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

Yin, L.-H.; Wan, R.; Han, F.; Wang, B.; Wang, J.-T.

doi:10.1107/S1600536808017364

organic compounds

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ISSN: 2056-9890

Volume 64| Part 8| August 2008| Page o1376

doi:10.1107/S1600536808017364

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

Li-He Yin,^a Rong Wan,^a ^* Feng Han,^a Bin Wang ^a and Jin-Tang Wang ^a

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

(Received 6 March 2008; accepted 9 June 2008; online 5 July 2008)

The title compound, C₂₀H₂₃N₄O₆PS, was synthesized by the reaction of N-(4-methoxybenzylidene)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine and diethyl phosphite. The thiadiazole and nitro-substituted phenyl rings in the molecule are approximately coplanar, the dihedral angle being 5.3 (2)°. The dihedral angle formed by the mean plane through all non-H atoms of both the thiadiazole and the nitro-substituted phenyl ring with the plane of the methoxy-substituted phenyl ring is 48.9 (2)°. In the crystal structure, molecules form centrosymmetric dimers as a result of N—H⋯O bonds involving amine H and phosphine oxide O atoms.

Related literature

For related literature, see: Nakagawa et al. (1996 ); Wang et al. (1999 ).

Experimental

Crystal data

C₂₀H₂₃N₄O₆PS
M_r = 478.45
Monoclinic, P 2₁ /n
a = 11.481 (2) Å
b = 19.426 (4) Å
c = 11.960 (2) Å
β = 117.08 (3)°
V = 2375.0 (10) Å³
Z = 4
Mo Kα radiation
μ = 0.25 mm⁻¹
T = 298 (2) 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 = 0.930, T_max = 0.976
4497 measured reflections
4276 independent reflections
2330 reflections with I > 2σ(I)
R_int = 0.064
3 standard reflections every 200 reflections intensity decay: none

Refinement

R[F² > 2σ(F²)] = 0.068
wR(F²) = 0.146
S = 1.03
4276 reflections
289 parameters
H-atom parameters constrained
Δρ_max = 0.30 e Å⁻³
Δρ_min = −0.21 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O5ⁱ	0.86	1.94	2.782 (6)	165
Symmetry code: (i) -x, -y, -z.

Data collection: CAD-4 Software (Enraf–Nonius,1989 ); cell refinement: CAD-4 Software; 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/S1600536808017364/ya2071sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536808017364/ya2071Isup2.hkl

checkCIF report

Comment top

1,3,4-Thiadiazole derivatives represent an interesting class of biologically important compounds, which often exhibit insecticidal, fungicidal and other biological activities (Nakagawa et al., 1996; Wang et al., 1999).

We report here the X-ray structure of the title compound,(I)(Fig. 1). The thiadiazole and nitro-substituted phenyl rings in the molecule of (I) are approximately coplanar: the dihedral angle between the C11—C16 and S/C10/N2/N3/C9 planes being 5.3 (2)°, the maximum deviation from the mean plane N1/C9/C10/N2/N3/S/C11/C12/C13/C14/C15/C16 does not exceed 0.11 Å. The dihedral angle formed by the latter plane with the plane of the methoxy- substituted phenyl ring C2—C7 is equal to 48.9 (2) °.

In the crystal structure, molecules of (I) form centrosymmetric dimers due to N—H···O bonds involving amine hydrogen and phosphineoxide oxygen [N1···O5ⁱ 2.782 (6) Å; symmetry code (i): -x, -y, -z].

Related literature top

For related literature, see: Nakagawa et al. (1996); Wang et al. (1999).

Experimental top

N-(4-methoxybenzylidene)-5-(4-nitrophenyl)-1,3,4-thiadiazol-2-amine (2 mmol) and diethyl phosphite (5 mmol) were mixed in a 25 ml flask (without any solvent),and kept in the oil bath at 90°C for 6 h. After cooling, the crude product (I) precipitated and was filtered. Pure compound (I) was obtained by recrystallization 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 Software (Enraf–Nonius,1989); cell refinement: CAD-4 Software (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. Molecular structure of (I). Displacement ellipsoids are drawn at the 30% probability level. H atoms are shown as small circles of arbitrary radius.

