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

Pourayoubi, M.; Fadaei, H.; Parvez, M.

doi:10.1107/S1600536811027681

organic compounds

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ISSN: 2056-9890

Volume 67| Part 8| August 2011| Page o2046

doi:10.1107/S1600536811027681

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

Mehrdad Pourayoubi,^a ^* Hassan Fadaei ^a and Masood Parvez ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad 91779, Iran, and ^bDepartment of Chemistry, University of Calgary, 2500 University Drive N.W., Calgary, Alberta, Canada T2N 1N4
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 24 June 2011; accepted 11 July 2011; online 16 July 2011)

The P atom in the title compound, C₁₆H₁₅Cl₅N₃O₂P, exhibits a tetrahedral coordination geometry and the phosphoryl and carbonyl groups are anti with respect to one another. The dihedral angle between the benzene rings is 44.90 (15)°. One of the 2-chlorobenzylamido fragments is disordered over two sets of sites with occupancies of 0.8823 (17) and 0.1177 (17). 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 details of compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011 ). For bond lengths in related structures, see: Pourayoubi et al. (2011 ); Rudd et al. (1996 ).

Experimental

Crystal data

C₁₆H₁₅Cl₅N₃O₂P
M_r = 489.53
Triclinic, $[P \overline 1]$
a = 9.9789 (2) Å
b = 10.6058 (3) Å
c = 10.8386 (3) Å
α = 75.8920 (13)°
β = 72.2250 (15)°
γ = 69.6050 (15)°
V = 1011.66 (4) Å³
Z = 2
Mo Kα radiation
μ = 0.81 mm⁻¹
T = 173 K
0.18 × 0.14 × 0.12 mm

Data collection

Nonius KappaCCD diffractometer with APEXII CCD detector
Absorption correction: multi-scan (SORTAV; Blessing, 1997 ) T_min = 0.867, T_max = 0.909
8947 measured reflections
4638 independent reflections
4083 reflections with I > 2σ(I)
R_int = 0.020

Refinement

R[F² > 2σ(F²)] = 0.053
wR(F²) = 0.129
S = 1.05
4638 reflections
245 parameters
H-atom parameters constrained
Δρ_max = 1.42 e Å⁻³
Δρ_min = −0.68 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1⋯O2ⁱ	0.88	1.94	2.804 (3)	168
N2—H2⋯O1ⁱⁱ	0.88	2.38	3.106 (3)	141
N2′—H2′⋯O1	0.88	2.42	3.025 (3)	126
N3—H3⋯O1ⁱⁱ	0.88	2.34	3.129 (3)	149
Symmetry codes: (i) -x+1, -y, -z+2; (ii) -x+2, -y, -z+2.

Data collection: COLLECT (Hooft, 1998 ); cell refinement: DENZO (Otwinowski & Minor, 1997 ); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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: enCIFer (Allen et al., 2004 ).

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536811027681/sj5176sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811027681/sj5176Isup2.hkl

checkCIF report

Comment top

The structure determination of the title compound, P(O)[NHC(O)CCl₃][NHCH₂C₆H₄(2-Cl)]₂ (Fig. 1), was performed as a part of a project in our laboratory on the synthesis of new phosphoramidate compounds having a C(O)NHP(O) skeleton (Toghraee et al., 2011). Single crystals of the title compound were obtained from a solution of CH₃OH after slow evaporation at room temperature.

The P═O (1.472 (2) Å) and C═O (1.212 (3) Å) bond lengths are standard for this category of compounds (Pourayoubi et al., 2011). The P atom has a distorted tetrahedral configuration (Fig. 1) as has been noted for other phosphoric triamides and their chalco-derivatives (Rudd et al., 1996). The bond angles at the P atom vary in the range 103.26 (13)- 116.10 (12)°. The P—N2 and P—N3 bonds (with lengths of 1.621 (2) Å and 1.622 (2) Å) are shorter than the P—N1 bond (1.715 (2) Å). As can be expected the C1—N1 bond distance (1.339 (3) Å) is shorter than the other C—N bond distances. The N—H unit of C(O)NHP(O) moiety and the phosphoryl group have a syn orientation with respect to each other. One of the 2-chlorobenzylamido fragments is disordered over two sites with occupancies of 0.8823 (17) and 0.1177 (17).

