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

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ISSN: 2056-9890

Ethyl 4-[({[(6-chloro­pyridin-3-yl)meth­yl](meth­yl)amino}(4-fluoro­anilino)­methyl­­idene)amino]-3-phenyl-2-sulfanyl­­idene-2,3-di­hydro-1,3-thia­zole-5-carboxyl­ate

aHubei Biopesticide Engineering Research Center, Hubei Academy of Agricultural Science, Wuhan 430064, People's Republic of China, and bKey Laboratory of Pesticide & Chemical Biology of the Ministry of Education, Central China Normal University, Wuhan 430079, People's Republic of China.
*Correspondence e-mail: ly.liang8@gmail.com

(Received 19 May 2012; accepted 11 June 2012; online 30 June 2012)

In the title compound, C26H23ClFN5O2S2, the mean plane of the guanidine fragment makes dihedral angles of 58.94 (13), 78.37 (17) and 50.76 (15)°, respectively, with the attached thia­zole, pyridine and phenyl rings. The crystal structure features N—H⋯S and C—H⋯O hydrogen bonds and weak ππ stacking inter­actions [centroid–centroid separation = 3.7702 (17) Å]. The terminal methyl group of the eth­oxy­carbonyl group is disordered over two orientations in a 0.836 (10):0.164 (10) ratio.

Related literature

For further synthetic details and background to thia­zolo­pyrimidines, see: Liang et al. (2007[Liang, Y., Fan, S., Mo, W. Y. & He, H. W. (2007). J. Fluorine Chem. 128, 879-884.]).

[Scheme 1]

Experimental

Crystal data
  • C26H23ClFN5O2S2

  • Mr = 556.06

  • Monoclinic, P 21 /c

  • a = 9.6931 (5) Å

  • b = 24.5636 (12) Å

  • c = 11.7095 (6) Å

  • β = 103.745 (1)°

  • V = 2708.2 (2) Å3

  • Z = 4

  • Mo Kα radiation

  • μ = 0.34 mm−1

  • T = 298 K

  • 0.20 × 0.10 × 0.06 mm

Data collection
  • Bruker SMART APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2001[Sheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.]) Tmin = 0.936, Tmax = 0.980

  • 23442 measured reflections

  • 5326 independent reflections

  • 3569 reflections with I > 2σ(I)

  • Rint = 0.097

Refinement
  • R[F2 > 2σ(F2)] = 0.061

  • wR(F2) = 0.172

  • S = 1.00

  • 5326 reflections

  • 350 parameters

  • 23 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.40 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A DA D—H⋯A
N3—H3A⋯S2i 0.86 (3) 2.65 (3) 3.443 (3) 153 (3)
C7—H7B⋯O1ii 0.96 2.51 3.282 (4) 138
Symmetry codes: (i) x-1, y, z; (ii) -x, -y+1, -z+2.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: SHELXTL (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: SHELXTL.

Supporting information


Comment top

Recently, we have developed a new and versatile annulation process, which proceeded smoothly under mild conditions via a tandem aza-wittig and cyclization reaction (Liang et al., 2007), to synthesize new thiazolo[4,5-d]pyrimidine derivatives with possible herbicidal activities. In this paper, we report the structure of the intermediate guanidine derivative, (I) (Fig. 1).

In the molecule of the title compound, (I), the mean plane of the guanidine system is nearly coplannar. The three aryl groups are roughly twisted from the central guanidine system, the dihedral being 58.94 (13)°(thiazole), 78.37 (17)° (pyridine) and 50.76 (15)° (p-fluorophenyl) respectively, and the thiazole ring is nearly planar with the ethyloxyacyl group. The crystal packing is stabilized by C—H···O and C—H···S hydrogen bonds (Table 1) and weak π-π stacking interactions [Cg1···Cg3i = 3.7702 (17) Å; symmetry code: (i) x, y, z]. The atom C26 was disorder.

Related literature top

For further synthetic details and background to thiazolopyrimidines, see: Liang et al. (2007).

