organic compounds
N-(2-{[5-Bromo-2-(piperidin-1-yl)pyrimidin-4-yl]sulfanyl}-4-methoxyphenyl)-4-methylbenzenesulfonamide
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
In the title compound, C23H25BrN4O3S2, 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 molecular conformation is stabilized by a weak intramolecular π–π stacking interaction 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, molecules are linked into inversion dimers by pairs of N—H⋯O hydrogen bonds.
Experimental
Crystal data
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Refinement
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Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell 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
https://doi.org/10.1107/S1600536812037257/hb6947sup1.cif
contains datablocks I, global. DOI:Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536812037257/hb6947Isup2.hkl
Supporting information file. DOI: https://doi.org/10.1107/S1600536812037257/hb6947Isup3.cml
The reaction of N-[2-(5-bromo-2-piperidin-1-yl-pyrimidin-4-ylsulfanyl)-4-methoxy -phenyl]-4-methyl-benzenesulfonamide (5.01 g, 0.01 mol) and piperidine (0.86 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. 483–485 K) to yield light brown blocks of (I).
All H atoms were positioned geometrically and were treated as riding on their parent C atoms, with C—H distances of 0.93–0.97 Å and with Uiso(H) = 1.2Ueq(C) or 1.5Ueq(methyl C).
As part of our ongoing studies of
(Kant et al., 2012), we now report the structure of the title compound, (I), (Fig. 1).The piperidine ring is exhibiting a chair conformation. The two benzene rings (C1—C6/C9—C14) 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
is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 4 -methyl benzene rings [centroid–centroid distance = 3.633 (2) Å, = 3.494 Å, and centroid shift = 1.00 Å]. In the crystal, molecules are linked into inversion dimers by pairs of N8—H8···O2 hydrogen bonds (Fig.2).For a related structure and background to
see: Kant et al. (2012).Data collection: CrysAlis PRO (Oxford Diffraction, 2010); cell
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).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 |
C23H25BrN4O3S2 | γ = 107.714 (3)° |
Mr = 549.50 | V = 1247.36 (6) Å3 |
Triclinic, P1 | Z = 2 |
a = 9.8318 (3) Å | Mo Kα radiation |
b = 10.3822 (3) Å | µ = 1.85 mm−1 |
c = 13.4393 (4) Å | T = 293 K |
α = 96.654 (3)° | 0.30 × 0.20 × 0.20 mm |
β = 103.085 (3)° |
Oxford Diffraction Xcalibur CCD, Sapphire3 diffractometer | 4385 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 3645 reflections with I > 2σ(I) |
Tmin = 0.764, Tmax = 1.000 | Rint = 0.038 |
41580 measured reflections |
R[F2 > 2σ(F2)] = 0.037 | 0 restraints |
wR(F2) = 0.093 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.66 e Å−3 |
4385 reflections | Δρmin = −0.52 e Å−3 |
300 parameters |
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 |
Symmetry code: (i) −x, −y+1, −z+1. |
Experimental details
Crystal data | |
Chemical formula | C23H25BrN4O3S2 |
Mr | 549.50 |
Crystal system, space group | Triclinic, P1 |
Temperature (K) | 293 |
a, b, c (Å) | 9.8318 (3), 10.3822 (3), 13.4393 (4) |
α, β, γ (°) | 96.654 (3), 103.085 (3), 107.714 (3) |
V (Å3) | 1247.36 (6) |
Z | 2 |
Radiation type | Mo Kα |
µ (mm−1) | 1.85 |
Crystal size (mm) | 0.30 × 0.20 × 0.20 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur CCD, Sapphire3 |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.764, 1.000 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 41580, 4385, 3645 |
Rint | 0.038 |
(sin θ/λ)max (Å−1) | 0.595 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.037, 0.093, 1.03 |
No. of reflections | 4385 |
No. of parameters | 300 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.66, −0.52 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEP-3 (Farrugia, 1997), PLATON (Spek, 2009).
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) −x, −y+1, −z+1. |
Acknowledgements
MK acknowledges the help of Bahubali College of Engineering, Shravanabelagola for his research work and 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
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
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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As part of our ongoing studies of sulfonamides (Kant et al., 2012), we now report the structure of the title compound, (I), (Fig. 1).
The piperidine ring is exhibiting a chair conformation. The two benzene rings (C1—C6/C9—C14) 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 molecular conformation is stabilized by a weak intramolecular stacking interaction between the pyrimidine and the 4 -methyl benzene rings [centroid–centroid distance = 3.633 (2) Å, interplanar spacing = 3.494 Å, and centroid shift = 1.00 Å]. In the crystal, molecules are linked into inversion dimers by pairs of N8—H8···O2 hydrogen bonds (Fig.2).