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

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2403
https://doi.org/10.1107/S1600536810032794

3-Phenyl-2-(pyrrolidin-1-yl)-5,6-di­hydro-8H-thio­pyrano[4′,3′:4,5]thieno[2,3-d]pyrimidin-4(3H)-one

Shuang-Ming Meng,a Hai Xie,a Yue-Qin Fan,a Bu-qin Jinga and Yong Guoa*

aCollege of Chemistry and Chemical Engineering, Shanxi Datong University, Datong, Shanxi 037009, People's Republic of China
*Correspondence e-mail: ybsymsm@126.com

(Received 29 July 2010; accepted 16 August 2010; online 25 August 2010)

In the title compound, C19H19N3OS2, the thio­pyran ring adopts a twist-chair conformation and the pyrimidinone unit is essentially planar, with a mean deviation of 0.0497 Å. The thio­phene ring is essentially planar with a maximum deviation of 0.024 (2) Å, while the pyrrolidine ring exhibits an envelope conformation. The pyrimidinone and thio­phene rings are almost coplanar, forming a dihedral angle of 6.31 (15)°, while the dihedral angle between the mean planes of the phenyl ring and the pyrimidinone ring is 68.13 (10)°. In the crystal structure, adjacent mol­ecules are linked by C—H⋯O hydrogen bonds, forming a two-dimensional network in the ac plane.

Related literature

For the applications of pyrimidine derivatives as pesticides and pharmaceutical agents, see: Condon et al. (1993[Condon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). Brigton Crop Protection Conference on Weeds, pp. 41-46. Alton, Hampshire, England: BCPC Publications.]) and as anti­viral agents, see; Gilchrist (1997[Gilchrist, T. L. (1997). Heterocyclic Chemistry, 3rd ed., pp. 261-276. Singapore: Addison Wesley Longman.]). For a related structure, see: Xie et al. (2008[Xie, H., Meng, S.-M., Fan, Y.-Q. & Guo, Y. (2008). Acta Cryst. E64, o2434.]).

[Scheme 1]

Experimental

Crystal data

  • C19H19N3OS2

  • Mr = 369.49

  • Triclinic, [P \overline 1]

  • a = 8.1484 (8) Å

  • b = 9.3455 (9) Å

  • c = 12.1834 (12) Å

  • α = 73.668 (1)°

  • β = 88.629 (1)°

  • γ = 79.568 (1)°

  • V = 875.26 (15) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.32 mm−1

  • T = 298 K

  • 0.30 × 0.23 × 0.18 mm
Data collection

  • Bruker SMART CCD area-detector diffractometer

  • Absorption correction: multi-scan (SADABS; Sheldrick, 2000[Sheldrick, G. M. (2000). SADABS. University of Göttingen, Germany.]) Tmin = 0.911, Tmax = 0.945

  • 4828 measured reflections

  • 3349 independent reflections

  • 2709 reflections with I > 2σ(I)

  • Rint = 0.016
Refinement

  • R[F2 > 2σ(F2)] = 0.043

  • wR(F2) = 0.119

  • S = 1.06

  • 3349 reflections

  • 226 parameters

  • H-atom parameters constrained

  • Δρmax = 0.50 e Å−3

  • Δρmin = −0.44 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
C11—H11B⋯O1i 0.97 2.58 3.434 (3) 148
C1—H1A⋯O1ii 0.97 2.48 3.287 (3) 140
Symmetry codes: (i) x+1, y, z; (ii) -x, -y, -z+1.

Data collection: SMART (Bruker, 2000[Bruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2000[Bruker (2000). SMART and SAINT. 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/PC (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); software used to prepare material for publication: publCIF (Westrip, 2010[Westrip, S. P. (2010). J. Appl. Cryst. 43, 920-925.]).

