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

Wan, R.; Han, F.; Zhang, J.; Yin, L.; Wang, J.

doi:10.1107/S1600536807046521

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

R. Wan, F. Han, J. Zhang, L. Yin and J. Wang

In the molecule of the title compound, C₂₀H₂₃FN₃O₄PS, two methyl groups are disordered over two positions each, with site occupancy factors in the approximate ratio 2:1. The thiadiazole and benzene rings are planar; the thiadiazole ring is oriented with respect to the adjacent benzene ring at a dihedral angle of 7.54 (3)°, while the dihedral angle between the two benzene rings is 81.28 (3)°. In the crystal structure, intermolecular N—H

O hydrogen bonds link the molecules, and a weak intramolecular C—H

S hydrogen bond is also present.

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Supporting information

	Crystallographic Information File (CIF) https://doi.org/10.1107/S1600536807046521/hk2321sup1.cif Contains datablocks global, I
	Structure factor file (CIF format) https://doi.org/10.1107/S1600536807046521/hk2321Isup2.hkl Contains datablock I

CCDC reference: 663834

checkCIF report

Key indicators

Single-crystal X-ray study
T = 298 K
Mean (C-C) = 0.005 Å
Disorder in main residue
R factor = 0.050
wR factor = 0.157
Data-to-parameter ratio = 14.8

checkCIF/PLATON results

No syntax errors found



Alert level C
PLAT066_ALERT_1_C Predicted and Reported Transmissions Identical .          ?
PLAT154_ALERT_1_C The su's on the Cell Angles are Equal  (x 10000)       3000 Deg.
PLAT220_ALERT_2_C Large Non-Solvent    C     Ueq(max)/Ueq(min) ...       2.90 Ratio
PLAT301_ALERT_3_C Main Residue  Disorder .........................       6.00 Perc.
PLAT322_ALERT_2_C Check Hybridisation of  S      in Main Residue .          ?
PLAT340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ...          5
PLAT720_ALERT_4_C Number of Unusual/Non-Standard Label(s) ........          6

Alert level G
PLAT793_ALERT_1_G Check the Absolute Configuration of C5     = ...          R
PLAT860_ALERT_3_G Note: Number of Least-Squares Restraints .......          4

   0 ALERT level A = In general: serious problem
   0 ALERT level B = Potentially serious problem
   7 ALERT level C = Check and explain
   2 ALERT level G = General alerts; check

   3 ALERT type 1 CIF construction/syntax error, inconsistent or missing data
   2 ALERT type 2 Indicator that the structure model may be wrong or deficient
   3 ALERT type 3 Indicator that the structure quality may be low
   1 ALERT type 4 Improvement, methodology, query or suggestion
   0 ALERT type 5 Informative message, check

Comment top

1,3,4-Thiadiazole derivatives represent an interesting class of compounds possessing broad spectrum biological activities (Nakagawa et al., 1996; Wang et al., 1999). These compounds are known to exhibit diverse biological effects, such as insecticidal and fungicidal activities (Wang et al., 1999). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the bond lengths and angles are within normal ranges (Allen et al., 1987). Rings A (C6—C11), B (S/N2/N3/C12/C13) and C (C14—C18) are, of course, planar and they are oriented at dihedral angles of A/B = 82.53 (3)°, A/C = 81.28 (3)° and B/C = 7.54 (3)°.

In the crystal structure, intermolecular N—H···O hydrogen bonds (Table 1) link the molecules (Fig. 2); a weak intramolecular C—H···S hydrogen bond (Table 1) is also present, in which they seem to be effective in the stabilization of the structure.

Related literature top

For related literature, see: Nakagawa et al. (1996); Wang et al. (1999). For bond- length data, see: Allen et al. (1987).

Experimental top

For the preparation of the title compound, (I), N-(4-fluorobenzylidene)-5 -(4-methoxyphenyl)-1,3,4-thiadiazol-2-amine (620 mg, 2 mmol) and diethyl phosphite (690 mg, 5 mmol) were added in a flask (25 ml) and reacted in an oil bath (363 K) for 6 h. After cooling and filtering, the title compound, (I), was obtained (m.p. 465 K). Crystals of (I) suitable for X-ray analysis were obtained by slow evaporation of an acetone solution.

