Dichloro-phosphinic bis-(2-chloro-eth-yl)amide.

In the title compound, C4H8Cl4NOP, the two chloro-ethyl groups are not related by crystallographic symmetry. The difference in the conformation of the two groups is shown by their N-C-C-Cl torsion angles of 64.57 (15) and 175.62 (10)°.

Related literature

The title compound is a precursor used in the synthesis of the anti­tumor drug cyclo­phosphamide and its analogues. For information on organo­phospho­rus heterocyclic compounds, see: Surendra Babu et al. (2009 ▶); Srinivasulu et al. (2008 ▶); Krishna et al. (2006 ▶). For the crystal structures of cyclo­phosphamide analogues, see: Camerman & Camerman (1973 ▶); Jones et al. (1996 ▶); Himes et al. (1982 ▶); Camerman et al. (1983 ▶); Perales & García-Blanco (1977a ▶,b ▶); Gałdecki & Głowka (1981 ▶); Boyd et al. (1980 ▶); Shih et al. (1986 ▶). For the pharma­cological activity of cyclo­phosphamide analogues, see: Lin et al. (1980 ▶); Borch & Canute (1991 ▶).

Experimental

Crystal data

C4H8Cl4NOP

M = 258.88

Monoclinic,

a = 9.0723 (15) Å

b = 8.4810 (14) Å

c = 13.135 (2) Å

β = 101.221 (2)°

V = 991.4 (3) Å3

Z = 4

Mo Kα radiation

μ = 1.30 mm−1

T = 298 K

0.16 × 0.12 × 0.10 mm

Data collection

Bruker APEXII CCD diffractometer

Absorption correction: multi-scan (SADABS; Bruker, 2009 ▶) T min = 0.819, T max = 0.881

9480 measured reflections

3255 independent reflections

2725 reflections with I > 2σ(I)

R int = 0.020

Refinement

R[F 2 > 2σ(F 2)] = 0.029

wR(F 2) = 0.090

S = 1.05

3255 reflections

101 parameters

H-atom parameters constrained

Δρmax = 0.57 e Å−3

Δρmin = −0.46 e Å−3

Data collection: APEX2 (Bruker, 2009 ▶); cell refinement: SAINT (Bruker, 2009 ▶); data reduction: SAINT; 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 and local procedures.

Click here for additional data file.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S1600536812049586/fy2076sup1.cif

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049586/fy2076Isup2.cdx

Click here for additional data file.

Structure factors: contains datablock(s) I. DOI: 10.1107/S1600536812049586/fy2076Isup3.hkl

Click here for additional data file.

Supplementary material file. DOI: 10.1107/S1600536812049586/fy2076Isup4.cml

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

C4H8Cl4NOP	F(000) = 520
Mr = 258.88	Dx = 1.735 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
a = 9.0723 (15) Å	Cell parameters from 4728 reflections
b = 8.4810 (14) Å	θ = 2.3–31.1°
c = 13.135 (2) Å	µ = 1.30 mm−1
β = 101.221 (2)°	T = 298 K
V = 991.4 (3) Å3	Block, colourless
Z = 4	0.16 × 0.12 × 0.10 mm

Bruker APEXII CCD diffractometer	3255 independent reflections
Radiation source: fine-focus sealed tube	2725 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.020
φ and ω scans	θmax = 32.2°, θmin = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2009)	h = −13→13
Tmin = 0.819, Tmax = 0.881	k = −12→12
9480 measured reflections	l = −19→13

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.029	H-atom parameters constrained
wR(F2) = 0.090	w = 1/[σ2(Fo2) + (0.0482P)2 + 0.1876P] where P = (Fo2 + 2Fc2)/3
S = 1.05	(Δ/σ)max = 0.002
3255 reflections	Δρmax = 0.57 e Å−3
101 parameters	Δρmin = −0.46 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0064 (13)

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
C1	0.38633 (16)	0.82538 (16)	0.87493 (12)	0.0381 (3)
H1A	0.4301	0.7845	0.8186	0.046*
H1B	0.4682	0.8544	0.9310	0.046*
C2	0.2970 (2)	0.97152 (18)	0.83776 (13)	0.0467 (3)
H2A	0.2125	0.9432	0.7834	0.056*
H2B	0.3599	1.0447	0.8087	0.056*
C3	0.19521 (15)	0.60676 (16)	0.83359 (10)	0.0353 (3)
H3A	0.1429	0.6769	0.7802	0.042*
H3B	0.1208	0.5556	0.8662	0.042*
C4	0.27918 (18)	0.48303 (19)	0.78420 (13)	0.0448 (3)
H4A	0.3374	0.4169	0.8376	0.054*
H4B	0.3479	0.5337	0.7463	0.054*
Cl1	0.31341 (5)	0.44237 (4)	1.05878 (3)	0.05244 (12)
Cl3	0.22968 (5)	1.06456 (5)	0.94101 (4)	0.05789 (13)
Cl2	0.08981 (4)	0.71564 (5)	1.05773 (3)	0.05103 (12)
Cl4	0.14781 (6)	0.36563 (5)	0.69800 (4)	0.06145 (14)
N1	0.29789 (12)	0.69934 (13)	0.91169 (9)	0.0328 (2)
O1	0.41231 (13)	0.76345 (14)	1.10623 (8)	0.0474 (3)
P1	0.29887 (4)	0.67627 (4)	1.03420 (3)	0.03356 (10)

