N-(2-Chloro-2,2-difluoro-acet-yl)-N',N''-diisopropyl-phospho-ric triamide.

In the title compound, C(8)H(17)ClF(2)N(3)O(2)P, the phosphoryl group and the NH unit of the C(O)NHP(O) moiety adopt a syn conformation with respect to each other. The P atom is in a tetra-hedral coordination environment and the environment of the N atom of the C(O)NHP(O) moiety is essentially planar. In the crystal, adjacent mol-ecules are linked via N-H⋯O =P and N-H⋯O =C hydrogen bonds, building R(2) (2)(8) and R(2) (2)(12) rings in a linear arrangement parallel to [110].

Related literature

For metal complexes of phosphoryl donor ligands, see: Gholivand et al. (2010 ▶). For a phospho­ric triamide compound having a C(=O)NHP(=O) skeleton, see: Pourayoubi et al. (2010 ▶). For hydrogen-bond motifs, see: Etter et al. (1990 ▶); Bernstein et al. (1995 ▶). For the synthesis of the starting material, CClF2C(O)NHP(O)Cl2, see: Iriarte et al. (2008 ▶).

Experimental

Crystal data

n class="Chemical">C8H17ClF2N3O2P

M = 291.67

Triclinic,

a = 8.1993 (7) Å

b = 9.6735 (9) Å

c = 9.8331 (9) Å

α = 99.784 (2)°

β = 105.999 (2)°

γ = 110.770 (2)°

V = 669.18 (10) Å3

Z = 2

Mo Kα radiation

μ = 0.42 mm−1

T = 100 K

0.26 × 0.19 × 0.16 mm

Data collection

Bruker SMART APEXII CCD area-detector diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2005 ▶) T min = 0.602, T max = 0.750

9089 measured reflections

4218 independent reflections

3337 reflections with I > 2σ(I)

R int = 0.024

Refinement

R[F 2 > 2σ(F 2)] = 0.036

wR(F 2) = 0.095

S = 1.04

4218 reflections

158 parameters

H-atom parameters constrained

Δρmax = 0.56 e Å−3

Δρmin = −0.30 e Å−3

Data collection: n class="Gene">APEX2 (Bruker, 2005 ▶); cell refinpan>emenpan>t: SAINT (Bruker, 2005 ▶); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refinpan>e structure: SHELXTL (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008 ▶).

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536811005435/dn2655sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811005435/dn2655Isup2.hkl

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

C8H17ClF2N3O2P	Z = 2
Mr = 291.67	F(000) = 304
Triclinic, P1	Dx = 1.448 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 8.1993 (7) Å	Cell parameters from 2867 reflections
b = 9.6735 (9) Å	θ = 2.3–30.9°
c = 9.8331 (9) Å	µ = 0.42 mm−1
α = 99.784 (2)°	T = 100 K
β = 105.999 (2)°	Prizm, colorless
γ = 110.770 (2)°	0.26 × 0.19 × 0.16 mm
V = 669.18 (10) Å3

Bruker SMART APEXII CCD area-detector diffractometer	4218 independent reflections
Radiation source: fine-focus sealed tube	3337 reflections with I > 2σ(I)
graphite	Rint = 0.024
φ and ω scans	θmax = 31.0°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2005)	h = −11→11
Tmin = 0.602, Tmax = 0.750	k = −14→14
9089 measured reflections	l = −14→14

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)] = 0.036	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.095	H-atom parameters constrained
S = 1.04	w = 1/[σ2(Fo2) + (0.0527P)2 + 0.0127P] where P = (Fo2 + 2Fc2)/3
4218 reflections	(Δ/σ)max < 0.001
158 parameters	Δρmax = 0.56 e Å−3
0 restraints	Δρmin = −0.30 e Å−3