Structure description top

For related literature, see: Nakagawa et al. (1996); Wang et al. (1999). For bond- length data, see: Allen et al. (1987).

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, 1997); program(s) used to refine structure: SHELXL97 (Sheldrick, 1997); molecular graphics: SHELXTL (Siemens, 1996); software used to prepare material for publication: SHELXTL (Siemens, 1996).

Figures top

	Fig. 1. The molecular structure of the title molecule, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 50% probability level. Hydrogen bond is shown as dashed line.
	Fig. 2. A packing diagram for (I). Hydrogen bonds are shown as dashed lines.

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

Crystal data top

C₂₀H₂₃FN₃O₄PS	Z = 2
M_r = 451.44	F(000) = 472
Triclinic, P1	D_x = 1.346 Mg m⁻³
Hall symbol: -P 1	Melting point: 465 K
a = 9.4140 (19) Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.227 (2) Å	Cell parameters from 25 reflections
c = 12.923 (3) Å	θ = 10–13°
α = 110.44 (3)°	µ = 0.26 mm⁻¹
β = 98.80 (3)°	T = 298 K
γ = 100.58 (3)°	Block, colorless
V = 1113.7 (5) Å³	0.30 × 0.20 × 0.20 mm

Data collection top

Enraf–Nonius CAD-4 diffractometer	3276 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	R_int = 0.019
Graphite monochromator	θ_max = 26.0°, θ_min = 1.7°
ω/2θ scans	h = −11→11
Absorption correction: ψ scan (North et al., 1968)	k = −12→11
T_min = 0.927, T_max = 0.951	l = 0→15
4656 measured reflections	3 standard reflections every 120 min
4374 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)] = 0.050	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.157	H-atom parameters constrained
S = 0.82	w = 1/[σ²(F_o²) + (0.088P)² + 2.5493P] where P = (F_o² + 2F_c²)/3
4374 reflections	(Δ/σ)_max < 0.001
295 parameters	Δρ_max = 0.36 e Å⁻³
4 restraints	Δρ_min = −0.32 e Å⁻³

Crystal data top

C₂₀H₂₃FN₃O₄PS	γ = 100.58 (3)°
M_r = 451.44	V = 1113.7 (5) Å³
Triclinic, P1	Z = 2
a = 9.4140 (19) Å	Mo Kα radiation
b = 10.227 (2) Å	µ = 0.26 mm⁻¹
c = 12.923 (3) Å	T = 298 K
α = 110.44 (3)°	0.30 × 0.20 × 0.20 mm
β = 98.80 (3)°

