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Acta Crystallogr Sect E Struct Rep Online. 2010 August 1; 66(Pt 8): o2137.
Published online 2010 July 31. doi:  10.1107/S1600536810029338
PMCID: PMC3007410

Phosmet: O,O-dimethyl S-phthalimidomethyl phospho­rodithio­ate

Abstract

In the title compound, C11H12NO4PS2, the dihedral angle between the phthalimidyl ring plane and the PS2 plane of the phospho­rodithio­ate group is 60.41 (3)°. In the crystal structure, weak inter­molecular C—H(...)O hydrogen bonds and S(...)S inter­actions [3.3825 (9) Å] contribute to the stabilization of the packing.

Related literature

For information on the toxicity and insecticidal properties of the title compound, see: Song et al. (2009 [triangle]). For related structures, see: Baughman & Allen (1995 [triangle]); Rohrbaugh et al. (1976 [triangle]). For the synthesis, see: Sinderhauf & Schwack (2004 [triangle]).

An external file that holds a picture, illustration, etc.
Object name is e-66-o2137-scheme1.jpg

Experimental

Crystal data

  • C11H12NO4PS2
  • M r = 317.31
  • Triclinic, An external file that holds a picture, illustration, etc.
Object name is e-66-o2137-efi1.jpg
  • a = 8.3428 (18) Å
  • b = 8.6014 (19) Å
  • c = 10.218 (2) Å
  • α = 85.253 (10)°
  • β = 81.478 (10)°
  • γ = 83.961 (9)°
  • V = 719.4 (3) Å3
  • Z = 2
  • Mo Kα radiation
  • μ = 0.49 mm−1
  • T = 173 K
  • 0.29 × 0.25 × 0.15 mm

Data collection

  • Bruker APEXII CCD diffractometer
  • Absorption correction: multi-scan (SADABS; Sheldrick, 1996 [triangle]) T min = 0.871, T max = 0.930
  • 13076 measured reflections
  • 3613 independent reflections
  • 3404 reflections with I > 2σ(I)
  • R int = 0.025

Refinement

  • R[F 2 > 2σ(F 2)] = 0.031
  • wR(F 2) = 0.095
  • S = 1.04
  • 3613 reflections
  • 174 parameters
  • H-atom parameters constrained
  • Δρmax = 0.34 e Å−3
  • Δρmin = −0.44 e Å−3

Data collection: APEX2 (Bruker, 2006 [triangle]); cell refinement: SAINT (Bruker, 2006 [triangle]); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 [triangle]); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL and DIAMOND (Brandenburg, 1998 [triangle]); software used to prepare material for publication: SHELXTL.

Table 1
Hydrogen-bond geometry (Å, °)

Supplementary Material

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536810029338/jh2189sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810029338/jh2189Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

Acknowledgments

This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Education, Science and Technology (No. 2010–0016386).

supplementary crystallographic information

Comment

Phosmet (systematic name: O,O-dimethyl S-phthalimidomethyl phosphorodithioate), is a well known organothiophosphate acaricides and isoindole organothiophosphate insecticides used on plants and animals (Song et al., 2009). However, it's crystal structure has not been reported yet.

In the title compound (Scheme 1, Fig.1), the dihedral angle between the phthalimidyl ring plane and the S1/P1/S2 plane of phosphorodithioate group is 60.41 (3)°. All bond lengths and bond angles of phosphorodithioate group are are comparable to those observed in similar structures (Baughman & Allen, 1995; Rohrbaugh et al., 1976).

In the crystal structure, as shown in Fig. 2, weak C—H···O hydrogen bonds are observed [C2—H2B···O3; H2B···O3 = 2.57 Å; C2—H2B···O3 = 128°; C2···O3 = 3.272 (2) Å; -x + 1, -y + 1, -z and C2—H2C···O4; H2C···O4 = 2.70 Å; C2—H2C···O4 = 130°; C2···O4 = 3.420 (2) Å; -x + 1, -y + 1, -z + 1]. Weak intermolecular S···S interactions with 3.3825 (9) Å also exist. These intermolecular interactions may be contribute to the stabilization of the packing.

Experimental

The title compound was purchased from the Dr. Ehrenstorfer GmbH Company. Slow evaporation of a CH2Cl2 solution gave single crystals suitable for X-ray analysis.

