N,N'-Bis(2-chloro-benz-yl)-N''-(dichloro-acet-yl)phospho-ric triamide.

In the title compound, C(16)H(16)Cl(4)N(3)O(2)P, the phosphoryl and carbonyl groups are anti to each other. The dihedral angle between the benzene rings is 33.59 (16)°. In the crystal, adjacent mol-ecules are linked via N-H⋯O=P and N-H⋯O=C hydrogen bonds, into an extended chain running parallel to the a axis.

Related literature

For biologically active organo­phospho­rus compounds, see: Ekstrom et al. (2006 ▶). For the anti­cancer activity of compounds with a C(O)NHP(O) skeleton, see: Gholivand et al. (2011 ▶). For related structures, see: Sabbaghi et al. (2010 ▶).

Experimental

Crystal data

C16H16Cl4N3O2P

M = 455.09

Triclinic,

a = 9.901 (1) Å

b = 10.179 (1) Å

c = 12.013 (2) Å

α = 90.403 (5)°

β = 112.851 (6)°

γ = 114.084 (6)°

V = 998.7 (2) Å3

Z = 2

Mo Kα radiation

μ = 0.69 mm−1

T = 295 K

0.22 × 0.12 × 0.11 mm

Data collection

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer

Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009 ▶) T min = 0.978, T max = 1.000

6193 measured reflections

3510 independent reflections

2786 reflections with I > 2σ(I)

R int = 0.018

Refinement

R[F 2 > 2σ(F 2)] = 0.061

wR(F 2) = 0.156

S = 1.02

3510 reflections

235 parameters

H-atom parameters constrained

Δρmax = 0.96 e Å−3

Δρmin = −0.65 e Å−3

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SIR92 (Altomare et al., 1993 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97 and PLATON (Spek, 2009 ▶).

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811000845/fi2102sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536811000845/fi2102Isup2.hkl

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

C16H16Cl4N3O2P	Z = 2
Mr = 455.09	F(000) = 464
Triclinic, P1	Dx = 1.513 Mg m−3
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.901 (1) Å	Cell parameters from 2802 reflections
b = 10.179 (1) Å	θ = 3.5–29.0°
c = 12.013 (2) Å	µ = 0.69 mm−1
α = 90.403 (5)°	T = 295 K
β = 112.851 (6)°	Prism, colourless
γ = 114.084 (6)°	0.22 × 0.12 × 0.11 mm
V = 998.7 (2) Å3

