N,N′-Dibenzyl-N′′-(2-chloro­acet­yl)-N,N′-dimethyl­phospho­ric triamide

Pourayoubi, M.; Keikha, M.; Nečas, M.

doi:10.1107/S1600536811033204

organic compounds

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ISSN: 2056-9890

Volume 67| Part 9| September 2011| Page o2439

doi:10.1107/S1600536811033204

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N,N′-Dibenzyl-N′′-(2-chloroacetyl)-N,N′-dimethylphosphoric triamide

Mehrdad Pourayoubi,^a ^* Mojtaba Keikha ^a and Marek Nečas ^b

^aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and ^bDepartment of Chemistry, Faculty of Science, Masaryk University, Kotlarska 2, Brno CZ-61137, Czech Republic
^*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 2 August 2011; accepted 16 August 2011; online 27 August 2011)

In the title molecule, C₁₈H₂₃ClN₃O₂P, the P atom is bonded in a distorted tetrahedral environment. The P=O and N—H groups are syn with respect to each other. The angles at the tertiary N atoms confirm their sp² character. In the crystal, pairs of intermolecular P=O⋯H—N hydrogen bonds form centrosymmetric dimers.

Related literature

For background to compounds having a C(=O)NHP(=O) skeleton, see: Toghraee et al. (2011 ); Pourayoubi et al. (2011 ).

Experimental

Crystal data

C₁₈H₂₃ClN₃O₂P
M_r = 379.81
Triclinic, $[P \overline 1]$
a = 9.5891 (8) Å
b = 9.9259 (7) Å
c = 10.2543 (8) Å
α = 89.509 (6)°
β = 74.945 (7)°
γ = 79.921 (6)°
V = 927.27 (12) Å³
Z = 2
Mo Kα radiation
μ = 0.31 mm⁻¹
T = 120 K
0.40 × 0.40 × 0.20 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 = 0.983, T_max = 1.000
5838 measured reflections
3253 independent reflections
2594 reflections with I > 2σ(I)
R_int = 0.016

Refinement

R[F² > 2σ(F²)] = 0.031
wR(F²) = 0.083
S = 1.06
3253 reflections
232 parameters
H atoms treated by a mixture of independent and constrained refinement
Δρ_max = 0.25 e Å⁻³
Δρ_min = −0.37 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
N1—H1N⋯O1ⁱ	0.773 (18)	2.037 (19)	2.795 (2)	167.1 (19)
Symmetry code: (i) -x+1, -y+1, -z+1.

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/S1600536811033204/lh5303sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536811033204/lh5303Isup2.hkl

checkCIF report

Comment top

The structure determination of the title compound was performed as part of a project in our laboratory on the synthesis of new phosphoramidates with formula RC(O)NHP(O)[NR'R"]₂ (Toghraee et al., 2011). The molecular structure of the title compound is shown in Fig. 1. The P1—N2 and P1—N3 bonds are shorter than the P1—N1 bond. The sp² character of the tertiary N atoms is indicated by the angles around N2 and N3. The C1—N1—P1 angle is the most distorted from the expected 120° (in terms of sp² hybridization). The P═O bond length is standard for this type of phosphoramidate compounds (Pourayoubi et al., 2011). The hydrogen atom of the C(═O)NHP(═O) group is involved in an intermolecular –P═O···H—N– hydrogen bond (Table 1). Pair of this type of hydrogen bond forms centrosymmetric dimer which is the usual H-bond pattern for compounds with the general formula RC(O)NHP(O)[NR'R"]₂, where R' and R" ≠ H, in the case of syn orientation of P═O versus N—H (Toghraee et al., 2011).

Related literature top

For background to compounds having a C(═O)NHP(═O) skeleton, see: Toghraee et al. (2011); Pourayoubi et al. (2011).

