Dimethyl [(4-fluoro-phen-yl)(6-methoxy-benzothia-zol-2-ylamino)meth-yl]phospho-nate.

In the mol-ecule of title compound, C(17)H(18)FN(2)O(4)PS, both the benzene ring with its conjunction C atom and the benzothia-zole ring with its conjunction N atom are close to planar (the maximum deviations are 0.0267 and 0.0427 Å for the benzene and benzothiazole rings, respectively), the dihedral angle between the planes of the benzothia-zole and benzene rings is 119.05 (3)°. The mol-ecular packing is stabilized by inter-molecular N-H⋯O, C-H⋯N and C-H⋯F hydrogen bonding, and by C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 2.99 (2), 2.96 (3), 2.88 (2) and 3.773 (4) Å].

Related literature

For the biological activity of α-amino­phospho­nate derivatives, see: Kafarski & Lejczak (2001 ▶); De Lombaert et al. (1995 ▶); Du et al., (1999 ▶). For activities of α-amino­phospho­nate derivatives containing an F atom and benzothia­zole or iaoxazole units, see: Yang et al. (2005 ▶); Song et al. (2005 ▶); Jin et al. (2006 ▶). For related structures, see: Fang et al. (2009 ▶); Yang et al. (2005 ▶); Jin et al. (2006 ▶); Song et al. (2005 ▶); Alvarez et al. (2005 ▶); Chen & Li (1987 ▶); Li et al. (2008 ▶).

Experimental

Crystal data

C17H18FN2O4PS

M = 396.36

Monoclinic,

a = 19.761 (5) Å

b = 15.781 (4) Å

c = 14.395 (4) Å

β = 122.109 (3)°

V = 3802.4 (16) Å3

Z = 8

Mo Kα radiation

μ = 0.29 mm−1

T = 296 K

0.30 × 0.26 × 0.22 mm

Data collection

Bruker APEXII area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 1996 ▶) T min = 0.919, T max = 0.939

9669 measured reflections

3428 independent reflections

2477 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.041

wR(F 2) = 0.115

S = 1.04

3428 reflections

238 parameters

H-atom parameters constrained

Δρmax = 0.22 e Å−3

Δρmin = −0.26 e Å−3

Data collection: APEX2 (Bruker, 2004 ▶); cell refinement: SAINT (Bruker, 2004 ▶); data reduction: SAIn class="Chemical">NT; 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: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809015384/at2769sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809015384/at2769Isup2.hkl

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

C17H18FN2O4PS	F(000) = 1648
Mr = 396.36	Dx = 1.385 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 5837 reflections
a = 19.761 (5) Å	θ = 2.8–27.9°
b = 15.781 (4) Å	µ = 0.29 mm−1
c = 14.395 (4) Å	T = 296 K
β = 122.109 (3)°	Block, colourless
V = 3802.4 (16) Å3	0.30 × 0.26 × 0.22 mm
Z = 8

Bruker APEXII area-detector diffractometer	3428 independent reflections
Radiation source: fine-focus sealed tube	2477 reflections with I > 2σ(I)
graphite	Rint = 0.039
φ and ω scans	θmax = 25.2°, θmin = 1.9°
Absorption correction: multi-scan (SADABS; Sheldrick, 1996)	h = −23→23
Tmin = 0.919, Tmax = 0.939	k = −18→18
9669 measured reflections	l = −15→17

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)] = 0.041	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.115	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0545P)2 + 1.1262P] where P = (Fo2 + 2Fc2)/3
3428 reflections	(Δ/σ)max < 0.001
238 parameters	Δρmax = 0.22 e Å−3
0 restraints	Δρmin = −0.26 e Å−3

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.