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

Crystal data top

C₂₀H₂₃N₄O₆PS	F(000) = 1000
M_r = 478.45	D_x = 1.338 Mg m⁻³
Monoclinic, P2₁/n	Melting point: 476 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 11.481 (2) Å	Cell parameters from 25 reflections
b = 19.426 (4) Å	θ = 9–13°
c = 11.960 (2) Å	µ = 0.25 mm⁻¹
β = 117.08 (3)°	T = 298 K
V = 2375.0 (10) Å³	Block, light yellow
Z = 4	0.30 × 0.20 × 0.10 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	2330 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.064
Graphite monochromator	θ_max = 25.2°, θ_min = 2.0°
ω/2θ scans	h = −13→12
Absorption correction: ψ scan (North et al., 1968)	k = 0→23
T_min = 0.930, T_max = 0.976	l = 0→14
4497 measured reflections	3 standard reflections every 200 reflections
4276 independent reflections	intensity decay: none

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)] = 0.068	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	w = 1/[σ²(F_o²) + (0.03P)² + 3.2P] where P = (F_o² + 2F_c²)/3
4276 reflections	(Δ/σ)_max < 0.001
289 parameters	Δρ_max = 0.30 e Å⁻³
0 restraints	Δρ_min = −0.21 e Å⁻³

