N,N′-Bis(4-methyl­phen­yl)-N′′-(2,2,2-trichloro­acet­yl)phospho­ric triamide

Raissi Shabari, A.; Pourayoubi, M.; Fadaei, H.; Nečas, M.; Babiak, M.

doi:10.1107/S160053681202154X

organic compounds

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ISSN: 2056-9890

Volume 68| Part 6| June 2012| Page o1813

doi:10.1107/S160053681202154X

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N,N′-Bis(4-methylphenyl)-N′′-(2,2,2-trichloroacetyl)phosphoric triamide

Akbar Raissi Shabari,^a ^* Mehrdad Pourayoubi,^b Hassan Fadaei,^b Marek Nečas ^c and Michal Babiak ^c

^aFaculty of Chemistry, North Tehran Branch, Islamic Azad University, Tehran, Iran, ^bDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, Iran, and ^cDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
^*Correspondence e-mail: a.raissi_shabari@yahoo.com

(Received 28 April 2012; accepted 11 May 2012; online 19 May 2012)

The P atom in the title compound, C₁₆H₁₇Cl₃N₃O₂P, is bonded in a distorted tetrahedral geometry with the phosphoryl and carbonyl groups anti with respect to one another. In the crystal, molecules 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_r = 420.65
Monoclinic, P 2₁ /c
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 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.028
wR(F²) = 0.072
S = 1.04
3265 reflections
240 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.33 e Å⁻³
Δρ_min = −0.26 e Å⁻³

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) $[x, -y+{\script{3\over 2}}, z+{\script{1\over 2}}]$ ; (ii) $[x, -y+{\script{3\over 2}}, z-{\script{1\over 2}}]$ .

Data collection: CrysAlis CCD (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); cell refinement: CrysAlis RED (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis CCD and CrysAlis RED. Oxford Diffraction Ltd, Yarnton, England.]$ ); data reduction: CrysAlis RED; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: Mercury (Macrae et al., 2008 ); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S160053681202154X/lh5469sup1.cif

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

checkCIF report

Comment top

The structure determination of the title compound, P(O)[NHC(O)CCl₃][NHC₆H₄(4-CH₃)]₂ (Fig. 1), was performed as a part of a project on the synthesis of new phosphoric triamides having a C(O)NHP(O) skeleton (Pourayoubi et al., 2011).

The P═O (1.4727 (12) Å) and C═O (1.211 (2) Å) bond lengths are standard for this category of compounds (Pourayoubi et al., 2011). The P atom has a distorted tetrahedral configuration (Fig. 1). The bond angles at the P atom are in the range 102.25 (8) – 118.28 (8)°. The P—N1 and P—N2 bonds (with lengths of 1.6195 (16) Å and 1.6345 (16) Å) are shorter than the P—N3 bond (1.7071 (16) Å). As might be expected the C15—N3 bond distance (1.349 (2) Å) is shorter than the other C—N bond distances.

In the crystal, each molecule is hydrogen-bonded to two adjacent molecules through N_C(O)NHP(O)—H···O(C) and (N—H)₂···O(P) hydrogen bonds along the c axis with the oxygen atom of phosphoryl group as a double-hydrogen bond acceptor (Steiner, 2002; Pourayoubi et al., 2012).

Related literature top

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 top

CCl₃C(O)NHP(O)Cl₂ was synthesized from a reaction between phosphorus pentachloride (15.5 mmol) and 2,2,2-trichloroacetamide (15.5 mmol) in dry CCl₄ at 353 K (3 h) and then treated with formic acid 85% (15.5 mmol) at ice bath temperature.

To a solution of CCl₃C(O)NHP(O)Cl₂ (1.7 mmol) in dry chloroform (30 ml), a solution of p-toluidine (6.8 mmol) in the same solvent (5 ml) was added at ice bath temperature. After 4 h stirring, the solvent was removed and the product was washed with distilled water and recrystallized from methanol at room temperature. IR (KBr, cm^-1): 3305, 3248, 3029, 2920, 2858, 1714, 1619, 1514, 1433, 1376, 1277, 1234, 1191, 963, 882, 811, 730, 683.

Single crystals were obtained from a solution of the title compound in CH₃OH after slow evaporation at room temperature.

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: Mercury (Macrae et al., 2008); software used to prepare material for publication: enCIFer (Allen et al., 2004).

Figures top

	Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level.
	Fig. 2. Partial packing view showing the formation of a chain through N_C(O)NHP(O)—H···O(C) and (N—H)₂···O(P) hydrogen bonds along the c axis. The dashed lines show the donor···acceptor distances of the hydrogen bonds.

N,N'-Bis(4-methylphenyl)-N''-(2,2,2- trichloroacetyl)phosphoric triamide top

Crystal data top

C₁₆H₁₇Cl₃N₃O₂P	F(000) = 864
M_r = 420.65	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3265 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2820 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.013
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scan	h = −20→8
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −12→12
T_min = 0.955, T_max = 1.000	l = −11→11
6796 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)] = 0.028	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(F_o²) + (0.0371P)² + 0.8844P] where P = (F_o² + 2F_c²)/3
3265 reflections	(Δ/σ)_max = 0.001
240 parameters	Δρ_max = 0.33 e Å⁻³
0 restraints	Δρ_min = −0.26 e Å⁻³

Crystal data top

C₁₆H₁₇Cl₃N₃O₂P	V = 1860.12 (11) Å³
M_r = 420.65	Z = 4
Monoclinic, P2₁/c	Mo Kα radiation
a = 17.5151 (6) Å	µ = 0.59 mm⁻¹
b = 10.8638 (4) Å	T = 120 K
c = 9.8615 (3) Å	0.60 × 0.60 × 0.60 mm
β = 97.565 (3)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3265 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2820 reflections with I > 2σ(I)
T_min = 0.955, T_max = 1.000	R_int = 0.013
6796 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.028	0 restraints
wR(F²) = 0.072	H atoms treated by a mixture of independent and constrained refinement
S = 1.04	Δρ_max = 0.33 e Å⁻³
3265 reflections	Δρ_min = −0.26 e Å⁻³
240 parameters

Special details top

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.

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

	x	y	z	U_iso*/U_eq
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)*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Experimental details

Crystal data
Chemical formula	C₁₆H₁₇Cl₃N₃O₂P
M_r	420.65
Crystal system, space group	Monoclinic, P2₁/c
Temperature (K)	120
a, b, c (Å)	17.5151 (6), 10.8638 (4), 9.8615 (3)
β (°)	97.565 (3)
V (Å³)	1860.12 (11)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.59
Crystal size (mm)	0.60 × 0.60 × 0.60

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.955, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6796, 3265, 2820
R_int	0.013
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.028, 0.072, 1.04
No. of reflections	3265
No. of parameters	240
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.33, −0.26

Computer programs: CrysAlis CCD (Oxford Diffraction, 2009), CrysAlis RED (Oxford Diffraction, 2009), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), Mercury (Macrae et al., 2008), enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top

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) x, −y+3/2, z+1/2; (ii) x, −y+3/2, z−1/2.

Acknowledgements

Support of this investigation by the Islamic Azad University, North Tehran Branch, is gratefully acknowledged.

References

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