Diethyl {[5-(2,4-dichloro­phen­yl)-1,3,4-thia­diazol-2-ylamino](4-methoxy­phenyl)methyl}­phospho­nate

Wang, Y.; Wan, R.; Yin, L.-H.; Han, F.; Wang, P.

doi:10.1107/S1600536809012471

organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page o983

doi:10.1107/S1600536809012471

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Diethyl {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](4-methoxyphenyl)methyl}phosphonate

Yao Wang,^a Rong Wan,^a ^* Li-He Yin,^a Feng Han ^a and Peng Wang ^a

^aDepartment of Applied Chemistry, College of Science, Nanjing University of Technology, No.5 Xinmofan Road, Nanjing, Nanjing 210009, People's Republic of China
^*Correspondence e-mail: rwan@njut.edu.cn

(Received 12 February 2009; accepted 2 April 2009; online 8 April 2009)

The title compound, C₂₀H₂₂Cl₂N₃O₄PS, was synthesized by the reaction of N-(4-methoxybenzylidene)-5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-amine and diethyl phosphite. In the crystal, intermolecular C—H⋯O and N—H⋯O hydrogen bonds link the molecules.

Related literature

For applications of thiadiazole ligands, see: Nakagawa et al. (1996 ); Omar et al. (1986 ); Sato et al. (1991 ); Wang et al. (1999 ). For related structures, see: Wan et al. (2007 ); Yin et al. (2008 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

C₂₀H₂₂Cl₂N₃O₄PS
M_r = 502.34
Triclinic, $[P \overline 1]$
a = 9.7100 (19) Å
b = 11.825 (2) Å
c = 11.845 (2) Å
α = 98.74 (3)°
β = 112.16 (3)°
γ = 103.05 (3)°
V = 1183.9 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.46 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 = 0.874, T_max = 0.955
4592 measured reflections
4316 independent reflections
2864 reflections with I > 2σ(I)
R_int = 0.054
3 standard reflections every 200 reflections intensity decay: 1%

Refinement

R[F² > 2σ(F²)] = 0.069
wR(F²) = 0.157
S = 1.02
4316 reflections
277 parameters
H-atom parameters constrained
Δρ_max = 0.56 e Å⁻³
Δρ_min = −0.98 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3ⁱ	0.86	2.00	2.805 (5)	156
C10—H10A⋯O4ⁱⁱ	0.93	2.53	3.431 (7)	163
Symmetry codes: (i) -x+1, -y+1, -z+2; (ii) -x+2, -y+1, -z+3.

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989 ); 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/S1600536809012471/ez2165sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809012471/ez2165Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999). They can also be widely used in the field of medicine (Sato et al., 1991), such as for anti-cancer drugs (Omar et al., 1986).

We report here the crystal structure of the title compound,(I). The molecular structure of (I) is shown in Fig.1. Bond lengths are in the normal ranges (Allen et al., 1987). The dihedral angle between the C15—C20 and S/C13/N2/N3/C14 is 32.4 (3)°, which shows that these two aromatic rings are not in the same plane. This dihedral angle is bigger than other phosphonate compounds, which is 7.54 (3)° (Wan et al., 2007) and 5.3 (2)° (Yin et al., 2008). There are intermolecular C—H···O and N—H···O hydrogen bonds (Fig. 2), which form chains along the b axis in the crystal.

Related literature top

For applications of thiadiazole ligands, see: Nakagawa et al. (1996); Omar et al. (1986); Sato et al. (1991); Wang et al. (1999). For related structures, see: Wan et al. (2007); Yin et al. (2008). For bond-length data, see: Allen et al. (1987).

Experimental top

N-(4–methoxyphenyl)-5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-amine (2 mmol) and diethyl phosphite (5 mmol) were mixed in a 25 ml flask, and kept in an oil bath at 90°C for 6 h. After cooling, the crude product (I) precipitated and was filtered. Pure compound (I) was obtained by crystallization from ethanol (20 ml). Crystals of (I) suitable for X-ray diffraction were obtained by slow evaporation of an acetone solution.

