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organic compounds
3-[Bis(p-tolylsulfonyl)amino]-N-(4-chlorobenzyl)-6-(3,4-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide
aState Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, People's Republic of China, and bWest China School of Pharmacy, Sichuan University, Chengdu 610041, People's Republic of China
*Correspondence e-mail: yangli@scu.edu.cn
In the title compound, C35H26Cl3N3O5S3, the dihedral angle between the mean plane through the thieno[2,3-b]pyridine ring system and the attached benzene ring is 3.89 (6)°. The molecular conformation is stabilized by an intramolecular N—H⋯O hydrogen bond. In the crystal, molecules are linked by intermolecular C—H⋯O hydrogen bonds, forming chains parallel to [100].
Related literature
For general background to the biological properties of thieno[2,3-b]pyridine derivatives, see: Litvinov et al. (2005).
Experimental
Crystal data
|
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: OLEX2 (Dolomanov et al., 2009
); software used to prepare material for publication: SHELXTL (Sheldrick, 2008
) and OLEX2.
Supporting information
10.1107/S160053681100290X/rz2547sup1.cif
contains datablocks global, I. DOI:Structure factors: contains datablock I. DOI: 10.1107/S160053681100290X/rz2547Isup2.hkl
To a solution of 3-amino-N-(4-chlorobenzyl)-6-(3,4-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide (1.39 g, 3 mmol) in tetrahydrofuran (10 ml) and triethylamine (0.63 ml) was added p-toluenesulfonyl chloride (1.14 g, 6 mmol). After stirring for 5 minutes, N,N-4-dimethylaminopyridine (48 mg, 0.39 mmol) was added and the mixture was stirred at room temperature until the reaction was completed (as monitored by TLC). The reaction mixture was concentrated in vacuo and the resulting residue was treated with a dilute HCl solution and extracted with ethyl acetate. The organic phase was dried over MgSO4 and then was evaporated under reduced pressure. The residue was chromatographed on silica gel using petroleum ether-ethyl acetate (9:1 v/v) as
The product was recrystallized from ethanol to afford the title compound as an off-white solid (yield: 60%). Crystals suitable for X-ray analysis were obtained by slow evaporation of an ethyl acetate solution.All H atoms were positioned geometrically (N—H = 0.86 Å; C—H = 0.93–0.97 Å) and refined using a riding model, with Uiso(H) = 1.2Ueq(C, N) or 1.2Ueq(C) for methyl H atoms. The crystal was ground into a spheroidal shape.
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: OLEX2 (Dolomanov et al., 2009); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).C35H26Cl3N3O5S3 | F(000) = 1584 |
Mr = 771.15 | Dx = 1.493 Mg m−3 |
Monoclinic, P21/c | Mo Kα radiation, λ = 0.7107 Å |
Hall symbol: -P 2ybc | Cell parameters from 6766 reflections |
a = 25.8238 (8) Å | θ = 3.1–29.1° |
b = 9.1634 (2) Å | µ = 0.50 mm−1 |
c = 14.8366 (5) Å | T = 294 K |
β = 102.314 (3)° | Block, colourless |
