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organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2792
https://doi.org/10.1107/S1600536811039511

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

Mehrdad Pourayoubi,a* Mojtaba Keikhaa and Masood Parvezb

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

(Received 16 August 2011; accepted 26 September 2011; online 30 September 2011)

In the title compound, C16H17Cl3N3O2P, the P—N bonds in the P(O)[NH(2—CH3)C6H4]2 unit [1.623 (4) and 1.637 (3) Å] are shorter than the P—N bond in the C(O)NHP(O) fragment [1.704 (3) Å]. The phosphoryl and carbonyl groups are anti with respect to each other and the P atom has a distorted tetra­hedral configuration. In the crystal, adjacent mol­ecules are linked via N—H⋯O(P) and N—H⋯O(C) hydrogen bonds into an extended chain parallel to [101].

Related literature

For background to compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011[Toghraee, M., Pourayoubi, M. & Divjakovic, V. (2011). Polyhedron, 30, 1680-1690.]); Pourayoubi, Tarahhomi et al. (2011[Pourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265-o272.]). For bond lengths and angles in a related structure, see: Pourayoubi, Fadaei & Parvez (2011[Pourayoubi, M., Fadaei, H. & Parvez, M. (2011). Acta Cryst. E67, o2046.]).

[Scheme 1]

Experimental

Crystal data

  • C16H17Cl3N3O2P

  • Mr = 420.65

  • Monoclinic, C 2/c

  • a = 14.2030 (5) Å

  • b = 16.1935 (6) Å

  • c = 16.9107 (6) Å

  • β = 102.3720 (19)°

  • V = 3799.1 (2) Å3

  • Z = 8

  • Mo Kα radiation

  • μ = 0.58 mm−1

  • T = 173 K

  • 0.10 × 0.09 × 0.08 mm
Data collection

  • Nonius KappaCCD diffractometer with APEXII CCD

  • Absorption correction: multi-scan (SORTAV; Blessing, 1997[Blessing, R. H. (1997). J. Appl. Cryst. 30, 421-426.]) Tmin = 0.944, Tmax = 0.955

  • 8110 measured reflections

  • 4296 independent reflections

  • 3031 reflections with I > 2σ(I)

  • Rint = 0.055
Refinement

  • R[F2 > 2σ(F2)] = 0.071

  • wR(F2) = 0.141

  • S = 1.11

  • 4296 reflections

  • 228 parameters

  • H-atom parameters constrained

  • Δρmax = 0.48 e Å−3

  • Δρmin = −0.38 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 1.90 2.768 (4) 170
N2—H2⋯O1ii 0.88 2.11 2.957 (4) 162
N3—H3⋯O1ii 0.88 2.39 3.149 (4) 144
Symmetry codes: (i) [-x+1, y, -z+{\script{3\over 2}}]; (ii) [-x+{\script{1\over 2}}, -y+{\script{1\over 2}}, -z+1].

Data collection: COLLECT (Hooft, 1998[Hooft, R. (1998). COLLECT. Nonius BV, Delft. The Netherlands.]); cell refinement: DENZO (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); data reduction: SCALEPACK (Otwinowski & Minor, 1997[Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, Macromolecular Crystallography, Part A, edited by C. W. Carter Jr & R. M. Sweet, pp. 307-326. New York: Academic Press.]); program(s) used to solve structure: SIR92 (Altomare et al., 1993[Altomare, A., Cascarano, G., Giacovazzo, C. & Guagliardi, A. (1993). J. Appl. Cryst. 26, 343-350.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: Mercury (Macrae et al., 2008[Macrae, C. F., Bruno, I. J., Chisholm, J. A., Edgington, P. R., McCabe, P., Pidcock, E., Rodriguez-Monge, L., Taylor, R., van de Streek, J. & Wood, P. A. (2008). J. Appl. Cryst. 41, 466-470.]); software used to prepare material for publication: SHELXL97 and enCIFer (Allen et al., 2004[Allen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335-338.]).

