O,O′-Diethyl {(Z)-[(2-chloro­phen­yl)(cyano)methyl­ene]amino­oxy}thio­phospho­nate

Gao, Q.; Zhao, Q.; Wang, P.

doi:10.1107/S160053680900693X

organic compounds

CRYSTALLOGRAPHIC
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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o673

doi:10.1107/S160053680900693X

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O,O′-Diethyl {(Z)-[(2-chlorophenyl)(cyano)methylene]aminooxy}thiophosphonate

Qiong Gao,^a Qing-xia Zhao ^a and Pu-hai Wang ^b ^*

^aCollege of Life Science and Pharmaceutical Engineering, Nanjing University of Technology, No. 5 Xinmofan Road, Nanjing 210009, People's Republic of China, and ^bDepartment of Medicinal Chemistry, Jiangsu Provincial Institute of Materia Medica, Nanjing University of Technology, No. 26 Majia Street, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: wangpuhai@hotmail.com

(Received 29 December 2008; accepted 25 February 2009; online 6 March 2009)

The title molecule, C₁₂H₁₄ClN₂O₃PS, has a cis configuration with respect to the C=N bond. Intermolecular C—H⋯O interactions interconnect the molecules into chains along the c axis. The chains are further connected into a two-dimensional network parallel to the bc plane by weak π–π interactions between adjacent aromatic rings (centroid–centroid distance = 3.772Å).

Related literature

For the insectidal activity of the title compound, see: Hudson & Obudho (1972 ); Le Berre et al. (1972 ). For its preparation and reactivity, see: Walter & Clifton (1973 ); Wang et al. (1996 ).

Experimental

Crystal data

C₁₂H₁₄ClN₂O₃PS
M_r = 332.73
Monoclinic, P 2₁ /c
a = 10.518 (2) Å
b = 20.215 (4) Å
c = 7.9650 (16) Å
β = 110.11 (3)°
V = 1590.3 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.48 mm⁻¹
T = 293 K
0.30 × 0.20 × 0.10 mm

Data collection

Enraf–Nonius CAD-4 diffractometer
Absorption correction: ψ scan (North et al., 1968 ) T_min = 0.870, T_max = 0.954
2889 measured reflections
2889 independent reflections
1981 reflections with I > 2σ(I)
3 standard reflections frequency: 120 min intensity decay: 1.0%

Refinement

R[F² > 2σ(F²)] = 0.061
wR(F²) = 0.192
S = 1.09
2889 reflections
183 parameters
H-atom parameters constrained
Δρ_max = 0.31 e Å⁻³
Δρ_min = −0.39 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C2—H2A⋯O1ⁱ	0.97	2.58	3.396 (6)	142
Symmetry code: (i) $[x, -y+{\script{1\over 2}}, z+{\script{1\over 2}}]$ .

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994 ); cell refinement: CAD-4 EXPRESS; data reduction: XCAD4 (Harms & Wocadlo, 1995 ); 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: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S160053680900693X/fb2135sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S160053680900693X/fb2135Isup2.hkl

checkCIF report

Comment top

O,O-diethyl-O-(2-chlorophenylglyoxylonitrile oximino)thiophosphate (Chlorphoxim) was shown to be efficient against adult mosquitoes as well as agricultural insects (Hudson et al., 1972). It was also successfully tested against the larvae of the blackfly (Simulium damnosum), the insect vector of human onchocerciasis in West Africa (Le Berre et al., 1972). The title substance combined with niclosamide exhibited significant molluscicidal synergism against snails (Oncomelania hupensis) (Wang et al., 1996). The synthesis of the title compound has been described by Walter et al. (1973). As a part of our own studies in this area, we report here its crystal structure.

The title molecule shows a cis configuration (Fig. 1) on the C═N bond. The molecules are linked into chains along the axis c via weak intermolecular C—H···O interactions (Fig. 2, Tab. 1). The chains are further connected into a two-dimensional network via weak π-π electron interactions between the adjacent phenyl rings: The centroid-centroid distance is 3.772 Å.