V = 3430.07 (17) Å3 | 0.36 × 0.28 × 0.16 mm |
Z = 4 |
Oxford Diffraction Xcalibur Eos diffractometer | 7014 independent reflections |
Radiation source: fine-focus sealed tube | 4515 reflections with I > 2σ(I) |
Graphite monochromator | Rint = 0.024 |
Detector resolution: 16.0874 pixels mm-1 | θmax = 26.4°, θmin = 3.1° |
ω scans | h = −28→32 |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | k = −10→11 |
Tmin = 0.695, Tmax = 1.0 | l = −18→9 |
14766 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)] = 0.043 | Hydrogen site location: inferred from neighbouring sites |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.03 | w = 1/[σ2(Fo2) + (0.0514P)2] where P = (Fo2 + 2Fc2)/3 |
7014 reflections | (Δ/σ)max = 0.001 |
444 parameters | Δρmax = 0.28 e Å−3 |
0 restraints | Δρmin = −0.35 e Å−3 |
C35H26Cl3N3O5S3 | V = 3430.07 (17) Å3 |
Mr = 771.15 | Z = 4 |
Monoclinic, P21/c | Mo Kα radiation |
a = 25.8238 (8) Å | µ = 0.50 mm−1 |
b = 9.1634 (2) Å | T = 294 K |
c = 14.8366 (5) Å | 0.36 × 0.28 × 0.16 mm |
β = 102.314 (3)° |
Oxford Diffraction Xcalibur Eos diffractometer | 7014 independent reflections |
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) | 4515 reflections with I > 2σ(I) |
Tmin = 0.695, Tmax = 1.0 | Rint = 0.024 |
14766 measured reflections |
R[F2 > 2σ(F2)] = 0.043 | 0 restraints |
wR(F2) = 0.105 | H-atom parameters constrained |
S = 1.03 | Δρmax = 0.28 e Å−3 |
7014 reflections | Δρmin = −0.35 e Å−3 |
444 parameters |
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 | ||
S3 | 0.28910 (2) | 0.51376 (6) | 0.40412 (4) | 0.04300 (16) | |
S2 | 0.23044 (2) | 0.51746 (6) | 0.20959 (4) | 0.04806 (17) | |
S1 | 0.24607 (2) | −0.00731 (5) | 0.31174 (4) | 0.04490 (16) | |
Cl2 | 0.02235 (3) | −0.41937 (7) | 0.38236 (6) | 0.0764 (2) | |
C12 | 0.24509 (9) | 0.2738 (2) | 0.31359 (14) | 0.0375 (5) | |
Cl3 | 0.52839 (4) | 0.81264 (11) | 0.41121 (7) | 0.1161 (4) | |
N2 | 0.26006 (7) | 0.42373 (17) | 0.30696 (12) | 0.0404 (5) | |
O3 | 0.30905 (7) | 0.64478 (16) | 0.37327 (12) | 0.0568 (5) | |
C2 | 0.05859 (9) | −0.1498 (2) | 0.35900 (16) | 0.0453 (6) | |
H2 | 0.0887 | −0.1967 | 0.3487 | 0.054* | |
O4 | 0.21021 (7) | 0.64976 (17) | 0.23812 (13) | 0.0641 (5) | |
N1 | 0.14607 (7) | 0.00580 (17) | 0.33823 (12) | 0.0400 (4) | |
C4 | −0.02829 (10) | −0.1637 (3) | 0.39124 (18) | 0.0542 (7) | |
C9 | 0.14909 (10) | 0.3121 (2) | 0.33334 (16) | 0.0448 (6) | |
H9 | 0.1497 | 0.4136 | 0.3323 | 0.054* | |
N3 | 0.36706 (7) | 0.2419 (2) | 0.31819 (14) | 0.0500 (5) | |
H3 | 0.3600 | 0.3039 | 0.3574 | 0.060* | |
C30 | 0.22700 (10) | 0.4507 (2) | 0.52574 (16) | 0.0480 (6) | |
H30 | 0.2448 | 0.3620 | 0.5346 | 0.058* | |
C33 | 0.17583 (10) | 0.7139 (2) | 0.50220 (17) | 0.0521 (6) | |
H33 | 0.1590 | 0.8042 | 0.4949 | 0.062* | |
C8 | 0.10435 (9) | 0.2384 (2) | 0.34211 (16) | 0.0459 (6) | |
H8 | 0.0740 | 0.2904 | 0.3461 | 0.055* | |
O2 | 0.32449 (6) | 0.40866 (16) | 0.45588 (11) | 0.0555 (5) | |
