N-[Bis(benzylamino)phosphoryl]-2,2,2-trichloroacetamide.

In the title compound, C(16)H(17)Cl(3)N(3)O(2)P, the P atom has a slightly distorted tetra-hedral configuration. The conformations of the carbonyl and phosphoryl groups are anti to each other. In the crystal, inter-molecular N-H⋯O hydrogen bonds link the mol-ecules into infinite chains parallel to the b axis.

Related literature

For the use of carbacyl­amido­phosphates as potential new ligands, see: Skopenko et al. (1996 ▶); Ovchynnikov et al. (1998 ▶); Znovjak et al. (2009 ▶); Gubina et al. (2009 ▶); Gowda et al. (2010 ▶); Amirkhanov et al. (1997a ▶); Safin et al. (2009 ▶). For their biological activity, see: Amirkhanov et al. (1996 ▶); Rebrova et al. (1982 ▶). For P=O bond lengths, see: Amirkhanov et al. (1997b ▶). For the synthesis of the title compound, see: Kirsanov & Derkach (1956 ▶).

Experimental

Crystal data

C16H17Cl3N3O2P

M = 420.65

Triclinic,

a = 9.116 Å

b = 10.3586 (2) Å

c = 11.7713 (2) Å

α = 68.320 (1)°

β = 67.762 (1)°

γ = 86.469 (1)°

V = 952.13 (3) Å3

Z = 2

Mo Kα radiation

μ = 0.58 mm−1

T = 293 K

0.20 × 0.20 × 0.20 mm

Data collection

Oxford Diffraction Xcalibur3 diffractometer

Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009 ▶) T min = 0.893, T max = 0.893

4976 measured reflections

3286 independent reflections

3069 reflections with I > 2σ(I)

R int = 0.016

Refinement

R[F 2 > 2σ(F 2)] = 0.038

wR(F 2) = 0.103

S = 1.05

3286 reflections

226 parameters

H-atom parameters constrained

Δρmax = 0.62 e Å−3

Δρmin = −0.41 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 ▶); cell refinement: CrysAlis 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: ORTEPIII (Burnett & Johnson, 1996 ▶), ORTEP-3 for Windows (Farrugia, 1997 ▶) and PLATON (Spek, 2009 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810017873/dn2554sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810017873/dn2554Isup2.hkl

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

C16H17Cl3N3O2P	Z = 2
Mr = 420.65	F(000) = 432
Triclinic, P1	Dx = 1.467 Mg m−3
Hall symbol: -P 1	Melting point: 417 K
a = 9.116 Å	Mo Kα radiation, λ = 0.71073 Å
b = 10.3586 (2) Å	Cell parameters from 3594 reflections
c = 11.7713 (2) Å	θ = 2.0–27.1°
α = 68.320 (1)°	µ = 0.58 mm−1
β = 67.762 (1)°	T = 293 K
γ = 86.469 (1)°	Block, colorless
V = 952.13 (3) Å3	0.20 × 0.20 × 0.20 mm

Oxford Diffraction Xcalibur3 diffractometer	3286 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3069 reflections with I > 2σ(I)
graphite	Rint = 0.016
Detector resolution: 16.1827 pixels mm-1	θmax = 25.0°, θmin = 2.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −10→12
Tmin = 0.893, Tmax = 0.893	l = −13→13
4976 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)] = 0.038	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.103	H-atom parameters constrained
S = 1.05	w = 1/[σ2(Fo2) + (0.0496P)2 + 0.7601P] where P = (Fo2 + 2Fc2)/3
3286 reflections	(Δ/σ)max < 0.001
226 parameters	Δρmax = 0.62 e Å−3
0 restraints	Δρmin = −0.40 e Å−3

Experimental. CrysAlis RED, (Oxford Diffraction Ltd., 2007) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.