Related literature top

For the insectidal activity of the title compound, see: Hudson & Obudho (1972); Le Berre et al. (1972). For its preparation and reactivity, see: Walter & Clifton (1973); Wang et al. (1996).

Experimental top

Sodium, 2.30 g (0.1 mol), reacted with 50 ml of absolute ethanol in order to get sodium ethoxide solution. 15.20 g (0.1 mol) of 2-chlorophenylacetonitrile, was added dropwise to the cooled sodium ethoxide (about 278 K) and then 10.30 g (0.1 mol) of butyl nitrite was added dropwise. The mixture was stirred at room temperature for 1 h under reduced pressure until the volume was reduced to 30 ml. Then 50 ml of ethyl ether was added, and the precipitated solid was filtered off and washed with ethyl ether to afford sodium 2-chlorophenylglyoxylonitrile oxime (11.3 g, 56%). Diethyl phosphorochloridothionate, 5.70 g (0.03 mol), was added dropwise to 6.00 g (0.03 mol) of sodium 2-chlorophenylglyoxylonitrile oxime, which was suspended in 20 ml of dry acetone. The mixture was stirred for 1 h. Thin layered chromatography using petroleum ether and ethyl acetate as expanding solvent indicated just one point. The mixture was then concentrated under reduced pressure and 50 ml of water was added to the residue. The precipitated solid that had appeared was filtered off, washed thoroughly with absolute ethanol, dried and recrystallized from petroleum ether to afford the title compound (8.9 g, yield 89%) as a white crystalline solid. The title crystals suitable for X-ray diffraction were obtained by slow evaporation of the acetone solution. The average size of the block-like crystals is 0.2 × 0.2 × 0.2 mm.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1994); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1994); data reduction: XCAD4 (Harms & Wocadlo, 1995); 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: SHELXS97 (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title molecule with the atom-numbering scheme. The displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of the title structure. The dashed lines represent weak C—H···O interactions.

O,O'-Diethyl {(Z)-[(2-chlorophenyl)(cyano)methylene]aminooxy}thiophosphonate top

Crystal data top

C₁₂H₁₄ClN₂O₃PS	F(000) = 688
M_r = 332.73	D_x = 1.390 Mg m⁻³
Monoclinic, P2₁/c	Melting point: 341.5 K
Hall symbol: -P 2ybc	Mo Kα radiation, λ = 0.71073 Å
a = 10.518 (2) Å	Cell parameters from 25 reflections
b = 20.215 (4) Å	θ = 9.0–13.0°
c = 7.9650 (16) Å	µ = 0.48 mm⁻¹
β = 110.11 (3)°	T = 293 K
V = 1590.3 (6) Å³	Block, colourless
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	1981 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.000
Graphite monochromator	θ_max = 25.3°, θ_min = 2.0°
ω/2θ scans	h = −12→11
Absorption correction: ψ scan (North et al., 1968)	k = 0→24
T_min = 0.870, T_max = 0.954	l = 0→9
2889 measured reflections	3 standard reflections every 120 min
2889 independent reflections	intensity decay: 1.0%

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)] = 0.061	Hydrogen site location: difference Fourier map
wR(F²) = 0.192	H-atom parameters constrained
S = 1.09	w = 1/[σ²(F_o²) + (0.0957P)² + 1.1623P] where P = (F_o² + 2F_c²)/3
2889 reflections	(Δ/σ)_max < 0.001
183 parameters	Δρ_max = 0.31 e Å⁻³
0 restraints	Δρ_min = −0.39 e Å⁻³