Crystal data top

C₂₀H₂₃N₄O₆PS	V = 2375.0 (10) Å³
M_r = 478.45	Z = 4
Monoclinic, P2₁/n	Mo Kα radiation
a = 11.481 (2) Å	µ = 0.25 mm⁻¹
b = 19.426 (4) Å	T = 298 K
c = 11.960 (2) Å	0.30 × 0.20 × 0.10 mm
β = 117.08 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	2330 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.064
T_min = 0.930, T_max = 0.976	3 standard reflections every 200 reflections
4497 measured reflections	intensity decay: none
4276 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.068	0 restraints
wR(F²) = 0.146	H-atom parameters constrained
S = 1.03	Δρ_max = 0.30 e Å⁻³
4276 reflections	Δρ_min = −0.21 e Å⁻³
289 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
S	0.11752 (9)	0.17107 (5)	−0.10907 (11)	0.0688 (4)
P	0.23008 (11)	−0.02508 (6)	0.20206 (12)	0.0738 (4)
N1	0.1765 (3)	0.04373 (17)	−0.0120 (3)	0.0700 (10)
H1A	0.0966	0.0342	−0.0631	0.084*
O1	0.2443 (4)	−0.2713 (2)	−0.1562 (4)	0.1097 (12)
C1	0.1296 (7)	−0.2920 (3)	−0.2318 (6)	0.113 (2)
H1B	0.1350	−0.3368	−0.2631	0.185*
H1C	0.0906	−0.2603	−0.3007	0.185*
H1D	0.0769	−0.2945	−0.1885	0.185*
N2	0.3560 (3)	0.19583 (16)	0.0431 (3)	0.0639 (9)
O2	0.3525 (4)	0.53251 (19)	−0.1632 (4)	0.154 (2)
C2	0.2280 (7)	−0.2053 (3)	−0.1134 (7)	0.108 (2)
N3	0.3379 (3)	0.12947 (16)	0.0636 (3)	0.0699 (10)
O3	0.1531 (4)	0.52326 (17)	−0.2953 (4)	0.1379 (17)
C3	0.1235 (6)	−0.1701 (3)	−0.1297 (6)	0.1072 (19)
H3B	0.0416	−0.1890	−0.1795	0.129*
N4	0.2539 (5)	0.4987 (2)	−0.2075 (4)	0.0979 (14)
C4	0.1299 (4)	−0.1052 (2)	−0.0755 (5)	0.0913 (16)
H4A	0.0530	−0.0821	−0.0911	0.110*
O4	0.2896 (4)	0.04106 (19)	0.2851 (4)	0.1017 (13)
O5	0.0918 (3)	−0.03805 (17)	0.1673 (3)	0.0877 (10)
C5	0.2466 (4)	−0.0758 (2)	−0.0010 (4)	0.0624 (11)
O6	0.3218 (3)	−0.0846 (2)	0.2736 (3)	0.1005 (12)
C6	0.3601 (5)	−0.1129 (3)	0.0189 (5)	0.0917 (16)
H6A	0.4426	−0.0944	0.0683	0.110*
C7	0.3476 (6)	−0.1768 (3)	−0.0357 (6)	0.0997 (17)
H7A	0.4229	−0.2017	−0.0194	0.120*
C8	0.2618 (4)	−0.0111 (2)	0.0683 (4)	0.0660 (12)
H8A	0.3527	0.0042	0.1000	0.079*
C9	0.2198 (3)	0.1078 (2)	−0.0078 (4)	0.0581 (10)
C10	0.2513 (3)	0.22694 (18)	−0.0425 (4)	0.0560 (10)
C11	0.2495 (3)	0.29723 (19)	−0.0822 (3)	0.0553 (10)
C12	0.1363 (3)	0.32734 (19)	−0.1726 (4)	0.0656 (12)
H12A	0.0584	0.3026	−0.2044	0.079*
C13	0.1361 (4)	0.3941 (2)	−0.2172 (4)	0.0795 (14)
H13A	0.0599	0.4130	−0.2800	0.095*
C14	0.2518 (4)	0.4315 (2)	−0.1658 (4)	0.0774 (13)
C15	0.3662 (4)	0.4028 (2)	−0.0697 (4)	0.0732 (13)
H15A	0.4426	0.4287	−0.0333	0.088*
C16	0.3654 (3)	0.3367 (2)	−0.0296 (4)	0.0698 (12)
H16A	0.4417	0.3177	0.0328	0.084*
C17	0.2907 (7)	0.1293 (4)	0.4169 (7)	0.118 (3)
H17A	0.2690	0.1414	0.4830	0.177*
H17B	0.2346	0.1539	0.3418	0.177*
H17C	0.3802	0.1413	0.4413	0.177*
C18	0.2731 (7)	0.0561 (3)	0.3935 (7)	0.124 (2)
H18A	0.3368	0.0309	0.4653	0.151*
H18B	0.1863	0.0425	0.3798	0.151*
C19	0.2659 (6)	−0.2016 (3)	0.2448 (6)	0.121 (2)
H19A	0.2385	−0.2397	0.2783	0.182*
H19B	0.3481	−0.2123	0.2461	0.182*
H19C	0.2014	−0.1930	0.1600	0.182*
C20	0.2802 (6)	−0.1418 (3)	0.3193 (6)	0.1095 (18)
H20A	0.1973	−0.1313	0.3184	0.131*
H20B	0.3437	−0.1510	0.4055	0.131*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
S	0.0357 (5)	0.0488 (6)	0.0856 (8)	−0.0028 (5)	−0.0039 (5)	0.0022 (6)
P	0.0516 (7)	0.0748 (8)	0.0725 (8)	0.0008 (6)	0.0087 (6)	−0.0038 (7)
N1	0.0389 (18)	0.057 (2)	0.085 (2)	−0.0010 (16)	0.0027 (17)	0.0111 (18)
O1	0.118 (3)	0.102 (3)	0.107 (3)	0.011 (3)	0.094 (3)	−0.013 (2)
C1	0.119 (5)	0.123 (6)	0.110 (5)	0.008 (5)	0.068 (5)	0.014 (4)
N2	0.0360 (17)	0.051 (2)	0.073 (2)	−0.0047 (15)	−0.0024 (15)	0.0008 (17)
O2	0.135 (4)	0.066 (2)	0.163 (4)	−0.040 (2)	−0.018 (3)	0.012 (2)
C2	0.137 (6)	0.048 (3)	0.168 (6)	−0.007 (3)	0.095 (5)	−0.018 (3)
N3	0.0392 (18)	0.050 (2)	0.087 (2)	0.0054 (15)	−0.0002 (17)	0.0068 (18)
O3	0.130 (3)	0.059 (2)	0.148 (4)	0.018 (2)	−0.003 (3)	0.015 (2)
C3	0.100 (4)	0.073 (4)	0.150 (5)	−0.031 (3)	0.058 (4)	−0.039 (4)
N4	0.091 (3)	0.057 (3)	0.096 (3)	−0.002 (2)	0.001 (3)	0.001 (2)
C4	0.066 (3)	0.058 (3)	0.124 (4)	−0.014 (2)	0.020 (3)	−0.015 (3)
O4	0.117 (3)	0.097 (3)	0.113 (3)	−0.037 (2)	0.036 (3)	−0.049 (2)
O5	0.0603 (19)	0.104 (2)	0.091 (2)	0.0058 (17)	0.0280 (17)	0.0085 (19)
C5	0.055 (2)	0.050 (2)	0.082 (3)	−0.001 (2)	0.031 (2)	0.000 (2)
O6	0.068 (2)	0.101 (3)	0.104 (3)	0.019 (2)	0.0099 (19)	0.043 (2)
C6	0.073 (3)	0.080 (4)	0.136 (5)	0.002 (3)	0.060 (3)	−0.008 (3)
C7	0.116 (5)	0.062 (3)	0.151 (5)	0.024 (3)	0.086 (4)	0.017 (3)
C8	0.036 (2)	0.057 (3)	0.096 (3)	0.0057 (18)	0.023 (2)	0.006 (2)
C9	0.032 (2)	0.051 (2)	0.072 (3)	0.0090 (17)	0.0069 (18)	0.006 (2)
C10	0.0327 (19)	0.042 (2)	0.072 (3)	−0.0039 (16)	0.0058 (18)	−0.0128 (19)
C11	0.040 (2)	0.052 (2)	0.055 (2)	0.0013 (17)	0.0056 (17)	−0.0093 (19)
C12	0.041 (2)	0.041 (2)	0.076 (3)	−0.0024 (17)	−0.0062 (19)	0.001 (2)
C13	0.055 (3)	0.046 (2)	0.089 (3)	−0.002 (2)	−0.009 (2)	0.012 (2)
C14	0.063 (3)	0.052 (3)	0.084 (3)	0.000 (2)	0.006 (2)	−0.002 (2)
C15	0.046 (2)	0.065 (3)	0.085 (3)	−0.009 (2)	0.009 (2)	0.003 (2)
C16	0.039 (2)	0.051 (2)	0.080 (3)	0.0010 (18)	−0.0073 (19)	0.004 (2)
C17	0.129 (7)	0.116 (7)	0.109 (6)	0.002 (6)	−0.037 (5)	−0.029 (6)
C18	0.136 (6)	0.108 (5)	0.127 (6)	−0.003 (4)	0.071 (5)	−0.018 (4)
C19	0.124 (5)	0.111 (5)	0.133 (5)	−0.007 (4)	0.063 (4)	−0.004 (4)
C20	0.106 (4)	0.113 (5)	0.110 (5)	0.010 (4)	0.050 (4)	0.025 (4)