Experimental top

To a solution of the iminophosphorane (1 mmol) in dry CH2Cl2(15 ml) was added 4-fluorophenyl isocyanate (1.1 mmol) under an N2 atmosphere at room tempreture. After the reaction mixture was allowed to stand for 5–12 h, the solvent was removed under reduced pressure, then Et2O and petroleum ether were added to precipitate the side product triphenylphosphine oxide which was then removed by filtration. Subsequent removal of the solvent gave the corresponding carbodiimide, which was used directly without further purification. To a solution of the carbodiimide in ethanol(15 ml) was added 1-(6-chloropyridin-3-yl)-N-methyl methanamine (1.1 mmol) and a catalytic amount of sodium ethoxide in ethanol. After the mixture had been stirred for 4 h at 303 K, the solution was concentrated and the residue was recrystallized from CH3CN solution to give colorless blocks of the title compound, (I), after one week.

Refinement top

All H-atoms bound to carbon were refined using a riding model with d(C—H) = 0.93 Å, Uiso=1.2Ueq (C) for aromatic 0.98 Å, Uiso = 1.2Ueq (C) for CH 0.96 Å, Uiso = 1.5Ueq (C) for CH3 H atoms.

Structure description top

Recently, we have developed a new and versatile annulation process, which proceeded smoothly under mild conditions via a tandem aza-wittig and cyclization reaction (Liang et al., 2007), to synthesize new thiazolo[4,5-d]pyrimidine derivatives with possible herbicidal activities. In this paper, we report the structure of the intermediate guanidine derivative, (I) (Fig. 1).

In the molecule of the title compound, (I), the mean plane of the guanidine system is nearly coplannar. The three aryl groups are roughly twisted from the central guanidine system, the dihedral being 58.94 (13)°(thiazole), 78.37 (17)° (pyridine) and 50.76 (15)° (p-fluorophenyl) respectively, and the thiazole ring is nearly planar with the ethyloxyacyl group. The crystal packing is stabilized by C—H···O and C—H···S hydrogen bonds (Table 1) and weak π-π stacking interactions [Cg1···Cg3i = 3.7702 (17) Å; symmetry code: (i) x, y, z]. The atom C26 was disorder.

For further synthetic details and background to thiazolopyrimidines, see: Liang et al. (2007).