Data collection top

Enraf–Nonius CAD-4 diffractometer	3276 reflections with I > 2σ(I)
Absorption correction: ψ scan (North et al., 1968)	R_int = 0.019
T_min = 0.927, T_max = 0.951	3 standard reflections every 120 min
4656 measured reflections	intensity decay: none
4374 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.050	4 restraints
wR(F²) = 0.157	H-atom parameters constrained
S = 0.82	Δρ_max = 0.36 e Å⁻³
4374 reflections	Δρ_min = −0.32 e Å⁻³
295 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	Occ. (<1)
P	0.43635 (9)	0.67087 (8)	−0.10499 (7)	0.0491 (2)
S	0.87296 (9)	0.75456 (8)	0.24611 (7)	0.0517 (2)
F	0.9354 (3)	0.4665 (3)	−0.3671 (2)	0.1057 (9)
N1	0.6691 (3)	0.7228 (3)	0.0607 (2)	0.0522 (6)
H1	0.6079	0.6613	0.0747	0.063*
N2	0.8756 (3)	0.9250 (3)	0.1405 (2)	0.0606 (7)
N3	0.9991 (3)	0.9880 (3)	0.2313 (2)	0.0616 (7)
O1	0.3723 (3)	0.7941 (3)	−0.0351 (2)	0.0662 (6)
O2	0.4072 (3)	0.6740 (2)	−0.22638 (19)	0.0637 (6)
O3	0.3799 (2)	0.5289 (2)	−0.1037 (2)	0.0634 (6)
O4	1.4759 (3)	1.0977 (3)	0.6845 (2)	0.0969 (10)
C1	0.1394 (13)	0.7103 (15)	0.0092 (13)	0.100 (4)	0.66 (2)
H1A	0.1483	0.6129	−0.0121	0.150*	0.66 (2)
H1B	0.0362	0.7101	−0.0028	0.150*	0.66 (2)
H1C	0.1875	0.7645	0.0880	0.150*	0.66 (2)
C1'	0.146 (4)	0.794 (6)	0.024 (3)	0.102 (17)	0.34 (2)
H1A'	0.1728	0.7332	0.0620	0.153*	0.34 (2)
H1B'	0.0400	0.7665	−0.0049	0.153*	0.34 (2)
H1C'	0.1771	0.8926	0.0761	0.153*	0.34 (2)
C2	0.2111 (4)	0.7775 (5)	−0.0612 (4)	0.0870 (13)
H2A	0.1692	0.7176	−0.1410	0.104*
H2B	0.1914	0.8713	−0.0466	0.104*
C3	0.287 (3)	0.5362 (15)	−0.4207 (9)	0.121 (8)	0.66 (2)
H3A	0.1913	0.5461	−0.4063	0.160*	0.66 (2)
H3B	0.2747	0.4448	−0.4812	0.160*	0.66 (2)
H3C	0.3300	0.6126	−0.4421	0.160*	0.66 (2)
C3'	0.3900 (4)	0.5599 (19)	−0.4201 (13)	0.100 (8)	0.34 (2)
H3A'	0.3191	0.4835	−0.4836	0.150*	0.34 (2)
H3B'	0.4887	0.5582	−0.4299	0.150*	0.34 (2)
H3C'	0.3724	0.6510	−0.4156	0.150*	0.34 (2)
C4	0.3732 (8)	0.5430 (6)	−0.3294 (4)	0.098 (2)
H4A	0.4667	0.5280	−0.3475	0.118*
H4B	0.3287	0.4625	−0.3116	0.118*
C5	0.6343 (3)	0.7417 (3)	−0.0464 (3)	0.0478 (7)
H5A	0.6603	0.8452	−0.0307	0.057*
C6	0.7176 (3)	0.6676 (3)	−0.1318 (3)	0.0508 (7)
C7	0.7093 (4)	0.5201 (4)	−0.1631 (3)	0.0686 (10)
H7A	0.6543	0.4677	−0.1300	0.082*
C8	0.7820 (5)	0.4521 (4)	−0.2427 (4)	0.0788 (11)
H8A	0.7770	0.3543	−0.2638	0.095*
C9	0.8619 (4)	0.5325 (4)	−0.2896 (3)	0.0707 (10)
C10	0.8720 (4)	0.6766 (4)	−0.2615 (3)	0.0625 (9)
H10A	0.9266	0.7281	−0.2954	0.075*
C11	0.7994 (3)	0.7430 (3)	−0.1818 (3)	0.0530 (8)
H11A	0.8057	0.8410	−0.1613	0.064*
C12	0.7997 (3)	0.8036 (3)	0.1388 (3)	0.0476 (7)
C13	1.0132 (3)	0.9141 (3)	0.2943 (3)	0.0495 (7)
C14	1.1326 (3)	0.9586 (3)	0.3959 (3)	0.0520 (7)
C15	1.2501 (4)	1.0796 (4)	0.4250 (3)	0.0669 (9)
H15A	1.2531	1.1326	0.3794	0.080*