Supporting information

Crystal structure: contains datablocks global, I. DOI: https://doi.org/10.1107/S1600536811039511/jj2101sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536811039511/jj2101Isup2.hkl

checkCIF report


Comment top

The structure determination of the title compound, P(O)[NHC(O)CCl3][NHC6H4(2-CH3)]2 (Fig. 1), was performed in continuing of works on the synthesis and structural investigation of new phosphoramidate compounds having a C(O)NHP(O) skeleton (Toghraee et al., 2011; Pourayoubi, Tarahhomi et al., 2011).

The phosphoryl and the carbonyl groups adopt the anti positions with respect to each other. The P atom has a distorted tetrahedral conformation. The bond angles around the P atom are in the range of 102.06 (17)° to 117.28 (17)°. As expected, the P1—N2 (1.623 (4) Å) and P1—N3 (1.637 (3) Å) bonds are shorter than the P1—N1 (1.704 (3) Å) bond. The P═O and C═O bond lengths and the P—N—C bond angles are standard for this category of compounds (Pourayoubi, Fadaei & Parvez, 2011).

In the crystal structure, adjacent molecules are linked via NC(O)NHP(O)—H···O(P) and N—H···O(C) hydrogen bonds, into an extended chain parallel to [101], Table 1 and Fig. 2.

Related literature top

For background to compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011); Pourayoubi, Tarahhomi et al. (2011). For bond lengths and angles in a related structure, see: Pourayoubi, Fadaei & Parvez (2011).

Experimental top

CCl3C(O)NHP(O)Cl2 was synthesized from the reaction between phosphorus pentachloride (16.7 mmol) and 2,2,2-trichloroacetamide (16.7 mmol) in dry CCl4 at 358 K (3 h) and then the treatment of formic acid 85% (16.7 mmol) at ice bath temperature. To a solution of CCl3C(O)NHP(O)Cl2 (1.79 mmol) in CHCl3, a solution of o-toluidine (7.16 mmol) in CHCl3 was added dropwise at 273 K. After 4 h of stirring, the solvent was evaporated at room temperature. The solid was washed with distilled water. Single crystals were obtained from a mixture of CH3OH/CH3CN after slow evaporation at room temperature.

Refinement top

H-atoms were included in geometrically idealized positions with N—H = 0.98 Å and C—H = 0.95 and 0.98Å for aryl and methyl type H-atoms, respectively, and were included in the refinement with Uiso(H) = 1.2Ueq(C/N).

Structure description top

The structure determination of the title compound, P(O)[NHC(O)CCl3][NHC6H4(2-CH3)]2 (Fig. 1), was performed in continuing of works on the synthesis and structural investigation of new phosphoramidate compounds having a C(O)NHP(O) skeleton (Toghraee et al., 2011; Pourayoubi, Tarahhomi et al., 2011).

The phosphoryl and the carbonyl groups adopt the anti positions with respect to each other. The P atom has a distorted tetrahedral conformation. The bond angles around the P atom are in the range of 102.06 (17)° to 117.28 (17)°. As expected, the P1—N2 (1.623 (4) Å) and P1—N3 (1.637 (3) Å) bonds are shorter than the P1—N1 (1.704 (3) Å) bond. The P═O and C═O bond lengths and the P—N—C bond angles are standard for this category of compounds (Pourayoubi, Fadaei & Parvez, 2011).

In the crystal structure, adjacent molecules are linked via NC(O)NHP(O)—H···O(P) and N—H···O(C) hydrogen bonds, into an extended chain parallel to [101], Table 1 and Fig. 2.

For background to compounds having a C(O)NHP(O) skeleton, see: Toghraee et al. (2011); Pourayoubi, Tarahhomi et al. (2011). For bond lengths and angles in a related structure, see: Pourayoubi, Fadaei & Parvez (2011).