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds 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	0.23257 (4)	0.86972 (4)	0.03714 (4)	0.01390 (8)
Cl1	0.30477 (6)	0.56630 (4)	−0.36890 (4)	0.03081 (10)
F1	0.54717 (11)	0.63181 (10)	−0.11562 (10)	0.0284 (2)
F2	0.31465 (14)	0.40675 (9)	−0.19141 (11)	0.0322 (2)
O1	0.10801 (14)	0.52987 (10)	−0.10574 (11)	0.0238 (2)
O2	0.37834 (13)	1.03015 (10)	0.10823 (10)	0.0196 (2)
N1	0.33089 (14)	0.77459 (12)	−0.05183 (12)	0.0146 (2)
H1	0.4368	0.8292	−0.0609	0.018*
N2	0.03816 (15)	0.83557 (13)	−0.09290 (12)	0.0182 (2)
H2	−0.0483	0.8420	−0.0661	0.022*
N3	0.16459 (15)	0.79008 (12)	0.15566 (12)	0.0155 (2)
H3	0.0753	0.6993	0.1225	0.019*
C1	0.25344 (17)	0.61960 (14)	−0.10878 (14)	0.0153 (2)
C2	0.36184 (19)	0.55503 (15)	−0.18656 (15)	0.0192 (3)
C3	0.02381 (19)	0.84469 (16)	−0.24394 (15)	0.0201 (3)
H3A	0.0704	0.7721	−0.2874	0.024*
C4	−0.1816 (2)	0.78961 (18)	−0.33779 (16)	0.0259 (3)
H4A	−0.2525	0.6837	−0.3386	0.039*
H4B	−0.1939	0.7916	−0.4394	0.039*
H4C	−0.2309	0.8581	−0.2959	0.039*
C5	0.1427 (2)	1.00657 (18)	−0.24315 (16)	0.0262 (3)
H5A	0.2750	1.0341	−0.1889	0.039*
H5B	0.1051	1.0809	−0.1947	0.039*
H5C	0.1246	1.0090	−0.3453	0.039*
C6	0.29579 (18)	0.82087 (16)	0.30596 (15)	0.0208 (3)
H6A	0.3976	0.9277	0.3361	0.025*
C7	0.1941 (2)	0.81568 (18)	0.41385 (16)	0.0268 (3)
H7A	0.1366	0.8888	0.4081	0.040*
H7B	0.2834	0.8442	0.5148	0.040*
H7C	0.0965	0.7108	0.3884	0.040*
C8	0.3848 (3)	0.7080 (2)	0.3090 (2)	0.0390 (4)
H8A	0.4568	0.7195	0.2437	0.058*
H8B	0.2867	0.6020	0.2749	0.058*
H8C	0.4685	0.7294	0.4105	0.058*

	U11	U22	U33	U12	U13	U23
P1	0.01625 (15)	0.00992 (14)	0.01683 (16)	0.00349 (11)	0.01039 (12)	0.00433 (11)
Cl1	0.0425 (2)	0.0345 (2)	0.02119 (18)	0.01780 (18)	0.01803 (16)	0.00824 (15)
F1	0.0208 (4)	0.0305 (5)	0.0358 (5)	0.0133 (4)	0.0117 (4)	0.0065 (4)
F2	0.0469 (6)	0.0162 (4)	0.0489 (6)	0.0186 (4)	0.0300 (5)	0.0147 (4)
O1	0.0247 (5)	0.0128 (4)	0.0318 (5)	0.0005 (4)	0.0187 (4)	0.0040 (4)
O2	0.0237 (5)	0.0115 (4)	0.0233 (5)	0.0026 (4)	0.0158 (4)	0.0030 (4)
N1	0.0148 (5)	0.0108 (5)	0.0195 (5)	0.0034 (4)	0.0109 (4)	0.0043 (4)
N2	0.0203 (5)	0.0223 (5)	0.0191 (5)	0.0112 (5)	0.0126 (4)	0.0091 (4)
N3	0.0153 (5)	0.0125 (5)	0.0161 (5)	0.0012 (4)	0.0081 (4)	0.0042 (4)
C1	0.0178 (6)	0.0119 (5)	0.0171 (6)	0.0054 (5)	0.0089 (5)	0.0047 (4)
C2	0.0243 (7)	0.0134 (6)	0.0246 (7)	0.0089 (5)	0.0131 (5)	0.0076 (5)
C3	0.0255 (7)	0.0244 (7)	0.0177 (6)	0.0151 (6)	0.0118 (5)	0.0076 (5)
C4	0.0262 (7)	0.0281 (7)	0.0222 (7)	0.0131 (6)	0.0066 (6)	0.0045 (6)
C5	0.0276 (7)	0.0329 (8)	0.0226 (7)	0.0121 (6)	0.0129 (6)	0.0148 (6)
C6	0.0176 (6)	0.0220 (6)	0.0180 (6)	0.0032 (5)	0.0057 (5)	0.0069 (5)
C7	0.0352 (8)	0.0334 (8)	0.0180 (6)	0.0181 (7)	0.0124 (6)	0.0099 (6)
C8	0.0395 (9)	0.0669 (12)	0.0355 (9)	0.0384 (9)	0.0212 (8)	0.0278 (9)