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810032794/pv2315sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810032794/pv2315Isup2.hkl

checkCIF report


Comment top

Pyrimidine derivatives are very important molecules in biology and have many application in the areas of pesticide and pharmaceutical agents (Condon et al., 1993). Pyrimidine derivatives have also been developed as antiviral agents, such as AZT (azidothymidine), which is the most widely used anti-AIDS drug (Gilchrist, 1997). In order to discover further biologically active pyrimidine compounds, the title compound was synthesized, and its crystal structure was determined which is presented in this paper.

In the title compound (Fig. 1) the tetrahydropyran ring adopts a twist chair conformation with S2 and C1 lying 0.451 (5) and 0.474 (5) Å, respectively, on the opposite sides of the plane formed by the rest of the ring atoms. The pyridinone unit is essentially planar with a mean deviation of 0.0497 Å; the maximum deviation of any atom from the plane is 0.0432 (14) Å for N3. The pyrimidone and the thiophene rings are almost coplanar with the dihedral angle 6.31 (15)° and the dihedral angle between the mean-planes of the phenyl ring and the pyridinone ring is 68.13 (10)°. The thiophene ring is essentially planar (max. dev. 0.024 (2) Å for C4) while the tetrahydropyrrole exhibits a C12-envelop conformation with C12 lying 0.568 (4) Å out of the plane formed by the rest of the atoms in the ring.

The bond distances and bond angles in the title compound are comparable to the corresponding distances and angles reported for a closely related compound (Xie et al., 2008). In the crystal structure, adjacent molecules are linked by C–H···O hydrogen bonding interactions (Tab. 1), and form a two-dimensional network (Fig. 2).

Related literature top

For the applications of pyrimidine derivatives as pesticides and pharmaceutical agents, see: Condon et al. (1993) and as antiviral agents, see; Gilchrist (1997). For a related structure, see: Xie et al. (2008).

Experimental top

To a solution of iminophosphorane (2.0 mmol) in absolute anhydrous dichloromethane (10.0 ml), isocyanatobenzene (2.0 mmol) was added under nitrogen atmosphere at room temperature. After the reaction mixture was stirred for 3.0 h at room temperature, the iminophosphorane had disappeared (TLC monitored). The solvent was removed under reduced pressure and EtOH/petroleum ether (1:3, 15.0 ml) was added to precipitate triphenylphosphine oxide. Removal of the solvent gave carbodiimides, which were used directly without further purification. To a solution of carbodiimides in dichloromethane (10.0 ml) was added pyrrolidine (2.0 mmol). The reaction mixture was left unstirred for 6 h. The solvent was removed and anhydrous EtOH (10.0 ml) with several drops of EtONa was added. The mixture was stirred for 6–12 h at room temperature. The solution was condensed, workup and chromatography (hexane/AcOEt) gave the expected cyclic compounds in good yield. The crystals of the title compound were grown mother liquor by slowly evaporation from at room.

Refinement top

The hydrogen atoms were placed in geometrically idealized positions with Csp2—H = 0.93Å and Csp3—H = 0.97 Å, and constrained to ride on their parent atoms with Uiso(H) set to 1.2 × Ueq(C).

Structure description top

Pyrimidine derivatives are very important molecules in biology and have many application in the areas of pesticide and pharmaceutical agents (Condon et al., 1993). Pyrimidine derivatives have also been developed as antiviral agents, such as AZT (azidothymidine), which is the most widely used anti-AIDS drug (Gilchrist, 1997). In order to discover further biologically active pyrimidine compounds, the title compound was synthesized, and its crystal structure was determined which is presented in this paper.

In the title compound (Fig. 1) the tetrahydropyran ring adopts a twist chair conformation with S2 and C1 lying 0.451 (5) and 0.474 (5) Å, respectively, on the opposite sides of the plane formed by the rest of the ring atoms. The pyridinone unit is essentially planar with a mean deviation of 0.0497 Å; the maximum deviation of any atom from the plane is 0.0432 (14) Å for N3. The pyrimidone and the thiophene rings are almost coplanar with the dihedral angle 6.31 (15)° and the dihedral angle between the mean-planes of the phenyl ring and the pyridinone ring is 68.13 (10)°. The thiophene ring is essentially planar (max. dev. 0.024 (2) Å for C4) while the tetrahydropyrrole exhibits a C12-envelop conformation with C12 lying 0.568 (4) Å out of the plane formed by the rest of the atoms in the ring.