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
Cl1	0.82223 (7)	0.78475 (7)	0.14155 (6)	0.04467 (17)
Cl2	0.49492 (8)	0.81971 (8)	0.16751 (6)	0.0545 (2)
Cl3	0.70636 (11)	1.05737 (6)	0.09763 (7)	0.0681 (3)
P1	0.47348 (6)	0.66397 (5)	0.59367 (5)	0.02713 (15)
O1	0.4132 (2)	0.51582 (15)	0.64581 (15)	0.0401 (4)
O2	0.6029 (2)	0.94775 (15)	0.37756 (16)	0.0434 (4)
N1	0.5631 (2)	0.71538 (17)	0.42584 (16)	0.0305 (4)
H1	0.5828	0.6523	0.3921	0.037*
N2	0.3308 (2)	0.75943 (18)	0.63801 (17)	0.0304 (4)
H2	0.3531	0.8309	0.6511	0.036*
N3	0.6122 (2)	0.7072 (2)	0.63210 (18)	0.0362 (4)
H3	0.7059	0.7349	0.5714	0.043*
C1	0.6048 (2)	0.8506 (2)	0.3430 (2)	0.0292 (4)
C2	0.6555 (3)	0.8776 (2)	0.1924 (2)	0.0331 (5)
C3	0.1656 (3)	0.7297 (3)	0.6568 (2)	0.0411 (5)
H3B	0.0955	0.7694	0.7185	0.049*
H3C	0.1396	0.6294	0.6971	0.049*
C4	0.1320 (2)	0.7852 (2)	0.5313 (2)	0.0351 (5)
C5	0.0480 (3)	0.6995 (3)	0.5043 (2)	0.0449 (6)
H5A	0.0178	0.6069	0.5614	0.054*
C6	0.0088 (3)	0.7505 (3)	0.3932 (3)	0.0522 (7)
H6A	−0.0472	0.6921	0.3767	0.063*
C7	0.0533 (3)	0.8878 (3)	0.3073 (3)	0.0513 (7)
H7A	0.0264	0.9224	0.2334	0.062*
C8	0.1382 (3)	0.9738 (3)	0.3321 (3)	0.0502 (6)
H8A	0.1690	1.0661	0.2742	0.060*
C9	0.1776 (3)	0.9228 (3)	0.4432 (2)	0.0434 (6)
H9A	0.2350	0.9813	0.4585	0.052*
C10	0.5851 (3)	0.7012 (2)	0.7652 (2)	0.0363 (5)
H10A	0.4726	0.6775	0.8196	0.044*
H10B	0.6130	0.7932	0.7587	0.044*
C11	0.6781 (2)	0.5975 (2)	0.8338 (2)	0.0302 (4)
C12	0.7278 (3)	0.4795 (2)	0.8055 (2)	0.0358 (5)
H12A	0.7076	0.4642	0.7395	0.043*
C13	0.8075 (3)	0.3841 (2)	0.8745 (2)	0.0404 (5)
H13A	0.8404	0.3058	0.8542	0.049*
C14	0.8382 (3)	0.4048 (2)	0.9736 (2)	0.0423 (5)
H14A	0.8918	0.3409	1.0195	0.051*
C15	0.7883 (3)	0.5215 (3)	1.0035 (2)	0.0433 (6)
H15A	0.8075	0.5355	1.0704	0.052*
C16	0.7100 (3)	0.6174 (2)	0.9342 (2)	0.0371 (5)
H16A	0.6780	0.6959	0.9544	0.045*