In the crystal, each molecule is hydrogen-bonded to two adjacent molecules through N_C(O)NHP(O)—H···O(P) and N—H···O(C) hydrogen bonds forming linear chains parallel to [100] (Table 1).

Related literature top

For details of compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011). For bond lengths in related structures, see: Pourayoubi et al. (2011); Rudd et al. (1996).

Experimental top

The reaction of phosphorus pentachloride (35.6 mmol) and 2,2,2-trichloroacetamide (35.6 mmol) in dry CCl₄ (25 ml) at 353 K (3 h) and then treatment with formic acid 85% (35.6 mmol) at 271 K leads to the formation of CCl₃C(O)NHP(O)Cl₂ as a white solid.

To a solution of CCl₃C(O)NHP(O)Cl₂ (2.5 mmol) in dry CHCl₃ (30 ml), a solution of 2-chlorobenzylamine (10 mmol) in dry CHCl₃ (10 ml) was added dropwise at 271 K. After 4 h stirring, the solvent was evaporated at room temperature. The solid was washed with distilled water and recrystallized from CH₃OH.

Computing details top

Data collection: COLLECT (Hooft, 1998); cell refinement: DENZO (Otwinowski & Minor, 1997); data reduction: SCALEPACK (Otwinowski & Minor, 1997); 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: enCIFer (Allen et al., 2004).

Figures top

Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level. The minor disorder component is not shown.

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

Crystal data top

C₁₆H₁₅Cl₅N₃O₂P	Z = 2
M_r = 489.53	F(000) = 496
Triclinic, P1	D_x = 1.607 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.9789 (2) Å	Cell parameters from 4567 reflections
b = 10.6058 (3) Å	θ = 1.0–27.5°
c = 10.8386 (3) Å	µ = 0.81 mm⁻¹
α = 75.8920 (13)°	T = 173 K
β = 72.2250 (15)°	Prism, colorless
γ = 69.6050 (15)°	0.18 × 0.14 × 0.12 mm
V = 1011.66 (4) Å³

Data collection top

Nonius KappaCCD diffractometer with APEXII CCD detector	4638 independent reflections
Radiation source: fine-focus sealed tube	4083 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.020
ω and ϕ scans	θ_max = 27.6°, θ_min = 2.0°
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	h = −12→12
T_min = 0.867, T_max = 0.909	k = −13→13
8947 measured reflections	l = −14→14

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)] = 0.053	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.043P)² + 2.0234P] where P = (F_o² + 2F_c²)/3
4638 reflections	(Δ/σ)_max < 0.001
245 parameters	Δρ_max = 1.42 e Å⁻³
0 restraints	Δρ_min = −0.68 e Å⁻³

Crystal data top

C₁₆H₁₅Cl₅N₃O₂P	γ = 69.6050 (15)°
M_r = 489.53	V = 1011.66 (4) Å³
Triclinic, P1	Z = 2
a = 9.9789 (2) Å	Mo Kα radiation
b = 10.6058 (3) Å	µ = 0.81 mm⁻¹
c = 10.8386 (3) Å	T = 173 K
α = 75.8920 (13)°	0.18 × 0.14 × 0.12 mm
β = 72.2250 (15)°

Data collection top

Nonius KappaCCD diffractometer with APEXII CCD detector	4638 independent reflections
Absorption correction: multi-scan (SORTAV; Blessing, 1997)	4083 reflections with I > 2σ(I)
T_min = 0.867, T_max = 0.909	R_int = 0.020
8947 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.053	0 restraints
wR(F²) = 0.129	H-atom parameters constrained
S = 1.05	Δρ_max = 1.42 e Å⁻³
4638 reflections	Δρ_min = −0.68 e Å⁻³
245 parameters

Special details top

Experimental. IR (KBr, cm^-1): 3371, 3061, 2875, 1692, 1448, 1257, 1224, 1076, 1043, 885, 837, 751, 675.