Geometric parameters (Å, º) top

S—C10	1.749 (3)	O6—C20	1.415 (6)
S—C9	1.750 (4)	C6—C7	1.381 (7)
P—O5	1.468 (3)	C6—H6A	0.9300
P—O6	1.535 (3)	C7—H7A	0.9300
P—O4	1.577 (3)	C8—H8A	0.9800
P—C8	1.816 (5)	C10—C11	1.442 (5)
N1—C9	1.332 (5)	C11—C12	1.386 (5)
N1—C8	1.469 (5)	C11—C16	1.411 (5)
N1—H1A	0.8600	C12—C13	1.402 (5)
O1—C1	1.276 (6)	C12—H12A	0.9300
O1—C2	1.423 (6)	C13—C14	1.387 (5)
C1—H1B	0.9600	C13—H13A	0.9300
C1—H1C	0.9600	C14—C15	1.408 (5)
C1—H1D	0.9600	C15—C16	1.373 (5)
N2—C10	1.318 (4)	C15—H15A	0.9300
N2—N3	1.346 (4)	C16—H16A	0.9300
O2—N4	1.203 (5)	C17—C18	1.446 (8)
C2—C3	1.316 (7)	C17—H17A	0.9600
C2—C7	1.376 (7)	C17—H17B	0.9600
N3—C9	1.301 (4)	C17—H17C	0.9600
O3—N4	1.251 (5)	C18—H18A	0.9700
C3—C4	1.404 (6)	C18—H18B	0.9700
C3—H3B	0.9300	C19—C20	1.426 (7)
N4—C14	1.402 (6)	C19—H19A	0.9600
C4—C5	1.352 (5)	C19—H19B	0.9600
C4—H4A	0.9300	C19—H19C	0.9600
O4—C18	1.423 (7)	C20—H20A	0.9700
C5—C6	1.412 (6)	C20—H20B	0.9700
C5—C8	1.471 (5)

