3-[Bis(p-tolyl­sulfon­yl)amino]-N-(4-chloro­benz­yl)-6-(3,4-dichloro­phen­yl)thieno[2,3-b]pyridine-2-carboxamide

He, H.-Y.; Li, H.-Z.; Yang, L.

doi:10.1107/S160053681100290X

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o499

doi:10.1107/S160053681100290X

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3-[Bis(p-tolylsulfonyl)amino]-N-(4-chlorobenzyl)-6-(3,4-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide

Hai-Yun He,^a Hong-Ze Li ^b and Li Yang ^a ^*

^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

(Received 10 January 2011; accepted 21 January 2011; online 26 January 2011)

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

C₃₅H₂₆Cl₃N₃O₅S₃
M_r = 771.15
Monoclinic, P 2₁ /c
a = 25.8238 (8) Å
b = 9.1634 (2) Å
c = 14.8366 (5) Å
β = 102.314 (3)°
V = 3430.07 (17) Å³
Z = 4
Mo Kα radiation
μ = 0.50 mm⁻¹
T = 294 K
0.36 × 0.28 × 0.16 mm

Data collection

Oxford Diffraction Xcalibur Eos diffractometer
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) T_min = 0.695, T_max = 1.0
14766 measured reflections
7014 independent reflections
4515 reflections with I > 2σ(I)
R_int = 0.024

Refinement

R[F² > 2σ(F²)] = 0.043
wR(F²) = 0.105
S = 1.03
7014 reflections
444 parameters
H-atom parameters constrained
Δρ_max = 0.28 e Å⁻³
Δρ_min = −0.35 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

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.

Data collection: CrysAlis PRO (Oxford Diffraction, 2010 $[Oxford Diffraction (2010). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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: OLEX2 (Dolomanov et al., 2009 ); software used to prepare material for publication: SHELXTL (Sheldrick, 2008) and OLEX2.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053681100290X/rz2547sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053681100290X/rz2547Isup2.hkl

checkCIF report

Comment top

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.

Related literature top

For general background to the biological properties of thieno[2,3-b]pyridine derivatives, see: Litvinov et al. (2005).

Experimental top

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 eluent. 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.

Computing details top

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

Figures top

	Fig. 1. The molecular structure of the title compound, with displacement ellipsoids drawn at the 30% probability level. The intramolecular N—H···O hydrogen bond is shown as a dashed line.
	Fig. 2. Packing diagram of the title compound viewed along the b axis.

3-[Bis(p-tolylsulfonyl)amino]-N-(4-chlorobenzyl)-6-(3,4- dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide top

Crystal data top

C₃₅H₂₆Cl₃N₃O₅S₃	F(000) = 1584
M_r = 771.15	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	7014 independent reflections
Radiation source: fine-focus sealed tube	4515 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.024
Detector resolution: 16.0874 pixels mm^-1	θ_max = 26.4°, θ_min = 3.1°
ω scans	h = −28→32
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	k = −10→11
T_min = 0.695, T_max = 1.0	l = −18→9
14766 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)] = 0.043	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.0514P)²] where P = (F_o² + 2F_c²)/3
7014 reflections	(Δ/σ)_max = 0.001
444 parameters	Δρ_max = 0.28 e Å⁻³
0 restraints	Δρ_min = −0.35 e Å⁻³

Crystal data top

C₃₅H₂₆Cl₃N₃O₅S₃	V = 3430.07 (17) Å³
M_r = 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)°

Data collection top

Oxford Diffraction Xcalibur Eos diffractometer	7014 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2010)	4515 reflections with I > 2σ(I)
T_min = 0.695, T_max = 1.0	R_int = 0.024
14766 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.043	0 restraints
wR(F²) = 0.105	H-atom parameters constrained
S = 1.03	Δρ_max = 0.28 e Å⁻³
7014 reflections	Δρ_min = −0.35 e Å⁻³
444 parameters

Special details top

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
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)

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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
M_r	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)
T_min, T_max	0.695, 1.0
No. of measured, independent and observed [I > 2σ(I)] reflections	14766, 7014, 4515
R_int	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
Δρ_max, Δρ_min (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).

Hydrogen-bond geometry (Å, º) top

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

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Volume 67| Part 2| February 2011| Page o499

doi:10.1107/S160053681100290X

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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

3-[Bis(p-tolyl­sulfon­yl)amino]-N-(4-chloro­benz­yl)-6-(3,4-di­chloro­phen­yl)thieno[2,3-b]pyridine-2-carboxamide

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

References

organic compounds

3-[Bis(p-tolylsulfonyl)amino]-N-(4-chlorobenzyl)-6-(3,4-dichlorophenyl)thieno[2,3-b]pyridine-2-carboxamide