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	Occ. (<1)
Cl1	0.58102 (9)	−0.04802 (11)	1.36183 (8)	0.0547 (3)
Cl2	0.87488 (8)	−0.22348 (7)	1.35952 (8)	0.03998 (19)
Cl3	0.68228 (12)	−0.30242 (9)	1.26210 (11)	0.0590 (3)
P1	0.72798 (7)	0.04068 (7)	0.90391 (6)	0.02507 (16)
O1	0.9079 (2)	−0.0722 (2)	1.1030 (2)	0.0386 (5)
O2	0.60042 (19)	0.0572 (2)	0.85370 (18)	0.0317 (4)
N1	0.6903 (2)	−0.0446 (2)	1.0605 (2)	0.0262 (4)
H1	0.6044	−0.0605	1.0925	0.031*
C1	0.7866 (3)	−0.0882 (3)	1.1360 (3)	0.0259 (5)
C2	0.7338 (3)	−0.1636 (3)	1.2751 (3)	0.0301 (5)
N2	0.8865 (2)	−0.0463 (3)	0.8250 (2)	0.0352 (6)
H2	0.9630	−0.0151	0.8031	0.042*	0.8823 (17)
C3	0.9024 (3)	−0.1740 (3)	0.7909 (3)	0.0335 (7)	0.8823 (17)
H3A	0.8074	−0.1713	0.7779	0.040*	0.8823 (17)
H3B	0.9247	−0.2470	0.8649	0.040*	0.8823 (17)
C4	1.0236 (2)	−0.2094 (2)	0.66667 (18)	0.0269 (7)	0.8823 (17)
C5	1.0496 (2)	−0.3322 (2)	0.6261 (2)	0.0362 (7)	0.8823 (17)
C6	1.1578 (3)	−0.3675 (2)	0.5135 (2)	0.0476 (10)	0.8823 (17)
H6	1.1755	−0.4515	0.4858	0.057*	0.8823 (17)
C7	1.2401 (3)	−0.2800 (3)	0.4415 (2)	0.0501 (11)	0.8823 (17)
H7	1.3141	−0.3041	0.3645	0.060*	0.8823 (17)
C8	1.2141 (2)	−0.1572 (2)	0.4820 (2)	0.0467 (9)	0.8823 (17)
H8	1.2704	−0.0973	0.4328	0.056*	0.8823 (17)
C9	1.1059 (2)	−0.12185 (18)	0.5946 (2)	0.0342 (7)	0.8823 (17)
H9	1.0882	−0.0379	0.6223	0.041*	0.8823 (17)
Cl4	0.94994 (12)	−0.44175 (10)	0.71412 (13)	0.0605 (3)	0.8823 (17)
H2'	0.9162	−0.1096	0.8886	0.042*	0.1177 (17)
C3'	0.993 (3)	−0.079 (2)	0.730 (2)	0.0335 (7)	0.1177 (17)
H3'1	1.0801	−0.0997	0.7645	0.040*	0.1177 (17)
H3'2	0.9892	0.0079	0.6686	0.040*	0.1177 (17)
C4'	1.036 (2)	−0.1806 (18)	0.6432 (18)	0.0269 (7)	0.1177 (17)
C5'	1.148 (2)	−0.1813 (19)	0.529 (2)	0.0362 (7)	0.1177 (17)
C6'	1.199 (2)	−0.289 (2)	0.4586 (18)	0.0476 (10)	0.1177 (17)
H6'	1.2753	−0.2892	0.3808	0.057*	0.1177 (17)
C7'	1.137 (2)	−0.395 (2)	0.501 (2)	0.0501 (11)	0.1177 (17)
H7'	1.1711	−0.4687	0.4529	0.060*	0.1177 (17)
C8'	1.024 (2)	−0.3946 (17)	0.6152 (19)	0.0467 (9)	0.1177 (17)
H8'	0.9819	−0.4675	0.6445	0.056*	0.1177 (17)
C9'	0.9738 (19)	−0.287 (2)	0.6861 (15)	0.0342 (7)	0.1177 (17)
H9'	0.8970	−0.2867	0.7638	0.041*	0.1177 (17)
Cl4'	1.2278 (9)	−0.0556 (8)	0.4817 (10)	0.0605 (3)	0.1177 (17)
N3	0.7555 (2)	0.1823 (2)	0.9050 (2)	0.0309 (5)
H3	0.8465	0.1849	0.8889	0.037*
C10	0.6334 (3)	0.3062 (3)	0.9322 (3)	0.0356 (6)
H10A	0.5478	0.3027	0.9065	0.043*
H10B	0.6632	0.3860	0.8773	0.043*
C11	0.5868 (3)	0.3256 (3)	1.0740 (3)	0.0322 (6)
C12	0.6657 (4)	0.3724 (3)	1.1291 (3)	0.0409 (7)
C13	0.6224 (5)	0.3866 (4)	1.2614 (4)	0.0529 (9)
H13	0.6780	0.4188	1.2971	0.064*
C14	0.4988 (5)	0.3535 (4)	1.3393 (4)	0.0584 (10)
H14	0.4689	0.3624	1.4296	0.070*
C15	0.4189 (4)	0.3081 (4)	1.2880 (4)	0.0559 (9)
H15	0.3331	0.2856	1.3424	0.067*
C16	0.4620 (4)	0.2945 (3)	1.1571 (3)	0.0437 (7)
H16	0.4047	0.2629	1.1228	0.052*
Cl5	0.82320 (12)	0.41376 (12)	1.03083 (12)	0.0672 (3)