Computing details top

Data collection: CAD-4 EXPRESS (Enraf–Nonius, 1989); cell refinement: CAD-4 EXPRESS (Enraf–Nonius, 1989); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. A view of the molecular structure of (I). Displacement ellipsoids are drawn at the 50% probability level.
	Fig. 2. Partial packing view showing the hydrogen-bonded network. Dashed lines indicate intermolecular C—H···O and N—H···O hydrogen bonds.

Diethyl {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](4- methoxyphenyl)methyl}phosphonate top

Crystal data top

C₂₀H₂₂Cl₂N₃O₄PS	F(000) = 520
M_r = 502.34	D_x = 1.409 Mg m⁻³
Triclinic, P1	Melting point: 59365 K
a = 9.7100 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 11.825 (2) Å	Cell parameters from 25 reflections
c = 11.845 (2) Å	θ = 9–13°
α = 98.74 (3)°	µ = 0.46 mm⁻¹
β = 112.16 (3)°	T = 293 K
γ = 103.05 (3)°	Block, colorless
V = 1183.9 (4) Å³	0.30 × 0.20 × 0.10 mm
Z = 2

Data collection top

Enraf–Nonius CAD-4 diffractometer	2864 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.054
Graphite monochromator	θ_max = 25.3°, θ_min = 1.8°
ω/2θ scans	h = 0→11
Absorption correction: ψ scan (North et al., 1968)	k = −14→13
T_min = 0.874, T_max = 0.955	l = −14→13
4592 measured reflections	3 standard reflections every 200 reflections
4316 independent reflections	intensity decay: 1%

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)] = 0.069	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0281P)² + 3.5816P] where P = (F_o² + 2F_c²)/3
4316 reflections	(Δ/σ)_max < 0.001
277 parameters	Δρ_max = 0.56 e Å⁻³
0 restraints	Δρ_min = −0.98 e Å⁻³

