N,N'-Bis(4-methyl-phen-yl)-N''-(2,2,2-trichloro-acet-yl)phospho-ric triamide.

The P atom in the title compound, C(16)H(17)Cl(3)N(3)O(2)P, is bonded in a distorted tetra-hedral geometry with the phosphoryl and carbonyl groups anti with respect to one another. In the crystal, mol-ecules are linked through (N-H)(2)⋯O(=P) and N-H⋯O(=C) hydrogen bonds into chains along [001]. The phosphoryl O atom acts as a double hydrogen-bond acceptor.

Related literature

For phospho­ric triamides having a C(=O)NHP(=O) skeleton, see: Pourayoubi et al. (2011 ▶). For the definition of a double hydrogen-bond acceptor, see: Steiner (2002 ▶); Pourayoubi et al. (2012 ▶).

Experimental

Crystal data

C16H17Cl3N3O2P

M = 420.65

Monoclinic,

a = 17.5151 (6) Å

b = 10.8638 (4) Å

c = 9.8615 (3) Å

β = 97.565 (3)°

V = 1860.12 (11) Å3

Z = 4

Mo Kα radiation

μ = 0.59 mm−1

T = 120 K

0.60 × 0.60 × 0.60 mm

Data collection

Oxford Diffraction Xcalibur Sapphire2 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.955, T max = 1.000

6796 measured reflections

3265 independent reflections

2820 reflections with I > 2σ(I)

R int = 0.013

Refinement

R[F 2 > 2σ(F 2)] = 0.028

wR(F 2) = 0.072

S = 1.04

3265 reflections

240 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.33 e Å−3

Δρmin = −0.26 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis pan class="Disease">RED (Oxford Diffraction, 2009 ▶); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: enCIFer (Allen et al., 2004) ▶.

Crystal structure: contains datablock(s) I, global. DOI: 10.1107/S160053681202154X/lh5469sup1.cif

Structure factors: contains datablock(s) I. DOI: 10.1107/S160053681202154X/lh5469Isup2.hkl

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

C16H17Cl3N3O2P	F(000) = 864
Mr = 420.65	Dx = 1.502 Mg m−3
Monoclinic, P21/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -P 2ybc	Cell parameters from 5060 reflections
a = 17.5151 (6) Å	θ = 3.3–27.7°
b = 10.8638 (4) Å	µ = 0.59 mm−1
c = 9.8615 (3) Å	T = 120 K
β = 97.565 (3)°	Prism, colourless
V = 1860.12 (11) Å3	0.60 × 0.60 × 0.60 mm
Z = 4