Experimental top

Synthesis of CH₂ClC(O)NHP(O)Cl₂: The reaction of phosphorus pentachloride (20 mmol) and 2-chloroacetamide (20 mmol) in dry benzene (40 ml) at 353 K (3 h) and then the treatment of formic acid 85% (20 mmol) at room temperature leads to the formation of CH₂ClC(O)NHP(O)Cl₂ as solid product.

Synthesis of title compound: To a solution of (3.47 mmol) CH₂ClC(O)NHP(O)Cl₂ in CHCl₃ (25 ml), a solution of N-methylbenzylamine (13.88 mmol) in CHCl₃ (5 ml) was added dropwise at 273 K. After 6 h of stirring, the solvent was evaporated in vacuum. The solid was washed with distilled water. Single crystals were obtained from a solution of the title compound in chloroform and n-heptane after slow evaporation at room temperature. IR (KBr, cm^-1): 3116, 2920, 1728, 1494, 1341, 1193, 1011, 949, 867, 800, 743, 695.

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.

N,N'-Dibenzyl-N''-(2-chloroacetyl)-N,N'- dimethylphosphoric triamide top

Crystal data top

C₁₈H₂₃ClN₃O₂P	Z = 2
M_r = 379.81	F(000) = 400
Triclinic, P1	D_x = 1.360 Mg m⁻³
Hall symbol: -P 1	Mo Kα radiation, λ = 0.71073 Å
a = 9.5891 (8) Å	Cell parameters from 3547 reflections
b = 9.9259 (7) Å	θ = 3.1–27.6°
c = 10.2543 (8) Å	µ = 0.31 mm⁻¹
α = 89.509 (6)°	T = 120 K
β = 74.945 (7)°	Plate, colorless
γ = 79.921 (6)°	0.40 × 0.40 × 0.20 mm
V = 927.27 (12) Å³

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3253 independent reflections
Radiation source: Enhance (Mo) X-ray Source	2594 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.016
Detector resolution: 8.4353 pixels mm^-1	θ_max = 25.0°, θ_min = 3.1°
ω scans	h = −11→11
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	k = −11→10
T_min = 0.983, T_max = 1.000	l = −12→11
5838 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)] = 0.031	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	w = 1/[σ²(F_o²) + (0.0449P)² + 0.0312P] where P = (F_o² + 2F_c²)/3
3253 reflections	(Δ/σ)_max < 0.001
232 parameters	Δρ_max = 0.25 e Å⁻³
0 restraints	Δρ_min = −0.37 e Å⁻³

Crystal data top

C₁₈H₂₃ClN₃O₂P	γ = 79.921 (6)°
M_r = 379.81	V = 927.27 (12) Å³
Triclinic, P1	Z = 2
a = 9.5891 (8) Å	Mo Kα radiation
b = 9.9259 (7) Å	µ = 0.31 mm⁻¹
c = 10.2543 (8) Å	T = 120 K
α = 89.509 (6)°	0.40 × 0.40 × 0.20 mm
β = 74.945 (7)°