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0395 (4)	0.0749 (6)	0.0293 (4)	0.0045 (4)	−0.0024 (3)	−0.0105 (4)
Cl2	0.0424 (4)	0.0350 (4)	0.0463 (4)	−0.0098 (3)	−0.0260 (3)	0.0039 (3)
Cl3	0.0763 (6)	0.0416 (5)	0.0793 (7)	−0.0360 (4)	−0.0472 (5)	0.0180 (4)
P1	0.0178 (3)	0.0380 (4)	0.0204 (3)	−0.0100 (3)	−0.0013 (2)	−0.0080 (3)
O1	0.0246 (10)	0.0590 (14)	0.0358 (11)	−0.0193 (9)	−0.0083 (8)	−0.0023 (10)
O2	0.0199 (9)	0.0517 (12)	0.0251 (9)	−0.0139 (8)	−0.0036 (7)	−0.0063 (8)
N1	0.0195 (10)	0.0363 (12)	0.0235 (10)	−0.0118 (9)	−0.0025 (8)	−0.0042 (9)
C1	0.0224 (12)	0.0282 (13)	0.0269 (13)	−0.0077 (10)	−0.0050 (10)	−0.0049 (10)
C2	0.0302 (13)	0.0271 (13)	0.0333 (14)	−0.0094 (10)	−0.0119 (11)	0.0013 (10)
N2	0.0201 (10)	0.0533 (15)	0.0354 (13)	−0.0106 (10)	0.0012 (9)	−0.0232 (11)
C3	0.0285 (15)	0.0314 (16)	0.0339 (16)	−0.0083 (12)	0.0032 (12)	−0.0078 (13)
C4	0.0245 (13)	0.0277 (16)	0.0247 (15)	−0.0021 (12)	−0.0062 (11)	−0.0053 (12)
C5	0.0303 (16)	0.0358 (17)	0.0444 (19)	−0.0038 (13)	−0.0142 (14)	−0.0117 (14)
C6	0.039 (2)	0.052 (2)	0.050 (2)	0.0103 (17)	−0.0210 (17)	−0.0285 (19)
C7	0.040 (2)	0.068 (3)	0.0244 (17)	0.0100 (19)	−0.0069 (15)	−0.0146 (17)
C8	0.0312 (17)	0.061 (2)	0.0269 (17)	0.0004 (16)	−0.0008 (14)	0.0019 (16)
C9	0.0285 (15)	0.0358 (17)	0.0307 (16)	−0.0046 (13)	−0.0026 (12)	−0.0050 (13)
Cl4	0.0475 (5)	0.0380 (5)	0.0988 (9)	−0.0148 (4)	−0.0086 (5)	−0.0240 (5)
N2'	0.0201 (10)	0.0533 (15)	0.0354 (13)	−0.0106 (10)	0.0012 (9)	−0.0232 (11)
C3'	0.0285 (15)	0.0314 (16)	0.0339 (16)	−0.0083 (12)	0.0032 (12)	−0.0078 (13)
C4'	0.0245 (13)	0.0277 (16)	0.0247 (15)	−0.0021 (12)	−0.0062 (11)	−0.0053 (12)
C5'	0.0303 (16)	0.0358 (17)	0.0444 (19)	−0.0038 (13)	−0.0142 (14)	−0.0117 (14)
C6'	0.039 (2)	0.052 (2)	0.050 (2)	0.0103 (17)	−0.0210 (17)	−0.0285 (19)
C7'	0.040 (2)	0.068 (3)	0.0244 (17)	0.0100 (19)	−0.0069 (15)	−0.0146 (17)
C8'	0.0312 (17)	0.061 (2)	0.0269 (17)	0.0004 (16)	−0.0008 (14)	0.0019 (16)
C9'	0.0285 (15)	0.0358 (17)	0.0307 (16)	−0.0046 (13)	−0.0026 (12)	−0.0050 (13)
Cl4'	0.0475 (5)	0.0380 (5)	0.0988 (9)	−0.0148 (4)	−0.0086 (5)	−0.0240 (5)
N3	0.0251 (11)	0.0398 (13)	0.0293 (12)	−0.0138 (10)	−0.0051 (9)	−0.0035 (10)
C10	0.0399 (15)	0.0336 (15)	0.0342 (15)	−0.0088 (12)	−0.0169 (12)	0.0002 (11)
C11	0.0369 (14)	0.0232 (13)	0.0353 (15)	−0.0020 (11)	−0.0174 (12)	−0.0017 (11)
C12	0.0452 (17)	0.0320 (15)	0.0484 (18)	−0.0072 (13)	−0.0219 (14)	−0.0041 (13)
C13	0.073 (3)	0.0379 (18)	0.054 (2)	0.0001 (16)	−0.038 (2)	−0.0127 (15)
C14	0.063 (2)	0.050 (2)	0.0396 (19)	0.0104 (18)	−0.0097 (17)	−0.0114 (16)
C15	0.048 (2)	0.053 (2)	0.048 (2)	−0.0016 (16)	−0.0025 (16)	−0.0043 (17)
C16	0.0402 (17)	0.0381 (17)	0.0478 (19)	−0.0070 (13)	−0.0101 (14)	−0.0053 (14)
Cl5	0.0632 (6)	0.0785 (7)	0.0774 (7)	−0.0424 (5)	−0.0238 (5)	−0.0030 (5)