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3265 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2820 reflections with I > 2σ(I)
Graphite monochromator	Rint = 0.013
Detector resolution: 8.4353 pixels mm-1	θmax = 25.0°, θmin = 3.5°
ω scan	h = −20→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −12→12
Tmin = 0.955, Tmax = 1.000	l = −11→11
6796 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)] = 0.028	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	w = 1/[σ2(Fo2) + (0.0371P)2 + 0.8844P] where P = (Fo2 + 2Fc2)/3
3265 reflections	(Δ/σ)max = 0.001
240 parameters	Δρmax = 0.33 e Å−3
0 restraints	Δρmin = −0.26 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
Cl1	0.42010 (3)	0.60382 (4)	0.43562 (4)	0.02457 (13)
O1	0.14643 (7)	0.76151 (12)	0.35677 (12)	0.0207 (3)
P1	0.17851 (3)	0.74597 (4)	0.50145 (4)	0.01634 (12)
C1	0.12216 (10)	0.51775 (18)	0.53131 (17)	0.0191 (4)
N1	0.13973 (9)	0.63843 (15)	0.58334 (15)	0.0190 (3)
Cl2	0.46136 (3)	0.60149 (5)	0.72774 (4)	0.02712 (13)
O2	0.30612 (7)	0.68782 (12)	0.72621 (12)	0.0225 (3)
C2	0.07280 (11)	0.5003 (2)	0.41018 (18)	0.0246 (4)
H2	0.0532	0.5692	0.3573	0.030*
N2	0.17663 (9)	0.86377 (15)	0.60406 (16)	0.0187 (3)
Cl3	0.44563 (3)	0.83378 (5)	0.58356 (5)	0.02685 (13)
C3	0.05233 (11)	0.3820 (2)	0.3671 (2)	0.0287 (5)
H3	0.0200	0.3709	0.2829	0.034*
N3	0.27364 (9)	0.71385 (15)	0.49795 (15)	0.0182 (3)
C4	0.07772 (11)	0.2797 (2)	0.4435 (2)	0.0292 (5)
C5	0.12832 (12)	0.2987 (2)	0.5623 (2)	0.0335 (5)
H5	0.1480	0.2298	0.6151	0.040*
C6	0.15074 (11)	0.41629 (19)	0.6055 (2)	0.0276 (5)
H6	0.1859	0.4270	0.6865	0.033*
C7	0.22672 (10)	0.96637 (17)	0.60665 (17)	0.0180 (4)
C8	0.25836 (11)	1.00236 (18)	0.49043 (18)	0.0228 (4)
H8	0.2465	0.9582	0.4072	0.027*
C9	0.30726 (12)	1.10297 (18)	0.4972 (2)	0.0258 (4)
H9	0.3296	1.1253	0.4180	0.031*
C10	0.32484 (11)	1.17239 (18)	0.61502 (19)	0.0250 (4)
C11	0.29305 (12)	1.13365 (19)	0.7299 (2)	0.0280 (5)
H11	0.3047	1.1781	0.8130	0.034*
C12	0.24498 (11)	1.03244 (18)	0.72679 (18)	0.0237 (4)
H12	0.2244	1.0081	0.8072	0.028*
C13	0.05026 (13)	0.1515 (2)	0.4026 (3)	0.0414 (6)
H13A	0.0835	0.0908	0.4550	0.062*
H13B	0.0523	0.1396	0.3047	0.062*
H13C	−0.0029	0.1410	0.4217	0.062*
C14	0.37295 (13)	1.2873 (2)	0.6172 (2)	0.0350 (5)