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top
[Figure 1] Fig. 1. The structure of (I), showing 50% probability displacement ellipsoids.
[Figure 2] Fig. 2. Crystal Packing diagram of (I). Hydrogen bonds are shown as dashed lines.
Ethyl 4-[({[(6-chloropyridin-3-yl)methyl](methyl)amino}(4- fluoroanilino)methylidene)amino]-3-phenyl-2-sulfanylidene- 2,3-dihydro-1,3-thiazole-5-carboxylate top
Crystal data top
C26H23ClFN5O2S2F(000) = 1152
Mr = 556.06Dx = 1.364 Mg m3
Monoclinic, P21/cMo Kα radiation, λ = 0.71073 Å
a = 9.6931 (5) ÅCell parameters from 4840 reflections
b = 24.5636 (12) Åθ = 2.3–25.7°
c = 11.7095 (6) ŵ = 0.34 mm1
β = 103.745 (1)°T = 298 K
V = 2708.2 (2) Å3Needle, colourless
Z = 40.20 × 0.10 × 0.06 mm
Data collection top
Bruker SMART APEX CCD
diffractometer
5326 independent reflections
Radiation source: fine-focus sealed tube3569 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.097
φ and ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
h = 1111
Tmin = 0.936, Tmax = 0.980k = 3027
23442 measured reflectionsl = 1414
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.061Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 1.00 w = 1/[σ2(Fo2) + (0.0958P)2]
where P = (Fo2 + 2Fc2)/3
5326 reflections(Δ/σ)max < 0.001
350 parametersΔρmax = 0.50 e Å3
23 restraintsΔρmin = 0.40 e Å3
Crystal data top
C26H23ClFN5O2S2V = 2708.2 (2) Å3
Mr = 556.06Z = 4
Monoclinic, P21/cMo Kα radiation
a = 9.6931 (5) ŵ = 0.34 mm1
b = 24.5636 (12) ÅT = 298 K
c = 11.7095 (6) Å0.20 × 0.10 × 0.06 mm
β = 103.745 (1)°
Data collection top
Bruker SMART APEX CCD
diffractometer
5326 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2001)
3569 reflections with I > 2σ(I)
Tmin = 0.936, Tmax = 0.980Rint = 0.097
23442 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.06123 restraints
wR(F2) = 0.172H atoms treated by a mixture of independent and constrained refinement
S = 1.00Δρmax = 0.50 e Å3
5326 reflectionsΔρmin = 0.40 e Å3
350 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
xyzUiso*/UeqOcc. (<1)
C10.2452 (4)0.72915 (14)0.9071 (4)0.0648 (10)
C20.2408 (5)0.69171 (16)0.8193 (3)0.0750 (11)
H20.25680.70170.74700.090*
C30.2115 (5)0.63856 (14)0.8432 (3)0.0682 (10)
H30.20790.61190.78620.082*
C40.1875 (3)0.62471 (12)0.9506 (2)0.0441 (7)
C50.1929 (4)0.66619 (14)1.0298 (3)0.0652 (10)
H50.17530.65741.10230.078*
C60.1574 (3)0.56709 (12)0.9822 (3)0.0470 (8)
H6A0.24670.54771.00650.056*
H6B0.11370.56791.04860.056*
C70.0833 (3)0.55378 (12)0.8587 (3)0.0499 (8)
H7A0.11470.56060.77590.075*
H7B0.09360.58630.90140.075*
H7C0.13960.52520.88060.075*
C80.1212 (3)0.50286 (11)0.8189 (2)0.0386 (7)
C90.0566 (3)0.44719 (12)0.6372 (2)0.0411 (7)
C100.0089 (3)0.39778 (13)0.6085 (3)0.0515 (8)
H100.07000.38410.65190.062*
C110.0165 (4)0.36822 (14)0.5142 (3)0.0620 (9)
H110.02940.33530.49210.074*
C120.1103 (4)0.38872 (15)0.4550 (3)0.0602 (9)
C130.1761 (4)0.43763 (14)0.4815 (3)0.0541 (8)
H130.23970.45040.43950.065*
C140.1462 (3)0.46790 (13)0.5720 (2)0.0452 (7)
H140.18640.50220.58910.054*
C150.3352 (3)0.45864 (12)0.8084 (2)0.0383 (7)
C160.3268 (3)0.40313 (12)0.8165 (2)0.0436 (7)