Geometric parameters (Å, º) top

Cl1—C2	1.759 (3)	C3'—H3'2	0.9900
Cl2—C2	1.761 (3)	C4'—C5'	1.3900
Cl3—C2	1.768 (3)	C4'—C9'	1.3900
P1—O2	1.4724 (18)	C5'—C6'	1.3900
P1—N2	1.621 (2)	C5'—Cl4'	1.682 (17)
P1—N3	1.622 (2)	C6'—C7'	1.3900
P1—N1	1.715 (2)	C6'—H6'	0.9500
O1—C1	1.212 (3)	C7'—C8'	1.3900
N1—C1	1.339 (3)	C7'—H7'	0.9500
N1—H1	0.8800	C8'—C9'	1.3900
C1—C2	1.553 (4)	C8'—H8'	0.9500
N2—C3	1.434 (4)	C9'—H9'	0.9500
N2—H2	0.8800	N3—C10	1.467 (4)
C3—C4	1.534 (3)	N3—H3	0.8800
C3—H3A	0.9900	C10—C11	1.507 (4)
C3—H3B	0.9900	C10—H10A	0.9900
C4—C5	1.3900	C10—H10B	0.9900
C4—C9	1.3900	C11—C12	1.388 (4)
C5—C6	1.3900	C11—C16	1.389 (4)
C5—Cl4	1.713 (2)	C12—C13	1.395 (5)
C6—C7	1.3900	C12—Cl5	1.740 (4)
C6—H6	0.9500	C13—C14	1.371 (6)
C7—C8	1.3900	C13—H13	0.9500
C7—H7	0.9500	C14—C15	1.359 (6)
C8—C9	1.3900	C14—H14	0.9500
C8—H8	0.9500	C15—C16	1.380 (5)
C9—H9	0.9500	C15—H15	0.9500
C3'—C4'	1.47 (3)	C16—H16	0.9500
C3'—H3'1	0.9900

