Diethyl [2,2,2-trifluoro-1-phenyl-sulfonyl-amino-1-(trifluoro-meth-yl)eth-yl]phospho-nate.

The title compound, C(13)H(16)F(6)NO(5)PS, is of inter-est with respect to inhibition of serine hydro-lases. Its structure contains a 1.8797 (13) Å P-C bond and two inter-molecular N-H⋯O=P hydrogen bonds, resulting in centrosymmetric dimers. An intra-molecular N-H⋯O=P hydrogen bond is also present.

Related literature

For related literature, see: Chekhlov et al. (1995 ▶); Makhaeva et al. (2005 ▶); Adams et al. (2008 ▶); Chen et al. (2008 ▶); Guo et al. (2008 ▶); Kachkovskyi & Kolodiazhnyi (2007 ▶); Liu et al. (1995 ▶).

Experimental

Crystal data

C13H16F6NO5PS

M = 443.3

Monoclinic,

a = 11.6913 (15) Å

b = 10.1375 (13) Å

c = 15.5955 (19) Å

β = 93.264 (2)°

V = 1845.4 (4) Å3

Z = 4

Mo Kα radiation

μ = 0.34 mm−1

T = 113 (2) K

0.60 × 0.42 × 0.40 mm

Data collection

Bruker SMART CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Sheldrick, 2003 ▶) T min = 0.820, T max = 0.874

20001 measured reflections

4568 independent reflections

4027 reflections with I > 2σ(I)

R int = 0.022

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.082

S = 1.03

4568 reflections

246 parameters

H-atom parameters constrained

Δρmax = 0.34 e Å−3

Δρmin = −0.33 e Å−3

Data collection: SMART (Bruker, 1998 ▶); cell refinement: SAINT (Bruker, 2003 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536808020175/si2094sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536808020175/si2094Isup2.hkl

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

C13H16F6NO5PS	F000 = 904
Mr = 443.3	Dx = 1.596 Mg m−3
Monoclinic, P21/n	Mo Kα radiation λ = 0.71073 Å
Hall symbol: -P 2yn	Cell parameters from 6567 reflections
a = 11.6913 (15) Å	θ = 2.9–28.3º
b = 10.1375 (13) Å	µ = 0.35 mm−1
c = 15.5955 (19) Å	T = 113 (2) K
β = 93.264 (2)º	Plate, colourless
V = 1845.4 (4) Å3	0.60 × 0.42 × 0.40 mm
Z = 4

Bruker SMART CCD area-detector diffractometer	4568 independent reflections
Radiation source: fine-focus sealed tube	4027 reflections with I > 2σ(I)
Monochromator: graphite	Rint = 0.022
T = 113(2) K	θmax = 28.3º
φ and ω scans	θmin = 2.9º
Absorption correction: multi-scan(SADABS; Sheldrick, 2003)	h = −15→15
Tmin = 0.820, Tmax = 0.874	k = −13→13
20001 measured reflections	l = −20→20

Refinement on F2	H-atom parameters constrained
Least-squares matrix: full	w = 1/[σ2(Fo2) + (0.0427P)2 + 0.6948P] where P = (Fo2 + 2Fc2)/3
R[F2 > 2σ(F2)] = 0.029	(Δ/σ)max = 0.001
wR(F2) = 0.082	Δρmax = 0.34 e Å−3
S = 1.03	Δρmin = −0.33 e Å−3
4568 reflections	Extinction correction: none
246 parameters