Crystal data top

C₂₀H₂₂Cl₂N₃O₄PS	γ = 103.05 (3)°
M_r = 502.34	V = 1183.9 (4) Å³
Triclinic, P1	Z = 2
a = 9.7100 (19) Å	Mo Kα radiation
b = 11.825 (2) Å	µ = 0.46 mm⁻¹
c = 11.845 (2) Å	T = 293 K
α = 98.74 (3)°	0.30 × 0.20 × 0.10 mm
β = 112.16 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2864 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.054
T_min = 0.874, T_max = 0.955	3 standard reflections every 200 reflections
4592 measured reflections	intensity decay: 1%
4316 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.069	0 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 1.02	Δρ_max = 0.56 e Å⁻³
4316 reflections	Δρ_min = −0.98 e Å⁻³
277 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
Cl1	0.1915 (3)	−0.0588 (2)	0.04559 (17)	0.1292 (9)
Cl2	0.60795 (15)	0.19354 (15)	0.51042 (15)	0.0812 (5)
S	0.45871 (13)	0.26753 (10)	0.68952 (11)	0.0518 (3)
P	0.28539 (13)	0.35163 (11)	1.04983 (12)	0.0508 (3)
N1	0.4404 (4)	0.3110 (3)	0.9121 (3)	0.0524 (10)
H1A	0.4934	0.3843	0.9247	0.063*
O1	0.1252 (4)	0.2999 (3)	0.9312 (4)	0.0754 (11)
C1	−0.0855 (9)	0.3620 (8)	0.8045 (8)	0.112
H1B	−0.1550	0.2881	0.7427	0.168*
H1C	−0.1008	0.4286	0.7694	0.168*
H1D	−0.1069	0.3689	0.8777	0.168*
N2	0.2791 (5)	0.1297 (3)	0.7581 (3)	0.0541 (10)
O2	0.2564 (4)	0.2931 (3)	1.1510 (3)	0.0698 (10)
C2	0.0749 (9)	0.3624 (9)	0.8405 (8)	0.123 (3)
H2A	0.0851	0.3269	0.7658	0.148*
H2B	0.1427	0.4451	0.8733	0.148*
O3	0.3460 (4)	0.4837 (3)	1.0857 (3)	0.0621 (9)
N3	0.2468 (4)	0.0703 (3)	0.6370 (3)	0.0541 (10)
C3	0.2866 (11)	0.4070 (7)	1.3512 (7)	0.127 (3)
H3A	0.3578	0.3667	1.3943	0.191*
H3B	0.2285	0.4241	1.3981	0.191*
H3C	0.3443	0.4808	1.3440	0.191*
O4	0.9613 (4)	0.3317 (3)	1.4496 (4)	0.0826 (12)
C4	0.1777 (9)	0.3289 (7)	1.2240 (7)	0.100 (2)
H4A	0.1134	0.2577	1.2320	0.120*
H4B	0.1091	0.3715	1.1796	0.120*
C5	0.4108 (5)	0.2749 (4)	1.0145 (4)	0.0461 (10)
H5A	0.3525	0.1888	0.9834	0.055*
C6	0.5616 (5)	0.2897 (4)	1.1290 (4)	0.0454 (10)
C7	0.6196 (5)	0.1950 (4)	1.1435 (5)	0.0572 (12)
H7A	0.5671	0.1221	1.0821	0.069*
C8	0.7548 (5)	0.2052 (4)	1.2475 (5)	0.0583 (12)
H8A	0.7942	0.1406	1.2546	0.070*
C9	0.8308 (5)	0.3130 (4)	1.3412 (5)	0.0569 (12)
C10	0.7780 (6)	0.4085 (4)	1.3276 (5)	0.0735 (16)
H10A	0.8300	0.4811	1.3896	0.088*
C11	0.6447 (6)	0.3977 (4)	1.2197 (5)	0.0670 (15)
H11A	0.6114	0.4647	1.2088	0.080*
C13	0.3876 (5)	0.2336 (4)	0.7974 (4)	0.0441 (10)
C14	0.3304 (5)	0.1296 (4)	0.5888 (4)	0.0418 (9)
C15	0.3017 (5)	0.0854 (4)	0.4561 (4)	0.0468 (10)
C16	0.1499 (5)	0.0152 (4)	0.3671 (4)	0.0515 (11)
H16A	0.0708	−0.0020	0.3939	0.062*