Crystal data top

C₁₂H₁₄ClN₂O₃PS	V = 1590.3 (6) Å³
M_r = 332.73	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 10.518 (2) Å	µ = 0.48 mm⁻¹
b = 20.215 (4) Å	T = 293 K
c = 7.9650 (16) Å	0.30 × 0.20 × 0.10 mm
β = 110.11 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	1981 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.000
T_min = 0.870, T_max = 0.954	3 standard reflections every 120 min
2889 measured reflections	intensity decay: 1.0%
2889 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.192	H-atom parameters constrained
S = 1.09	Δρ_max = 0.31 e Å⁻³
2889 reflections	Δρ_min = −0.39 e Å⁻³
183 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
Cl	0.9833 (2)	0.10567 (10)	1.4318 (2)	0.1103 (7)
S	0.44401 (12)	0.05415 (6)	0.77933 (17)	0.0620 (4)
P	0.49482 (11)	0.14026 (6)	0.73194 (14)	0.0468 (3)
O1	0.3963 (3)	0.19852 (15)	0.7185 (4)	0.0562 (8)
O2	0.5248 (4)	0.15378 (16)	0.5556 (4)	0.0687 (9)
O3	0.6273 (3)	0.16956 (14)	0.8892 (4)	0.0518 (7)
N1	0.7388 (3)	0.12634 (16)	0.9243 (4)	0.0477 (8)
N2	0.8474 (5)	0.2615 (3)	1.2012 (8)	0.0939 (16)
C1	0.2127 (6)	0.2550 (3)	0.7678 (8)	0.0898 (18)
H1B	0.1664	0.2624	0.8511	0.135*
H1C	0.1501	0.2376	0.6583	0.135*
H1D	0.2493	0.2960	0.7441	0.135*
C2	0.3231 (5)	0.2074 (3)	0.8440 (7)	0.0690 (13)
H2A	0.3843	0.2236	0.9575	0.083*
H2B	0.2864	0.1653	0.8645	0.083*
C3	0.5814 (7)	0.1315 (3)	0.2996 (7)	0.0884 (18)
H3A	0.6215	0.0996	0.2437	0.133*
H3B	0.6290	0.1727	0.3118	0.133*
H3C	0.4881	0.1379	0.2273	0.133*
C4	0.5897 (7)	0.1079 (3)	0.4736 (8)	0.0847 (17)
H4A	0.5460	0.0650	0.4623	0.102*
H4B	0.6839	0.1027	0.5482	0.102*
C5	0.8423 (4)	0.2119 (2)	1.1322 (6)	0.0599 (12)
C6	0.8431 (4)	0.14942 (19)	1.0451 (5)	0.0436 (9)
C7	0.9702 (4)	0.1113 (2)	1.0871 (6)	0.0475 (9)
C8	1.0192 (5)	0.0965 (2)	0.9514 (7)	0.0590 (11)
H8A	0.9715	0.1105	0.8356	0.071*
C9	1.1372 (5)	0.0612 (3)	0.9845 (9)	0.0759 (15)
H9A	1.1686	0.0512	0.8917	0.091*
C10	1.2084 (5)	0.0411 (3)	1.1563 (10)	0.0865 (19)
H10A	1.2885	0.0174	1.1797	0.104*
C11	1.1627 (6)	0.0554 (3)	1.2906 (9)	0.0836 (17)
H11A	1.2118	0.0420	1.4065	0.100*
C12	1.0435 (5)	0.0899 (2)	1.2575 (6)	0.0642 (12)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl	0.1224 (14)	0.1444 (17)	0.0590 (8)	0.0170 (12)	0.0247 (9)	0.0086 (9)
S	0.0607 (7)	0.0481 (6)	0.0785 (8)	−0.0014 (5)	0.0256 (6)	−0.0008 (6)
P	0.0463 (6)	0.0495 (6)	0.0467 (6)	0.0072 (5)	0.0187 (5)	0.0010 (5)
O1	0.0543 (16)	0.0572 (18)	0.0650 (18)	0.0168 (14)	0.0309 (14)	0.0129 (14)
O2	0.084 (2)	0.070 (2)	0.063 (2)	0.0186 (18)	0.0395 (18)	0.0105 (16)
O3	0.0433 (14)	0.0463 (16)	0.0648 (18)	0.0068 (12)	0.0173 (13)	−0.0028 (14)
N1	0.0452 (18)	0.0482 (19)	0.0533 (19)	0.0053 (15)	0.0216 (16)	0.0008 (15)
N2	0.077 (3)	0.080 (3)	0.124 (4)	−0.006 (3)	0.035 (3)	−0.046 (3)
C1	0.081 (4)	0.111 (5)	0.081 (4)	0.041 (4)	0.033 (3)	0.001 (3)
C2	0.079 (3)	0.072 (3)	0.065 (3)	0.020 (3)	0.036 (3)	0.005 (2)
C3	0.120 (5)	0.096 (4)	0.070 (3)	−0.002 (4)	0.060 (4)	0.004 (3)
C4	0.106 (4)	0.081 (4)	0.078 (4)	0.016 (3)	0.045 (3)	−0.001 (3)
C5	0.044 (2)	0.068 (3)	0.067 (3)	−0.004 (2)	0.018 (2)	−0.014 (2)
C6	0.048 (2)	0.041 (2)	0.042 (2)	−0.0015 (16)	0.0155 (17)	−0.0039 (16)
C7	0.041 (2)	0.043 (2)	0.058 (2)	−0.0001 (17)	0.0169 (18)	0.0001 (19)
C8	0.056 (3)	0.052 (3)	0.075 (3)	−0.002 (2)	0.031 (2)	−0.004 (2)
C9	0.063 (3)	0.059 (3)	0.121 (5)	0.001 (2)	0.051 (3)	−0.010 (3)
C10	0.053 (3)	0.055 (3)	0.142 (6)	0.008 (2)	0.020 (3)	−0.001 (3)
C11	0.065 (3)	0.070 (3)	0.093 (4)	0.005 (3)	−0.002 (3)	0.009 (3)
C12	0.062 (3)	0.060 (3)	0.062 (3)	0.001 (2)	0.010 (2)	−0.006 (2)