C10—S—C9	87.00 (18)	N3—C9—N1	125.9 (3)
O5—P—O6	114.1 (2)	N3—C9—S	113.4 (3)
O5—P—O4	114.9 (2)	N1—C9—S	120.6 (3)
O6—P—O4	105.8 (2)	N2—C10—C11	124.1 (3)
O5—P—C8	113.63 (19)	N2—C10—S	111.7 (3)
O6—P—C8	104.0 (2)	C11—C10—S	124.0 (3)
O4—P—C8	103.3 (2)	C12—C11—C16	118.6 (4)
C9—N1—C8	121.8 (3)	C12—C11—C10	121.6 (3)
C9—N1—H1A	119.1	C16—C11—C10	119.8 (3)
C8—N1—H1A	119.1	C11—C12—C13	121.7 (4)
C1—O1—C2	106.1 (5)	C11—C12—H12A	119.1
O1—C1—H1B	109.5	C13—C12—H12A	119.1
O1—C1—H1C	109.5	C14—C13—C12	118.6 (4)
H1B—C1—H1C	109.5	C14—C13—H13A	120.7
O1—C1—H1D	109.5	C12—C13—H13A	120.7
H1B—C1—H1D	109.5	C13—C14—N4	119.8 (4)
H1C—C1—H1D	109.5	C13—C14—C15	120.3 (4)
C10—N2—N3	114.8 (3)	N4—C14—C15	119.8 (4)
C3—C2—C7	116.9 (5)	C16—C15—C14	120.2 (4)
C3—C2—O1	132.5 (6)	C16—C15—H15A	119.9
C7—C2—O1	110.5 (6)	C14—C15—H15A	119.9
C9—N3—N2	113.1 (3)	C15—C16—C11	120.5 (3)
C2—C3—C4	123.1 (5)	C15—C16—H16A	119.8
C2—C3—H3B	118.5	C11—C16—H16A	119.8
C4—C3—H3B	118.5	C18—C17—H17A	109.5
O2—N4—O3	119.1 (4)	C18—C17—H17B	109.5
O2—N4—C14	121.2 (4)	H17A—C17—H17B	109.5
O3—N4—C14	119.7 (4)	C18—C17—H17C	109.5
C5—C4—C3	120.8 (5)	H17A—C17—H17C	109.5
C5—C4—H4A	119.6	H17B—C17—H17C	109.5
C3—C4—H4A	119.6	O4—C18—C17	108.2 (6)
C18—O4—P	122.8 (4)	O4—C18—H18A	110.1
C4—C5—C6	117.2 (4)	C17—C18—H18A	110.1
C4—C5—C8	124.1 (4)	O4—C18—H18B	110.1
C6—C5—C8	118.5 (4)	C17—C18—H18B	110.1
C20—O6—P	122.7 (3)	H18A—C18—H18B	108.4
C7—C6—C5	119.4 (5)	C20—C19—H19A	109.5
C7—C6—H6A	120.3	C20—C19—H19B	109.5
C5—C6—H6A	120.3	H19A—C19—H19B	109.5
C2—C7—C6	122.5 (5)	C20—C19—H19C	109.5
C2—C7—H7A	118.7	H19A—C19—H19C	109.5
C6—C7—H7A	118.7	H19B—C19—H19C	109.5
N1—C8—C5	112.2 (3)	O6—C20—C19	111.2 (5)
N1—C8—P	110.0 (3)	O6—C20—H20A	109.4
C5—C8—P	110.4 (3)	C19—C20—H20A	109.4
N1—C8—H8A	108.0	O6—C20—H20B	109.4
C5—C8—H8A	108.0	C19—C20—H20B	109.4
P—C8—H8A	108.0	H20A—C20—H20B	108.0