	U11	U22	U33	U12	U13	U23
Cl1	0.0426 (3)	0.0533 (4)	0.0418 (3)	0.0090 (3)	−0.0124 (3)	−0.0263 (3)
Cl2	0.0497 (4)	0.0798 (5)	0.0460 (4)	0.0072 (3)	−0.0276 (3)	−0.0271 (3)
Cl3	0.1147 (7)	0.0268 (3)	0.0370 (3)	−0.0035 (3)	−0.0111 (4)	−0.0010 (3)
P1	0.0396 (3)	0.0197 (3)	0.0240 (3)	0.0032 (2)	−0.0134 (2)	−0.0091 (2)
O1	0.0658 (11)	0.0215 (7)	0.0291 (8)	−0.0007 (7)	−0.0131 (7)	−0.0099 (6)
O2	0.0678 (11)	0.0236 (8)	0.0377 (9)	−0.0044 (7)	−0.0141 (8)	−0.0151 (7)
N1	0.0488 (10)	0.0193 (8)	0.0246 (9)	0.0026 (7)	−0.0129 (8)	−0.0107 (7)
N2	0.0368 (9)	0.0262 (9)	0.0341 (9)	0.0033 (7)	−0.0160 (8)	−0.0152 (7)
N3	0.0347 (10)	0.0469 (11)	0.0271 (9)	0.0040 (8)	−0.0122 (8)	−0.0135 (8)
C1	0.0365 (11)	0.0224 (10)	0.0286 (10)	0.0015 (8)	−0.0121 (9)	−0.0098 (8)
C2	0.0457 (12)	0.0254 (10)	0.0264 (10)	0.0015 (9)	−0.0130 (9)	−0.0083 (8)
C3	0.0354 (12)	0.0466 (13)	0.0325 (12)	−0.0013 (10)	−0.0095 (9)	−0.0083 (10)
C4	0.0267 (10)	0.0426 (12)	0.0342 (11)	0.0029 (9)	−0.0092 (9)	−0.0147 (10)
C5	0.0396 (12)	0.0473 (14)	0.0432 (13)	−0.0063 (10)	−0.0106 (11)	−0.0157 (11)
C6	0.0446 (14)	0.0704 (18)	0.0490 (15)	−0.0061 (12)	−0.0166 (12)	−0.0298 (14)
C7	0.0426 (13)	0.0755 (19)	0.0417 (14)	0.0074 (13)	−0.0215 (11)	−0.0230 (13)
C8	0.0509 (15)	0.0487 (15)	0.0487 (15)	0.0046 (12)	−0.0256 (12)	−0.0091 (12)
C9	0.0460 (13)	0.0406 (13)	0.0484 (14)	0.0012 (10)	−0.0255 (11)	−0.0138 (11)
C10	0.0413 (12)	0.0419 (12)	0.0343 (12)	0.0056 (10)	−0.0176 (10)	−0.0205 (10)
C11	0.0308 (10)	0.0335 (11)	0.0243 (10)	−0.0047 (8)	−0.0079 (8)	−0.0104 (8)
C12	0.0470 (12)	0.0352 (11)	0.0259 (10)	−0.0025 (9)	−0.0126 (9)	−0.0126 (9)
C13	0.0503 (13)	0.0304 (11)	0.0333 (12)	0.0023 (10)	−0.0104 (10)	−0.0096 (9)
C14	0.0462 (13)	0.0383 (13)	0.0347 (12)	0.0011 (10)	−0.0177 (10)	−0.0029 (10)
C15	0.0568 (14)	0.0461 (13)	0.0322 (12)	−0.0040 (11)	−0.0239 (11)	−0.0118 (10)
C16	0.0465 (13)	0.0384 (12)	0.0323 (11)	0.0004 (10)	−0.0166 (10)	−0.0174 (10)

