1—C1—C2	−70.2 (3)	C17—S2—C14—C13	71.3 (2)
O1—S1—C1—C6	−6.6 (3)	C13—C12—O15—C16	34.4 (5)
O2—S1—C1—C6	−136.8 (2)	C11—C12—O15—C16	−147.6 (3)
N8—S1—C1—C6	110.5 (2)	C14—S2—C17—N18	4.4 (2)
C6—C1—C2—C3	0.7 (5)	C14—S2—C17—C22	−174.8 (2)
S1—C1—C2—C3	−178.5 (2)	C22—C17—N18—C19	0.0 (4)
C1—C2—C3—C4	0.6 (5)	S2—C17—N18—C19	−179.23 (19)
C2—C3—C4—C5	−1.0 (5)	C17—N18—C19—N20	3.2 (4)
C2—C3—C4—C7	179.5 (3)	C17—N18—C19—N23	−175.7 (2)
C3—C4—C5—C6	0.1 (5)	N18—C19—N20—C21	−3.4 (4)
C7—C4—C5—C6	179.6 (3)	N23—C19—N20—C21	175.5 (3)
C2—C1—C6—C5	−1.6 (4)	C19—N20—C21—C22	0.5 (5)
S1—C1—C6—C5	177.6 (2)	N20—C21—C22—C17	2.2 (5)
C4—C5—C6—C1	1.2 (5)	N20—C21—C22—Br1	−178.8 (2)
O1—S1—N8—C9	43.7 (2)	N18—C17—C22—C21	−2.5 (4)
O2—S1—N8—C9	172.3 (2)	S2—C17—C22—C21	176.7 (2)
C1—S1—N8—C9	−73.1 (2)	N18—C17—C22—Br1	178.55 (19)
S1—N8—C9—C10	−67.8 (3)	S2—C17—C22—Br1	−2.3 (3)
S1—N8—C9—C14	115.5 (3)	N18—C19—N23—C28	−173.6 (3)
C14—C9—C10—C11	−1.1 (4)	N20—C19—N23—C28	7.4 (4)
N8—C9—C10—C11	−177.8 (3)	N18—C19—N23—C24	−12.3 (4)
C9—C10—C11—C12	2.5 (5)	N20—C19—N23—C24	168.7 (3)
C10—C11—C12—O15	179.9 (3)	C19—N23—C24—C25	146.5 (3)
C10—C11—C12—C13	−1.9 (5)	C28—N23—C24—C25	−51.2 (4)
O15—C12—C13—C14	178.0 (3)	N23—C24—C25—C26	52.4 (4)
C11—C12—C13—C14	0.0 (4)	C24—C25—C26—C27	−54.7 (4)
C10—C9—C14—C13	−0.9 (4)	C25—C26—C27—C28	54.2 (5)
N8—C9—C14—C13	175.8 (2)	C19—N23—C28—C27	−147.7 (3)
C10—C9—C14—S2	178.5 (2)	C24—N23—C28—C27	50.3 (4)
N8—C9—C14—S2	−4.8 (3)	C26—C27—C28—N23	−51.4 (5)
C12—C13—C14—C9	1.4 (4)

D—H···A	D—H	H···A	D···A	D—H···A
N8—H8···O2i	0.86	2.22	2.955 (4)	143

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N8—H8⋯O2i	0.86	2.22	2.955 (4)	143

Symmetry code: (i) .