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3510 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2786 reflections with I > 2σ(I)
graphite	Rint = 0.018
Detector resolution: 16.3280 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→12
Tmin = 0.978, Tmax = 1.000	l = −14→13
6193 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.156	H-atom parameters constrained
S = 1.02	w = 1/[σ2(Fo2) + (0.0618P)2 + 1.5174P] where P = (Fo2 + 2Fc2)/3
3510 reflections	(Δ/σ)max < 0.001
235 parameters	Δρmax = 0.96 e Å−3
0 restraints	Δρmin = −0.65 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
P	0.84901 (11)	0.52095 (11)	0.59850 (8)	0.0398 (3)
Cl1	0.4017 (2)	0.3402 (3)	0.12756 (12)	0.1300 (8)
Cl2	0.5672 (2)	0.16627 (16)	0.23126 (18)	0.1108 (6)
Cl3	0.65788 (18)	0.91760 (16)	0.50769 (15)	0.0893 (5)
Cl4	0.77087 (18)	0.44836 (16)	1.03178 (11)	0.0804 (4)
O1	1.0238 (3)	0.5568 (3)	0.6484 (2)	0.0543 (7)
O2	0.5072 (3)	0.4115 (4)	0.3908 (3)	0.0670 (9)
N1	0.7379 (4)	0.4006 (4)	0.6531 (3)	0.0496 (8)
H1	0.6627	0.3184	0.6048	0.059*
N2	0.7656 (3)	0.4413 (3)	0.4495 (3)	0.0427 (7)
H2	0.8279	0.4239	0.4240	0.051*
N3	0.8251 (4)	0.6669 (3)	0.6149 (3)	0.0481 (8)
H3	0.7538	0.6631	0.6405	0.058*
C1	0.5775 (5)	0.3419 (5)	0.2368 (4)	0.0512 (10)
H1A	0.6696	0.4058	0.2197	0.061*
C2	0.6105 (4)	0.4020 (4)	0.3661 (3)	0.0423 (8)
C3	0.9204 (5)	0.8049 (5)	0.5877 (4)	0.0611 (11)
H3A	1.0292	0.8142	0.6081	0.073*
H3B	0.9319	0.8859	0.6395	0.073*
C4	0.8437 (5)	0.8158 (4)	0.4545 (4)	0.0524 (10)
C5	0.7214 (5)	0.8603 (4)	0.4084 (4)	0.0560 (10)
C6	0.6453 (6)	0.8610 (5)	0.2847 (5)	0.0741 (14)
H6	0.5635	0.8919	0.2570	0.089*
C7	0.6907 (8)	0.8161 (6)	0.2034 (5)	0.0846 (16)
H7	0.6393	0.8155	0.1199	0.102*
C8	0.8110 (8)	0.7727 (6)	0.2449 (5)	0.0837 (16)
H8	0.8424	0.7428	0.1897	0.100*
C9	0.8878 (6)	0.7724 (5)	0.3692 (5)	0.0678 (12)
H9	0.9705	0.7425	0.3960	0.081*
C10	0.7581 (5)	0.4233 (5)	0.7789 (4)	0.0513 (10)
H10A	0.6585	0.4211	0.7776	0.062*
H10B	0.8462	0.5203	0.8215	0.062*
C11	0.7950 (4)	0.3128 (4)	0.8509 (3)	0.0458 (9)
C12	0.8030 (5)	0.3159 (5)	0.9693 (4)	0.0571 (11)
C13	0.8391 (6)	0.2189 (6)	1.0401 (5)	0.0745 (14)