Experimental. 2103 frames × 20 sec @ 4.980 cm; 0.3 ° scans in ω & φ

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
P1	0.64284 (3)	0.17485 (3)	0.04487 (2)	0.02726 (9)
S1	0.33796 (3)	0.15018 (3)	0.174771 (18)	0.02622 (8)
N1	0.46059 (9)	0.12554 (10)	0.13045 (6)	0.0247 (2)
H1A	0.4569	0.0699	0.0870	0.030*
F1	0.73735 (8)	0.14398 (10)	0.24829 (6)	0.0445 (2)
F2	0.66649 (8)	−0.02537 (9)	0.17986 (5)	0.0429 (2)
F3	0.57711 (8)	0.05961 (9)	0.28299 (5)	0.0412 (2)
F4	0.56725 (9)	0.33003 (9)	0.27115 (5)	0.0434 (2)
F5	0.67125 (8)	0.38612 (9)	0.16867 (6)	0.0415 (2)
F6	0.48768 (7)	0.39288 (8)	0.14967 (5)	0.03547 (19)
C1	0.26341 (11)	0.26504 (13)	0.10763 (7)	0.0255 (2)
C2	0.24216 (12)	0.23293 (14)	0.02114 (8)	0.0307 (3)
H2A	0.2676	0.1513	−0.0009	0.037*
C3	0.18337 (14)	0.32241 (16)	−0.03191 (9)	0.0398 (3)
H3A	0.1682	0.3022	−0.0909	0.048*
C4	0.14648 (15)	0.44131 (17)	0.00055 (9)	0.0435 (4)
H4A	0.1074	0.5028	−0.0366	0.052*
C5	0.16614 (14)	0.47135 (16)	0.08707 (9)	0.0402 (3)
H5A	0.1391	0.5522	0.1091	0.048*
C6	0.22553 (12)	0.38277 (14)	0.14136 (8)	0.0313 (3)
H6A	0.2399	0.4026	0.2005	0.038*
C7	0.57400 (11)	0.18007 (12)	0.15084 (8)	0.0258 (2)
C8	0.57452 (12)	0.32405 (14)	0.18606 (9)	0.0326 (3)
C9	0.63978 (13)	0.08914 (14)	0.21698 (9)	0.0342 (3)
C10	0.86488 (14)	0.16185 (18)	0.02046 (12)	0.0464 (4)
H10A	0.8876	0.2351	−0.0170	0.056*
H10B	0.8423	0.0853	−0.0161	0.056*
C11	0.96179 (17)	0.1256 (3)	0.08278 (18)	0.0793 (7)
H11A	0.9820	0.2017	0.1194	0.119*
H11B	1.0283	0.0995	0.0512	0.119*
H11C	0.9386	0.0519	0.1186	0.119*
C12	0.50917 (13)	0.29279 (16)	−0.07438 (9)	0.0367 (3)
H12A	0.4590	0.3713	−0.0728	0.044*
H12B	0.4613	0.2134	−0.0674	0.044*
C13	0.56368 (16)	0.28690 (17)	−0.15912 (10)	0.0455 (4)
H13A	0.6155	0.3622	−0.1640	0.068*
H13B	0.5040	0.2901	−0.2058	0.068*
H13C	0.6071	0.2046	−0.1628	0.068*
O1	0.27788 (9)	0.02744 (10)	0.16554 (6)	0.0339 (2)
O2	0.36007 (9)	0.20787 (10)	0.25771 (5)	0.0346 (2)
O3	0.61539 (8)	0.04887 (9)	0.00278 (6)	0.0311 (2)
O4	0.77052 (9)	0.20205 (12)	0.07141 (7)	0.0435 (3)
O5	0.59785 (9)	0.29985 (10)	−0.00394 (6)	0.0348 (2)