Cl1—C2	1.775 (2)	C6—C7	1.381 (4)
Cl2—C2	1.775 (2)	C6—H6A	0.9300
Cl3—C2	1.763 (2)	C7—C8	1.388 (4)
P1—O1	1.4787 (15)	C7—H7A	0.9300
P1—N2	1.6282 (17)	C8—C9	1.392 (4)
P1—N3	1.6296 (19)	C8—H8A	0.9300
P1—N1	1.7055 (17)	C9—H9A	0.9300
O2—C1	1.213 (2)	C10—C11	1.514 (3)
N1—C1	1.354 (3)	C10—H10A	0.9700
N1—H1	0.8600	C10—H10B	0.9700
N2—C3	1.472 (3)	C11—C12	1.389 (3)
N2—H2	0.8600	C11—C16	1.404 (3)
N3—C10	1.469 (3)	C12—C13	1.389 (3)
N3—H3	0.8600	C12—H12A	0.9300
C1—C2	1.570 (3)	C13—C14	1.387 (3)
C3—C4	1.516 (3)	C13—H13A	0.9300
C3—H3B	0.9700	C14—C15	1.385 (4)
C3—H3C	0.9700	C14—H14A	0.9300
C4—C9	1.391 (3)	C15—C16	1.384 (3)
C4—C5	1.398 (3)	C15—H15A	0.9300
C5—C6	1.391 (4)	C16—H16A	0.9300
C5—H5A	0.9300
O1—P1—N2	111.32 (10)	C7—C6—C5	120.0 (2)
O1—P1—N3	119.71 (10)	C7—C6—H6A	120.0
N2—P1—N3	104.09 (9)	C5—C6—H6A	120.0
O1—P1—N1	106.89 (8)	C6—C7—C8	119.5 (2)
N2—P1—N1	112.12 (9)	C6—C7—H7A	120.2
N3—P1—N1	102.49 (9)	C8—C7—H7A	120.2
C1—N1—P1	123.22 (14)	C7—C8—C9	120.5 (3)
C1—N1—H1	118.4	C7—C8—H8A	119.8
P1—N1—H1	118.4	C9—C8—H8A	119.8
C3—N2—P1	123.37 (15)	C4—C9—C8	120.6 (2)
C3—N2—H2	118.3	C4—C9—H9A	119.7
P1—N2—H2	118.3	C8—C9—H9A	119.7
C10—N3—P1	123.29 (15)	N3—C10—C11	114.51 (18)
C10—N3—H3	118.4	N3—C10—H10A	108.6
P1—N3—H3	118.4	C11—C10—H10A	108.6
O2—C1—N1	124.99 (19)	N3—C10—H10B	108.6
O2—C1—C2	120.05 (18)	C11—C10—H10B	108.6
N1—C1—C2	114.96 (17)	H10A—C10—H10B	107.6
C1—C2—Cl3	109.68 (14)	C12—C11—C16	118.3 (2)
C1—C2—Cl1	109.66 (14)	C12—C11—C10	122.64 (18)
Cl3—C2—Cl1	109.28 (12)	C16—C11—C10	119.02 (19)
C1—C2—Cl2	109.45 (15)	C11—C12—C13	120.7 (2)
Cl3—C2—Cl2	109.43 (12)	C11—C12—H12A	119.6
Cl1—C2—Cl2	109.32 (11)	C13—C12—H12A	119.6
N2—C3—C4	114.92 (18)	C14—C13—C12	120.5 (2)
N2—C3—H3B	108.5	C14—C13—H13A	119.8
C4—C3—H3B	108.5	C12—C13—H13A	119.8
N2—C3—H3C	108.5	C15—C14—C13	119.4 (2)
C4—C3—H3C	108.5	C15—C14—H14A	120.3
H3B—C3—H3C	107.5	C13—C14—H14A	120.3
C9—C4—C5	118.2 (2)	C16—C15—C14	120.3 (2)
C9—C4—C3	121.5 (2)	C16—C15—H15A	119.8
C5—C4—C3	120.2 (2)	C14—C15—H15A	119.8
C6—C5—C4	121.1 (2)	C15—C16—C11	120.8 (2)
C6—C5—H5A	119.4	C15—C16—H16A	119.6
C4—C5—H5A	119.4	C11—C16—H16A	119.6

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1i	0.86	1.95	2.790 (2)	167
N2—H2···O2ii	0.86	2.23	3.055 (2)	161

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O1i	0.86	1.95	2.790 (2)	167
N2—H2⋯O2ii	0.86	2.23	3.055 (2)	161

Symmetry codes: (i) ; (ii) .