C16	1.3619 (4)	1.1212 (4)	0.5212 (3)	0.0740 (11)
H16A	1.4403	1.2015	0.5391	0.089*
C17	1.3596 (4)	1.0462 (4)	0.5914 (3)	0.0668 (10)
C18	1.2444 (4)	0.9278 (4)	0.5645 (3)	0.0672 (9)
H18A	1.2419	0.8754	0.6105	0.081*
C19	1.1308 (4)	0.8862 (4)	0.4678 (3)	0.0598 (8)
H19A	1.0515	0.8072	0.4513	0.072*
C20	1.4839 (6)	1.0152 (6)	0.7528 (4)	0.1139 (18)
H20A	1.5718	1.0605	0.8136	0.171*
H20B	1.4877	0.9196	0.7071	0.171*
H20C	1.3977	1.0099	0.7839	0.171*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
P	0.0473 (4)	0.0461 (4)	0.0491 (4)	0.0022 (3)	0.0015 (3)	0.0215 (4)
S	0.0508 (4)	0.0441 (4)	0.0535 (4)	−0.0007 (3)	0.0014 (3)	0.0218 (3)
F	0.123 (2)	0.0909 (18)	0.122 (2)	0.0464 (16)	0.0713 (18)	0.0367 (16)
N1	0.0445 (14)	0.0525 (15)	0.0548 (15)	−0.0055 (11)	0.0002 (11)	0.0289 (12)
N2	0.0568 (16)	0.0501 (15)	0.0670 (18)	−0.0068 (12)	−0.0027 (13)	0.0308 (14)
N3	0.0562 (16)	0.0511 (15)	0.0636 (17)	−0.0086 (12)	−0.0024 (13)	0.0239 (14)
O1	0.0536 (13)	0.0646 (15)	0.0669 (15)	0.0127 (11)	0.0055 (11)	0.0145 (12)
O2	0.0720 (15)	0.0640 (14)	0.0497 (13)	0.0073 (12)	0.0020 (11)	0.0256 (11)
O3	0.0551 (13)	0.0545 (13)	0.0754 (16)	−0.0040 (10)	−0.0006 (11)	0.0347 (12)
O4	0.091 (2)	0.091 (2)	0.0657 (17)	0.0096 (16)	−0.0207 (15)	0.0022 (15)
C1	0.055 (5)	0.146 (10)	0.117 (8)	0.029 (5)	0.035 (5)	0.064 (8)
C1'	0.081 (19)	0.142 (5)	0.073 (13)	0.014 (3)	0.035 (12)	0.034 (2)
C2	0.060 (2)	0.101 (3)	0.104 (4)	0.031 (2)	0.007 (2)	0.044 (3)
C3	0.156 (18)	0.125 (11)	0.084 (6)	0.076 (12)	−0.050 (8)	−0.003 (6)
C3'	0.131 (18)	0.108 (12)	0.047 (8)	0.014 (11)	0.016 (9)	0.025 (7)
C4	0.148 (7)	0.085 (4)	0.054 (3)	−0.011 (4)	0.004 (4)	0.015 (3)
C5	0.0490 (16)	0.0401 (15)	0.0526 (17)	0.0018 (12)	0.0042 (13)	0.0241 (13)
C6	0.0454 (16)	0.0452 (16)	0.0588 (19)	0.0020 (13)	0.0072 (14)	0.0237 (14)
C7	0.072 (2)	0.056 (2)	0.093 (3)	0.0159 (17)	0.030 (2)	0.043 (2)
C8	0.089 (3)	0.053 (2)	0.104 (3)	0.023 (2)	0.035 (2)	0.034 (2)
C9	0.073 (2)	0.068 (2)	0.073 (2)	0.0220 (19)	0.025 (2)	0.025 (2)
C10	0.060 (2)	0.062 (2)	0.066 (2)	0.0053 (16)	0.0163 (17)	0.0299 (18)
C11	0.0545 (18)	0.0470 (17)	0.0529 (18)	0.0030 (14)	0.0046 (14)	0.0222 (14)
C12	0.0454 (16)	0.0430 (16)	0.0502 (17)	0.0039 (12)	0.0086 (13)	0.0182 (13)
C13	0.0479 (17)	0.0423 (16)	0.0495 (17)	0.0039 (13)	0.0095 (13)	0.0123 (13)
C14	0.0497 (17)	0.0442 (16)	0.0496 (17)	0.0072 (13)	0.0085 (14)	0.0072 (14)
C15	0.057 (2)	0.060 (2)	0.067 (2)	−0.0039 (16)	0.0013 (17)	0.0204 (17)
C16	0.061 (2)	0.060 (2)	0.073 (2)	−0.0026 (17)	−0.0052 (18)	0.0110 (19)
C17	0.068 (2)	0.062 (2)	0.0485 (19)	0.0188 (18)	−0.0030 (16)	0.0008 (16)
C18	0.074 (2)	0.065 (2)	0.055 (2)	0.0168 (18)	0.0063 (17)	0.0177 (17)
C19	0.060 (2)	0.0509 (18)	0.058 (2)	0.0088 (15)	0.0048 (16)	0.0160 (16)
C20	0.128 (4)	0.126 (4)	0.063 (3)	0.043 (3)	−0.020 (3)	0.020 (3)