Data collection top

Oxford Diffraction Xcalibur Sapphire2 diffractometer	3253 independent reflections
Absorption correction: multi-scan (CrysAlis RED; Oxford Diffraction, 2009)	2594 reflections with I > 2σ(I)
T_min = 0.983, T_max = 1.000	R_int = 0.016
5838 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.031	0 restraints
wR(F²) = 0.083	H atoms treated by a mixture of independent and constrained refinement
S = 1.06	Δρ_max = 0.25 e Å⁻³
3253 reflections	Δρ_min = −0.37 e Å⁻³
232 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	0.35277 (5)	0.03423 (5)	0.36846 (5)	0.02726 (14)
P1	0.73295 (5)	0.38427 (4)	0.38957 (5)	0.01865 (13)
O1	0.68787 (12)	0.51744 (12)	0.46676 (12)	0.0219 (3)
O2	0.64902 (13)	0.10825 (13)	0.30353 (13)	0.0287 (3)
N1	0.58216 (17)	0.31087 (16)	0.42742 (16)	0.0201 (4)
N2	0.78048 (15)	0.38421 (15)	0.22483 (14)	0.0219 (3)
N3	0.87044 (15)	0.29050 (14)	0.43213 (15)	0.0216 (3)
C1	0.55954 (19)	0.18865 (18)	0.38376 (18)	0.0205 (4)
C2	0.40604 (18)	0.16286 (18)	0.45401 (18)	0.0217 (4)
H2A	0.3347	0.2491	0.4595	0.026*
H2B	0.4035	0.1350	0.5474	0.026*
C3	0.9309 (2)	0.3970 (2)	0.15080 (19)	0.0318 (5)
H3A	0.9552	0.3517	0.0611	0.048*
H3B	0.9999	0.3536	0.2009	0.048*
H3C	0.9378	0.4941	0.1410	0.048*
C4	0.6704 (2)	0.42144 (19)	0.14777 (19)	0.0275 (5)
H4A	0.5718	0.4206	0.2087	0.033*
H4B	0.6879	0.3508	0.0750	0.033*
C5	0.67105 (19)	0.55997 (18)	0.08528 (18)	0.0220 (4)
C6	0.6768 (2)	0.5718 (2)	−0.05137 (19)	0.0279 (4)
H6A	0.6827	0.4925	−0.1052	0.033*
C7	0.6740 (2)	0.6988 (2)	−0.1093 (2)	0.0298 (5)
H7A	0.6778	0.7057	−0.2026	0.036*
C8	0.6658 (2)	0.8148 (2)	−0.0331 (2)	0.0292 (5)
H8A	0.6639	0.9014	−0.0735	0.035*
C9	0.6604 (2)	0.80430 (19)	0.1031 (2)	0.0292 (5)
H9A	0.6551	0.8838	0.1564	0.035*
C10	0.6627 (2)	0.67757 (19)	0.16120 (19)	0.0256 (4)
H10A	0.6585	0.6711	0.2546	0.031*
C11	0.9385 (2)	0.15360 (18)	0.37333 (19)	0.0292 (5)
H11A	1.0446	0.1490	0.3388	0.044*
H11B	0.8972	0.1342	0.2990	0.044*
H11C	0.9193	0.0858	0.4427	0.044*
C12	0.9306 (2)	0.33736 (19)	0.53760 (19)	0.0259 (4)
H12A	0.8888	0.4355	0.5596	0.031*
H12B	1.0381	0.3295	0.5013	0.031*
C13	0.90090 (19)	0.25971 (17)	0.66624 (18)	0.0224 (4)
C14	0.7603 (2)	0.23941 (18)	0.73019 (19)	0.0250 (4)
H14A	0.6822	0.2705	0.6901	0.030*
C15	0.7324 (2)	0.1745 (2)	0.85159 (19)	0.0296 (5)