C14 | 0.33000 (9) | 0.1470 (2) | 0.27949 (17) | 0.0445 (6) | |
C1 | 0.05624 (9) | 0.0017 (2) | 0.35697 (15) | 0.0428 (5) | |
C26 | 0.34030 (9) | 0.7161 (3) | 0.10029 (17) | 0.0492 (6) | |
H26 | 0.3548 | 0.8089 | 0.0996 | 0.059* | |
C13 | 0.27713 (9) | 0.1581 (2) | 0.30390 (15) | 0.0385 (5) | |
C31 | 0.18809 (10) | 0.4803 (2) | 0.57265 (16) | 0.0485 (6) | |
H31 | 0.1794 | 0.4105 | 0.6125 | 0.058* | |
C34 | 0.21404 (10) | 0.6856 (2) | 0.45385 (18) | 0.0513 (6) | |
H34 | 0.2226 | 0.7549 | 0.4137 | 0.062* | |
C23 | 0.29804 (11) | 0.4418 (3) | 0.10271 (18) | 0.0560 (7) | |
H23 | 0.2839 | 0.3487 | 0.1039 | 0.067* | |
O5 | 0.19592 (7) | 0.41295 (19) | 0.15714 (12) | 0.0723 (6) | |
C25 | 0.35659 (10) | 0.6059 (3) | 0.04872 (17) | 0.0524 (6) | |
O1 | 0.33772 (7) | 0.0519 (2) | 0.22660 (15) | 0.0826 (6) | |
C6 | 0.00994 (10) | 0.0669 (3) | 0.3697 (2) | 0.0625 (7) | |
H6 | 0.0070 | 0.1681 | 0.3672 | 0.075* | |
C15 | 0.41940 (9) | 0.2435 (3) | 0.2959 (2) | 0.0628 (7) | |
H15A | 0.4158 | 0.2275 | 0.2303 | 0.075* | |
H15B | 0.4406 | 0.1646 | 0.3284 | 0.075* | |
C16 | 0.44723 (10) | 0.3864 (3) | 0.32238 (18) | 0.0513 (6) | |
C20 | 0.44696 (12) | 0.6484 (3) | 0.3235 (2) | 0.0670 (8) | |
H20 | 0.4294 | 0.7360 | 0.3067 | 0.080* | |
C24 | 0.33542 (11) | 0.4684 (3) | 0.05170 (18) | 0.0589 (7) | |
H24 | 0.3467 | 0.3927 | 0.0187 | 0.071* | |
C28 | 0.39610 (11) | 0.6335 (3) | −0.0109 (2) | 0.0760 (9) | |
H28C | 0.4306 | 0.6018 | 0.0210 | 0.114* | |
H28B | 0.3971 | 0.7360 | −0.0239 | 0.114* | |
H28A | 0.3858 | 0.5804 | −0.0676 | 0.114* | |
C21 | 0.42232 (11) | 0.5173 (3) | 0.29841 (19) | 0.0616 (7) | |
H21 | 0.3877 | 0.5173 | 0.2641 | 0.074* | |
C5 | −0.03178 (10) | −0.0148 (3) | 0.3858 (2) | 0.0700 (8) | |
H5 | −0.0627 | 0.0316 | 0.3932 | 0.084* | |
C17 | 0.49892 (11) | 0.3892 (3) | 0.3706 (2) | 0.0808 (10) | |
H17 | 0.5169 | 0.3019 | 0.3864 | 0.097* | |
C18 | 0.52456 (13) | 0.5207 (4) | 0.3958 (3) | 0.0962 (11) | |
H18 | 0.5597 | 0.5219 | 0.4277 | 0.115* | |
C27 | 0.30312 (9) | 0.6910 (2) | 0.15244 (16) | 0.0449 (6) | |
H27 | 0.2928 | 0.7657 | 0.1872 | 0.054* | |
C19 | 0.49776 (13) | 0.6474 (3) | 0.3735 (2) | 0.0696 (9) | |
C7 | 0.10363 (9) | 0.0855 (2) | 0.34518 (15) | 0.0393 (5) | |
C29 | 0.23995 (8) | 0.5521 (2) | 0.46522 (15) | 0.0394 (5) | |
C32 | 0.16117 (9) | 0.6127 (2) | 0.56199 (16) | 0.0458 (6) | |
C10 | 0.19388 (9) | 0.2313 (2) | 0.32598 (14) | 0.0354 (5) | |
C11 | 0.18908 (9) | 0.0798 (2) | 0.32815 (15) | 0.0375 (5) | |
C35 | 0.11862 (10) | 0.6470 (3) | 0.61305 (19) | 0.0618 (7) | |
H35B | 0.1118 | 0.5625 | 0.6470 | 0.093* | |
H35A | 0.0868 | 0.6743 | 0.5699 | 0.093* | |
H35C | 0.1299 | 0.7262 | 0.6550 | 0.093* | |
C22 | 0.28132 (9) | 0.5534 (2) | 0.15253 (15) | 0.0408 (5) | |
C3 | 0.01687 (9) | −0.2314 (2) | 0.37608 (16) | 0.0471 (6) | |
Cl1 | −0.07975 (3) | −0.26085 (8) | 0.41925 (6) | 0.0810 (3) |
U11 | U22 | U33 | U12 | U13 | U23 | |
S3 | 0.0431 (3) | 0.0354 (3) | 0.0480 (4) | −0.0049 (3) | 0.0041 (3) | −0.0046 (3) |