H13	0.8461	0.2247	1.1196	0.089*
C14	0.8644 (7)	0.1145 (7)	0.9923 (6)	0.0904 (17)
H14	0.8875	0.0476	1.0391	0.108*
C15	0.8562 (7)	0.1062 (6)	0.8740 (6)	0.0893 (17)
H15	0.8733	0.0343	0.8414	0.107*
C16	0.8225 (6)	0.2060 (5)	0.8060 (5)	0.0657 (12)
H16	0.8182	0.2013	0.7273	0.079*

	U11	U22	U33	U12	U13	U23
P	0.0347 (5)	0.0643 (6)	0.0311 (5)	0.0268 (5)	0.0192 (4)	0.0135 (4)
Cl1	0.1450 (15)	0.226 (2)	0.0426 (7)	0.1471 (16)	−0.0041 (8)	−0.0079 (9)
Cl2	0.1193 (13)	0.0728 (9)	0.1247 (14)	0.0485 (9)	0.0318 (11)	−0.0113 (9)
Cl3	0.0902 (10)	0.0832 (9)	0.1143 (12)	0.0446 (8)	0.0567 (9)	0.0103 (8)
Cl4	0.1089 (10)	0.1091 (10)	0.0488 (7)	0.0593 (9)	0.0469 (7)	0.0242 (6)
O1	0.0390 (14)	0.097 (2)	0.0371 (14)	0.0384 (15)	0.0170 (12)	0.0138 (14)
O2	0.0404 (15)	0.119 (3)	0.0490 (17)	0.0405 (17)	0.0219 (13)	0.0053 (16)
N1	0.0538 (19)	0.060 (2)	0.0360 (17)	0.0223 (16)	0.0241 (15)	0.0118 (14)
N2	0.0367 (16)	0.069 (2)	0.0332 (16)	0.0281 (15)	0.0206 (13)	0.0093 (14)
N3	0.0443 (17)	0.062 (2)	0.0473 (19)	0.0251 (16)	0.0272 (15)	0.0121 (15)
C1	0.050 (2)	0.064 (2)	0.041 (2)	0.029 (2)	0.0177 (18)	0.0055 (18)
C2	0.0390 (19)	0.060 (2)	0.0346 (19)	0.0248 (18)	0.0187 (16)	0.0131 (16)
C3	0.050 (2)	0.058 (3)	0.061 (3)	0.018 (2)	0.017 (2)	0.008 (2)
C4	0.048 (2)	0.045 (2)	0.060 (3)	0.0138 (18)	0.025 (2)	0.0131 (18)
C5	0.052 (2)	0.047 (2)	0.065 (3)	0.0174 (19)	0.027 (2)	0.012 (2)
C6	0.062 (3)	0.059 (3)	0.084 (4)	0.024 (2)	0.018 (3)	0.022 (3)
C7	0.089 (4)	0.073 (3)	0.067 (3)	0.019 (3)	0.029 (3)	0.016 (3)
C8	0.103 (4)	0.075 (3)	0.078 (4)	0.024 (3)	0.058 (3)	0.013 (3)
C9	0.069 (3)	0.062 (3)	0.086 (4)	0.029 (2)	0.046 (3)	0.021 (2)
C10	0.058 (2)	0.068 (3)	0.041 (2)	0.031 (2)	0.0303 (19)	0.0182 (19)
C11	0.039 (2)	0.059 (2)	0.041 (2)	0.0201 (18)	0.0203 (17)	0.0160 (17)
C12	0.050 (2)	0.075 (3)	0.047 (2)	0.027 (2)	0.0222 (19)	0.021 (2)
C13	0.070 (3)	0.092 (4)	0.059 (3)	0.034 (3)	0.027 (2)	0.038 (3)
C14	0.095 (4)	0.097 (4)	0.090 (4)	0.056 (4)	0.036 (3)	0.053 (3)
C15	0.097 (4)	0.088 (4)	0.112 (5)	0.059 (3)	0.053 (4)	0.046 (3)
C16	0.069 (3)	0.077 (3)	0.066 (3)	0.038 (3)	0.038 (2)	0.022 (2)