Refinement

All H-atoms were positioned geometrically and refined using a riding model with d(C—H) = 0.95 Å, Uiso = 1.2Ueq(C) for aromatic and 0.98 Å, Uiso = 1.5Ueq(C) for the d(C—H) = 0.98 Å, Uiso = 1.5Ueq(C) for CH3 groups.

Figures

Fig. 1.
The molecular structure of the title compound, showing displacement ellipsoids drawn at the 50% probability level.
Fig. 2.
Crystal packing of the title compound with intermolecular C—H···O and S···S interactions shown as dashed lines. H atoms not involved in intermolecular interactions have been omitted for clarity. ...

Crystal data

C11H12NO4PS2Z = 2
Mr = 317.31F(000) = 328
Triclinic, P1Dx = 1.465 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 8.3428 (18) ÅCell parameters from 9755 reflections
b = 8.6014 (19) Åθ = 2.4–28.5°
c = 10.218 (2) ŵ = 0.49 mm1
α = 85.253 (10)°T = 173 K
β = 81.478 (10)°Block, colourless
γ = 83.961 (9)°0.29 × 0.25 × 0.15 mm
V = 719.4 (3) Å3

Data collection

Bruker APEXII CCD diffractometer3613 independent reflections
Radiation source: fine-focus sealed tube3404 reflections with I > 2σ(I)
graphiteRint = 0.025
[var phi] and ω scansθmax = 28.5°, θmin = 2.0°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)h = −11→11
Tmin = 0.871, Tmax = 0.930k = −11→11
13076 measured reflectionsl = −13→13

Refinement

Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.031Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095H-atom parameters constrained
S = 1.04w = 1/[σ2(Fo2) + (0.0575P)2 + 0.2633P] where P = (Fo2 + 2Fc2)/3
3613 reflections(Δ/σ)max < 0.001
174 parametersΔρmax = 0.34 e Å3
0 restraintsΔρmin = −0.44 e Å3

Special details

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)

xyzUiso*/Ueq
S10.09888 (5)0.15933 (5)0.28102 (5)0.03924 (12)
S20.43827 (4)0.15124 (4)0.39691 (3)0.02668 (10)
P10.32713 (4)0.16877 (4)0.22735 (3)0.02349 (10)
O10.41933 (14)0.04388 (11)0.13285 (10)0.0328 (2)
O20.38169 (14)0.31782 (11)0.13866 (10)0.0306 (2)
O30.75419 (15)0.31462 (15)0.07640 (10)0.0384 (3)
O40.72161 (16)0.33782 (15)0.52567 (10)0.0419 (3)
N10.71376 (14)0.29623 (13)0.30631 (11)0.0258 (2)
C10.4028 (2)−0.12177 (17)0.16526 (19)0.0450 (4)
H1A0.4367−0.15230.25230.067*
H1B0.4716−0.18300.09790.067*
H1C0.2889−0.14180.16740.067*
C20.3344 (2)0.47159 (17)0.18799 (18)0.0412 (4)
H2A0.21540.48900.20490.062*
H2B0.37670.55180.12180.062*
H2C0.37910.47800.27060.062*
C30.65366 (16)0.14476 (16)0.32840 (14)0.0273 (3)
H3A0.71780.07910.39000.033*
H3B0.67040.09420.24320.033*
C40.76056 (16)0.36963 (16)0.18021 (13)0.0271 (3)
C50.82125 (17)0.51897 (16)0.20613 (14)0.0286 (3)
C60.8801 (2)0.63735 (19)0.11828 (17)0.0377 (3)
H60.88150.63510.02530.045*
C70.9376 (2)0.76105 (19)0.1734 (2)0.0453 (4)
H70.97790.84560.11650.054*
C80.9370 (2)0.76272 (19)0.3089 (2)0.0446 (4)
H80.97880.84740.34280.053*
C90.8763 (2)0.64295 (19)0.39698 (17)0.0380 (3)
H90.87580.64420.48990.046*
C100.81732 (17)0.52298 (17)0.34284 (14)0.0290 (3)
C110.74723 (17)0.38001 (17)0.40935 (13)0.0286 (3)

Atomic displacement parameters (Å2)