	x	y	z	Uiso*/Ueq
S1	0.07360 (4)	0.28313 (4)	0.06124 (5)	0.0510 (2)
P1	0.20273 (4)	0.09893 (4)	−0.09266 (5)	0.0483 (2)
N2	0.06939 (11)	0.11776 (12)	0.06276 (16)	0.0477 (5)
C5	0.10708 (13)	0.18124 (14)	0.05470 (17)	0.0421 (5)
C4	0.00865 (13)	0.14714 (14)	0.07713 (18)	0.0445 (5)
C6	0.00177 (13)	0.23554 (14)	0.07921 (17)	0.0438 (5)
C7	−0.05321 (14)	0.27298 (16)	0.09682 (19)	0.0524 (6)
H7	−0.0568	0.3317	0.0981	0.063*
C1	−0.10315 (14)	0.22182 (16)	0.11256 (19)	0.0506 (6)
C3	−0.04236 (14)	0.09767 (16)	0.0913 (2)	0.0571 (7)
H3	−0.0395	0.0390	0.0890	0.069*
C2	−0.09822 (15)	0.13484 (16)	0.1089 (2)	0.0563 (6)
H2	−0.1326	0.1009	0.1184	0.068*
N1	0.16956 (11)	0.17525 (12)	0.04083 (17)	0.0524 (5)
H1	0.1923	0.2209	0.0382	0.063*
C8	0.19929 (13)	0.09419 (14)	0.03023 (19)	0.0452 (6)
H8	0.1605	0.0505	0.0196	0.054*
C9	0.27995 (14)	0.06879 (14)	0.12740 (18)	0.0452 (6)
C11	0.37489 (18)	−0.04111 (18)	0.2316 (2)	0.0659 (8)
H11	0.3884	−0.0982	0.2439	0.079*
C10	0.30051 (17)	−0.01584 (16)	0.1484 (2)	0.0560 (6)
H10	0.2630	−0.0567	0.1049	0.067*
C14	0.33614 (15)	0.12855 (17)	0.1936 (2)	0.0625 (7)
H14	0.3237	0.1859	0.1810	0.075*
C12	0.42812 (17)	0.0196 (2)	0.2955 (2)	0.0684 (8)
C13	0.41102 (17)	0.1034 (2)	0.2788 (3)	0.0751 (9)
H13	0.4489	0.1435	0.3238	0.090*
F1	0.50137 (11)	−0.00510 (13)	0.37934 (15)	0.1064 (7)
O1	−0.15552 (10)	0.26361 (12)	0.13111 (15)	0.0658 (5)
C17	−0.20925 (16)	0.21423 (19)	0.1466 (2)	0.0707 (8)
H17A	−0.2437	0.1822	0.0813	0.106*
H17B	−0.2409	0.2511	0.1617	0.106*
H17C	−0.1794	0.1762	0.2071	0.106*
O2	0.24876 (11)	0.17048 (11)	−0.09456 (13)	0.0612 (5)
O4	0.23331 (10)	0.01050 (10)	−0.10441 (13)	0.0555 (4)
O3	0.11234 (11)	0.09795 (13)	−0.18384 (15)	0.0752 (6)
C16	0.31296 (19)	−0.0033 (2)	−0.0807 (3)	0.0886 (10)
H16A	0.3292	0.0444	−0.1056	0.133*
H16B	0.3138	−0.0536	−0.1177	0.133*
H16C	0.3490	−0.0101	−0.0031	0.133*
C15	0.0861 (2)	0.1088 (3)	−0.2974 (3)	0.1293 (16)
H15A	0.1166	0.1532	−0.3040	0.194*
H15B	0.0305	0.1236	−0.3386	0.194*
H15C	0.0938	0.0569	−0.3254	0.194*