H15A	0.6353	0.1621	0.8946	0.035*
C16	0.8448 (2)	0.12755 (19)	0.9108 (2)	0.0318 (5)
H16A	0.8254	0.0829	0.9943	0.038*
C17	0.9843 (2)	0.1458 (2)	0.8484 (2)	0.0369 (5)
H17A	1.0621	0.1133	0.8884	0.044*
C18	1.0130 (2)	0.2115 (2)	0.7269 (2)	0.0316 (5)
H18A	1.1103	0.2237	0.6846	0.038*
H1N	0.512 (2)	0.359 (2)	0.4672 (18)	0.022 (6)*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Cl1	0.0285 (3)	0.0242 (3)	0.0337 (3)	−0.0101 (2)	−0.0129 (2)	0.0023 (2)
P1	0.0146 (2)	0.0162 (2)	0.0238 (3)	−0.00197 (18)	−0.00340 (19)	0.00312 (19)
O1	0.0177 (6)	0.0183 (7)	0.0288 (7)	−0.0027 (5)	−0.0051 (5)	0.0008 (5)
O2	0.0228 (7)	0.0233 (7)	0.0354 (8)	−0.0023 (6)	−0.0007 (6)	−0.0064 (6)
N1	0.0138 (8)	0.0174 (8)	0.0251 (9)	−0.0002 (7)	−0.0001 (7)	−0.0008 (7)
N2	0.0179 (8)	0.0227 (8)	0.0231 (9)	−0.0024 (6)	−0.0027 (7)	0.0048 (7)
N3	0.0183 (8)	0.0197 (8)	0.0257 (9)	0.0001 (6)	−0.0065 (7)	0.0025 (7)
C1	0.0223 (10)	0.0184 (9)	0.0220 (10)	−0.0026 (8)	−0.0089 (8)	0.0037 (8)
C2	0.0212 (9)	0.0183 (9)	0.0262 (10)	−0.0055 (8)	−0.0058 (8)	−0.0006 (8)
C3	0.0243 (10)	0.0355 (12)	0.0280 (11)	−0.0028 (9)	0.0045 (9)	0.0054 (9)
C4	0.0355 (11)	0.0262 (11)	0.0250 (11)	−0.0104 (9)	−0.0123 (9)	0.0041 (8)
C5	0.0189 (9)	0.0246 (10)	0.0247 (10)	−0.0065 (8)	−0.0079 (8)	0.0055 (8)
C6	0.0298 (11)	0.0282 (11)	0.0286 (11)	−0.0089 (9)	−0.0105 (9)	0.0022 (9)
C7	0.0293 (11)	0.0388 (12)	0.0250 (11)	−0.0118 (9)	−0.0102 (9)	0.0123 (9)
C8	0.0244 (10)	0.0255 (11)	0.0408 (12)	−0.0080 (8)	−0.0122 (9)	0.0145 (9)
C9	0.0256 (10)	0.0230 (10)	0.0394 (12)	−0.0051 (8)	−0.0089 (9)	0.0007 (9)
C10	0.0265 (10)	0.0292 (11)	0.0228 (10)	−0.0071 (8)	−0.0083 (8)	0.0046 (8)
C11	0.0225 (10)	0.0228 (10)	0.0387 (12)	0.0046 (8)	−0.0074 (9)	0.0007 (9)
C12	0.0184 (9)	0.0256 (10)	0.0366 (12)	−0.0074 (8)	−0.0099 (9)	0.0056 (9)
C13	0.0228 (9)	0.0163 (9)	0.0299 (11)	−0.0035 (8)	−0.0100 (8)	−0.0027 (8)
C14	0.0232 (10)	0.0232 (10)	0.0320 (11)	−0.0049 (8)	−0.0125 (9)	0.0010 (9)
C15	0.0289 (11)	0.0309 (11)	0.0315 (12)	−0.0121 (9)	−0.0079 (9)	0.0009 (9)
C16	0.0416 (12)	0.0290 (11)	0.0285 (11)	−0.0089 (9)	−0.0140 (10)	0.0039 (9)
C17	0.0339 (12)	0.0396 (13)	0.0404 (13)	0.0013 (10)	−0.0205 (10)	0.0046 (10)
C18	0.0217 (10)	0.0382 (12)	0.0363 (12)	−0.0041 (9)	−0.0109 (9)	0.0037 (10)

