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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 66| Part 12| December 2010| Page o3159
https://doi.org/10.1107/S1600536810045927

N,N′-Di-tert-butyl-N′′-(2,6-di­fluoro­benzo­yl)phospho­ric tri­amide

Mehrdad Pourayoubi,a* Atekeh Tarahhomi,a Arnold L. Rheingoldb and James A. Golenb

aDepartment of Chemistry, Ferdowsi University of Mashhad, Mashhad, 91779, Iran, and bDepartment of Chemistry, University of California, San Diego, 9500 Gilman, Drive, La Jolla, CA 92093, USA
*Correspondence e-mail: mehrdad_pourayoubi@yahoo.com

(Received 20 October 2010; accepted 8 November 2010; online 13 November 2010)

In the title compound, C15H24F2N3O2P, the phosphoryl and carbonyl groups adopt anti positions relative to each other. The P atom is in a tetra­hedral coordination environment and the environment of each N atom is essentially planar. 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 the a axis. The crystal studied was a non-merohedral twin with a minor twin component of 36.4 (1)%.

Related literature

Carbacyl­amido­phosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as O,O′-donor ligands for metal complexation, see: Gholivand et al. (2010[Gholivand, K., Mahzouni, H. R., Pourayoubi, M. & Amiri, S. (2010). Inorg. Chim. Acta, 363, 2318-2324.]). CELL_NOW (Sheldrick, 2008a[Sheldrick, G. M. (2008a). CELL_NOW and TWINABS. University of Göttingen, Germany.]) was used to generate the components of the twin.

[Scheme 1]

Experimental

Crystal data

  • C15H24F2N3O2P

  • Mr = 347.34

  • Triclinic, [P \overline 1]

  • a = 9.8142 (12) Å

  • b = 10.2886 (13) Å

  • c = 10.6091 (16) Å

  • α = 117.171 (4)°

  • β = 98.636 (4)°

  • γ = 97.988 (3)°

  • V = 915.6 (2) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 0.18 mm−1

  • T = 200 K

  • 0.30 × 0.25 × 0.20 mm
Data collection

  • Bruker SMART X2S benchtop CCD area-detector diffractometer

  • Absorption correction: multi-scan (TWINABS; Sheldrick, 2008a[Sheldrick, G. M. (2008a). CELL_NOW and TWINABS. University of Göttingen, Germany.]) Tmin = 0.948, Tmax = 0.965

  • 7847 measured reflections

  • 4225 independent reflections

  • 3525 reflections with I > 2σ(I)

  • Rint = 0.057
Refinement

  • R[F2 > 2σ(F2)] = 0.049

  • wR(F2) = 0.121

  • S = 1.05

  • 4225 reflections

  • 224 parameters

  • 3 restraints

  • H atoms treated by a mixture of independent and constrained refinement

  • Δρmax = 0.35 e Å−3

  • Δρmin = −0.27 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A D—H H⋯A D⋯A D—H⋯A
N1—H1N⋯O2i 0.86 (1) 1.96 (1) 2.808 (2) 172 (2)
N2—H2N⋯O1ii 0.86 (1) 2.22 (1) 3.042 (2) 160 (2)
N3—H3N⋯O1ii 0.86 (1) 2.22 (2) 3.008 (2) 152 (2)
Symmetry codes: (i) -x, -y+1, -z+1; (ii) -x+1, -y+1, -z+1.

Data collection: GIS (Bruker, 2009[Bruker (2009). GIS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2009[Bruker (2009). GIS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b[Sheldrick, G. M. (2008b). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: https://doi.org/10.1107/S1600536810045927/ng5051sup1.cif

Structure factors: contains datablock I. DOI: https://doi.org/10.1107/S1600536810045927/ng5051Isup2.hkl

checkCIF report


Comment top

Carbacylamidophosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as the O,O'-donor ligands for metal complexation (Gholivand et al., 2010).

Here, we report on the synthesis and crystal structure of title carbacylamidophosphate, P(O)[NHC(O)C6H3(2,6-F2)][NHC(CH3)3]2. The phosphoryl and carbonyl groups adopt the anti position to each other. The P atom has a slightly distorted tetrahedral configuration (Fig. 1). The bond angles around the P atom are in the range of 102.21 (9)° to 116.57 (10)°. The P1–N2 and P1–N3 bonds (1.631 (2) Å and 1.6301 (18) Å) are shorter than the P1–N1 bond (1.7142 (17) Å). The environment of the nitrogen atoms is essentially planar. The P═O bond length of 1.4761 (16) 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. The crystals were found to be twinned.