C1—O1—C2—C3	6.7 (9)	N2—N3—C9—N1	176.5 (4)
C1—O1—C2—C7	−176.9 (5)	N2—N3—C9—S	−0.5 (5)
C10—N2—N3—C9	1.4 (5)	C8—N1—C9—N3	0.6 (7)
C7—C2—C3—C4	2.2 (10)	C8—N1—C9—S	177.5 (3)
O1—C2—C3—C4	178.5 (6)	C10—S—C9—N3	−0.3 (3)
C2—C3—C4—C5	−0.9 (9)	C10—S—C9—N1	−177.5 (4)
O5—P—O4—C18	48.1 (5)	N3—N2—C10—C11	−177.9 (4)
O6—P—O4—C18	−78.7 (5)	N3—N2—C10—S	−1.6 (5)
C8—P—O4—C18	172.4 (5)	C9—S—C10—N2	1.0 (3)
C3—C4—C5—C6	0.3 (8)	C9—S—C10—C11	177.4 (4)
C3—C4—C5—C8	−174.3 (5)	N2—C10—C11—C12	−179.8 (4)
O5—P—O6—C20	−9.6 (5)	S—C10—C11—C12	4.3 (6)
O4—P—O6—C20	117.7 (5)	N2—C10—C11—C16	0.9 (6)
C8—P—O6—C20	−133.9 (4)	S—C10—C11—C16	−175.0 (3)
C4—C5—C6—C7	−1.1 (7)	C16—C11—C12—C13	3.5 (6)
C8—C5—C6—C7	173.8 (5)	C10—C11—C12—C13	−175.8 (4)
C3—C2—C7—C6	−3.0 (9)	C11—C12—C13—C14	−2.3 (7)
O1—C2—C7—C6	179.9 (5)	C12—C13—C14—N4	−179.2 (4)
C5—C6—C7—C2	2.5 (9)	C12—C13—C14—C15	−0.8 (7)
C9—N1—C8—C5	−136.1 (4)	O2—N4—C14—C13	178.9 (5)
C9—N1—C8—P	100.6 (4)	O3—N4—C14—C13	−3.6 (8)
C4—C5—C8—N1	−49.1 (6)	O2—N4—C14—C15	0.5 (8)
C6—C5—C8—N1	136.4 (4)	O3—N4—C14—C15	177.9 (5)
C4—C5—C8—P	74.1 (5)	C13—C14—C15—C16	2.5 (7)
C6—C5—C8—P	−100.5 (4)	N4—C14—C15—C16	−179.1 (5)
O5—P—C8—N1	53.6 (3)	C14—C15—C16—C11	−1.2 (7)
O6—P—C8—N1	178.1 (3)	C12—C11—C16—C15	−1.7 (7)
O4—P—C8—N1	−71.6 (3)	C10—C11—C16—C15	177.6 (4)
O5—P—C8—C5	−70.8 (3)	P—O4—C18—C17	−157.3 (5)
O6—P—C8—C5	53.7 (3)	P—O6—C20—C19	105.9 (5)
O4—P—C8—C5	164.0 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O5ⁱ	0.86	1.94	2.782 (6)	165

Symmetry code: (i) −x, −y, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃N₄O₆PS
M_r	478.45
Crystal system, space group	Monoclinic, P2₁/n
Temperature (K)	298
a, b, c (Å)	11.481 (2), 19.426 (4), 11.960 (2)
β (°)	117.08 (3)
V (Å³)	2375.0 (10)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.25
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	0.930, 0.976
No. of measured, independent and observed [I > 2σ(I)] reflections	4497, 4276, 2330
R_int	0.064
(sin θ/λ)_max (Å⁻¹)	0.599

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.068, 0.146, 1.03
No. of reflections	4276
No. of parameters	289
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.30, −0.21

Computer programs: CAD-4 Software (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···O5ⁱ	0.86	1.94	2.782 (6)	165

Symmetry code: (i) −x, −y, −z.

Acknowledgements

The authors are grateful to Professor Hua-Qin Wang of Nanjing University, for providing the Enraf–Nonius CAD-4 diffractometer for this research project.

References

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. Pesticide 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
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS 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

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Volume 64| Part 8| August 2008| Page o1376

doi:10.1107/S1600536808017364

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

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

Related literature

Experimental

Crystal data

Data collection

Refinement

Supporting information

Acknowledgements

References

organic compounds

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