N-[Bis(dimethyl-amino)phosphinoyl]-2,2,2-trichloro-acetamide.

In the title compound, C(6)H(13)Cl(3)N(3)O(2)P or CCl(3)C(O)NHP(O)(N(CH(3))(2)), the phosphinoyl group is synclinal to the carbonyl group and acts as an acceptor for an inter-molecular N-H⋯O hydrogen bond from the amide group as the donor.

Related literature

For the biological and pharmacological properties of carbacyl­amido­phosphate derivatives, see: Adams et al. (2002 ▶); Grimes et al. (2008 ▶). For structural and conformation studies of related mol­ecules, see: Gholivand et al. (2008a ▶,b ▶); Skopenko et al. (2004 ▶); Znovjyak et al. (2009a ▶,b ▶). For details of the synthesis, see: Kirsanov & Derkach (1956 ▶). For P—O bond lengths in compounds with amide substituents close to phospho­rus atoms, see: Rebrova et al. (1982 ▶).

Experimental

Crystal data

C6H13Cl3N3O2P

M = 296.51

Orthorhombic,

a = 15.794 (3) Å

b = 15.820 (3) Å

c = 9.739 (2) Å

V = 2433.4 (8) Å3

Z = 8

Mo Kα radiation

μ = 0.87 mm−1

T = 100 K

0.60 × 0.40 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer

Absorption correction: Gaussian (Coppens et al., 1965 ▶) T min = 0.624, T max = 0.845

35140 measured reflections

5631 independent reflections

4869 reflections with I > 2σ(I)

R int = 0.032

Refinement

R[F 2 > 2σ(F 2)] = 0.030

wR(F 2) = 0.072

S = 1.15

5631 reflections

144 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.46 e Å−3

Δρmin = −0.40 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis RED (Oxford Diffraction, 2006 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 for Windows (Farrugia, 1997 ▶); software used to prepare material for publication: WinGX (Farrugia, 1999 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810013589/jh2144sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810013589/jh2144Isup2.hkl

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

C6H13Cl3N3O2P	F(000) = 1216
Mr = 296.51	Dx = 1.619 Mg m−3
Orthorhombic, Pbca	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ac 2ab	Cell parameters from 35140 reflections
a = 15.794 (3) Å	θ = 3.6–36.1°
b = 15.820 (3) Å	µ = 0.87 mm−1
c = 9.739 (2) Å	T = 100 K
V = 2433.4 (8) Å3	Block, white
Z = 8	0.60 × 0.40 × 0.20 mm

Oxford Diffraction Xcalibur Sapphire2 (large Be window) diffractometer	5631 independent reflections
Radiation source: Enhance (Mo) X-ray Source	4869 reflections with I > 2σ(I)
graphite	Rint = 0.032
Detector resolution: 8.3359 pixels mm-1	θmax = 36.1°, θmin = 3.6°
ω scans	h = −26→26
Absorption correction: gaussian Coppens et al. (1965)	k = −25→25
Tmin = 0.624, Tmax = 0.845	l = −12→15
35140 measured reflections

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)] = 0.030	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.15	w = 1/[σ2(Fo2) + (0.0336P)2 + 0.5268P] where P = (Fo2 + 2Fc2)/3
5631 reflections	(Δ/σ)max = 0.001
144 parameters	Δρmax = 0.46 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Geometry. All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes.