Related literature top

Carbacylamidophosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as the O,O'-donor ligands for metal complexation, see: Gholivand et al. (2010). CELL_NOW (Sheldrick, 2008a) was used to generate the two components of the twin

Experimental top

2,6-F2—C6H3C(O)NHP(O)Cl2 has been synthesized from the reaction between phosphorus pentachloride (3.478 g, 16.7 mmol) and 2,6-difluorobenzamide (2.624 g, 16.7 mmol) in dry CCl4 at 358 K (3 h) and then the treatment of formic acid (0.769 g, 16.7 mmol) at ice bath temperature.

To a solution of 2,6-F2—C6H3C(O)NHP(O)Cl2 (0.500 g, 1.825 mmol) in dry CHCl3, a solution of tert-butylamine (0.534 g, 7.300 mmol) in dry CHCl3 (1:4 mole ratio) 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 solution of the title compound in DMF/CH3OH and n-C7H16 after a slow evaporation at room temperature. Colorless crystal of the title compound was mounted on a Mitogen mount with epoxy and data was collected at 200 K on a Bruker SMART X2S system with Mo Kα radiation. IR (KBr, cm-1): 3351 (NH), 3094 (NH), 2960, 2202, 1665 (C═O), 1474, 1398, 1239 (P═O), 1020, 878 (P—Namine), 779 (P—Namide).

Refinement top

Structure was solved by direct methods and all non-hydrogen atoms were refined as being anisotropic by Fourier full matrix least squares on F2. Hydrogen atoms on various N atoms were found from a Fourier difference map and these N–H distances were then refined with the distance restraint N–H 0.87 (1) angstrom and with Uiso(H) = 1.2 Ueq(N). All other H atoms were placed in geometrically idealized positions and constrained to ride on their parent atoms with aromatic CH distances of 0.95 Å, Uiso(H) = 1.2Ueq(C) and with methyl C–H distances of 0.98 Å, Uiso(H) = 1.5Ueq(C).

Number of reflections and value of Rint were changed to indicate values given in .ABS, .PRP, and .LST files.

Plat 242 ALERT C - comment on C12 low Ueq in comparison to neighbors. C12 is central atom of a tert-butyl group and attached C atoms have higher Ueq values.

Structure description top

Carbacylamidophosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as the O,O'-donor ligands for metal complexation (Gholivand et al., 2010).

Here, we report on the synthesis and crystal structure of title carbacylamidophosphate, P(O)[NHC(O)C6H3(2,6-F2)][NHC(CH3)3]2. The phosphoryl and carbonyl groups adopt the anti position to each other. The P atom has a slightly distorted tetrahedral configuration (Fig. 1). The bond angles around the P atom are in the range of 102.21 (9)° to 116.57 (10)°. The P1–N2 and P1–N3 bonds (1.631 (2) Å and 1.6301 (18) Å) are shorter than the P1–N1 bond (1.7142 (17) Å). The environment of the nitrogen atoms is essentially planar. The P═O bond length of 1.4761 (16) 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. The crystals were found to be twinned.

Carbacylamidophosphates with a C(O)NHP(O) skeleton have attracted attention because of their roles as the O,O'-donor ligands for metal complexation, see: Gholivand et al. (2010). CELL_NOW (Sheldrick, 2008a) was used to generate the two components of the twin

Computing details top

Data collection: GIS (Bruker, 2009); cell refinement: SAINT (Bruker, 2009); data reduction: SAINT (Bruker, 2009); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008b); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008b); molecular graphics: SHELXTL (Sheldrick, 2008b); software used to prepare material for publication: SHELXTL (Sheldrick, 2008b).