	U11	U22	U33	U12	U13	U23
C1	0.0403 (6)	0.0353 (6)	0.0409 (7)	−0.0035 (5)	0.0131 (5)	−0.0024 (5)
C2	0.0600 (9)	0.0347 (6)	0.0451 (8)	−0.0025 (6)	0.0094 (7)	0.0020 (6)
C3	0.0376 (6)	0.0343 (6)	0.0330 (6)	0.0004 (5)	0.0042 (5)	−0.0035 (5)
C4	0.0481 (8)	0.0409 (7)	0.0444 (8)	−0.0001 (6)	0.0067 (6)	−0.0131 (6)
Cl1	0.0676 (3)	0.03754 (19)	0.0523 (2)	0.00726 (15)	0.01214 (19)	0.01047 (15)
Cl3	0.0608 (3)	0.0414 (2)	0.0733 (3)	0.00801 (16)	0.0174 (2)	−0.01022 (18)
Cl2	0.04327 (19)	0.0641 (3)	0.0497 (2)	0.00731 (16)	0.01884 (16)	−0.00236 (17)
Cl4	0.0777 (3)	0.0514 (2)	0.0521 (3)	−0.0121 (2)	0.0049 (2)	−0.01980 (19)
N1	0.0376 (5)	0.0315 (5)	0.0292 (5)	−0.0022 (4)	0.0062 (4)	−0.0026 (4)
O1	0.0479 (6)	0.0540 (6)	0.0369 (5)	−0.0032 (5)	−0.0006 (4)	−0.0072 (5)
P1	0.03567 (17)	0.03484 (17)	0.02971 (16)	0.00247 (12)	0.00520 (12)	−0.00150 (12)

C1—N1	1.4732 (18)	C3—H3A	0.9700
C1—C2	1.509 (2)	C3—H3B	0.9700
C1—H1A	0.9700	C4—Cl4	1.7800 (16)
C1—H1B	0.9700	C4—H4A	0.9700
C2—Cl3	1.7767 (17)	C4—H4B	0.9700
C2—H2A	0.9700	Cl1—P1	2.0100 (6)
C2—H2B	0.9700	Cl2—P1	2.0081 (6)
C3—N1	1.4713 (16)	N1—P1	1.6195 (12)
C3—C4	1.515 (2)	O1—P1	1.4567 (11)
N1—C1—C2	114.16 (12)	H3A—C3—H3B	108.0
N1—C1—H1A	108.7	C3—C4—Cl4	109.25 (11)
C2—C1—H1A	108.7	C3—C4—H4A	109.8
N1—C1—H1B	108.7	Cl4—C4—H4A	109.8
C2—C1—H1B	108.7	C3—C4—H4B	109.8
H1A—C1—H1B	107.6	Cl4—C4—H4B	109.8
C1—C2—Cl3	111.13 (11)	H4A—C4—H4B	108.3
C1—C2—H2A	109.4	C3—N1—C1	118.04 (11)
Cl3—C2—H2A	109.4	C3—N1—P1	120.57 (9)
C1—C2—H2B	109.4	C1—N1—P1	121.02 (9)
Cl3—C2—H2B	109.4	O1—P1—N1	116.78 (7)
H2A—C2—H2B	108.0	O1—P1—Cl2	112.63 (5)
N1—C3—C4	111.43 (11)	N1—P1—Cl2	108.07 (5)
N1—C3—H3A	109.3	O1—P1—Cl1	112.37 (5)
C4—C3—H3A	109.3	N1—P1—Cl1	105.45 (4)
N1—C3—H3B	109.3	Cl2—P1—Cl1	100.01 (2)
C4—C3—H3B	109.3
N1—C1—C2—Cl3	64.57 (15)	C3—N1—P1—O1	175.23 (10)
N1—C3—C4—Cl4	175.62 (10)	C1—N1—P1—O1	−11.87 (13)
C4—C3—N1—C1	78.71 (15)	C3—N1—P1—Cl2	−56.60 (10)
C4—C3—N1—P1	−108.18 (13)	C1—N1—P1—Cl2	116.30 (10)
C2—C1—N1—C3	75.10 (16)	C3—N1—P1—Cl1	49.65 (10)
C2—C1—N1—P1	−97.97 (14)	C1—N1—P1—Cl1	−137.45 (10)