	x	y	z	Uiso*/Ueq
P1	0.285320 (15)	0.522358 (14)	0.42665 (2)	0.00982 (5)
C1	0.14518 (6)	0.60952 (6)	0.48883 (9)	0.01181 (14)
C2	0.06928 (6)	0.62610 (5)	0.58869 (9)	0.01177 (15)
Cl1	0.033556 (15)	0.534225 (14)	0.67522 (3)	0.01615 (5)
Cl2	0.104133 (16)	0.701650 (14)	0.71094 (2)	0.01672 (5)
Cl3	−0.015884 (16)	0.668869 (15)	0.49346 (3)	0.01985 (6)
O1	0.26191 (5)	0.51406 (5)	0.28033 (7)	0.01480 (12)
O2	0.15469 (5)	0.65692 (5)	0.39188 (8)	0.02050 (15)
N1	0.19672 (5)	0.54418 (5)	0.52192 (8)	0.01086 (13)
N2	0.35444 (5)	0.59761 (5)	0.45503 (8)	0.01341 (14)
N3	0.32000 (5)	0.43758 (5)	0.50197 (9)	0.01413 (14)
C3	0.36307 (7)	0.63290 (7)	0.59326 (10)	0.01877 (18)
H3A	0.3449	0.5908	0.6610	0.028*
H3B	0.3277	0.6835	0.6014	0.028*
H3C	0.4224	0.6479	0.6099	0.028*
C4	0.37770 (7)	0.65551 (6)	0.34435 (11)	0.01709 (17)
H4A	0.3434	0.7070	0.3510	0.026*
H4B	0.3675	0.6282	0.2556	0.026*
H4C	0.4378	0.6702	0.3523	0.026*
C5	0.40306 (6)	0.42489 (7)	0.56243 (11)	0.01898 (18)
H5A	0.4371	0.4762	0.5507	0.028*
H5B	0.4313	0.3774	0.5169	0.028*
H5C	0.3969	0.4126	0.6605	0.028*
C6	0.26438 (7)	0.36368 (6)	0.51134 (12)	0.01950 (19)
H6A	0.2906	0.3158	0.4636	0.029*
H6B	0.2098	0.3767	0.4686	0.029*
H6C	0.2556	0.3491	0.6081	0.029*
H1N	0.1961 (10)	0.5241 (9)	0.6005 (17)	0.023 (4)*

	U11	U22	U33	U12	U13	U23
P1	0.01062 (9)	0.01090 (9)	0.00794 (9)	0.00005 (7)	0.00106 (7)	−0.00067 (7)
C1	0.0138 (4)	0.0121 (3)	0.0095 (3)	0.0019 (3)	−0.0007 (3)	−0.0001 (3)
C2	0.0123 (3)	0.0113 (3)	0.0117 (4)	0.0021 (3)	−0.0013 (3)	−0.0018 (3)
Cl1	0.01546 (10)	0.01469 (9)	0.01831 (11)	−0.00068 (7)	0.00464 (8)	0.00048 (7)
Cl2	0.02070 (10)	0.01642 (10)	0.01304 (10)	−0.00216 (7)	−0.00055 (8)	−0.00503 (7)
Cl3	0.01663 (10)	0.01936 (10)	0.02357 (12)	0.00705 (8)	−0.00704 (9)	−0.00265 (8)
O1	0.0174 (3)	0.0188 (3)	0.0082 (3)	−0.0010 (2)	0.0010 (2)	−0.0026 (2)
O2	0.0275 (4)	0.0196 (3)	0.0144 (3)	0.0069 (3)	0.0044 (3)	0.0073 (3)
N1	0.0119 (3)	0.0131 (3)	0.0076 (3)	0.0026 (2)	0.0013 (2)	0.0018 (2)
N2	0.0165 (3)	0.0145 (3)	0.0092 (3)	−0.0034 (3)	0.0001 (3)	−0.0002 (2)
N3	0.0116 (3)	0.0120 (3)	0.0188 (4)	0.0006 (2)	−0.0001 (3)	0.0027 (3)
C3	0.0226 (5)	0.0203 (4)	0.0134 (4)	−0.0056 (3)	−0.0021 (3)	−0.0032 (3)
C4	0.0195 (4)	0.0157 (4)	0.0160 (4)	−0.0041 (3)	0.0007 (3)	0.0031 (3)
C5	0.0147 (4)	0.0214 (4)	0.0208 (5)	0.0021 (3)	−0.0032 (4)	0.0047 (4)
C6	0.0177 (4)	0.0124 (4)	0.0284 (5)	−0.0003 (3)	0.0031 (4)	0.0013 (3)