Figures top
[Figure 1] Fig. 1. An ORTEP-style plot of title compound. Ellipsoids are given at the 50% probability level.
N,N'-Di-tert-butyl-N''-(2,6- difluorobenzoyl)phosphoric triamide top
Crystal data top
C15H24F2N3O2PZ = 2
Mr = 347.34F(000) = 368
Triclinic, P1Dx = 1.260 Mg m−3
a = 9.8142 (12) ÅMo Kα radiation, λ = 0.71073 Å
b = 10.2886 (13) ÅCell parameters from 2837 reflections
c = 10.6091 (16) Åθ = 2.2–27.9°
α = 117.171 (4)°µ = 0.18 mm−1
β = 98.636 (4)°T = 200 K
γ = 97.988 (3)°Block, colorless
V = 915.6 (2) Å30.30 × 0.25 × 0.20 mm
Data collection top
Bruker SMART X2S benchtop CCD area-detector
diffractometer		4225 independent reflections
Radiation source: micro focus sealed tube3525 reflections with I > 2σ(I)
Doubly curved silicon crystal monochromatorRint = 0.057
φ and ω scansθmax = 27.9°, θmin = 2.2°
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008a)		h = −12→12
Tmin = 0.948, Tmax = 0.965k = −13→12
7847 measured reflectionsl = 0→13
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)] = 0.049Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05 w = 1/[σ2(Fo2) + (0.0548P)2 + 0.3384P]
where P = (Fo2 + 2Fc2)/3
4225 reflections(Δ/σ)max = 0.007
224 parametersΔρmax = 0.35 e Å−3
3 restraintsΔρmin = −0.27 e Å−3
Crystal data top
C15H24F2N3O2Pγ = 97.988 (3)°
Mr = 347.34V = 915.6 (2) Å3
Triclinic, P1Z = 2
a = 9.8142 (12) ÅMo Kα radiation
b = 10.2886 (13) ŵ = 0.18 mm−1
c = 10.6091 (16) ÅT = 200 K
α = 117.171 (4)°0.30 × 0.25 × 0.20 mm
β = 98.636 (4)°
Data collection top
Bruker SMART X2S benchtop CCD area-detector
diffractometer		4225 independent reflections
Absorption correction: multi-scan
(TWINABS; Sheldrick, 2008a)		3525 reflections with I > 2σ(I)
Tmin = 0.948, Tmax = 0.965Rint = 0.057
7847 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0493 restraints
wR(F2) = 0.121H atoms treated by a mixture of independent and constrained refinement
S = 1.05Δρmax = 0.35 e Å−3
4225 reflectionsΔρmin = −0.27 e Å−3
224 parameters
Special details top

Experimental. Data refinement indicated a twin system and program Cell_Now (Sheldrick, 2008) was used to generate the two components of the twin (63.6 (1)/36.4 ratio). Data was integrated using SAINT and corrected for absorption using TWINABS (Shelrick, 2008).