	U11	U22	U33	U12	U13	U23
S1	0.0591 (4)	0.0372 (4)	0.0646 (4)	−0.0040 (3)	0.0382 (3)	0.0005 (3)
P1	0.0512 (4)	0.0440 (4)	0.0452 (3)	−0.0112 (3)	0.0226 (3)	−0.0035 (3)
N2	0.0461 (11)	0.0395 (11)	0.0582 (12)	−0.0059 (9)	0.0282 (10)	−0.0038 (9)
C5	0.0426 (13)	0.0393 (13)	0.0389 (12)	−0.0061 (10)	0.0180 (11)	−0.0032 (9)
C4	0.0451 (13)	0.0396 (14)	0.0455 (13)	−0.0073 (10)	0.0219 (11)	−0.0049 (10)
C6	0.0455 (13)	0.0416 (14)	0.0425 (12)	−0.0052 (11)	0.0221 (11)	−0.0035 (10)
C7	0.0572 (15)	0.0428 (14)	0.0582 (15)	−0.0044 (12)	0.0313 (13)	−0.0054 (11)
C1	0.0490 (14)	0.0532 (16)	0.0514 (14)	−0.0053 (12)	0.0278 (12)	−0.0090 (11)
C3	0.0579 (16)	0.0412 (15)	0.0777 (18)	−0.0081 (12)	0.0398 (15)	−0.0053 (12)
C2	0.0549 (15)	0.0535 (17)	0.0678 (16)	−0.0135 (12)	0.0374 (14)	−0.0064 (12)
N1	0.0529 (12)	0.0390 (11)	0.0741 (14)	−0.0097 (9)	0.0396 (11)	−0.0039 (10)
C8	0.0488 (14)	0.0367 (13)	0.0547 (14)	−0.0089 (11)	0.0306 (12)	−0.0056 (10)
C9	0.0538 (14)	0.0431 (14)	0.0464 (13)	−0.0045 (11)	0.0319 (12)	−0.0008 (10)
C11	0.087 (2)	0.0563 (18)	0.0570 (16)	0.0167 (16)	0.0403 (17)	0.0113 (14)
C10	0.0756 (18)	0.0459 (16)	0.0494 (14)	−0.0029 (13)	0.0352 (14)	−0.0002 (11)
C14	0.0611 (17)	0.0487 (16)	0.0647 (17)	−0.0037 (13)	0.0247 (15)	−0.0009 (13)
C12	0.0643 (18)	0.079 (2)	0.0573 (16)	0.0179 (16)	0.0290 (15)	0.0111 (15)
C13	0.0598 (18)	0.070 (2)	0.0721 (19)	−0.0062 (15)	0.0192 (16)	−0.0051 (15)
F1	0.0756 (12)	0.1209 (17)	0.0865 (13)	0.0313 (11)	0.0186 (10)	0.0189 (11)
O1	0.0625 (11)	0.0652 (12)	0.0842 (13)	−0.0062 (9)	0.0488 (11)	−0.0148 (10)
C17	0.0617 (18)	0.087 (2)	0.0781 (19)	−0.0073 (15)	0.0467 (16)	−0.0076 (15)
O2	0.0787 (12)	0.0477 (10)	0.0626 (11)	−0.0209 (9)	0.0412 (10)	−0.0049 (8)
O4	0.0680 (11)	0.0442 (10)	0.0622 (10)	−0.0108 (8)	0.0399 (9)	−0.0105 (8)
O3	0.0579 (11)	0.0853 (14)	0.0560 (11)	−0.0091 (10)	0.0125 (10)	0.0023 (10)
C16	0.093 (2)	0.086 (2)	0.125 (3)	0.0037 (19)	0.084 (2)	0.003 (2)
C15	0.120 (3)	0.149 (4)	0.054 (2)	−0.030 (3)	0.003 (2)	0.009 (2)