	U11	U22	U33	U12	U13	U23
P1	0.02908 (17)	0.02691 (17)	0.02539 (16)	0.00270 (12)	−0.00198 (12)	−0.00504 (12)
S1	0.03576 (17)	0.02732 (16)	0.01571 (13)	0.00577 (12)	0.00261 (11)	0.00207 (10)
N1	0.0305 (5)	0.0241 (5)	0.0192 (4)	0.0051 (4)	−0.0018 (4)	−0.0048 (4)
F1	0.0422 (5)	0.0527 (5)	0.0364 (4)	0.0091 (4)	−0.0185 (4)	−0.0058 (4)
F2	0.0575 (5)	0.0330 (4)	0.0363 (4)	0.0205 (4)	−0.0127 (4)	−0.0031 (3)
F3	0.0557 (5)	0.0430 (5)	0.0236 (4)	0.0084 (4)	−0.0093 (4)	0.0041 (3)
F4	0.0591 (6)	0.0422 (5)	0.0277 (4)	0.0078 (4)	−0.0074 (4)	−0.0163 (3)
F5	0.0415 (5)	0.0342 (5)	0.0479 (5)	−0.0042 (4)	−0.0065 (4)	−0.0146 (4)
F6	0.0423 (4)	0.0229 (4)	0.0404 (4)	0.0082 (3)	−0.0050 (3)	−0.0057 (3)
C1	0.0292 (6)	0.0292 (6)	0.0181 (5)	0.0059 (5)	0.0025 (4)	0.0009 (4)
C2	0.0388 (7)	0.0329 (7)	0.0202 (5)	0.0110 (5)	0.0005 (5)	−0.0027 (5)
C3	0.0523 (9)	0.0449 (8)	0.0215 (6)	0.0175 (7)	−0.0052 (6)	−0.0026 (5)
C4	0.0550 (9)	0.0439 (8)	0.0304 (7)	0.0243 (7)	−0.0075 (6)	0.0003 (6)
C5	0.0500 (8)	0.0379 (8)	0.0320 (7)	0.0214 (7)	−0.0022 (6)	−0.0062 (6)
C6	0.0371 (7)	0.0346 (7)	0.0222 (5)	0.0100 (5)	0.0012 (5)	−0.0042 (5)
C7	0.0319 (6)	0.0237 (6)	0.0210 (5)	0.0065 (5)	−0.0062 (4)	−0.0044 (4)
C8	0.0386 (7)	0.0287 (6)	0.0294 (6)	0.0053 (5)	−0.0067 (5)	−0.0091 (5)
C9	0.0412 (7)	0.0339 (7)	0.0261 (6)	0.0100 (6)	−0.0105 (5)	−0.0032 (5)
C10	0.0367 (8)	0.0492 (9)	0.0545 (10)	−0.0068 (7)	0.0128 (7)	−0.0050 (7)
C11	0.0352 (9)	0.110 (2)	0.0913 (17)	0.0118 (11)	−0.0041 (10)	−0.0132 (15)
C12	0.0365 (7)	0.0387 (8)	0.0345 (7)	0.0026 (6)	−0.0009 (5)	0.0107 (6)
C13	0.0660 (11)	0.0390 (8)	0.0318 (7)	0.0067 (7)	0.0048 (7)	0.0056 (6)
O1	0.0433 (5)	0.0309 (5)	0.0280 (4)	−0.0005 (4)	0.0077 (4)	0.0054 (4)
O2	0.0497 (6)	0.0391 (5)	0.0150 (4)	0.0111 (4)	0.0014 (4)	−0.0011 (4)
O3	0.0386 (5)	0.0286 (5)	0.0259 (4)	0.0044 (4)	0.0006 (4)	−0.0070 (4)
O4	0.0289 (5)	0.0543 (7)	0.0466 (6)	0.0028 (5)	−0.0028 (4)	−0.0166 (5)
O5	0.0443 (6)	0.0288 (5)	0.0308 (5)	−0.0027 (4)	−0.0012 (4)	0.0026 (4)