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
P10.18621 (6)0.39181 (6)0.41180 (6)0.02191 (14)
F10.4134 (2)0.6847 (2)0.94162 (17)0.0611 (5)
F20.23506 (19)0.89470 (17)0.66107 (18)0.0523 (4)
O10.45094 (16)0.62402 (19)0.64132 (18)0.0363 (4)
O20.03152 (16)0.32970 (16)0.36977 (17)0.0305 (4)
N10.20980 (18)0.55903 (19)0.56848 (19)0.0241 (4)
H1N0.1375 (17)0.592 (3)0.595 (3)0.029*
N20.2528 (2)0.4227 (2)0.29337 (19)0.0276 (4)
H2N0.3378 (14)0.411 (3)0.293 (3)0.033*
N30.28600 (19)0.2910 (2)0.4441 (2)0.0260 (4)
H3N0.3739 (13)0.318 (3)0.449 (3)0.031*
C10.3611 (3)0.7959 (3)0.9332 (3)0.0404 (6)
C20.3480 (4)0.9159 (4)1.0587 (3)0.0597 (9)
H2A0.37670.92161.15110.072*
C30.2927 (4)1.0271 (4)1.0475 (4)0.0675 (10)
H3A0.28071.10871.13270.081*
C40.2544 (3)1.0216 (3)0.9142 (4)0.0593 (9)
H4A0.21831.09950.90690.071*
C50.2699 (3)0.8998 (3)0.7919 (3)0.0386 (6)
C60.3228 (2)0.7840 (2)0.7961 (2)0.0283 (5)
C70.3352 (2)0.6488 (2)0.6613 (2)0.0243 (4)
C80.1874 (3)0.4811 (3)0.1991 (2)0.0353 (5)
C90.1621 (4)0.6356 (3)0.2928 (3)0.0580 (9)
H9A0.25180.70420.35980.087*
H9B0.09400.62750.34910.087*
H9C0.12410.67470.22970.087*
C100.0477 (3)0.3691 (4)0.0967 (3)0.0569 (8)
H10A−0.02270.37090.15360.085*
H10B0.06400.26770.04780.085*
H10C0.01260.39720.02340.085*
C110.2913 (4)0.4907 (4)0.1095 (3)0.0535 (7)
H11A0.38090.56110.17500.080*
H11B0.25150.52630.04390.080*
H11C0.30840.39110.05180.080*
C120.2566 (3)0.1929 (3)0.5095 (3)0.0336 (5)
C130.1325 (3)0.0588 (3)0.4049 (4)0.0579 (8)
H13A0.15330.00730.30880.087*
H13B0.04600.09450.39560.087*
H13C0.1188−0.01120.44330.087*
C140.2251 (5)0.2791 (4)0.6581 (4)0.0677 (10)
H14A0.30570.36420.72320.102*
H14B0.20930.21230.69970.102*
H14C0.14000.31650.64700.102*
C150.3893 (3)0.1343 (4)0.5243 (4)0.0525 (7)
H15A0.40900.08020.42800.079*
H15B0.37420.06610.56450.079*
H15C0.47010.21910.58980.079*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
P10.0176 (2)0.0218 (2)0.0242 (3)0.00825 (19)0.00585 (19)0.0082 (2)
F10.0786 (14)0.0696 (11)0.0426 (9)0.0253 (10)0.0115 (8)0.0322 (9)
F20.0626 (11)0.0417 (8)0.0565 (10)0.0198 (8)0.0103 (8)0.0264 (8)
O10.0199 (7)0.0431 (9)0.0381 (9)0.0093 (7)0.0107 (7)0.0117 (7)
O20.0185 (7)0.0288 (7)0.0359 (8)0.0083 (6)0.0062 (6)0.0083 (7)
N10.0179 (8)0.0251 (8)0.0258 (8)0.0100 (7)0.0080 (7)0.0073 (7)
N20.0238 (9)0.0369 (10)0.0278 (9)0.0147 (8)0.0093 (8)0.0174 (8)
N30.0190 (9)0.0280 (9)0.0367 (10)0.0111 (7)0.0116 (8)0.0173 (8)
C10.0370 (14)0.0419 (13)0.0338 (12)0.0027 (11)0.0089 (10)0.0131 (11)
C20.0572 (19)0.067 (2)0.0259 (13)0.0018 (16)0.0120 (12)0.0022 (13)
C30.061 (2)0.0446 (17)0.0517 (18)0.0063 (15)0.0210 (16)−0.0140 (14)
C40.0560 (19)0.0317 (13)0.067 (2)0.0160 (13)0.0164 (16)0.0030 (14)
C50.0337 (13)0.0274 (11)0.0418 (13)0.0036 (10)0.0092 (11)0.0072 (10)
C60.0205 (9)0.0265 (10)0.0276 (10)0.0022 (8)0.0075 (8)0.0052 (8)
C70.0210 (10)0.0264 (10)0.0252 (10)0.0067 (8)0.0083 (8)0.0112 (8)
C80.0437 (14)0.0373 (12)0.0308 (11)0.0163 (11)0.0077 (10)0.0198 (10)
C90.087 (3)0.0501 (16)0.0516 (16)0.0393 (17)0.0195 (16)0.0298 (14)
C100.0501 (18)0.0689 (19)0.0498 (16)0.0046 (14)−0.0106 (13)0.0366 (15)
C110.068 (2)0.0642 (18)0.0426 (15)0.0200 (16)0.0189 (14)0.0346 (14)
C120.0338 (13)0.0360 (12)0.0445 (13)0.0173 (10)0.0172 (10)0.0259 (11)
C130.0462 (18)0.0477 (16)0.087 (2)0.0019 (13)0.0107 (16)0.0424 (17)