Geometric parameters (Å, º) top

Cl—C12	1.743 (5)	C3—H3A	0.9600
S—P	1.8966 (16)	C3—H3B	0.9600
P—O1	1.548 (3)	C3—H3C	0.9600
P—O2	1.566 (3)	C4—H4A	0.9700
P—O3	1.631 (3)	C4—H4B	0.9700
O1—C2	1.467 (5)	C5—C6	1.442 (6)
O2—C4	1.435 (6)	C6—C7	1.478 (5)
O3—N1	1.412 (4)	C7—C12	1.380 (6)
N1—C6	1.273 (5)	C7—C8	1.381 (6)
N2—C5	1.136 (6)	C8—C9	1.376 (7)
C1—C2	1.469 (7)	C8—H8A	0.9300
C1—H1B	0.9600	C9—C10	1.377 (9)
C1—H1C	0.9600	C9—H9A	0.9300
C1—H1D	0.9600	C10—C11	1.347 (9)
C2—H2A	0.9700	C10—H10A	0.9300
C2—H2B	0.9700	C11—C12	1.378 (7)
C3—C4	1.440 (7)	C11—H11A	0.9300

O1—P—O2	98.17 (17)	O2—C4—C3	110.1 (5)
O1—P—O3	98.71 (16)	O2—C4—H4A	109.6
O2—P—O3	104.07 (18)	C3—C4—H4A	109.6
O1—P—S	118.96 (13)	O2—C4—H4B	109.6
O2—P—S	119.75 (15)	C3—C4—H4B	109.6
O3—P—S	113.90 (12)	H4A—C4—H4B	108.2
C2—O1—P	122.8 (3)	N2—C5—C6	177.0 (5)
C4—O2—P	124.7 (3)	N1—C6—C5	122.6 (4)
N1—O3—P	111.1 (2)	N1—C6—C7	117.2 (3)
C6—N1—O3	111.4 (3)	C5—C6—C7	120.1 (4)
C2—C1—H1B	109.5	C12—C7—C8	118.0 (4)
C2—C1—H1C	109.5	C12—C7—C6	122.8 (4)
H1B—C1—H1C	109.5	C8—C7—C6	119.2 (4)
C2—C1—H1D	109.5	C9—C8—C7	121.1 (5)
H1B—C1—H1D	109.5	C9—C8—H8A	119.4
H1C—C1—H1D	109.5	C7—C8—H8A	119.4
O1—C2—C1	108.9 (4)	C8—C9—C10	119.4 (5)
O1—C2—H2A	109.9	C8—C9—H9A	120.3
C1—C2—H2A	109.9	C10—C9—H9A	120.3
O1—C2—H2B	109.9	C11—C10—C9	120.3 (5)
C1—C2—H2B	109.9	C11—C10—H10A	119.8
H2A—C2—H2B	108.3	C9—C10—H10A	119.8
C4—C3—H3A	109.5	C10—C11—C12	120.4 (5)
C4—C3—H3B	109.5	C10—C11—H11A	119.8
H3A—C3—H3B	109.5	C12—C11—H11A	119.8
C4—C3—H3C	109.5	C11—C12—C7	120.7 (5)
H3A—C3—H3C	109.5	C11—C12—Cl	119.7 (4)
H3B—C3—H3C	109.5	C7—C12—Cl	119.6 (4)