P—O1	1.471 (3)	C5—C6	1.382 (7)
P—N1	1.616 (3)	C6—C7	1.367 (8)
P—N3	1.619 (3)	C6—H6	0.9300
P—N2	1.682 (3)	C7—C8	1.354 (8)
Cl1—C1	1.718 (4)	C7—H7	0.9300
Cl2—C1	1.748 (4)	C8—C9	1.388 (7)
Cl3—C5	1.741 (5)	C8—H8	0.9300
Cl4—C12	1.733 (5)	C9—H9	0.9300
O2—C2	1.208 (4)	C10—C11	1.500 (5)
N1—C10	1.450 (5)	C10—H10A	0.9700
N1—H1	0.8600	C10—H10B	0.9700
N2—C2	1.349 (4)	C11—C16	1.376 (6)
N2—H2	0.8600	C11—C12	1.394 (5)
N3—C3	1.461 (5)	C12—C13	1.375 (6)
N3—H3	0.8600	C13—C14	1.358 (8)
C1—C2	1.525 (5)	C13—H13	0.9300
C1—H1A	0.9800	C14—C15	1.392 (8)
C3—C4	1.509 (6)	C14—H14	0.9300
C3—H3A	0.9700	C15—C16	1.373 (7)
C3—H3B	0.9700	C15—H15	0.9300
C4—C5	1.381 (6)	C16—H16	0.9300
C4—C9	1.392 (6)
O1—P—N1	117.84 (17)	C7—C6—C5	119.7 (5)
O1—P—N3	110.86 (18)	C7—C6—H6	120.1
N1—P—N3	106.48 (17)	C5—C6—H6	120.1
O1—P—N2	106.38 (15)	C8—C7—C6	119.7 (5)
N1—P—N2	103.08 (16)	C8—C7—H7	120.2
N3—P—N2	112.03 (16)	C6—C7—H7	120.2
C10—N1—P	123.7 (3)	C7—C8—C9	120.7 (5)
C10—N1—H1	118.2	C7—C8—H8	119.7
P—N1—H1	118.2	C9—C8—H8	119.7
C2—N2—P	126.3 (2)	C4—C9—C8	121.3 (5)
C2—N2—H2	116.9	C4—C9—H9	119.3
P—N2—H2	116.9	C8—C9—H9	119.3
C3—N3—P	122.2 (3)	N1—C10—C11	114.6 (3)
C3—N3—H3	118.9	N1—C10—H10A	108.6
P—N3—H3	118.9	C11—C10—H10A	108.6
C2—C1—Cl1	111.5 (3)	N1—C10—H10B	108.6
C2—C1—Cl2	109.2 (3)	C11—C10—H10B	108.6
Cl1—C1—Cl2	111.2 (2)	H10A—C10—H10B	107.6
C2—C1—H1A	108.3	C16—C11—C12	117.0 (4)
Cl1—C1—H1A	108.3	C16—C11—C10	123.2 (4)
Cl2—C1—H1A	108.3	C12—C11—C10	119.7 (4)
O2—C2—N2	123.9 (3)	C13—C12—C11	122.2 (5)
O2—C2—C1	123.1 (3)	C13—C12—Cl4	118.4 (4)
N2—C2—C1	113.0 (3)	C11—C12—Cl4	119.4 (3)
N3—C3—C4	113.0 (3)	C12—C13—C14	119.0 (5)
N3—C3—H3A	109.0	C12—C13—H13	120.5
C4—C3—H3A	109.0	C14—C13—H13	120.5
N3—C3—H3B	109.0	C15—C14—C13	120.8 (5)
C4—C3—H3B	109.0	C15—C14—H14	119.6
H3A—C3—H3B	107.8	C13—C14—H14	119.6
C5—C4—C9	116.2 (4)	C14—C15—C16	118.9 (5)
C5—C4—C3	123.2 (4)	C14—C15—H15	120.6
C9—C4—C3	120.5 (4)	C16—C15—H15	120.6
C4—C5—C6	122.5 (4)	C11—C16—C15	122.0 (5)
C4—C5—Cl3	119.7 (4)	C11—C16—H16	119.0
C6—C5—Cl3	117.8 (4)	C15—C16—H16	119.0
O1—P—N1—C10	66.5 (4)	C4—C5—C6—C7	0.1 (7)
N3—P—N1—C10	−58.7 (3)	Cl3—C5—C6—C7	−179.6 (4)
N2—P—N1—C10	−176.8 (3)	C5—C6—C7—C8	−0.6 (8)
O1—P—N2—C2	−174.1 (3)	C6—C7—C8—C9	0.4 (8)
N1—P—N2—C2	61.3 (4)	C5—C4—C9—C8	−0.7 (6)
N3—P—N2—C2	−52.8 (4)	C3—C4—C9—C8	175.8 (4)
O1—P—N3—C3	44.0 (3)	C7—C8—C9—C4	0.3 (8)
N1—P—N3—C3	173.4 (3)	P—N1—C10—C11	−121.2 (3)
N2—P—N3—C3	−74.6 (3)	N1—C10—C11—C16	5.6 (6)
P—N2—C2—O2	−4.7 (6)	N1—C10—C11—C12	−174.5 (4)
P—N2—C2—C1	176.0 (3)	C16—C11—C12—C13	1.0 (6)
Cl1—C1—C2—O2	17.2 (5)	C10—C11—C12—C13	−178.9 (4)
Cl2—C1—C2—O2	−106.1 (4)	C16—C11—C12—Cl4	179.6 (3)
Cl1—C1—C2—N2	−163.5 (3)	C10—C11—C12—Cl4	−0.3 (5)
Cl2—C1—C2—N2	73.2 (4)	C11—C12—C13—C14	−1.4 (7)
P—N3—C3—C4	87.6 (4)	Cl4—C12—C13—C14	179.9 (4)
N3—C3—C4—C5	83.3 (5)	C12—C13—C14—C15	0.8 (9)
N3—C3—C4—C9	−93.0 (5)	C13—C14—C15—C16	0.2 (9)
C9—C4—C5—C6	0.5 (6)	C12—C11—C16—C15	0.1 (7)
C3—C4—C5—C6	−175.9 (4)	C10—C11—C16—C15	180.0 (5)
C9—C4—C5—Cl3	−179.7 (3)	C14—C15—C16—C11	−0.7 (8)
C3—C4—C5—Cl3	3.9 (5)

D—H···A	D—H	H···A	D···A	D—H···A
N2—H2···O1i	0.86	1.93	2.756 (4)	162
N3—H3···O2ii	0.86	2.24	3.024 (4)	151

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N2—H2⋯O1i	0.86	1.93	2.756 (4)	162
N3—H3⋯O2ii	0.86	2.24	3.024 (4)	151

Symmetry codes: (i) ; (ii) .