C17	0.1154 (7)	−0.0281 (5)	0.2443 (5)	0.0700 (15)
H17A	0.0133	−0.0731	0.1882	0.084*
C18	0.2304 (8)	−0.0064 (5)	0.2005 (5)	0.0770 (17)
C19	0.3822 (8)	0.0635 (6)	0.2868 (6)	0.0856 (19)
H19A	0.4608	0.0802	0.2595	0.103*
C20	0.4161 (6)	0.1077 (4)	0.4115 (5)	0.0553 (12)
C12	1.0077 (7)	0.2351 (6)	1.4818 (7)	0.089 (2)
H12A	0.9175	0.1691	1.4638	0.133*
H12B	1.0760	0.2571	1.5703	0.133*
H12C	1.0619	0.2116	1.4339	0.133*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.1449 (18)	0.1336 (17)	0.0748 (11)	−0.0205 (14)	0.0628 (12)	−0.0134 (10)
Cl2	0.0454 (7)	0.0980 (11)	0.0881 (10)	0.0027 (7)	0.0353 (7)	0.0024 (8)
S	0.0407 (6)	0.0465 (6)	0.0540 (6)	−0.0047 (5)	0.0178 (5)	0.0081 (5)
P	0.0381 (6)	0.0437 (6)	0.0588 (7)	0.0023 (5)	0.0147 (5)	0.0120 (5)
N1	0.052 (2)	0.0392 (19)	0.045 (2)	−0.0059 (16)	0.0124 (17)	0.0063 (16)
O1	0.0436 (19)	0.071 (2)	0.083 (3)	0.0092 (17)	0.0032 (18)	0.017 (2)
C1	0.112	0.112	0.112	0.035	0.048	0.029
N2	0.058 (2)	0.043 (2)	0.049 (2)	−0.0044 (17)	0.0235 (18)	0.0071 (16)
O2	0.076 (2)	0.061 (2)	0.080 (2)	0.0123 (19)	0.045 (2)	0.0251 (19)
C2	0.108 (6)	0.143 (7)	0.086 (5)	0.030 (6)	0.012 (4)	0.030 (5)
O3	0.055 (2)	0.0462 (18)	0.077 (2)	0.0073 (15)	0.0238 (17)	0.0175 (16)
N3	0.052 (2)	0.046 (2)	0.049 (2)	−0.0017 (17)	0.0170 (18)	0.0078 (17)
C3	0.167 (9)	0.098 (6)	0.123 (7)	0.036 (6)	0.073 (7)	0.027 (5)
O4	0.060 (2)	0.057 (2)	0.091 (3)	0.0136 (18)	−0.007 (2)	0.019 (2)
C4	0.112 (6)	0.104 (5)	0.117 (6)	0.041 (5)	0.076 (5)	0.037 (5)
C5	0.045 (2)	0.037 (2)	0.046 (2)	−0.0004 (18)	0.0152 (19)	0.0106 (18)
C6	0.035 (2)	0.040 (2)	0.053 (2)	0.0051 (18)	0.0130 (19)	0.0170 (19)
C7	0.049 (3)	0.046 (3)	0.068 (3)	0.010 (2)	0.023 (2)	0.005 (2)
C8	0.042 (3)	0.055 (3)	0.073 (3)	0.019 (2)	0.017 (2)	0.017 (2)
C9	0.037 (2)	0.047 (3)	0.071 (3)	0.008 (2)	0.010 (2)	0.015 (2)
C10	0.060 (3)	0.042 (3)	0.077 (4)	0.009 (2)	−0.006 (3)	0.005 (2)
C11	0.058 (3)	0.042 (3)	0.069 (3)	0.015 (2)	−0.003 (2)	0.005 (2)
C13	0.031 (2)	0.041 (2)	0.049 (2)	0.0038 (17)	0.0097 (18)	0.0123 (18)
C14	0.032 (2)	0.038 (2)	0.052 (2)	0.0068 (17)	0.0179 (18)	0.0104 (18)
C15	0.044 (2)	0.039 (2)	0.055 (2)	0.0091 (18)	0.021 (2)	0.0109 (19)
C16	0.045 (2)	0.046 (2)	0.051 (2)	0.001 (2)	0.018 (2)	0.003 (2)
C17	0.072 (4)	0.055 (3)	0.059 (3)	−0.008 (3)	0.022 (3)	0.005 (2)
C18	0.091 (4)	0.062 (3)	0.071 (3)	0.001 (3)	0.044 (3)	0.008 (3)
C19	0.087 (4)	0.081 (4)	0.091 (4)	0.002 (3)	0.060 (4)	0.006 (3)
C20	0.051 (3)	0.052 (3)	0.063 (3)	0.006 (2)	0.032 (2)	0.008 (2)
C12	0.063 (4)	0.073 (4)	0.110 (5)	0.027 (3)	0.007 (3)	0.037 (4)