The bond distances and bond angles in the title compound are comparable to the corresponding distances and angles reported for a closely related compound (Xie et al., 2008). In the crystal structure, adjacent molecules are linked by C–H···O hydrogen bonding interactions (Tab. 1), and form a two-dimensional network (Fig. 2).

For the applications of pyrimidine derivatives as pesticides and pharmaceutical agents, see: Condon et al. (1993) and as antiviral agents, see; Gilchrist (1997). For a related structure, see: Xie et al. (2008).

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/PC (Sheldrick, 2008); software used to prepare material for publication: publCIF (Westrip, 2010).

Figures top
[Figure 1] Fig. 1. The structure of (I), with displacement ellipsoids drawn at the 30% probability level for the non-H atoms.
[Figure 2] Fig. 2. The H-bonds network of the title compound(I), dotted lines show C—H···O bonds.
3-Phenyl-2-(pyrrolidin-1-yl)-5,6-dihydro-8H- thiopyrano[4',3':4,5]thieno[2,3-d]pyrimidin-4(3H)-one top
Crystal data top
C19H19N3OS2Z = 2
Mr = 369.49F(000) = 388
Triclinic, P1Dx = 1.402 Mg m−3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.1484 (8) ÅCell parameters from 2113 reflections
b = 9.3455 (9) Åθ = 0.9–0.8°
c = 12.1834 (12) ŵ = 0.32 mm−1
α = 73.668 (1)°T = 298 K
β = 88.629 (1)°Block, yellow
γ = 79.568 (1)°0.30 × 0.23 × 0.18 mm
V = 875.26 (15) Å3
Data collection top
Bruker SMART CCD area-detector
diffractometer		3349 independent reflections
Radiation source: fine-focus sealed tube2709 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.016
ω scansθmax = 26.0°, θmin = 1.7°
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		h = −10→7
Tmin = 0.911, Tmax = 0.945k = −11→11
4828 measured reflectionsl = −15→14
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)] = 0.043Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.119H-atom parameters constrained
S = 1.06 w = 1/[σ2(Fo2) + (0.0534P)2 + 0.3774P]
where P = (Fo2 + 2Fc2)/3
3349 reflections(Δ/σ)max < 0.001
226 parametersΔρmax = 0.50 e Å−3
0 restraintsΔρmin = −0.44 e Å−3
Crystal data top
C19H19N3OS2γ = 79.568 (1)°
Mr = 369.49V = 875.26 (15) Å3
Triclinic, P1Z = 2
a = 8.1484 (8) ÅMo Kα radiation
b = 9.3455 (9) ŵ = 0.32 mm−1
c = 12.1834 (12) ÅT = 298 K
α = 73.668 (1)°0.30 × 0.23 × 0.18 mm
β = 88.629 (1)°
Data collection top
Bruker SMART CCD area-detector
diffractometer		3349 independent reflections
Absorption correction: multi-scan
(SADABS; Sheldrick, 2000)		2709 reflections with I > 2σ(I)