H14A	0.4040	1.2957	0.7069	0.052*
H14B	0.3392	1.3590	0.5998	0.052*
H14C	0.4071	1.2819	0.5462	0.052*
C15	0.32379 (10)	0.69330 (17)	0.61173 (17)	0.0175 (4)
C16	0.40963 (10)	0.68105 (17)	0.58949 (17)	0.0192 (4)
H1N	0.1460 (12)	0.6449 (19)	0.662 (2)	0.023 (6)*
H2N	0.1638 (12)	0.848 (2)	0.672 (2)	0.026 (6)*
H3N	0.2878 (12)	0.720 (2)	0.430 (2)	0.027 (6)*

	U11	U22	U33	U12	U13	U23
Cl1	0.0236 (2)	0.0341 (3)	0.0165 (2)	0.0062 (2)	0.00442 (17)	−0.00528 (19)
O1	0.0204 (6)	0.0296 (7)	0.0124 (6)	−0.0004 (6)	0.0027 (5)	0.0013 (5)
P1	0.0169 (2)	0.0216 (3)	0.0107 (2)	−0.0005 (2)	0.00235 (17)	0.00029 (18)
C1	0.0155 (9)	0.0273 (10)	0.0154 (8)	−0.0044 (8)	0.0054 (7)	−0.0026 (8)
N1	0.0243 (8)	0.0253 (9)	0.0076 (7)	−0.0037 (7)	0.0025 (6)	−0.0019 (7)
Cl2	0.0263 (3)	0.0359 (3)	0.0180 (2)	0.0092 (2)	−0.00139 (18)	0.00249 (19)
O2	0.0227 (7)	0.0329 (8)	0.0125 (6)	0.0018 (6)	0.0047 (5)	0.0003 (5)
C2	0.0218 (10)	0.0349 (12)	0.0168 (9)	−0.0005 (9)	0.0010 (7)	−0.0019 (8)
N2	0.0224 (8)	0.0230 (9)	0.0118 (7)	−0.0006 (7)	0.0064 (6)	0.0011 (7)
Cl3	0.0271 (3)	0.0285 (3)	0.0252 (2)	−0.0063 (2)	0.00431 (19)	−0.00010 (19)
C3	0.0214 (10)	0.0447 (13)	0.0199 (10)	−0.0068 (10)	0.0015 (8)	−0.0129 (9)
N3	0.0196 (8)	0.0263 (9)	0.0099 (8)	0.0011 (7)	0.0059 (6)	0.0006 (6)
C4	0.0211 (10)	0.0318 (12)	0.0350 (11)	−0.0031 (9)	0.0050 (8)	−0.0110 (9)
C5	0.0296 (11)	0.0267 (11)	0.0411 (12)	−0.0014 (10)	−0.0065 (9)	−0.0007 (10)
C6	0.0271 (11)	0.0277 (11)	0.0254 (10)	−0.0017 (9)	−0.0062 (8)	−0.0013 (8)
C7	0.0173 (9)	0.0186 (9)	0.0177 (9)	0.0027 (8)	0.0011 (7)	0.0023 (7)
C8	0.0298 (10)	0.0225 (10)	0.0164 (9)	0.0016 (9)	0.0039 (7)	0.0014 (8)
C9	0.0287 (10)	0.0237 (11)	0.0262 (10)	0.0006 (9)	0.0080 (8)	0.0065 (8)
C10	0.0216 (10)	0.0229 (10)	0.0292 (10)	0.0010 (8)	−0.0018 (8)	0.0059 (8)
C11	0.0352 (11)	0.0249 (11)	0.0220 (10)	−0.0029 (9)	−0.0033 (8)	−0.0010 (8)
C12	0.0289 (10)	0.0259 (10)	0.0160 (9)	−0.0006 (9)	0.0025 (7)	0.0020 (8)
C13	0.0329 (12)	0.0363 (13)	0.0537 (15)	−0.0078 (11)	0.0003 (11)	−0.0157 (11)
C14	0.0323 (12)	0.0326 (12)	0.0386 (12)	−0.0074 (10)	−0.0010 (9)	0.0042 (10)
C15	0.0205 (9)	0.0174 (9)	0.0146 (9)	0.0002 (8)	0.0026 (7)	−0.0012 (7)
C16	0.0206 (9)	0.0226 (10)	0.0144 (9)	0.0007 (8)	0.0024 (7)	−0.0014 (7)