S2 | 0.0455 (4) | 0.0443 (3) | 0.0499 (4) | −0.0108 (3) | 0.0002 (3) | 0.0158 (3) |
S1 | 0.0478 (4) | 0.0284 (3) | 0.0617 (4) | −0.0050 (2) | 0.0189 (3) | 0.0021 (3) |
Cl2 | 0.0704 (5) | 0.0453 (4) | 0.1153 (7) | −0.0173 (3) | 0.0239 (5) | 0.0019 (4) |
C12 | 0.0464 (13) | 0.0285 (10) | 0.0370 (13) | −0.0075 (10) | 0.0079 (11) | 0.0037 (9) |
Cl3 | 0.1143 (8) | 0.1157 (7) | 0.1354 (9) | −0.0746 (6) | 0.0649 (7) | −0.0587 (6) |
N2 | 0.0477 (11) | 0.0267 (9) | 0.0432 (11) | −0.0106 (8) | 0.0017 (9) | 0.0052 (8) |
O3 | 0.0590 (11) | 0.0400 (9) | 0.0748 (13) | −0.0212 (8) | 0.0220 (10) | −0.0131 (8) |
C2 | 0.0381 (13) | 0.0454 (13) | 0.0523 (16) | −0.0039 (10) | 0.0097 (12) | −0.0011 (11) |
O4 | 0.0583 (11) | 0.0537 (10) | 0.0838 (14) | 0.0138 (8) | 0.0228 (10) | 0.0298 (9) |
N1 | 0.0413 (10) | 0.0343 (9) | 0.0460 (11) | −0.0070 (8) | 0.0129 (9) | 0.0044 (8) |
C4 | 0.0434 (15) | 0.0596 (16) | 0.0596 (18) | −0.0126 (12) | 0.0109 (13) | 0.0047 (13) |
C9 | 0.0558 (15) | 0.0271 (11) | 0.0521 (15) | −0.0044 (11) | 0.0126 (12) | 0.0032 (10) |
N3 | 0.0449 (12) | 0.0478 (11) | 0.0613 (14) | −0.0082 (9) | 0.0199 (10) | −0.0094 (10) |
C30 | 0.0597 (16) | 0.0328 (12) | 0.0481 (15) | 0.0053 (11) | 0.0039 (13) | 0.0067 (11) |
C33 | 0.0560 (16) | 0.0377 (13) | 0.0620 (17) | 0.0089 (11) | 0.0115 (14) | 0.0041 (12) |
C8 | 0.0450 (14) | 0.0365 (12) | 0.0568 (16) | 0.0024 (10) | 0.0121 (12) | 0.0039 (11) |
O2 | 0.0518 (11) | 0.0597 (10) | 0.0488 (11) | 0.0126 (8) | −0.0028 (8) | −0.0083 (8) |
C14 | 0.0501 (15) | 0.0350 (12) | 0.0511 (15) | −0.0064 (11) | 0.0168 (12) | −0.0010 (11) |
C1 | 0.0418 (13) | 0.0450 (13) | 0.0417 (13) | −0.0036 (10) | 0.0094 (11) | 0.0049 (11) |
C26 | 0.0481 (15) | 0.0429 (13) | 0.0552 (16) | −0.0057 (11) | 0.0077 (13) | 0.0104 (12) |
C13 | 0.0448 (13) | 0.0308 (11) | 0.0405 (13) | −0.0082 (10) | 0.0102 (11) | 0.0016 (9) |
C31 | 0.0591 (16) | 0.0416 (13) | 0.0430 (14) | −0.0070 (12) | 0.0072 (12) | 0.0060 (11) |
C34 | 0.0639 (17) | 0.0335 (12) | 0.0572 (17) | −0.0011 (11) | 0.0144 (14) | 0.0097 (11) |
C23 | 0.0736 (19) | 0.0385 (13) | 0.0511 (16) | −0.0112 (13) | 0.0029 (14) | −0.0021 (12) |
O5 | 0.0691 (12) | 0.0808 (12) | 0.0542 (12) | −0.0417 (10) | −0.0155 (10) | 0.0201 (9) |
C25 | 0.0463 (15) | 0.0660 (17) | 0.0419 (15) | 0.0071 (12) | 0.0027 (12) | 0.0103 (13) |
O1 | 0.0674 (13) | 0.0762 (13) | 0.1151 (18) | −0.0227 (10) | 0.0441 (12) | −0.0461 (12) |
C6 | 0.0542 (16) | 0.0484 (14) | 0.090 (2) | 0.0004 (13) | 0.0270 (15) | 0.0093 (14) |
C15 | 0.0445 (15) | 0.0594 (16) | 0.090 (2) | −0.0071 (12) | 0.0275 (15) | −0.0076 (15) |
C16 | 0.0396 (14) | 0.0616 (16) | 0.0559 (17) | −0.0103 (12) | 0.0171 (13) | −0.0042 (13) |
C20 | 0.071 (2) | 0.0626 (17) | 0.071 (2) | −0.0108 (15) | 0.0216 (17) | −0.0036 (14) |
C24 | 0.0744 (19) | 0.0529 (15) | 0.0477 (16) | 0.0047 (14) | 0.0093 (15) | −0.0105 (12) |
C28 | 0.0600 (19) | 0.096 (2) | 0.076 (2) | 0.0128 (16) | 0.0248 (17) | 0.0166 (17) |