U11U22U33U12U13U23
S10.02281 (18)0.0388 (2)0.0582 (3)−0.00383 (14)−0.00798 (16)−0.01070 (17)
S20.02212 (17)0.03314 (18)0.02380 (16)−0.00471 (12)−0.00268 (11)0.00543 (12)
P10.02404 (18)0.01980 (16)0.02735 (17)−0.00243 (12)−0.00559 (12)−0.00190 (12)
O10.0399 (6)0.0230 (5)0.0348 (5)−0.0046 (4)0.0011 (4)−0.0068 (4)
O20.0425 (6)0.0219 (4)0.0278 (5)−0.0033 (4)−0.0083 (4)0.0022 (3)
O30.0422 (6)0.0503 (6)0.0252 (5)−0.0161 (5)−0.0042 (4)−0.0026 (4)
O40.0488 (7)0.0529 (7)0.0246 (5)−0.0133 (5)−0.0027 (4)−0.0001 (5)
N10.0242 (5)0.0295 (5)0.0237 (5)−0.0068 (4)−0.0021 (4)0.0008 (4)
C10.0568 (11)0.0217 (6)0.0540 (10)−0.0065 (7)0.0052 (8)−0.0085 (6)
C20.0593 (11)0.0198 (6)0.0460 (9)−0.0006 (6)−0.0155 (7)−0.0001 (6)
C30.0209 (6)0.0269 (6)0.0331 (7)−0.0025 (5)−0.0031 (5)0.0027 (5)
C40.0217 (6)0.0339 (6)0.0255 (6)−0.0062 (5)−0.0031 (5)0.0026 (5)
C50.0233 (6)0.0297 (6)0.0321 (7)−0.0039 (5)−0.0022 (5)0.0014 (5)
C60.0334 (8)0.0370 (7)0.0407 (8)−0.0067 (6)−0.0020 (6)0.0080 (6)
C70.0356 (8)0.0301 (7)0.0672 (11)−0.0081 (6)0.0004 (8)0.0072 (7)
C80.0343 (8)0.0304 (7)0.0693 (12)−0.0063 (6)−0.0008 (7)−0.0130 (7)
C90.0327 (8)0.0365 (7)0.0456 (8)−0.0039 (6)−0.0010 (6)−0.0141 (6)
C100.0236 (6)0.0296 (6)0.0334 (7)−0.0033 (5)−0.0006 (5)−0.0042 (5)
C110.0249 (6)0.0336 (7)0.0270 (6)−0.0039 (5)−0.0016 (5)−0.0023 (5)

Geometric parameters (Å, °)