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: SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Figures top
[Figure 1] Fig. 1. The molecular structure of the title compound with ellipsoids shown at the 50% probability level. [Colour key: P atom is violet, O atoms are red, N atoms are blue, Cl atoms are green and C and H atoms are light grey.]
[Figure 2] Fig. 2. Part of the crystal structure of the title compound with N—H···O hydrogen bonds shown as dotted lines (the hydrogen atoms of the C—H units are omitted for clarity). [Symmetry codes: (i)-x+1, y, -z+1.5; (ii) -x+0.5, -y+0.5, -z+1]
N,N'-Bis(2-methylphenyl)-N''-(2,2,2- trichloroacetyl)phosphoric triamide top
Crystal data top
C16H17Cl3N3O2PF(000) = 1728
Mr = 420.65Dx = 1.471 Mg m−3
Monoclinic, C2/cMo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2ycCell parameters from 4137 reflections
a = 14.2030 (5) Åθ = 2.5–27.5°
b = 16.1935 (6) ŵ = 0.58 mm−1
c = 16.9107 (6) ÅT = 173 K
β = 102.3720 (19)°Prism, colorless
V = 3799.1 (2) Å30.10 × 0.09 × 0.08 mm
Z = 8
Data collection top
Nonius KappaCCD
diffractometer with APEXII CCD		4296 independent reflections
Radiation source: fine-focus sealed tube3031 reflections with I > 2σ(I)
Graphite monochromatorRint = 0.055
ω and φ scansθmax = 27.5°, θmin = 2.5°
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		h = −18→18
Tmin = 0.944, Tmax = 0.955k = −20→21
8110 measured reflectionsl = −21→21
Refinement top
Refinement on F2Primary atom site location: structure-invariant direct methods
Least-squares matrix: fullSecondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.071Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.141H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.P)2 + 26.070P]
where P = (Fo2 + 2Fc2)/3
4296 reflections(Δ/σ)max < 0.001
228 parametersΔρmax = 0.48 e Å−3
0 restraintsΔρmin = −0.38 e Å−3
Crystal data top
C16H17Cl3N3O2PV = 3799.1 (2) Å3
Mr = 420.65Z = 8
Monoclinic, C2/cMo Kα radiation
a = 14.2030 (5) ŵ = 0.58 mm−1
b = 16.1935 (6) ÅT = 173 K
c = 16.9107 (6) Å0.10 × 0.09 × 0.08 mm
β = 102.3720 (19)°
Data collection top
Nonius KappaCCD
diffractometer with APEXII CCD		4296 independent reflections
Absorption correction: multi-scan
(SORTAV; Blessing, 1997)		3031 reflections with I > 2σ(I)
Tmin = 0.944, Tmax = 0.955Rint = 0.055
8110 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0710 restraints
wR(F2) = 0.141H-atom parameters constrained
S = 1.11 w = 1/[σ2(Fo2) + (0.P)2 + 26.070P]
where P = (Fo2 + 2Fc2)/3
4296 reflectionsΔρmax = 0.48 e Å−3
228 parametersΔρmin = −0.38 e Å−3
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
xyzUiso*/Ueq
Cl10.23160 (9)0.15298 (9)0.78649 (8)0.0533 (4)
Cl20.09485 (7)0.26270 (8)0.68962 (7)0.0474 (3)
Cl30.27140 (8)0.32851 (9)0.78607 (8)0.0513 (3)
P10.44011 (7)0.21369 (7)0.61189 (6)0.0253 (2)
O10.2270 (2)0.2435 (2)0.58675 (16)0.0383 (7)
O20.53687 (18)0.20089 (18)0.66214 (15)0.0312 (6)
N10.3656 (2)0.2181 (2)0.67847 (18)0.0264 (7)