C21 | 0.0488 (15) | 0.0629 (17) | 0.0687 (19) | −0.0102 (13) | 0.0030 (14) | −0.0025 (14) |
C5 | 0.0465 (16) | 0.0672 (18) | 0.103 (2) | 0.0012 (13) | 0.0320 (16) | 0.0114 (16) |
C17 | 0.0462 (18) | 0.083 (2) | 0.108 (3) | −0.0003 (15) | 0.0051 (18) | 0.0060 (18) |
C18 | 0.0473 (19) | 0.120 (3) | 0.115 (3) | −0.025 (2) | 0.0028 (19) | −0.021 (2) |
C27 | 0.0542 (15) | 0.0337 (11) | 0.0462 (15) | −0.0031 (11) | 0.0098 (12) | 0.0046 (10) |
C19 | 0.063 (2) | 0.082 (2) | 0.073 (2) | −0.0371 (17) | 0.0353 (17) | −0.0254 (17) |
C7 | 0.0427 (13) | 0.0379 (12) | 0.0372 (13) | −0.0033 (10) | 0.0081 (11) | 0.0056 (10) |
C29 | 0.0414 (13) | 0.0289 (11) | 0.0446 (14) | −0.0033 (10) | 0.0022 (11) | 0.0005 (10) |
C32 | 0.0418 (14) | 0.0489 (14) | 0.0437 (15) | −0.0037 (11) | 0.0024 (12) | −0.0056 (11) |
C10 | 0.0432 (13) | 0.0286 (10) | 0.0336 (12) | −0.0042 (9) | 0.0063 (10) | 0.0032 (9) |
C11 | 0.0457 (13) | 0.0313 (11) | 0.0358 (13) | −0.0061 (10) | 0.0096 (10) | 0.0047 (9) |
C35 | 0.0574 (17) | 0.0630 (16) | 0.0658 (19) | −0.0037 (13) | 0.0146 (15) | −0.0050 (14) |
C22 | 0.0496 (14) | 0.0313 (11) | 0.0382 (13) | −0.0047 (10) | 0.0017 (11) | 0.0048 (10) |
C3 | 0.0428 (14) | 0.0458 (13) | 0.0499 (16) | −0.0101 (11) | 0.0035 (12) | 0.0050 (11) |
Cl1 | 0.0537 (4) | 0.0854 (5) | 0.1103 (7) | −0.0211 (4) | 0.0320 (4) | 0.0109 (5) |
S3—N2 | 1.6911 (18) | C1—C7 | 1.486 (3) |
S3—O3 | 1.4202 (15) | C26—H26 | 0.9300 |
S3—O2 | 1.4328 (16) | C26—C25 | 1.385 (3) |
S3—C29 | 1.746 (2) | C26—C27 | 1.375 (3) |
S2—N2 | 1.7142 (17) | C31—H31 | 0.9300 |
S2—O4 | 1.4200 (18) | C31—C32 | 1.390 (3) |
S2—O5 | 1.4218 (17) | C34—H34 | 0.9300 |
S2—C22 | 1.740 (2) | C34—C29 | 1.387 (3) |
S1—C13 | 1.730 (2) | C23—H23 | 0.9300 |
S1—C11 | 1.736 (2) | C23—C24 | 1.370 (4) |
Cl2—C3 | 1.729 (2) | C23—C22 | 1.384 (3) |
C12—N2 | 1.436 (2) | C25—C24 | 1.378 (3) |
C12—C13 | 1.371 (3) | C25—C28 | 1.507 (4) |
C12—C10 | 1.428 (3) | C6—H6 | 0.9300 |
Cl3—C19 | 1.744 (3) | C6—C5 | 1.374 (3) |
C2—H2 | 0.9300 | C15—H15A | 0.9700 |
C2—C1 | 1.389 (3) | C15—H15B | 0.9700 |
C2—C3 | 1.379 (3) | C15—C16 | 1.505 (3) |
N1—C7 | 1.339 (3) | C16—C21 | 1.372 (3) |
N1—C11 | 1.337 (3) | C16—C17 | 1.373 (4) |
C4—C5 | 1.369 (3) | C20—H20 | 0.9300 |
C4—C3 | 1.381 (3) | C20—C21 | 1.373 (3) |
C4—Cl1 | 1.722 (2) | C20—C19 | 1.363 (4) |
C9—H9 | 0.9300 | C24—H24 | 0.9300 |
C9—C8 | 1.368 (3) | C28—H28C | 0.9600 |
C9—C10 | 1.397 (3) | C28—H28B | 0.9600 |
N3—H3 | 0.8600 | C28—H28A | 0.9600 |
N3—C14 | 1.329 (3) | C21—H21 | 0.9300 |
N3—C15 | 1.458 (3) | C5—H5 | 0.9300 |
C30—H30 | 0.9300 | C17—H17 | 0.9300 |
C30—C31 | 1.366 (3) | C17—C18 | 1.387 (4) |
C30—C29 | 1.382 (3) | C18—H18 | 0.9300 |
C33—H33 | 0.9300 | C18—C19 | 1.356 (4) |
C33—C34 | 1.363 (3) | C27—H27 | 0.9300 |
C33—C32 | 1.391 (3) | C27—C22 | 1.380 (3) |
C8—H8 | 0.9300 | C32—C35 | 1.495 (3) |
C8—C7 | 1.402 (3) | C10—C11 | 1.395 (3) |
C14—C13 | 1.489 (3) | C35—H35B | 0.9600 |
C14—O1 | 1.217 (3) | C35—H35A | 0.9600 |
C1—C6 | 1.385 (3) | C35—H35C | 0.9600 |