Geometric parameters (Å, º) top

C1—C2	1.487 (13)	C9—F	1.359 (4)
C1—H1A	0.9600	C9—C10	1.369 (5)
C1—H1B	0.9600	C10—C11	1.373 (5)
C1—H1C	0.9600	C10—H10A	0.9300
C1'—C2	1.31 (3)	C11—H11A	0.9300
C1'—H1A'	0.9600	C12—N2	1.305 (4)
C1'—H1B'	0.9600	C12—N1	1.371 (4)
C1'—H1C'	0.9600	C12—S	1.723 (3)
C2—O1	1.468 (4)	C13—N3	1.299 (4)
C2—H2A	0.9700	C13—C14	1.462 (4)
C2—H2B	0.9700	C13—S	1.743 (3)
C3—C4	1.299 (10)	C14—C19	1.376 (5)
C3—H3A	0.9600	C14—C15	1.393 (4)
C3—H3B	0.9600	C15—C16	1.378 (5)
C3—H3C	0.9600	C15—H15A	0.9300
C3'—C4	1.269 (14)	C16—C17	1.377 (5)
C3'—H3A'	0.9600	C16—H16A	0.9300
C3'—H3B'	0.9600	C17—O4	1.366 (4)
C3'—H3C'	0.9600	C17—C18	1.368 (5)
C4—O2	1.462 (5)	C18—C19	1.392 (5)
C4—H4A	0.9700	C18—H18A	0.9300
C4—H4B	0.9700	C19—H19A	0.9300
C5—N1	1.460 (4)	C20—O4	1.421 (6)
C5—C6	1.518 (4)	C20—H20A	0.9600
C5—P	1.806 (3)	C20—H20B	0.9600
C5—H5A	0.9800	C20—H20C	0.9600
C6—C11	1.375 (4)	N1—H1	0.8600
C6—C7	1.402 (4)	N2—N3	1.387 (4)
C7—C8	1.378 (5)	O1—P	1.555 (3)
C7—H7A	0.9300	O2—P	1.563 (2)
C8—C9	1.368 (5)	O3—P	1.459 (2)
C8—H8A	0.9300