H10.39040.20940.73010.032*
N20.4268 (2)0.2961 (2)0.5559 (2)0.0350 (8)
H20.38410.29500.50980.042*
N30.3973 (2)0.1417 (2)0.54605 (19)0.0288 (7)
H30.37500.15810.49590.035*
C10.2710 (3)0.2342 (2)0.6560 (2)0.0274 (8)
C20.2186 (3)0.2441 (3)0.7272 (2)0.0349 (10)
C30.4812 (3)0.3707 (3)0.5776 (3)0.0379 (10)
C40.5651 (3)0.3852 (3)0.5521 (3)0.0430 (11)
C50.6135 (4)0.4609 (3)0.5734 (3)0.0556 (15)
H50.67200.47220.55700.067*
C60.5758 (5)0.5179 (4)0.6178 (4)0.0661 (17)
H60.60820.56910.63060.079*
C70.4923 (6)0.5032 (4)0.6446 (4)0.0733 (19)
H70.46820.54320.67620.088*
C80.4446 (4)0.4301 (3)0.6250 (3)0.0565 (14)
H80.38690.41910.64310.068*
C90.6031 (4)0.3245 (3)0.5022 (3)0.0573 (14)
H9A0.65920.34780.48500.069*
H9B0.55310.31080.45440.069*
H9C0.62230.27430.53400.069*
C100.3923 (3)0.0558 (3)0.5609 (2)0.0284 (9)
C110.3738 (3)0.0013 (3)0.4949 (3)0.0319 (9)
C120.3716 (3)−0.0828 (3)0.5109 (3)0.0384 (10)
H120.3599−0.12070.46700.046*
C130.3860 (3)−0.1126 (3)0.5889 (3)0.0426 (11)
H130.3840−0.17030.59830.051*
C140.4031 (3)−0.0585 (3)0.6528 (3)0.0391 (10)
H140.4121−0.07900.70650.047*
C150.4074 (3)0.0250 (3)0.6399 (3)0.0345 (10)
H150.42060.06190.68460.041*
C160.3589 (3)0.0325 (3)0.4097 (3)0.0421 (11)
H16A0.3531−0.01430.37230.051*
H16B0.41410.06670.40400.051*
H16C0.29990.06570.39700.051*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Cl10.0420 (6)0.0706 (9)0.0466 (7)−0.0022 (6)0.0080 (5)0.0227 (6)
Cl20.0251 (5)0.0693 (9)0.0452 (7)0.0064 (5)0.0018 (5)−0.0046 (6)
Cl30.0384 (6)0.0659 (8)0.0473 (7)0.0042 (6)0.0041 (5)−0.0278 (6)
P10.0242 (5)0.0315 (6)0.0181 (5)−0.0012 (4)0.0003 (4)0.0003 (4)
O10.0291 (15)0.057 (2)0.0239 (15)0.0055 (14)−0.0050 (12)0.0003 (14)
O20.0252 (14)0.0454 (18)0.0206 (14)0.0009 (13)−0.0009 (11)−0.0016 (13)
N10.0251 (16)0.0362 (19)0.0149 (15)0.0026 (14)−0.0026 (12)−0.0019 (14)
N20.0348 (19)0.038 (2)0.0263 (18)−0.0065 (16)−0.0060 (15)0.0049 (16)
N30.0327 (18)0.0355 (19)0.0160 (16)0.0003 (15)0.0004 (13)0.0005 (14)
C10.0258 (19)0.030 (2)0.0238 (19)−0.0002 (16)−0.0010 (15)−0.0006 (16)
C20.024 (2)0.049 (3)0.029 (2)0.0001 (19)0.0010 (17)−0.004 (2)
C30.044 (3)0.035 (2)0.030 (2)−0.004 (2)−0.0019 (19)0.0095 (19)
C40.043 (3)0.039 (3)0.041 (3)−0.005 (2)−0.003 (2)0.010 (2)
C50.062 (3)0.044 (3)0.048 (3)−0.013 (3)−0.018 (3)0.015 (3)
C60.092 (5)0.042 (3)0.054 (4)−0.012 (3)−0.008 (3)0.007 (3)
C70.120 (6)0.052 (4)0.046 (3)0.007 (4)0.012 (4)−0.008 (3)
C80.074 (4)0.049 (3)0.042 (3)0.001 (3)0.003 (3)−0.003 (3)
C90.057 (3)0.054 (3)0.060 (4)0.002 (3)0.013 (3)0.004 (3)
C100.0262 (19)0.031 (2)0.028 (2)−0.0005 (17)0.0059 (16)−0.0030 (17)
C110.025 (2)0.041 (2)0.030 (2)−0.0028 (18)0.0072 (17)−0.0067 (19)
C120.037 (2)0.038 (3)0.041 (3)−0.005 (2)0.009 (2)−0.010 (2)
C130.045 (3)0.033 (2)0.051 (3)−0.004 (2)0.012 (2)0.001 (2)
C140.038 (2)0.042 (3)0.038 (3)0.000 (2)0.010 (2)0.004 (2)
C150.038 (2)0.037 (2)0.027 (2)−0.0035 (19)0.0045 (18)0.0002 (19)
C160.049 (3)0.046 (3)0.031 (2)−0.009 (2)0.010 (2)−0.009 (2)
Geometric parameters (Å, º) top