Tmin = 0.911, Tmax = 0.945Rint = 0.016
4828 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0430 restraints
wR(F2) = 0.119H-atom parameters constrained
S = 1.06Δρmax = 0.50 e Å−3
3349 reflectionsΔρmin = −0.44 e Å−3
226 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*/Ueq
S10.47598 (8)0.15501 (7)0.76959 (5)0.04843 (19)
S20.06845 (11)−0.09908 (9)0.87874 (6)0.0725 (3)
N10.5900 (2)0.2755 (2)0.55975 (14)0.0395 (4)
N30.4362 (2)0.27799 (19)0.39525 (13)0.0364 (4)
N20.6791 (2)0.3883 (2)0.38313 (14)0.0370 (4)
O10.2152 (2)0.1535 (2)0.40870 (14)0.0604 (5)
C70.3484 (3)0.1486 (2)0.58029 (17)0.0374 (5)
C50.4765 (3)0.1994 (2)0.62133 (17)0.0383 (5)
C130.8080 (3)0.4343 (3)0.44164 (18)0.0409 (5)
H13A0.87670.34690.49350.049*
H13B0.75790.50360.48440.049*
C90.5685 (3)0.3119 (2)0.44757 (16)0.0346 (4)
C100.7206 (3)0.4014 (3)0.26241 (17)0.0419 (5)
H10A0.64740.48610.21120.050*
H10B0.71220.30920.24290.050*
C140.3260 (3)0.5119 (2)0.24945 (17)0.0400 (5)
H140.32660.56420.30410.048*
C150.3794 (3)0.2783 (3)0.1980 (2)0.0505 (6)
H150.41690.17400.21780.061*
C60.2442 (3)0.0770 (2)0.66839 (18)0.0407 (5)
C80.3242 (3)0.1861 (2)0.45921 (18)0.0404 (5)
C30.0878 (3)0.0243 (3)0.6458 (2)0.0483 (6)
H3A0.1178−0.07470.63260.058*
H3B0.03160.09400.57690.058*
C40.2990 (3)0.0722 (3)0.77344 (19)0.0460 (5)
C110.8993 (3)0.4273 (3)0.25634 (19)0.0491 (6)
H11A0.92230.48780.18070.059*
H11B0.97750.33180.27520.059*
C120.9097 (3)0.5119 (3)0.34500 (19)0.0479 (6)
H12A1.02440.50190.37000.057*
H12B0.86200.61860.31500.057*
C180.2692 (3)0.5888 (3)0.13848 (19)0.0523 (6)
H180.23260.69330.11830.063*
C1−0.0312 (3)0.0142 (3)0.7442 (2)0.0656 (7)
H1A−0.1244−0.02940.72870.079*
H1B−0.07500.11560.74960.079*
C170.2670 (4)0.5117 (4)0.0587 (2)0.0652 (8)
H170.22890.5640−0.01570.078*
C20.2226 (4)0.0138 (3)0.8875 (2)0.0639 (7)
H2A0.17070.09900.91460.077*
H2B0.3099−0.04700.94250.077*
C160.3206 (4)0.3571 (4)0.0874 (2)0.0660 (8)
H160.31740.30530.03280.079*
C190.3813 (2)0.3578 (2)0.27804 (16)0.0362 (5)
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
S10.0565 (4)0.0596 (4)0.0322 (3)−0.0235 (3)0.0016 (2)−0.0098 (2)
S20.0983 (6)0.0831 (5)0.0519 (4)−0.0533 (5)0.0301 (4)−0.0233 (4)
N10.0401 (10)0.0474 (10)0.0320 (9)−0.0142 (8)−0.0005 (7)−0.0089 (8)
N30.0368 (9)0.0427 (9)0.0302 (8)−0.0127 (8)−0.0029 (7)−0.0073 (7)
N20.0354 (9)0.0487 (10)0.0308 (8)−0.0153 (8)0.0017 (7)−0.0128 (7)
O10.0633 (11)0.0780 (12)0.0444 (9)−0.0425 (10)−0.0097 (8)−0.0050 (8)
C70.0400 (11)0.0339 (10)0.0361 (11)−0.0085 (9)−0.0015 (9)−0.0053 (8)