C2—C1—H1A	109.5	C10—C9—C8	122.9 (4)
C2—C1—H1B	109.5	C9—C10—C11	118.3 (3)
C2—C1—H1C	109.5	C9—C10—H10A	120.9
C2—C1'—H1A'	109.5	C11—C10—H10A	120.9
C2—C1'—H1B'	109.5	C10—C11—C6	121.3 (3)
H1A'—C1'—H1B'	109.5	C10—C11—H11A	119.4
C2—C1'—H1C'	109.5	C6—C11—H11A	119.4
H1A'—C1'—H1C'	109.5	N2—C12—N1	123.2 (3)
H1B'—C1'—H1C'	109.5	N2—C12—S	114.8 (2)
C1'—C2—O1	116.8 (13)	N1—C12—S	122.0 (2)
O1—C2—C1	110.7 (6)	N3—C13—C14	124.2 (3)
C1'—C2—H2A	128.0	N3—C13—S	113.0 (2)
O1—C2—H2A	109.5	C14—C13—S	122.8 (2)
C1—C2—H2A	109.5	C19—C14—C15	117.7 (3)
C1'—C2—H2B	78.1	C19—C14—C13	121.5 (3)
O1—C2—H2B	109.5	C15—C14—C13	120.7 (3)
C1—C2—H2B	109.5	C16—C15—C14	120.3 (4)
H2A—C2—H2B	108.1	C16—C15—H15A	119.9
C4—C3—H3A	109.5	C14—C15—H15A	119.9
C4—C3—H3B	109.5	C15—C16—C17	121.3 (3)
C4—C3—H3C	109.5	C15—C16—H16A	119.4
C4—C3'—H3A'	109.5	C17—C16—H16A	119.4
C4—C3'—H3B'	111.0	O4—C17—C18	124.7 (4)
H3A'—C3'—H3B'	109.5	O4—C17—C16	116.1 (4)
C4—C3'—H3C'	109.5	C18—C17—C16	119.2 (3)
H3A'—C3'—H3C'	109.5	C17—C18—C19	119.7 (4)
H3B'—C3'—H3C'	109.5	C17—C18—H18A	120.2
C3'—C4—O2	116.7 (10)	C19—C18—H18A	120.2
C3—C4—O2	118.7 (7)	C14—C19—C18	121.8 (3)
C3'—C4—H4A	67.0	C14—C19—H19A	119.1
C3—C4—H4A	107.6	C18—C19—H19A	119.1
O2—C4—H4A	107.6	O4—C20—H20A	109.5
C3'—C4—H4B	135.0	O4—C20—H20B	109.5
C3—C4—H4B	107.6	H20A—C20—H20B	109.5
O2—C4—H4B	107.6	O4—C20—H20C	109.5
H4A—C4—H4B	107.1	H20A—C20—H20C	109.5
N1—C5—C6	113.1 (2)	H20B—C20—H20C	109.5
N1—C5—P	107.85 (19)	C12—N1—C5	119.7 (2)
C6—C5—P	109.9 (2)	C12—N1—H1	120.1
N1—C5—H5A	108.6	C5—N1—H1	120.1
C6—C5—H5A	108.6	C12—N2—N3	111.4 (3)
P—C5—H5A	108.6	C13—N3—N2	113.8 (2)
C11—C6—C7	118.8 (3)	C2—O1—P	119.1 (3)
C11—C6—C5	120.6 (3)	C4—O2—P	122.2 (3)
C7—C6—C5	120.6 (3)	C17—O4—C20	117.4 (4)
C8—C7—C6	120.5 (3)	O3—P—O1	116.31 (15)
C8—C7—H7A	119.7	O3—P—O2	113.80 (14)
C6—C7—H7A	119.7	O1—P—O2	103.59 (14)
C9—C8—C7	118.1 (3)	O3—P—C5	112.94 (14)
C9—C8—H8A	120.9	O1—P—C5	102.91 (14)
C7—C8—H8A	120.9	O2—P—C5	106.07 (14)
F—C9—C10	118.7 (3)	C12—S—C13	87.04 (15)
F—C9—C8	118.4 (4)

