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

Ovchynnikov, V.A.

doi:10.1107/S1600536810017873

organic compounds

CRYSTALLOGRAPHIC
COMMUNICATIONS

ISSN: 2056-9890

Volume 66| Part 6| June 2010| Page o1425

https://doi.org/10.1107/S1600536810017873

Open

access

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

Vladimir A. Ovchynnikov ^a ^*

^aNational Taras Shevchenko University, Department of Chemistry, Volodymyrska str. 64, 01033 Kyiv, Ukraine
^*Correspondence e-mail: ovchynnikov@univ.kiev.ua

(Received 31 March 2010; accepted 14 May 2010; online 22 May 2010)

In the title compound, C₁₆H₁₇Cl₃N₃O₂P, the P atom has a slightly distorted tetrahedral configuration. The conformations of the carbonyl and phosphoryl groups are anti to each other. In the crystal, intermolecular N—H⋯O hydrogen bonds link the molecules 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_r = 420.65
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.038
wR(F²) = 0.103
S = 1.05
3286 reflections
226 parameters
H-atom parameters constrained
Δρ_max = 0.62 e Å⁻³
Δρ_min = −0.41 e Å⁻³

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) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1.

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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.

Supporting information

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

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810017873/dn2554Isup2.hkl

checkCIF report

Comment top

Carbacylamidophosphates of the general formula RC(O)NHP(O)R₂ are potential new ligands for metal ions (Skopenko et al., 1996; Ovchynnikov et al., 1998; Znovjak et al., 2009; Gubina et al., 2009; Amirkhanov et al., 1997a; Gowda et al., 2010; Safin et al., 2009). Many of these compounds also show biological activity, including anticancer activity (Amirkhanov et al., 1996; Rebrova et al., 1982). This work reports the structure of N,N'-dibenzyl-N"-trichloroacetylphosphortriamide (HDBA).

In the title compound, the phosphorus atom has a slightly distorted tetrahedral configuration (Fig.1). The average values of the angles OPN in the molecule are larger than tetrahedral, while the N – P – N angles are smaller, with the exception O1 – P1– N1 106.85 (7) ° and N(1) – P1– N(2) 112.32 (7) °, which can be rationalized by the influence of the hydrogen bonds. The environment of the nitrogen atoms is practically planar with only slight deviations from the mean planes.

The bond length P ═O (1.479 (1) Å is longer than in the compounds with alkyl amide substituents (the range of bond length d_(P_═_O) 1.475 - 1.478 Å) (Amirkhanov et al., 1997b). In the structure the carbonyl and phosphoryl groups are anti to each other as in most carbacylamidophosphates.

The fragment including the atoms O(2), N(1), C(1), C(2) is virtually planar, with only slight deviations from the mean plane. The phosphorus and oxygen atom of the phosphoryl group do not fit into this plane. Close enough to this plane lie the hydrogen H(1 N) and one of the chlorine atoms Cl(3). The carbonyl oxygen-phosphorus distance 3.023 (1) Å is considerably shorter than the sum of Van der Waals radii (3.3 Å).

Molecules are linked by hydrogen bonds of the phosphorylic oxygen atoms and the hydrogen atoms of the C(O)N(H)P(O) groups of neighboring molecules. The N—H···O intermolecular hydrogen bonds pack the molecules into infinite chains parallel to the b axis (Table 1, Fig.2).

Related literature top

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 ligand, see: Kirsanov & Derkach (1956).

Experimental top

The solution of benzylamine (26.8 g, 0.25 mol) in 30 ml of chloroform was cooled to 10 °C and a solution of the dichloride of trichloroacetylamidophosphoric acid (14 g, 0.047 mol) in 150 ml of chloroform was added slowly with stirring. The temperature was not allowed to rise above 15 °C. Stirring was continued for about 40 min. The resulting mixture, containing HL, H₂NCH₂C₆H₅*HCl and excess dibenzylamine, was filtered from the precipitate (H₂NCH₂C₆H₅*HCl). Then the solution was evaporated and the residue was treated with aqueous HCl; the product precipitated as a yellow crystalline powder (90 % yield) (Kirsanov & Derkach, 1956). A colourless crystalline compound was obtained after recristallization from acetone. The compound is air stable, soluble in alcohols and hot acetone, insoluble in non-polar aprotic solvents and water, M.p. = 144 °C. Anal. Calc.: C 45.68,H 4.07, N 9.99; Found: C 45.73, H 3.95, N 9.85. IR (KBr pellet, cm^-1): 1709 (s, CO) and 1250 (s, PO).

Structure description top

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 ligand, see: Kirsanov & Derkach (1956).

Computing details top

Data collection: CrysAlis CCD (Oxford Diffraction, 2009); cell refinement: CrysAlis RED (Oxford Diffraction, 2009); data reduction: CrysAlis RED (Oxford Diffraction, 2009); 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 (Sheldrick, 2008).