C170.5342 (3)0.43200 (13)0.7403 (2)0.0434 (7)
C180.4900 (3)0.53030 (12)0.7543 (2)0.0408 (7)
C190.4673 (4)0.55250 (14)0.6438 (3)0.0537 (8)
H190.43180.53110.57780.064*
C200.4975 (4)0.60657 (15)0.6316 (4)0.0699 (10)
H200.48170.62190.55700.084*
C210.5505 (4)0.63778 (15)0.7284 (4)0.0742 (11)
H210.57150.67430.71980.089*
C220.5730 (4)0.61527 (15)0.8390 (4)0.0724 (11)
H220.60860.63680.90480.087*
C230.5434 (4)0.56148 (13)0.8531 (3)0.0552 (8)
H230.55910.54620.92780.066*
C240.2234 (4)0.37141 (13)0.8606 (3)0.0521 (8)
O20.2516 (3)0.31823 (10)0.8546 (3)0.0856 (9)
C250.1581 (6)0.27977 (19)0.8952 (5)0.1149 (18)
H25A0.14020.24860.84290.138*0.836 (10)
H25B0.06790.29710.89380.138*0.836 (10)
H25C0.11390.29720.95170.138*0.164 (10)
H25D0.21230.24880.93320.138*0.164 (10)
C260.2260 (11)0.2612 (4)1.0182 (5)0.212 (5)0.836 (10)
H26A0.32460.25341.02440.317*0.836 (10)
H26B0.17910.22891.03570.317*0.836 (10)
H26C0.21750.28931.07300.317*0.836 (10)
C26'0.035 (2)0.2639 (11)0.7926 (17)0.117 (16)0.164 (10)
H26D0.03060.29370.77430.175*0.164 (10)
H26E0.01270.23260.81400.175*0.164 (10)
H26F0.07110.25540.72510.175*0.164 (10)
Cl10.28382 (14)0.79686 (4)0.88166 (13)0.0998 (4)
F10.1395 (3)0.35853 (9)0.36600 (19)0.0894 (8)
N10.2212 (4)0.71815 (12)1.0114 (3)0.0754 (9)
N20.0652 (3)0.53743 (10)0.8866 (2)0.0424 (6)
N30.0259 (3)0.47731 (11)0.7322 (2)0.0455 (6)
N40.2593 (2)0.50043 (10)0.8382 (2)0.0430 (6)
N50.4550 (2)0.47396 (10)0.76883 (18)0.0393 (6)
O10.1278 (3)0.38916 (9)0.8991 (2)0.0607 (6)
S10.46244 (9)0.37121 (3)0.76844 (7)0.0518 (3)
S20.67662 (9)0.43702 (4)0.68492 (7)0.0546 (3)
H3A0.059 (4)0.4739 (14)0.742 (3)0.066*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
C10.063 (2)0.0369 (19)0.099 (3)0.0057 (16)0.029 (2)0.0006 (19)
C20.104 (3)0.050 (2)0.083 (3)0.002 (2)0.048 (2)0.0081 (19)
C30.101 (3)0.045 (2)0.069 (2)0.0017 (19)0.039 (2)0.0037 (17)
C40.0437 (18)0.0404 (17)0.0499 (16)0.0029 (14)0.0146 (13)0.0015 (14)
C50.088 (3)0.049 (2)0.064 (2)0.0016 (19)0.029 (2)0.0085 (17)
C60.056 (2)0.0412 (18)0.0461 (16)0.0055 (14)0.0157 (14)0.0039 (13)
C70.051 (2)0.0468 (19)0.0588 (18)0.0063 (15)0.0255 (15)0.0028 (15)
C80.0443 (18)0.0302 (15)0.0449 (15)0.0002 (13)0.0180 (13)0.0039 (12)
C90.0364 (16)0.0434 (18)0.0443 (15)0.0054 (13)0.0112 (13)0.0021 (13)
C100.054 (2)0.047 (2)0.0597 (19)0.0017 (15)0.0237 (16)0.0079 (15)
C110.078 (3)0.046 (2)0.066 (2)0.0057 (18)0.0252 (19)0.0135 (17)
C120.079 (3)0.056 (2)0.0527 (18)0.0077 (19)0.0290 (18)0.0054 (16)
C130.060 (2)0.058 (2)0.0489 (18)0.0070 (17)0.0218 (15)0.0046 (16)
C140.0454 (18)0.0449 (18)0.0448 (16)0.0003 (14)0.0097 (13)0.0005 (13)
C150.0347 (16)0.0417 (17)0.0397 (14)0.0008 (13)0.0111 (12)0.0006 (12)
C160.0415 (17)0.0391 (18)0.0531 (17)0.0044 (13)0.0170 (14)0.0012 (13)
C170.0366 (17)0.0481 (19)0.0443 (16)0.0017 (13)0.0074 (13)0.0041 (13)
C180.0306 (15)0.0418 (17)0.0506 (16)0.0011 (13)0.0108 (12)0.0004 (13)
C190.056 (2)0.053 (2)0.0541 (19)0.0043 (16)0.0184 (15)0.0009 (15)
C200.075 (3)0.059 (2)0.078 (2)0.008 (2)0.023 (2)0.018 (2)
C210.073 (3)0.044 (2)0.109 (3)0.0100 (19)0.028 (2)0.010 (2)