O2—P—O1—C2	174.0 (4)	C5—C6—C7—C12	58.7 (6)
O3—P—O1—C2	−80.3 (4)	N1—C6—C7—C8	55.6 (5)
S—P—O1—C2	43.2 (4)	C5—C6—C7—C8	−120.9 (5)
O1—P—O2—C4	−166.5 (4)	C12—C7—C8—C9	0.2 (7)
O3—P—O2—C4	92.3 (5)	C6—C7—C8—C9	179.9 (4)
S—P—O2—C4	−36.3 (5)	C7—C8—C9—C10	−0.7 (7)
O1—P—O3—N1	−177.2 (2)	C8—C9—C10—C11	0.2 (8)
O2—P—O3—N1	−76.5 (3)	C9—C10—C11—C12	0.6 (9)
S—P—O3—N1	55.7 (3)	C10—C11—C12—C7	−1.1 (8)
P—O3—N1—C6	179.0 (3)	C10—C11—C12—Cl	177.9 (5)
P—O1—C2—C1	−164.6 (4)	C8—C7—C12—C11	0.7 (7)
P—O2—C4—C3	170.6 (4)	C6—C7—C12—C11	−179.0 (4)
O3—N1—C6—C5	0.4 (5)	C8—C7—C12—Cl	−178.3 (3)
O3—N1—C6—C7	−176.0 (3)	C6—C7—C12—Cl	2.0 (6)
N1—C6—C7—C12	−124.7 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.97	2.58	3.396 (6)	142

Symmetry code: (i) x, −y+1/2, z+1/2.

Experimental details

Crystal data
Chemical formula	C₁₂H₁₄ClN₂O₃PS
M_r	332.73
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	293
a, b, c (Å)	10.518 (2), 20.215 (4), 7.9650 (16)
β (°)	110.11 (3)
V (Å³)	1590.3 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.48
Crystal size (mm)	0.30 × 0.20 × 0.10

Data collection
Diffractometer	Enraf–Nonius CAD-4 diffractometer
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.870, 0.954
No. of measured, independent and observed [I > 2σ(I)] reflections	2889, 2889, 1981
R_int	0.000
(sin θ/λ)_max (Å⁻¹)	0.602

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.192, 1.09
No. of reflections	2889
No. of parameters	183
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.31, −0.39

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1994), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C2—H2A···O1ⁱ	0.97	2.58	3.396 (6)	142.4

Symmetry code: (i) x, −y+1/2, z+1/2.

Acknowledgements

This work was supported by the Social Development Foundation of Jiangsu Province, China (No. BS2007060).

References

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ISSN: 2056-9890

Volume 65| Part 4| April 2009| Page o673

doi:10.1107/S160053680900693X

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

O,O′-Di­ethyl {(Z)-[(2-chloro­phen­yl)(cyano)methyl­ene]amino­­oxy}thio­phospho­nate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

O,O′-Diethyl {(Z)-[(2-chlorophenyl)(cyano)methylene]aminooxy}thiophosphonate