S3—N2—S2 | 120.73 (9) | C25—C28—H28C | 109.5 |
C12—N2—S3 | 119.03 (13) | C25—C28—H28B | 109.5 |
C12—N2—S2 | 117.31 (13) | C25—C28—H28A | 109.5 |
C12—C13—S1 | 111.82 (17) | O1—C14—N3 | 123.0 (2) |
C12—C13—C14 | 133.09 (19) | O1—C14—C13 | 119.3 (2) |
N2—S3—C29 | 107.55 (10) | C6—C1—C2 | 117.6 (2) |
N2—S2—C22 | 104.92 (10) | C6—C1—C7 | 123.4 (2) |
O3—S3—N2 | 105.25 (9) | C6—C5—H5 | 119.7 |
O3—S3—O2 | 120.47 (11) | C15—N3—H3 | 119.1 |
O3—S3—C29 | 110.55 (10) | H15A—C15—H15B | 108.0 |
C2—C1—C7 | 119.0 (2) | C16—C15—H15A | 109.4 |
C2—C3—Cl2 | 119.49 (19) | C16—C15—H15B | 109.4 |
C2—C3—C4 | 120.4 (2) | C16—C21—C20 | 122.0 (3) |
O4—S2—N2 | 107.64 (10) | C16—C21—H21 | 119.0 |
O4—S2—O5 | 120.70 (12) | C16—C17—H17 | 119.6 |
O4—S2—C22 | 110.32 (10) | C16—C17—C18 | 120.8 (3) |
N1—C7—C8 | 121.7 (2) | C20—C21—H21 | 119.0 |
N1—C7—C1 | 115.83 (18) | C20—C19—Cl3 | 119.1 (3) |
N1—C11—S1 | 122.14 (15) | C24—C23—H23 | 120.0 |
N1—C11—C10 | 126.0 (2) | C24—C23—C22 | 120.0 (2) |
C4—C5—C6 | 120.6 (3) | C24—C25—C26 | 118.6 (2) |
C4—C5—H5 | 119.7 | C24—C25—C28 | 119.7 (3) |
C4—C3—Cl2 | 120.05 (18) | H28C—C28—H28B | 109.5 |
C9—C8—H8 | 119.5 | H28C—C28—H28A | 109.5 |
C9—C8—C7 | 120.9 (2) | H28B—C28—H28A | 109.5 |
C9—C10—C12 | 132.10 (18) | C21—C16—C15 | 121.5 (2) |
N3—C14—C13 | 117.6 (2) | C21—C16—C17 | 117.9 (2) |
N3—C15—H15A | 109.4 | C21—C20—H20 | 120.7 |
N3—C15—H15B | 109.4 | C5—C4—C3 | 119.0 (2) |
N3—C15—C16 | 111.3 (2) | C5—C4—Cl1 | 119.0 (2) |
C30—C31—H31 | 119.3 | C5—C6—C1 | 121.4 (2) |
C30—C31—C32 | 121.3 (2) | C5—C6—H6 | 119.3 |
C30—C29—S3 | 120.35 (17) | C17—C16—C15 | 120.6 (2) |
C30—C29—C34 | 119.7 (2) | C17—C18—H18 | 120.4 |
C33—C34—H34 | 120.4 | C18—C17—H17 | 119.6 |
C33—C34—C29 | 119.3 (2) | C18—C19—Cl3 | 119.5 (3) |
C33—C32—C35 | 120.8 (2) | C18—C19—C20 | 121.4 (3) |
C8—C9—H9 | 120.8 | C27—C26—H26 | 119.3 |
C8—C9—C10 | 118.39 (19) | C27—C26—C25 | 121.3 (2) |
C8—C7—C1 | 122.5 (2) | C27—C22—S2 | 121.61 (18) |
O2—S3—N2 | 104.19 (9) | C27—C22—C23 | 120.0 (2) |
O2—S3—C29 | 107.97 (11) | C19—C20—H20 | 120.7 |
C14—N3—H3 | 119.1 | C19—C20—C21 | 118.6 (3) |
C14—N3—C15 | 121.7 (2) | C19—C18—C17 | 119.2 (3) |
C14—C13—S1 | 114.78 (15) | C19—C18—H18 | 120.4 |
C1—C2—H2 | 119.5 | C7—C8—H8 | 119.5 |
C1—C6—H6 | 119.3 | C29—C30—H30 | 119.9 |
C26—C25—C28 | 121.7 (2) | C29—C34—H34 | 120.4 |
C26—C27—H27 | 120.4 | C32—C33—H33 | 118.8 |
C26—C27—C22 | 119.2 (2) | C32—C31—H31 | 119.3 |
C13—S1—C11 | 91.48 (10) | C32—C35—H35B | 109.5 |
C13—C12—N2 | 123.7 (2) | C32—C35—H35A | 109.5 |
C13—C12—C10 | 113.50 (17) | C32—C35—H35C | 109.5 |
C31—C30—H30 | 119.9 | C10—C12—N2 | 122.67 (18) |
C31—C30—C29 | 120.2 (2) | C10—C9—H9 | 120.8 |
C31—C32—C33 | 117.2 (2) | C10—C11—S1 | 111.85 (16) |
C31—C32—C35 | 122.0 (2) | C11—N1—C7 | 116.45 (17) |
C34—C33—H33 | 118.8 | C11—C10—C12 | 111.33 (18) |
C34—C33—C32 | 122.3 (2) | C11—C10—C9 | 116.54 (19) |
C34—C29—S3 | 119.99 (18) | H35B—C35—H35A | 109.5 |
C23—C24—C25 | 120.8 (2) | H35B—C35—H35C | 109.5 |