C220.073 (3)0.053 (2)0.083 (3)0.0132 (19)0.003 (2)0.012 (2)
C230.056 (2)0.049 (2)0.0568 (19)0.0060 (16)0.0055 (16)0.0004 (15)
C240.054 (2)0.0437 (19)0.0623 (19)0.0003 (16)0.0217 (16)0.0017 (15)
O20.091 (2)0.0373 (14)0.146 (2)0.0028 (13)0.0641 (18)0.0081 (15)
C250.124 (4)0.053 (3)0.191 (5)0.012 (3)0.083 (4)0.011 (3)
C260.273 (9)0.201 (8)0.157 (7)0.137 (7)0.041 (6)0.024 (6)
C26'0.17 (4)0.070 (19)0.09 (2)0.04 (2)0.01 (2)0.040 (15)
Cl10.1111 (10)0.0425 (6)0.1552 (11)0.0098 (6)0.0502 (8)0.0038 (6)
F10.136 (2)0.0720 (15)0.0778 (14)0.0048 (14)0.0615 (15)0.0188 (12)
N10.100 (3)0.0414 (18)0.087 (2)0.0051 (17)0.0263 (19)0.0152 (16)
N20.0427 (15)0.0378 (14)0.0498 (13)0.0029 (11)0.0170 (11)0.0048 (11)
N30.0374 (15)0.0499 (16)0.0529 (14)0.0005 (12)0.0179 (12)0.0109 (12)
N40.0394 (15)0.0388 (14)0.0532 (14)0.0004 (11)0.0155 (11)0.0074 (11)
N50.0359 (13)0.0388 (14)0.0428 (12)0.0002 (10)0.0086 (10)0.0020 (10)
O10.0646 (16)0.0559 (15)0.0730 (15)0.0033 (12)0.0391 (13)0.0018 (11)
S10.0492 (5)0.0393 (5)0.0713 (5)0.0058 (4)0.0232 (4)0.0017 (4)
S20.0431 (5)0.0595 (6)0.0667 (5)0.0006 (4)0.0237 (4)0.0088 (4)
Geometric parameters (Å, º) top
C1—N11.325 (5)C15—N51.401 (3)
C1—C21.372 (5)C16—C241.457 (4)
C1—Cl11.746 (4)C16—S11.736 (3)
C2—C31.379 (5)C17—N51.373 (4)
C2—H20.9300C17—S21.664 (3)
C3—C41.376 (4)C17—S11.712 (3)
C3—H30.9300C18—C191.373 (4)
C4—C51.370 (4)C18—C231.381 (4)
C4—C61.509 (4)C18—N51.444 (4)
C5—N11.334 (4)C19—C201.375 (5)
C5—H50.9300C19—H190.9300
C6—N21.452 (4)C20—C211.364 (5)
C6—H6A0.9700C20—H200.9300
C6—H6B0.9700C21—C221.377 (5)
C7—N21.455 (4)C21—H210.9300
C7—H7A0.9600C22—C231.370 (5)
C7—H7B0.9600C22—H220.9300
C7—H7C0.9600C23—H230.9300
C8—N41.304 (4)C24—O11.204 (4)
C8—N31.354 (4)C24—O21.340 (4)
C8—N21.359 (3)O2—C251.464 (4)
C9—C101.374 (4)C25—C261.506 (6)
C9—C141.383 (4)C25—C26'1.529 (9)
C9—N31.424 (4)C25—H25A0.9700
C10—C111.391 (4)C25—H25B0.9700
C10—H100.9300C25—H25C0.9700
C11—C121.364 (5)C25—H25D0.9700
C11—H110.9300C26—H26A0.9600
C12—C131.361 (5)C26—H26B0.9600
C12—F11.363 (3)C26—H26C0.9600
C13—C141.381 (4)C26'—H26D0.9600
C13—H130.9300C26'—H26E0.9600
C14—H140.9300C26'—H26F0.9600
C15—N41.356 (3)N3—H3A0.86 (3)
C15—C161.371 (4)
N1—C1—C2124.9 (3)C19—C20—H20119.9
N1—C1—Cl1116.3 (3)C20—C21—C22120.0 (3)
C2—C1—Cl1118.7 (3)C20—C21—H21120.0
C1—C2—C3117.0 (3)C22—C21—H21120.0
C1—C2—H2121.5C23—C22—C21120.6 (3)
C3—C2—H2121.5C23—C22—H22119.7
C4—C3—C2120.5 (3)C21—C22—H22119.7
C4—C3—H3119.8C22—C23—C18118.8 (3)
C2—C3—H3119.8C22—C23—H23120.6
C5—C4—C3116.6 (3)C18—C23—H23120.6
C5—C4—C6120.7 (3)O1—C24—O2123.9 (3)
C3—C4—C6122.7 (3)O1—C24—C16126.4 (3)
N1—C5—C4125.3 (3)O2—C24—C16109.7 (3)
N1—C5—H5117.3C24—O2—C25117.5 (3)
C4—C5—H5117.3O2—C25—C26110.1 (4)
N2—C6—C4113.7 (2)O2—C25—C26'109.7 (6)
N2—C6—H6A108.8C26—C25—C26'139.1 (7)
C4—C6—H6A108.8O2—C25—H25A109.6
N2—C6—H6B108.8C26—C25—H25A109.6
C4—C6—H6B108.8C26'—C25—H25A46.7
H6A—C6—H6B107.7O2—C25—H25B109.6
N2—C7—H7A109.5C26—C25—H25B109.6
N2—C7—H7B109.5C26'—C25—H25B64.3
H7A—C7—H7B109.5H25A—C25—H25B108.2
N2—C7—H7C109.5O2—C25—H25C110.2
H7A—C7—H7C109.5C26—C25—H25C69.1
H7B—C7—H7C109.5C26'—C25—H25C105.1
N4—C8—N3126.7 (3)H25A—C25—H25C137.6