Geometric parameters (Å, º) top

Cl1—C18	1.709 (6)	C4—H4A	0.9700
Cl2—C20	1.736 (5)	C4—H4B	0.9700
S—C13	1.723 (4)	C5—C6	1.526 (6)
S—C14	1.733 (4)	C5—H5A	0.9800
P—O3	1.469 (3)	C6—C7	1.368 (6)
P—O2	1.553 (4)	C6—C11	1.378 (6)
P—O1	1.559 (4)	C7—C8	1.385 (7)
P—C5	1.803 (5)	C7—H7A	0.9300
N1—C13	1.354 (5)	C8—C9	1.388 (7)
N1—C5	1.449 (5)	C8—H8A	0.9300
N1—H1A	0.8600	C9—C10	1.348 (7)
O1—C2	1.395 (9)	C10—C11	1.398 (7)
C1—C2	1.450 (8)	C10—H10A	0.9300
C1—H1B	0.9600	C11—H11A	0.9300
C1—H1C	0.9600	C14—C15	1.475 (6)
C1—H1D	0.9600	C15—C20	1.391 (6)
N2—C13	1.306 (5)	C15—C16	1.408 (6)
N2—N3	1.380 (5)	C16—C17	1.349 (7)
O2—C4	1.430 (7)	C16—H16A	0.9300
C2—H2A	0.9700	C17—C18	1.388 (8)
C2—H2B	0.9700	C17—H17A	0.9300
N3—C14	1.301 (5)	C18—C19	1.399 (8)
C3—C4	1.475 (7)	C19—C20	1.373 (7)
C3—H3A	0.9600	C19—H19A	0.9300
C3—H3B	0.9600	C12—H12A	0.9600
C3—H3C	0.9600	C12—H12B	0.9600
O4—C9	1.365 (6)	C12—H12C	0.9600
O4—C12	1.374 (7)

C13—S—C14	87.0 (2)	C11—C6—C5	121.9 (4)
O3—P—O2	116.2 (2)	C6—C7—C8	121.6 (5)
O3—P—O1	113.2 (2)	C6—C7—H7A	119.2
O2—P—O1	104.1 (2)	C8—C7—H7A	119.2
O3—P—C5	115.3 (2)	C7—C8—C9	119.3 (5)
O2—P—C5	101.5 (2)	C7—C8—H8A	120.4
O1—P—C5	105.2 (2)	C9—C8—H8A	120.4
C13—N1—C5	122.3 (3)	C10—C9—O4	115.6 (4)
C13—N1—H1A	118.8	C10—C9—C8	120.2 (5)
C5—N1—H1A	118.8	O4—C9—C8	124.2 (4)
C2—O1—P	122.8 (4)	C9—C10—C11	119.6 (5)
C2—C1—H1B	109.5	C9—C10—H10A	120.2
C2—C1—H1C	109.5	C11—C10—H10A	120.2
H1B—C1—H1C	109.5	C6—C11—C10	121.4 (5)
C2—C1—H1D	109.5	C6—C11—H11A	119.3
H1B—C1—H1D	109.5	C10—C11—H11A	119.3
H1C—C1—H1D	109.5	N2—C13—N1	124.0 (4)
C13—N2—N3	111.7 (4)	N2—C13—S	114.6 (3)
C4—O2—P	126.3 (4)	N1—C13—S	121.4 (3)
O1—C2—C1	113.6 (7)	N3—C14—C15	121.0 (4)
O1—C2—H2A	108.8	N3—C14—S	113.4 (3)
C1—C2—H2A	108.8	C15—C14—S	125.3 (3)
O1—C2—H2B	108.8	C20—C15—C16	116.7 (4)
C1—C2—H2B	108.8	C20—C15—C14	124.2 (4)
H2A—C2—H2B	107.7	C16—C15—C14	119.1 (4)
C14—N3—N2	113.4 (3)	C17—C16—C15	122.2 (5)
C4—C3—H3A	109.5	C17—C16—H16A	118.9
C4—C3—H3B	109.5	C15—C16—H16A	118.9
H3A—C3—H3B	109.5	C16—C17—C18	120.8 (5)
C4—C3—H3C	109.5	C16—C17—H17A	119.6
H3A—C3—H3C	109.5	C18—C17—H17A	119.6
H3B—C3—H3C	109.5	C17—C18—C19	118.2 (5)
C9—O4—C12	119.5 (4)	C17—C18—Cl1	122.4 (5)
O2—C4—C3	112.8 (6)	C19—C18—Cl1	119.5 (4)
O2—C4—H4A	109.0	C20—C19—C18	120.6 (5)
C3—C4—H4A	109.0	C20—C19—H19A	119.7
O2—C4—H4B	109.0	C18—C19—H19A	119.7
C3—C4—H4B	109.0	C19—C20—C15	121.5 (5)
H4A—C4—H4B	107.8	C19—C20—Cl2	116.8 (4)
N1—C5—C6	112.2 (3)	C15—C20—Cl2	121.7 (4)
N1—C5—P	109.5 (3)	O4—C12—H12A	109.5
C6—C5—P	113.9 (3)	O4—C12—H12B	109.5
N1—C5—H5A	106.9	H12A—C12—H12B	109.5
C6—C5—H5A	106.9	O4—C12—H12C	109.5
P—C5—H5A	106.9	H12A—C12—H12C	109.5
C7—C6—C11	117.8 (4)	H12B—C12—H12C	109.5
C7—C6—C5	120.3 (4)