C50.0420 (11)0.0402 (11)0.0322 (10)−0.0102 (9)0.0008 (9)−0.0078 (9)
C130.0378 (11)0.0512 (13)0.0377 (11)−0.0149 (10)−0.0038 (9)−0.0143 (10)
C90.0350 (10)0.0375 (10)0.0321 (10)−0.0082 (9)−0.0006 (8)−0.0102 (8)
C100.0371 (11)0.0597 (14)0.0324 (11)−0.0131 (10)0.0027 (9)−0.0158 (10)
C140.0365 (11)0.0520 (13)0.0324 (10)−0.0137 (10)0.0018 (8)−0.0100 (9)
C150.0524 (14)0.0603 (15)0.0471 (13)−0.0160 (12)0.0031 (11)−0.0249 (11)
C60.0433 (12)0.0350 (11)0.0416 (12)−0.0100 (9)0.0012 (9)−0.0055 (9)
C80.0412 (12)0.0398 (11)0.0405 (11)−0.0130 (10)−0.0034 (9)−0.0080 (9)
C30.0481 (13)0.0464 (13)0.0484 (13)−0.0182 (11)0.0020 (10)−0.0042 (10)
C40.0514 (13)0.0464 (12)0.0414 (12)−0.0172 (11)0.0070 (10)−0.0097 (10)
C110.0388 (12)0.0715 (16)0.0441 (12)−0.0180 (11)0.0081 (10)−0.0235 (12)
C120.0403 (12)0.0599 (14)0.0498 (13)−0.0198 (11)0.0049 (10)−0.0189 (11)
C180.0510 (14)0.0613 (15)0.0376 (12)−0.0139 (12)−0.0022 (10)−0.0002 (11)
C10.0525 (15)0.0728 (18)0.083 (2)−0.0252 (14)0.0168 (14)−0.0334 (16)
C170.0686 (18)0.095 (2)0.0297 (12)−0.0255 (16)−0.0049 (11)−0.0070 (13)
C20.0761 (19)0.0790 (18)0.0458 (14)−0.0381 (16)0.0188 (13)−0.0187 (13)
C160.0736 (19)0.099 (2)0.0394 (13)−0.0287 (17)0.0014 (12)−0.0347 (14)
C190.0317 (10)0.0490 (12)0.0298 (10)−0.0128 (9)−0.0002 (8)−0.0107 (9)
Geometric parameters (Å, º) top
S1—C51.736 (2)C14—H140.9300
S1—C41.750 (2)C15—C191.385 (3)
S2—C11.801 (3)C15—C161.390 (4)
S2—C21.803 (3)C15—H150.9300
N1—C91.320 (3)C6—C41.352 (3)
N1—C51.352 (3)C6—C31.504 (3)
N3—C91.392 (3)C3—C11.517 (3)
N3—C81.432 (3)C3—H3A0.9700
N3—C191.451 (2)C3—H3B0.9700
N2—C91.350 (3)C4—C21.507 (3)
N2—C131.473 (2)C11—C121.519 (3)
N2—C101.477 (2)C11—H11A0.9700
O1—C81.220 (3)C11—H11B0.9700
C7—C51.379 (3)C12—H12A0.9700
C7—C81.427 (3)C12—H12B0.9700
C7—C61.442 (3)C18—C171.366 (4)
C13—C121.513 (3)C18—H180.9300
C13—H13A0.9700C1—H1A0.9700
C13—H13B0.9700C1—H1B0.9700
C10—C111.516 (3)C17—C161.377 (4)
C10—H10A0.9700C17—H170.9300
C10—H10B0.9700C2—H2A0.9700
C14—C191.375 (3)C2—H2B0.9700
C14—C181.386 (3)C16—H160.9300
C5—S1—C491.1 (1)C1—C3—H3A109.1
C1—S2—C298.8 (1)C6—C3—H3B109.1
C9—N1—C5115.5 (2)C1—C3—H3B109.1
C9—N3—C8122.0 (2)H3A—C3—H3B107.9
C9—N3—C19122.1 (2)C6—C4—C2128.5 (2)
C8—N3—C19114.7 (2)C6—C4—S1113.0 (2)
C9—N2—C13118.4 (2)C2—C4—S1118.5 (2)
C9—N2—C10128.8 (2)C10—C11—C12103.6 (2)
C13—N2—C10110.9 (2)C10—C11—H11A111.0
C5—C7—C8117.7 (2)C12—C11—H11A111.0
C5—C7—C6113.8 (2)C10—C11—H11B111.0
C8—C7—C6128.2 (2)C12—C11—H11B111.0
N1—C5—C7127.4 (2)H11A—C11—H11B109.0
N1—C5—S1121.8 (2)C13—C12—C11103.2 (2)
C7—C5—S1110.8 (2)C13—C12—H12A111.1