S1—P11.9103 (6)C2—H2B0.9800
S2—C31.8261 (14)C2—H2C0.9800
S2—P12.0706 (6)C3—H3A0.9900
P1—O11.5671 (10)C3—H3B0.9900
P1—O21.5749 (10)C4—C51.4864 (19)
O1—C11.4520 (18)C5—C61.381 (2)
O2—C21.4494 (17)C5—C101.396 (2)
O3—C41.2070 (18)C6—C71.402 (2)
O4—C111.2081 (18)C6—H60.9500
N1—C111.4003 (18)C7—C81.386 (3)
N1—C41.4069 (17)C7—H70.9500
N1—C31.4335 (17)C8—C91.396 (2)
C1—H1A0.9800C8—H80.9500
C1—H1B0.9800C9—C101.377 (2)
C1—H1C0.9800C9—H90.9500
C2—H2A0.9800C10—C111.4870 (19)
C3—S2—P1102.12 (5)N1—C3—H3B108.9
O1—P1—O296.75 (6)S2—C3—H3B108.9
O1—P1—S1118.01 (5)H3A—C3—H3B107.7
O2—P1—S1117.12 (5)O3—C4—N1124.76 (13)
O1—P1—S2107.80 (5)O3—C4—C5129.98 (13)
O2—P1—S2108.52 (4)N1—C4—C5105.23 (11)
S1—P1—S2107.86 (3)C6—C5—C10121.80 (14)
C1—O1—P1120.26 (10)C6—C5—C4129.95 (14)
C2—O2—P1119.12 (10)C10—C5—C4108.20 (12)
C11—N1—C4112.65 (11)C5—C6—C7116.55 (16)
C11—N1—C3122.77 (11)C5—C6—H6121.7
C4—N1—C3124.30 (12)C7—C6—H6121.7
O1—C1—H1A109.5C8—C7—C6121.44 (15)
O1—C1—H1B109.5C8—C7—H7119.3
H1A—C1—H1B109.5C6—C7—H7119.3
O1—C1—H1C109.5C7—C8—C9121.56 (15)
H1A—C1—H1C109.5C7—C8—H8119.2
H1B—C1—H1C109.5C9—C8—H8119.2
O2—C2—H2A109.5C10—C9—C8116.89 (16)
O2—C2—H2B109.5C10—C9—H9121.6
H2A—C2—H2B109.5C8—C9—H9121.6
O2—C2—H2C109.5C9—C10—C5121.73 (14)
H2A—C2—H2C109.5C9—C10—C11129.60 (14)
H2B—C2—H2C109.5C5—C10—C11108.65 (12)
N1—C3—S2113.49 (9)O4—C11—N1124.50 (14)
N1—C3—H3A108.9O4—C11—C10130.34 (14)
S2—C3—H3A108.9N1—C11—C10105.15 (11)
C3—S2—P1—O146.79 (6)C10—C5—C6—C70.8 (2)
C3—S2—P1—O2−56.96 (6)C4—C5—C6—C7−176.42 (15)
C3—S2—P1—S1175.23 (5)C5—C6—C7—C80.8 (3)
O2—P1—O1—C1−176.64 (13)C6—C7—C8—C9−1.2 (3)
S1—P1—O1—C1−50.98 (14)C7—C8—C9—C100.1 (2)
S2—P1—O1—C171.40 (13)C8—C9—C10—C51.5 (2)
O1—P1—O2—C2−176.16 (12)C8—C9—C10—C11179.35 (15)
S1—P1—O2—C257.54 (12)C6—C5—C10—C9−2.0 (2)
S2—P1—O2—C2−64.80 (12)C4—C5—C10—C9175.78 (14)
C11—N1—C3—S275.68 (15)C6—C5—C10—C11179.78 (13)
C4—N1—C3—S2−110.89 (13)C4—C5—C10—C11−2.49 (16)
P1—S2—C3—N190.77 (10)C4—N1—C11—O4−178.01 (14)
C11—N1—C4—O3174.74 (14)C3—N1—C11—O4−3.9 (2)
C3—N1—C4—O30.7 (2)C4—N1—C11—C101.89 (15)
C11—N1—C4—C5−3.36 (15)C3—N1—C11—C10176.00 (12)
C3—N1—C4—C5−177.37 (12)C9—C10—C11—O42.3 (3)
O3—C4—C5—C63.1 (3)C5—C10—C11—O4−179.63 (16)
N1—C4—C5—C6−178.98 (15)C9—C10—C11—N1−177.61 (15)
O3—C4—C5—C10−174.42 (15)C5—C10—C11—N10.48 (15)
N1—C4—C5—C103.54 (15)

Hydrogen-bond geometry (Å, °)

D—H···AD—HH···AD···AD—H···A
C2—H2B···O3i0.982.573.272 (2)128
C2—H2C···O4ii0.982.703.420 (2)130

Symmetry codes: (i) −x+1, −y+1, −z; (ii) −x+1, −y+1, −z+1.

Footnotes

Supplementary data and figures for this paper are available from the IUCr electronic archives (Reference: JH2189).

References

  • Baughman, R. G. & Allen, J. L. (1995). Acta Cryst. C51, 521–523.
  • Brandenburg, K. (1998). DIAMOND Crystal Impact GbR, Bonn, Germany.
  • Bruker (2006). APEX2 and SAINT Bruker AXS Inc., Madison, Wisconsin, USA.
  • Rohrbaugh, W. J., Meyers, E. K. & Jacobson, R. A. (1976). J. Agric. Food Chem.24, 713–717.
  • Sheldrick, G. M. (1996). SADABS University of Göttingen, Germany.
  • Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. [PubMed]
  • Sinderhauf, K. & Schwack, W. (2004). J. Label Compd. Radiopharm.47, 509–512.
  • Song, Y., Ge, Y., Zhan, Y., Liu, B. & Lu, Y. (2009). Anal. Bioanal. Chem.393, 2001–2008. [PubMed]

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