S1—C6	1.742 (2)	C9—C14	1.381 (3)
S1—C5	1.760 (2)	C9—C10	1.382 (3)
P1—O2	1.4593 (17)	C11—C12	1.357 (4)
P1—O3	1.5560 (19)	C11—C10	1.372 (4)
P1—O4	1.5653 (18)	C11—H11	0.9300
P1—C8	1.807 (2)	C10—H10	0.9300
N2—C5	1.290 (3)	C14—C13	1.386 (4)
N2—C4	1.401 (3)	C14—H14	0.9300
C5—N1	1.355 (3)	C12—C13	1.355 (4)
C4—C3	1.373 (3)	C12—F1	1.359 (3)
C4—C6	1.404 (3)	C13—H13	0.9300
C6—C7	1.374 (3)	O1—C17	1.427 (3)
C7—C1	1.384 (3)	C17—H17A	0.9600
C7—H7	0.9300	C17—H17B	0.9600
C1—O1	1.368 (3)	C17—H17C	0.9600
C1—C2	1.379 (3)	O4—C16	1.439 (3)
C3—C2	1.388 (3)	O3—C15	1.438 (4)
C3—H3	0.9300	C16—H16A	0.9600
C2—H2	0.9300	C16—H16B	0.9600
N1—C8	1.449 (3)	C16—H16C	0.9600
N1—H1	0.8600	C15—H15A	0.9600
C8—C9	1.513 (3)	C15—H15B	0.9600
C8—H8	0.9800	C15—H15C	0.9600
C6—S1—C5	88.47 (10)	C14—C9—C8	121.5 (2)
O2—P1—O3	116.07 (11)	C10—C9—C8	120.1 (2)
O2—P1—O4	114.04 (10)	C12—C11—C10	118.1 (3)
O3—P1—O4	103.65 (10)	C12—C11—H11	120.9
O2—P1—C8	113.48 (10)	C10—C11—H11	120.9
O3—P1—C8	101.64 (11)	C11—C10—C9	121.7 (3)
O4—P1—C8	106.64 (10)	C11—C10—H10	119.1
C5—N2—C4	109.72 (19)	C9—C10—H10	119.1
N2—C5—N1	125.0 (2)	C9—C14—C13	120.3 (3)
N2—C5—S1	116.95 (17)	C9—C14—H14	119.9
N1—C5—S1	118.01 (17)	C13—C14—H14	119.9
C3—C4—N2	126.0 (2)	C13—C12—C11	122.6 (3)
C3—C4—C6	118.4 (2)	C13—C12—F1	119.0 (3)
N2—C4—C6	115.62 (19)	C11—C12—F1	118.4 (3)
C7—C6—C4	121.8 (2)	C12—C13—C14	119.0 (3)
C7—C6—S1	128.96 (18)	C12—C13—H13	120.5
C4—C6—S1	109.24 (16)	C14—C13—H13	120.5
C6—C7—C1	118.8 (2)	C1—O1—C17	118.1 (2)
C6—C7—H7	120.6	O1—C17—H17A	109.5
C1—C7—H7	120.6	O1—C17—H17B	109.5
O1—C1—C2	124.3 (2)	H17A—C17—H17B	109.5
O1—C1—C7	115.5 (2)	O1—C17—H17C	109.5
C2—C1—C7	120.2 (2)	H17A—C17—H17C	109.5
C4—C3—C2	120.3 (2)	H17B—C17—H17C	109.5
C4—C3—H3	119.8	C16—O4—P1	123.11 (18)
C2—C3—H3	119.8	C15—O3—P1	121.1 (2)
C1—C2—C3	120.5 (2)	O4—C16—H16A	109.5
C1—C2—H2	119.8	O4—C16—H16B	109.5
C3—C2—H2	119.8	H16A—C16—H16B	109.5
C5—N1—C8	121.96 (19)	O4—C16—H16C	109.5
C5—N1—H1	119.0	H16A—C16—H16C	109.5
C8—N1—H1	119.0	H16B—C16—H16C	109.5
N1—C8—C9	115.05 (18)	O3—C15—H15A	109.5
N1—C8—P1	107.14 (15)	O3—C15—H15B	109.5
C9—C8—P1	110.28 (15)	H15A—C15—H15B	109.5
N1—C8—H8	108.0	O3—C15—H15C	109.5
C9—C8—H8	108.0	H15A—C15—H15C	109.5
P1—C8—H8	108.0	H15B—C15—H15C	109.5
C14—C9—C10	118.3 (2)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.86	1.99	2.793 (3)	156
C8—H8···N2	0.98	2.44	2.868 (4)	106
C14—H14···N1	0.93	2.62	2.919 (5)	100
C16—H16C···F1ii	0.96	2.51	3.2496	133
C15—H15B···Cg1iii	0.96	2.99	3.608 (4)	123
C16—H16B···Cg3iv	0.96	2.96	3.549 (4)	121
C17—H17C···Cg1v	0.96	2.88	3.625 (3)	136

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.86	1.99	2.793 (3)	156
C16—H16C⋯F1ii	0.96	2.51	3.2496	133
C15—H15B⋯Cg1iii	0.96	2.99	3.608 (4)	123
C16—H16B⋯Cg3iv	0.96	2.96	3.549 (4)	121
C17—H17C⋯Cg1v	0.96	2.88	3.625 (3)	136

Symmetry codes: (i) ; (ii) ; (iii) ; (iv) ; (v) . Cg1 and Cg3 are the centroids of the S1/N2/C4–C6 and C9–C14 rings, respectively.