C23—C24—H24 | 119.6 | H35A—C35—H35C | 109.5 |
C23—C22—S2 | 118.28 (17) | C22—C23—H23 | 120.0 |
O5—S2—N2 | 103.82 (9) | C22—C27—H27 | 120.4 |
O5—S2—C22 | 108.17 (12) | C3—C2—H2 | 119.5 |
C25—C26—H26 | 119.3 | C3—C2—C1 | 120.9 (2) |
C25—C24—H24 | 119.6 | C3—C4—Cl1 | 121.94 (19) |
C12—C10—C11—S1 | −1.8 (2) | C34—C33—C32—C35 | −179.3 (2) |
C12—C10—C11—N1 | −179.6 (2) | O5—S2—N2—S3 | −160.20 (13) |
N2—S3—C29—C30 | 86.4 (2) | O5—S2—N2—C12 | 0.2 (2) |
N2—S3—C29—C34 | −94.24 (19) | O5—S2—C22—C23 | −32.3 (2) |
N2—S2—C22—C23 | 78.0 (2) | O5—S2—C22—C27 | 144.55 (18) |
N2—S2—C22—C27 | −105.11 (18) | C25—C26—C27—C22 | −0.6 (3) |
N2—C12—C13—S1 | −177.84 (16) | O1—C14—C13—S1 | 35.1 (3) |
N2—C12—C13—C14 | −4.7 (4) | O1—C14—C13—C12 | −137.8 (3) |
N2—C12—C10—C9 | 0.7 (4) | C6—C1—C7—N1 | 176.8 (2) |
N2—C12—C10—C11 | 178.63 (18) | C6—C1—C7—C8 | −2.8 (3) |
O3—S3—N2—S2 | −32.14 (15) | C15—N3—C14—C13 | −177.6 (2) |
O3—S3—N2—C12 | 167.77 (16) | C15—N3—C14—O1 | 3.3 (4) |
O3—S3—C29—C30 | −159.17 (18) | C15—C16—C21—C20 | 178.9 (3) |
O3—S3—C29—C34 | 20.2 (2) | C15—C16—C17—C18 | −179.4 (3) |
C2—C1—C6—C5 | 1.5 (4) | C16—C17—C18—C19 | 0.9 (5) |
C2—C1—C7—N1 | −0.7 (3) | C24—C23—C22—S2 | 175.52 (19) |
C2—C1—C7—C8 | 179.8 (2) | C24—C23—C22—C27 | −1.4 (4) |
O4—S2—N2—S3 | −31.16 (16) | C28—C25—C24—C23 | −177.6 (2) |
O4—S2—N2—C12 | 129.26 (16) | C21—C16—C17—C18 | 1.4 (5) |
O4—S2—C22—C23 | −166.28 (18) | C21—C20—C19—Cl3 | −176.6 (2) |
O4—S2—C22—C27 | 10.6 (2) | C21—C20—C19—C18 | 2.3 (5) |
C9—C8—C7—N1 | −1.1 (3) | C5—C4—C3—Cl2 | −179.9 (2) |
C9—C8—C7—C1 | 178.5 (2) | C5—C4—C3—C2 | 2.3 (4) |
C9—C10—C11—S1 | 176.53 (16) | C17—C16—C21—C20 | −2.0 (4) |
C9—C10—C11—N1 | −1.3 (3) | C17—C18—C19—Cl3 | 176.1 (3) |
N3—C14—C13—S1 | −144.01 (18) | C17—C18—C19—C20 | −2.9 (5) |
N3—C14—C13—C12 | 43.0 (4) | C27—C26—C25—C24 | −1.1 (4) |
N3—C15—C16—C21 | −48.3 (3) | C27—C26—C25—C28 | 178.1 (2) |
N3—C15—C16—C17 | 132.5 (3) | C19—C20—C21—C16 | 0.1 (4) |
C30—C31—C32—C33 | −0.5 (3) | C7—N1—C11—S1 | −176.33 (16) |
C30—C31—C32—C35 | −179.8 (2) | C7—N1—C11—C10 | 1.3 (3) |
C33—C34—C29—S3 | −179.88 (19) | C7—C1—C6—C5 | −176.0 (2) |
C33—C34—C29—C30 | −0.5 (3) | C29—S3—N2—S2 | 85.76 (14) |
C8—C9—C10—C12 | 177.9 (2) | C29—S3—N2—C12 | −74.33 (18) |
C8—C9—C10—C11 | 0.1 (3) | C29—C30—C31—C32 | −0.9 (4) |
O2—S3—N2—S2 | −159.80 (12) | C32—C33—C34—C29 | −0.9 (4) |
O2—S3—N2—C12 | 40.11 (19) | C10—C12—N2—S3 | 91.2 (2) |
O2—S3—C29—C30 | −25.5 (2) | C10—C12—N2—S2 | −69.5 (2) |
O2—S3—C29—C34 | 153.87 (18) | C10—C12—C13—S1 | −1.1 (2) |
C14—N3—C15—C16 | 161.2 (2) | C10—C12—C13—C14 | 172.0 (2) |
C1—C2—C3—Cl2 | −177.56 (18) | C10—C9—C8—C7 | 1.0 (3) |
C1—C2—C3—C4 | 0.2 (4) | C11—S1—C13—C12 | 0.07 (17) |
C1—C6—C5—C4 | 1.0 (4) | C11—S1—C13—C14 | −174.39 (18) |
C26—C25—C24—C23 | 1.6 (4) | C11—N1—C7—C8 | −0.1 (3) |
C26—C27—C22—S2 | −174.91 (18) | C11—N1—C7—C1 | −179.62 (19) |
C26—C27—C22—C23 | 1.9 (3) | C22—S2—N2—S3 | 86.35 (14) |
C13—S1—C11—N1 | 178.89 (19) | C22—S2—N2—C12 | −113.23 (17) |
