N,N′-Bis(2-chloro­benz­yl)-N′′-(dichloro­acet­yl)phospho­ric triamide

Pourayoubi, M.; Toghraee, M.; Divjakovic, V.

doi:10.1107/S1600536811000845

organic compounds

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ISSN: 2056-9890

Volume 67| Part 2| February 2011| Page o333

doi:10.1107/S1600536811000845

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N,N′-Bis(2-chlorobenzyl)-N′′-(dichloroacetyl)phosphoric triamide

Mehrdad Pourayoubi,^a ^* Maryam Toghraee ^a and Vladimir Divjakovic ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Physics, Faculty of Sciences, University of Novi Sad, 21000, Serbia
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 9 December 2010; accepted 6 January 2011; online 12 January 2011)

In the title compound, C₁₆H₁₆Cl₄N₃O₂P, 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 molecules 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. (2010a ,b ).

Experimental

Crystal data

C₁₆H₁₆Cl₄N₃O₂P
M_r = 455.09
Triclinic, $[P \overline 1]$
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 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ) 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[F² > 2σ(F²)] = 0.061
wR(F²) = 0.156
S = 1.02
3510 reflections
235 parameters
H-atom parameters constrained
Δρ_max = 0.96 e Å⁻³
Δρ_min = −0.65 e Å⁻³

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

Data collection: CrysAlis PRO (Oxford Diffraction, 2009 $[Oxford Diffraction (2009). CrysAlis PRO. Oxford Diffraction Ltd, Yarnton, England.]$ ); 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 ).

Supporting information

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

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

checkCIF report

Comment top

Organophosphorus compounds are well-known as the biologically active substances (Ekstrom et al., 2006). Among them the anticancer activity of compounds having a C(O)NHP(O) skeleton has been studied (Gholivand et al., 2011). In the previous works, some phosphoric triamides such as P(O)[NHC(O)C₆H₄(4-NO₂)][NHC₆H₁₁]₂ (Sabbaghi et al., 2010a) and P(O)[NHC(O)C₆H₄(4-NO₂)][N(CH₃)(C₆H₁₁)]₂ (Sabbaghi et al., 2010b) have been structurally investigated. We report here on the synthesis and crystal structure of P(O)[NHC(O)CHCl₂][NHCH₂(2-Cl—C₆H₄)]₂. Single crystals of title compound were obtained from a solution of CH₃OH and CH₃CN after a slow evaporation at room temperature. The phosphoryl and carbonyl groups are anti to each other and the phosphorus atom is in a slightly distorted tetrahedral environment (Fig. 1). The bond angles are in the range of 103.08 (16)°-117.84 (17)° around the P atom. The P—N1 and P—N3 (1.616 (3) Å and 1.619 (3) Å) bond lengths are shorter than the P—N2 bond (1.682 (3) Å). The environment of nitrogen atoms is essentially planar. The P═O bond length of 1.471 (3) Å is standard for phosphoramidate compounds.

In the crystal structure, adjacent molecules are linked via N–H···O═P and N–H···O═C hydrogen bonds, into an extended chain parallel to the a axis.

Related literature top

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. (2010a,b).

Experimental top

The reaction of phosphorus pentachloride (16.91 mmol) and CHCl₂C(O)NH₂ (16.91 mmol) in dry CCl₄ at 358 K (3 h) and then the treatment of formic acid (16.91 mmol) at ice bath temperature leads to CHCl₂C(O)NHP(O)Cl₂.

To a solution of CHCl₂C(O)NHP(O)Cl₂ (1.04 mmol) in dry CHCl₃, a solution of 2-chlorobenzylamine (4.16 mmol) in dry CHCl₃ was added dropwise and stirred at 273 K. After 4 h, the solvent was evaporated at room temperature. The solid was washed with H₂O. The product was obtained after recrystallization from a methanol/acetonitrile mixture (4:1) after a slow evaporation at room temperature. IR (KBr, cm^-1): 3392 (NH), 3080 (NH), 2881, 1704 (C═O), 1465, 1203 (P═O), 1072, 887.

Computing details top

Data collection: CrysAlis PRO (Oxford Diffraction, 2009); cell refinement: CrysAlis PRO (Oxford Diffraction, 2009); data reduction: CrysAlis PRO (Oxford Diffraction, 2009); 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 (Sheldrick, 2008) and PLATON (Spek, 2009).

Figures top

Fig. 1. An ORTEP style plot of title compound. Ellipsoids are given at 30% probability level.

N,N'-Bis(2-chlorobenzyl)-N''-(dichloroacetyl)phosphoric triamide top

Crystal data top

C₁₆H₁₆Cl₄N₃O₂P	Z = 2
M_r = 455.09	F(000) = 464
Triclinic, P1	D_x = 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

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3510 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2786 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.018
Detector resolution: 16.3280 pixels mm^-1	θ_max = 25.0°, θ_min = 3.5°
ω scans	h = −11→9
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	k = −11→12
T_min = 0.978, T_max = 1.000	l = −14→13
6193 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)] = 0.061	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.156	H-atom parameters constrained
S = 1.02	w = 1/[σ²(F_o²) + (0.0618P)² + 1.5174P] where P = (F_o² + 2F_c²)/3
3510 reflections	(Δ/σ)_max < 0.001
235 parameters	Δρ_max = 0.96 e Å⁻³
0 restraints	Δρ_min = −0.65 e Å⁻³

Crystal data top

C₁₆H₁₆Cl₄N₃O₂P	γ = 114.084 (6)°
M_r = 455.09	V = 998.7 (2) Å³
Triclinic, P1	Z = 2
a = 9.901 (1) Å	Mo Kα radiation
b = 10.179 (1) Å	µ = 0.69 mm⁻¹
c = 12.013 (2) Å	T = 295 K
α = 90.403 (5)°	0.22 × 0.12 × 0.11 mm
β = 112.851 (6)°

Data collection top

Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer	3510 independent reflections
Absorption correction: multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)	2786 reflections with I > 2σ(I)
T_min = 0.978, T_max = 1.000	R_int = 0.018
6193 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.061	0 restraints
wR(F²) = 0.156	H-atom parameters constrained
S = 1.02	Δρ_max = 0.96 e Å⁻³
3510 reflections	Δρ_min = −0.65 e Å⁻³
235 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
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*

Atomic displacement parameters (Å²) top

	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)

Geometric parameters (Å, º) top

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)

Hydrogen-bond geometry (Å, º) top

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₆Cl₄N₃O₂P
M_r	455.09
Crystal system, space group	Triclinic, P1
Temperature (K)	295
a, b, c (Å)	9.901 (1), 10.179 (1), 12.013 (2)
α, β, γ (°)	90.403 (5), 112.851 (6), 114.084 (6)
V (Å³)	998.7 (2)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.69
Crystal size (mm)	0.22 × 0.12 × 0.11

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire3 Gemini diffractometer
Absorption correction	Multi-scan (CrysAlis PRO; Oxford Diffraction, 2009)
T_min, T_max	0.978, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	6193, 3510, 2786
R_int	0.018
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.061, 0.156, 1.02
No. of reflections	3510
No. of parameters	235
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.96, −0.65

Computer programs: CrysAlis PRO (Oxford Diffraction, 2009), SIR92 (Altomare et al., 1993), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009).

Hydrogen-bond geometry (Å, º) top

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

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged.

References

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