C140.108 (3)0.075 (2)0.0601 (19)0.055 (2)0.052 (2)0.0477 (18)
C150.0503 (17)0.0584 (17)0.0721 (19)0.0294 (14)0.0168 (15)0.0456 (16)
Geometric parameters (Å, º) top
P1—O21.4761 (16)C8—C91.522 (4)
P1—N31.6301 (18)C8—C101.536 (4)
P1—N21.631 (2)C9—H9A0.9800
P1—N11.7142 (17)C9—H9B0.9800
F1—C11.351 (3)C9—H9C0.9800
F2—C51.353 (3)C10—H10A0.9800
O1—C71.226 (2)C10—H10B0.9800
N1—C71.352 (3)C10—H10C0.9800
N1—H1N0.858 (10)C11—H11A0.9800
N2—C81.495 (3)C11—H11B0.9800
N2—H2N0.860 (10)C11—H11C0.9800
N3—C121.485 (3)C12—C141.520 (4)
N3—H3N0.856 (10)C12—C151.526 (3)
C1—C21.381 (4)C12—C131.532 (4)
C1—C61.390 (4)C13—H13A0.9800
C2—C31.377 (5)C13—H13B0.9800
C2—H2A0.9500C13—H13C0.9800
C3—C41.381 (6)C14—H14A0.9800
C3—H3A0.9500C14—H14B0.9800
C4—C51.380 (4)C14—H14C0.9800
C4—H4A0.9500C15—H15A0.9800
C5—C61.381 (3)C15—H15B0.9800
C6—C71.509 (3)C15—H15C0.9800
C8—C111.517 (4)
O2—P1—N3116.57 (10)C8—C9—H9A109.5
O2—P1—N2115.98 (9)C8—C9—H9B109.5
N3—P1—N2102.21 (9)H9A—C9—H9B109.5
O2—P1—N1103.22 (8)C8—C9—H9C109.5
N3—P1—N1109.37 (9)H9A—C9—H9C109.5
N2—P1—N1109.43 (10)H9B—C9—H9C109.5
C7—N1—P1126.27 (14)C8—C10—H10A109.5
C7—N1—H1N113.8 (16)C8—C10—H10B109.5
P1—N1—H1N119.9 (16)H10A—C10—H10B109.5
C8—N2—P1127.01 (16)C8—C10—H10C109.5
C8—N2—H2N118.1 (19)H10A—C10—H10C109.5
P1—N2—H2N114.6 (19)H10B—C10—H10C109.5
C12—N3—P1128.21 (15)C8—C11—H11A109.5
C12—N3—H3N114.1 (19)C8—C11—H11B109.5
P1—N3—H3N114.8 (18)H11A—C11—H11B109.5
F1—C1—C2119.7 (3)C8—C11—H11C109.5
F1—C1—C6117.6 (2)H11A—C11—H11C109.5
C2—C1—C6122.7 (3)H11B—C11—H11C109.5
C3—C2—C1118.8 (3)N3—C12—C14111.4 (2)
C3—C2—H2A120.6N3—C12—C15106.2 (2)
C1—C2—H2A120.6C14—C12—C15110.4 (2)
C2—C3—C4120.9 (3)N3—C12—C13109.3 (2)
C2—C3—H3A119.5C14—C12—C13110.8 (3)
C4—C3—H3A119.5C15—C12—C13108.5 (2)
C3—C4—C5118.3 (3)C12—C13—H13A109.5
C3—C4—H4A120.9C12—C13—H13B109.5
C5—C4—H4A120.9H13A—C13—H13B109.5
F2—C5—C4118.7 (3)C12—C13—H13C109.5
F2—C5—C6117.9 (2)H13A—C13—H13C109.5
C4—C5—C6123.4 (3)H13B—C13—H13C109.5
C5—C6—C1116.0 (2)C12—C14—H14A109.5
C5—C6—C7123.1 (2)C12—C14—H14B109.5
C1—C6—C7120.9 (2)H14A—C14—H14B109.5
O1—C7—N1124.00 (18)C12—C14—H14C109.5
O1—C7—C6121.48 (18)H14A—C14—H14C109.5
N1—C7—C6114.52 (17)H14B—C14—H14C109.5
N2—C8—C11106.6 (2)C12—C15—H15A109.5
N2—C8—C9110.46 (19)C12—C15—H15B109.5
C11—C8—C9110.4 (2)H15A—C15—H15B109.5
N2—C8—C10109.0 (2)C12—C15—H15C109.5
C11—C8—C10109.5 (2)H15A—C15—H15C109.5
C9—C8—C10110.8 (2)H15B—C15—H15C109.5
O2—P1—N1—C7169.82 (18)C4—C5—C6—C7178.0 (2)
N3—P1—N1—C745.1 (2)F1—C1—C6—C5−180.0 (2)
N2—P1—N1—C7−66.1 (2)C2—C1—C6—C5−0.3 (4)
O2—P1—N2—C838.0 (2)F1—C1—C6—C72.0 (3)
N3—P1—N2—C8165.93 (18)C2—C1—C6—C7−178.3 (2)
N1—P1—N2—C8−78.2 (2)P1—N1—C7—O13.1 (3)
O2—P1—N3—C12−33.9 (2)P1—N1—C7—C6−175.92 (16)
N2—P1—N3—C12−161.48 (19)C5—C6—C7—O1114.8 (3)
N1—P1—N3—C1282.6 (2)C1—C6—C7—O1−67.3 (3)
F1—C1—C2—C3−179.2 (3)C5—C6—C7—N1−66.1 (3)
C6—C1—C2—C31.1 (5)C1—C6—C7—N1111.8 (2)
C1—C2—C3—C4−1.8 (5)P1—N2—C8—C11179.62 (18)
C2—C3—C4—C51.5 (5)P1—N2—C8—C959.7 (3)
C3—C4—C5—F2−178.8 (3)P1—N2—C8—C10−62.3 (3)
C3—C4—C5—C6−0.6 (4)P1—N3—C12—C14−55.9 (3)
F2—C5—C6—C1178.2 (2)P1—N3—C12—C15−176.14 (19)
C4—C5—C6—C10.0 (4)P1—N3—C12—C1367.0 (3)
F2—C5—C6—C7−3.8 (3)
Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.86 (1)1.96 (1)2.808 (2)172 (2)
N2—H2N···O1ii0.86 (1)2.22 (1)3.042 (2)160 (2)
N3—H3N···O1ii0.86 (1)2.22 (2)3.008 (2)152 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.