P1—O3	1.4632 (10)	C4—C5	1.390 (2)
P1—O4	1.5509 (11)	C4—H4A	0.9500
P1—O5	1.5545 (10)	C5—C6	1.3923 (19)
P1—C7	1.8797 (13)	C5—H5A	0.9500
S1—O2	1.4296 (9)	C6—H6A	0.9500
S1—O1	1.4321 (11)	C7—C9	1.5539 (17)
S1—N1	1.6458 (11)	C7—C8	1.5594 (17)
S1—C1	1.7629 (12)	C10—O4	1.4540 (19)
N1—C7	1.4549 (16)	C10—C11	1.496 (3)
N1—H1A	0.8800	C10—H10A	0.9900
F1—C9	1.3361 (17)	C10—H10B	0.9900
F2—C9	1.3419 (16)	C11—H11A	0.9800
F3—C9	1.3313 (18)	C11—H11B	0.9800
F4—C8	1.3359 (16)	C11—H11C	0.9800
F5—C8	1.3354 (18)	C12—O5	1.4687 (17)
F6—C8	1.3320 (16)	C12—C13	1.501 (2)
C1—C6	1.3870 (18)	C12—H12A	0.9900
C1—C2	1.3960 (16)	C12—H12B	0.9900
C2—C3	1.3838 (18)	C13—H13A	0.9800
C2—H2A	0.9500	C13—H13B	0.9800
C3—C4	1.386 (2)	C13—H13C	0.9800
C3—H3A	0.9500
O3—P1—O4	117.26 (6)	F6—C8—F5	107.48 (12)
O3—P1—O5	115.62 (6)	F6—C8—F4	108.02 (11)
O4—P1—O5	106.23 (6)	F5—C8—F4	106.43 (11)
O3—P1—C7	108.97 (6)	F6—C8—C7	110.65 (10)
O4—P1—C7	102.36 (6)	F5—C8—C7	110.84 (11)
O5—P1—C7	104.94 (6)	F4—C8—C7	113.15 (11)
O2—S1—O1	120.58 (6)	F3—C9—F1	107.88 (11)
O2—S1—N1	108.97 (6)	F3—C9—F2	106.91 (12)
O1—S1—N1	105.06 (6)	F1—C9—F2	107.63 (12)
O2—S1—C1	108.97 (6)	F3—C9—C7	111.92 (11)
O1—S1—C1	106.92 (6)	F1—C9—C7	112.07 (12)
N1—S1—C1	105.30 (5)	F2—C9—C7	110.20 (10)
C7—N1—S1	130.95 (8)	O4—C10—C11	106.50 (16)
C7—N1—H1A	114.5	O4—C10—H10A	110.4
S1—N1—H1A	114.5	C11—C10—H10A	110.4
C6—C1—C2	121.60 (11)	O4—C10—H10B	110.4
C6—C1—S1	120.05 (9)	C11—C10—H10B	110.4
C2—C1—S1	118.34 (10)	H10A—C10—H10B	108.6
C3—C2—C1	118.67 (12)	C10—C11—H11A	109.5
C3—C2—H2A	120.7	C10—C11—H11B	109.5
C1—C2—H2A	120.7	H11A—C11—H11B	109.5
C2—C3—C4	120.41 (13)	C10—C11—H11C	109.5
C2—C3—H3A	119.8	H11A—C11—H11C	109.5
C4—C3—H3A	119.8	H11B—C11—H11C	109.5
C3—C4—C5	120.51 (13)	O5—C12—C13	110.09 (13)
C3—C4—H4A	119.7	O5—C12—H12A	109.6
C5—C4—H4A	119.7	C13—C12—H12A	109.6
C4—C5—C6	119.89 (13)	O5—C12—H12B	109.6
C4—C5—H5A	120.1	C13—C12—H12B	109.6
C6—C5—H5A	120.1	H12A—C12—H12B	108.2
C1—C6—C5	118.90 (12)	C12—C13—H13A	109.5
C1—C6—H6A	120.5	C12—C13—H13B	109.5
C5—C6—H6A	120.5	H13A—C13—H13B	109.5
N1—C7—C9	109.28 (11)	C12—C13—H13C	109.5
N1—C7—C8	114.70 (10)	H13A—C13—H13C	109.5
C9—C7—C8	109.24 (10)	H13B—C13—H13C	109.5
N1—C7—P1	103.16 (8)	C10—O4—P1	123.57 (10)
C9—C7—P1	110.27 (9)	C12—O5—P1	122.10 (9)
C8—C7—P1	110.04 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1A···O3	0.88	2.34	2.8730 (14)	119
N1—H1A···O3i	0.88	2.00	2.8324 (14)	158

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1A⋯O3	0.88	2.34	2.8730 (14)	119
N1—H1A⋯O3i	0.88	2.00	2.8324 (14)	158

Symmetry code: (i) .