Cl1—C21.771 (5)C6—H60.9500
Cl2—C21.762 (4)C7—C81.369 (8)
Cl3—C21.762 (4)C7—H70.9500
P1—O21.468 (3)C8—H80.9500
P1—N21.623 (4)C9—H9A0.9800
P1—N31.637 (3)C9—H9B0.9800
P1—N11.704 (3)C9—H9C0.9800
O1—C11.213 (4)C10—C151.397 (6)
N1—C11.341 (5)C10—C111.404 (5)
N1—H10.8800C11—C121.390 (6)
N2—C31.439 (5)C11—C161.499 (6)
N2—H20.8800C12—C131.377 (6)
N3—C101.419 (5)C12—H120.9500
N3—H30.8800C13—C141.372 (6)
C1—C21.554 (6)C13—H130.9500
C3—C41.371 (6)C14—C151.373 (6)
C3—C81.420 (7)C14—H140.9500
C4—C51.413 (7)C15—H150.9500
C4—C91.472 (7)C16—H16A0.9800
C5—C61.369 (8)C16—H16B0.9800
C5—H50.9500C16—H16C0.9800
C6—C71.377 (9)
O2—P1—N2115.54 (18)C8—C7—C6119.1 (6)
O2—P1—N3117.28 (17)C8—C7—H7120.4
N2—P1—N3102.06 (17)C6—C7—H7120.4
O2—P1—N1105.08 (15)C7—C8—C3120.0 (6)
N2—P1—N1109.89 (18)C7—C8—H8120.0
N3—P1—N1106.68 (16)C3—C8—H8120.0
C1—N1—P1123.1 (3)C4—C9—H9A109.5
C1—N1—H1118.4C4—C9—H9B109.5
P1—N1—H1118.4H9A—C9—H9B109.5
C3—N2—P1123.6 (3)C4—C9—H9C109.5
C3—N2—H2118.2H9A—C9—H9C109.5
P1—N2—H2118.2H9B—C9—H9C109.5
C10—N3—P1127.1 (3)C15—C10—C11120.0 (4)
C10—N3—H3116.4C15—C10—N3121.0 (4)
P1—N3—H3116.4C11—C10—N3118.9 (4)
O1—C1—N1125.2 (4)C12—C11—C10118.0 (4)
O1—C1—C2120.1 (3)C12—C11—C16120.9 (4)
N1—C1—C2114.7 (3)C10—C11—C16121.1 (4)
C1—C2—Cl2110.2 (3)C13—C12—C11121.7 (4)
C1—C2—Cl3107.5 (3)C13—C12—H12119.2
Cl2—C2—Cl3110.0 (2)C11—C12—H12119.2
C1—C2—Cl1110.1 (3)C14—C13—C12119.7 (4)
Cl2—C2—Cl1108.8 (2)C14—C13—H13120.2
Cl3—C2—Cl1110.3 (2)C12—C13—H13120.2
C4—C3—C8120.6 (5)C13—C14—C15120.7 (4)
C4—C3—N2121.2 (4)C13—C14—H14119.7
C8—C3—N2118.1 (4)C15—C14—H14119.7
C3—C4—C5118.4 (5)C14—C15—C10120.0 (4)
C3—C4—C9121.0 (4)C14—C15—H15120.0
C5—C4—C9120.5 (5)C10—C15—H15120.0
C6—C5—C4119.9 (6)C11—C16—H16A109.5
C6—C5—H5120.0C11—C16—H16B109.5
C4—C5—H5120.0H16A—C16—H16B109.5
C5—C6—C7121.9 (6)C11—C16—H16C109.5
C5—C6—H6119.0H16A—C16—H16C109.5
C7—C6—H6119.0H16B—C16—H16C109.5
O2—P1—N1—C1176.0 (3)N2—C3—C4—C9−0.6 (7)
N2—P1—N1—C151.1 (4)C3—C4—C5—C6−0.6 (7)
N3—P1—N1—C1−58.9 (4)C9—C4—C5—C6178.1 (5)
O2—P1—N2—C3−29.9 (4)C4—C5—C6—C71.6 (8)
N3—P1—N2—C3−158.3 (4)C5—C6—C7—C8−1.2 (9)
N1—P1—N2—C388.8 (4)C6—C7—C8—C3−0.1 (8)
O2—P1—N3—C1051.5 (4)C4—C3—C8—C71.0 (8)
N2—P1—N3—C10178.8 (3)N2—C3—C8—C7−177.7 (5)
N1—P1—N3—C10−65.9 (4)P1—N3—C10—C1512.9 (6)
P1—N1—C1—O13.5 (6)P1—N3—C10—C11−165.8 (3)
P1—N1—C1—C2−174.1 (3)C15—C10—C11—C12−0.3 (6)
O1—C1—C2—Cl23.5 (5)N3—C10—C11—C12178.4 (4)
N1—C1—C2—Cl2−178.7 (3)C15—C10—C11—C16−179.1 (4)
O1—C1—C2—Cl3−116.4 (4)N3—C10—C11—C16−0.3 (6)
N1—C1—C2—Cl361.4 (4)C10—C11—C12—C130.7 (6)
O1—C1—C2—Cl1123.5 (4)C16—C11—C12—C13179.4 (4)
N1—C1—C2—Cl1−58.8 (4)C11—C12—C13—C14−0.1 (7)
P1—N2—C3—C493.0 (5)C12—C13—C14—C15−0.8 (7)
P1—N2—C3—C8−88.3 (5)C13—C14—C15—C101.2 (7)
C8—C3—C4—C5−0.6 (7)C11—C10—C15—C14−0.6 (6)
N2—C3—C4—C5178.1 (4)N3—C10—C15—C14−179.4 (4)
C8—C3—C4—C9−179.3 (5)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.902.768 (4)170
N2—H2···O1ii0.882.112.957 (4)162
N3—H3···O1ii0.882.393.149 (4)144
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1.