C13—S1—C11—C10 | 0.99 (17) | C22—C23—C24—C25 | −0.4 (4) |
C13—C12—N2—S3 | −92.3 (2) | C3—C2—C1—C6 | −2.1 (3) |
C13—C12—N2—S2 | 106.9 (2) | C3—C2—C1—C7 | 175.5 (2) |
C13—C12—C10—C9 | −176.1 (2) | C3—C4—C5—C6 | −2.9 (4) |
C13—C12—C10—C11 | 1.8 (3) | Cl1—C4—C5—C6 | 175.7 (2) |
C31—C30—C29—S3 | −179.22 (18) | Cl1—C4—C3—Cl2 | 1.5 (3) |
C31—C30—C29—C34 | 1.4 (3) | Cl1—C4—C3—C2 | −176.26 (18) |
C34—C33—C32—C31 | 1.4 (4) |
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.86 | 2.11 | 2.945 (3) | 162 |
C34—H34···S1i | 0.93 | 2.79 | 3.714 (2) | 172 |
Symmetry code: (i) x, y+1, z. |
Experimental details
Crystal data | |
Chemical formula | C35H26Cl3N3O5S3 |
Mr | 771.15 |
Crystal system, space group | Monoclinic, P21/c |
Temperature (K) | 294 |
a, b, c (Å) | 25.8238 (8), 9.1634 (2), 14.8366 (5) |
β (°) | 102.314 (3) |
V (Å3) | 3430.07 (17) |
Z | 4 |
Radiation type | Mo Kα |
µ (mm−1) | 0.50 |
Crystal size (mm) | 0.36 × 0.28 × 0.16 |
Data collection | |
Diffractometer | Oxford Diffraction Xcalibur Eos diffractometer |
Absorption correction | Multi-scan (CrysAlis PRO; Oxford Diffraction, 2010) |
Tmin, Tmax | 0.695, 1.0 |
No. of measured, independent and observed [I > 2σ(I)] reflections | 14766, 7014, 4515 |
Rint | 0.024 |
(sin θ/λ)max (Å−1) | 0.625 |
Refinement | |
R[F2 > 2σ(F2)], wR(F2), S | 0.043, 0.105, 1.03 |
No. of reflections | 7014 |
No. of parameters | 444 |
H-atom treatment | H-atom parameters constrained |
Δρmax, Δρmin (e Å−3) | 0.28, −0.35 |
Computer programs: CrysAlis PRO (Oxford Diffraction, 2010), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), OLEX2 (Dolomanov et al., 2009), SHELXTL (Sheldrick, 2008) and OLEX2 (Dolomanov et al., 2009).
D—H···A | D—H | H···A | D···A | D—H···A |
N3—H3···O2 | 0.86 | 2.11 | 2.945 (3) | 162 |
C34—H34···S1i | 0.93 | 2.79 | 3.714 (2) | 172 |
Symmetry code: (i) x, y+1, z. |
References
Dolomanov, O. V., Bourhis, L. J., Gildea, R. J., Howard, J. A. K. & Puschmann, H. (2009). J. Appl. Cryst. 42, 339–341. Web of Science CrossRef CAS IUCr Journals Google Scholar
Litvinov, V. P., Dotsenko, V. V. & Krivokolysko, S. G. (2005). Russ. Chem. Bull. 54, 864–904. Web of Science CrossRef CAS 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
This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.
Thieno[2,3-b]pyridine derivatives are of great importance owing to their wide biological properties (Litvinov et al., 2005). The title compound is one of the key intermediates in our synthetic investigations of anticancer drugs. We report here its crystal structure.
In the tile compound (Fig. 1), the thieno[2,3-b]pyridine ring system is approximately planar (maximum deviation 0.048 (2) Å for atom C8) and forms a dihedral angle of 3.89 (6)° with the attached benzene ring. The molecular conformation is stabilized by an intramolecular N—H···O hydrogen bond (Table 1). In the crystal structure (Fig. 2), the molecules are linked into chains parallel to the [100] direction by C···H···O hydrogen bonds.