P1—O2	1.4768 (9)	C3—H3A	1.0000
P1—N3	1.6190 (11)	C4—H4A	0.9800
P1—N2	1.6262 (12)	C4—H4B	0.9800
P1—N1	1.7039 (11)	C4—H4C	0.9800
Cl1—C2	1.7566 (14)	C5—H5A	0.9800
F1—C2	1.3366 (16)	C5—H5B	0.9800
F2—C2	1.3351 (15)	C5—H5C	0.9800
O1—C1	1.2127 (15)	C6—C8	1.513 (2)
N1—C1	1.3447 (15)	C6—C7	1.5164 (19)
N1—H1	0.8800	C6—H6A	1.0000
N2—C3	1.4775 (17)	C7—H7A	0.9800
N2—H2	0.8390	C7—H7B	0.9800
N3—C6	1.4754 (17)	C7—H7C	0.9800
N3—H3	0.8536	C8—H8A	0.9800
C1—C2	1.5399 (17)	C8—H8B	0.9800
C3—C5	1.520 (2)	C8—H8C	0.9800
C3—C4	1.5207 (19)
O2—P1—N3	112.27 (5)	C3—C4—H4A	109.5
O2—P1—N2	119.69 (6)	C3—C4—H4B	109.5
N3—P1—N2	103.94 (6)	H4A—C4—H4B	109.5
O2—P1—N1	105.13 (5)	C3—C4—H4C	109.5
N3—P1—N1	112.31 (5)	H4A—C4—H4C	109.5
N2—P1—N1	103.30 (6)	H4B—C4—H4C	109.5
C1—N1—P1	122.76 (9)	C3—C5—H5A	109.5
C1—N1—H1	118.6	C3—C5—H5B	109.5
P1—N1—H1	118.6	H5A—C5—H5B	109.5
C3—N2—P1	123.77 (9)	C3—C5—H5C	109.5
C3—N2—H2	116.2	H5A—C5—H5C	109.5
P1—N2—H2	117.0	H5B—C5—H5C	109.5
C6—N3—P1	121.89 (8)	N3—C6—C8	111.29 (12)
C6—N3—H3	112.7	N3—C6—C7	109.51 (11)
P1—N3—H3	117.9	C8—C6—C7	111.49 (12)
O1—C1—N1	126.01 (12)	N3—C6—H6A	108.1
O1—C1—C2	118.79 (11)	C8—C6—H6A	108.1
N1—C1—C2	115.19 (10)	C7—C6—H6A	108.1
F2—C2—F1	107.66 (11)	C6—C7—H7A	109.5
F2—C2—C1	109.72 (10)	C6—C7—H7B	109.5
F1—C2—C1	112.14 (11)	H7A—C7—H7B	109.5
F2—C2—Cl1	108.56 (10)	C6—C7—H7C	109.5
F1—C2—Cl1	108.94 (9)	H7A—C7—H7C	109.5
C1—C2—Cl1	109.74 (9)	H7B—C7—H7C	109.5
N2—C3—C5	111.99 (11)	C6—C8—H8A	109.5
N2—C3—C4	108.48 (11)	C6—C8—H8B	109.5
C5—C3—C4	112.00 (12)	H8A—C8—H8B	109.5
N2—C3—H3A	108.1	C6—C8—H8C	109.5
C5—C3—H3A	108.1	H8A—C8—H8C	109.5
C4—C3—H3A	108.1	H8B—C8—H8C	109.5
O2—P1—N1—C1	168.43 (10)	O1—C1—C2—F2	−22.92 (17)
N3—P1—N1—C1	46.05 (12)	N1—C1—C2—F2	158.19 (11)
N2—P1—N1—C1	−65.33 (11)	O1—C1—C2—F1	−142.50 (13)
O2—P1—N2—C3	72.29 (12)	N1—C1—C2—F1	38.60 (15)
N3—P1—N2—C3	−161.47 (10)	O1—C1—C2—Cl1	96.28 (13)
N1—P1—N2—C3	−44.04 (11)	N1—C1—C2—Cl1	−82.62 (12)
O2—P1—N3—C6	−36.29 (12)	P1—N2—C3—C5	−61.53 (14)
N2—P1—N3—C6	−167.07 (10)	P1—N2—C3—C4	174.35 (9)
N1—P1—N3—C6	81.94 (11)	P1—N3—C6—C8	−89.23 (13)
P1—N1—C1—O1	0.56 (19)	P1—N3—C6—C7	147.05 (10)
P1—N1—C1—C2	179.37 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2i	0.88	1.87	2.7295 (13)	164
N3—H3···O1ii	0.85	2.14	2.9645 (14)	163

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2i	0.88	1.87	2.7295 (13)	164
N3—H3⋯O1ii	0.85	2.14	2.9645 (14)	163

Symmetry codes: (i) ; (ii) .