N2—C13—C12103.8 (2)C11—C12—H12A111.1
N2—C13—H13A111.0C13—C12—H12B111.1
C12—C13—H13A111.0C11—C12—H12B111.1
N2—C13—H13B111.0H12A—C12—H12B109.1
C12—C13—H13B111.0C17—C18—C14120.2 (2)
H13A—C13—H13B109.0C17—C18—H18119.9
N1—C9—N2117.2 (2)C14—C18—H18119.9
N1—C9—N3122.8 (2)C3—C1—S2112.3 (2)
N2—C9—N3120.0 (2)C3—C1—H1A109.2
N2—C10—C11103.5 (2)S2—C1—H1A109.2
N2—C10—H10A111.1C3—C1—H1B109.2
C11—C10—H10A111.1S2—C1—H1B109.2
N2—C10—H10B111.1H1A—C1—H1B107.9
C11—C10—H10B111.1C18—C17—C16120.5 (2)
H10A—C10—H10B109.0C18—C17—H17119.7
C19—C14—C18119.4 (2)C16—C17—H17119.7
C19—C14—H14120.3C4—C2—S2111.9 (2)
C18—C14—H14120.3C4—C2—H2A109.2
C19—C15—C16118.8 (2)S2—C2—H2A109.2
C19—C15—H15120.6C4—C2—H2B109.2
C16—C15—H15120.6S2—C2—H2B109.2
C4—C6—C7111.3 (2)H2A—C2—H2B107.9
C4—C6—C3124.3 (2)C17—C16—C15120.1 (2)
C7—C6—C3124.3 (2)C17—C16—H16119.9
O1—C8—C7126.3 (2)C15—C16—H16119.9
O1—C8—N3119.5 (2)C14—C19—C15121.0 (2)
C7—C8—N3114.1 (2)C14—C19—N3118.9 (2)
C6—C3—C1112.4 (2)C15—C19—N3120.1 (2)
C6—C3—H3A109.1
C9—N1—C5—C74.1 (3)C19—N3—C8—O116.0 (3)
C9—N1—C5—S1−175.1 (2)C9—N3—C8—C77.0 (3)
C8—C7—C5—N1−3.7 (3)C19—N3—C8—C7−160.6 (2)
C6—C7—C5—N1−177.4 (2)C4—C6—C3—C119.0 (3)
C8—C7—C5—S1175.5 (2)C7—C6—C3—C1−156.5 (2)
C6—C7—C5—S11.9 (2)C7—C6—C4—C2177.0 (2)
C4—S1—C5—N1178.0 (2)C3—C6—C4—C21.0 (4)
C4—S1—C5—C7−1.3 (2)C7—C6—C4—S10.6 (3)
C9—N2—C13—C12178.6 (2)C3—C6—C4—S1−175.5 (2)
C10—N2—C13—C1213.1 (2)C5—S1—C4—C60.4 (2)
C5—N1—C9—N2179.8 (2)C5—S1—C4—C2−176.4 (2)
C5—N1—C9—N31.5 (3)N2—C10—C11—C12−30.9 (2)
C13—N2—C9—N1−4.0 (3)N2—C13—C12—C11−31.9 (2)
C10—N2—C9—N1158.6 (2)C10—C11—C12—C1339.2 (2)
C13—N2—C9—N3174.4 (2)C19—C14—C18—C170.6 (3)
C10—N2—C9—N3−23.0 (3)C6—C3—C1—S2−53.3 (3)
C8—N3—C9—N1−7.1 (3)C2—S2—C1—C362.2 (2)
C19—N3—C9—N1159.5 (2)C14—C18—C17—C160.1 (4)
C8—N3—C9—N2174.5 (2)C6—C4—C2—S214.9 (4)
C19—N3—C9—N2−18.8 (3)S1—C4—C2—S2−168.8 (2)
C9—N2—C10—C11−152.5 (2)C1—S2—C2—C4−40.8 (2)
C13—N2—C10—C1111.2 (2)C18—C17—C16—C15−0.7 (4)
C5—C7—C6—C4−1.6 (3)C19—C15—C16—C170.7 (4)
C8—C7—C6—C4−174.4 (2)C18—C14—C19—C15−0.7 (3)
C5—C7—C6—C3174.4 (2)C18—C14—C19—N3−178.4 (2)
C8—C7—C6—C31.6 (4)C16—C15—C19—C140.1 (3)
C5—C7—C8—O1−178.3 (2)C16—C15—C19—N3177.7 (2)
C6—C7—C8—O1−5.7 (4)C9—N3—C19—C14−60.2 (3)
C5—C7—C8—N3−1.9 (3)C8—N3—C19—C14107.4 (2)
C6—C7—C8—N3170.6 (2)C9—N3—C19—C15122.1 (2)
C9—N3—C8—O1−176.4 (2)C8—N3—C19—C15−70.3 (2)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11B···O1i0.972.583.434 (3)148
C1—H1A···O1ii0.972.483.287 (3)140
C3—H3B···O10.972.503.038 (3)115
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1.