N4—C8—N2117.6 (3)H25B—C25—H25C43.4
N3—C8—N2115.5 (3)O2—C25—H25D110.2
C10—C9—C14120.3 (3)C26—C25—H25D42.0
C10—C9—N3118.7 (3)C26'—C25—H25D113.4
C14—C9—N3121.0 (3)H25A—C25—H25D70.5
C9—C10—C11119.8 (3)H25B—C25—H25D137.7
C9—C10—H10120.1H25C—C25—H25D108.1
C11—C10—H10120.1C25—C26—H25C38.0
C12—C11—C10118.4 (3)C25—C26—H25D39.6
C12—C11—H11120.8H25C—C26—H25D75.8
C10—C11—H11120.8C25—C26—H26A109.5
C13—C12—F1118.9 (3)H25C—C26—H26A139.1
C13—C12—C11122.9 (3)H25D—C26—H26A84.9
F1—C12—C11118.2 (3)C25—C26—H26B109.5
C12—C13—C14118.5 (3)H25C—C26—H26B106.4
C12—C13—H13120.7H25D—C26—H26B90.2
C14—C13—H13120.7C25—C26—H26C109.5
C13—C14—C9120.0 (3)H25C—C26—H26C75.5
C13—C14—H14120.0H25D—C26—H26C148.8
C9—C14—H14120.0C25—C26'—H26D109.5
N4—C15—C16133.7 (3)C25—C26'—H26E109.5
N4—C15—N5115.2 (3)H26D—C26'—H26E109.5
C16—C15—N5111.0 (2)C25—C26'—H26F109.5
C15—C16—C24127.9 (3)H26D—C26'—H26F109.5
C15—C16—S1111.4 (2)H26E—C26'—H26F109.5
C24—C16—S1120.7 (2)C1—N1—C5115.6 (3)
N5—C17—S2127.1 (2)C8—N2—C6120.3 (2)
N5—C17—S1109.4 (2)C8—N2—C7123.6 (2)
S2—C17—S1123.53 (18)C6—N2—C7115.4 (2)
C19—C18—C23120.9 (3)C8—N3—C9126.4 (3)
C19—C18—N5120.1 (3)C8—N3—H3A116 (2)
C23—C18—N5119.0 (3)C9—N3—H3A116 (2)
C18—C19—C20119.4 (3)C8—N4—C15125.9 (2)
C18—C19—H19120.3C17—N5—C15115.7 (2)
C20—C19—H19120.3C17—N5—C18122.0 (2)
C21—C20—C19120.3 (3)C15—N5—C18122.2 (2)
C21—C20—H20119.9C17—S1—C1692.42 (14)
N1—C1—C2—C31.2 (7)C16—C24—O2—C25179.9 (3)
Cl1—C1—C2—C3179.3 (3)C24—O2—C25—C2699.3 (6)
C1—C2—C3—C40.3 (6)C24—O2—C25—C26'90.2 (15)
C2—C3—C4—C50.7 (6)C2—C1—N1—C50.9 (6)
C2—C3—C4—C6178.9 (4)Cl1—C1—N1—C5179.5 (3)
C3—C4—C5—N11.0 (6)C4—C5—N1—C10.2 (6)
C6—C4—C5—N1178.7 (4)N4—C8—N2—C64.5 (4)
C5—C4—C6—N2140.5 (3)N3—C8—N2—C6180.0 (2)
C3—C4—C6—N239.9 (4)N4—C8—N2—C7165.5 (3)
C14—C9—C10—C110.8 (5)N3—C8—N2—C79.9 (4)
N3—C9—C10—C11178.3 (3)C4—C6—N2—C898.3 (3)
C9—C10—C11—C122.1 (5)C4—C6—N2—C772.6 (3)
C10—C11—C12—C132.4 (6)N4—C8—N3—C97.1 (5)
C10—C11—C12—F1177.2 (3)N2—C8—N3—C9167.9 (3)
F1—C12—C13—C14179.8 (3)C10—C9—N3—C8135.3 (3)
C11—C12—C13—C140.2 (5)C14—C9—N3—C847.2 (4)
C12—C13—C14—C93.1 (5)N3—C8—N4—C1526.7 (4)
C10—C9—C14—C133.4 (5)N2—C8—N4—C15158.4 (3)
N3—C9—C14—C13179.1 (3)C16—C15—N4—C843.7 (5)
N4—C15—C16—C241.6 (5)N5—C15—N4—C8142.1 (3)
N5—C15—C16—C24176.0 (3)S2—C17—N5—C15176.7 (2)
N4—C15—C16—S1177.2 (3)S1—C17—N5—C152.4 (3)
N5—C15—C16—S12.8 (3)S2—C17—N5—C180.8 (4)
C23—C18—C19—C200.3 (5)S1—C17—N5—C18179.93 (19)
N5—C18—C19—C20178.2 (3)N4—C15—N5—C17178.9 (2)
C18—C19—C20—C210.5 (6)C16—C15—N5—C173.4 (3)
C19—C20—C21—C220.5 (6)N4—C15—N5—C183.5 (4)
C20—C21—C22—C230.4 (6)C16—C15—N5—C18179.0 (2)
C21—C22—C23—C180.3 (6)C19—C18—N5—C1772.3 (4)
C19—C18—C23—C220.3 (5)C23—C18—N5—C17109.1 (3)
N5—C18—C23—C22178.3 (3)C19—C18—N5—C15105.2 (3)
C15—C16—C24—O10.9 (6)C23—C18—N5—C1573.5 (4)
S1—C16—C24—O1177.8 (3)N5—C17—S1—C160.6 (2)
C15—C16—C24—O2179.7 (3)S2—C17—S1—C16178.58 (19)
S1—C16—C24—O21.0 (4)C15—C16—S1—C171.3 (2)
O1—C24—O2—C251.3 (5)C24—C16—S1—C17177.5 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···S2i0.86 (3)2.65 (3)3.443 (3)153 (3)
C7—H7B···O1ii0.962.513.282 (4)138
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+2.