P1—O1	1.4780 (8)	N3—C6	1.4652 (13)
P1—N3	1.6239 (8)	C3—H3A	0.9800
P1—N2	1.6388 (8)	C3—H3B	0.9800
P1—N1	1.7141 (8)	C3—H3C	0.9800
C1—O2	1.2151 (11)	C4—H4A	0.9800
C1—N1	1.3546 (12)	C4—H4B	0.9800
C1—C2	1.5658 (13)	C4—H4C	0.9800
C2—Cl3	1.7684 (9)	C5—H5A	0.9800
C2—Cl1	1.7723 (10)	C5—H5B	0.9800
C2—Cl2	1.7745 (9)	C5—H5C	0.9800
N1—H1N	0.828 (16)	C6—H6A	0.9800
N2—C4	1.4614 (13)	C6—H6B	0.9800
N2—C3	1.4637 (13)	C6—H6C	0.9800
N3—C5	1.4518 (13)
O1—P1—N3	116.53 (4)	N2—C3—H3A	109.5
O1—P1—N2	113.19 (4)	N2—C3—H3B	109.5
N3—P1—N2	107.40 (4)	H3A—C3—H3B	109.5
O1—P1—N1	109.61 (4)	N2—C3—H3C	109.5
N3—P1—N1	101.37 (4)	H3A—C3—H3C	109.5
N2—P1—N1	107.83 (4)	H3B—C3—H3C	109.5
O2—C1—N1	125.55 (9)	N2—C4—H4A	109.5
O2—C1—C2	118.29 (8)	N2—C4—H4B	109.5
N1—C1—C2	116.12 (8)	H4A—C4—H4B	109.5
C1—C2—Cl3	108.70 (6)	N2—C4—H4C	109.5
C1—C2—Cl1	113.68 (6)	H4A—C4—H4C	109.5
Cl3—C2—Cl1	108.72 (5)	H4B—C4—H4C	109.5
C1—C2—Cl2	106.98 (6)	N3—C5—H5A	109.5
Cl3—C2—Cl2	109.28 (5)	N3—C5—H5B	109.5
Cl1—C2—Cl2	109.40 (5)	H5A—C5—H5B	109.5
C1—N1—P1	121.03 (7)	N3—C5—H5C	109.5
C1—N1—H1N	120.3 (11)	H5A—C5—H5C	109.5
P1—N1—H1N	115.7 (11)	H5B—C5—H5C	109.5
C4—N2—C3	114.58 (8)	N3—C6—H6A	109.5
C4—N2—P1	119.89 (7)	N3—C6—H6B	109.5
C3—N2—P1	119.62 (7)	H6A—C6—H6B	109.5
C5—N3—C6	113.97 (8)	N3—C6—H6C	109.5
C5—N3—P1	127.02 (7)	H6A—C6—H6C	109.5
C6—N3—P1	119.00 (7)	H6B—C6—H6C	109.5
O2—C1—C2—Cl3	32.74 (11)	N3—P1—N2—C4	138.23 (8)
N1—C1—C2—Cl3	−149.48 (7)	N1—P1—N2—C4	−113.24 (8)
O2—C1—C2—Cl1	153.97 (8)	O1—P1—N2—C3	159.66 (7)
N1—C1—C2—Cl1	−28.25 (10)	N3—P1—N2—C3	−70.29 (8)
O2—C1—C2—Cl2	−85.16 (10)	N1—P1—N2—C3	38.24 (9)
N1—C1—C2—Cl2	92.62 (8)	O1—P1—N3—C5	118.05 (9)
O2—C1—N1—P1	1.02 (14)	N2—P1—N3—C5	−10.10 (10)
C2—C1—N1—P1	−176.58 (6)	N1—P1—N3—C5	−123.08 (9)
O1—P1—N1—C1	−53.07 (8)	O1—P1—N3—C6	−61.17 (9)
N3—P1—N1—C1	−176.80 (7)	N2—P1—N3—C6	170.68 (7)
N2—P1—N1—C1	70.54 (8)	N1—P1—N3—C6	57.70 (8)
O1—P1—N2—C4	8.18 (9)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.828 (16)	1.968 (16)	2.7586 (11)	159.3 (16)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.828 (16)	1.968 (16)	2.7586 (11)	159.3 (16)

Symmetry code: (i) .