N1—C5—C6—C11	−127.1 (3)	C6—C5—N1—C12	77.7 (3)
P—C5—C6—C11	112.3 (3)	P—C5—N1—C12	−160.5 (2)
N1—C5—C6—C7	54.6 (4)	N1—C12—N2—N3	177.1 (3)
P—C5—C6—C7	−66.0 (3)	S—C12—N2—N3	−0.7 (4)
C11—C6—C7—C8	0.0 (5)	C14—C13—N3—N2	−179.0 (3)
C5—C6—C7—C8	178.4 (3)	S—C13—N3—N2	0.6 (4)
C6—C7—C8—C9	0.0 (6)	C12—N2—N3—C13	0.1 (4)
C7—C8—C9—F	179.2 (4)	C1'—C2—O1—P	126 (3)
C7—C8—C9—C10	−0.3 (7)	C1—C2—O1—P	91.2 (8)
F—C9—C10—C11	−179.0 (3)	C3'—C4—O2—P	−162.0 (5)
C8—C9—C10—C11	0.5 (6)	C3—C4—O2—P	148.3 (14)
C9—C10—C11—C6	−0.5 (5)	C18—C17—O4—C20	5.6 (6)
C7—C6—C11—C10	0.2 (5)	C16—C17—O4—C20	−174.4 (4)
C5—C6—C11—C10	−178.2 (3)	C2—O1—P—O3	−57.8 (3)
N3—C13—C14—C19	171.1 (3)	C2—O1—P—O2	67.8 (3)
S—C13—C14—C19	−8.4 (4)	C2—O1—P—C5	178.2 (3)
N3—C13—C14—C15	−6.7 (5)	C4—O2—P—O3	−19.2 (4)
S—C13—C14—C15	173.7 (3)	C4—O2—P—O1	−146.4 (4)
C19—C14—C15—C16	1.8 (5)	C4—O2—P—C5	105.6 (4)
C13—C14—C15—C16	179.7 (3)	N1—C5—P—O3	−47.2 (3)
C14—C15—C16—C17	−0.8 (6)	C6—C5—P—O3	76.5 (2)
C15—C16—C17—O4	−179.7 (4)	N1—C5—P—O1	79.0 (2)
C15—C16—C17—C18	0.3 (6)	C6—C5—P—O1	−157.3 (2)
O4—C17—C18—C19	179.3 (3)	N1—C5—P—O2	−172.5 (2)
C16—C17—C18—C19	−0.7 (6)	C6—C5—P—O2	−48.8 (2)
C15—C14—C19—C18	−2.3 (5)	N2—C12—S—C13	0.9 (3)
C13—C14—C19—C18	179.8 (3)	N1—C12—S—C13	−177.0 (3)
C17—C18—C19—C14	1.8 (5)	N3—C13—S—C12	−0.8 (3)
N2—C12—N1—C5	21.0 (5)	C14—C13—S—C12	178.8 (3)
S—C12—N1—C5	−161.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.13	2.795 (5)	133
C19—H19A···S	0.93	2.73	3.142 (4)	108

Symmetry code: (i) −x+1, −y+1, −z.

Experimental details

Crystal data
Chemical formula	C₂₀H₂₃FN₃O₄PS
M_r	451.44
Crystal system, space group	Triclinic, P1
Temperature (K)	298
a, b, c (Å)	9.4140 (19), 10.227 (2), 12.923 (3)
α, β, γ (°)	110.44 (3), 98.80 (3), 100.58 (3)
V (Å³)	1113.7 (5)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.26
Crystal size (mm)	0.30 × 0.20 × 0.20

Data collection
Diffractometer	Enraf–Nonius CAD-4
Absorption correction	ψ scan (North et al., 1968)
T_min, T_max	0.927, 0.951
No. of measured, independent and observed [I > 2σ(I)] reflections	4656, 4374, 3276
R_int	0.019
(sin θ/λ)_max (Å⁻¹)	0.616

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.050, 0.157, 0.82
No. of reflections	4374
No. of parameters	295
No. of restraints	4
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.36, −0.32

Computer programs: CAD-4 Software (Enraf–Nonius, 1989), XCAD4 (Harms & Wocadlo, 1995), SHELXS97 (Sheldrick, 1997), SHELXL97 (Sheldrick, 1997), SHELXTL (Siemens, 1996).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O3ⁱ	0.86	2.13	2.795 (5)	133
C19—H19A···S	0.93	2.73	3.142 (4)	108

Symmetry code: (i) −x+1, −y+1, −z.

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