Experimental details

Crystal data
Chemical formulaC26H23ClFN5O2S2
Mr556.06
Crystal system, space groupMonoclinic, P21/c
Temperature (K)298
a, b, c (Å)9.6931 (5), 24.5636 (12), 11.7095 (6)
β (°) 103.745 (1)
V3)2708.2 (2)
Z4
Radiation typeMo Kα
µ (mm1)0.34
Crystal size (mm)0.20 × 0.10 × 0.06
Data collection
DiffractometerBruker SMART APEX CCD
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2001)
Tmin, Tmax0.936, 0.980
No. of measured, independent and
observed [I > 2σ(I)] reflections
23442, 5326, 3569
Rint0.097
(sin θ/λ)max1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.061, 0.172, 1.00
No. of reflections5326
No. of parameters350
No. of restraints23
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å3)0.50, 0.40

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N3—H3A···S2i0.86 (3)2.65 (3)3.443 (3)153 (3)
C7—H7B···O1ii0.962.513.282 (4)138
Symmetry codes: (i) x1, y, z; (ii) x, y+1, z+2.
 

Acknowledgements

We gratefully acknowledge financial support of this work by the National Natural Science Foundation of China (No. 31000867) and Key Projects in the National Science & Technology Pillar Program (No. 2011BAE06B04).

References

First citationBruker (2000). SMART, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
First citationLiang, Y., Fan, S., Mo, W. Y. & He, H. W. (2007). J. Fluorine Chem. 128, 879–884.  Web of Science CSD CrossRef CAS Google Scholar
First citationSheldrick, G. M. (2001). SADABS. University of Göttingen, Germany.  Google Scholar
First citationSheldrick, G. M. (2008). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

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