Experimental details

Crystal data
Chemical formulaC15H24F2N3O2P
Mr347.34
Crystal system, space groupTriclinic, P1
Temperature (K)200
a, b, c (Å)9.8142 (12), 10.2886 (13), 10.6091 (16)
α, β, γ (°)117.171 (4), 98.636 (4), 97.988 (3)
V (Å3)915.6 (2)
Z2
Radiation typeMo Kα
µ (mm−1)0.18
Crystal size (mm)0.30 × 0.25 × 0.20
Data collection
DiffractometerBruker SMART X2S benchtop CCD area-detector
Absorption correctionMulti-scan
(TWINABS; Sheldrick, 2008a)
Tmin, Tmax0.948, 0.965
No. of measured, independent and
observed [I > 2σ(I)] reflections		7847, 4225, 3525
Rint0.057
(sin θ/λ)max (Å−1)0.658
Refinement
R[F2 > 2σ(F2)], wR(F2), S 0.049, 0.121, 1.05
No. of reflections4225
No. of parameters224
No. of restraints3
H-atom treatmentH atoms treated by a mixture of independent and constrained refinement
Δρmax, Δρmin (e Å−3)0.35, −0.27

Computer programs: GIS (Bruker, 2009), SAINT (Bruker, 2009), SHELXS97 (Sheldrick, 2008b), SHELXL97 (Sheldrick, 2008b), SHELXTL (Sheldrick, 2008b).

Hydrogen-bond geometry (Å, º) top
D—H···AD—HH···AD···AD—H···A
N1—H1N···O2i0.858 (10)1.956 (11)2.808 (2)172 (2)
N2—H2N···O1ii0.860 (10)2.219 (13)3.042 (2)160 (2)
N3—H3N···O1ii0.856 (10)2.224 (15)3.008 (2)152 (2)
Symmetry codes: (i) −x, −y+1, −z+1; (ii) −x+1, −y+1, −z+1.
 

Acknowledgements

Support of this investigation by Ferdowsi University of Mashhad is gratefully acknowledged. The authors wish to thank Bruker AXS, Inc. (Madison, WI) for the use of one of their SMART X2S benchtop instruments.

References

First citationBruker (2009). GIS and SAINT. Bruker AXS Inc., Madison, Wisconsin, USA.  Google Scholar
 First citationGholivand, K., Mahzouni, H. R., Pourayoubi, M. & Amiri, S. (2010). Inorg. Chim. Acta, 363, 2318–2324.  Web of Science CSD CrossRef CAS Google Scholar
 First citationSheldrick, G. M. (2008a). CELL_NOW and TWINABS. University of Göttingen, Germany.  Google Scholar
 First citationSheldrick, G. M. (2008b). Acta Cryst. A64, 112–122.  Web of Science CrossRef CAS IUCr Journals Google Scholar

This is an open-access article distributed under the terms of the Creative Commons Attribution (CC-BY) Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited.

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ISSN: 2056-9890
Volume 66| Part 12| December 2010| Page o3159
https://doi.org/10.1107/S1600536810045927
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