Experimental details

Crystal data
Chemical formulaC19H19N3OS2
Mr369.49
Crystal system, space groupTriclinic, P1
Temperature (K)298
a, b, c (Å)8.1484 (8), 9.3455 (9), 12.1834 (12)
α, β, γ (°)73.668 (1), 88.629 (1), 79.568 (1)
V (Å3)875.26 (15)
Z2
Radiation typeMo Kα
µ (mm−1)0.32
Crystal size (mm)0.30 × 0.23 × 0.18
Data collection
DiffractometerBruker SMART CCD area-detector
Absorption correctionMulti-scan
(SADABS; Sheldrick, 2000)
Tmin, Tmax0.911, 0.945
No. of measured, independent and
observed [I > 2σ(I)] reflections		4828, 3349, 2709
Rint0.016
(sin θ/λ)max (Å−1)0.617
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.043, 0.119, 1.06
No. of reflections3349
No. of parameters226
H-atom treatmentH-atom parameters constrained
Δρmax, Δρmin (e Å−3)0.50, −0.44

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL/PC (Sheldrick, 2008), publCIF (Westrip, 2010).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
C11—H11B···O1i0.972.583.434 (3)147.6
C1—H1A···O1ii0.972.483.287 (3)140.3
Symmetry codes: (i) x+1, y, z; (ii) −x, −y, −z+1.
 

Acknowledgements

The authors acknowledge financial support from the Provincial Natural Science Foundation of Shanxi Province of China (grant No. 2010011018)

References

First citationBruker (2000). SMART and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationCondon, M. E., Brady, T. E., Feist, D., Malefyt, T., Marc, P., Quakenbush, L. S., Rodaway, S. J., Shaner, D. L. & Tecle, B. (1993). Brigton Crop Protection Conference on Weeds, pp. 41–46. Alton, Hampshire, England: BCPC Publications.  Google Scholar
 First citationGilchrist, T. L. (1997). Heterocyclic Chemistry, 3rd ed., pp. 261–276. Singapore: Addison Wesley Longman.  Google Scholar
 First citationSheldrick, G. M. (2000). 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
 First citationWestrip, S. P. (2010). J. Appl. Cryst. 43, 920–925.  Web of Science CrossRef CAS IUCr Journals Google Scholar
 First citationXie, H., Meng, S.-M., Fan, Y.-Q. & Guo, Y. (2008). Acta Cryst. E64, o2434.  Web of Science CSD CrossRef 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.

Journal logoCRYSTALLOGRAPHIC
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ISSN: 2056-9890
Volume 66| Part 9| September 2010| Page o2403
https://doi.org/10.1107/S1600536810032794
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