Figures top

	Fig. 1. Molecular structure of the title compound with the atom labeling scheme. Ellipsoids are drawn at the 50% probability level. H atoms are represented as small spheres of arbitrary radii.
	Fig. 2. Partial packing view showing the hydrogen bonds pattern. Hydrogen bonds are shown as dashed lines. H atoms not involved in hydrogen bondings have been omitted for clarity. [Symmetry codes: (i) -x+1, -y+1, -z+1; (ii) -x+1, -y+2, -z+1]

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

Crystal data top

C₁₆H₁₇Cl₃N₃O₂P	Z = 2
M_r = 420.65	F(000) = 432
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	3286 independent reflections
Radiation source: Enhance (Mo) X-ray Source	3069 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 16.1827 pixels mm^-1	θ_max = 25.0°, θ_min = 2.0°
ω scans	h = −8→10
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −10→12
T_min = 0.893, T_max = 0.893	l = −13→13
4976 measured reflections

Refinement top

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(F_o²) + (0.0496P)² + 0.7601P] where P = (F_o² + 2F_c²)/3
3286 reflections	(Δ/σ)_max < 0.001
226 parameters	Δρ_max = 0.62 e Å⁻³
0 restraints	Δρ_min = −0.41 e Å⁻³

Crystal data top

C₁₆H₁₇Cl₃N₃O₂P	γ = 86.469 (1)°
M_r = 420.65	V = 952.13 (3) Å³
Triclinic, P1	Z = 2
a = 9.116 Å	Mo Kα radiation
b = 10.3586 (2) Å	µ = 0.58 mm⁻¹
c = 11.7713 (2) Å	T = 293 K
α = 68.320 (1)°	0.20 × 0.20 × 0.20 mm
β = 67.762 (1)°

Data collection top

Oxford Diffraction Xcalibur3 diffractometer	3286 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	3069 reflections with I > 2σ(I)
T_min = 0.893, T_max = 0.893	R_int = 0.016
4976 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.038	0 restraints
wR(F²) = 0.103	H-atom parameters constrained
S = 1.05	Δρ_max = 0.62 e Å⁻³
3286 reflections	Δρ_min = −0.41 e Å⁻³
226 parameters

Special details top

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.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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

Hydrogen-bond geometry (Å, º) top

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) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇Cl₃N₃O₂P
M_r	420.65
Crystal system, space group	Triclinic, P1
Temperature (K)	293
a, b, c (Å)	9.116, 10.3586 (2), 11.7713 (2)
α, β, γ (°)	68.320 (1), 67.762 (1), 86.469 (1)
V (Å³)	952.13 (3)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.58
Crystal size (mm)	0.20 × 0.20 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur3
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.893, 0.893
No. of measured, independent and observed [I > 2σ(I)] reflections	4976, 3286, 3069
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.038, 0.103, 1.05
No. of reflections	3286
No. of parameters	226
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.62, −0.41

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O1ⁱ	0.86	1.95	2.790 (2)	166.6
N2—H2···O2ⁱⁱ	0.86	2.23	3.055 (2)	160.7

Symmetry codes: (i) −x+1, −y+1, −z+1; (ii) −x+1, −y+2, −z+1.

Acknowledgements

The author thanks Professor Joachim Sieler for his help with the data collection.

References

Amirkhanov, V. M., Ovchynnikov, V. A., Glowiak, T. & Kozlowski, H. (1997b). Z. Naturforsch. Teil B, 52, 1331–1336. CAS Google Scholar
Amirkhanov, V., Ovchynnikov, V., Legendziewicz, J., Graczyk, A., Hanuza, J. & Macalik, L. (1996). Acta Phys. Pol. 90, 455–460. CAS Google Scholar
Amirkhanov, V. M., Ovchynnikov, V. A., Turov, A. V. & Skopenko, V. V. (1997a). Zh. Obshch. Khim. 23, 139–142. Google Scholar
Burnett, M. N. & Johnson, C. K. (1996). ORTEPIII. Report ORNL-6895. Oak Ridge National Laboratory, Tennessee, USA. Google Scholar
Farrugia, L. J. (1997). J. Appl. Cryst. 30, 565. CrossRef IUCr Journals Google Scholar
Gowda, B. T., Foro, S., Suchetan, P. A. & Fuess, H. (2010). Acta Cryst. E66, o747. Web of Science CSD CrossRef IUCr Journals Google Scholar
Gubina, K. E., Maslov, O. A., Trush, E. A., Trush, V. A., Ovchynnikov, V. A., Shishkina, S. V. & Amirkhanov, V. M. (2009). Polyhedron, 28, 2661–2666. Web of Science CSD CrossRef CAS Google Scholar
Kirsanov, A. & Derkach, G. (1956). Zh. Obshch. Khim. 28, 2247–2250. Google Scholar
Ovchynnikov, V. A., Amirkhanov, V. M., Kapshuk, A. A., Sliva, T. Yu., Glowiak, T. & Kozlowski, H. (1998). Z. Naturforsch. Teil B, 53, 836–840. CAS Google Scholar
Oxford Diffraction (2009). CrysAlis RED and CrysAlis CCD. Oxford Diffraction Ltd, Yarnton, England. Google Scholar
Rebrova, O. H., Biyushkin, V. N., Malinovskiy, T. I., Procenko, L. D. & Dneprova, T. N. (1982). Dokl. Akad. Nauk SSSR, 266, 1391–1395. CAS Google Scholar
Safin, D. A., Bolte, M., Shakirova, E. R. & Babashkina, M. G. (2009). Polyhedron, 28, 501–504. Web of Science CSD CrossRef CAS Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar
Skopenko, V. V., Amirkhanov, V. M., Ovchinnikov, V. A. & Turov, A. V. (1996). Russ. J. Inorg. Chem. 41, 611–616. CAS Google Scholar
Spek, A. L. (2009). Acta Cryst. D65, 148–155. Web of Science CrossRef CAS IUCr Journals Google Scholar
Znovjak, K. O., Moroz, O. V., Ovchynnikov, V. A., Sliva, T. Yu., Shishkina, S. V. & Amirkhanov, V. M. (2009). Polyhedron, 28, 3731–3738. Google Scholar