Experimental details

Crystal data
Chemical formulaC16H17Cl3N3O2P
Mr420.65
Crystal system, space groupMonoclinic, C2/c
Temperature (K)173
a, b, c (Å)14.2030 (5), 16.1935 (6), 16.9107 (6)
β (°) 102.3720 (19)
V (Å3)3799.1 (2)
Z8
Radiation typeMo Kα
µ (mm−1)0.58
Crystal size (mm)0.10 × 0.09 × 0.08
Data collection
DiffractometerNonius KappaCCD
diffractometer with APEXII CCD
Absorption correctionMulti-scan
(SORTAV; Blessing, 1997)
Tmin, Tmax0.944, 0.955
No. of measured, independent and
observed [I > 2σ(I)] reflections		8110, 4296, 3031
Rint0.055
(sin θ/λ)max (Å−1)0.650
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.071, 0.141, 1.11
No. of reflections4296
No. of parameters228
H-atom treatmentH-atom parameters constrained
w = 1/[σ2(Fo2) + (0.P)2 + 26.070P]
where P = (Fo2 + 2Fc2)/3
Δρmax, Δρmin (e Å−3)0.48, −0.38

Computer programs: COLLECT (Hooft, 1998), DENZO (Otwinowski & Minor, 1997), SCALEPACK (Otwinowski & Minor, 1997), SIR92 (Altomare et al., 1993), Mercury (Macrae et al., 2008), SHELXL97 (Sheldrick, 2008) and enCIFer (Allen et al., 2004).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1···O2i0.881.902.768 (4)169.8
N2—H2···O1ii0.882.112.957 (4)162.2
N3—H3···O1ii0.882.393.149 (4)144.3
Symmetry codes: (i) −x+1, y, −z+3/2; (ii) −x+1/2, −y+1/2, −z+1.
 

Acknowledgements

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

References

First citationAllen, F. H., Johnson, O., Shields, G. P., Smith, B. R. & Towler, M. (2004). J. Appl. Cryst. 37, 335–338.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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 First citationPourayoubi, M., Fadaei, H. & Parvez, M. (2011). Acta Cryst. E67, o2046.  Web of Science CSD CrossRef IUCr Journals Google Scholar
 First citationPourayoubi, M., Tarahhomi, A., Saneei, A., Rheingold, A. L. & Golen, J. A. (2011). Acta Cryst. C67, o265–o272.  Web of Science CSD CrossRef CAS IUCr Journals Google Scholar
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ISSN: 2056-9890
Volume 67| Part 10| October 2011| Page o2792
https://doi.org/10.1107/S1600536811039511
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