Geometric parameters (Å, º) top

Cl1—C2	1.7723 (17)	C7—C8	1.376 (3)
P1—O1	1.4836 (12)	C7—H7A	0.9500
P1—N3	1.6302 (14)	C8—C9	1.388 (3)
P1—N2	1.6313 (15)	C8—H8A	0.9500
P1—N1	1.6866 (15)	C9—C10	1.387 (3)
O2—C1	1.206 (2)	C9—H9A	0.9500
N1—C1	1.368 (2)	C10—H10A	0.9500
N1—H1N	0.773 (18)	C11—H11A	0.9800
N2—C3	1.472 (2)	C11—H11B	0.9800
N2—C4	1.472 (2)	C11—H11C	0.9800
N3—C11	1.461 (2)	C12—C13	1.510 (2)
N3—C12	1.465 (2)	C12—H12A	0.9900
C1—C2	1.526 (2)	C12—H12B	0.9900
C2—H2A	0.9900	C13—C14	1.386 (2)
C2—H2B	0.9900	C13—C18	1.390 (3)
C3—H3A	0.9800	C14—C15	1.382 (2)
C3—H3B	0.9800	C14—H14A	0.9500
C3—H3C	0.9800	C15—C16	1.381 (3)
C4—C5	1.512 (2)	C15—H15A	0.9500
C4—H4A	0.9900	C16—C17	1.367 (3)
C4—H4B	0.9900	C16—H16A	0.9500
C5—C10	1.388 (2)	C17—C18	1.387 (3)
C5—C6	1.393 (2)	C17—H17A	0.9500
C6—C7	1.388 (3)	C18—H18A	0.9500
C6—H6A	0.9500

O1—P1—N3	110.79 (7)	C8—C7—C6	120.72 (18)
O1—P1—N2	118.78 (7)	C8—C7—H7A	119.6
N3—P1—N2	105.79 (8)	C6—C7—H7A	119.6
O1—P1—N1	105.09 (7)	C7—C8—C9	119.47 (17)
N3—P1—N1	111.96 (8)	C7—C8—H8A	120.3
N2—P1—N1	104.33 (8)	C9—C8—H8A	120.3
C1—N1—P1	130.67 (14)	C10—C9—C8	119.86 (18)
C1—N1—H1N	114.7 (14)	C10—C9—H9A	120.1
P1—N1—H1N	113.9 (14)	C8—C9—H9A	120.1
C3—N2—C4	114.46 (15)	C9—C10—C5	121.12 (18)
C3—N2—P1	120.68 (13)	C9—C10—H10A	119.4
C4—N2—P1	121.30 (12)	C5—C10—H10A	119.4
C11—N3—C12	115.28 (14)	N3—C11—H11A	109.5
C11—N3—P1	123.34 (12)	N3—C11—H11B	109.5
C12—N3—P1	121.34 (12)	H11A—C11—H11B	109.5
O2—C1—N1	125.44 (16)	N3—C11—H11C	109.5
O2—C1—C2	123.36 (15)	H11A—C11—H11C	109.5
N1—C1—C2	111.16 (15)	H11B—C11—H11C	109.5
C1—C2—Cl1	112.44 (12)	N3—C12—C13	114.54 (14)
C1—C2—H2A	109.1	N3—C12—H12A	108.6
Cl1—C2—H2A	109.1	C13—C12—H12A	108.6
C1—C2—H2B	109.1	N3—C12—H12B	108.6
Cl1—C2—H2B	109.1	C13—C12—H12B	108.6
H2A—C2—H2B	107.8	H12A—C12—H12B	107.6
N2—C3—H3A	109.5	C14—C13—C18	118.12 (18)
N2—C3—H3B	109.5	C14—C13—C12	121.04 (16)
H3A—C3—H3B	109.5	C18—C13—C12	120.79 (16)
N2—C3—H3C	109.5	C15—C14—C13	120.82 (17)
H3A—C3—H3C	109.5	C15—C14—H14A	119.6
H3B—C3—H3C	109.5	C13—C14—H14A	119.6
N2—C4—C5	114.34 (14)	C16—C15—C14	120.40 (18)
N2—C4—H4A	108.7	C16—C15—H15A	119.8
C5—C4—H4A	108.7	C14—C15—H15A	119.8
N2—C4—H4B	108.7	C17—C16—C15	119.44 (19)
C5—C4—H4B	108.7	C17—C16—H16A	120.3
H4A—C4—H4B	107.6	C15—C16—H16A	120.3
C10—C5—C6	118.48 (16)	C16—C17—C18	120.46 (18)
C10—C5—C4	121.77 (16)	C16—C17—H17A	119.8
C6—C5—C4	119.73 (17)	C18—C17—H17A	119.8
C7—C6—C5	120.34 (18)	C17—C18—C13	120.75 (18)
C7—C6—H6A	119.8	C17—C18—H18A	119.6
C5—C6—H6A	119.8	C13—C18—H18A	119.6