O2—P1—N2	116.10 (12)	H3'1—C3'—H3'2	105.4
O2—P1—N3	114.51 (12)	C5'—C4'—C9'	120.0
N2—P1—N3	103.26 (13)	C5'—C4'—C3'	121.6 (16)
O2—P1—N1	104.46 (11)	C9'—C4'—C3'	118.0 (16)
N2—P1—N1	108.13 (13)	C4'—C5'—C6'	120.0
N3—P1—N1	110.31 (11)	C4'—C5'—Cl4'	119.8 (12)
C1—N1—P1	122.56 (18)	C6'—C5'—Cl4'	120.1 (12)
C1—N1—H1	118.7	C5'—C6'—C7'	120.0
P1—N1—H1	118.7	C5'—C6'—H6'	120.0
O1—C1—N1	124.8 (2)	C7'—C6'—H6'	120.0
O1—C1—C2	119.8 (2)	C8'—C7'—C6'	120.0
N1—C1—C2	115.5 (2)	C8'—C7'—H7'	120.0
C1—C2—Cl1	108.21 (18)	C6'—C7'—H7'	120.0
C1—C2—Cl2	110.50 (18)	C7'—C8'—C9'	120.0
Cl1—C2—Cl2	109.24 (16)	C7'—C8'—H8'	120.0
C1—C2—Cl3	109.63 (19)	C9'—C8'—H8'	120.0
Cl1—C2—Cl3	109.77 (15)	C8'—C9'—C4'	120.0
Cl2—C2—Cl3	109.47 (15)	C8'—C9'—H9'	120.0
C3—N2—P1	120.0 (2)	C4'—C9'—H9'	120.0
C3—N2—H2	120.0	C10—N3—P1	122.06 (19)
P1—N2—H2	120.0	C10—N3—H3	119.0
N2—C3—C4	113.7 (2)	P1—N3—H3	119.0
N2—C3—H3A	108.8	N3—C10—C11	113.5 (2)
C4—C3—H3A	108.8	N3—C10—H10A	108.9
N2—C3—H3B	108.8	C11—C10—H10A	108.9
C4—C3—H3B	108.8	N3—C10—H10B	108.9
H3A—C3—H3B	107.7	C11—C10—H10B	108.9
C5—C4—C9	120.0	H10A—C10—H10B	107.7
C5—C4—C3	118.28 (18)	C12—C11—C16	116.5 (3)
C9—C4—C3	121.71 (18)	C12—C11—C10	122.8 (3)
C4—C5—C6	120.0	C16—C11—C10	120.7 (3)
C4—C5—Cl4	120.65 (14)	C11—C12—C13	121.7 (3)
C6—C5—Cl4	119.35 (14)	C11—C12—Cl5	119.1 (3)
C7—C6—C5	120.0	C13—C12—Cl5	119.1 (3)
C7—C6—H6	120.0	C14—C13—C12	119.3 (3)
C5—C6—H6	120.0	C14—C13—H13	120.3
C6—C7—C8	120.0	C12—C13—H13	120.3
C6—C7—H7	120.0	C15—C14—C13	120.3 (4)
C8—C7—H7	120.0	C15—C14—H14	119.9
C9—C8—C7	120.0	C13—C14—H14	119.9
C9—C8—H8	120.0	C14—C15—C16	120.1 (4)
C7—C8—H8	120.0	C14—C15—H15	119.9
C8—C9—C4	120.0	C16—C15—H15	119.9
C8—C9—H9	120.0	C15—C16—C11	121.9 (3)
C4—C9—H9	120.0	C15—C16—H16	119.0
C4'—C3'—H3'1	103.9	C11—C16—H16	119.0
C4'—C3'—H3'2	103.9