Cl1—C16	1.7644 (18)	C5—C6	1.387 (3)
O1—P1	1.4727 (12)	C5—H5	0.9500
P1—N1	1.6195 (16)	C6—H6	0.9500
P1—N2	1.6345 (16)	C7—C12	1.386 (3)
P1—N3	1.7071 (16)	C7—C8	1.393 (2)
C1—C6	1.380 (3)	C8—C9	1.385 (3)
C1—C2	1.392 (2)	C8—H8	0.9500
C1—N1	1.427 (2)	C9—C10	1.385 (3)
N1—H1N	0.77 (2)	C9—H9	0.9500
Cl2—C16	1.7611 (18)	C10—C11	1.392 (3)
O2—C15	1.211 (2)	C10—C14	1.505 (3)
C2—C3	1.386 (3)	C11—C12	1.383 (3)
C2—H2	0.9500	C11—H11	0.9500
N2—C7	1.417 (2)	C12—H12	0.9500
N2—H2N	0.76 (2)	C13—H13A	0.9800
Cl3—C16	1.7786 (19)	C13—H13B	0.9800
C3—C4	1.383 (3)	C13—H13C	0.9800
C3—H3	0.9500	C14—H14A	0.9800
N3—C15	1.349 (2)	C14—H14B	0.9800
N3—H3N	0.75 (2)	C14—H14C	0.9800
C4—C5	1.388 (3)	C15—C16	1.553 (2)
C4—C13	1.510 (3)
O1—P1—N1	115.74 (8)	C9—C8—C7	119.49 (18)
O1—P1—N2	118.28 (8)	C9—C8—H8	120.3
N1—P1—N2	102.25 (8)	C7—C8—H8	120.3
O1—P1—N3	104.64 (7)	C8—C9—C10	122.55 (18)
N1—P1—N3	109.71 (8)	C8—C9—H9	118.7
N2—P1—N3	105.77 (8)	C10—C9—H9	118.7
C6—C1—C2	119.16 (18)	C9—C10—C11	116.71 (18)
C6—C1—N1	119.83 (16)	C9—C10—C14	121.72 (18)
C2—C1—N1	120.91 (17)	C11—C10—C14	121.51 (18)
C1—N1—P1	124.64 (12)	C12—C11—C10	122.02 (18)
C1—N1—H1N	116.1 (16)	C12—C11—H11	119.0
P1—N1—H1N	114.9 (16)	C10—C11—H11	119.0
C3—C2—C1	119.68 (19)	C11—C12—C7	120.13 (17)
C3—C2—H2	120.2	C11—C12—H12	119.9
C1—C2—H2	120.2	C7—C12—H12	119.9
C7—N2—P1	124.35 (12)	C4—C13—H13A	109.5
C7—N2—H2N	114.8 (17)	C4—C13—H13B	109.5
P1—N2—H2N	113.8 (17)	H13A—C13—H13B	109.5
C4—C3—C2	121.81 (18)	C4—C13—H13C	109.5
C4—C3—H3	119.1	H13A—C13—H13C	109.5
C2—C3—H3	119.1	H13B—C13—H13C	109.5
C15—N3—P1	123.18 (13)	C10—C14—H14A	109.5
C15—N3—H3N	120.2 (17)	C10—C14—H14B	109.5
P1—N3—H3N	116.2 (17)	H14A—C14—H14B	109.5
C3—C4—C5	117.62 (19)	C10—C14—H14C	109.5
C3—C4—C13	121.82 (19)	H14A—C14—H14C	109.5
C5—C4—C13	120.5 (2)	H14B—C14—H14C	109.5
C6—C5—C4	121.3 (2)	O2—C15—N3	124.41 (16)
C6—C5—H5	119.3	O2—C15—C16	119.89 (15)
C4—C5—H5	119.3	N3—C15—C16	115.66 (14)
C1—C6—C5	120.31 (18)	C15—C16—Cl2	109.98 (12)
C1—C6—H6	119.8	C15—C16—Cl1	111.97 (12)
C5—C6—H6	119.8	Cl2—C16—Cl1	109.34 (10)
C12—C7—C8	119.06 (17)	C15—C16—Cl3	106.17 (12)
C12—C7—N2	119.70 (16)	Cl2—C16—Cl3	109.57 (10)
C8—C7—N2	121.24 (16)	Cl1—C16—Cl3	109.75 (9)
C6—C1—N1—P1	125.17 (17)	P1—N2—C7—C12	−152.11 (15)
C2—C1—N1—P1	−58.6 (2)	P1—N2—C7—C8	27.7 (2)
O1—P1—N1—C1	44.72 (17)	C12—C7—C8—C9	0.0 (3)
N2—P1—N1—C1	174.73 (14)	N2—C7—C8—C9	−179.82 (17)
N3—P1—N1—C1	−73.35 (16)	C7—C8—C9—C10	−1.7 (3)
C6—C1—C2—C3	0.9 (3)	C8—C9—C10—C11	2.3 (3)
N1—C1—C2—C3	−175.35 (16)	C8—C9—C10—C14	−174.99 (19)
O1—P1—N2—C7	−75.36 (16)	C9—C10—C11—C12	−1.3 (3)
N1—P1—N2—C7	156.22 (14)	C14—C10—C11—C12	176.03 (19)
N3—P1—N2—C7	41.39 (16)	C10—C11—C12—C7	−0.3 (3)
C1—C2—C3—C4	2.0 (3)	C8—C7—C12—C11	1.0 (3)
O1—P1—N3—C15	179.94 (15)	N2—C7—C12—C11	−179.19 (17)
N1—P1—N3—C15	−55.29 (17)	P1—N3—C15—O2	4.8 (3)
N2—P1—N3—C15	54.30 (17)	P1—N3—C15—C16	−172.98 (13)
C2—C3—C4—C5	−3.5 (3)	O2—C15—C16—Cl2	23.4 (2)
C2—C3—C4—C13	174.88 (19)	N3—C15—C16—Cl2	−158.68 (14)
C3—C4—C5—C6	2.1 (3)	O2—C15—C16—Cl1	145.21 (15)
C13—C4—C5—C6	−176.3 (2)	N3—C15—C16—Cl1	−36.9 (2)
C2—C1—C6—C5	−2.3 (3)	O2—C15—C16—Cl3	−95.03 (18)
N1—C1—C6—C5	174.01 (18)	N3—C15—C16—Cl3	82.86 (17)
C4—C5—C6—C1	0.8 (3)

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1i	0.77 (2)	2.17 (2)	2.8953 (19)	156 (2)
N2—H2N···O1i	0.76 (2)	2.23 (2)	2.948 (2)	159 (2)
N3—H3N···O2ii	0.75 (2)	2.31 (2)	3.008 (2)	157 (2)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1i	0.77 (2)	2.17 (2)	2.8953 (19)	156 (2)
N2—H2N⋯O1i	0.76 (2)	2.23 (2)	2.948 (2)	159 (2)
N3—H3N⋯O2ii	0.75 (2)	2.31 (2)	3.008 (2)	157 (2)

Symmetry codes: (i) ; (ii) .