O1—P1—N1—C1	178.95 (16)	N2—C4—C5—C6	129.08 (17)
N3—P1—N1—C1	−60.70 (18)	C10—C5—C6—C7	−0.1 (3)
N2—P1—N1—C1	53.24 (18)	C4—C5—C6—C7	178.50 (17)
O1—P1—N2—C3	83.81 (15)	C5—C6—C7—C8	0.1 (3)
N3—P1—N2—C3	−41.38 (15)	C6—C7—C8—C9	0.0 (3)
N1—P1—N2—C3	−159.63 (13)	C7—C8—C9—C10	−0.3 (3)
O1—P1—N2—C4	−73.72 (15)	C8—C9—C10—C5	0.3 (3)
N3—P1—N2—C4	161.09 (13)	C6—C5—C10—C9	−0.1 (3)
N1—P1—N2—C4	42.84 (15)	C4—C5—C10—C9	−178.68 (17)
O1—P1—N3—C11	179.82 (13)	C11—N3—C12—C13	−67.5 (2)
N2—P1—N3—C11	−50.20 (15)	P1—N3—C12—C13	110.20 (16)
N1—P1—N3—C11	62.85 (15)	N3—C12—C13—C14	−50.5 (2)
O1—P1—N3—C12	2.28 (15)	N3—C12—C13—C18	132.22 (18)
N2—P1—N3—C12	132.27 (13)	C18—C13—C14—C15	0.8 (3)
N1—P1—N3—C12	−114.68 (13)	C12—C13—C14—C15	−176.61 (16)
P1—N1—C1—O2	−1.4 (3)	C13—C14—C15—C16	−0.6 (3)
P1—N1—C1—C2	176.42 (13)	C14—C15—C16—C17	0.0 (3)
O2—C1—C2—Cl1	−19.1 (2)	C15—C16—C17—C18	0.3 (3)
N1—C1—C2—Cl1	162.99 (12)	C16—C17—C18—C13	−0.1 (3)
C3—N2—C4—C5	−51.7 (2)	C14—C13—C18—C17	−0.4 (3)
P1—N2—C4—C5	107.18 (16)	C12—C13—C18—C17	176.96 (18)
N2—C4—C5—C10	−52.4 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
N1—H1N···O1ⁱ	0.773 (18)	2.037 (19)	2.795 (2)	167.1 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formula	C₁₈H₂₃ClN₃O₂P
M_r	379.81
Crystal system, space group	Triclinic, P1
Temperature (K)	120
a, b, c (Å)	9.5891 (8), 9.9259 (7), 10.2543 (8)
α, β, γ (°)	89.509 (6), 74.945 (7), 79.921 (6)
V (Å³)	927.27 (12)
Z	2
Radiation type	Mo Kα
µ (mm⁻¹)	0.31
Crystal size (mm)	0.40 × 0.40 × 0.20

Data collection
Diffractometer	Oxford Diffraction Xcalibur Sapphire2 diffractometer
Absorption correction	Multi-scan (CrysAlis RED; Oxford Diffraction, 2009)
T_min, T_max	0.983, 1.000
No. of measured, independent and observed [I > 2σ(I)] reflections	5838, 3253, 2594
R_int	0.016
(sin θ/λ)_max (Å⁻¹)	0.595

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.031, 0.083, 1.06
No. of reflections	3253
No. of parameters	232
H-atom treatment	H atoms treated by a mixture of independent and constrained refinement
Δρ_max, Δρ_min (e Å⁻³)	0.25, −0.37

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	0.773 (18)	2.037 (19)	2.795 (2)	167.1 (19)

Symmetry code: (i) −x+1, −y+1, −z+1.

Acknowledgements

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

References

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