O2—P1—N1—C1	174.8 (2)	C9'—C4'—C5'—C6'	0.0
N2—P1—N1—C1	50.6 (2)	C3'—C4'—C5'—C6'	172 (2)
N3—P1—N1—C1	−61.6 (2)	C9'—C4'—C5'—Cl4'	−177.3 (15)
P1—N1—C1—O1	0.2 (4)	C3'—C4'—C5'—Cl4'	−5 (2)
P1—N1—C1—C2	−179.98 (18)	C4'—C5'—C6'—C7'	0.0
O1—C1—C2—Cl1	116.0 (3)	Cl4'—C5'—C6'—C7'	177.2 (16)
N1—C1—C2—Cl1	−63.9 (3)	C5'—C6'—C7'—C8'	0.0
O1—C1—C2—Cl2	−3.6 (3)	C6'—C7'—C8'—C9'	0.0
N1—C1—C2—Cl2	176.56 (19)	C7'—C8'—C9'—C4'	0.0
O1—C1—C2—Cl3	−124.3 (2)	C5'—C4'—C9'—C8'	0.0
N1—C1—C2—Cl3	55.8 (3)	C3'—C4'—C9'—C8'	−172 (2)
O2—P1—N2—C3	−47.0 (3)	O2—P1—N3—C10	34.9 (2)
N3—P1—N2—C3	−173.2 (2)	N2—P1—N3—C10	162.0 (2)
N1—P1—N2—C3	69.9 (3)	N1—P1—N3—C10	−82.6 (2)
P1—N2—C3—C4	151.5 (2)	P1—N3—C10—C11	94.5 (3)
N2—C3—C4—C5	179.0 (2)	N3—C10—C11—C12	77.3 (3)
N2—C3—C4—C9	−1.5 (4)	N3—C10—C11—C16	−101.5 (3)
C9—C4—C5—C6	0.0	C16—C11—C12—C13	0.4 (4)
C3—C4—C5—C6	179.5 (2)	C10—C11—C12—C13	−178.5 (3)
C9—C4—C5—Cl4	179.67 (18)	C16—C11—C12—Cl5	−179.9 (2)
C3—C4—C5—Cl4	−0.8 (2)	C10—C11—C12—Cl5	1.2 (4)
C4—C5—C6—C7	0.0	C11—C12—C13—C14	0.0 (5)
Cl4—C5—C6—C7	−179.67 (18)	Cl5—C12—C13—C14	−179.7 (3)
C5—C6—C7—C8	0.0	C12—C13—C14—C15	−0.3 (5)
C6—C7—C8—C9	0.0	C13—C14—C15—C16	0.2 (6)
C7—C8—C9—C4	0.0	C14—C15—C16—C11	0.2 (5)
C5—C4—C9—C8	0.0	C12—C11—C16—C15	−0.5 (5)
C3—C4—C9—C8	−179.5 (3)	C10—C11—C16—C15	178.4 (3)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1···O2ⁱ	0.88	1.94	2.804 (3)	168
N2—H2···O1ⁱⁱ	0.88	2.38	3.106 (3)	141
N2′—H2′···O1	0.88	2.42	3.025 (3)	126
N3—H3···O1ⁱⁱ	0.88	2.34	3.129 (3)	149

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

Experimental details

Crystal data
Chemical formula	C₁₆H₁₅Cl₅N₃O₂P
M_r	489.53
Crystal system, space group	Triclinic, P1
Temperature (K)	173
a, b, c (Å)	9.9789 (2), 10.6058 (3), 10.8386 (3)
α, β, γ (°)	75.8920 (13), 72.2250 (15), 69.6050 (15)
V (Å³)	1011.66 (4)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.81
Crystal size (mm)	0.18 × 0.14 × 0.12

Data collection
Diffractometer	Nonius KappaCCD diffractometer with APEXII CCD detector
Absorption correction	Multi-scan (SORTAV; Blessing, 1997)
T_min, T_max	0.867, 0.909
No. of measured, independent and observed [I > 2σ(I)] reflections	8947, 4638, 4083
R_int	0.020
(sin θ/λ)_max (Å⁻¹)	0.652

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.053, 0.129, 1.05
No. of reflections	4638
No. of parameters	245
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	1.42, −0.68

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), 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—H1···O2ⁱ	0.88	1.94	2.804 (3)	168.2
N2—H2···O1ⁱⁱ	0.88	2.38	3.106 (3)	140.5
N2'—H2'···O1	0.88	2.42	3.025 (3)	125.9
N3—H3···O1ⁱⁱ	0.88	2.34	3.129 (3)	149.1

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

Acknowledgements

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

References

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