O3—P—O1—C2	24.0 (6)	C7—C6—C11—C10	−4.4 (8)
O2—P—O1—C2	151.1 (6)	C5—C6—C11—C10	176.5 (5)
C5—P—O1—C2	−102.7 (6)	C9—C10—C11—C6	2.9 (10)
O3—P—O2—C4	46.8 (6)	N3—N2—C13—N1	179.2 (4)
O1—P—O2—C4	−78.3 (5)	N3—N2—C13—S	0.2 (5)
C5—P—O2—C4	172.6 (5)	C5—N1—C13—N2	15.7 (7)
P—O1—C2—C1	−133.6 (6)	C5—N1—C13—S	−165.4 (3)
C13—N2—N3—C14	0.1 (6)	C14—S—C13—N2	−0.3 (4)
P—O2—C4—C3	−98.2 (7)	C14—S—C13—N1	−179.3 (4)
C13—N1—C5—C6	118.7 (4)	N2—N3—C14—C15	−174.2 (4)
C13—N1—C5—P	−113.8 (4)	N2—N3—C14—S	−0.4 (5)
O3—P—C5—N1	−58.4 (3)	C13—S—C14—N3	0.4 (4)
O2—P—C5—N1	175.2 (3)	C13—S—C14—C15	173.9 (4)
O1—P—C5—N1	67.0 (3)	N3—C14—C15—C20	−150.9 (5)
O3—P—C5—C6	68.1 (3)	S—C14—C15—C20	36.0 (7)
O2—P—C5—C6	−58.3 (3)	N3—C14—C15—C16	28.6 (7)
O1—P—C5—C6	−166.5 (3)	S—C14—C15—C16	−144.4 (4)
N1—C5—C6—C7	−93.9 (5)	C20—C15—C16—C17	−0.5 (7)
P—C5—C6—C7	141.0 (4)	C14—C15—C16—C17	180.0 (5)
N1—C5—C6—C11	85.2 (6)	C15—C16—C17—C18	1.0 (9)
P—C5—C6—C11	−39.9 (6)	C16—C17—C18—C19	−1.2 (9)
C11—C6—C7—C8	1.9 (7)	C16—C17—C18—Cl1	−179.6 (5)
C5—C6—C7—C8	−178.9 (4)	C17—C18—C19—C20	0.9 (10)
C6—C7—C8—C9	1.9 (8)	Cl1—C18—C19—C20	179.3 (5)
C12—O4—C9—C10	168.9 (6)	C18—C19—C20—C15	−0.4 (10)
C12—O4—C9—C8	−12.1 (9)	C18—C19—C20—Cl2	−179.9 (5)
C7—C8—C9—C10	−3.5 (8)	C16—C15—C20—C19	0.2 (8)
C7—C8—C9—O4	177.5 (5)	C14—C15—C20—C19	179.7 (5)
O4—C9—C10—C11	−179.8 (5)	C16—C15—C20—Cl2	179.6 (4)
C8—C9—C10—C11	1.1 (9)	C14—C15—C20—Cl2	−0.8 (7)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3ⁱ	0.86	2.00	2.805 (5)	156
C10—H10A···O4ⁱⁱ	0.93	2.53	3.431 (7)	163

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+3.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₂Cl₂N₃O₄PS
M_r	502.34
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.7100 (19), 11.825 (2), 11.845 (2)
α, β, γ (°)	98.74 (3), 112.16 (3), 103.05 (3)
V (Å³)	1183.9 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.46
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	0.874, 0.955
No. of measured, independent and observed [I > 2σ(I)] reflections	4592, 4316, 2864
R_int	0.054
(sin θ/λ)_max (Å⁻¹)	0.601

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.069, 0.157, 1.02
No. of reflections	4316
No. of parameters	277
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.56, −0.98

Computer programs: CAD-4 EXPRESS (Enraf–Nonius, 1989), CAD-4 EXPRESS (Enraf–Nonius, 1989), 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
N1—H1A···O3ⁱ	0.8600	2.0000	2.805 (5)	156.00
C10—H10A···O4ⁱⁱ	0.9300	2.5300	3.431 (7)	163.00

Symmetry codes: (i) −x+1, −y+1, −z+2; (ii) −x+2, −y+1, −z+3.

Acknowledgements

The authors thank Professor Hua-qin Wang of the Analysis Centre, Nanjing University, for carrying out the X-ray crystallographic analysis.

References

Allen, F. H., Kennard, O., Watson, D. G., Brammer, L., Orpen, A. G. & Taylor, R. (1987). J. Chem. Soc. Perkin Trans. 2, pp. S1–19. CrossRef Web of Science Google Scholar
Enraf–Nonius (1989). CAD-4 Software. Enraf–Nonius, Delft, The Netherlands. Google Scholar
Harms, K. & Wocadlo, S. (1995). XCAD4. University of Marburg, Germany. Google Scholar
Nakagawa, Y., Nishimura, K., Izumi, K., Kinoshita, K., Kimura, T. & Kurihara, N. (1996). J. Pestic. Sci. 21, 195–201. CrossRef CAS Google Scholar
North, A. C. T., Phillips, D. C. & Mathews, F. S. (1968). Acta Cryst. A24, 351–359. CrossRef IUCr Journals Web of Science Google Scholar
Omar, A., Mohsen, M. E. & Wafa, O. A. (1986). J. Heterocycl. Chem. 23, 1339–1341. CrossRef CAS Google Scholar
Sato, H., Fukuda, K. & Ito, K. (1991). Japanese Patent JP 03 287 585. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Wan, R., Han, F., Zhang, J., Yin, L. & Wang, J. (2007). Acta Cryst. E63, o4158. Web of Science CSD CrossRef IUCr Journals Google Scholar
Wang, Y. G., Cao, L., Yan, J., Ye, W. F., Zhou, Q. C. & Lu, B. X. (1999). Chem. J. Chin. Univ., 20, 1903–1905. CAS Google Scholar
Yin, L.-H., Wan, R., Han, F., Wang, B. & Wang, J.-T. (2008). Acta Cryst. E64, o1376. Web of Science CSD CrossRef IUCr Journals Google Scholar

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Volume 65| Part 5| May 2009| Page o983

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

Di­ethyl {[5-(2,4-di­chloro­phen­yl)-1,3,4-thia­diazol-2-ylamino](4-meth­oxy­phenyl)methyl}­phospho­nate

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

Diethyl {[5-(2,4-dichlorophenyl)-1,3,4-thiadiazol-2-ylamino](4-methoxyphenyl)methyl}phosphonate